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Holiday Rentals in Sarasota, FL

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    Travellers to Sarasota are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    1 / 25
    4 of 5 stars (2) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    1 / 7
    3 of 5 stars (1) Average
    Lido Key
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    1 / 14
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    1 / 19
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    About this property
    Home located minutes from everything Sarasota has to offer. 6 miles from Siesta Key Beach. 1.5 miles to downtown, 4.5 miles the Lido Beach and St. Armand's Circle, and walking distance to Sarasota Memorial Hospital. Myakka State Park is about a 25 minute drive. The home is a 3 bedroom, 2 bathroom... View all property information
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    Sarasota, Southwest Gulf Coast 34239
    1 / 32
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    * Please inquire about availability before booking * <BR>* Sales tax is 12% (7% for Florida and 5% for Sarasota County) and is not included in the rental rate. <BR><BR>Welcome to the Cosentino homestead! Settle into this serene, natural paradise in the middle of a bustling city. Nowhere else will... View all property information
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    Sarasota, Southwest Gulf Coast 34231
    1 / 26
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    A stone's throw from beautiful Lido Beach near downtown Sarasota, our cheery yellow house incorporates 3 entirely separate units - 1 x 2 bedroom, 1 x 1 bedroom and 1 studio apartment. This listing is for the front unit, a large, bright and private two bedroom apartment with queen beds and a large... View all property information
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    Sarasota, Southwest Gulf Coast 34236
    1 / 18
    5 of 5 stars (1) Excellent
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    Our cottage is located about 8 Minutes to Siesta Key. Enjoy our beautiful studio with a a full large kitchen, living room, and bathroom. Beautiful lani with plenty space to enjoy the large grounds. Shopping, Movies, Gyms and more are just steps away. This is a large property where you can enjoy... View all property information
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    Sarasota, Southwest Gulf Coast 34231
    1 / 15
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    Condo Description<BR><BR>This Siesta Harbor Condo is a larger end-unit on the first floor of the Siesta Harbor Dolphin building with additional windows facing East and a hurricane proof lanai enclosure with screens overlooking the Yacht-Harbor turning basin. Covered parking for your car is... View all property information
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    Sarasota, Southwest Gulf Coast 43232
    1 / 16
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    About this property
    Delightful studio apartment tucked away on exciting Lido Key. Nestled amid a tropical garden, the units are steps from the beautiful white sands of Lido beach, with the turquoise waters of the Gulf of Mexico just beyond. The beach is a 6 minute walk and St. Armands 14 minutes, according to Google... View all property information
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    Sarasota, Southwest Gulf Coast 34236
    1 / 11
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Relax in a traditionally furnished Floridian style home. Our villa can accommodate up to six people, 2 King's and 1 Couch that unfolds into a bed. The living room has a TV with a basic cable. There is free WiFi internet connection for all guests. The dining room table seats 6 adjoining the open... View all property information
    Location Information
    Sarasota, Southwest Gulf Coast 34232
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    1 / 23
    4 Bedrooms, 4 Bathrooms, Sleeps 9 | Quick View
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    About this property
    Perfectly located, NEW, 4 bedrooms 4 1/2 bathrooms private home, in a gated community, combines luxury with convenience of location. We offer you a large 4000sf+ home within a short distance to the pristine beaches of Siesta Key and walking to the Village, Restaurants, shops and nightlife. Privacy... View all property information
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    Sarasota, Southwest Gulf Coast 34242
    1 / 20
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    Single house on private garden (sunbathe chairs )Large terrace with pergola, barbecue.(Garage not available). 2 bicycles. Inside : Kitchen with dishwasher,electric oven,microwave. all appliances and dishes. Washer and dryer. Lounge with 2 sofa,working fire place,TV,DVD,WIFI Main bedroom with... View all property information
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    Sarasota, Southwest Gulf Coast 34234
    1 / 32
