Siesta Key Cottages

A yellow lifeguard tower with an American flag on a beach with people and umbrellas.

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Our top choices for Siesta Key cottages

A pool area with a blue deck, lounge chairs, a barbecue, and a view of buildings in the background.

1. The Inn On Siesta Key

Siesta Key

Stephen

A residential house with a white fence, a palm tree, and a parked car.

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

South Village

Clarissa S.

includes taxes & fees

30 Sept - 1 Oct

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

Siesta Key

Russ H.

A yellow house with a white door and number 5306.

4. Yellow Palm Cottage steps from the beach

Siesta Key Village

Tami B.

includes taxes & fees

20 Sept - 21 Sept

A small, single-story building with a blue roof and yellow walls, surrounded by a white picket fence and palm trees.

5. Blue Dolphin Cottage steps from the beach

Siesta Key Village

includes taxes & fees

24 Sept - 25 Sept

A hammock tied between two palm trees, a pink building with a red roof, and a bush with red flowers.

6. Pink Mango Cottage steps from the beach

Siesta Key Village

includes taxes & fees

20 Sept - 21 Sept

A kitchen with white cabinets, a coffee bar, a wooden shelf with decorative items, and a view of the outside.

7. Lookout Cottage Across street from Beach and Heated Pool

Siesta Key

"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!"

Keeley L.

A wooden deck with a glass door leading to a lake view, surrounded by greenery.

8. Siesta Heron 6 / Sunset

Siesta Key

includes taxes & fees

30 Sept - 1 Oct

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Top Siesta Key Hotel Reviews

Tropical Breeze Resort

8/10 Good

"The room was clean and staff were pleasant but there was no microwave in the room and I was told I had to request it, which I did and it never showed up. We went to check in at the 4pm check-in time and was told they just started cleaning our room. That is unacceptable you should have the rooms cleaned by 4 PM for check-in, especially in the off season. They did move us to a room that was already cleaned, which should have been done before I asked. The 10am check out time is a bit extreme,"

Siesta Key Beachside Villas

10/10 Excellent

"The villa was newly renovated and was designed nicely as were the grounds surrounding. Check-in was fast and easy and the staff was very helpful and knowledgeable of the surrounding town. Some minor convenience issues that affected our stay were; no hooks on the back of the bedroom or bathroom doors, no towel bar in shower, no safety grab bars in shower, and a walkway light at the corner would be helpful at villa #14. Overall it was a very nice place to stay and only a 3 min walk to beach and they have beach chairs in your villa."

The Inn On Siesta Key

10/10 Excellent

"I really love this place. I love how they thought about having all the things you would need at the beach and they have it free for people staying in to borrow. It was very convenient especially for us who flew in. The host was really nice too, she gave us a tour of the place and gave us a map and told us the good places to check. It’s also right across beach access 9 so it’s not a long walk going to the beach and you don’t need to look for a place to park when it’s busy."

Find out more about Siesta Key