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Holiday Rentals with Pools in Osprey

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    Don't let other travellers get your favourite Osprey area holiday rental. You're so close to securing your perfect getaway. Book today.
    507 Matching Rentals in the Osprey AreaView all 832 rentals
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    Welcome to the Paradise1 / 17
    (1)Excellent
    Osprey
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Pet friendly paradise with heated pool close to Sarasota-Osprey-Nokomis-Venice1 / 17
    (1)Average
    Osprey
    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Osprey
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    The following rentals are within 15 kilometers of Osprey.
    Venice
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Balcony
    • Satellite TV
    • Air Conditioning
    • Grill
    • Washer
    • Patio
    • Private Outdoor Pool (Heated)
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Location, location, location, short walk to beach, town, and bike trail. Venice Island was just featured in "Coastal Living Magazine" as one of the best seaside towns in the US. Three bedroom, two bath home with screened pool, veranda and air conditioning . Quiet neighborhood, but close to...
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    Venice, Southwest Gulf Coast 34285
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Reserve now! Siesta key 10% off August and Sept1 / 24
    (2)Excellent
    Siesta Key
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Satellite TV
    • Air Conditioning
    • Housekeeping Included
    • Washer
    • Wi-Fi
    • Waterfront
    • DVD Player
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 27 January 2017
    The condo was everything and more in ad. Very close to the beach. I plan on booking again next year. Rooms were spacious, bedding was comfortable and the kitchen was was awesome...
    Reviewed 8 August 2016
    This condo was very nice. Steps away from the gorgeous white sandy beach and convenient to shopping and restaurants.We were very impressed with not only the condition of the...
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    About this property
    I have tried to make this apartment as comfortable as your own home only at the beach. This unit has two bedrooms and two baths. It can accommodate six people with a king bed and two double beds. There are plenty of closet and dresser space, a fully-equipped kitchen, color TV's, VCR and/or DVD and...
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    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Sea Shell Condo-Right On Crescent Beach-Siesta Key1 / 24
    (5)Excellent
    Siesta Key
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Balcony
    • Air Conditioning
    • Terrace
    • Wi-Fi
    • Grill
    • Ocean Views
    • Parking
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 week ago
    The two bedroom condo was very nice. Enough room to sleep 5-6 probably. On the 2nd floor with a limited beach view. The unit had all the small amenities you need. Good TVs...
    Reviewed 18 April 2017
    We just returned from a weeks stay in unit 210 at the Sea Shell Condominiums. Accommodations were great, including the most beautiful beach and sand with plenty of beach chairs...
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    About this property
    If you are looking for the perfect spot for a family vacation, to escape the cold and snow, or a quiet romantic getaway this is the place for you. Recently updated throughout, this 2 bedroom 2 bath condo sleeps 6 comfortably all in real beds. Just outside your door is Crescent Beach, consistently...
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    Location Information
    Siesta Key, Florida 34243
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Siesta Key
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Patio
    • Satellite TV
    • Washer
    • Wi-Fi
    • Air Conditioning
    • DVD Player
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Unlike many rental properties on Siesta Key, Unit #100 was renovated in 2016! This condo is a 2 bedroom, 2 bath garden view unit located in the quiet area of Jamaica Royale Condominiums! Jamaica Royale is located directly on the Gulf of Mexico along the white sands of world-famous Siesta Key...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Luxury Venice, Florida Gulf Coast Condo1 / 31
    (1)Excellent
    Venice
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • DVD Player
    • Wi-Fi
    • Grill
    • Shared Outdoor Pool (Unheated)
    • Satellite TV
    • Air Conditioning
    • Balcony
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located in St. Andrews Park at the Plantation Golf & Country Club Overlooks Premier Golf Club Facility Country Club Membership A touch of Bermuda is evident in this environmentally friendly 1,300-acre community built around two championship golf courses, lakes and lush tropical preserves. Sand...
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    Location Information
    Venice, Southwest Gulf Coast 34293
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Beautiful Custom Pool Home1 / 18
    (2)Very good
    Venice
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Air Conditioning
    • Patio
    • Wi-Fi
    • Washer
    • Satellite TV
    • Private Outdoor Pool (Heated)
    • Grill
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 April 2016
    The house was very comfortable. However, the outdoor area was the best! The pool could use some updating, but was a wonderful plus for our time spent at this house. We...
