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Search results; Over 1,000 homes in Siesta Key

Guest favourite
Apartment in Siesta Key
Siesta Key Condo. Checkout our great rates!
2 bedrooms, 4 beds, 1.5 private bathrooms
5–12 Sept
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4.96 out of 5 average rating, 135 reviews
Superhost
Home in Siesta Key
Bahama Mama | Tropical Retreat on Siesta Key
5.0 out of 5 average rating, 4 reviews, 5 bedrooms, 7 beds, 5 bathrooms
20–25 Sept
Home in Siesta Key
House on Siesta Key with Private Pool and Hot tub!
5.0 out of 5 average rating, 5 reviews, 4 bedrooms, 4 beds, 4 bathrooms
19–24 Aug
Superhost
Home in Siesta Key
Villa Fiesta - 312
New place to stay, 2 bedrooms, 3 beds, 1.5 bathrooms
6–11 Jul
Apartment in Siesta Key
Pool & Beach access at Cozy Siesta Condo!
New place to stay, 2 bedrooms, 1.5 bathrooms
1–6 Jul
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!
5.0 out of 5 average rating, 6 reviews, 2 bedrooms, 3 beds, 1 bathroom
8–15 Aug
Home in Sarasota
The Siesta Key Retreat - An Island Garden Oasis!
New place to stay, 4 bedrooms, 4 beds, 2 bathrooms
20–25 Jul
Guest favourite
Home in Holmes Beach
Black Pearl! NEW! Block and half to Beach!
4.89 out of 5 average rating, 9 reviews, 4 bedrooms, 5 beds, 4 bathrooms
5–12 Jul
Guest favourite
Apartment in Siesta Key
Beach Rd, 300ft to Beach Access & 500ft to Village
4.95 out of 5 average rating, 63 reviews, 1 bedroom, 2 beds, 1 bathroom
1–6 Aug
Guest favourite
Home in Sarasota
LA Luxury & Heated Pool Oasis 12 min to Siesta Key
5.0 out of 5 average rating, 8 reviews, 4 bedrooms, 2 beds, 3 bathrooms
27 Jul – 1 Aug
Top guest favourite
Home in Siesta Key
Southern Exposure~2 Homes from Beach! Heated Pool!
5.0 out of 5 average rating, 22 reviews, 6 bedrooms, 6 beds, 4 bathrooms
6–11 Jul
Apartment in Siesta Key
2 Bedroom, 1 bath, sleeps 5 in Siesta Key #118
New place to stay, 2 bedrooms, 3 beds, 1 bathroom
1–8 Jul
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
Completely Remodeled "Beach House on Siesta"
5.0 out of 5 average rating, 27 reviews, 4 bedrooms, 6 beds, 2 bathrooms
5–11 Jul
Home in Sarasota
Palm Breeze Haven
5.0 out of 5 average rating, 5 reviews, 4 bedrooms, 6 beds, 3 bathrooms
6–11 Jul
Superhost
Home in Sarasota
6630 - Mira Bella
New place to stay, 4 bedrooms, 10 beds, 4 bathrooms
5–10 Aug
Top guest favourite
Home in Sarasota
Books Tide Retreat - minutes from Siesta Beach
4.96 out of 5 average rating, 53 reviews, 2 bedrooms, 2 beds, 2 bathrooms
30 Jul – 4 Aug
Home in Siesta Key
Waterfront Home Pool & Dock 5 Min to Siesta Beach
5.0 out of 5 average rating, 3 reviews, 3 bedrooms, 4 beds, 2 bathrooms
3–10 Aug