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Vacation Rentals in Siesta Key

Find the vacation rentals that appeal to you the most

The best vacation rentals in Siesta Key

Check out our selection of great vacation rentals in Siesta Key

Most booked vacation rentals in Siesta Key and surrounding area in the past month

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Popular with guests booking vacation rentals in Siesta Key

Scored out of 10, guest rating 6.0
Pleasant - What previous guests thought, 32 reviews

Popular with guests booking vacation rentals in Siesta Key

Scored out of 10, guest rating 8.8
Excellent - What previous guests thought, 22 reviews

Popular with guests booking vacation rentals in Siesta Key

Scored out of 10, guest rating 9.1
Wonderful - What previous guests thought, 27 reviews

Popular with guests booking vacation rentals in Siesta Key

Scored out of 10, guest rating 9.0
Wonderful - What previous guests thought, 23 reviews

Popular with guests booking vacation rentals in Siesta Key

Scored out of 10, guest rating 9.3
Wonderful - What previous guests thought, 20 reviews

Popular with guests booking vacation rentals in Siesta Key

Scored out of 10, guest rating 7.8
Good - What previous guests thought, 7 reviews

Popular with guests booking vacation rentals in Siesta Key

Scored out of 10, guest rating 8.6
Excellent - What previous guests thought, 56 reviews

Popular with guests booking vacation rentals in Siesta Key

Scored out of 10, guest rating 8.7
Excellent - What previous guests thought, 109 reviews

Popular with guests booking vacation rentals in Siesta Key

Scored out of 10, guest rating 8.2
Very Good - What previous guests thought, 54 reviews

Popular with guests booking vacation rentals in Siesta Key

Scored out of 10, guest rating 9.0
Wonderful - What previous guests thought, 207 reviews

Highly rated vacation rentals in Siesta Key and nearby

Scored out of 10, guest rating 8.4
Very Good - What previous guests thought, 680 reviews

Located just 1 minutes’ walk from the beach, this Siesta Key resort features a swimming pool. Guests can also enjoy access to free WiFi in common areas.

Scored out of 10, guest rating 8.7
Excellent - What previous guests thought, 395 reviews

Siesta Key Beachside Villas is located in the heart of Siesta Key. It features an outdoor pool and free WiFi. Beach access is a 2 minutes' walk from the property.

From $352.96 per night
Scored out of 10, guest rating 8.3
Very Good - What previous guests thought, 276 reviews

Spanning 2 city blocks and located just 1736 feet from Siesta Beach, Tropical Breeze Resort features two heated on-site pools and a spa. Guests will be 9.3 mi from Mote Marine Laboratory and Aquarium.

From $431.59 per night
Scored out of 10, guest rating 8.9
Excellent - What previous guests thought, 10 reviews

Sarasota Updated pool home, Near Siesta Key is located in Sarasota, just 10 miles from John and Mable Ringling Museum of Art and 10 miles from The John and Mable Ringling Museum of Art.

Scored out of 10, guest rating 9.1
Wonderful - What previous guests thought, 56 reviews

Florinda 3bdr/2bth 2car garage with New Pool is located in Sarasota, just 7.8 miles from The John and Mable Ringling Museum of Art and 4.2 miles from Sarasota Opera.

Scored out of 10, guest rating 8.8
Excellent - What previous guests thought, 22 reviews

Crescent Beach 1011 #1 is located in Sarasota, just 11 miles from The John and Mable Ringling Museum of Art and 12 miles from Sarasota International Convention Center.

From $446.68 per night
Scored out of 10, guest rating 8.9
Excellent - What previous guests thought, 65 reviews

3 miles to Siesta Key #1 Beach in America offers accommodations in Sarasota, 6.7 miles from Sarasota Opera and 6.8 miles from Marina Jack Restaurant And Marina.

From $277.72 per night
Scored out of 10, guest rating 9.1
Wonderful - What previous guests thought, 15 reviews

One Ocean - A 1101 is located in Sarasota, just a 2-minute walk from Crescent Beach and 11 miles from John and Mable Ringling Museum of Art. This 4-star vacation home offers a 24-hour front desk.