    Reviewed 13 January 2016
    Great home close to private ferry/beach with private pool and relaxing lanai. The home was tastefully decorated had ample space to spread out and relax. The pool was nice for...
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    About this property
    Enjoy your vacation relaxing on the screened lanai and swimming in a heated pool. Our custom pool home is located in South Venice and is minutes to the beach. This house has some unique features and nearly every room has direct access to the pool. The master bedroom is BIG with a king size bed...
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    Location Information
    Venice, Southwest Gulf Coast 34293
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Siesta Key 3 Bdrm Private House with Heated Pool minutes from village and beach1 / 29
    (1)Excellent
    Siesta Key
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Waterfront
    • Grill
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Washer
    • Patio
    • Air Conditioning
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 April 2017
    This is a beautiful home a short bike ride to Siesta Beach. It comfortably sleeps 8 on beds in 3 large rooms. 2 of the rooms have a glass door that opens up to the pool and...
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    About this property
    Surrounded by lush, tropical garden, our private villa is situated on a quiet cul-de-sac bordered on two sides by Lake Nancy. A birdwatchers and nature lovers delight! Sip your coffee in your PJs on the private, sunny terrace. Enjoy a dip in the large heated pool, or explore the lake in "Red...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Siesta Key Condo, Crescent Arms, unit 605 South1 / 24
    (8)Excellent
    Siesta Key
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Grill
    • Satellite TV
    • Balcony
    • Secure Parking
    • Air Conditioning
    • Ocean Views
    • DVD Player
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 weeks ago
    I cannot say enough good things about the Owner, Karen and her slice of heaven. To begin with, all communications with Karen were beyond amazing. She has been quick to get back...
    Reviewed 17 May 2017
    We absolutely loved our rental condo in the Crescent Arms community. The condo was clean, comfortable, and fully stocked with all the basic necessities. The owner provides a...
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    About this property
    Split floor plan with each bedroom having a private full bath, tv and access to the lanai. New bathroom floors installed in October 2016 and new tile in master bath/tub. New king size mattress as of May 2017. Secure Wi-fi Relaxing lanai with couch, two chairs and three end tables to enjoy a book...
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    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Beachfront - Gulf View! 2 BR/BA Crescent Arms 603S, #1 Beach in the US.1 / 24
    (6)Excellent
    Siesta Key
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Wi-Fi
    • Air Conditioning
    • Satellite TV
    • Waterfront
    • DVD Player
    • Washer
    • Ocean Views
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 week ago
    Rented 603S condo with a gulf view from the screened in lanai. The condo had every amenity needed for a great week. Beach towels were even provided. The laundry room as well as...
    Reviewed 1 March 2017
    We really enjoyed our stay. The unit has been thoughtfully equipped with dishes, containers and beach items. The space was perfect for my husband and I to share with another...
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    About this property
    - Expansive, panoramic gulf view from every room of this 6th floor condo. -Crescent Arms is a quiet, beach front, high rise condominium building that is ideally located for maximum fun and relaxation. -Right on the beach with lounge chairs provided. As close as you can get to the Gulf without...
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    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Venice
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Amenities & Details
    • Satellite TV
    • Patio
    • Washer
    • Air Conditioning
    • Waterfront
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Relax and unwind in our waterfront vacation home. 3 bdrms, 2 full ensuite baths, sleeps 7. New Posturepedic mattresses and hypo-allergenic pillows for your peaceful and restful sleep. Free Wi-Fi, Smart TV in bedroom & living room. Fully equipped kitchen. Eating area overlooking lake. Kitchen and...
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    Location Information
    Venice, Southwest Gulf Coast 34293
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    Lakefront Villa Plantation, Venice FL1 / 16
    (1)Excellent
    Venice
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Secure Parking
    • Satellite TV
    • Air Conditioning
    • Grill
    • DVD Player
    • Washer
    • Wi-Fi
    • Porch
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 23 November 2014
    The Condo responded to all our expectations. It is very well equipped, and we lacked nothing. The location is central, and all amenities are nearby. We chose this condo from...
