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Holiday Rentals with Pools in Siesta Key

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    Travellers to Siesta Key are booking February dates now. Secure your holiday rental today, and have the perfect trip.
    714 Matching Rentals in Siesta KeyView all 901 rentals
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    Gulf Side Siesta Key Villa~Peaceful 1st Floor Villa, 3 pools-Jamaica Royale #1001 / 47
    (4)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Jamaica Royale #92 on the #1 Beach in the USA!1 / 12
    (4)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Beachfront Getaway in Siesta Key1 / 28
    (17)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Fido Friendly, Saltwater Pool, Only 1 mile to SK Beach, Close to the Village, Sh1 / 42
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Private Outdoor Pool (Unheated)
    • Grill
    • Air Conditioning
    • Cable/satellite TV
    • Wi-Fi
    • Patio
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 September 2018
    The house was beautiful and very spacious. Great proximity to the beach and town center, and the kids loved Glebe Park, which was located a short walk down the street. We are...
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    About this property
    On Siesta Key we offer a high-end gorgeous, Fido friendly, Key West style 3 bedroom, 2.5 bath custom home. Desire a private saltwater heated pool while vacationing on Siesta Key? Then this vacation home will be your home away from home in tropical paradise…..just minutes from the village and...
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    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Balcony
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Wi-Fi
    • Grill
    • Washer
    • Patio
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Light, bright & airy, and facing west over the beach - directly in front of one of the best beaches in the world. Siesta Key Beach has quartz sand that never gets hot and is famous for making the most spectacular sand sculptures. Come and try your hand at creating a sand masterpiece, enjoy...
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    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • Grill
    • Cable/satellite TV
    • Hot Tub
    • Washer
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Vacation on Siesta Key in this newly built 4 bedroom custom pool & spa home just a 600 ft. away from Shell Beach. Across the street and down the small drive is the gulf. Shell Beach has a very small sandy beach. It's on Big Pass and looks out to Lido Key. Here the water has a current so little...
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    Siesta Key, Florida 34242
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Newly Renovated & Modern, Wifi, Gulf Facing Harbor Towers, 3 bedroom with den1 / 36
    (1)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Patio
    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    • Grill
    • Washer
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 22 January 2018
    What an amazing property! Everything is brand new. Condo is equipped with everything you could possibly want/need! Loved that everything we needed for the beach was provided...
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    About this property
    Newly remodeled, modern and beautiful 3 bedrooms, plus a den, 3 full bath condo right on Siesta Key, in a complex overlooking the intracoastal waterway and close to the beach!! Fabulous powdery white sands of Siesta Key Beach are just a short stroll away!! You won't be disappointed! Take a look...
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    Siesta Key, Florida 34242
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Patio
    • Grill
    • Air Conditioning
    • Washer
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy an incredible sunset on Siesta Key's Crescent Beach and walk back to your private villa on Siesta Key in Polynesian Gardens. Plan your get-a-way at our two bedroom, two bath villa where you have a screened-in lanai looking into the grassy back yard with your own personal BBQ grill. The...
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    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Siesta Key Condo w/Private Beach Access, Wifi Included,  Heated Pool, Tennis & B1 / 36
    (4)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • DVD Player
    • Washer
    • Air Conditioning
    • Grill
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 March 2018
    Loretta's place was clean, comfortable, and beautifully kept. It's on the second story with private balcony and a short walk to the beach and an even shorter walk to a nice pool...
    Reviewed 12 March 2018
    Condo was very comfortable, great location, Nice view from balcony. Complex was well-maintained resort like on the bay. Owners were always available to speak with any hours...
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    About this property
    Step out onto your private balcony and watch the boats docked in a small cove just off the intercoastal. - Completely redone 2 bedrooms, kitchen, baths, living room in a beautiful beach theme with predominantly white colors with pops of turquoise, teal and calming sea blue. - Enjoy...
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    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Balcony
    • Cable/satellite TV
    • Patio
    • Washer
    • Shared Outdoor Pool (Unheated)
    • Terrace
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Be the first to book this brand new completely remodeled unit right across the street from the Best Beach in the USA - Siesta Beach. You have a view of the gulf across the street from this beautifully and lovingly renovated condo with everything done with the most discriminating guest in mind....
