The 10 best vacation homes in Siesta Key, US | Booking.com
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Vacation Homes in Siesta Key

Find the vacation homes that appeal to you the most

The best vacation homes in Siesta Key

Check out our selection of great vacation homes in Siesta Key

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Siesta Key Island Rentals

Siesta Key

Siesta Key Island Rentals in Siesta Key provides accommodations with an indoor pool, a garden, and a tennis court. With pool views, this accommodation provides a swimming pool.

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

Poolside Paradise Near Siesta Key Beach

Sarasota (Near Siesta Key)

Poolside Paradise Near Siesta Key Beach is located in Sarasota, just 13 miles from Sarasota International Convention Center and 8.3 miles from Marina Jack Restaurant And Marina.

S
Saralee
From
United States
Perfect home for us during our vacation. Beds are comfy, everything you could need in the kitchen, pool felt great, kids love ping pong, love the decor and overall feel of the home. Location was convenient for beach days, shopping and any meals out. We really loved our stay!!
Scored out of 10, guest rating 9.4
Wonderful - What previous guests thought, 5 reviews
Price from
$392.32
1 night, 2 adults

2bed/2bath Condo next to Siesta Key ~A Hidden Gem

Sarasota (Near Siesta Key)

2bed/2bath Condo next to Siesta Key ~A Hidden Gem offers accommodations in Sarasota, a 19-minute walk from Crescent Beach and 10 miles from The John and Mable Ringling Museum of Art.

B
Bob
From
United States
Of the best outfitted condos I have ever stayed at. Had everything I needed, and even had a 'happy cabinet' above the stove. Very easy 5 minute walk to the main strip. I also Loved the bikes. I rode the larger bike around town and to the beach and very much appreciated having it there for my use!(tire pump was in kitchen closet). Great place to stay in Siesta Key!
Scored out of 10, guest rating 9.3
Wonderful - What previous guests thought, 27 reviews
Price from
$148.50
1 night, 2 adults

5min from the beach 8 min from Siesta Key

Sarasota (Near Siesta Key)

5min from the beach 8 min from Siesta Key offers accommodations in Sarasota, 11 miles from The John and Mable Ringling Museum of Art and 7.3 miles from Sarasota Opera.

E
Edila
From
United States
near to the good market & beach
Scored out of 10, guest rating 9.0
Wonderful - What previous guests thought, 20 reviews
Price from
$198
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

Tiny House Siesta

Sarasota (Near Siesta Key)

Tiny House Siesta offers self-catering tiny houses in Sarasota, Florida. Features include a kitchenette, TV, and free WiFi. Siesta Key is less than 1 km away and Siesta Key Beach is 1.6 km away.

A
Amanda
From
Canada
Cleanliness, parking, entry code and location
Scored out of 10, guest rating 8.3
Very Good - What previous guests thought, 636 reviews
Price from
$101
1 night, 2 adults

Siesta Key Beachside Villas

Sarasota (Near Siesta Key)

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.

s
sylvia
From
Brazil
This is the perfect place for a family vacation! It is right next to the beach, they have beach chairs and even though they don’t offer beach umbrellas, they have lots of them left from previous guests that they are more than welcome to lend you! Staff is extra nice and always there to help. There are bikes that you can use all day long, no cost! It is right next to the local stores, walking distance to every restaurant or bar! Our room had a kitchen/living room which was perfect because we had our 5 yr old son with us and the kitchen made it easy to arrange breakfast and dinner
Scored out of 10, guest rating 8.7
Excellent - What previous guests thought, 396 reviews
Price from
$228.33
1 night, 2 adults

Siesta Key Beach Resort and Suites

Sarasota (Near Siesta Key)

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.

C
Crystal
From
United States
The location is perfect a short walk across the street to the beach access and minutes to walk to the Village where all the shopping and restaurants are . Live music daily … bottled water and coffee is free which is a plus ! Everything you need for the beach - chairs , cooler and beach towels!! We just loved the live music with Casey on the Key , she was so much fun and was great! I can’t think of anything we didn’t love about it . This was my 3rd time staying here and hope to be back soon .
Scored out of 10, guest rating 8.3
Very Good - What previous guests thought, 682 reviews
Price from
$286.25
1 night, 2 adults

Sarasota Updated pool home, Near Siesta Key

Sarasota (Near Siesta Key)

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.

D
Dona
From
United States
We loved that there was enough room for all of us. The decor was very nice.
Scored out of 10, guest rating 8.9
Excellent - What previous guests thought, 10 reviews
Price from
$546.70
1 night, 2 adults
All vacation homes in Siesta Key

Looking for a vacation home?

Great for families or large parties, vacation homes are privately owned accommodations, available for long or short-term rental. These homes are furnished and equipped with kitchen facilities, though breakfast might be offered as an add-on. These properties have their own independent front door, which makes them different than apartments.