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    About this property
    Relax on your vacation for a month or more in Venice, Florida in our newly furnished villa condo on the shore of Harrington Lake while sipping your afternoon cocktail. Venice is a beautiful coastal town with great beaches and lots to do on your Florida vacation. Enjoy all this and make friends...
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    Location Information
    Venice, Southwest Gulf Coast 34293
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Siesta Key Townhouse across from Pristine Sand & B1 / 30
    (14)Excellent
    Siesta Key
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Balcony
    • Air Conditioning
    • DVD Player
    • Grill
    • Satellite TV
    • Washer
    • Secure Parking
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 23 April 2017
    The town home was in the perfect location, just a three minute walk to the the beautiful beach of Siesta Key. The owners had every possible beach amenity you could ask for...
    Reviewed 5 April 2017
    Beautiful townhouse located across from Siesta Beach. Great location! The unit was equipped with everything needed for a wonderful vacation. Owner Michelle was very warm and...
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    About this property
    “Pristine sand, blue skies - 'Number 1 Beach'” <BR><BR>The Best Thing to Come Home to after a Day on the Beach Is...<BR> ...a vacation home as comfortable as your own home. <BR><BR>Just a walk across the street to Siesta Key's world famous #1 Beach.<BR><BR> This split-level townhouse, has 2...
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    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Walk to a FREE beach ferry to Manasota Key!1 / 20
    (1)Excellent
    Venice
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Amenities & Details
    • Internet Access
    • Balcony
    • DVD Player
    • Patio
    • Air Conditioning
    • Satellite TV
    • Washer
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 May 2017
    This location is great - quiet and relaxing! This home is comfortable and meets all of ones needs. Bruce the owner was very welcoming and helped make our stay very enjoyable...
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    About this property
    Location, location, location! Just a 3 block walk to a free boat ride to a private beach on Manasota Key. I provide 5 beach chairs, 5 beach towels and a cooler for your use. The beach ferry runs every day except Wednesday, from 9:30am to sunset. Up to 6 people can use the ferry pass I provide. I...
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    Location Information
    Venice, Southwest Gulf Coast 34293
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Luxury Villa, Siesta Key Beach, Sarasota, Florida1 / 22
    (4)Very good
    Siesta Key
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Air Conditioning
    • Washer
    • Grill
    • Secure Parking
    • Ocean Views
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 September 2016
    The two bedroom cottage is nice. Not luxury, but absolutely adequate. The beach is spectacular. The biggest drawback from the rental was the lack of any sort of outdoor...
    Reviewed 30 November 2015
    Villa was nice. It had all of the amenities needed for a comfortable stay. It was clean. It was only a short walk to the beach. It was close to town center.
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    About this property
    LAST MINUTE DEALS NOW AVAILABLE AUGUST - JANUARY at our luxurious Villa#4 (on Crystal Sands, 6300 Midnight Pass Rd, Sarasota, Florida) - sleeps 6 and includes everything your family needs for your stay at the #1 beach in the USA. This Villa has easy access to the beach without leaving the property...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Venice
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Air Conditioning
    • Parking
    • Private Garden
    • Satellite TV
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This house has it all! All the amenities of home and more. This is a quite neighborhood on a corner lot with a park across the street.Toddler friendly amenities including a pool safety gate, pack-n-play, booster seat, and stroller. Beach chairs, umbrellas, and beach buggy included for no...
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    Location Information
    Venice, Southwest Gulf Coast 34293
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    SIESTA KEY! #1 Beach! Tranquil Gulf-side 2 Bed/2 Bath in Jamaica Royale  #1041 / 19
    (1)Excellent
    Siesta Key
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Patio
    • DVD Player
    • Air Conditioning
    • Secure Parking
    • Grill
    • Washer
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 March 2017
    Truly awesome experience. Quiet garden sid. A home away from home. Nice sheets & new towels. Everything we needed. Very responsive & helpful owner Beach side, 3 pools...
