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Pet Friendly Holiday Rentals in Siesta Key

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    Travellers to Siesta Key are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    108 Matching Rentals in Siesta KeyView all 545 rentals
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    8 Steps to the Sand of Siestas Best Beach! - Old Man and the Sea Inn (2)1 / 43
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Private Siesta Key House - Walk to Village & Beach - Heated Pool/Spa - No Stairs1 / 26
    (2)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    2 bedroom/1 bath Contemporary Beach Cottage1 / 10
    (2)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Key West Suite next to Siesta Key Beach1 / 32
    (7)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Wi-Fi
    • Patio
    • Washer
    • Air Conditioning
    • Balcony
    • Grill
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 weeks ago
    The location of this property is perfect, right across from the beach and within easy walking distance to the Village. Our party consisted of 3 couples away for a long weekend...
    Reviewed 21 May 2016
    Spacious enough for 3 little ones and 2 adults. My wifeet and I stayed in the makeshift room next to family room. Very clean and well kept. We were spoiled and had the property...
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    About this property
    2 apartments to choose from: Key West Suite A relaxed beach experience. This cozy two bedrooms & den apartment, full 2 baths (1 King bed + 2 Twins + 1 Queen) 1,200 sq/ft. suite on second level with two private balconies and partial Gulf view from the den. This apartment is fully furnished and...
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    Siesta Key, Florida 34242
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    8 Steps to the Sand of Siestas Best Beach! - Old Man and the Sea Inn (3)1 / 42
    (21)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Grill
    • Wi-Fi
    • Cable/satellite TV
    • Waterfront
    • Patio
    • Washer
    • Balcony
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 weeks ago
    This place was amazing and could not have been more perfect to stay at for an extended vacation!!!! The unit was cozy and comfortable- it had everything that you could possibly...
    Reviewed 9 April 2018
    Great location! Only steps to beach access. Our unit was very clean and had all we needed for 2 people. The owner Daniel, was great to work with. He always replied to any...
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    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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    PRISTINE SIESTA KEY VILLAGE HOME1 / 28
    (5)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Waterfront
    • Air Conditioning
    • DVD Player
    • Washer
    • Wi-Fi
    • Cable/satellite TV
    • Hot Tub
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 29 August 2017
    Beautiful accommodation, superbly located and very well equipped. The new swimming pool is the jewel in the crown, and Cydney was a pleasure to deal with. We would hope to go back.
    Reviewed 20 July 2017
    I can't say enough wonderful comments about this house. It's charming, comfortable, gorgeous, adorable, lovely....I could go on and on. My family has enjoyed walking to...
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    About this property
    Hidden behind a contemporary privacy wall, enter into our front yard oasis. The perfect setting for tanning, dining and entertaining alongside the waterfall feature. Extensive renos offering a stunning gourmet kitchen, updated bathrooms, flat screen tv's in bedrooms and the most appealing Lanai...
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    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    8 Steps to Sand Path of Siesta's Best Beach! - Old Man and the Sea Inn (4)1 / 47
    (34)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    • Patio
    • Balcony
    • Washer
    • Cable/satellite TV
    • Waterfront
    • Wi-Fi
    • Grill
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 April 2018
    Great location. Steps away from beach, short walk to restaurants, free shuttles to the village. Clean condo.
    Reviewed 12 September 2017
    We stayed for a long weekend and couldn't have been more pleased. Their team has thought of everything- all you need to do is sit back and enjoy the amazing location and town...
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    About this property
    A Gertrude Rentals Property! Rated 'The World's Finest, Whitest Sand' at the Great International Sand Challenge. Perfect for travelers in search of uncomplicated seclusion. Residing in Siesta Keys most 'private' non-private beach neighborhood and just one marlin's length (5 steps) from yard to...
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    Siesta Key, Florida 34242
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 8
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    Sarasota-Siesta Key Coastal Five Bedroom with Pool and Spa1 / 38
    (6)Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 13 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Secure Parking
    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
    Reviewed 4 March 2018
    The location is fantastic. Literally one short block to worlds greatest beach. Short one mile walk into the quaintest town with lots of restaurants, bars, shops. The house was...
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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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    Luxurious 2 BR Condo - Short Walk to Siesta Beach1 / 14
    (18)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Grill
    • Cable/satellite TV
    • Sauna
    • DVD Player
    • Wi-Fi
    • Balcony
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 April 2017
    We stayed at the apartment for 2 weeks during Easter holidays with our 2 girls (aged 1 and 4). We had a lovely holiday. We felt there was some positives and negatives with the...
