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SIESTA KEY VACATION RENTALS

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Jamaica Royale Tower Unit T24
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Only $300 to
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Fresh ocean breezes, spectacular sunsets, beautiful gulf view, and rolling waves await you at this Gulfside condo! Enjoy all the luxe comforts of an upscale rental plus the convenience of a private walkway to the beach! more info
• City: Siesta Key
• View: Gulf View
• Sleeps: 6
Jamaica Royale Tower T23
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Only $300 to
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Welcome to beach living with gulf views from this breezy, comfortable condo on the shores of Siesta Key! Part of a luxe complex, it offers many amenities just a stone's throw from the surf! more info
• City: Siesta Key
• View: Gulf View
• Sleeps: 4
Limited-Time Offer: Stay before 12/16/17 and Save Up to 16%!
Gulf and Bay Club: Bayside 1303-D
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Only $300 to
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When you pull up to the Gulf and Bay Club: Bayside 1303-D you will know right away that you made the perfect decision for your family vacation. Beautiful palms adorn the grounds to give you a totally tropical vibe. more info
• City: Siesta Key
• View: Best Value/Garden
• Sleeps: 6
FLASH SALE! Left to Save 16% 10/21 - 10/28 or Save 16% 10/28 - 11/4!
Twin Palms 5
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Was $895 NOW $752
You’ll be just a one-block walk from Siesta Key, the #1 rated beach in the USA when you stay at Twin Palms #5. This one-story condo was built in 2003 and retains the wonderful Key West style that is the complex’s hallmark. more info
• City: Siesta Key
• View: Best Value/Garden
• Sleeps: 4
Guest Rating: 4.5/5
2 Guest Reviews
FLASH SALE! Left to Save 16% 10/21 - 10/28 or Save 16% 10/28 - 11/4!
Gulf and Bay Club: Bayside 1226
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Was $895 NOW $752
Just steps from the bay, our newly remodeled condo in a gated Key West-style community is the perfect destination for your Siesta Key vacation. With resort amenities and the ideal location for beach and bay access, Gulf and Bay Bayside is irresistible! more info
• City: Siesta Key
• View: Best Value/Garden
• Sleeps: 6
Guest Rating: 4.69/5
16 Guest Reviews
Siesta Dunes Beach 201
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Only $300 to
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Decked in pure tropical style, Siesta Dunes Beach 201 in Siesta Key, Florida is an ideal choice for families planning to spend all their daytime hours at the pool or the gorgeous on-site beach. As a gulf-side property, it’s easy on the wallet while its ... more info
• City: Siesta Key
• View: Best Value/Garden
• Sleeps: 6
Guest Rating: 4.59/5
22 Guest Reviews
 Jamaica Royale 101
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Only $300 to
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A beach holiday doesn’t get any better when you combine good food and a great place to stay in the mix. This is exactly why you must come over to Jamaica Royale 101 the next time you’re visiting Siesta Key. more info
• City: Siesta Key
• View: Best Value/Garden
• Sleeps: 6
Gulf and Bay Club 108D
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Only $300 to
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Love sunsets? How about white sand, plush beds, a choice of three pools, swans . more info
• City: Siesta Key
• View: Beach Front
• Sleeps: 4
FLASH SALE! Left to Save 16% 10/21 - 11/4 or Save 16% 10/28 - 11/11!
White Sands Village Unit 205
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Was $1,700 NOW $1,428
Beat a path to the beach every day from your own breezy lanai when you stay at this ground-floor condo in a lovely resort. The latest technology, comfy furnishings, and the perfect location await you! more info
• City: Siesta Key
• View: Best Value/Garden
• Sleeps: 6
Sara Sea #12
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Only $300 to
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LOCATION, LOCATION, LOCATION! No need for a car on this vacation. more info
• City: Sarasota
• View: Best Value/Garden
• Sleeps: 6
FLASH SALE! Left to Save 16% 10/21 - 10/28 or Save 16% 10/28 - 11/4!
Bay Oaks D-42
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Was $795 NOW $668
Enjoy the simple pleasures of life by doing anything and everything that you could possibly care to do at the Bay Oaks D-42, Siesta Key Florida where heaven becomes real! The Bay Oaks D-42 is fully equipped with every amenity you can think of! more info
• City: Siesta Key
• View: Best Value/Garden
• Sleeps: 5
Siesta Dunes 8-205
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Only $300 to
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Featuring beautiful wood floors, Siesta Dunes Beach 205 in Siesta Key, Florida is an ideal choice for families planning to spend all their daytime hours at the pool or the gorgeous on-site beach. As a gulf-side property, it’s easy on the wallet while its ... more info
• City: Siesta Key
• View: Gulf View
• Sleeps: 4
Beachaven 52
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Only $300 to
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Imagine this: You step out your front door, and there, at the end of a walkway flanked by shrubbery on one side and an impeccably manicured lawn on the other, are the twinkling white sands of Crescent Beach and, just beyond, the sparkling Gulf of Mexico. ... more info
• City: Siesta Key
• View: Best Value/Garden
• Sleeps: 4
Guest Rating: 4.5/5
2 Guest Reviews
FLASH SALE! Left to Save 16% 10/21 - 11/4!
