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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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Limited-Time Offer: Stay before 10/22/16 and Save Up to 29%!
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
New Property, Be One of Our First Guests!
Limited-Time Offer: Stay before 10/22/16 and Save Up to 16%!
Palm Bay Club Bayside 328
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Only $300 to
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Guests and media alike rate the Palm Bay Club Bayside #328 as a perfect destination for romantic getaways and family vacations. Treat yourself to an idyllic holiday on Florida’s Gulf Coast, at this 2 bedroom condo with intracoastal water views from your ... more info
• City: Sarasota
• View: Best Value/Garden
• Sleeps: 4
Guest Rating: 4.5/5
8 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
New Property, Be One of Our First Guests!
Gulf and Bay Club 502D
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Only $300 to
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Gulf and Bay 502D will perfectly suit six nice people who deserve a month of total reward and relaxation on Crescent Beach. The resort club is unrivalled for repeat guest satisfaction and its location is smack in the middle of what the Travel Channel ... more info
• City: Siesta Key
• View: Beach Front
• Sleeps: 6
Guest Rating: 5/5
2 Guest Reviews
Limited-Time Offer: Stay before 10/22/16 and Save Up to 29%!
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
• City: Siesta Key
• View: Best Value/Garden
• Sleeps: 4
Guest Rating: 4.67/5
36 Guest Reviews
Limited-Time Offer: Stay before 10/22/16 and Save Up to 29%!
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
Only 2 weeks left in the next 60 days!
• City: Siesta Key
• View: Bay View
• Sleeps: 4
New Property, Be One of Our First Guests!
Bay Oaks D-42, 2 Bedrooms, Updated Condo, Siesta Key Florida
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Only $300 to
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With views over a sunny, courtyard, a stay at Bay Oaks D-42 provides great value for a vacation filled with anything and everything you care to do. Will the simplest pleasures be the most memorable? more info
• City: Siesta Key
• View: Best Value/Garden
• Sleeps: 5
New Property, Be One of Our First Guests!
Limited-Time Offer: Stay before 10/22/16 and Save Up to 29%!
Castaway Cove 3B
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Only $300 to
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With beautiful gulf and lagoon views from both the big lanai and the master bedroom, our condo at Castaway Cove is ideal for your Siesta Key vacation. Spacious and well equipped, the condo offers everything from bikes to a boat dock. more info
• City: Siesta Key
• View: Gulf View
• Sleeps: 5
New Property, Be One of Our First Guests!
Limited-Time Offer: Stay before 10/22/16 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
• City: Siesta Key
• View: Best Value/Garden
• Sleeps: 4
New Property, Be One of Our First Guests!
Limited-Time Offer: Stay before 10/22/16 and Save Up to 29%!
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: 4.42/5
45 Guest Reviews
Limited-Time Offer: Stay before 10/22/16 and Save Up to 29%!
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
• City: Siesta Key
• View: Gulf View
• Sleeps: 4
New Property, Be One of Our First Guests!
Gulf and Bay Club 305C
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Only $300 to
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Roll into the lap of luxury and enjoy a unit that’s still sparkling new. Siesta Key Gulf and Bay Club is known to be the finest long-stay resort in the area - and this newly renovated unit with a new air conditioning and heating system, Gulf and Bay Club ... more info
• City: Siesta Key
• View: Ocean View
• Sleeps: 6
Guest Rating: 4.88/5
8 Guest Reviews
Limited-Time Offer: Stay before 10/22/16 and Save Up to 29%!
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
Only 2 weeks left in the next 60 days!
• City: Siesta Key
• View: Best Value/Garden
• Sleeps: 6
Guest Rating: 4.63/5
19 Guest Reviews
Limited-Time Offer: Stay before 10/22/16 and Save Up to 29%!
Jamaica Royale 91
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Only $300 to
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How long does it take you to walk 100 yards? Not very long at all. more info
Only 1 week left in the next 60 days!
• City: Siesta Key
• View: Best Value/Garden
• Sleeps: 6
Guest Rating: 4.51/5
45 Guest Reviews
Limited-Time Offer: Stay before 10/22/16 and Save Up to 29%!
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
Only 1 week left in the next 60 days!
• City: Siesta Key
• View: Best Value/Garden
• Sleeps: 4
New Property, Be One of Our First Guests!
Limited-Time Offer: Stay before 10/22/16 and Save Up to 29%!
Gulf & Bay Club: Bayside
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Only $300 to
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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 & Bay Bayside is irresistible! more info
Only 1 week left in the next 60 days!
• City: Siesta Key
• View: Best Value/Garden
• Sleeps: 6
Guest Rating: 4.67/5
15 Guest Reviews
Limited-Time Offer: Stay before 10/22/16 and Save Up to 29%!
Casa de Mariposa 5542
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Only $300 to
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Casa de Mariposa 5542 is a beautifully designed 3 bedroom, 3 bathroom home with a gulf view, heated pool and elevator in the coveted location directly across from the beach access to world famous Siesta Key beach and the Gulf of Mexico, boasting wonderful ... more info
Only 1 week left in the next 60 days!
• City: Siesta Key
• View: Ocean View
• Sleeps: 8
Guest Rating: 5/5
2 Guest Reviews
Limited-Time Offer: Stay before 10/22/16 and Save Up to 29%!
Siesta Dunes Beach 38A
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Only $300 to
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Do you have children who’ll delight in the geckos and insects they can discover in the garden? Or do you love nature and the sight and scents of tropical flowers? more info
Only 1 week left in the next 60 days!
• City: Siesta Key
• View: Best Value/Garden
• Sleeps: 6
Guest Rating: 4.49/5
71 Guest Reviews
Surfside Manor
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Only $300 to
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This beautiful paradise includes 3 bedrooms with shared heated pool and elevator overlooking the #1 beach in the USA. If you are looking for a private-feeling beach retreat just steps to the quartz sands of Siesta Beach and the turquoise waters of the ... more info
• City: Siesta Key
• View: Gulf View
• Sleeps: 8
New Property, Be One of Our First Guests!
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
New Property, Be One of Our First Guests!
Bay Tree Club 206C
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Only $300 to
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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
• City: Siesta Key
• View: Bay View
• Sleeps: 4
Guest Rating: 5/5
1 Guest Reviews
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