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Search results; Over 1,000 homes in Siesta Key

Top guest favourite
Apartment in Siesta Key
Breathtaking Beachfront Views in Siesta Key
2 bedrooms, 4 beds, 2 private bathrooms
1–6 Sept
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5.0 out of 5 average rating, 101 reviews
Superhost
Home in Sarasota
Luxury Coastal Siesta Ocean Sandbar #1
5 bedrooms, 8 beds, 6 bathrooms
1–8 Sept
Apartment in Siesta Key
Jamaica Royale 099 Nice Gulf side unit!
2 bedrooms, 5 beds, 2 bathrooms
1–6 Sept
Guest favourite
Apartment in Siesta Key
Siesta Key condo - short walk to beach - GBB 1219
2 bedrooms, 3 beds, 2 bathrooms
1–8 Sept
5.0 out of 5 average rating, 8 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
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, 10 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
Home in Siesta Key
3BR waterfront pool home, family friendly, WIFI
3 bedrooms, 5 beds, 2 bathrooms
1–8 Sept
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
Guest favourite
Home in Siesta Key
3 bedroom renovated pool home near beach/village
3 bedrooms, 4 beds, 2 bathrooms
8–13 Sept
5.0 out of 5 average rating, 5 reviews
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
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
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
Townhouse in Siesta Key
3 bdrm 4 bath Beachhouse
3 bedrooms, 4 beds, 3.5 bathrooms
7–12 Sept
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Flat in Siesta Key
Beach Walk Bungalow
3 bedrooms, 3 beds, 2 bathrooms
17–22 Sept
4.94 out of 5 average rating, 34 reviews
Top guest favourite
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
Apartment in Siesta Key
Charming Siesta Key Condo Just Minutes from Beach
2 bedrooms, 3 beds, 2 bathrooms
1–7 Sept
4.96 out of 5 average rating, 84 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