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Featured Cottages in Siesta Key

The Inn On Siesta Key

3.5 star property
10.0 out of 10, Exceptional, (181)
"The Inn on Siesta Key was awesome. Paige and Gabe were friendly and always helpful and they provided everything you would need for the beach. The property was clean and well maintained. The beach is literally across the street with a 3 minute walk. We will definitely be coming back. "
The price is AU$532
includes taxes & fees
3 Aug - 4 Aug
The Inn On Siesta Key

Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village

9.0 out of 10, Wonderful, (174)
"Loved this place, very roomy and even had a coffee bar, cute style, and right by the beach."
The price is AU$809
includes taxes & fees
20 Aug - 21 Aug
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village

Across The Street From #1 Beach

10.0 out of 10, Exceptional, (321)
"Very cute beach cottage! Great location,very clean ,no complaints,if ever in Siesta Key again would definitely stay here "
Across The Street From #1 Beach

ONLY 2 WKS LEFT IN AUG 5 Min walk to Beach & Village, Private Pool,On the Canal

9.8 out of 10, Exceptional, (23)
"Perfect place to stay. 1 mile to the village and beach access. We loved making our own meals in the grill and swimming in the pool. "
ONLY 2 WKS LEFT IN AUG 5 Min walk to Beach & Village, Private Pool,On the Canal

Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed

9.2 out of 10, Wonderful, (5)
"We really enjoyed the cleanliness and location. Pool was great. Having our own deck was nice. Great views. Highly recommend. "
The price is AU$519
includes taxes & fees
3 Aug - 4 Aug
Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed

Palm Shade Cottage | Charming 1-Bedroom in SK, Access to Pool, Walk to Beach!

10.0 out of 10, Exceptional, (2)
"The property was very nice and clean. It's also in a great location - very close to the beach and the Village. I will definitely stay here again."
Palm Shade Cottage | Charming 1-Bedroom in SK, Access to Pool, Walk to Beach!

Remodeled Siesta Key Escape – Walk to the Beach!

10.0 out of 10, Exceptional, (10)
"The property was great and easy communication would recommend very peaceful didn’t want to leave to be honest"
Remodeled Siesta Key Escape – Walk to the Beach!

Remodeled Siesta Key Escape Walk to the Beach!

3.0 star property
Remodeled Siesta Key Escape Walk to the Beach!

Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.

9.6 out of 10, Exceptional, (76)
"We loved everything about this rental! There are so many fun restaurants and bars within walking distance! There's also the convenience of the trolley stop right across the street for trips into the Village. The pool was nice and the beach was very close. We'd definitely recommend this location and we hope to be back next year!"
The price is AU$470
includes taxes & fees
27 Aug - 28 Aug
Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.

Cozy Cottage with Hot Tub

10.0 out of 10, Exceptional, (2)
"We loved the home and location and would definitely stay here again!"
Cozy Cottage with Hot Tub

Cabana Cottage Across street from Beach and Heated Pool

10.0 out of 10, Exceptional, (5)
"This was our first time in Siesta Key. We found the location of the Inn to be perfect. Within walking distance to the Village with all the shops and restaurants plus right across the street from the beach access. Plus the free trolley stop is right across the street. The staff was super friendly and very accommodating. They really go above and beyond to make you feel welcome. The cottage was very clean and had everything we needed for our stay and more! The decor and feel of the cottage was the...
Cabana Cottage Across street from Beach and Heated Pool

Siesta Key Village Home < Half Mi to Beach!

3.0 star property
Siesta Key Village Home < Half Mi to Beach!

Haven cottage Across street from beach and Heated Pool

9.8 out of 10, Exceptional, (7)
"Enjoyed the property, a very nice little unit, very clean and enjoyable"
Haven cottage Across street from beach and Heated Pool

Nest Cottage Across street from beach and Heated Pool

10.0 out of 10, Exceptional, (2)
"Clean, modern and staff is amazing. Room ready before noon received text notification from owners. This is now our new go to after 19 years of staying up the street. All of everything is provided in rooms and for beach life, well maintained and fun atmosphere no pressures except to make memories here."
Nest Cottage Across street from beach and Heated Pool

Nook Cottage Across street from beach and Heated Pool

10.0 out of 10, Exceptional, (4)
"They have really thought of everything and gone above and beyond to make our stay as comfortable as possible. Everything was very clean! Paige was a wonderful guide and host for the local area!"
Nook Cottage Across street from beach and Heated Pool

Sarasota Vacation Rental w/ Pool & Game Room!

3.0 star property
10.0 out of 10, Exceptional, (1)
"The property was perfect for our family. We had enough space for everyone. We enjoyed the pool, game room and the patio to grill. the neighbors were friendly! I would put a rug in front of the pool patio door inside to catch any dirt walking in, and that area can be very slippery with wet feet walking on the tile. Great stay! "
Sarasota Vacation Rental w/ Pool & Game Room!

Scenic Siesta Key Home ~ 1 Mi to Village & Beach!

2.5 star property
Scenic Siesta Key Home ~ 1 Mi to Village & Beach!

Charming 2BD Bungalow Close to Crescent Beach!

Charming 2BD Bungalow Close to Crescent Beach!

Lookout Cottage Across street from Beach and Heated Pool

10.0 out of 10, Exceptional, (1)
"The place was beautiful, tastefully furnished and decorated, and so clean! Plenty of towels and nice sheets. Loved the amenities like the pool and the beach chairs. The best part is the location - right across the street from a fantastic beach, close enough to walk to the main business district but not so close that you have to deal with all the people of you don’t want to. Perfect place for a couple looking for some R&R!"
Lookout Cottage Across street from Beach and Heated Pool

Siesta Key Oasis w/ Outdoor Pool + Screened Lanai!

3.0 star property
Siesta Key Oasis w/ Outdoor Pool + Screened Lanai!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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