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    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Sandy Toes Siesta Key Florida  (6796)1 / 40
    (23)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
    • Cable/satellite TV
    • DVD Player
    • Air Conditioning
    • Patio
    • Waterfront
    • Washer
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 April 2018
    Everything was great. The condo was updated, clean and spacious. It had what we needed to really enjoy our week. It was a quick walk to the beach, restaurants and shops. We...
    Reviewed 25 March 2018
    We had so much fun. It was so nice that the kids had their own space , own TV, own bathroom. The beach is amazing. The owner provided beach towels, chairs and umbrellas. I...
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    About this property
    A spacious 2 bedroom 2 bath Townhouse, with a 2 car garage and extra guest parking. Stroll down a private road (about 300 yards) to the #1 Beach in the U,S. You are in the Resorts of Sara Sea and just a couple of blocks from restaurants, grocery, sports rentals and ice cream ! The Great room has...
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    Siesta Key, Florida 34242
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Siesta Key -  2bdrm on the beach - amazing views!!1 / 27
    (29)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • DVD Player
    • Secure Parking
    • Washer
    • Cable/satellite TV
    • Wi-Fi
    • Air Conditioning
    • Ocean Views
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 July 2018
    Our stay was just fantastic! Loved every minute and the condo was perfect for RNR! I will recommend the condo without hesitation. Husband and daughter loved to fish off the...
    Reviewed 11 July 2018
    Our trip was absolutely wonderful!! The owners were very accommodating and quickly responded to any questions. We will definitely be back!!!
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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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    Bay Views - Private access to Beach. Enjoy Tennis, Heated Pools, Fishing1 / 50
    (12)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Waterfront
    • Wi-Fi
    • Grill
    • DVD Player
    • Washer
    • Sauna
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 December 2017
    Beautiful beach and spacious condo with all amenities at your doorstep, enjoyed tennis , pool and exercise room and outdoor gas grill right across street yet still very private...
    Reviewed 20 November 2017
    We had a wonderful vacation stay in this condo. It was spacious, clean and had beautiful views of the waterway. We really enjoyed having our morning coffee watching the boats go...
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    About this property
    Gulf & Bay Club Bayside is a gated resort community is across the street from our private access to - Siesta Key Beach with the world renowned white sands - rated one of the top ten in the US! FREE High Speed Wireless Internet ! - just bring your Laptop. Watch the boats float by! Just steps from...
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    Siesta Key, Florida 34242
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Canal Home on Siesta Key w/ Pool, Wifi, Renovated 1950 Style Sarasota School of1 / 36
    (1)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Patio
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 weeks ago
    This house is perfect for your Siesta getaway!Close to Village and #1 beaches great pool on the CanalI would defiantly stay here again!
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    About this property
    You will Never Want to Leave this Upscale, Mid-Century Modern, 4 bedroom Pool home with Salt-Water Canal Views and Boat Dock on Siesta Key!!! This unique 1950's built, partially renovated, 4 bedroom, 3 full bath, 'Sarasota School of Architecture style' pool home is conveniently located...... only...
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    Siesta Key, Florida 34242
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • DVD Player
    • Cable/satellite TV
    • Wi-Fi
    • Washer
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Balcony
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    New furnishings complete an already fabulous condo! Enjoy this newly painted, newly furnished adorable & quaint ground floor two bedroom, one bath condo with water views and all of the amenities you are looking for in a fun yet relaxing atmosphere. This particular unit is located only about 30...
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    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Beachfront- Gulf View! 2 BR/BA Crescent Arms 603S, #1 Beach in the US.1 / 24
    (9)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Wi-Fi
    • Air Conditioning
    • Cable/satellite TV
    • Waterfront
    • DVD Player
    • Washer
    • Ocean Views
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 March 2018
    Such a well appointed condo, with a fabulous location right on the beach.Easy walking distance to some great restaurants. Our owner was very attentive and answered all...
    Reviewed 14 November 2017
    We loved this condo. The beach was wonderful. Siesta Key Village was so close with great restaurants to choose from... Pavan was very nice to work with. What more can you ask...
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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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    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    • Washer
    • Air Conditioning
    • Patio
    • Cable/satellite TV
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Got Paradise!? Well now you do..... This oasis on Siesta Key is just that. The condo is only a couple of blocks away from the beach and rests in Siesta Key Village where you will find lots of great dining, amazing shops, coffee houses and more, all a short walk away. With everything you could...