    4 of 5 stars (1) Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    Adorable Luxury Cottage on Gulf front Estate, nestled among Oaks & Palms. Tongue and groove wood cathedral ceiling, white wood floors, wains-coat, tile bathroom, washer, dryer and dishwasher. Large sliding glass doors to enjoy a view of gardens & ponds. Located on two beautiful landscaped acres... View all property information
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    Sarasota, Southwest Gulf Coast 34242
    1 / 21
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    Luxury home on 27 hole golf course, 3400 sq ft of designer heaven PLEASE NOTE, RATES ARE CALCULATING INCORRECTLY PLEASE CONTACT OWNER FOR QUOTE FOR JUNE/JULY BOOKINGS. This newly furnished and updated executive home totals over 3400 sq ft of luxury right on the 1st fairway of the #1 rated golf... View all property information
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    Sarasota, Southwest Gulf Coast 34201
    1 / 16
    1 of 5 stars (1) Terrible
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Balcony
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    About this property
    Voted best Outsider Architecture in 2013 by Sarasota Magazine and called “the most picturesque building in town.” Get swept away by old Sarasota while enjoying our location at the heart of the newest restaurants, galleries, theatres, and shops Sarasota’s art and business districts have to offer.... View all property information
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    Sarasota, Southwest Gulf Coast 34236
    1 / 37
    5 of 5 stars (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    This beautifully decorated Beach House of about 1400 sq ft includes a living room, dining room, equipped kitchen, laundry room, 2 bedrooms, and 2 bathrooms. The living room has a large and comfortable couch, a coffee table, and cable TV. The dining room includes a dining table for 6, and a small... View all property information
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    Sarasota, Southwest Gulf Coast 34236
    1 / 46
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    About this property
    Located in a quiet family neighborhood just minutes to shopping, dining, golf courses and of course the #1 Beach in the USA along with multiple other beautiful beaches including Lido Key, Casey Key, Turtle Beach and more. This is a 1000 square foot newly renovated two bedroom apartment with 1 car... View all property information
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    Sarasota, Southwest Gulf Coast 34232
    1 / 12
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    Delightful 1 bedroom apartments tucked away on exciting Lido Key, the Lido Islander located at 528 South Polk Drive, Sarasota, FL 34236. Nestled amid a tropical garden, the units are steps from the beautiful white sands of Lido beach, one of the top 25 beaches in the United States according to... View all property information
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    Sarasota, Southwest Gulf Coast 342362037
    1 / 28
    4 of 5 stars (1) Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • ?
    • ?
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    • x
    About this property
    Great private cozy apartment with a nice outdoor terrace / bbq area Located in a quiet family neighborhood just minutes to shopping, dining, golf courses and of course the #1 Beach in the USA along with multiple other beautiful beaches including Lido Key, Casey Key, Turtle Beach and more. This is... View all property information
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    Sarasota, Southwest Gulf Coast 34232
    1 / 22
    5 of 5 stars (1) Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 9 | Quick View
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    About this property
    The home has a great floor plan.2,064sq ft of internal space. Lovely breakfast table at the side of the kitchen, overlooking deck & pool. For more formal occasions separate large dining area. Love to BBQ. we provide gas BBQ on the patio, large table for alfresco dining.The large patio has sun &... View all property information
    Location Information
    Sarasota, Southwest Gulf Coast 34238
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    1 / 18
    3 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    About this property
    Beautiful 3 bedroom 3 bath home. Ideally located steps from St Armands Circle shops and restaurants and minutes from downtown Sarasota. Walk to famous Lido Key beach. Professionally designed, furnished and outfitted. Lush landscaping surrounds outdoor pool and seating areas behind privacy wall.... View all property information
    Location Information
    Sarasota, Southwest Gulf Coast 34236
    1 / 17
    Studio, 1 Bathroom, Sleeps 3 | Quick View
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    1920's mixed-use building in historic area that is nestled between high-end residential neighborhoods. The studio apartment is super nice, safe and secure in a quaint shopping/theater area and walking distance to marina, fishing, supermarkets, transportation, theaters, opera, library, parks and... View all property information
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    Sarasota, Southwest Gulf Coast 34236
    1 / 34
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    • ?
    • ?
