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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

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Beautiful property on Siesta Key

Siesta Key

Providing an outdoor swimming pool, Beautiful property on Siesta Key features accommodations in Siesta Key. This villa provides air-conditioned accommodations with a patio.

J
Jacki
From
United States
Beautiful property. It had everything needed for a wonderful stay.
Scored out of 10, guest rating 8.0
Very Good - What previous guests thought, 56 reviews
Price from
JOD 141.730
1 night, 2 adults

Siesta Key Condo - on the water !

Siesta Key

Siesta Key Condo - on the water! is located in Siesta Key, just a 6-minute walk from Crescent Beach and 11 miles from The John and Mable Ringling Museum of Art.

D
Downes
From
United States
It's always such a pleasure to stay here.
Scored out of 10, guest rating 8.7
Excellent - What previous guests thought, 33 reviews
Price from
JOD 127.557
1 night, 2 adults

Siesta Key Beach House

Siesta Key

Siesta Key Beach House is a recently renovated villa in Siesta Key where guests can make the most of its outdoor swimming pool, free Wifi, private beach area, and water sports.

L
Lynn
From
United States
Paradise! An absolutely wonderful place to spend a week at the beach. All the comforts of home. Well cleaned upon arrival. Nothing can beat stepping out your bedroom sliding door into your very own tropical pool area. We enjoyed the birds visiting us everyday as we enjoyed having the pool all to ourselves. Would definitely return if it ever becomes available.
Scored out of 10, guest rating 8.0
Very Good - What previous guests thought, 66 reviews
Price from
JOD 238.106
1 night, 2 adults

Florinda 3bdr/2bth 2car garage with New Pool

Sarasota (Near Siesta Key)

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.

J
Julie
From
United States
The home was a perfect size for two couples traveling together. The location was perfect! Everything we had planned was within 15 minutes. The pool was a wonderful feature that we took advantage of. I was also impressed with the information given in the property description. Specifically that feather pillows are used in the bedrooms. I am allergic and was grateful that I was able to plan ahead and bring my own pillows instead of making an impromptu shopping trip.
Scored out of 10, guest rating 9.1
Wonderful - What previous guests thought, 58 reviews
Price from
JOD 282.751
1 night, 2 adults

* NEW * Serene Retreat / Private Patio & Pool *

Sarasota (Near Siesta Key)

* NEW * Serene Retreat / Private Patio & Pool * offers accommodations in Sarasota, a 19-minute walk from Crescent Beach and 10 miles from The John and Mable Ringling Museum of Art.

E
Evonne
From
United States
Great location. Quiet area. Fully stocked kitchen!!
Scored out of 10, guest rating 9.6
Exceptional - What previous guests thought, 6 reviews
Price from
JOD 129.917
1 night, 2 adults

House by Siesta Key

Sarasota (Near Siesta Key)

House by Siesta Key offers accommodations in Sarasota, 11 miles from The John and Mable Ringling Museum of Art and 7.1 miles from Sarasota Opera.

T
Tina
From
United States
The feel of being home. Clean and beautiful yet comfy and realistic
Scored out of 10, guest rating 9.2
Wonderful - What previous guests thought, 7 reviews
Price from
JOD 74.621
1 night, 2 adults

Close to beaches with hot tub and large garden

Sarasota (Near Siesta Key)

10 miles from The John and Mable Ringling Museum of Art in Sarasota, Close to beaches with hot tub and large garden provides accommodations with access to a hot tub.

G
Geoffrey
From
United States
Everything about the place was great - the location, the communication with the owners and the place itself was true to the description and the pictures. To have an outdoor space to ourselves was just amazing. And I liked the fact that it is close to everything yet located on a quiet small street away from the traffic.
Scored out of 10, guest rating 9.3
Wonderful - What previous guests thought, 39 reviews
Price from
JOD 131.277
1 night, 2 adults

Pool Home on Gulf Gate 5min away from Siesta Key

Sarasota (Near Siesta Key)

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.

Scored out of 10, guest rating 9.4
Wonderful - What previous guests thought, 6 reviews
Price from
JOD 2,125.950
1 night, 2 adults

Luxury Zen Den with heated pool just off Siesta Key

Sarasota (Near Siesta Key)

Luxury Zen Den with heated pool just off Siesta Key offers accommodations in Sarasota, 5.9 miles from Sarasota Opera and 5.9 miles from Marina Jack Restaurant And Marina.

P
Patricia
From
United States
The location was great. Very close to everything we were interested in.
Scored out of 10, guest rating 9.7
Exceptional - What previous guests thought, 31 reviews
Price from
JOD 199.839
1 night, 2 adults

2BR/1BA Sienna Park Apartment

Sarasota (Near Siesta Key)

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.

