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Search results; Over 1,000 places

Guest favorite
Condo in Siesta Key
Seaside on Siesta Key Beach
3 min walk
May 16 – 23
4.99 out of 5 average rating, 67 reviews
Guest favorite
Condo in Siesta Key
2 BR condo in Siesta Key w/ Private beach access
5 min drive
Apr 27 – May 4
4.97 out of 5 average rating, 36 reviews
Guest favorite
Apartment in Siesta Key
Renovated beachside condo-direct beach access
2 min drive
May 26 – 31
4.95 out of 5 average rating, 37 reviews
Superhost
Cottage in Siesta Key
Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
3 min drive
Apr 27 – May 2
4.88 out of 5 average rating, 214 reviews
Guest favorite
Condo in Siesta Key
NO Stairs, beachfront & short walk to the village!
10 min walk
Apr 27 – May 2
4.92 out of 5 average rating, 87 reviews
Guest favorite
Apartment in Siesta Key
Siesta Key #1 Beach, pickle ball & tennis paradise
2 min drive
Aug 2 – 7
4.99 out of 5 average rating, 139 reviews
Guest favorite
Condo in Siesta Key
Comfy Siesta Key Condo
13 min walk
May 8 – 15
4.82 out of 5 average rating, 72 reviews
Guest favorite
Condo in Siesta Key
Amazing beach view! Entire unit renovated!
5 min walk
May 28 – Jun 4
5.0 out of 5 average rating, 17 reviews
Apartment in Siesta Key
Sunset Beach Studio With Pool!
4 min drive
Jun 15 – 20
4.81 out of 5 average rating, 148 reviews
Guest favorite
Condo in Siesta Key
❤️ Hidden Gem steps away from #1 beach 🏖 Siesta Key
5 min drive
Apr 28 – May 3
5.0 out of 5 average rating, 64 reviews
Guest favorite
Condo in Siesta Key
Sarasota Surf & Racquet Club Siesta Key Condo
2 min drive
May 18 – 23
4.91 out of 5 average rating, 78 reviews
Guest favorite
Apartment in Siesta Key
Lil' Kahuna Siesta Retreat
3 min drive
Apr 27 – May 2
5.0 out of 5 average rating, 9 reviews
Guest favorite
Apartment in Siesta Key
Siesta Sunset Condo
2 min drive
May 2 – 9
5.0 out of 5 average rating, 7 reviews
Guest favorite
Condo in Siesta Key
The Honeymoon Suite on Siesta Key Beach
4 min walk
Jun 9 – 14
4.95 out of 5 average rating, 62 reviews
Superhost
Condo in Siesta Key
LUXECottage @Crystal Sands -Siesta Key Beachfront!
6 min walk
May 18 – 25
4.91 out of 5 average rating, 55 reviews
Guest favorite
Condo in Siesta Key
Siesta Key Beach Front Condo
5 min walk
Aug 11 – 18
4.95 out of 5 average rating, 78 reviews
Guest favorite
Home in Siesta Key
[Ocean Oasis] king bed guesthouse +washer/dryer
2 min drive
Apr 26 – May 1
4.88 out of 5 average rating, 34 reviews
Guest favorite
Apartment in Siesta Key
Across from beach & walk to town
10 min walk
Apr 26 – May 1
5.0 out of 5 average rating, 15 reviews