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    • x
    About this property
    Great private cozy apartment with a nice outdoor terrace / bbq area Located in a quiet family neighborhood just minutes to shopping, dining, golf courses and of course the #1 Beach in the USA along with multiple other beautiful beaches including Lido Key, Casey Key, Turtle Beach and more. This is... View all property information
    Location Information
    Sarasota, Southwest Gulf Coast 34232
    1 / 25
    5 of 5 stars (13) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    About this property
    Enjoy the ultimate vacation in our luxury villa situated in the award winning, exclusive & secure University Park Country Club. Bright & airy home all tastefully furnished. Extremely well equipped - cycles, LCD TVs, wifi, mini office, juicers, bread maker, Nutribullet, etc. A perfect spot for... View all property information
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    Sarasota, Southwest Gulf Coast 34201
    1 / 15
    2 Bedrooms, 3 Bathrooms, Sleeps 4 | Quick View
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    About this property
    **CALENDAR IS KEPT UP-TO-DATE!** You will have no excuse not to relax when you walk-out onto the lanai and watch the boats and dolphins go by. Walk down the steps to the fishing pier, grills, and lush green gardens to soak up the fresh air. Bay Oaks is located on the InterCoastal Waterway with... View all property information
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    Sarasota, Southwest Gulf Coast 34242
    1 / 9
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    Clean, quiet private suite with oversized bathroom. Five minute drive to Siesta Key and just a few miles from all the beaches on the key. We have several shops and amazing restaurants within walking distance of the house. Also located nearby; bus stop, Publix grocery and liquor store, national... View all property information
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    Sarasota, Southwest Gulf Coast 34231
    1 / 25
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    About this property
    This newly renovated two bedroom one bath apartment, in a 4 family house will bring you all a joy that you will need for your next vacation trip. Not even a minute away from Siesta Key we are conveniently located on Siesta Dr. Fully furnished, equip with free WIFI, Tv and so much more. Sarasota... View all property information
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    Sarasota, Southwest Gulf Coast 34239
    1 / 19
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    SARASOTA FLORIDA GATED COMMUNITY OF VILLAGIO, BEAUTIFUL 3/2 CONDOMINIUM... Professional on site management and security with many amenities. This is one of very few 3 bedrooms 2 bath units with 1,247 total square feet and covered parking. This is a second story (about 18 steps) corner unit, with... View all property information
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    Sarasota, Southwest Gulf Coast 34237
    1 / 22
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Here is - the one of Sarasota's most up-and-coming areas, lies a sanctuary of tranquility, harmony and belonging – “Serenata”. That unique private gated community offers you a resort lifestyle in a uniquely designed community with exquisite lake views, elegant residences and abundant recreation.... View all property information
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    Sarasota, Southwest Gulf Coast 34243
    1 / 24
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    About this property
    4/5 Bed Rooms, 3 Baths, Sleeps 8 to 12<BR><BR>Very elegant, updated, 4br, 3 ba, heated pool home, in the heart of Sarasota, close to every thing, down town, beaches, lido key, St Armand cir, marina jacks, gulf courses, museums .<BR><BR>The house is fully renovated and updated, elegantly furnished... View all property information
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    Sarasota, Southwest Gulf Coast 34237
    1 / 22
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    This Beach Cottage has it all! Plenty of space for your friends and family and is located just steps from the World Famous Siesta Key Public Beach. This spacious Cottage has 4-5 available bedrooms and a fenced in backyard with propane grill. This house is ready for your next Siesta Key get... View all property information
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    Sarasota, Southwest Gulf Coast 34242
    1 / 14
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    We are in the heart of historic Burns Square in downtown Sarasota, nestled between high end residential neighborhoods S. Palm Avenue, Laurel Park and Hudson Bayou. You do not need a car as we are in walking distance to amenities and entertainment such as Comedy Clubs, Opera, Performance Theaters,... View all property information
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    Sarasota, Southwest Gulf Coast 34236
    1 / 19
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    About this property
    Escape to beautiful Sarasota in this charming, tropical condo. The Unit has been refurbished with new bathrooms and new floors throughout. It is tastefully decorated in bright colors with stylish, comfortable furnishings. An airy porch adds to your enjoyment. The complex is impeccably... View all property information
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    Sarasota, Southwest Gulf Coast 34232
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    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    About this property
    Moomist Villa is an idyllic setting to relax and rewind. It is located within Polynesian Gardens across the street from beautiful Siesta Key beach (Number 1 on the list of Top 10 most beautiful beaches in the USA). Out the front door you have a “peek-a-boo” view of the bay with boats cruising by.... View all property information
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    Sarasota, Southwest Gulf Coast 34242
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    Sunny, Bright and Breezy Quiet Island Retreat nestled in a Lush Tropical Garden Courtyard awaits your arrival. Professionally decorated, our 2 Bed, 2 Bath Condo getaway gives you Peaceful Island Paradise. Located on a Tranquil Waterway with Gorgeous Views on the Gulf Side, with Private, Boat Dock... View all property information
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    Sarasota, Southwest Gulf Coast 34242
    1 / 8
    4 of 5 stars (2) Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    Come visit paradise. Our vacation home is comfortable, decorated in the colors blue, green and white. It is very clean with a tiled, enclosed lanai. The bedroom is cozy with a big closet and storage. The bathroom is small but efficient. We have two televisions, a DVD player, internet and... View all property information