Harbor Towers Yacht & Racquet 324
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Was $1,400 NOW $1,176
Harbor Towers 324 is a cozy 1 bedroom/ 1 bath Siesta Key condo that sleeps 2-4. Guests will feel right at home thanks to the comfy, newly renovated, very modern furnishings and amenities. more info
Only 3 weeks left in the next 60 days!
• City: Siesta Key
• View: Bay View
• Sleeps: 4
Guest Rating: 5/5
1 Guest Reviews
FLASH SALE! Left to Save 16% 10/28 - 11/4!
Bay Oaks B-52
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Was $795 NOW $668
Featured on HGTV's Beachfront Bargain Hunt TV show! With views over a sunny, peek a boo view of the Intracoastal Waterway, a stay at Bay Oaks B-52 provides great value for a vacation filled with anything and everything you care to do. more info
• City: Siesta Key
• View: Best Value/Garden
• Sleeps: 6
Limited-Time Offer: Stay before 12/16/17 and Save Up to 16%!
Excelsior 306
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Only $300 to
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With spectacular views of the beautiful trees, pond, pool and peek a boo view of the Intracoastal, you will be asking yourself why you didn't choose Excelsior 306 sooner. Our 3 bedroom condo sits on a little strip of paradise! more info
Only 3 weeks left in the next 60 days!
• City: Siesta Key
• View: Best Value/Garden
• Sleeps: 6
Siesta Shores 13
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Only $300 to
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Situated just steps away from the "world's finest, whitest sand" and all of the enjoyment that Siesta Key has to offer, this lovely 3 bedroom/2 bathroom cottage sleeps 8 guests and is the perfect Floridian escape for your next vacation. ... more info
• City: Sarasota
• View: Best Value/Garden
• Sleeps: 8
FLASH SALE! Left to Save 16% 10/21 - 11/4 or Save 16% 10/28 - 11/11!
Casa Siesta
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Was $1,500 NOW $1,260
Casa Siesta makes fun in the sun so easy! The 2-bedroom, ground-floor condo is just a short walk from the powdery white sands of Crescent Beach and the azure waters of the Gulf of Mexico. more info
• City: Siesta Key
• View: Best Value/Garden
• Sleeps: 4
Guest Rating: 5/5
1 Guest Reviews
FLASH SALE! Left to Save 16% 10/21 - 11/4 or Save 16% 10/28 - 11/11!
Polynesian Gardens Villa P6
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Was $1,700 NOW $1,428
Looking for a home away from home as you embark upon your upcoming vacation, Polynesian Gardens Villa P6 is an impeccable choice. Located on the tropical border island of Siesta Key, Florida, Polynesian Gardens is an impressive community. more info
• City: Siesta Key
• View: Best Value/Garden
• Sleeps: 4
Limited-Time Offer: Stay before 12/16/17 and Save Up to 16%!
Gulf Holidays 15
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Only $300 to
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Siesta Key is one of the premier beach vacation destinations in America. When you stay at Gulf Holidays 15, you can enjoy all that Siesta Key offers while staying in a comfortable, clean garden-level condo that doesn’t eat up all your vacation budget. more info
• City: Siesta Key
• View: Best Value/Garden
• Sleeps: 4
Limited-Time Offer: Stay before 12/16/17 and Save Up to 16%!
Crescent Street 1138 Unit A
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Only $300 to
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When you stay at Crescent Street 1138A, you can walk to the east side of Siesta Key in just minutes to catch the sunrise over the Gulf of Mexico. Then later, just before dusk, you can take an equally brief stroll over to the west side of the barrier ... more info
Only 2 weeks left in the next 60 days!
• City: Siesta Key
• View: Best Value/Garden
• Sleeps: 6
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The choice is Yours! Option 1: $50 Target Gift Card ... code TARGET50 - Option 2: Take $50 Off ... code SAVE50 - Option 3: Amazon Echo Dot ... code ECHO7 - Place any week long reservation by Oct. 22nd to qualify. Browse Rentals Now!
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