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Search results; Over 1,000 homes in Siesta Key

Guest favourite
Apartment in Siesta Key
2 BR condo in Siesta Key w/ Private beach access
2 bedrooms, 3 beds, 2 private bathrooms
9–16 Sept
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4.97 out of 5 average rating, 75 reviews
Top guest favourite
Apartment in Siesta Key
Private Beach•3 Heated Pools•2BR•Ground Floor
2 bedrooms, 3 beds
28 Nov – 3 Dec
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Home in Siesta Key
Steps to Siesta Key Beach! Sunset Balcony Views!
2 bedrooms, 3 beds
26 Sept – 1 Oct
5.0 out of 5 average rating, 13 reviews
Top guest favourite
Villa in Siesta Key
Renovated Siesta Key Villa+Private Beach+3 Pools
1 bedroom, 3 beds
20–25 Sept
5.0 out of 5 average rating, 14 reviews
Guest favourite
Apartment in Siesta Key
The Flamingo's Nest at Sea Club II
2 bedrooms, 3 beds
26 Sept – 1 Oct
4.94 out of 5 average rating, 156 reviews
Top guest favourite
Flat in Siesta Key
Siesta Key Paradise - Steps to Beach & Village
3 bedrooms, 4 beds
11–16 Sept
5.0 out of 5 average rating, 12 reviews
Top guest favourite
Home in Sarasota
Siesta Breeze ~ Charming Coastal Cottage
2 bedrooms, 2 queen beds
9–14 Sept
4.99 out of 5 average rating, 142 reviews
Top guest favourite
Flat in Siesta Key
Beach Walk Bungalow
3 bedrooms, 3 beds
3–8 Oct
4.94 out of 5 average rating, 35 reviews
Guest favourite
Chalet in Siesta Key
Beach Rd, 300ft to Beach Access & 500ft to Village
2 bedrooms, 4 beds
12–17 Sept
4.93 out of 5 average rating, 60 reviews
Top guest favourite
Flat in Siesta Key
Siesta Premier Location - The 'Calm of Siesta'
2 bedrooms, 2 beds
18–25 Sept
4.94 out of 5 average rating, 142 reviews
Top guest favourite
Townhouse in Siesta Key
Gulf and Beach Views-Steps from Beach and Village
2 bedrooms, 2 beds
26 Oct – 2 Nov
5.0 out of 5 average rating, 48 reviews
Superhost
Home in Sarasota
Luxury Coastal Siesta Ocean Sandbar #1
5 bedrooms, 8 beds
16–23 Sept
Top guest favourite
Home in Sarasota
4BRHeated Pool•Fire Pit•Pool Table Mins Siesta Key
4 bedrooms, 7 beds
11–16 Oct
5.0 out of 5 average rating, 25 reviews
Luxe
Home in Siesta Key
7Bedroom Luxury Home W/Private Pool on Siesta Key!
7 bedrooms, 10 beds
9–14 Sept
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Flat in Siesta Key
Two bedroom across from beach, walk to town!
2 bedrooms, 4 beds
12–17 Sept
4.96 out of 5 average rating, 24 reviews
Top guest favourite
Apartment in Siesta Key
❤️ Hidden Gem steps away from #1 beach 🏖 Siesta Key
1 bedroom, 1 king bed
20–25 Sept
5.0 out of 5 average rating, 172 reviews
Top guest favourite
Home in Siesta Key
Siesta Key Retreat 1mi to Beach!
3 bedrooms, 4 beds
9–16 Sept
4.96 out of 5 average rating, 48 reviews
Guest favourite
Home in Sarasota
Siesta Key Fully-Renovated Unit 5 min to the beach
2 beds
9–14 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
5–10 Oct
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