    Reviewed 1 February 2017
    Everything about this condo was fantastic! The beautiful two bedroom/ two bathroom, spacious, quiet, the large swimming pool and two gas grills which we used often, we will...
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    About this property
    Newly furnished, newly renovated 2BR (one king size & 2 single beds) + convertible sofa bed, 2 Bathrooms 2nd floor condo (sleeps 4-6), and with all the amenities of a comfortable home. Located in White Sands Village with 7 acres of lush tropical surroundings, our air-conditioned condo offers two...
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    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
    • Patio
    • Wi-Fi
    • Washer
    • Cable/satellite TV
    • Grill
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Beach Place is a small group of tropical garden Floridian beach cottages located at Siesta Key Beach - 30 seconds to the sand and 10 - 15 minute walk to Siesta Village. We have a heated pool, tiki cabana wet bar for the guests to entertain at, beachfront picnic and BBQ, poolside BBQ, plenty...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Dog-Friendly Siesta Key Bungalow, Wifi, Adorable Cottage Close to Siesta Key Bea1 / 27
    (2)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Patio
    • Air Conditioning
    • Washer
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 July 2017
    The house was nice, large size, comfortable, nice neighborhood close to the beaches, shopping and restaurants. Perfect for our family and dogs that we brought along on our...
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    About this property
    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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    Siesta Key, Florida 34242
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Tiny House Siesta - Yellow Lifeguard Stand Tiny House1 / 32
    (1)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Patio
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 May 2018
    We were 4 adults that stayed for 2 nights. The little houses are only five mins drive from the glorious beach.Though compact the houses have everything (except a hairdryer...
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    About this property
    Imagine Yourself At (Tiny) Home: Beach life is best! Enter through the bright yellow, life-sized replica of a Siesta Key lifeguard stand, and drop your beach bags on the two stools beneath our surfboard-shaped breakfast bar. Passing through the living room, decorated with just a touch of...
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    Siesta Key, Florida 34231
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    8 Steps to the Sand of Siestas Best Beach! - Old Man and the Sea Inn (1)1 / 47
    (1)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    • Wi-Fi
    • Air Conditioning
    • Balcony
    • Patio
    • Cable/satellite TV
    • Washer
    • Grill
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 July 2017
    Wonderful, relaxing, perfect location! On the quiet side of the key, easy close access to gorgeous crescent Beach. Easy quick walk to bus stop and local market, restaurants as...
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    About this property
    Old Man and the Sea Inn - 1 marlin to the sand! 2BR (sleeps 8). Brought to you by Gertrude Rentals! Perfect for travelers in search of uncomplicated seclusion. 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...
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    Siesta Key, Florida 34242
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 8
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    Beautiful & Modern Condo - Walk to Beach & Village1 / 18
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Air Conditioning
    • Balcony
    • Wi-Fi
    • Sauna
    • Waterfront
    • Grill
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    White Sands Village is located on Siesta Key, just few steps from Siesta Beach and directly on the canal across from Philippee Creek. Highlights of White Sands Unit 303: Free high-speed WiFi Ground floor unit More than 200 channel cable TV DVR to watch your favorite show when you want to 50 inch...
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    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Siesta Key 2 Bedroom 1 Bath Modern/Contemporary Decor Apartment1 / 32
    (23)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Porch
    • Parking
    • Patio
    • Air Conditioning
    • Washer
    • Grill
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 October 2017
    Siesta key is a wonderful place to stay ,And this apt was the cherry on top, minutes from the beach and village area,Not only where the accommodations great , they have bikes...
    Reviewed 29 April 2016
    Traveled with business associates & spouses, combining business & pleasure.Great ;location for both business in Sarasota as well as amenities of Siesta Key.Very well...
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    About this property
    This lovely 2BD/1BA apartment is located just 1 mile from beautiful Siesta Key Beach. Siesta Key was rated the #1 Beach in the United States by Dr. Beach (2011) and the #2 Beach in the U.S. in the 2013 TripAdvisor Travelers Choice Awards. Siesta Key was listed in 2014 by Smarter Travel.com as...
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    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    Siesta Key 3 Bdrm Private House with Heated Pool minutes from village and beach1 / 20
    (3)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Waterfront
    • Grill
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Washer
    • Patio
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 August 2017
    I travelled to Florida with my fiancee for work and decided to extend our stay to enjoy a little R & R. We have used AirB&B in the past and we found this gorgeous home to...