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    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Washer
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Grill
    • Patio
    • DVD Player
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Walk to Crescent Beach! This is a darling 2 bedroom, 1 bath updated and newly furnished condo in the very popular Bay Oaks on Siesta Key, Florida. The amazing amenities include access to a private fishing pier, private tennis court, billiard room, clubhouse, BBQ area, sauna, a heated swimming...
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    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Heated Pool w/ Short Walk to Beach, Renovated & Updated, Fishing Pier, Tennis, L1 / 38
    (3)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Patio
    • Cable/satellite TV
    • Washer
    • Air Conditioning
    • Grill
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 weeks ago
    We had a great stay here! Super easy check-in process with an access code, and the condo has a nice pool and close access to the beach. The unit itself was very comfortable and...
    Reviewed 8 November 2018
    This condo is very relaxing, great beach vibe, TV's in each room with balcony over looking the pool. The Kitchen and bathrooms are updated and very nice. Easy walk to Siesta...
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    About this property
    Enjoy this beautiful updated two bedroom, two bath condo which has all of the amenities you are looking for in a luxurious and relaxing atmosphere. Bay Oaks is set among tropical foliage and beautiful walkways throughout. Enjoy a stroll along the tropical palm trees and tall shade oaks that line...
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    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Gorgeous Direct gulf Front 2 Bedroom Condo on Siesta Keys... JUST REMODELLED1 / 51
    (11)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Ocean Views
    • Housekeeping Included
    • Cable/satellite TV
    • Waterfront
    • Washer
    • Wi-Fi
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 April 2018
    Fishermans cove condo was perfect. It was located at the lower end of the key so it was quiet. The unit allowed for views of the sunrise and sunset. We have booked it for next...
    Reviewed 27 November 2017
    We loved the condo, loved the location. The staff was very friendly and helpful. I cant say anything bad about it, it was GREAT!! I cant wait to go back!
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    About this property
    Our Fisherman's Cove condo description Paradise awaits - GORGEOUS, totally renovated in 2017, 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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    Siesta Key 2 BR, 2 1/2 Bath - *Across From Beach - Pool-view* - Newly Renovated1 / 49
    (4)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    • Cable/satellite TV
    • Air Conditioning
    • Balcony
    • Washer
    • Secure Parking
    • Patio
    • Wi-Fi
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 31 August 2018
    We love this place so much! Every time we begin to think of vacation time ,we always want to come back here ! Its clean affordable and over all well kept. Its become our home...
    Reviewed 28 October 2017
    Lovely condo - great for a Ladies' Weekend Away! Very spacious and clean. It was easy to get to town and the beach using the Frog Hopper FREE taxi service! Washer and dryer was...
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    About this property
    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 unit has everything you need for...
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    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 7
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Grill
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Wi-Fi
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Just cross the street and you are at the entrance to Siesta Key Beach - one of the finest beaches on the Florida Coast and the winner of multiple awards both for its crystal clear waters and its cooling quartz sand. This 2/2 impeccably updated condo is on the first floor and water views...
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    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Patio
    • Wi-Fi
    • Washer
    • Shared Outdoor Pool (Unheated)
    • Balcony
    • DVD Player
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Experience the most amazing #1 rated Siesta Key beach views on the Gulf of Mexico from the 15th floor of the Terrace Building in Siesta Key Village! Hands down, best location with the best views! This home away from home 2 bedroom 2 bath condo with almost 1,187 sq. ft. being almost 1/4 of the...
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    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Patio
    • Grill
    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    • Washer
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Got Paradise!? Well now you do..... This oasis on Siesta Key is just that. The condo is only a couple of blocks away from the beach and rests in Siesta Key Village where you will find lots of great dining, amazing shops, coffee houses and more, all a short walk away. With everything you could want...
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    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Private Siesta Key House - Walk to Village & Beach - Heated Pool/Spa - No Stairs1 / 26
    (3)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Patio
    • Grill
    • Parking
    • Air Conditioning
    • Cable/satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 January 2018
    I stayed over the winter holiday with my husband and other adult family.It was the perfect place to have a pleasant vacation. Close to all shops and downtown and also a short...
    Reviewed 6 September 2017
    What a beautiful modern and superbly located house. Immaculate and well maintained with everything you could possibly need. Our host Randy was excellent and answered our...
