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Search results; Over 1,000 homes in Siesta Key

Guest favourite
Apartment in Siesta Key
Enchanting Coastal Ambiance & Breathtaking Sunsets
1 bedroom, 1 bed, 1 bathroom
12–17 Sept
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4.89 out of 5 average rating, 106 reviews
Top guest favourite
Home in Siesta Key
Steps to Siesta Key Beach! Sunset Balcony Views!
2 bedrooms, 3 beds
26 Sept – 1 Oct
5.0 out of 5 average rating, 13 reviews
Top guest favourite
Apartment in Siesta Key
Private Beach•3 Heated Pools•2BR•Ground Floor
2 bedrooms, 3 beds
28 Nov – 3 Dec
5.0 out of 5 average rating, 8 reviews
Guest favourite
Apartment in Siesta Key
Spacious 2-Floor, 2BR, 2.5BA Condo Near Everything
2 bedrooms, 4 beds
16–21 Sept
4.88 out of 5 average rating, 177 reviews
Top guest favourite
Villa in Siesta Key
Renovated Siesta Key Villa+Private Beach+3 Pools
1 bedroom, 3 beds
20–25 Sept
5.0 out of 5 average rating, 15 reviews
Guest favourite
Apartment in Siesta Key
The Flamingo's Nest at Sea Club II
2 bedrooms, 3 beds
26 Sept – 1 Oct
4.94 out of 5 average rating, 156 reviews
Top guest favourite
Flat in Siesta Key
Siesta Key Paradise - Steps to Beach & Village
3 bedrooms, 4 beds
14–19 Sept
5.0 out of 5 average rating, 12 reviews
Top guest favourite
Flat in Siesta Key
Beach Walk Bungalow
3 bedrooms, 3 beds
3–8 Oct
4.94 out of 5 average rating, 35 reviews
Top guest favourite
Home in Siesta Key
Siesta Key Retreat 1mi to Beach!
3 bedrooms, 4 beds
12–19 Sept
4.96 out of 5 average rating, 48 reviews
Top guest favourite
Apartment in Siesta Key
New listing - Pool Home, 500ft to Beach!
3 bedrooms, 7 beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 16 reviews
Top guest favourite
Flat in Siesta Key
Siesta Premier Location - The 'Calm of Siesta'
2 bedrooms, 2 beds
18–25 Sept
4.94 out of 5 average rating, 142 reviews
Top guest favourite
Townhouse in Siesta Key
Gulf and Beach Views-Steps from Beach and Village
2 bedrooms, 2 beds
26 Oct – 2 Nov
5.0 out of 5 average rating, 49 reviews
Luxe
Home in Siesta Key
7Bedroom Luxury Home W/Private Pool on Siesta Key!
7 bedrooms, 10 beds
12–17 Sept
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Apartment in Siesta Key
Siesta Key Beach front 2 bedroom condo w/ parking
2 bedrooms, 2 queen beds
10–17 Oct
4.97 out of 5 average rating, 63 reviews
Guest favourite
Home in Sarasota
Sun Coast Oasis-Heated Pool-Pool Table-Arcade
3 bedrooms, 5 beds
21–26 Sept
5.0 out of 5 average rating, 9 reviews
Guest favourite
Apartment in Siesta Key
Siesta Key condo - short walk to beach - GBB 1219
2 bedrooms, 3 beds
15–22 Sept
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Apartment in Siesta Key
Beachfront Siesta Key - 3 night min w/beach gear!
2 bedrooms, 4 beds
14–19 Nov
4.99 out of 5 average rating, 75 reviews
Guest favourite
Chalet in Siesta Key
Beach Rd, 300ft to Beach Access & 500ft to Village
2 bedrooms, 4 beds
12–17 Sept
4.93 out of 5 average rating, 60 reviews
Top guest favourite
Home in Sarasota
Haven on Helene pool house.
3 bedrooms, 4 beds
12–17 Sept
4.97 out of 5 average rating, 73 reviews