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Search results; Over 1,000 homes in Siesta Key

Guest favourite
Apartment in Siesta Key
Siesta Key Condo. Checkout our great rates!
2 bedrooms, 4 beds, 1.5 private bathrooms
5–12 Sept
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4.96 out of 5 average rating, 136 reviews
Top guest favourite
Home in Siesta Key
Bahama Mama | Tropical Retreat on Siesta Key
5 bedrooms, 7 beds, 5 bathrooms
20–25 Sept
5.0 out of 5 average rating, 6 reviews
Guest favourite
Home in Siesta Key
Waterfront Home Pool & Dock 5 Min to Siesta Beach
3 bedrooms, 4 beds, 2 bathrooms
3–8 Aug
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, 4 bathrooms
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, 2 bathrooms
26–31 Jul
New place to stay
Home in Sarasota
Tropical Oasis 4 BR Home w/ Pool & Spa
4 bedrooms, 5 beds, 3 bathrooms
3–8 Aug
New place to stay
Top guest favourite
Home in Siesta Key
Steps to Siesta Key Beach! Sunset Balcony Views!
2 bedrooms, 3 beds, 1 bathroom
1–7 Aug
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Home in Sarasota
Luxury Lido Key Heated Pool & Game Room
3 bedrooms, 5 beds, 2 bathrooms
13–20 Sept
5.0 out of 5 average rating, 27 reviews
Home in Sarasota
Pink House | 12 PPL | Pool | Game Room | BBQ|Patio
4 bedrooms, 6 beds, 2 bathrooms
26–31 Jul
New place to stay
Superhost
Home in Sarasota
6630 - Mira Bella
4 bedrooms, 10 beds, 4 bathrooms
9–14 Aug
Home in Bradenton
Private Resort-Style Retreat Near IMG and AMI!
6 bedrooms, 9 beds, 4 bathrooms
10–15 Aug
New place to stay
Top guest favourite
Home in Sarasota
Books Tide Retreat - minutes from Siesta Beach
2 bedrooms, 2 beds, 2 bathrooms
9–14 Aug
4.96 out of 5 average rating, 54 reviews
Superhost
Apartment in Sarasota
Direct Gulf View - Residence 505
4 bedrooms, 4.5 bathrooms
1–6 Sept
Home in Sarasota
4 Mi to Siesta Key Beach! Spacious Family Getaway
3 bedrooms, 5 beds, 2 bathrooms
23–28 Aug
New place to stay
Home in Bradenton
Modern Farmhouse on the Water |Pool-Kayak-Pontoon
4 bedrooms, 5 beds, 3 bathrooms
25–30 Jul
New place to stay
Superhost
Home in Bradenton
Sleeps 24 · Heated Pool · Pickleball · Arcade
7 bedrooms, 12 beds, 5 bathrooms
2–7 Aug
5.0 out of 5 average rating, 4 reviews
Guest favourite
Home in Sarasota
Dream's Corner Cove
3 bedrooms, 6 beds, 2 bathrooms
31 Aug – 5 Sept
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Home in Sarasota
Luxury 3B/3B waterfront home w/ pool + boat access
3 bedrooms, 5 beds, 3 bathrooms
11–16 Aug
5.0 out of 5 average rating, 8 reviews
Home in Siesta Key
4B Arthouse & Hot Tub | Walk to Siesta Key Beach!
4 bedrooms, 5 beds, 3 bathrooms
26–31 Jul
New place to stay