    Reviewed 10 April 2017
    This is a beautiful home a short bike ride to Siesta Beach. It comfortably sleeps 8 on beds in 3 large rooms. 2 of the rooms have a glass door that opens up to the pool and...
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    About this property
    Surrounded by lush, tropical garden, our private villa is situated on a quiet cul-de-sac bordered on two sides by Lake Nancy. A birdwatchers and nature lovers delight! Sip your coffee in your PJs on the private, sunny terrace or enjoy a dip in the large heated pool. Walk for miles on the beach...
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    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Siesta Key Beachfront 3 Bedroom Home, Sarasota1 / 33
    (3)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    • Washer
    • Cable/satellite TV
    • Internet Access
    • Grill
    • DVD Player
    • Air Conditioning
    • Patio
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 January 2018
    This is a very nice three story three bedroom house. The first floor includes two separate garages with the house entrance in between. The second floor includes a spacious...
    Reviewed 4 November 2017
    We enjoyed our stay at this well maintained tastefully decorated 3 bedroom home a short walk on the beach to the village of Seista Key. It was clean and recently updated...
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    About this property
    Description:Walk out the back door to the clean white sand of Siesta Key Beach. This home has private Siesta Key beach frontage on the prime section of beach, there are no homes between you and the beach. Nearly every room has a full view of the beach. The entire back of this house opens with...
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    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 9
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    Crescent Cottage1 / 16
    (6)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
    • Air Conditioning
    • Parking
    • Cable/satellite TV
    • Waterfront
    • Patio
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 November 2016
    Very cozy but good for 1-2 people. Walk to private beach and pool. Only thing - can be quite noisy at night with the bar across the street but otherwise great
    Reviewed 6 July 2016
    Old Florida vibe, love it. Short walk to beach! Perfect size place for my husband and I and our 60 lb lab. The private fenced grassy area in backyard was perfect for our dog...
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    About this property
    PET Friendly! This one bedroom and one bathroom beach bungalow is located 150 yards away from the beach. You can walk to restaurants, shops and a great pool area. Queen bed and a sleeper sofa make it possible to sleep four. Enjoy your morning coffee on your private screened porch or while you walk...
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    Siesta Key, Florida 34242
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Tiny House Siesta - Tiny Blue Oasis – a tiny house with 3 Queen beds1 / 17
    (1)Terrible
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Parking
    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    It will be love at first sight with our tiny Blue Oasis; her cerulean color with bright white trim tells you you have arrived in the tropics, and her welcoming front porch is just big enough for you to engage in the southern pastime of porch sittin’. Cool off inside where the bleached white wood...
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    Siesta Key, Florida 34231
    Condo/Apartment - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    Top in Siesta Village at Best Beaches, Food & Entertainment! - Casa Van Lopik(J)1 / 98
    (17)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
    • Waterfront
    • Balcony
    • Patio
    • Wi-Fi
    • Porch
    • Washer
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 June 2016
    While ratings and reviews are subject to personal taste, we found this property average at best. The positives included a nice size home, 3BR, 2BA, 2 blocks to the beach and...
    Reviewed 4 December 2015
    Our extended family of 7 with 4 adults and 3 children, stayed 4 nights at this property. We were thrilled to see that the grocery store was at the end of the street, as were all...
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    About this property
    Casa Van Lopik (jardin), our garden facing suite, is a large 3BR home. Brought to you by Gertrude Rentals! Perfectly located between the best beaches, shopping dining and entertainment on the island. It was named for our father who was a ships captain and sailed the world for 30 years but always...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    Grand White Sands 303 - Walk to beach and village1 / 17
    (2)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Sauna
    • DVD Player
    • Wi-Fi
    • Patio
    • Waterfront
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 February 2017
    Enjoyed our stay in this unit , big screen tv was the best. Short walk to the beach, the dog loved it. Everybody in the complex was very friendly and helpful.
    Reviewed 6 January 2016
    Close to all the excellent facilities of Siesta Key and within a comfortable walking distance of the magnificent Siesta beach, Grand White Sands 303 was the ideal place to...
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    About this property
    Please also visit siestakey-whitesands with the usual US ending. There you'll find lots of usedul information on the condo and a travel guide.White Sands Village is located on Siesta Key, just few steps from Siesta Beach and directly on the canal across from Philippee Creek.Highlights of White...
