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Search results; Over 1,000 homes in Siesta Key

Top guest favourite
Serviced apartment in Siesta Key
Siesta Key #1 Beach, pickle ball & tennis paradise
2 bedrooms, 4 beds, 2 private bathrooms
7–12 Aug
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4.99 out of 5 average rating, 216 reviews
Superhost
Home in Siesta Key
Bahama Mama | Tropical Retreat on Siesta Key
5 bedrooms, 7 beds, 5 bathrooms
20–25 Sept
5.0 out of 5 average rating, 4 reviews
Home in Siesta Key
House on Siesta Key with Private Pool and Hot tub!
4 bedrooms, 4 beds, 4 bathrooms
19–24 Aug
5.0 out of 5 average rating, 4 reviews
Superhost
Apartment in Sarasota
Direct Gulf View - Residence 505
4 bedrooms, 4.5 bathrooms
26–31 Aug
Top guest favourite
Home in Siesta Key
Steps to Siesta Key Beach! Sunset Balcony Views!
2 bedrooms, 3 beds, 1 bathroom
8–15 Aug
5.0 out of 5 average rating, 6 reviews
Home in Sarasota
The Siesta Key Retreat - An Island Garden Oasis!
4 bedrooms, 4 beds, 2 bathrooms
20–25 Jul
New place to stay
Apartment in Siesta Key
Pool & Beach access at Cozy Siesta Condo!
2 bedrooms, 1.5 bathrooms
1–6 Jul
New place to stay
Superhost
Home in Siesta Key
Villa Fiesta - 312
2 bedrooms, 3 beds, 1.5 bathrooms
6–11 Jul
New place to stay
Top guest favourite
Home in Sarasota
Luxury Pool Family Oasis-Siesta Beach Beac-3BR/2BA
3 bedrooms, 4 beds, 2 bathrooms
29 Aug – 3 Sept
4.96 out of 5 average rating, 137 reviews
Home in Sarasota
Palm Breeze Haven
4 bedrooms, 6 beds, 3 bathrooms
6–11 Jul
5.0 out of 5 average rating, 4 reviews
Apartment in Siesta Key
Newly Remodeled 2026-Just walk out on to the sand!
2 bedrooms, 3 beds, 2 bathrooms
15–20 Aug
Top guest favourite
Home in Siesta Key
Southern Exposure~2 Homes from Beach! Heated Pool!
6 bedrooms, 6 beds, 4 bathrooms
6–11 Jul
5.0 out of 5 average rating, 22 reviews
Guest favourite
Apartment in Siesta Key
Beach Rd, 300ft to Beach Access & 500ft to Village
1 bedroom, 2 beds, 1 bathroom
1–6 Aug
4.95 out of 5 average rating, 63 reviews
Top guest favourite
Home in Siesta Key
Completely Remodeled "Beach House on Siesta"
4 bedrooms, 6 beds, 2 bathrooms
5–11 Jul
5.0 out of 5 average rating, 27 reviews
Guest favourite
Home in Holmes Beach
Black Pearl! NEW! Block and half to Beach!
4 bedrooms, 5 beds, 4 bathrooms
5–12 Jul
4.89 out of 5 average rating, 9 reviews
Apartment in Siesta Key
2 Bedroom, 1 bath, sleeps 5 in Siesta Key #118
2 bedrooms, 3 beds, 1 bathroom
1–8 Jul
New place to stay
Home in Sarasota
Coastal Calm
3 bedrooms, 4 beds, 2 bathrooms
31 Jul – 7 Aug
5.0 out of 5 average rating, 3 reviews
Guest favourite
Home in Sarasota
4BRHeated Pool•Fire Pit•Pool Table Mins Siesta Key
4 bedrooms, 7 beds, 2 bathrooms
23–28 Aug
5.0 out of 5 average rating, 18 reviews
Top guest favourite
Home in Siesta Key
Siesta Key Beach Charmer
2 bedrooms, 3 beds, 1 bathroom
7–12 Jul
4.83 out of 5 average rating, 89 reviews