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    About this property
    Jamaica Royale Condominiums are located directly on the Gulf of Mexico along the white sands of world-famous Siesta Key Beach in Sarasota, Florida. A barrier island on Florida’s West coast, considered the most beautiful of Florida’s barrier islands, Siesta Key’s beach boasts “the world’s finest...
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    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Siesta Beach Condo - ***Open dates in August***1 / 24
    (1)Excellent
    Siesta Key
    2 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Satellite TV
    • Air Conditioning
    • Balcony
    • Washer
    • Secure Parking
    • Patio
    • Wi-Fi
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 April 2017
    I have to admit I wasn't expecting our stay to be anything special. We had been to Sarasota and Siesta Key before and stayed in a nice hotel. I wanted to do that again, but my...
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    About this property
    ***AUGUST 2017 AVAILABILITY*** Steps to Siesta Beach and a Gorgeous Condo, Bring the Entire Family! #1 Beach in the US (2017) : Siesta Key is the United States #1 Beach Boasting Miles of Powder White Sand and a Charming Village loaded Shopping, Dining and Ice Cream :) Our 2 bedroom 2.5 bath...
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    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 8
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    Amazing Beachfront Condo, Siesta Key, 100ft+ Beach1 / 31
    (2)Average
    Siesta Key
    2 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Air Conditioning
    • DVD Player
    • Satellite TV
    • Waterfront
    • Ocean Views
    • Patio
    • Wi-Fi
    • Housekeeping Included
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 February 2017
    This condo is just feet away from waves slapping against the shore. It is well stocked with everything you would need while vacationing. It could use a deep cleaning, But...
    Reviewed 30 January 2017
    Great week in Siesta Key as always! Thanks! Will visit again in the near future. Would definitely recommend the Key!
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    About this property
    Great first impressions are evident from the moment you enter this lovely condo and enjoy the breathtaking ocean views from our private oversized lanai. We know you'll adore our comfortably decorated oceanfront condo and have the relaxing vacation you've been dreaming of. This unit unfolds as you...
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    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 7
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    Luxury Venice Home with (heated) Private Pool and Lake View1 / 32
    (4)Excellent
    Venice
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Hot Tub
    • Satellite TV
    • Patio
    • Private Outdoor Pool (Heated)
    • DVD Player
    • Air Conditioning
    • Washer
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 27 March 2015
    Situated in a lovely neighorhood in foresty surroundings with a preserve across the community. Nice community pool, jacuzz and clubhouse. Situated close to a major highway for...
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    About this property
    New (2014 built) four bedroom house in sunny Venice. Our vacation property comes with a fully equipped kitchen and it has a private (screened in) pool and spa (heating available). Our house backs onto a lovely lake where turtles, fish and birds can be frequently spotted. The house is located...
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    Location Information
    Venice, Southwest Gulf Coast 34292
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Ebb Tide #1 Bright, cozy, Siesta Key cottage1 / 24
    (42)Excellent
    Siesta Key
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Grill
    • Washer
    • Patio
    • Air Conditioning
    • Satellite TV
    • Parking
    • DVD Player
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 23 April 2017
    EBB TIDE #1 is perfect for gated access to the award winning white sand beach that's literally a 3 minute walk away. There's also a gated, heated pool available for use on the...
    Reviewed 8 January 2017
    Ebb Tide #1 is a great little cottage for a couple or a couple with a small child. It is in my favorite area of Siesta Key and is a short walk to restaurants, shops, the pool...
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    About this property
    Very clean, bright, airy 1 bedroom, single- story cottage. Ebb Tide #1 offers all you need for a wonderful vacation at the beach. - Beautiful, large, heated, saltwater pool. - Private, gated access to world renowned Crescent Beach, famous for its powdery, white, quartz sand and gorgeous sunsets! -...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Beachfront Getaway in Siesta Key1 / 17
    (10)Excellent
    Siesta Key
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Grill
    • Wi-Fi
    • Parking
    • Private Garden
    • Air Conditioning
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 February 2017
    Very impressive space and proximity to everything that was important to me. I felt welcomed from the first moment I entered this beautifully appointed beach condo. Steps away...
