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Search results; Over 1,000 homes in Siesta Key

Top guest favourite
Apartment in Siesta Key
1 Bed Cottage, Full Remodel, Beach Access #7, Walk
1 bedroom, 2 beds, 1 private bathroom
12–17 Sept
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4.94 out of 5 average rating, 81 reviews
Top guest favourite
Villa in Siesta Key
Renovated Siesta Key Villa+Private Beach+3 Pools
1 bedroom, 3 beds, 1 bathroom
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, 2 bathrooms
1–6 Sept
Villa in Siesta Key
Private Siesta Key Home minutes from the sand
2 bedrooms, 2 king beds, 2 bathrooms
11–18 Sept
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Bungalow in Sarasota
FlipFlopsOn III • ½ Mile Siesta Key • Walk to Bay
2 bedrooms, 4 beds, 1 bathroom
24–31 Oct
5.0 out of 5 average rating, 11 reviews
Apartment in Siesta Key
Jamaica Royale 099 Nice Gulf side unit!
2 bedrooms, 5 beds, 2 bathrooms
1–6 Sept
Flat in Siesta Key
Villa with private beach, 3 pools complex on beach
2 bedrooms, 3 beds, 1 bathroom
13–19 Sept
New place to stay
Home in Siesta Key
3BR waterfront pool home, family friendly, WIFI
3 bedrooms, 5 beds, 2 bathrooms
1–8 Sept
Top guest favourite
Home in Sarasota
The Palms Away
2 bedrooms, 2 beds, 1.5 bathrooms
7–12 Sept
5.0 out of 5 average rating, 38 reviews
Top guest favourite
Flat in Siesta Key
Siesta Key Paradise - Steps to Beach & Village
3 bedrooms, 4 beds, 2.5 bathrooms
7–12 Sept
5.0 out of 5 average rating, 11 reviews
Top guest favourite
Home in Siesta Key
Steps to Siesta Key Beach! Sunset Balcony Views!
2 bedrooms, 3 beds, 1 bathroom
26 Sept – 1 Oct
5.0 out of 5 average rating, 11 reviews
Top guest favourite
Home in Sarasota
NEW Luxe Resort Home*XL Pool/Hot Tub*1 mi to Beach
3 bedrooms, 4 beds, 2 bathrooms
1–6 Sept
4.97 out of 5 average rating, 32 reviews
Top guest favourite
Home in Sarasota
Modern 4bd | Heated Pool | Hot Tub + Studio Suite!
4 bedrooms, 6 beds, 3 bathrooms
8–13 Sept
5.0 out of 5 average rating, 22 reviews
Apartment in Siesta Key
Jamaica Royale 066 Beautifully Updated and close
2 bedrooms, 4 beds, 2 bathrooms
1–6 Sept
Apartment in Siesta Key
Newly Remodeled 2026-Just walk out on to the sand!
2 bedrooms, 3 beds, 2 bathrooms
5–12 Sept
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Home in Siesta Key
New Villa on Siesta Key! Pool & Walkable to Beach
2 bedrooms, 3 beds, 2 bathrooms
1–8 Sept
5.0 out of 5 average rating, 38 reviews
Top guest favourite
Home in Sarasota
Modern 4BR Home *Heated Pool & Spa*
4 bedrooms, 4 beds, 2 bathrooms
7–12 Sept
4.95 out of 5 average rating, 197 reviews
Top guest favourite
Home in Siesta Key
Stroll to the Sea, Steps to the Village, Boat dock
3 bedrooms, 4 beds, 2 bathrooms
1–6 Sept
5.0 out of 5 average rating, 23 reviews
Guest favourite
Apartment in Siesta Key
Beach Rd, 300ft to Beach Access & 500ft to Village
1 bedroom, 2 beds, 1 bathroom
25–30 Sept
4.94 out of 5 average rating, 68 reviews