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

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Save money on vacation homes in Siesta Key and nearby – budget options available

  • Tiny House Siesta

    Sarasota
    Budget options available
    Scored out of 10, guest rating 8.3
    Very Good - What previous guests thought, 636 reviews

    Tiny House Siesta offers self-catering tiny houses in Sarasota, Florida. Features include a kitchenette, TV, and free WiFi. Siesta Key is less than 1 km away and Siesta Key Beach is 1.6 km away.

    From $167.24 per night
  • Tiny House Pirate Ship - Sleeps 2 near Siesta Key beach offers accommodations in Siesta Key, 10 miles from John and Mable Ringling Museum of Art and 10 miles from The John and Mable Ringling Museum of...

    From $161.98 per night
  • Scored out of 10, guest rating 10.0
    Exceptional - What previous guests thought, 1 review

    Offering a garden, Cute 3/2 Siesta home steps from Siesta waters offers accommodations in Sarasota. Both Wifi and private parking are accessible at the vacation home free of charge.

    From $357.81 per night
  • The Sun Dial - 827

    Siesta Key
    Budget 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
    Budget 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
    Budget options available

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

  • Siesta Dreamin'

    Siesta Key
    Budget options available

    Siesta Dreamin' offers accommodations in Siesta Key, a 15-minute walk from Siesta Key Beach and 10 miles from John and Mable Ringling Museum of Art.

  • Villa Champagne - 5322

    Siesta Key
    Budget options available
    Scored out of 10, guest rating 10.0
    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.

Enjoy breakfast in Siesta Key and nearby

  • 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.

  • Siesta Key Paradise, Vacation Pool Home, Near Beach, Restaurants and More offers accommodations in Sarasota, 10 miles from John and Mable Ringling Museum of Art and 10 miles from The John and Mable...

  • Bikini Tini Time offers accommodations in Siesta Key, a 14-minute walk from Siesta Key Beach and 10 miles from 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.

  • Poseidons Palace offers accommodations in Siesta Key, a 5-minute walk from Siesta Key Beach and 11 miles from John and Mable Ringling Museum of Art.

  • Cape Aqua

    Siesta Key
    Breakfast options

    Cape Aqua is located in Siesta Key, just 12 miles from Sarasota International Convention Center and 7.3 miles from Marina Jack Restaurant And Marina.

  • 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.

Great access to the city center. Check these vacation homes in Siesta Key and nearby

  • 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.

  • Edgemere

    Siesta Key
    Central location

    Edgemere is located in Siesta Key, just 10 miles from The John and Mable Ringling Museum of Art and 11 miles from Sarasota International Convention Center.

  • Surf's Up

    Siesta Key
    Central location

    Providing massage services, Surf's Up offers accommodations in Siesta Key. This property offers access to a balcony, free private parking, and free Wifi.

  • New Listing! Spacious, 100 percent Private, near the Siesta Key Beach and Village!

  • Blue Wave

    Siesta Key
    Central location

    Offering massage services, Blue Wave offers accommodations in Siesta Key. This property offers a private pool, free Wifi, and free private parking.

  • Providing massage services, Cape Aqua Retreat provides accommodations in Siesta Key. This property offers a private pool, free Wifi, and free private parking.

  • Casa Blanca

    Siesta Key
    Central location

    A 18-minute walk from Siesta Key Beach in Siesta Key, Casa Blanca offers accommodations with access to a sauna.

Vacation Homes with swimming pools in Siesta Key and nearby

  • 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.

    From $578 per night
  • 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 10.0
    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 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.

  • Scored out of 10, guest rating 7.8
    Good - What previous guests thought, 45 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
  • Offering massage services, Crescent Royale 515 offers accommodations in Siesta Key.

  • Featuring massage services, Crescent Royale 105 features accommodations in Siesta Key.

FAQ about vacation homes in Siesta Key

Vacation Homes That Guests Love in Siesta Key

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  • Scored out of 10, guest rating 7.9
    Good - What previous guests thought, 66 reviews
    The house is in a beautiful, peaceful and tranquil setting. A fresh, clean scent was very noticeable upon opening the door on arrival. The house was very clean. Pool off slider of master bedroom was perfect for swimming later in the day when it was too hot to be at the beach. Great water pressure in master shower. Great location for taking the trolley to Siesta Key Village for dinner.
    Guest review by
    Lynn
    Family with young children
  • Scored out of 10, guest rating 9.5
    Exceptional - What previous guests thought, 4 reviews
    Spacious waterfront property within walking distance of the beach. Felt miles away from the traffic and crowds. So many extras from cupcakes upon arrival, to all the things needed for a day at the beach. Modern, updated and very clean. Will recommend and return!!
    Guest review by
    Jennifer
    Solo traveler
  • Avg. price/night: $438.56
    Scored out of 10, guest rating 8.5
    Very Good - What previous guests thought, 202 reviews
    Very clean.. close to the main beaches and it is comfortable...
    Guest review by
    José Roberto
    Family with young children