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Search results; Over 1,000 homes in Siesta Key

Superhost
Cottage in Siesta Key
4 Bdrm (2 unit Cottage) walk to Siesta Beach
4 bedrooms, 5 beds, 3 private baths
Oct 22 – 29
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5.0 out of 5 average rating, 3 reviews
Top guest favorite
Home in Siesta Key
Bahama Mama | Tropical Retreat on Siesta Key
5 bedrooms, 7 beds, 5 baths
Sep 24 – 29
5.0 out of 5 average rating, 10 reviews
Superhost
Chalet in Siesta Key
Beach Rd, 300ft to Beach Access & 500ft to Village
2 bedrooms, 3 beds, 2 baths
Aug 18 – 23
New place to stay
Apartment in Siesta Key
Villa with private beach, 3 pools complex on beach
2 bedrooms, 3 beds, 1 bath
Aug 16 – 21
New place to stay
Luxe
Home in Bradenton Beach
Dream State ~ Gulf Front/Across from Beach!
6 bedrooms, 7 beds, 5.5 baths
Aug 30 – Sep 4
5.0 out of 5 average rating, 22 reviews
Home in Sarasota
Private Beach•3 Heated Pools•2BR•Ground Floor
2 bedrooms, 3 beds, 2 baths
Aug 29 – Sep 3
New place to stay
Top guest favorite
Villa in Siesta Key
Renovated Siesta Key Villa+Private Beach+3 Pools
1 bedroom, 3 beds, 1 bath
Aug 28 – Sep 2
5.0 out of 5 average rating, 9 reviews
Top guest favorite
Home in Siesta Key
Siesta Key Retreat 1mi to Beach!
3 bedrooms, 4 beds, 2 baths
Aug 23 – 30
4.96 out of 5 average rating, 45 reviews
Home in Sarasota
Heated Pool Retreat | Siesta Key & Downtown
3 bedrooms, 5 beds, 2 baths
Sep 8 – 13
New place to stay
Top guest favorite
Home in Sarasota
Siesta Serenity ~ Pool/Waterslide/Waterfront
4 bedrooms, 5 beds, 4 baths
Aug 30 – Sep 4
5.0 out of 5 average rating, 21 reviews
Home in Anna Maria
Luxury Home | 14 PPL | Pool & Hot Tub| Canal Views
4 bedrooms, 8 beds, 6 baths
Aug 15 – 20
New place to stay
Top guest favorite
Chalet in Siesta Key
Beach Rd, 300ft to Beach Access & 500ft to Village
2 bedrooms, 4 beds, 2 baths
Aug 19 – 24
4.93 out of 5 average rating, 60 reviews
Top guest favorite
Townhouse in Siesta Key
Gulf and Beach Views-Steps from Beach and Village
2 bedrooms, 2 beds, 2.5 baths
Aug 12 – 19
5.0 out of 5 average rating, 48 reviews
Top guest favorite
Home in Sarasota
Siesta Key Oasis Walk to Beach, Pool, Hot Tub, BBQ
3 bedrooms, 4 beds, 2 baths
Aug 23 – 28
4.95 out of 5 average rating, 37 reviews
Home in Siesta Key
Amazing Location - Waterfront House in Siesta Key
3 bedrooms, 4 beds, 3 baths
Aug 15 – 22
4.67 out of 5 average rating, 12 reviews
Top guest favorite
Home in Sarasota
St Armands Mid Century Rad Pad with Pool
3 bedrooms, 3 beds, 2 baths
Aug 12 – 17
5.0 out of 5 average rating, 73 reviews
Home in Siesta Key
3 bedroom renovated pool home near beach/village
3 bedrooms, 4 beds, 2 baths
Aug 24 – 29
5.0 out of 5 average rating, 5 reviews
Guest favorite
Condo in Siesta Key
The Flamingo's Nest at Sea Club II
2 bedrooms, 3 beds, 1 bath
Aug 16 – 21
4.94 out of 5 average rating, 154 reviews
Top guest favorite
Home in Bradenton
10 min AMI | 15 min IMG | Heated Pool
2 bedrooms, 3 beds, 2 baths
Dec 1 – 6
4.96 out of 5 average rating, 57 reviews