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    Sarasota, Southwest Gulf Coast 34240
    1 / 6
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    3 BEDROOM/3 BATH OCEANFRONT VILLA AT THE BEAUTIFUL HYATT SIESTA KEY RESORT AVAILABLE SEPTEMBER 6 - SEPTEMBER 10 (4 NIGHTS) $1200 FREE PARKING AND CONTINENTAL BREAKFAST INCLUDED This beachfront condo hotel is 3.9 miles from the Country Club of Sarasota and 6.2 miles from I-75. Upscale 2-bedroom... View all property information
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    Sarasota, Southwest Gulf Coast 34242
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    This newly renovated pet friendly mediterranean home features a large fenced in back yard with patio area. The large open concept kitchen features all stainless steel appliances and quartz counter tops. Oversized washer and dryer make it convenient to do laundry quickly! Master suit features a... View all property information
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    Sarasota, Southwest Gulf Coast 34239
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    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    Sarasota Condo Rental Photos and Description Condo, 1 Bedrooms, 1 Baths, 4 Sleeps This Spanish Mediterranean condominium complex sits right in front of the intracostal waterway and is only minutes walk to the #1 beach in the United States on Siesta Key. The complex has bright white stucco with... View all property information
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    Sarasota, Southwest Gulf Coast 34231
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    Enjoy easy access to the #1 rated beach in the US, but relax in a quiet and cozy setting. This 2/2 cottage features a fully stocked and updated kitchen with granite and stainless steel appliances. Tile floors throughout. Relax on the new patio under the shade of the towering Melaleuca trees. Master... View all property information
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    Sarasota, Southwest Gulf Coast 34231
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    1 Bedroom, 1 Bathroom, Sleeps 6 | Quick View
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    Private suite/guest home- Our neighborhood is an established, safe, blended community. Surrounded by mature oak trees, ponds, covered bridge and walking paths make it unique and quaint. Our guest home is 1 bedroom with a comfortable queen size sterns & foster mattress. The Oversized great room has... View all property information
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    Sarasota, Southwest Gulf Coast 34235
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    Lido Key
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    Lido Shores Vacation Rental available starting May 15, 2016. This beautiful unit is located just a short walk to St. Armand’s Circle with loads of shopping and dining choices and Lido beach to enjoy the beautiful Florida weather. Unit provides everything needed to enjoy your stay. Unit features... View all property information
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    Lido Key, Sarasota 34236
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    This wonderful pool home is located in the heart of Sarasota and just minutes away from the world-famous Siesta Key Beach! This fantastic vacation home offers 4 relaxing bedrooms and 3 full baths - there is also a Queen-size pull out sofa in the living room. A real bonus is having two master... View all property information
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    Sarasota, Southwest Gulf Coast 34241
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    Lido Key
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    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.... View all property information
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    Lido Key, Sarasota 34201
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    Want to relax? ... or ... an action packed, fun-filled stay? ... or ... a little of both? Then come stay at our Vintage Grand Condo where you can experience resort style living. It's the perfect place to call home, if only for a little while. The condo has two bedrooms, two baths, full kitchen,... View all property information
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    Sarasota, Southwest Gulf Coast 34238
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    5 of 5 stars (2) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    Stunning Siesta Key home on Crescent Beach by the Point of Rocks with private beach access. 3 bedroom 3 bath with 2 full kitchens,fireplace and 2 car garage, private jacuzzi on patio and a heated community pool. 3 flat panel tv"s with DVD and full surround sound in living room and netflix. Can be... View all property information
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    Sarasota, Southwest Gulf Coast 34242
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    Let this gorgeous Sarasota vacation rental condo serve as your ultimate home-away-from-home during your stay in sunny Florida! Nestled on Siesta Key mere steps away from a fishing pier on the intracoastal waterway, this delightful condo has everything you want for your next getaway. This... View all property information
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    Sarasota, Southwest Gulf Coast 34242
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    Quaint two-bedroom two-bathroom condo at Castel del Mare. Castel is a small complex located on the inter-coastal side of Siesta Key and walking distance to Siesta Key beach, consistently voted the #1 Beach in the United States. The location is perfect for the beach and also easy access to all... View all property information
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    Sarasota, Southwest Gulf Coast 34231
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    3 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    The maintenance free community of the Isles offers resort lifestyle amenities with a great Sarasota location. Located just minutes from Siesta Key Beach on Palmer Ranch, this is really a place where you can have it all. Meticulously-kept single-family home built by DiVosta, the Isles community... View all property information
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    Sarasota, Southwest Gulf Coast 34238
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    You will love our beautifully maintained and clean Villa Youppie in Sarasota. It is located at the corner of a lake which provides lots of privacy and thanks to a southern exposure you have sun in the pool and on the patio all day long. New travertine tiles on the patio, granite counter tops in the... View all property information
    Location Information
    Sarasota, Southwest Gulf Coast 34238