Winter Vacation Rentals & Cabin Rentals in Siesta Key, FL

Compare 14,550 available beachfront holiday vacation home properties, starts from $47

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ACCOMMODATION TYPES

Monthly & Short Term Winter Vacation Rentals in Siesta Key, FL: Top Deals

Crescent Street Villas by Beachside Management
Crescent Street Villas by Beachside Management
Crescent Street Villas by Beachside Management
Crescent Street Villas by Beachside Management
Crescent Street Villas by Beachside Management
Crescent Street Villas by Beachside Management
Crescent Street Villas by Beachside Management
4.0 (19 reviews)
Crescent Street Villas by Beachside Management
Hotel
$191 /night
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Tropical Breeze Resort
Tropical Breeze Resort
Tropical Breeze Resort
Tropical Breeze Resort
Tropical Breeze Resort
Tropical Breeze Resort
Tropical Breeze Resort
4.3 (252 reviews)
Tropical Breeze Resort
Resort
$117 /night
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SpringHill Suites Sarasota Bradenton
SpringHill Suites Sarasota Bradenton
SpringHill Suites Sarasota Bradenton
SpringHill Suites Sarasota Bradenton
SpringHill Suites Sarasota Bradenton
SpringHill Suites Sarasota Bradenton
SpringHill Suites Sarasota Bradenton
4.2 (111 reviews)
SpringHill Suites Sarasota Bradenton
Hotel
$80 /night
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Living the Dream by Beachside Management
Living the Dream by Beachside Management
Living the Dream by Beachside Management
Living the Dream by Beachside Management
Living the Dream by Beachside Management
Living the Dream by Beachside Management
4.5 (35 reviews)
Living the Dream by Beachside Management
Hotel
$197 /night
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Gulf Beach Resort Motel
Gulf Beach Resort Motel
Gulf Beach Resort Motel
Gulf Beach Resort Motel
Gulf Beach Resort Motel
Gulf Beach Resort Motel
Gulf Beach Resort Motel
4.0 (295 reviews)
Gulf Beach Resort Motel
Resort
$105 /night
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Newly Renovated Serenata Sarasota Condo
Newly Renovated Serenata Sarasota Condo
Newly Renovated Serenata Sarasota Condo
Newly Renovated Serenata Sarasota Condo
Newly Renovated Serenata Sarasota Condo
Newly Renovated Serenata Sarasota Condo
Newly Renovated Serenata Sarasota Condo
4.8 (7 reviews)
Newly Renovated Serenata Sarasota Condo
Condo
$90 /night
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2BR/1BA Vacation Rental - Sienna Park
2BR/1BA Vacation Rental - Sienna Park
2BR/1BA Vacation Rental - Sienna Park
2BR/1BA Vacation Rental - Sienna Park
2BR/1BA Vacation Rental - Sienna Park
2BR/1BA Vacation Rental - Sienna Park
2BR/1BA Vacation Rental - Sienna Park
4.8 (16 reviews)
2BR/1BA Vacation Rental - Sienna Park
Hotel
$70 /night
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Lantern Inn & Suites - Sarasota
Lantern Inn & Suites - Sarasota
Lantern Inn & Suites - Sarasota
Lantern Inn & Suites - Sarasota
Lantern Inn & Suites - Sarasota
Lantern Inn & Suites - Sarasota
Lantern Inn & Suites - Sarasota
4.0 (600 reviews)
Lantern Inn & Suites - Sarasota
Hotel
$78 /night
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Art Ovation Hotel, Autograph Collection
Art Ovation Hotel, Autograph Collection
Art Ovation Hotel, Autograph Collection
Art Ovation Hotel, Autograph Collection
Art Ovation Hotel, Autograph Collection
Art Ovation Hotel, Autograph Collection
Art Ovation Hotel, Autograph Collection
4.7 (463 reviews)
Art Ovation Hotel, Autograph Collection
Hotel
$139 /night
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Similar Inspirational Vacation Rental Destinations

Which Price Range Is Most Typical in Siesta Key, FL Area?
Vacation Condo & House Rental Price Information in Siesta Key, FL
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The graph shows the percentages of vacation homes in each price bucket. Siesta Key has the largest percentage (27.67%) of homes in $100 - $150 price range.
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What are some of the best activities, communities and places of interest for snowbirds in Siesta Key, FL?
Top Snowbirds-Friendly Places to Visit in Siesta Key, FL
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Siesta Key is an ideal destination for snowbirds looking for a warm winter climate. Located on Florida's Gulf Coast, this small barrier island offers plenty of sunshine, great shopping and restaurants, as well as proximity to healthcare facilities. For outdoor enthusiasts, there are several beaches to explore or take part in watersports like kayaking, fishing, and sailing. There are also numerous parks and golf courses in the area, perfect for those who prefer a more relaxed pace of life.

  • Sarasota Jungle Gardens

    This 10-acre tropical paradise features lush gardens, over 200 exotic birds, and alligators. Snowbirds can enjoy guided tours, bird shows, and a petting zoo during their visit.

  • Big Pass

    A shallow pass located between Lido Key and Siesta Key, Big Pass is the perfect spot for swimming, snorkeling, and spotting dolphins. Visitors can also try their luck at fishing from the shore.

  • The Stickney Point Bridge

    The Stickney Point Bridge is a great spot to watch sunsets. It's also popular among birdwatchers, as it's home to many species of migrating birds throughout the year.

How Many Accommodations Are Pets Allowed in Siesta Key, FL?
Pets Allowed vs Not Allowed in Siesta Key, FL
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22.43% of vacation homes in Siesta Key are pet friendly. Make sure you select the pet friendly home filter when you are going to bring your pet(s) for the upcoming vacation.
Best Tourist Attractions in Siesta Key, FL?
Destinations To Visit During the Winter in Siesta Key, FL
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How Many Airports in Siesta Key, FL?
Suggested Airports in Siesta Key, FL
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