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Search results; Over 1,000 homes in Siesta Key

Guest favourite
Bungalow in Siesta Key
Heated Pool, Dock, Kayaks, 1-mile to Turtle Beach
1 bedroom, 2 beds, 1 private bathroom
1–6 Sept
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5.0 out of 5 average rating, 35 reviews
Top guest favourite
Villa in Siesta Key
Renovated Siesta Key Villa+Private Beach+3 Pools
1 bedroom, 3 beds
9–14 Sept
5.0 out of 5 average rating, 9 reviews
Villa in Siesta Key
Aloha Kai Villa 52S - Premium Siesta Key Beach
3 bedrooms, 6 beds
1–6 Sept
Superhost
Chalet in Siesta Key
Beach Rd, 300ft to Beach Access & 500ft to Village
2 bedrooms, 3 beds
1–6 Sept
New place to stay
Guest favourite
Apartment in Siesta Key
Penthouse 20ft to Beach Access, 500ft from Village
3 bedrooms, 7 beds
19–24 Sept
4.89 out of 5 average rating, 47 reviews
Apartment in Siesta Key
Jamaica Royale 099 Nice Gulf side unit!
2 bedrooms, 5 beds
1–6 Sept
Flat in Siesta Key
Villa with private beach, 3 pools complex on beach
2 bedrooms, 3 beds
13–19 Sept
New place to stay
Top guest favourite
Bungalow in Sarasota
FlipFlopsOn III • ½ Mile Siesta Key • Walk to Bay
2 bedrooms, 4 beds
24–31 Oct
5.0 out of 5 average rating, 11 reviews
Top guest favourite
Home in Sarasota
Coastal Luxe, SaltPool/heatSpa, 5 miles to Siesta
5 bedrooms, 10 beds
7–14 Sept
4.98 out of 5 average rating, 49 reviews
Home in Siesta Key
3BR waterfront pool home, family friendly, WIFI
3 bedrooms, 5 beds
1–8 Sept
Flat in Siesta Key
Palm Bay Club on Siesta Key New bathroom
2 bedrooms, 3 beds
1–6 Sept
4.75 out of 5 average rating, 28 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, 11 reviews
Top guest favourite
Flat in Siesta Key
Siesta Key Paradise - Steps to Beach & Village
3 bedrooms, 4 beds
7–12 Sept
5.0 out of 5 average rating, 11 reviews
Top guest favourite
Home in Sarasota
The Palms Away
2 bedrooms, 2 beds
7–12 Sept
5.0 out of 5 average rating, 38 reviews
Apartment in Siesta Key
Newly Remodeled 2026-Just walk out on to the sand!
2 bedrooms, 3 beds
5–12 Sept
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Home in Siesta Key
Stroll to the Sea, Steps to the Village, Boat dock
3 bedrooms, 4 beds
1–6 Sept
5.0 out of 5 average rating, 23 reviews
Top guest favourite
Home in Sarasota
NEW Luxe Resort Home*XL Pool/Hot Tub*1 mi to Beach
3 bedrooms, 4 beds
1–6 Sept
4.97 out of 5 average rating, 32 reviews
Top guest favourite
Home in Siesta Key
Beach, Village, Dock & Private Pool! One-of-a-kind
2 bedrooms, 5 beds
9–14 Sept
5.0 out of 5 average rating, 169 reviews
Home in Sarasota
Periwinkle House
5 bedrooms, 6 beds
1–7 Sept
New place to stay