Siesta Key Chalets

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

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Siesta Key chalets

1. Beach Rd, 300ft to Beach Access & 500ft to Siesta Key Village, 2bdr

Siesta Key Village

Angie

HK$8,194 total

includes taxes & fees

6 Oct - 7 Oct

2. Beach Rd, 300ft to Beach Access & 500ft to Siesta Key Village, 2bdr & Studio

Siesta Key Village

HK$12,271 total

includes taxes & fees

8 Sept - 9 Sept

3. Beach Rd, 300ft to Beach Access & 500ft to Siesta Key Village, 2bdr & Studio

Siesta Key Village

Bobbi M.

HK$14,735 total

includes taxes & fees

6 Oct - 7 Oct

View all properties

Find holiday rentals that suit your style

Private holiday homes

Condos

Save an average of 15% on thousands of hotels when you're signed in

Top Siesta Key Hotel Reviews

The Capri at Siesta

10/10 Excellent

"Clean room, Nice kitchen and BBQ grill.The staff were very nice."

Tranquil villa with private beach, 2br/2ba 3 pools, complex on beach!! Patio

8/10 Good

"My boyfriend and I had a lovely stay here. It was only 2 days but the place was super cleaned and as described. Parking was a slight hassle as they were doing paving when we arrived and we couldn’t park under cover and had to park across the complex. But that was no fault of the owner. We loved the location of this unit as it is easy access to a beautiful private beach that was peaceful and calm. We wished we could’ve stayed longer, but it was a welcome respite for us. Ruth was a wonderful host and very communicative and helpful. Definitely can recommend this place if you’re visiting siesta key and want a relaxing spot with wonderful beach access!"

Twin Palms at Siesta

8/10 Good

"The room was spotless, the staff was very helpful. We appreciated being supplied with a wagon and beach chairs to make walking to the beach and easy trip. My only recommendation is for those who may have a hard time sleeping is to bring ear plugs to block out noise from the air conditioner cycling on and off and to bring a sleep mask to block out light coming in from the windows."

Beautiful, Cozy 3/2 Siesta Key home close to village,beaches, city and airport

10/10 Excellent

"The pictures don’t do this place full justice as it was even better in person! Very clean, close to everything, and the owner was very nice too! Such a cozy place with all the basic commodities. We brought groceries and extra toiletries with us and were able to cook and relax for an entire week! They even have some beach gear available as well. The only minor inconvenience was that we couldn’t get any of the ceiling fans to work, however, the AC was more than adequate to keep us comfy."

Steps to Siesta Key BEACH! Pool, Tennis Court, Shuffle Board, Pickle Ball!

10/10 Excellent

"Absolutley flawless! The folks at this resort were thorough, and had great communication! The property was clean, as well as the amenities. Literally rock throwing distance from the beach, where the sunsets are second to none! I would definitely book here again, the hosts made this vacation so much more enjoyable!"

Find out more about Siesta Key