Villas in Siesta Key

October 2026
November 2026

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Next weekend
Oct 2 - Oct 4
In two weeks
Oct 9 - Oct 11
In one month
Oct 23 - Oct 25
In two months
Nov 20 - Nov 22
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Recommended hotels in Siesta Key

1. Spark by Hilton Sarasota Siesta Key Gateway

Spark by Hilton Sarasota Siesta Key Gateway
Sarasota
$93
$106 total
includes taxes & fees
Sep 24 - Sep 25
Spark by Hilton Sarasota Siesta Key Gateway

2. Siesta Key Beach Resort and Suites

Siesta Key Beach Resort and Suites
Siesta Key Village
$146
$220 total
includes taxes & fees
Sep 23 - Sep 24
Siesta Key Beach Resort and Suites

3. Tropical Beach Resorts

Tropical Beach Resorts
South Village
$135
$179 total
includes taxes & fees
Sep 27 - Sep 28
Tropical Beach Resorts

4. Tropical Breeze Resort

Tropical Breeze Resort
Siesta Key Village
$165
$209 total
includes taxes & fees
Sep 28 - Sep 29
Tropical Breeze Resort

5. Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key
Sarasota
$116
$131 total
includes taxes & fees
Sep 23 - Sep 24
Hibiscus Suites - Gateway to Siesta Key

6. SeaSpray Resort

SeaSpray Resort
Siesta Key
$224
$253 total
includes taxes & fees
Sep 23 - Sep 24
SeaSpray Resort

7. Siesta Key Beachside Villas

Siesta Key Beachside Villas
Siesta Key Village
$158
$234 total
includes taxes & fees
Sep 23 - Sep 24
Siesta Key Beachside Villas

8. Captiva Beach Resort

Captiva Beach Resort
South Village
$162
$199 total
includes taxes & fees
Sep 23 - Sep 24
Captiva Beach Resort

9. Twin Palms at Siesta

Twin Palms at Siesta
Siesta Key
$219
$247 total
includes taxes & fees
Oct 1 - Oct 2
Twin Palms at Siesta

10. Siesta Key Palms Resort

Siesta Key Palms Resort
Sarasota
$55
$113 total
includes taxes & fees
Sep 28 - Sep 29
Siesta Key Palms Resort

11. Cottages at Siesta Key Inn

Cottages at Siesta Key Inn
South Village
$95
$120 total
includes taxes & fees
Sep 23 - Sep 24
Cottages at Siesta Key Inn

12. Siesta Key Inn

Siesta Key Inn
South Village
$131
$165 total
includes taxes & fees
Sep 28 - Sep 29
Siesta Key Inn

13. Siesta Palms By the Beach

Siesta Palms By the Beach
South Village
$136
$238 total
includes taxes & fees
Sep 28 - Sep 29
Siesta Palms By the Beach

14. Tiny House Siesta

Tiny House Siesta
Sarasota
$64
$208 total
includes taxes & fees
Oct 5 - Oct 6
Tiny House Siesta

15. Azul Resort

Azul Resort
South Village
$82
$93 total
includes taxes & fees
Sep 23 - Sep 24
Azul Resort

16. Turtle Beach Resort

Turtle Beach Resort
Siesta Key
$221
$279 total
includes taxes & fees
Sep 24 - Sep 25
Turtle Beach Resort

17. Siesta Key Island Rentals

Siesta Key Island Rentals
Siesta Key
$103
$325 total
includes taxes & fees
Sep 30 - Oct 1
Siesta Key Island Rentals

18. Siesta Vibe Pool Walk To Crescent Beach

Siesta Vibe Pool Walk To Crescent Beach
South Village
$119
$390 total
includes taxes & fees
Sep 23 - Sep 24
Siesta Vibe Pool Walk To Crescent Beach

19. Siesta Heron Suites & Villas

Siesta Heron Suites & Villas
Siesta Key
$97
$310 total
includes taxes & fees
Sep 23 - Sep 24
Siesta Heron Suites & Villas

20. Lulu's Key House Leatherback 2/2 Downstairs

Lulu's Key House Leatherback 2/2 Downstairs
Siesta Key Village
$313
$721 total
includes taxes & fees
Oct 10 - Oct 11
Lulu's Key House Leatherback 2/2 Downstairs
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Top neighborhoods in Siesta Key

Siesta Key Village

Siesta Key Village feels like a tropical daydream with tiki bars and surf shops surrounding America's top-rated beach. You'll find sugar-white sand just steps from colorful boutiques, while live music drifts through palm-lined streets. Sunset cocktails flow as freely as the Gulf breeze at open-air restaurants where fresh grouper sandwiches are practically required eating. Getting around is easy on foot within the compact village core, though many visitors rent golf carts for style points. Vacation rentals and boutique hotels dominate the accommodation scene, most offering beach gear and those essential sunset views. When night falls, the village lights up with beachfront dining and steel drum soundtracks.

