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Search results; Over 1,000 homes in Siesta Key

Top guest favourite
Serviced apartment in Siesta Key
Siesta Key #1 Beach, pickle ball & tennis paradise
2 bedrooms, 4 beds, 2 private bathrooms
7–12 Aug
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4.99 out of 5 average rating, 217 reviews
Guest favourite
Home in Siesta Key
Bahama Mama | Tropical Retreat on Siesta Key
5 bedrooms, 7 beds
20–25 Sept
5.0 out of 5 average rating, 5 reviews
Guest favourite
Home in Siesta Key
House on Siesta Key with Private Pool and Hot tub!
4 bedrooms, 4 beds
24–29 Aug
5.0 out of 5 average rating, 5 reviews
Superhost
Home in Sarasota
The Siesta Key Retreat - An Island Garden Oasis!
4 bedrooms, 4 beds
26–31 Jul
New place to stay
Top guest favourite
Home in Siesta Key
Steps to Siesta Key Beach! Sunset Balcony Views!
2 bedrooms, 3 beds
1–7 Aug
5.0 out of 5 average rating, 6 reviews
Superhost
Home in Sarasota
Spacious 2BR Retreat w/Large Spool Near Downtown
2 bedrooms, 3 beds
16–21 Jul
New place to stay
Guest favourite
Home in Siesta Key
Waterfront Home Pool & Dock 5 Min to Siesta Beach
3 bedrooms, 4 beds
3–8 Aug
5.0 out of 5 average rating, 5 reviews
Home in Siesta Key
3BR waterfront pool home, family friendly, WIFI
3 bedrooms, 5 beds
10–17 Jul
Home in Anna Maria
Heart of Pine Ave | 6 En-Suites | Heated Pool
6 bedrooms, 8 beds
15–20 Aug
New place to stay
Superhost
Apartment in Sarasota
Direct Gulf View - Residence 505
4 bedrooms
26–31 Aug
Home in Siesta Key
4B Arthouse & Hot Tub | Walk to Siesta Key Beach!
4 bedrooms, 5 beds
26–31 Jul
New place to stay
Guest favourite
Home in Sarasota
Dream's Corner Cove
3 bedrooms, 6 beds
31 Aug – 5 Sept
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Home in Sarasota
Luxury Lido Key Heated Pool & Game Room
3 bedrooms, 5 beds
13–20 Sept
5.0 out of 5 average rating, 25 reviews
Superhost
Home in Anna Maria
Sundowner Beach: Luxury Gulf-front, stunning views
5 bedrooms, 9 beds
26–31 Aug
Guest favourite
Home in Sarasota
Big backyard hangout, firepit, large primary suite
3 bedrooms, 3 beds
12–17 Jul
5.0 out of 5 average rating, 29 reviews
Superhost
Home in Siesta Key
Villa Fiesta - 312
2 bedrooms, 3 beds
12–17 Jul
New place to stay
Top guest favourite
Home in Sarasota
NEW Luxe Resort Home*XL Pool/Hot Tub*1 mi to Beach
3 bedrooms, 6 beds
14–19 Aug
4.97 out of 5 average rating, 29 reviews
Top guest favourite
Home in Sarasota
Modern Pool House Sealand 3/2 near Siesta
3 bedrooms, 4 beds
12–17 Jul
4.98 out of 5 average rating, 99 reviews
Superhost
Home in Sarasota
6630 - Mira Bella
4 bedrooms, 10 beds
5–10 Aug