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Holiday Rentals in Siesta Key

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    Travellers to Siesta Key are booking July dates now. Secure your holiday rental today, and have the perfect trip.
    1 Bedroom, Sleeps 2Quick View
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    Located at the Northwest portion of our resort, this bungalow style resort rental offers one of our closest walks to the beach. The buildings of the 160's are situated in a circle, and offer each of the resort rooms a quiet and private courtyard that is shared with just these specific resort...
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    Siesta Key, Florida 34242
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    1 Bedroom, Sleeps 3Quick View
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    REMODELED - Located right next to one of our two pools, and just down the street from the beach, this unit gives you the option to choose fresh or salt water swimming, or better yet choose both. Enjoy a quick weekend getaway, or come and soak in our beautiful weather for a week or more at our...
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    Siesta Key, Florida 34242
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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    1 Bedroom, Sleeps 4Quick View
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    About this property
    Located at the Northwest portion of our resort, this bungalow style resort rental offers one of our closest walks to the beach. The buildings of the 160's are situated in a circle, and offer each of the resort rooms a quiet and private courtyard that is shared with just these specific resort...
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    Siesta Key, Florida 34242
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    5 of 5 bubbles
    7 Reviews
    3 Bedrooms, Sleeps 6Quick View
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    Pet friendly
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    About this property
    FREE High Speed Wireless Internet ! - just bring your Laptop. Watch the boats float by! Just steps from the Pool, Club House, and picnic area with gas Weber grills. Across the street from Crescent Beach!! Our three bedroom two story townhouse in Gulf & Bay Club Bayside is in a complex of Key...
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    Siesta Key, Florida 34242
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    1 Bedroom, Sleeps 2Quick View
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    TOTALLY REMODELED UNIT - What a gem. When you walk into this resort room you will immediately feel like royalty. Take a look at the photos and you'll quickly realize why this unit is one of our best. As part of our new linen program, this resort rental features quality linens and pillows to ensure...
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    Siesta Key, Florida 34242
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    REMODELED - Less than 1 block to Siesta Key Village, shopping, top restaurants, live music, and entertainment. Walk out of the front door of this fantastic resort room, grab your beach gear and take a short walk to the West and you'll hit the beach, or, walk East and you're in the heart of Siesta...
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    Siesta Key, Florida 34242
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    4.5 of 5 bubbles
    17 Reviews
    1 Bedroom, Sleeps 4Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    1BR (sleeps 4)- Perfect for travelers in search of uncomplicated seclusion. Brought to you by Gertrude Rentals! Located in the most “private” non-private beach neighborhood in Siesta Key, The Old Man and the Sea Inn can accommodate up to 24 guests and is a four unit Key West style home located...
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    Siesta Key, Florida 34242
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    5 of 5 bubbles
    9 Reviews
    2 Bedrooms, Sleeps 6Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Across the street is our Private Access to one of the BEST beaches - Crescent Beach on Siesta Key.Gulf & Bay Club Bayside is a Resort complex of Key West style Town Homes all with one car attached garages. Gulf & Bay Club Bayside offers:* two heated pools* clubhouse with exercise/workout center and...
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    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    1 Bedroom, Sleeps 4Quick View
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    About this property
    This fully remodeled amazing one bedroom ground floor end unit is tiled throughout and has a new A/C unit. If you're looking for a great vacation location on beautiful Siesta Key, then look no further. This people friendly complex is the perfect place for a true couple’s holiday get-away at the...
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    Siesta Key, Florida 34242
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    1 Bedroom, Sleeps 6Quick View
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    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    REMODELED - What a gem. When you walk into this resort rental you will immediately feel like royalty. Take a look at the photos and you'll quickly realize why this resort room is one of our best. As part of our new linen program, this rental unit features quality linens and pillows to ensure a...
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    Siesta Key, Florida 34242
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 6
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    1 Bedroom, Sleeps 3Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    REMODELED - Located right next to one of our two pools, and just down the street from the beach, this unit gives you the option to choose fresh or salt water swimming, or better yet choose both. This King Size Studio with 1 bathroom resort room is truly a home away from home, and it features...
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    Siesta Key, Florida 34242
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    5 of 5 bubbles
    12 Reviews
    2 Bedrooms, Sleeps 4Quick View
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    • DVD Player
    • Satellite TV
    • Patio
    • Wi-Fi
    • Grill
    • Porch
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Newly upgraded ( September 2015 ) with new kitchen, new vanities, newly painted and with the tiles steam cleaned this Siesta Key villa is a gem. It comes with a with a lovely heated community salt water pool and private access to the beautiful white sanded Crescent Beach! Crescent Beach on Siesta...