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    About this property
    Steps from the islands best restaurants, shops (in the Village area) and a short walk to the #1 beach in the USA! Great home with 2 car and 1 car private garages. Recently renovated including a screened in patio, hot tub and pool. Brand new appliances making this home a great place for monthly...
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    Siesta Key, Florida 34242
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    Beachy Chic Condo in Siesta Key - Waterfront - Free wifi - Sleeps 4 !1 / 29
    (19)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
    • Patio
    • Waterfront
    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    • DVD Player
    • Wi-Fi
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 July 2018
    Nothing negative to say here. Location was great, condo was spacious and had everything we needed. I would definitely book to stay here again!!
    Reviewed 22 June 2018
    We will return to the Beachy chic Condo !! Loved the location, easy to walk to shops and restaurants (.25 mile away) . Sunrise was spectacular from the dock on the inter coastal...
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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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    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
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    • Cable/satellite TV
    • Hot Tub
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beds: 1 King Bed & 1 Sofa Bed OR 2 Queen Beds & 1 Sofa Bed (bed size varies in each of our units) Welcome to our Beach Get-away...where we invite you to relax, unwind and enjoy our casual Siesta Key way of life. Resting just yards from the powdery-white sands of Siesta Key's world famous,...
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    Siesta Key, Florida 34242
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Charming Siesta Key Condo, Walk to Beach, Pool1 / 60
    (5)Excellent
    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 21 May 2017
    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 with 2 Queen Beds is beautifully furnished, all new, and super clean! WALK RIGHT OVER TO THE #1 BEACH IN AMERICA, you do not need a car on this vacation stay. And if you want to see the rest of Siesta Key you can take the free shuttles, and the new Siesta Key Trolley...
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    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Sarasota-Siesta Key Coastal Five Bedroom with Pool and Spa1 / 38
    (7)Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 13 Quick View
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    • Air Conditioning
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    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 31 July 2018
    My family with extended family(total of 8) shared this large home with 5 bedrooms and we had plenty of room and at same time all had our privacy when we wanted it. The kitchen...
    Reviewed 2 April 2018
    Perfect location. Very close to the beach and downtown. The sliding kitchen windows opening to the counter bar in the screened in pool and hot tub area made eating in so fun...
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    About this property
    Excellent location at only 120 Yards To The Cool White Quartz Sand Of Siesta Beach! ?This Home Has Water Frontage, Pool, Hot Tub And BBQ Area Within A Screen Enclosure. There Is A Nice Sized Sunning Patio As Well With Views Down The Waterway. This Home Entertains Excellent Because The Pool Area Is...
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    Siesta Key, Florida 34242
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 13
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    Updated Townhouse!  Private access to Beach. Enjoy Tennis, Heated Pools, Fishing1 / 38
    (15)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 29 August 2018
    This was our third vacation in Siesta Key and by far 1320 was the best accommodation we have had there.We booked via FlipKey, who were right on the ball with everything...
    Reviewed 6 August 2018
    We loved our time at Siesta Bayside Townhouse! Clean, clean, clean—in all the corners, under the beds, to the kitchen and the bathrooms. Thea provided everything you’d need from...
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    About this property
    Across the street is our Private Access to one of the BEST beaches - Siesta Key Beach with the world renowned white sands - rated one of the top ten in the US! Gulf & Bay Club Bayside is a gated resort community of Key West style Town Homes all with one car attached garages. Gulf & Bay Club...
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    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Beach Access, Heated Pool, Boat Docks, and MORE for the perfect beach getaway1 / 29
    (1)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Grill
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 October 2018
    We thoroughly enjoyed our visit to siesta key this conveniently located two bedroom unit only moments from the glistening sands and sunsets made our stay most memorable… The...
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    About this property
    Siesta Key has grown in popularity over recent years due to its beautiful miles of pure white quartz sand beaches, vibrant nightlife, artistic culture, and plethora of things to do on and off the emerald waters. This property sits centrally on the island, just minutes form Siesta Key Village and...
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    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    Sea Shell Condo-Right On Crescent Beach-Siesta Key1 / 24
    (9)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Balcony
    • Air Conditioning
    • Terrace
    • Wi-Fi
    • Grill
    • Ocean Views
    • Parking
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 April 2018
    Clean, roomy, well-stocked with all kitchen amenities that you could think of. Master bedroom very roomy. Extra space for your bathroom essentials in medicine cabinet...