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    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Parking
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Cable/satellite TV
    • Wi-Fi
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This Luxury Four Bedroom, Four and a Half Bathroom Home will leave you breathless as you enter. There are not many large rental homes, this close to Siesta Beach, that live like this home. Most Rentals by the beach have their living area 16 feet above the ground level and the pool below, which is...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 12
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    The Top Siesta Key Location, The Village Studio - Eat Shop Beach!1 / 32
    (15)Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Air Conditioning
    • Outdoor Dining Area
    • Parking
    • Wi-Fi
    • Patio
    • Waterfront
    • Cable/satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 29 March 2017
    We loved walking everywhere - the beach, especially every sunset; shops, great food. The condo was lovely, and the setting enriched by the other owners in the complex.
    Reviewed 25 March 2017
    We enjoyed our 3 day stay. A longer stay would require a larger place but it was perfect for this time. Our host was very helpful and had a nice gift awaiting our arrival :)
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    About this property
    A Gertrude Rentals property. Enviable location just steps away from everything! The Siesta Key Village Studio is 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...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Stay on Siesta - SEA - ESTA HOUSE1 / 19
    (2)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Outdoor Dining Area
    • Air Conditioning
    • Wi-Fi
    • Grill
    • Patio
    • Parking
    • Washer
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 July 2017
    "Avenida Del Mare" was the perfect vacation rental for my family. The home is well appointed, all renovated with comfy beds and amazing bathrooms (love the rainshower...
    Reviewed 9 November 2016
    Convenient location, just a short stroll to beautiful Siesta Beach. Beach gear available, we left some sand toys for the kids.Very well equipped and beautifully decorated. All...
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    About this property
    This Siesta Key 3 Bedroom 2 Bath Home has been completely remodeled. This home is 1 block from the Famous Siesta Key Beach. Granite counter tops, to accent the new white cabinetry. Beautifully tiled bathrooms with all new hardware. All walls beautifully textured. Screened Lanai. Nice back yard. 1...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Flip Flop Cottages Siesta Key Florida1 / 42
    (2)Average
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Waterfront
    • Patio
    • Porch
    • Grill
    • Cable/satellite TV
    • Wi-Fi
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 23 May 2015
    Nice overall for what we needed-good location for beach hoppers like ourselves. Could get to Lido beach and turn around and go to Venice beach with still many beaches between...
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    About this property
    YOUR PRIVATE GETAWAY ON THE KEY ASK ABOUT OUR SUMMER SPECIALS!!!!!!!!! Does not include Weekends or Holidays!!! Looking to relax, Flip Flop Cottages is the place to be for a quaint and private vacation in Siesta Key, Florida. Come and stay at our serene environment and enjoy and visit all the...
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    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Beach House Bungalow #11 / 8
    (1)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Terrace
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 April 2015
    Very nice accommodations. Gulf side of Midnight Pass. Five minute walk to beach. Quiet Crescent Beach.
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    About this property
    Located near the South Village of Siesta Key. This newly updated 2 bedroom duplex has it all. A new dipping pool to cool off the hot summer days, along with a BBQ and fire pit for the winter. Lots of space, all new furnishings throughout the home, the large eat in kitchen has plenty of room for...
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    Siesta Key, Florida 34242
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Best in Siesta Village! 1.5 blocks to best beaches! - Casa Van Lopik (Canal)1 / 96
    (19)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Reviewed 16 April 2018
    This was the perfect place for eight fabulous women who were celebrating life. The beds were comfortable and the rooms spacious. The hot water plenty. It was a plus to have...
    Reviewed 6 March 2017
    Location is the best thing about this condo -- short walk to beach and to Siesta Key Village. Very convenient. Another big "pro" was Daniel. The owner is very...
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    About this property
    A Gertrude Rentals property! Large 3BR home perfectly located between the best beaches, shopping dining and entertainment on Siesta. Leave the car behind. After the beach, you could wander to town for fresh oysters and seafood, drinks, live music or ice cream, or just relax in a tropical garden...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Private Outdoor Pool (Heated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Casa Tegula! Our newly constructed luxury cottage has all the amenities your large group [up to 12!!!] can fathom. Inside you’ll enjoy contemporary porcelain wood style flooring throughout the entire three-story building, an elevator to access each landing from the ground floor, gorgeous...
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    Siesta Key, Florida 34242
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 12
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    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Cable/satellite TV
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    About this property
    Brand new tiny home near the beach! Why stay in a hotel room or even a boring old house when you can stay in a brand new tiny home. Come check out the only tiny beach hotel in America. We are located less than a mile from the world famous Siesta key Beach rated the number one beach in America by...