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    Siesta Key, Florida 34242
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    1 Bedroom, Sleeps 4Quick View
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    Smoking allowed
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    REMODELED RESORT ROOM - Not many hotel rooms on Siesta Key offer what this unit does. This 1 Bedroom and 1 bathroom resort room, part of our luxury Resort Hotel, is truly a home away from home, and it features everything you'll need during your vacation, including: a full kitchen, pots and pans,...
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    Siesta Key, Florida 34242
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    2 Bedrooms, Sleeps 4Quick View
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    • Private Outdoor Pool (Heated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This 1,000 sq. ft., 2 BR, 2 BA unit is located on the ground floor with beautiful views of canal to the intra-coastal waterway. The complex is very well maintained, featuring a heated pool, outdoor whirlpool, a new fishing pier, and the clubhouse has up to date exercise equipment. Siesta Harbor...
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    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    1 Bedroom, Sleeps 2Quick View
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    Pet friendly
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    About this property
    REMODELED - Less than 1 block to Siesta Key Village, shopping, top restaurants, live music, and entertainment. Walk out of the front door of this fantastic resort room, grab your beach gear and take a short walk to the West and you'll hit the beach, or, walk East and you're in the heart of Siesta...
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    Siesta Key, Florida 34242
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    1 Bedroom, Sleeps 4Quick View
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
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    REMODELED RESORT ROOM - This Amazing Resort Room has a Unique floorplan that allows for a King Bed in the Master bedroom, and a pull out Queen sleeper sofa bed in the living room. This is great for friends traveling together, or that extended family vacation. This resort rental is less than 50...
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    Siesta Key, Florida 34242
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    1 Bedroom, Sleeps 4Quick View
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    REMODELED RESORT ROOM - Forget your busy life and come and drift away at our beautiful resort hotel. This 1 Bedroom and 1 bathroom resort style hotel room is truly a home away from home, and it features everything you'll need during your vacation, including a full kitchen, pots and pans, dishes,...
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    Siesta Key, Florida 34242
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    2 Bedrooms, Sleeps 6Quick View
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    • Satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    REMODELED - Oversized Patio, overlooking the courtyard and pool. This resort rental has a birds eye view of this beautiful outdoor courtyard. Forget your busy life and come and drift away on our beautiful resort. This 2 Bedroom and 1 Bathroom Suite is truly a home away from home, and it features...
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    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    5 of 5 bubbles
    12 Reviews
    1 Bedroom, Sleeps 2Quick View
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    • Air Conditioning
    • Waterfront
    • Outdoor Dining Area
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    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our favorite location on Siesta Key, The Siesta Key Village Studio, brought to you by Gertrude Rentals! An accommodating ground floor one-room efficiency apartment perfectly nestled on a quiet tropical street between the best beaches, shopping and dining on the island. Wander one block to your...
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    Siesta Key, Florida 34242
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    1 Bedroom, Sleeps 4Quick View
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    • Parking
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    • Terrace
    • Satellite TV
    • Balcony
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful 1 Bedroom 1 Bathroom vacation home. Gorgeous features and fantastic amenities. Located less than 1/2 Block to the Beach and all the shopping, dining, desserts, and entertainment the Siesta Key Village area has to offer. Soak in the Sun at this beautiful vacation home. The private patio is...
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    Siesta Key, Florida 34242
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    1 Bedroom, Sleeps 6Quick View
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    • Satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    REMODELED RESORT ROOM - This Amazing Resort Room has a Unique floorplan that allows for 2 Full Beds in the Master bedroom, and a pull out Queen sleeper sofa bed in the living room sleeps 6 people. This is great for friends traveling together, or that extended family vacation. This resort rental is...
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    Siesta Key, Florida 34242
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 6
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    1 Bedroom, Sleeps 4Quick View
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    • Internet Access
    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    REMODELED- There is something for everyone here on Siesta Key, and this unit puts you close to it all. Walk out of the front door of this beautifully remodeled resort room and relax on your patio, read a book, watch your kids or grand kids play in the courtyard, or grab your beach gear and take...
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    Siesta Key, Florida 34242
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    2 Bedrooms, Sleeps 8Quick View
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    • Satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    REMODELED - Forget your busy life and come and drift away on our beautiful resort hotel. This Deluxe 2 Bedroom and 1 Bathroom Suite is truly a home away from home, and it features everything you'll need during your vacation, including a full kitchen, pots and pans, dishes, cups, utensils, WIFI, HD...
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    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 8
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    1 Bedroom, Sleeps 4Quick View
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
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    REMODELED RESORT ROOM - The beach, shopping, dining, entertainment, and a daquiri within walking distance. What more could you ask for? This 1 Bedroom and 1 bathroom resort room is a great place to kick off your sandals and relax. It features a Full size bed, a Twin size Day bed, and Twin sleeper...
