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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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Siesta Key Island Rentals

Siesta Key

Siesta Key Island Rentals provides an indoor pool and air-conditioned accommodations in Siesta Key, a 4-minute walk from Siesta Key Beach.

K
Kelly
From
United States
Clean, great location, comfortable
Scored out of 10, guest rating 8.6
Excellent - What previous guests thought, 56 reviews
Price from
$442.98
1 night, 2 adults

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 8.1
Very Good - What previous guests thought, 53 reviews
Price from
$200
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, 37 reviews
Price from
$180
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
$183.33
1 night, 2 adults

Shiny oasis with lake view

Sarasota (Near Siesta Key)

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

R
R.H.
From
Canada
Anita's condo was very clean, fully equipped with everything that you need and more, and tastefully decorated. The location was great, and the lake view was admirably beautiful. It was very close to the beach. I will miss watching the turtles across the lake every morning, while eating my breakfast! We will definitely stay here again when we come back to Sarasota.
Scored out of 10, guest rating 9.2
Wonderful - What previous guests thought, 49 reviews
Price from
$170.15
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.

R
Rafee
From
United States
It is clean comfortable and amazing love this place this is my second time here and will definitely be back!
Scored out of 10, guest rating 9.3
Wonderful - What previous guests thought, 40 reviews
Price from
$185.25
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
$3,000
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 9.5
Exceptional - What previous guests thought, 20 reviews
Price from
$130
1 night, 2 adults

2BR/1BA Vacation Rental - Sienna Park

Sarasota (Near Siesta Key)

Offering a terrace, 2BR/1BA Vacation Rental - Sienna Park features accommodations in Sarasota.

M
Morty
From
United States
The puppy on outside was like ran down, but the inside of the place was totally remodeled. It was very comfortable
Scored out of 10, guest rating 9.2
Wonderful - What previous guests thought, 25 reviews
Price from
$120
1 night, 2 adults

2BR/2BA condo Sienna Park

Sarasota (Near Siesta Key)

2BR/2BA condo Sienna Park is a recently renovated apartment in Sarasota where guests can make the most of its outdoor swimming pool, garden, and barbecue facilities.

E
Edmond
From
United States
It was a great place to stay, very clean and comfortable! Eva - the owner - is very friendly and responsive. Close to shopping and to the famous Siesta Key Beach. Highly recommended!
Scored out of 10, guest rating 9.8
Exceptional - What previous guests thought, 8 reviews
Price from
$100
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, 30 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 9.0
Wonderful - What previous guests thought, 9 reviews

Popular with guests booking vacation rentals in Siesta Key

Scored out of 10, guest rating 7.9
Good - What previous guests thought, 66 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, 12 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 8.6
Excellent - What previous guests thought, 200 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 9.6
Exceptional - What previous guests thought, 10 reviews

Siesta Key Village-Suite #2: A block to the Beach! offers accommodations in Sarasota, a 4-minute walk from Siesta Key Beach and 1.3 miles from Crescent Beach.

From $374.21 per night
Scored out of 10, guest rating 8.6
Excellent - What previous guests thought, 5 reviews

Siesta Key Village-Suite #4: A block to the Beach! is located in Sarasota, just 6.1 miles from Sarasota Opera and 6.1 miles from Marina Jack Restaurant And Marina.

From $395.53 per night
Scored out of 10, guest rating 8.3
Very Good - What previous guests thought, 275 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 $356.92 per night
Scored out of 10, guest rating 9.2
Wonderful - What previous guests thought, 21 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 $401.24 per night
Scored out of 10, guest rating 9.1
Wonderful - 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 8.5
Very Good - What previous guests thought, 42 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
Scored out of 10, guest rating 9.3
Wonderful - What previous guests thought, 40 reviews

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.

Scored out of 10, guest rating 8.6
Excellent - What previous guests thought, 50 reviews

4 miles to Siesta Key Beach #1 in America is located in Sarasota, just 11 miles from The John and Mable Ringling Museum of Art and 7.1 miles from Sarasota Opera.

From $250.76 per night

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.

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.

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

Shiny oasis with lake view

Sarasota
Free cancellation options available
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 8.6
Excellent - What previous guests thought, 30 reviews

Bernice 3bd2bth With Heated Pool Near Siesta Key! offers accommodations in Sarasota, 11 miles from The John and Mable Ringling Museum of Art and 7.7 miles from Sarasota Opera.

From $487.24 per night

LUX VILLAs on beautiful Palmer Ranch

Vamo
Free cancellation options available
Scored out of 10, guest rating 7.7
Good - What previous guests thought, 44 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 $356.50 per night

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.

Beach Walk Cottage - 451

Siesta Key
Free cancellation options available

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.

Vacation Rentals with swimming pools in Siesta Key and nearby

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.

From $1,019.83 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.

Scored out of 10, guest rating 8.5
Very Good - What previous guests thought, 32 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 9.0
Wonderful - What previous guests thought, 1 review

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.

FAQ about vacation rentals in Siesta Key

Vacation Rentals That Guests Love in Siesta Key

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Avg. price/night: $388.39
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 7.3
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