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Southwest Florida Vacation Rentals: SIESTA KEY

Florida's Siesta Key has one of the top 10 beaches on Earth! This island gem lies between the Bay and the Gulf of Mexico - enjoy beautiful sunsets nightly. No car needed; ride vacationer-friendly trolleys. Choose one of our oceanfront condos steps from the Gulf. Excellent values with full furnishings, amenities.
Florida Vacation Rentals - Siesta Key

SIESTA KEY

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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
FLASH SALE! Left to Save 36% 2/25 - 3/11!
Bay Tree Club 206C
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Was $3,498 NOW $2,222
14 day minimum stay required. Imagine waking up in the morning knowing that a quiet Siesta Key beach lies just across the street, promising a day of sun and fun. 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
Limited-Time Offer: Stay before 4/15/17 and Save Up to 22%!
Excelsior 107
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Only $300 to
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14 day minimum stay required. With the Bay in back and the Gulf in front, our condo at Excelsior 107 sits on a little strip of paradise! more info
Only 1 week left in the next 60 days!
• City: Siesta Key
• View: Best Value/Garden
• Sleeps: 6
Guest Rating: 4.6/5
10 Guest Reviews
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
Limited-Time Offer: Stay before 4/15/17 and Save Up to 16%!
Crescent Street 1138 B
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Only $300 to
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For those who are all about “the Beach life,” Crescent Street 1113B brings an opportunity to soak in the sun and feel the sea breeze like you have never felt before. This vacation rental destination is the place where you want to be on your next holiday ... more info
Only 3 weeks left in the next 60 days!
• City: Siesta Key
• View: Best Value/Garden
• Sleeps: 4
Limited-Time Offer: Stay before 4/15/17 and Save Up to 29%!
Polynesian Gardens Villa P6
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Only $300 to
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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
Only 2 weeks left in the next 60 days!
• City: Siesta Key
• View: Best Value/Garden
• Sleeps: 4
Limited-Time Offer: Stay before 4/15/17 and Save Up to 16%!
Sunset Royale 200
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Only $300 to
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Sunset Royale 200 is literally across the street from Siesta Beach and the Gulf of Mexico. The only way you could be any closer would be to sleep on the sand itself—and that would be far less comfortable and enjoyable than staying in our 2-bedroom, ... more info
Only 3 weeks left in the next 60 days!
• 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
Limited-Time Offer: Stay before 4/15/17 and Save Up to 29%!
Casa Siesta
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Only $300 to
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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
Only 2 weeks left in the next 60 days!
• City: Siesta Key
• View: Best Value/Garden
• Sleeps: 4
Limited-Time Offer: Stay before 4/15/17 and Save Up to 16%!
Midnight Cove II 432
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Only $300 to
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Sun seekers Delight! Enjoy your morning coffee looking at the palms and oaks lining the boat basin from your own private, sunny, 3rd-floor balcony. more info
Only 1 week left in the next 60 days!
• City: Siesta Key
• View: Lagoon View
• Sleeps: 4
Limited-Time Offer: Stay before 4/15/17 and Save Up to 16%!
Palm Bay Club Bayside 328
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Only $300 to
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Are you ready for a great escape? If so, Palm Bay Club’s Bayside 328 is the perfect spot for you. more info
Only 1 week left in the next 60 days!
• City: Sarasota
• View: Best Value/Garden
• Sleeps: 4
Guest Rating: 4.5/5
8 Guest Reviews
Bay Oaks B-52
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Only $300 to
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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
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
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 at sits on a little strip of paradise! more info
• City: Siesta Key
• View: Best Value/Garden
• Sleeps: 6
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
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
• City: Siesta Key
• View: Best Value/Garden
• Sleeps: 6
Bay Oaks D-42
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Only $300 to
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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
Harbor Towers Yacht & Racquet 324
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Only $300 to
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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
• City: Siesta Key
• View: Bay View
• Sleeps: 4
Twin Palms 5
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Only $300 to
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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
1 Guest Reviews
Limited-Time Offer: Stay before 4/15/17 and Save Up to 16%!
Palm Bay Club G46
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Only $300 to
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The accolades keep pouring in. Guests and media alike rate the Palm Bay Club as a perfect destination for romantic getaways and family vacations. more info
Only 1 week left in the next 60 days!
• City: Siesta Key
• View: Best Value/Garden
• Sleeps: 4
Guest Rating: 4.45/5
44 Guest Reviews
Limited-Time Offer: Stay before 4/15/17 and Save Up to 16%!
Our House at the Beach 222
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Only $300 to
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There's plenty of room for everyone here at Our House. We have a split-level living/dining area, with a large living room made for a crowd! more info
Only 1 week left in the next 60 days!
• City: Siesta Key
• View: Best Value/Garden
• Sleeps: 4
Guest Rating: 4.68/5
37 Guest Reviews
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