    Reviewed 25 August 2017
    We stayed in unit 207. The property is very nice. The condo was clean, modern and well equipped with all your kitchen needs and wants. We like to cook and were pleased with the...
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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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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Directly across from Siesta Beach Access! Included with your stay: Complimentary Bicycles, Beach chairs, Beach-Towels, Free-rides around Siesta and a 7-day week office for your convenience and guest needs. This darling Florida getaway has 2 king size bedrooms and 1 bedroom with two twin size beds...
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    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Spacious 4bed air-con villa on Siesta Key1 / 26
    (2)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 May 2016
    This lovely 4-bed villa was well proportioned and kitted out for our party of 6 adults but deciding who should get the biggest and best bedroom with the only en-suite could have...
    Reviewed 22 July 2015
    We stayed two weeks here and had a wonderful time. The villa was very spacious with large bedrooms, eat-in kitchen and living rooms. Most impressive was how well equipped it...
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    About this property
    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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    Beach Walk Townhouse1 / 16
    (5)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 22 July 2018
    We had a great time. Very close to beach and within walking distance to many restaurants. The place was clean and as advertised.
    Reviewed 21 May 2018
    The space was great. Very close to Siesta Key Beach. The only thing is that it is a 3 floor duplex and it makes it kind of difficult bringing your stuff up the stairs.
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    About this property
    Spacious Beach Getaway (sleeps 6), Calle del Otoño unit D, a 3 bedroom / 2.5 baths townhouse of 2,000sq/feet which is located right next to Gumbo Limbo. It offers 1 king, 2 twins and 1 queen size bed, brand new carpeting (January 2016), a balcony with partial Gulf view and a heated pool. This...
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    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Walk to Village, Heated Saltwater Pool,  Bike/Walk to Beach, WiFi/Cable, Custom1 / 38
    (1)Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Grill
    • Private Outdoor Pool (Unheated)
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Blue Mermaid is located less then 1/2 mile and less than a 10 minute stroll from Siesta Key Village. It's just a short hop from there (6 minutes or so) to the beach and the crystal sands and sparkling waters of the Gulf of Mexico on Siesta Key. Walk to our local gourmet grocery store for...
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    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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    Crescent Arms 703S, Beachfront Penthouse, Gulf View from Every Room! 2BR-BA1 / 40
    (12)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • DVD Player
    • Patio
    • Wi-Fi
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    • Waterfront
    • Air Conditioning
    • Ocean Views
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 July 2018
    This condo is in a great location, steps from the beach with an amazing view of Point of Rocks. This is our second year renting from the owners who are great to work with. Very...
    Reviewed 18 June 2018
    Pavan and Tracy are very attentive and accommodating. During our stay we needed nothing. the Condo is well appointed, nicely furnished and had everything we needed, including...
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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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    Walk to the Beach and More from this Fully Renovated Unit W/ Heated Pool1 / 24
    (2)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
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    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 20 October 2016
    Pros; Great location, super quiet-depending on situation of who's above you, very clean, 7-eleven and some great Restaurants walking distance from the Beach house. Also my wife...
    Reviewed 28 December 2015
    The best part of this rental was the location! It is less than a 5 min walk from the beach access and wasn't too far to be able to easily carry our beach gear to the beach. The...
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    About this property
    Walk the soft sandy shores of Siesta Key beach from this 1 bedroom1 bath vacation rental on Siesta Key. The unit offers an open floor plan with full kitchen, dining area, and living room with flat screen TV. Through the large sliding doors you can sit out and enjoy the pool area on the screen...
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    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Honeymoon Suite - Gulf views - next to Siesta Key Beach1 / 21
    (6)Very good
    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 30 January 2018
    The suite was lovely, and the bed was very comfortable. The grounds and pool were very well maintained. Great Beach access.
    Reviewed 3 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...
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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 Villa Palma - Fall Special - All Inclusive Pricing1 / 21
    (5)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Patio
    • Shared Outdoor Pool (Unheated)
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    • Wi-Fi
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 8 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 11 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 schictyle. The newly renovated kitchen is sleek in design and...