Bay Island

Bay Island offers an exclusive slice of paradise on Siesta Key with direct access to award-winning beaches and stunning Gulf views. This peaceful residential enclave features luxury waterfront properties with private docks, perfect for beach lovers and boating enthusiasts. You'll be just minutes from the powdery white sands that made Siesta Key famous and close to Shell Beach and Lido Beach. Dining requires a short drive to nearby Siesta Key Village or Sarasota for fresh seafood and upscale restaurants. Accommodation options focus on high-end vacation rentals with premium amenities like private pools. A rental car is essential for exploring the area's attractions, including Marie Selby Botanical Gardens and St. Armands Circle.

South Village

Siesta Key's South Village neighborhood is home to attractions such as Safe Harbor Siesta Key and Crescent Beach.

Aloha Kai

Aloha Kai delivers pristine beach access without the tourist crowds of busier Siesta Key spots. The neighborhood sits between sugar-white Siesta Key Beach and tranquil intracoastal waters, giving you the best of both worlds. Crystal-clear Gulf waters invite swimming year-round, while the neighborhood's peaceful streets and tropical landscaping create a true vacation vibe. Most accommodations offer luxury vacation rentals with private pools and Gulf views. You'll find limited dining within the neighborhood, but Siesta Key Village is just a 10-minute drive away. The flat terrain makes for easy walking and biking, while rental cars are recommended for exploring beyond this peaceful beachfront haven.

Top landmarks in Siesta Key

A lifeguard tower with an American flag, a green flag, and a signboard on a beach with people sunbathing and umbrellas.

Siesta Key Beach

9.6/10 (4,113 reviews)
If being by the water is a major draw, Siesta Key Beach is one of the most popular seaside spots located 0.9 mi (1.5 km) from central Siesta Key. Enjoy the sunset by the shore at Lido Beach, Crescent Beach, and Shell Beach.
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A sandy beach with people sunbathing and umbrellas, clear blue sky, and calm sea.

Turtle Beach

9.0/10 (1,163 reviews)
Whether you want to collect beach glass or watch the sunset, Turtle Beach is a spot you might want to check out, located 4.4 mi (7.1 km) from central Siesta Key. If you want to continue walking by the waves, head to Siesta Key Beach and Crescent Beach.
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A sunset over the ocean with silhouettes of people and tall grasses.

Crescent Beach

9.4/10 (815 reviews)
If you can't wait to get to the beach, you might enjoy a trip to Crescent Beach located 2.3 mi (3.8 km) from central Siesta Key. Enjoy the sunset by the shore at Siesta Key Beach, Lido Beach, and Turtle Beach.
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A beach with a pier, palm trees, and calm ocean waters under a clear sky.

Point of Rocks

9.2/10 (444 reviews)
Point of Rocks is 2.7 mi (4.3 km) from central Siesta Key, why not stop by during your stay. Why not take a stroll along the beaches and watch the sunset while you're here? Want to stretch your legs some more? Head to Siesta Key Beach Playground and South Lido Park, both nearby.
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A marina with boats docked, a clear sky, and a palm tree.

Safe Harbor Siesta Key

9.2/10 (709 reviews)
You can stroll along Safe Harbor Siesta Key for relaxing water views when you're in South Village. If you carry on walking you'll get to Crescent Beach for some more water views.
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A coastal town with a beach, marina, and residential area.

Shell Beach

9.2/10 (164 reviews)
Whether you want to hunt for sand dollars or smell the fresh air, Shell Beach is a spot you might want to check out, located 1.6 mi (2.6 km) from central Siesta Key. If you want to continue walking by the waves, head to Irma Beach located nearby.
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A beach with people sunbathing, umbrellas, and beach chairs.

Jim Neville Marine Preserve

8.8/10 (71 reviews)
Jim Neville Marine Preserve is 5.5 mi (8.9 km) from central Siesta Key, why not stop by during your stay. Why not take a stroll along the beaches and watch the sunset while you're here?
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Siesta Key Beach Playground

Siesta Key Beach Playground is 1.1 mi (1.7 km) from central Siesta Key, why not stop by during your stay. Want to stretch your legs some more? Head to Point of Rocks and Marie Selby Botanical Gardens, both nearby.
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Learn more about Siesta Key

Barefoot luxury awaits on beaches where the sand feels like powdered sugar between your toes. Siesta Key Beach consistently ranks among America's finest, with quartz sand that stays cool even under the Florida sun. Kayak through mysterious mangrove tunnels where manatees and dolphins make surprise appearances in crystal-clear waters. The village offers beachside dining where seafood arrives fresh from Gulf waters to your plate. Crescent Beach provides a quieter alternative when the main strand gets crowded. Live music creates the soundtrack for spectacular sunsets that paint the sky in impossible colors. Nearby Turtle Beach offers excellent shelling opportunities without the crowds. For a change of scenery, hop over to Lido Beach where the shoreline curves gracefully along the Gulf's edge.

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A yellow lifeguard tower with an American flag on a beach with people and umbrellas.

About the destination

Siesta Key is a relaxing place known for its beaches. Beachcombers can spend the day at Siesta Key Beach when the weather is nice. Popular sights in the surrounding area include Lido Beach.