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    Location Information
    Siesta Key, Florida 34231
    Condo/Apartment - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Casa Junonia! Our newly constructed luxury cottage has all the amenities your large group [up to 12!!!] can fathom. Inside you’ll enjoy contemporary porcelain wood style flooring throughout the entire three-story building, an elevator to access each landing from the ground floor,...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 12
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    Sandy Toes Siesta Key Florida  (6796)1 / 40
    (22)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
    • Cable/satellite TV
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    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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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
    • Private Outdoor Pool (Heated)
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ENJOY CASUAL SIESTA KEY LIVING IN THIS LOVELY HOME WITH SEPARATE DETACHED GUEST LIVING SPACE!! The separate guest quarters allow entertaining while providing your family or guests their own private retreat. It is all about the lifestyle! In total this home hosts 4 bedrooms and 3 baths on the island...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    The Top  Location on Siesta Key - Gertrude's Village House1 / 100
    (30)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 May 2017
    My son booked this for his whole family. There were nine of us. The beach was just a half block away. It was beautiful with cool white sand, aqua water with warm rolling...
    Reviewed 25 September 2016
    Stayed there, the location is great. Everything in walking distance. The kitchen was supplied with everything you need. The positives beyond location varied, quiet, lots of room...
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    About this property
    A Gertrude Rentals property! Our Top Location! Leave the car behind. Richly furnished, perfectly nestled between the best beaches, shopping and dining on the Island, and sure to provide a combination of fun and rejuvenation you won't find in other getaways. Our living room, master bedroom and...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    Sandy Toes Siesta Key Florida   (6798)1 / 37
    (21)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Cable/satellite TV
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    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 weeks ago
    Had everything we needed. We appreciate Joe the maintenance guy checking on us. He was very helpful. Would stsy here again.
    Reviewed 6 June 2018
    Firstly, let me say we've never booked a place which wasn't a hotel or a resort. So this was new for me. I found tripadvisor very helpful and Sandy Toes Siesta Key was a...
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    About this property
    A short stroll down a private road to the #1 Beach in the US. You will love the location - you are located in the Resorts of the SaraSea community and can walk to everything you might need or want... Grocery, restaurants, ice cream, pizza, sports rentals, drugstore or boat rental. You have your...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Casita Morning Star! Our newly renovated luxury cottage (completion date of June 2017) has all the amenities your family [up to 10] can fathom. Inside you’ll enjoy contemporary porcelain wood style flooring throughout gorgeous and decadent bathrooms, new appliances, new washers/dryers,...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 10
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    Three bedroom house directly on beach with gulf vi1 / 26
    (2)Very good
    3 Bedrooms, 4 Bathrooms, Sleeps 7 Quick View
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    • Cable/satellite TV
    • Ocean Views
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    We have a 2 week minimum rental period. Tiffany Sands is a group of 9 townhouses directly on Crescent Beach. Our beach house is a stand alone unit(unattached). We have gulf views with 2 decks facing the Gulf of Mexico. It is a spacious 1,800 sq. ft. and newly decorated with a fully appointed...
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    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 7
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    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Casa Stolida! Our newly constructed luxury cottage (completion date of June 2017) has all the amenities your large group [up to 12!!!] can fathom. Inside you’ll enjoy contemporary porcelain wood style flooring throughout the entire three-story building, an elevator to access each landing...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 12
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    The Shells Villa - Next to Beach & Village1 / 41
    (66)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 27 March 2018
    My family and I just returned from a week at the Shells Villa. We had a wonderful time there and hope to return in the future. Our group consisted of our three grown daughters...
    Reviewed 23 February 2018
    This villa is a medium-sized 3 story house with an Italian flair. Its a 5 minute , pleasant walk to the best beach in Sarasota, and just a few minutes more to a bustling, fun...
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    About this property
    3 Bedroom, 2.5 Bath Beach Villa (Sleeps 8-10) What makes us different than other homes you may be considering: · The Beach - The home is located on the ocean side of Beach Rd., so you just walk out your door and through our private access path. It’s literally 230 feet to Siesta Key Beach....
