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Search results; Over 1,000 places in Siesta Key

Cottage in Siesta Key
Love Shack - steps away from #1 Beach in USA!
1 bed
Jun 1 – 6
4.83 out of 5 average rating, 144 reviews
Guest favorite
Guest suite in Siesta Key
Cozy Studio - 5 min walk to #1 Siesta Key Beach!
1 queen bed
Jun 1 – 6
4.92 out of 5 average rating, 133 reviews
Guest favorite
Condo in Siesta Key
Siesta Village Short Walk to Beach w heated Pool
2 beds
May 11 – 16
4.9 out of 5 average rating, 87 reviews
Guest favorite
Condo in Siesta Key
NO Stairs, beachfront & short walk to the village!
3 beds
Apr 27 – May 2
4.92 out of 5 average rating, 87 reviews
Guest favorite
Condo in Siesta Key
Cozy Siesta Key studio 5 minute walk to Village
1 king bed
Jun 25 – 30
4.89 out of 5 average rating, 151 reviews
Guest favorite
Vacation home in Siesta Key
Siesta Beach View : Pineapple Bungalow Efficiency
2 beds
Apr 28 – May 3
5.0 out of 5 average rating, 57 reviews
Guest favorite
Cottage in Siesta Key
Siesta Key Cozy Cottage across from the beach!
1 queen bed
Apr 28 – May 3
4.89 out of 5 average rating, 140 reviews
Guest favorite
Condo in Sarasota
#1 Beach Siesta Key Village w heated pool & arcade
2 beds
Apr 26 – May 1
5.0 out of 5 average rating, 7 reviews
Guest favorite
Apartment in Siesta Key
Across from beach & walk to town
3 beds
Apr 26 – May 1
5.0 out of 5 average rating, 15 reviews
Superhost
Cottage in Siesta Key
The Mermaid: Heated Pool, 4 Houses to Beach
1 king bed
May 3 – 8
4.91 out of 5 average rating, 90 reviews
Guest favorite
Home in Siesta Key
Lovely Siesta Key house near beach w/ heated pool!
3 beds
May 10 – 15
4.94 out of 5 average rating, 68 reviews
Cottage in Siesta Key
Cottage w/pool 1 block to village.close to beach
6 beds
Jun 29 – Jul 6
Guest favorite
Home in Siesta Key
Siesta Key Quaint Beach House
2 beds
Apr 23 – 28
4.98 out of 5 average rating, 65 reviews
Cottage in Siesta Key
Beach House by #1Siesta Key Beach!
2 beds
May 13 – 18
4.82 out of 5 average rating, 111 reviews
Guest favorite
Home in Siesta Key
Beachfront home with private access, walk to town!
5 beds
May 5 – 10
4.95 out of 5 average rating, 87 reviews
Guest favorite
Home in Siesta Key
Siesta Key, FL - Casa Berano
4 beds
Jul 21 – 28
4.89 out of 5 average rating, 104 reviews
Superhost
Home in Siesta Key
New Listing! 100% Private near Beach & Village.
6 beds
May 4 – 9
New place to stay
Guest favorite
Villa in Siesta Key
Siesta Key Pineapple Beach House Pool Beach view!
4 beds
May 4 – 9
5.0 out of 5 average rating, 43 reviews