    Reviewed 5 November 2016
    Very well located property. Fixtures and fittings of a high standard. Near all amenities. Definitely to be recommended
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    About this property
    This luxurious one story townhouse was newly renovated and has its own private access to the #1 beach in the US merely steps away from the front door. It boasts all the luxury you'd expect from a beach house! Modern kitchen, contemporary bathroom with walk in rain shower, luxurious bedroom and...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Siesta Key
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Waterfront
    • Ocean Views
    • Wi-Fi
    • Air Conditioning
    • Satellite TV
    • Children's Pool
    • DVD Player
    • Sauna
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    You will feel like you have arrived in Paradise when you enter the lobby. The facility is more like a resort than a condominium. Unit has 2 bedroom, 2 baths, split plan. Both bedrooms and living room open to screened lanai facing the Gulf of Mexico. Perfect setting for 4 adults or for a family with...
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    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Beachfront Ground Level Suite - Remodeled - 2 king bedrooms1 / 40
    (5)Very good
    Siesta Key
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Ocean Views
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    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 September 2016
    If you are an avid beach goer, you're average rental experience probably includes lifting and lugging a million beach accessories and toys (if you have kids) for what seems like...
    Reviewed 16 August 2016
    This unit is literally 200 steps to the water. Fantastic ocean front appeal and it had literally the best master suite mattress that we've had in years for a vacation property...
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    About this property
    Leave your worries behind... If you're looking for a relaxing beachfront condo that's been totally remodeled you've come to the right place. Our ground-level oceanfront condo is the perfect place to unwind unplug and recharge the batteries. Fisherman's Cove is a quiet and relaxed complex on the...
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    Siesta Key, Florida 34242
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Venice Condo On The Beach1 / 52
    (4)Very good
    Venice
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Wi-Fi
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    • Grill
    • Shared Outdoor Pool (Unheated)
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    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 January 2016
    We thoroughly enjoyed our stay here. It is a very nice place. It has everything you need. It was clean and attractive. The bed is comfortable also. What we liked the most was...
    Reviewed 12 August 2015
    We had a great time in Venice. The Condo's location to the beach was perfect. The beach was always clean and private. We really enjoyed the pool as well. The Condo was private...
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    About this property
    Beach front community on Venice Island. This unit is fully furnished and is located next to the large swimming pool. Sorry, but pets are not allowed. You will be staying in a single story end unit studio/one room efficiency with entry directly to the pool. There is also a nice picnic area next the...
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    Location Information
    Venice, Southwest Gulf Coast 34285
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    Crescent Arms 703S, Beachfront Penthouse, Gulf View from Every Room! 2BR/BA1 / 40
    (10)Very good
    Siesta Key
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 week ago
    The location is amazing. Walking distance to Captain Curts and other great restaurants and ice cream shops. The view of the beach is amazing. The owner checked in with is before...
    Reviewed 2 March 2017
    The condo was clean, cozy and well-equipped. The beach sand is almost pure white quartz crystal and it feels like powder or flour on your feet. I couldn’t believe that it never...
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    About this property
    -Accommodations: Condo, 2 Bedrooms + Convertible Bed, 2 Baths (Sleeps 4-6) -Expansive, panoramic gulf view from every room of this 7th (top) floor condo. -Crescent Arms is a quiet, beach front, high rise condominium building that is ideally located for maximum fun and relaxation. -Right on the...
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    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Siesta Key
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    2 bedroom/2 bath top-floor end unit steps from the #1 beach in the County and #3 in the World (voted by Trip Advisor Feb. 2016). Sarasota County spent almost $30 million renovating all of the public facilities - new concession, bathrooms, SunDeck Restaurant, playground equipment and picnic...
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    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Luxurious 2 BR Condo - Short Walk to Siesta Beach1 / 14
    (18)Very good
    Siesta Key
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 April 2017
    We stayed at the apartment for 2 weeks during Easter holidays with our 2 girls (aged 1 and 4). We had a lovely holiday. We felt there was some positives and negatives with the...
    Reviewed 31 January 2017
    Everything about this condo was fantastic! The beautiful two bedroom/ two bathroom, spacious, quiet, the large swimming pool and two gas grills which we used often, we will...