C
Cynthia
From
United States
Very clean! Kitchen had everything you need! Pool was great! Location good! Pool and beach supplies an A+ Communication was also extremely good!
Scored out of 10, guest rating 9.3
Wonderful - What previous guests thought, 20 reviews
Price from
JOD 92.125
1 night, 2 adults
All 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 9.1
Wonderful - What previous guests thought, 10 reviews

Popular with guests booking vacation rentals in Siesta Key

Scored out of 10, guest rating 8.7
Excellent - What previous guests thought, 107 reviews

Popular with guests booking vacation rentals in Siesta Key

Scored out of 10, guest rating 9.6
Exceptional - What previous guests thought, 14 reviews

Popular with guests booking vacation rentals in Siesta Key

Scored out of 10, guest rating 8.3
Very Good - What previous guests thought, 20 reviews

Popular with guests booking vacation rentals in Siesta Key

Scored out of 10, guest rating 8.7
Excellent - What previous guests thought, 58 reviews

Popular with guests booking vacation rentals in Siesta Key

Scored out of 10, guest rating 9.1
Wonderful - What previous guests thought, 26 reviews

Popular with guests booking vacation rentals in Siesta Key

Scored out of 10, guest rating 9.0
Wonderful - What previous guests thought, 209 reviews

Popular with guests booking vacation rentals in Siesta Key

Scored out of 10, guest rating 8.7
Excellent - What previous guests thought, 186 reviews

Popular with guests booking vacation rentals in Siesta Key

Scored out of 10, guest rating 8.0
Very Good - What previous guests thought, 66 reviews

Popular with guests booking vacation rentals in Siesta Key

Scored out of 10, guest rating 8.0
Very Good - What previous guests thought, 56 reviews

Enjoy breakfast in Siesta Key and nearby

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

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

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 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.

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.

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.

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.

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

Tropical Breeze Resort

Sarasota
Free cancellation options available
Scored out of 10, guest rating 8.5
Very Good - What previous guests thought, 287 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 JOD 263.518 per night

Florinda 3bdr/2bth 2car garage with New Pool

Sarasota
Free cancellation options available
Scored out of 10, guest rating 9.1
Wonderful - What previous guests thought, 58 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.

From JOD 496.227 per night

Shiny oasis with lake view

Sarasota
Free cancellation options available
Scored out of 10, guest rating 9.2
Wonderful - What previous guests thought, 48 reviews

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

Siesta Key Beach - Cape Aqua 5545

Siesta Key
Free cancellation options available

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.

Gulf Birdie - 5551

Siesta Key
Free cancellation options available

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

Siesta Key
Free cancellation options available

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.

Beach Way Getaway

Siesta Key
Free cancellation options available
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.

Vacation Rentals with swimming pools in Siesta Key and nearby

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 JOD 2,579.486 per night
Scored out of 10, guest rating 8.9
Excellent - What previous guests thought, 13 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.

From JOD 285.728 per night
Scored out of 10, guest rating 8.1
Very Good - What previous guests thought, 29 reviews

Clematis House near Arlington Park with Heated Pool offers accommodations in Sarasota, 6.9 miles from The John and Mable Ringling Museum of Art and 3 miles from Sarasota Opera.

Scored out of 10, guest rating 8.7
Excellent - What previous guests thought, 34 reviews

Our House at the Beach 502E By Beachside Management is located in Siesta Key, just a 6-minute walk from Siesta Key Beach and 11 miles from John and Mable Ringling Museum of Art.

A 11-minute walk from Siesta Key Beach in Siesta Key, Siesta Key Oasis with Outdoor Pool and Screened Lanai! features accommodations with access to a hot tub, spa center, and fitness room.

Lookout

Siesta Key
Swimming pool
Scored out of 10, guest rating 9.6
Exceptional - What previous guests thought, 8 reviews

Lookout is located in Siesta Key, just a 3-minute walk from Siesta Key Beach and 10 miles from The John and Mable Ringling Museum of Art.

Scored out of 10, guest rating 9.5
Exceptional - What previous guests thought, 2 reviews

Island Sun is located in Siesta Key, just a 2-minute walk from Siesta Key Beach and 10 miles from John and Mable Ringling Museum of Art.

Siesta Sun offers accommodations in Siesta Key, a 2-minute walk from Siesta Key Beach and 10 miles from The John and Mable Ringling Museum of Art.

Highly rated vacation rentals in Siesta Key and nearby

Scored out of 10, guest rating 9.2
Wonderful - What previous guests thought, 7 reviews

House by Siesta Key offers accommodations in Sarasota, 11 miles from The John and Mable Ringling Museum of Art and 7.1 miles from Sarasota Opera.

From JOD 231.250 per night
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.

Scored out of 10, guest rating 8.7
Excellent - What previous guests thought, 23 reviews

Our House at the Beach 501W 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.

Scored out of 10, guest rating 8.4
Very Good - What previous guests thought, 12 reviews

A Somewhere is Here by Beachside Management enjoys a location in Siesta Key, a 3-minute walk from Siesta Key Beach and 10 miles from The John and Mable Ringling Museum of Art.

Scored out of 10, guest rating 9.4
Wonderful - What previous guests thought, 7 reviews

Ocean Vue By Beachside Management offers accommodations in Siesta Key, a few steps from Siesta Key Beach and 11 miles from John and Mable Ringling Museum of Art.

Scored out of 10, guest rating 9.0
Wonderful - What previous guests thought, 20 reviews

Siesta Key Beach 665 #1 offers accommodations in Siesta Key, 10 miles from The John and Mable Ringling Museum of Art and 6.8 miles from Sarasota Opera.

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

Siesta Key Beach - Capri 665 #4 offers accommodations in Siesta Key, a few steps from Siesta Key Beach and 11 miles from John and Mable Ringling Museum of Art.

Scored out of 10, guest rating 8.5
Very Good - What previous guests thought, 26 reviews

Siesta Key Beach - Tropea 665 #3 offers accommodations in Siesta Key, a few steps 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 8.8
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 8.7
Excellent - What previous guests thought, 58 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, 209 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, 26 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