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    Siesta Key, Florida 34242
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    • Parking
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    • Private Outdoor Pool (Heated)
    • Private Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Escape to your own secluded tropical oasis. Lush island landscaping surrounding the property makes this home a unique and private setting. Private dock on protected cove 2 minutes from Sarasota Bay/ICW. Rent a boat at neighboring marina if you choose. Breathtaking large private pool, with numerous...
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    Siesta Key, Florida 34242
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    2 Bedrooms, Sleeps 5Quick View
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    • Air Conditioning
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    • Children's Pool
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Cancellation opens up part of April 2017! Spend your Easter on beautiful Siesta Key! Act fast, affordable rentals are going quick! Resort Style Vacationing -- Live the dream! Voted number one beach in the USA! 2 Week Minimum Rental Required. A very tastefully decorated 2 bedroom 2 bath 4th floor...
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    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    4.5 of 5 bubbles
    10 Reviews
    2 Bedrooms, Sleeps 4Quick View
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    • Patio
    • Washer
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    • DVD Player
    • Wi-Fi
    • Grill
    • Satellite TV
    • Porch
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Newly upgraded ( September 2015 ) with new kitchen, new vanities, newly painted and with the tiles steam cleaned this Siesta Key villa is a gem. It comes with a with a lovely heated community salt water pool and private access to the beautiful white sanded Crescent Beach! Crescent Beach on Siesta...
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    Siesta Key, Florida 34242
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    1 Bedroom, Sleeps 4Quick View
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    Smoking allowed
    About this property
    REMODELED RESORT ROOM - Location, location, location. Forget your busy life and come and have some fun in our Amazing Beach Resort Hotel. Our Deluxe 1 Bedroom and 1 bathroom resort rooms are truly a home away from home, and they feature everything you'll need during your vacation. Each resort room...
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    Siesta Key, Florida 34242
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    4 Bedrooms, Sleeps 10Quick View
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    About this property
    This wonderful home will be going though a complete renovation that will include adding an additional 2 bedrooms and 1 bathroom, which will make this home a 4 bedroom 3 bathroom home - with one of the bedrooms functioning as a bunk room. The Exterior covered deck will become interior living space...
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    Siesta Key, Florida 34242
    Condo/Apartment - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    5 of 5 bubbles
    7 Reviews
    2 Bedrooms, Sleeps 6Quick View
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    • Ocean Views
    • Housekeeping Included
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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our Fisherman's Cove condo description Paradise awaits - GORGEOUS, totally renovated in 2016, two bedroom, beach front condo on the Gulf of Mexico with sunset views overlooking the and sunrise views of the lagoon, expansive water views from every window. Beach was restored so it is large...
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    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, Sleeps 5Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    Enjoy all that Siesta Key has to offer without the astronomical prices and cramped quarters of a beach condo. Take your pets and have the grandkids visit without worry because this family friendly, home will allow you to host with comfort and with confidence. Located on a private street in a...
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    Siesta Key, Florida 34242
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    1 Bedroom, Sleeps 6Quick View
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    About this property
    REMODELED RESORT ROOM - This Amazing Resort Room has a Unique floorplan that allows for 2 Full Beds in the Master bedroom, and a pull out Queen sleeper sofa bed in the living room sleeps 6 people. This is great for friends traveling together, or that extended family vacation. This resort rental is...
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    Siesta Key, Florida 34242
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 6
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    1 Bedroom, Sleeps 4Quick View
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    • Internet Access
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    • Satellite TV
    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    REMODELED- There is something for everyone here on Siesta Key, and this unit puts you close to it all. Walk out of the front door of this beautifully remodeled resort room and relax on your patio, read a book, watch your kids or grand kids play in the courtyard, or grab your beach gear and take...
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    Siesta Key, Florida 34242
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    4 of 5 bubbles
    2 Reviews
    1 Bedroom, Sleeps 4Quick View
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    • Waterfront
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    • Grill
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    • Balcony
    • Satellite TV
    • Patio
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Not owned by Gumbo Limbo: This remodeled cottage of 733 square feet is waiting to win you over with its abundant charm and tasteful interior. This exquisite townhouse features 1 bedroom with a Queen sized bed and 2 full baths; also, there is a Murphy bed which can be pulled down in the lounge...
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    Siesta Key, Florida 34242
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 4
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    Beautiful 2/2 condo conveniently located near the Captain Curt Village and across the street from the number one beach in the USA! 1 Week Minimum Rental Required. A very tastefully decorated 2 bedroom 2 bath 3rd floor unit in the very desirable Bay Oaks located on the voted #1 Beach in the USA,...