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    About this property
    Newly furnished, newly renovated 2BR (one king size & 2 single beds) + convertible sofa bed, 2 Bathrooms 2nd floor condo (sleeps 4-6), and with all the amenities of a comfortable home. Located in White Sands Village with 7 acres of lush tropical surroundings, our air-conditioned condo offers two...
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    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Beachy Chic Condo in Siesta Key - Waterfront - Free wifi - Sleeps 4 !1 / 31
    (11)Very good
    Siesta Key
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
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    • Private Outdoor Pool (Heated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 February 2017
    Thank you for allowing me to rent your beach themed condo. It was more than my expectations. Newly remodeled and furnished. The backyard is flat and offers lots of chaise...
    Reviewed 29 August 2016
    Thank you so much for the chance to stay in your condo. It was clean and had everything we needed for our 5 day stay. Siesta Key is a beautiful beach and we can't wait to...
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    About this property
    Welcome to our Condo in Siesta Key ! Located on the inter-coastal Waterway and a short walk to the whitest sand and the # 1 beach in the USA. This 1 bedroom Condo is a great retreat for anyone looking for a beautiful Island getaway! Our condo is on the 2nd floor (sleeps 4) We are on Siesta...
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    Siesta Key, Florida 34242
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Grand accomdation on USA #1 Beach  - Siesta Key Fl1 / 32
    (1)Very good
    Siesta Key
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Harbor Towers Yacht and Racquet Club Unit 503 provides one of the best views in the building (fifth floor facing south/east). The glass enclosed Lanai with floor-to-ceiling sliding glass doors provides bright sunlight during the morning and afternoon with excellent views of the intercostal water...
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    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Venice
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Satellite TV
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    • Private Garden
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    • Private Outdoor Pool (Heated)
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    NEW POOL AND NEW SCREENED LANAI ARE COMPLETE AND BEAUTIFUL! This three bedroom, two bathroom home has undergone renovation in 2015. The renovation includes a new kitchen with hardwood maple cabinets and granite countertops. The master bathroom remodel includes new cabinetry and all new fixtures,...
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    Location Information
    Venice, Southwest Gulf Coast 34293
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Siesta Key
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Wi-Fi
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 week ago
    The apartment is on the waterway side of the key and is great if you want to fish. The walk to the beautiful beach is only a 10 minute walk away. The apartment is clean and...
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    About this property
    Our condo has just been remodeled with granite counter tops, stainless steel appliances, dishwasher, cabinets, new tile, new bathroom, and new furniture. It is a second floor unit. We have included all the essentials for a family that likes to have the flexibility to make meals at 'home' or...
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    Siesta Key, Florida 34242
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Charming Siesta Key Condo, Walk to Beach, Pool1 / 29
    (5)Excellent
    Siesta Key
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Balcony
    • Wi-Fi
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 weeks ago
    The location is perfect, the beautiful white beach of Siesta Key is on your doorstep. If you feel energetic it is a brisk 25 minute walk into the village from the condominium or...
    Reviewed 10 July 2016
    Very short walk to the beach! Sue is so friendly! The condo was in excellent condition! We will definitely stay here again!
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    About this property
    Spacious Condo on Siesta Key is so centrally located you won't even need a car! 800 square feet, renovated, new, and super clean! King Bed in Bedroom and Sleeper sofa in living room provides 2 separate bed options with spacious closets ready for your things! Screened Lanai (porch). Central AC and...
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    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Lido Key
    1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
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    About this property
    The Bedroom Cottage with an Old Florida feel.The unit has full kitchen, and Queen size bed plus queen size sleeper sofa. The beach is a 6 minute walk and St. Armands 14 minutes, according to Google Maps. The unit has private patio and separate screen porch. The complex has a heated pool. The unit...
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    Location Information
    Lido Key, Sarasota 34236
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 6
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    Venice
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Grill
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    • Internet Access
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A beautiful Florida home close to Manasota beach and within easy reach of a wide range of shops, restaurants and golf courses. This is a tastefully decorated home in the typical Florida style with all the facilities that you need to have the perfect holiday. As you step into the house through the...
