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Search results; Over 1,000 homes in Siesta Key

Top guest favourite
Cottage in Siesta Key
Surf Shack- Walk to Village/Boat Dock Included
Studio, 2 beds, 1 private bathroom
25 Jul – 1 Aug
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4.96 out of 5 average rating, 96 reviews
Top guest favourite
Home in Siesta Key
Bahama Mama | Tropical Retreat on Siesta Key
5 bedrooms, 7 beds
27 Sept – 2 Oct
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
3–8 Aug
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Home in Sarasota
Luxury 3B/3B waterfront home w/ pool + boat access
3 bedrooms, 5 beds
11–16 Aug
5.0 out of 5 average rating, 8 reviews
Home in Sarasota
Charming beach bungalow minutes from Siesta Key
2 bedrooms, 3 beds
19–24 Jul
New place to stay
Flat in Siesta Key
Villa with private beach, 3 pools complex on beach
2 bedrooms, 3 beds
16–21 Aug
New place to stay
Guest favourite
Home in Siesta Key
House on Siesta Key with Private Pool and Hot tub!
4 bedrooms, 4 beds
24–29 Aug
4.88 out of 5 average rating, 8 reviews
Top guest favourite
Home in Sarasota
4BRHeated Pool•Fire Pit•Pool Table Mins Siesta Key
4 bedrooms, 7 beds
23–28 Aug
5.0 out of 5 average rating, 22 reviews
Home in Sarasota
Tropical Oasis 4 BR Home w/ Pool & Spa
4 bedrooms, 5 beds
3–8 Aug
New place to stay
Top guest favourite
Home in Siesta Key
Completely Remodeled "Beach House on Siesta"
4 bedrooms, 6 beds
25 Jul – 1 Aug
5.0 out of 5 average rating, 27 reviews
Top guest favourite
Home in Sarasota
Sarasota Paradise/Stunning Home/Heated Pool
4 bedrooms, 6 beds
23–28 Jul
5.0 out of 5 average rating, 45 reviews
Superhost
Apartment in Sarasota
Direct Gulf View - Residence 505
4 bedrooms
1–6 Sept
Home in Sarasota
4 Mi to Siesta Key Beach! Spacious Family Getaway
3 bedrooms, 5 beds
15–20 Aug
New place to stay
Superhost
Home in Sarasota
Sun Coast Oasis-Heated Pool-Pool Table-Arcade
3 bedrooms, 5 beds
16–21 Aug
New place to stay
Top guest favourite
Home in Bradenton
Sleeps 24 · Heated Pool · Pickleball · Arcade
7 bedrooms, 12 beds
2–7 Aug
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Home in Sarasota
Modern 4BR Home *Heated Pool & Spa*
4 bedrooms, 4 beds
26 Aug – 2 Sept
4.95 out of 5 average rating, 196 reviews
Home in Siesta Key
Luxury Canal Home/Pool & Pool House/Siesta Key
3 bedrooms, 5 beds
31 Jul – 5 Aug
5.0 out of 5 average rating, 4 reviews
Guest favourite
Home in Sarasota
Relaxing Lakefront 3bd Heated Pool Near Siesta Key
3 bedrooms, 4 beds
2–7 Aug
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Home in Sarasota
The Palms Away
2 bedrooms, 2 beds
24–29 Aug
5.0 out of 5 average rating, 36 reviews