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    Siesta Key, Florida 34242
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
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    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Discover the beauty of Siesta Key at Siesta Villa Whispering Palms. Our recently renovated 3-bedroom, 2-bathroom stand-alone villa is your new home-away-from-home. Featuring 1700 sqft of air-conditioned living space, an open floor plan, large living spaces, spacious bedrooms, and well-manicured...
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    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    A Tropical 1Br Retreat on a Florida Isle1 / 24
    (5)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Patio
    • Balcony
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    • DVD Player
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 August 2018
    My son and I had an amazing experience! The hospitality and genuine care from the family was refreshing. In addition, the salt water pool just steps from our patio, beautiful...
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    About this property
    Welcome to Siesta Palms by the Beach . . . where we invite you to relax, unwind and enjoy our casual way of life. Resting just one block from the powdery-white sands of Siesta Key's world famous, award-winning Crescent Beach is our tropical Siesta Palms by the Beach. With no busy streets to cross,...
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    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Air Conditioning
    • Patio
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    • Grill
    • Balcony
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Looking for fantastic location? This 2 bedroom, 2 bath condo on Siesta Key sits right across from the Siesta Key Beach voted #1 Beach in USA. This large condo is light and bright with large wrap around balcony and great view of the pool. It is clean and comfortable with everything you need for a...
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    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
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    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Got Paradise!? Well now you do..... This oasis on Siesta Key is just that. The condo is only a couple of blocks away from the beach and rests in Siesta Key Village where you will find lots of great dining, amazing shops, coffee houses and more, all a short walk away. With everything you could...
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    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    WOW Factor Siesta Key Beach Gulf Front Condo in Siesta Dunes on #1 Beach in USA1 / 69
    (19)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Washer
    • Ocean Views
    • Housekeeping Included
    • Hot Tub
    • Cable/satellite TV
    • Wi-Fi
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 October 2018
    It was a fantastic place for us to stay! The condo is located on Siesta Key along Siesta Beach...the beach that has been designated, The # 1 Beach in America". The condo was...
    Reviewed 25 September 2018
    We really enjoyed our stay. The location is amazing and right on the beach.This is a great family-friendly condo with a beautiful pool and close to many restaurants and...
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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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    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
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    • Private Outdoor Pool (Unheated)
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy the global flair of Siesta Key, Villa Soleil! This beautiful, stand-alone villa has 3 bedrooms, 2 baths and boasts fine appointments throughout. It’s an eclectic and artistic mix of French and Asian décor met by coastal pops of color and high quality design. It’s extravagant, and comfortable....
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    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Discover Siesta Key at this three bedroom two bathroom vacation rental home located in the heart of Siesta Key tucked away in a quiet neighborhood. Hire one of the many free ride services on the key for a quick trip to visit Siesta Key village where you can find a multitude of restaurants,...
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    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    If you're dreaming of a scenic seascape getaway, this recently remodeled Bianco Sands’ is the perfect vacation home for you. Included with your stay: Complimentary Bicycles, Beach chairs, Beach-Towels, Free-rides around Siesta and a 7-day week office for your convenience and guest needs. Situated...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Quiet and Comfortable Condo Near Turtle Beach1 / 42
    (5)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • DVD Player
    • Private Outdoor Pool (Unheated)
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    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 March 2018
    We really enjoyed our stay at Dana Z's condo. It was close to all the amenities on Siesta Key. The condo was quiet and peaceful. The water front gave us many enjoyable evenings...
    Reviewed 21 February 2018
    Great place, but needs some attention to the bed in master bedroom also a updated tv in the living room. I would recommend this place for older adults.
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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 Condo, Crescent Arms, unit 605 South1 / 24
    (18)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Cable/satellite TV
    • Balcony
    • Secure Parking
    • Air Conditioning
    • Ocean Views
    • DVD Player
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 July 2018
    This was our second time coming to the specific condo and booking with Karen. After our first trip, we had to come back. The beach is incredible and the sand feels just like...
    Reviewed 2 July 2018
    This condo works perfectly for our family of 4! We returned for our 3rd stay and will definitely be back. This space is immaculate, updated and comfortable. The owner keeps it...
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    About this property
    *** 9 night special January 6-15, 2019. **** Split floor plan with each bedroom having a private full bath, tv and access to the lanai. Totally updated, comfortable furniture and relaxing condo. Free Siesta Breeze open air trolley that runs from 10a.m. til 10 p.m. up and down the key. Secure...
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    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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