Siesta Key Vacation Homes

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 holiday 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

HK$3,100 total

includes taxes & fees

13 Oct - 14 Oct

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.

HK$2,259 total

includes taxes & fees

5 Oct - 6 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.

HK$3,068 total

includes taxes & fees

5 Oct - 6 Oct

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

HK$2,409 total

includes taxes & fees

5 Oct - 6 Oct

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

5. The Mermaid at Tiny House Siesta

Sarasota

Kadina A.

HK$1,381 total

includes taxes & fees

12 Oct - 13 Oct

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

Siesta Key Village

Kelsey E.

HK$3,337 total

includes taxes & fees

5 Oct - 6 Oct

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

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

Siesta Key Village

N A.

HK$4,592 total

includes taxes & fees

5 Oct - 6 Oct

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

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

Sarasota

Wayne

HK$1,522 total

includes taxes & fees

19 Oct - 20 Oct

A spacious living room with a stone fireplace, comfortable seating, and a view of the outdoors.

9. Siesta beach....one and only

Sarasota

Jennifer M.

HK$3,666 total

includes taxes & fees

5 Oct - 6 Oct

A beach with clear turquoise water, people swimming and walking along the shore, and a sailboat in the distance.

10. Star Fish. 3 Bed 2 Bath. POOL. Daily Rentals

South Village

Cortney

HK$4,534 total

includes taxes & fees

6 Oct - 7 Oct

11. Pet Friendly home, Close to Sarasota Beach!

Siesta Key Village

Matthew Y.

HK$4,832 total

includes taxes & fees

5 Oct - 6 Oct

A staircase leading to a door with a welcome mat, a television on a stand, and a wooden ceiling.

12. Tiny House Pirate Ship - Sleeps 2 near Siesta Key beach

Sarasota

HK$1,301 total

includes taxes & fees

5 Oct - 6 Oct

An aerial view of a beach with clear turquoise waters, a sandy shore, and a coastal town with buildings and greenery.

13. Sea Dream - Pet Friendly, Located in Siesta Key Village, Steps to Siesta Key Beach!

Siesta Key Village

George J.

HK$5,010 total

includes taxes & fees

18 Oct - 19 Oct

A modern kitchen with white cabinetry, stainless steel appliances, and a tiled backsplash.

14. Condo with Private Beach Access, Great Shared Amenities - Private Beach House

Siesta Key

"Our stay at Private Beach House was excellent! The location was perfect, the beach was beautiful, and the house was very comfortable and convenient. We absolutely enjoyed our time there and would definitely stay again. We did have an issue with the water for one night, but we called and they were very responsive and had it resolved in less than an hour. We really appreciated how quickly they took care of it. Overall, we had a wonderful stay and would definitely recommend Private Beach House!"

Kelmarie

HK$6,537 total

includes taxes & fees

5 Oct - 6 Oct

An aerial view of a coastal city with a long sandy beach, numerous hotels, and clear blue waters.

15. Lulu's Key House Leatherback 2/2 Downstairs

Siesta Key Village

HK$5,256 total

includes taxes & fees

10 Oct - 11 Oct

A poolside setting with candles and decorative stones.

16. Modern 2BR Retreat · Heated Pool · Near Siesta

Sarasota

Maria V.

A sandy beach with a clear sky and palm trees.

17. FRESHLY RENOVATED Adorable Bungalow Near the Beach! - Casita West

South Village

Amber M.

A beach with clear turquoise waters and a sandy shore.

18. Luxury Siesta Key Beachfront Oasis-STEPS TO WORLD FAMOUS SIESTA KEY SAND

Siesta Key

Meredith S.

HK$5,017 total

includes taxes & fees

5 Oct - 6 Oct

A modern kitchen with a stainless steel refrigerator, granite countertop, white cabinetry, and a dining area with a table and chairs.

19. Beautiful 2 Bedroom Duplex Steps Away from the Beach

South Village

"The property is beautiful! It was everything we wanted and needed. Very clean with all the amenities. The hostess responded promptly when ever we contacted them and the check-in and out was so simple! Loved that we could walk to grab a bite to eat or just check out some shopping. The best part was the 3 min walk to the private beach which was very clean and the perfect beach for shelling! We loved this place so much we are concerning rented both 1 and 2 units next season so we can bring our...

Tajsha G.

HK$4,510 total

includes taxes & fees

5 Oct - 6 Oct

20. 2 Bedroom Unit with Pool - 2 min walk to Siesta Beach

Siesta Key

Melissa B.

HK$4,766 total

includes taxes & fees

18 Oct - 19 Oct

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Top Siesta Key Hotel Reviews

Siesta Key Beach Resort and Suites

10/10 Excellent

"Everything was amazing! We definitely will be back"

Cottages at Siesta Key Inn

10/10 Excellent

"If you’re looking for a nice little quiet stay that’s really close to the beach, shops and restaurants this is it. My studio was very clean and freshly furnished. I received a text daily asking how our stay is going and if we needed anything. Couldn’t have been happier with our stay."

SeaSpray Resort

10/10 Excellent

"Excellent resort and so helpful staff. The design of the rooms is very chic and stylish. Everything seems good quality and newly decorated. The beach trolly with chairs and umbrellas is a great addition. Walking distance to beach, bars and restaurants and free parking. We will be back highly recommend. Thank you."

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