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    Location Information
    Venice, Southwest Gulf Coast 34293
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Honeymoon Suite - Gulf views - next to Siesta Key Beach1 / 23
    (5)Very good
    Siesta Key
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    • Air Conditioning
    • Waterfront
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 August 2016
    Me and 2 friends booked this wonderful appoartment very short-term (the day before) and the owner Virginia was just amazing. She helped us with the booking, welcomed us...
    Reviewed 29 March 2016
    The accommodatios are of the highest quality and the location is close enough to enjoy all of what Siesta Keys has to offer without the crowds and noise. One minute walk to...
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    About this property
    Gumbo Limbo Vacation Rentals: Honeymoon Suite, 60 steps to the BEACH. NEWLY REMODELED AND REFURBISHED. Spacious 1 bedroom / 2 full baths townhouse (850sq/ft) over 2 floors, with 1 King size bed, and a luxury Queen self inflating air bed for max. comfort. This townhouse also offers 2 balconies...
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    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 4
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    Siesta Key
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Casual Elegance can best describe this charming 1 Bedroom 1 Bath Villa on world famous Siesta Key Beach. This unit was re-modeled during the summer of 2014 by new owners and offers a crisp clean look and vibe for your vacation escape. The unit received numerous upgrades. Everything in the unit is...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    JUNE SALE! $110/nt; New 2/2 condo! Walk to Siesta Key1 / 25
    (3)Excellent
    Siesta Key
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Wi-Fi
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    • Shared Outdoor Pool (Unheated)
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 May 2017
    My family stayed in this condo for a long wonderful weekend in Siesta Key and it was perfect--just what I was looking for. It's close to everything: beach, grocery stores...
    Reviewed 24 March 2017
    I stayed here with my adult daughter and we both were very impressed with the unit! It was clean, well equipped, and very comfortable. Sue, the owner, made a point of checking...
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    About this property
    All new! This spacious, 2 bedroom/2 bath has everything you need for a relaxing and fun vacation in Sarasota, just minutes to Siesta Key. Relax in comfort with all the amenities: - Fully equipped Kitchen with all new appliances, dishes, glassware, etc. - Top quality, brand new queen size beds -...
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    Location Information
    Siesta Key, Florida 34231
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    WOW Factor Siesta Key Beach Gulf Front Condo in Siesta Dunes on #1 Beach in USA1 / 69
    (8)Excellent
    Siesta Key
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
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    • Ocean Views
    • Housekeeping Included
    • Hot Tub
    • Satellite TV
    • Wi-Fi
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 week ago
    Overlooks pool and also has ocean view. Parking is easy, wifi connected with no issues, access to condo was convenient, and walk to beach is super short.
    Reviewed 1 week ago
    This place is clean, nicely decorated and located on a wonderful beach. Elevator helps in getting in and out, especially with luggage and groceries or for ambulatory folks with...
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    About this property
    Our condo has 1,200 sq ft of living area, two bedrooms and two baths and sleeps 6. 2 twin size Aerobeds for the kids. It is in Building 5 Unit 202- 2nd floor - Elevator in building-laundry facility in building by elevator...just two doors away. The first picture on this website was taken from...
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    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    LUXURY VENICE, FLORIDA GULF COAST HOME1 / 15
    (1)Excellent
    Venice
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Private Outdoor Pool (Heated)
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    • Patio
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 22 June 2015
    This is a wonderful home with a well equipped kitchen. The pool offered swimming and sun bathing on a daily basis. The neighborhood was very friendly and neighbors spoke on a...
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    About this property
    Furnished 3 bedroom, den, 2 bath, two-car garage. Large pool and spa – great entertainment home! Perfectly located in the gated, prestigious Sawgrass community of Venice with views of lakes. Near the championship Waterford, Capri Isles and Calusa Lakes golf courses. Adjacent to a woodland...
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    Location Information
    Venice, Southwest Gulf Coast 34292
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Lido Key
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Golf Country Club in a very quiet luxuriant and preserved vegetation. Easy access to the private fairways. No membership necessary for temporary residents. More than 40 golf clubs within the 20 miles around. Nice 4 bedrooms and 3 bathrooms recently remodeled. Large caged heated new pool. BBQ area....