Vacation Rentals with swimming pools in Siesta Key and nearby

Scored out of 10, guest rating 9.0
Wonderful - What previous guests thought, 4 reviews

Offering a bar, MERMAID HOUSE WITH POOL JACUZZI STEPS to SIESTA KEY BEACH offers accommodations in Sarasota. This beachfront property offers access to a terrace, free private parking, and free Wifi.

From $834.97 per night
Scored out of 10, guest rating 10
Exceptional - What previous guests thought, 3 reviews

8.3 miles from The John and Mable Ringling Museum of Art in Sarasota, Siesta Key Waterfront Estate W Pool Privacy! offers accommodations with access to a fitness center.

Scored out of 10, guest rating 9.2
Wonderful - What previous guests thought, 49 reviews

Providing an outdoor swimming pool, Shiny oasis with lake view features accommodations in Sarasota.

From $329.87 per night
Scored out of 10, guest rating 9.4
Wonderful - What previous guests thought, 6 reviews

Offering a garden, Pool Home on Gulf Gate 5min away from Siesta Key provides accommodations in Sarasota. This property offers a private pool, free Wifi, and free private parking.

From $3,640 per night
Scored out of 10, guest rating 9.5
Exceptional - What previous guests thought, 20 reviews

Featuring pool with a view, 2BR/1BA Sienna Park Apartment offers accommodations in Sarasota. This apartment provides air-conditioned accommodations with a balcony and free Wifi.

From $386.40 per night
Scored out of 10, guest rating 8.9
Excellent - What previous guests thought, 14 reviews

1+1 Large condo Sarasota is located in Sarasota, just 11 miles from John and Mable Ringling Museum of Art and 11 miles from The John and Mable Ringling Museum of Art.

Scored out of 10, guest rating 7.7
Good - What previous guests thought, 43 reviews

13 miles from The John and Mable Ringling Museum of Art in Vamo, LUX VILLAs on beautiful Palmer Ranch features accommodations with access to a hot tub, fitness center, and open-air bath.

From $713.22 per night

Siesta Key Beach - Cape Aqua 5545 is located in Siesta Key, just a 10-minute walk from Siesta Key Beach and 11 miles from The John and Mable Ringling Museum of Art.

These vacation rentals in Siesta Key and nearby have options with free cancellation

Scored out of 10, guest rating 8.5
Very Good - What previous guests thought, 41 reviews

Entire Guesthouse 5 mins to Siesta Key & downtown is located in Sarasota, just 6.8 miles from The John and Mable Ringling Museum of Art and 3.3 miles from Sarasota Opera.

From $238.16 per night

The Sun Dial - 827

Siesta Key
Free cancellation options available

The Sun Dial - 827 offers accommodations in Siesta Key, 1.1 miles from Siesta Key Beach and 10 miles from The John and Mable Ringling Museum of Art.

Sand Dollar Cottage - 910

Siesta Key
Free cancellation options available

Sand Dollar Cottage - 910 offers accommodations in Siesta Key, a 15-minute walk from Siesta Key Beach and 11 miles from John and Mable Ringling Museum of Art.

Oasis on Siesta Key

Sarasota
Free cancellation options available

A 6-minute walk from Siesta Key Beach in Sarasota, Oasis on Siesta Key features accommodations with access to a fitness room.

Villa Champagne - 5322

Siesta Key
Free cancellation options available
Scored out of 10, guest rating 10
Exceptional - What previous guests thought, 1 review

Villa Champagne - 5322 is located in Siesta Key, just a 9-minute walk from Siesta Key Beach and 11 miles from The John and Mable Ringling Museum of Art.

Beach Palm Villa - 5533

Siesta Key
Free cancellation options available

Beach Palm Villa - 5533 is located in Siesta Key, just a 11-minute walk from Siesta Key Beach and 11 miles from John and Mable Ringling Museum of Art.