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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, 4 Bathrooms, Sleeps 12 Quick View
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    • Private Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Villa Cascada is a uniquely configured private home featuring a heated pool/waterfall, 4 bedrooms, 4 bathrooms that sleeps 12, with 2 living areas and 2 kitchens and an almost unbelievable pool courtyard surrounded by lush gardens and a tall privacy wall enclosing the entire property. Each of the...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 12
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    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Private Outdoor Pool (Heated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Casa Ohana! Our newly constructed luxury cottage (completion date of June 2017) has all the amenities your large group [up to 12!!!] can fathom. The location is THE premier location in the heart of Siesta Key Village, just behind Gilligan's and Lelu's Coffee Shop! Inside you’ll enjoy...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 12
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    The Sea Wave and Sea Shell are two separate units which can be uniquely configured to create Villa Brisa Marina, an absolutely beautiful and stunning private pool home. Please Note: These units [Sea Wave & Sea Shell] can be rented separately. Combined, these units are called: Villa Brisa Marina...
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    Siesta Key, Florida 34242
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 3 Bathrooms, Sleeps 14 Quick View
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    • Grill
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    Pet friendly
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    Smoking allowed
    About this property
    Welcome to Casa Coquina! Our newest luxury cottage has all the amenities your large group [up to 12!!!] can fathom. Inside you’ll enjoy contemporary porcelain wood style flooring throughout the entire three-story building, an elevator to access each landing from the ground floor, gorgeous and...
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    Siesta Key, Florida 34242
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 14
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    6 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Balcony
    • Grill
    • Terrace
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    Pet friendly
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    Smoking allowed
    About this property
    Brand New , Gated Residence steps from Siesta Key Beach . Perfect location between the village and crystal sands of Siesta Beach!! Bar's, Restaurants, Shopping, Sport Rentals……..EVERYTHING is within walking distance…..NO CAR NEEDED!!! This brand new 2700 sq ft private residence is simply...
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    Siesta Key, Florida 34242
    Holiday Rental House - 6 Bedrooms, 3 Bathrooms, Sleeps 12
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to The Pearl by the Sea. An absolute one of kind, limited edition home located on prestigous Siesta Key featuring a private heated pool and spa, near America's #1 Beach, on the Grand Canal with intracoastal bay access and a boat dock. You have arrived... If you have ever gone searching for...
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    Siesta Key, Florida 34242
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    New 6 Bedroom, Luxury Home in Gated Community1 / 22
    (1)Excellent
    6 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    • Private Outdoor Pool (Heated)
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    • Air Conditioning
    • Hot Tub
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 April 2017
    View from master bedroom was fantastic. Plenty of room for the 14 of us. Will defiantly book again. Kitchen had all appliances needed. Grill was old and had to light with a...
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    About this property
    Perfectly located, New, 6 bedrooms 4 1/2 bathrooms private home,in a gated community, combines luxury with convenience of location. We offer you a large 6000sf+ home within a short distance to the pristine beaches of Siesta Key and walking to the Village, Restaurants, shops and nightlife. Privacy...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 14
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    About this property
    It is a 220-square-foot luxury tiny home, and it offers all of the facilities and conveniences you need for living comfortably The Dragonfly tiny home features a standard-sized bed in the spacious, loft bedroom, as well as a convertible Ikea bed that turns into a couch in the living quarters....
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    Location Information
    Siesta Key, Florida 34231
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    4 Bedrooms, 3 Bathrooms, Sleeps 13 Quick View
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    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    PURA VIDA OASIS: This spectacular bright cheerful, canal front cottage with a heated pool & spa has 5 bedrooms and 3 baths and it can sleep a total of 13. As you enter Pura Vida Oasis, you will notice an eclectic wine storage rack and desk area awaiting on your right and a lovely dining area with...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 13
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    Honey Mango Cabana – 2/1, Shared Heated Pool, Near Beach Access1 / 24
    (1)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    About this property
    Welcome to the Honey Mango Cabana! This beautiful and vibrant 2 bedroom, 1 bathroom vacation home accommodates up to 6 people. This property is very unique as it is one half of 'Mango Manor,' which is comprised of the two separate cabanas, Honey and Juicy Mango. This provides a fantastic and unique...
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    Siesta Key, Florida 34242
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    The Coral Reef and Star Fish Casitas are two separate units which can be uniquely configured to create Villa Dom Bisa, features its own brand new, private heated pool with “sun shelf” and a three minute walk to the Nation’s finest beach [no major streets to cross]. Please Note: These units [Coral...
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    Siesta Key, Florida 34242
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    About this property
    Welcome to The Canopy Cottage! Nestled deep into a beautifully canopied tree neighborhood, this lovely 4 bedroom, 3 bathroom home features a heated pool and spa under a screened in lanai just a few minutes from Siesta Key's #1 Beach! Take a moment to breathe in the peace and serenity under the...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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