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    Location Information
    Lido Key, Sarasota 34201
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Gorgeous  Condo Across from Siesta Key Beach1 / 40
    (1)Excellent
    Siesta Key
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Gorgeous 2 bedroom condo across the street from #1 voted beach Siesta Key. We have everything for your home away from home. The beauty of Sarasota will get your attention on your first visit. Siesta Beach is one of the top ranked beaches in the world! Its fine quartz white sand has a silky,...
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    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Quiet and Comfortable Condo Near Turtle Beach1 / 42
    (2)Excellent
    Siesta Key
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • DVD Player
    • Private Outdoor Pool (Unheated)
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 weeks ago
    Do you like sitting on the dock by the bay watching time fade away? We did too! Close to Turtle Beach and free shuttle to Siesta Village/beach. Provided a plan B when the...
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    About this property
    Cozy Cove is a small condominium complex of six total units, located on the south end of Siesta Key in Sarasota, Florida. The complex sits on the Gulf side of the Key along Blind Pass. The complex itself is on the inlet with a dock at the back of the property where you will often see fish jump and...
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    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Siesta Key
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    Siesta Villa Laughing Gull Find yourself in the relaxing comforts of Siesta Villa Laughing Gull. A single-story stand-alone villa, located in the beautiful private community of Polynesian Gardens, on the tropical barrier island of Siesta Key, Fl. The peaceful tranquility of Villa Laughing Gull is...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Siesta Villa Palma - A Mid-Century Escape1 / 21
    (5)Excellent
    Siesta Key
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 November 2016
    We had a great time at Villa Palma. The villa is very clean and it has everything you need for your stay. It is very close to the beach, we ended up only going to the beach. The...
    Reviewed 10 August 2016
    What a LOVELY place to stay!!! Sean was flexible, attentive and accommodating, and there was even fresh fruit, sparkling water and a personalized welcome sign waiting on the...
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    About this property
    Villa Palma is a stand-alone single story villa located in the beautiful Polynesian Gardens community, on the beautiful barrier island of Siesta Key, Fl. The home is chic and hip in its mid-century modern beach cottage decor and style. The newly renovated kitchen is sleek in design and...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Venice
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Nestled between 2 small lakes near Curry Creek Preserve, this beautiful 3-bedroom, 2-bathroom Venice vacation rental house, with room to sleep 6, provides everything you need for an amazing trip. With Venice Beach just 3 miles away and two kayaks at your disposal, you’re in for an unforgettable...
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    Location Information
    Venice, Southwest Gulf Coast 34285
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    PALM'S HOUSE1 / 24
    (1)Excellent
    Siesta Key
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Private Outdoor Pool (Unheated)
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    • Grill
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 June 2015
    As soon as we arrived we knew were going to have a happy stay at Palm's House! Our 5 person party was aged from 16 to 80 and we ALL had a wonderful time! The house itself is...
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    About this property
    Fabulous home on Siesta Key (Sarasota)( two weeks minimum stay ). Just 2 minutes drive to the beach & village. This home features 3 bedrooms and 2 baths with a large kitchen that opens to the family room. Great pool with southern exposure,and enclosed in a screen lanai for mosquito protection...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Siestakey 2bdrm on the beach1 / 22
    (18)Excellent
    Siesta Key
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • DVD Player
    • Secure Parking
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    • Ocean Views
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 20 January 2017
    This was our 6th year staying at Fishermans Cove in Siesta Key, Unit 208, 8900 Blindmans Pass. We become very comfortable during our three weeks in this waterfront condo. The...
    Reviewed 26 June 2016
    This condo was perfect for relaxing beachfront in a beautiful, secluded location. The view was amazing, with the gorgeous gulf beach out back and the bay out front! And the...
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    About this property
    The condo benefits from its own private pool. The living room, master bedroom, and lanai (balcony) all have stunning ocean views. The lanai, with over $10,000 of new doors and windows, is furnished with a table and chairs to enable you to dine al fresco. There is also a comfortable couch to...
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    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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