Siesta Key, FL Vacation Homes from SAR 1,160

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 vacation homes

A wooden deck with blue lounge chairs, orange chairs, and a barbecue area.

1. Dolphin Villa | Pool | Steps to Siesta Key Village

Siesta Key Village

Amy

SAR 1,445 total

includes taxes & fees

31 Oct - 1 Nov

A modern kitchen with white cabinets, a stainless steel refrigerator, and a large island with bar stools.

2. [lounge like locals] walk to siesta beach +bikes

Siesta Key

Moreixa C.

SAR 1,161 total

includes taxes & fees

20 Oct - 21 Oct

A wooden deck with white railings, red chairs, and a view of a residential area with palm trees and a blue house.

3. Island Villa | Cozy Beach Retreat | Walk to Village

Siesta Key Village

Amber B.

SAR 1,695 total

includes taxes & fees

31 Oct - 1 Nov

A spacious living room with a leather sofa, a glass coffee table, and a wooden dining table. Large windows provide ample natural light and a view of the outdoors.

4. Siesta Heron Suites & Villas

Siesta Key

Christopher Robert

SAR 1,160 total

includes taxes & fees

20 Oct - 21 Oct

5. Everglades Villa • Sleeps 8 • Walk to Siesta Beach

Siesta Key Village

Kelsey E.

SAR 1,624 total

includes taxes & fees

19 Oct - 20 Oct

A beach with waves and a bird flying near the shore.

6. The Mermaid at Tiny House Siesta

Sarasota

Kadina A.

A beach with clear turquoise water, a sandy shore, and a few beach umbrellas.

7. Sea Turtle- Full Sized living at Tiny House Siesta

Sarasota

Wayne

An aerial view of a beach with clear skies, a sandy shore, and a mix of greenery and paths.

8. Siesta Key Beach Duplex-Close to Sarasota Beach/Pet Friendly

Siesta Key Village

Ivette R.

View all properties

Find vacation rentals that suit your style

Private vacation homes

Aparthotels

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

Top Siesta Key Hotel Reviews

The Capri at Siesta

8/10 Good

"The room was very clean and equipped with needed items. The laundry room was nice with beach chairs & coolers to borrow if you wanted. Very close proximity to the pool & private beach. The office staff was extremely kind & helpful."

Cottages at Siesta Key Inn

10/10 Excellent

"The Cottages were sold to Azul Resorts which has another similar location around the corner. The entire complex went through a renovation in December of 2025. Expedia still shows it under the old name, and that was a little confusing when I arrived. It looked very clean and new for the most part. I booked the Studio unit with a King size bed. The bed was comfortable and the pillows were great. There is a 65" TV on the wall. It was exactly the same as the one I have at home which was great because I didn't have to learn how to work it. :-) The location is about 250 ft. from the beach access entrance (#13), which is another 200 foot walking path to the sand. The path leaves you about 150 feet from the water (low tide), and about 100 feet from the water (high tide). So if walking is difficult for you, know that you will walk approximately 550 feet before you can wet your toes in the Gulf of America. Regarding the location, it is about 4 miles South of the Sarasota Village downtown, 3 miles South of the main Sarasota Beach public parking area, but there are plenty of restaurant and tiki bars within 1 or 2 miles of the Azul Resort. The only cons I found were that the pool wasn't heated, and someone operates a chair and umbrella rental service that blocks a huge part of the beach area. There is room to the left of the path, or you can go to the right of the blocked off area. They also leave a small strip in front of the blocked area. We didn't have a problem finding room on d'sand."

Siesta Key Beach Resort and Suites

8/10 Good

"I had a three night stay at this hotel on Siesta Key. Great location, and I walked every where safely alone. Very friendly staff! My comments on the room. - the mattress needs to be replaced in room 102 - a threshold at the door would be nice to keep any critters from crawling into the room. - the dehumidifier in the room makes some very loud sounds, frequently, which woke me often."

The Ringling Beach House

10/10 Excellent

"We had a wonderful stay at The Ringling Beach House! The location was perfect, within walking distance of the beach and so many great shops and restaurants. The place was beautiful, very clean, and comfortable. Our host was amazing, friendly, and always quick to communicate, making our stay even more enjoyable. We truly enjoyed our time here and would definitely recommend it to anyone looking for a relaxing beach getaway. We would love to stay again!"

Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Siesta Key vacation homes

1. Dolphin Villa | Pool | Steps to Siesta Key Village

2. [lounge like locals] walk to siesta beach +bikes