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    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, Sleeps 4Quick View
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    Totally renovated adorable Siesta Key bungalow nestled on a shaded street just minutes from Siesta Key beach and the village of Siesta Key with a variety of shops, restaurants and nightlife. Drive into the circular driveway and park your car under the covered parking to be away from the 10 minute...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    5 of 5 bubbles
    2 Reviews
    4 Bedrooms, Sleeps 8Quick View
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    Very spacious, air-conditioned 4 bed detached ranch-type Villa on Siesta Key Bayside. Sleeps 8, 1 King, 1 Queen, 2 Full and 2 twin beds. 1 month minimum Jan-March, 2 week minimum April -Dec. Maximum 3 cars . Large Heated Communal pool, Own Outdoor patio area with BBQ , Table, seating and sun...
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    Siesta Key, Florida FL34242
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    1 Bedroom, Sleeps 4Quick View
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    REMODELED - HANDICAP ACCESSIBLE - Very Large 1 Bedroom Suite - Forget your busy life and come and drift away on our beautiful resort. Located right next to one of our two pools, and just down the street from the beach, this unit gives you the option to choose fresh or salt water swimming, or...
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    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    3 Bedrooms, Sleeps 10Quick View
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    • Balcony
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    Smoking allowed
    About this property
    Beachfront Townhome in Siesta Key Village Area. Located on Sunset Point, directly on the beach, this Vacation Home has it all. Walk out of your front door or single car garage, and directly on to the pearly white sands of Siesta Key. This 3 bedroom 3 bath home has one of a kind views from mulitple...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 10
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    4 Bedrooms, Sleeps 8Quick View
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    • Private Outdoor Pool (Heated)
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    • Private Garden
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    Pet friendly
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    Smoking allowed
    About this property
    Our 2000 sq ft beautifully renovated 4 bedroom home features a private pool with patio seating and a new Weber BBQ with cast iron grills. The house has been outfitted with new, transitional solid wood furniture throughout including brand new premium mattresses and pillows in every room. The home...
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    Siesta Key, Florida 34231
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    1 Bedroom, Sleeps 4Quick View
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    REMODELED HONEYMOON SUITE - Whether you and your loved one are Getting Married, just wanting a private weekend getaway, or you're a family that needs a more spacious 1 bedroom and 1 bathroom luxury resort room option, this absolutely stunning resort rental will meet your needs. Its our largest...
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    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    REMODELED - Forget your busy life and come and drift away on our beautiful Resort Hotel. This tastefully remodeled 1 Bedroom and 1 bathroom resort room is truly a home away from home, and it features everything you'll need during your vacation, including a full kitchen, pots and pans, dishes, cups,...
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    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    2 Bedrooms, Sleeps 6Quick View
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    UNDER CONSTRUCTION - UPDATED PICS COMING SOON. What a gem. When you walk into this resort rental you will immediately feel like royalty. Take a look at the photos and you'll quickly realize why this unit is one of our best. As part of our new linen program, this rental unit features quality linens...
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    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    3 Bedrooms, Sleeps 6Quick View
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    • Washer
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    Pet friendly
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    About this property
    Turtle beach was just re-nourished in March 2016!! Come enjoy the great new beach at Fisherman's Cove! 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. (all new photos -just uploaded!) Our ground-level...
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    Siesta Key, Florida 34242
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    5 Bedrooms, Sleeps 14Quick View
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    • Balcony
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beachfront Townhome in Siesta Key Village Area. Located on Sunset Point, directly on the beach, this Vacation Home has it all. Walk out of your front door or single car garage, and directly on to the pearly white sands of Siesta Key. This 5 bedroom 4 bath completely remodeled home has one of a kind...
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    Siesta Key, Florida 34242
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 14
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    2 Bedrooms, Sleeps 6Quick View
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    About this property
    REMODELED - Ground floor with a Patio area, a pool and courtyard view, perfect weather and a short walk to the best beach in America or Siesta Key Village. This is resort room features 2 Bedrooms and 1 Bathroom. This beach resort room is perfect for a quick get away or an extended stay. It is truly...
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    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    4.5 of 5 bubbles
    3 Reviews
    1 Bedroom, Sleeps 4Quick View
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    Kid friendly
    Smoking allowed
    About this property
    Only 60 steps to #1 most beautiful Beach in the nation – SIESTA KEY PUBLIC BEACH -. Spacious newly remodeled 1 bedroom studio apartment with (580sq/ft) ground floor, 1 King size bed and a luxury self inflating Queen air bed for max comfort. The bathroom offers a walk-in rain-forest shower. The...
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    Siesta Key, Florida 34242
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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