La Contento Casa - 5560

Siesta Key
Free cancellation options available
Scored out of 10, guest rating 8.0
Very Good - What previous guests thought, 1 review

La Contento Casa - 5560 is located in Siesta Key, just a 15-minute walk from Siesta Key Beach and 10 miles from The John and Mable Ringling Museum of Art.

Avenida Sanctuary

Siesta Key
Free cancellation options available
Scored out of 10, guest rating 10
Exceptional - What previous guests thought, 1 review

Avenida Sanctuary is located in Siesta Key, just a 4-minute walk from Siesta Key Beach and 11 miles from John and Mable Ringling Museum of Art. Guests can go for a swim in the private pool.

Enjoy breakfast in Siesta Key and nearby

Isla Amor - 86

Siesta Key
Breakfast options
Scored out of 10, guest rating 9.0
Wonderful - What previous guests thought, 1 review

Isla Amor - 86 is located in Siesta Key, just a 7-minute walk from Siesta Key Beach and 10 miles from The John and Mable Ringling Museum of Art.

Gulf Birdie - 5551 is located in Siesta Key, just a 15-minute walk from Siesta Key Beach and 10 miles from The John and Mable Ringling Museum of Art.

Central - Edgemere 738 is located in Siesta Key, just 10 miles from The John and Mable Ringling Museum of Art and 6 miles from Sarasota Opera. Guests may go for a swim in the private pool.

Scored out of 10, guest rating 8.0
Very Good - What previous guests thought, 1 review

Beach Way Getaway is located in Siesta Key, just 11 miles from John and Mable Ringling Museum of Art and 11 miles from The John and Mable Ringling Museum of Art.

Scored out of 10, guest rating 7.8
Good - What previous guests thought, 4 reviews

Our House at the Beach 604E By Beachside Management is located in Siesta Key, just a 6-minute walk from Siesta Key Beach and 10 miles from The John and Mable Ringling Museum of Art.

Our House at the Beach W-Tower 5th Fl offers accommodations in Siesta Key, a 6-minute walk from Siesta Key Beach and 11 miles from John and Mable Ringling Museum of Art.

Scored out of 10, guest rating 9.6
Exceptional - What previous guests thought, 6 reviews

Our House At The Beach, East Tower, 5th Fl offers accommodations in Siesta Key, a 6-minute walk from Siesta Key Beach and 11 miles from John and Mable Ringling Museum of Art.

Beach Walk Cottage - 451 offers accommodations in Siesta Key, a 6-minute walk from Siesta Key Beach and 10 miles from The John and Mable Ringling Museum of Art.

FAQ about vacation rentals in Siesta Key

Vacation Rentals That Guests Love in Siesta Key

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Scored out of 10, guest rating 8.7
Excellent - What previous guests thought, 22 reviews
Great location. Very close to trolley stops, within walking distance of the village and very easy access to beach.
Guest review by
Amanda
Young couple
Scored out of 10, guest rating 8.6
Excellent - What previous guests thought, 56 reviews
Property was in the perfect location! Close walk to the beach and the village! Perfect little beach house with an adorable pool!
Guest review by
Kristin
Family with young children
Scored out of 10, guest rating 9.0
Wonderful - What previous guests thought, 207 reviews
The place was perfect!!! Nice and clean. Close to Siesta Key Village and next to the beach. We stayed in cottage 1, and the outside shower was amazing. Have private sitting area and fish pond is right outside out front door. Definitely will be staying again.
Guest review by
Sandy
Travelers with friends
Scored out of 10, guest rating 8.3
Very Good - What previous guests thought, 20 reviews
My husband and I stayed here last November so knew what to expect. The beach wagon comes in so handy when walking to the village for groceries. Both times staying here the place was so clean!
Guest review by
Tisha
Family with young children
Scored out of 10, guest rating 7.2
Good - What previous guests thought, 27 reviews
Easy access to private beach, close to everything (in between siesta key village and downtown), easy to access, clean, more than adequate for vacation home, pools were never overcrowded and there were two.
Guest review by
Olivia
Family with young children