Siesta Key Holiday Rentals - Holiday Homes in Siesta Key

Q: What are some of the best holiday rentals that Siesta Key has to offer?

Siesta Key Island Rentals : This highly rated holiday home rental in Siesta Key comes with free WiFi so that you can feel at home during your trip. This holiday rental also comes with free parking to give you added peace of mind. Another good choice for your trip to Siesta Key is Siesta Heron Suites & Villas .

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In two weeks

In two months

In three months

In four months

Our top choices for Siesta Key holiday rentals

A pool area with a waterfall feature, lounge chairs, and palm trees.

1. Tropical Beach Resorts

South Village

kurt

RM693 total

includes taxes & fees

21 Oct - 22 Oct

A modern living room with a flat-screen TV on a wooden cabinet, a grey sofa with patterned cushions, and a large window with sheer curtains.

2. SeaSpray Resort

Siesta Key

RM1,034 total

includes taxes & fees

2 Nov - 3 Nov

An outdoor patio with a grill, white chairs, and a red umbrella.

3. Hibiscus Suites - Gateway to Siesta Key

Sarasota

Kat

RM611 total

includes taxes & fees

22 Oct - 23 Oct

A large orange armchair against a white wall with a 'Captiva' sign. There are two potted plants beside the chair.

4. Captiva Beach Resort

South Village

Karla

RM858 total

includes taxes & fees

18 Oct - 19 Oct

5. The Ringling Beach House

Siesta Key

Ricardo

A compact living space with a kitchen, a dining area, and a sofa with cushions.

6. Tiny House Siesta

Sarasota

Staci

RM800 total

includes taxes & fees

17 Oct - 18 Oct

A covered outdoor area with a wooden table and chairs, a white door, and a yellow wall.

7. Yellow Palm Cottage, Heart of Siesta Key

Siesta Key Village

RM1,498 total

includes taxes & fees

18 Oct - 19 Oct

A room with a dining table, chairs, a television, a sofa, and a lamp.

8. BlueDolphin Cottage Walk To Siesta Beach

Siesta Key Village

RM1,597 total

includes taxes & fees

19 Oct - 20 Oct

A living room with a sofa, armchair, coffee table, and a potted plant.

9. Siesta Vibe Pool Walk To Crescent Beach

South Village

RM1,592 total

includes taxes & fees

30 Oct - 31 Oct

A patio area with a grill, potted plants, and a building with a teal door.

10. Beach Tree Cottage,Walk To Beach& Siesta

Siesta Key Village

RM1,431 total

includes taxes & fees

18 Oct - 19 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.

11. Siesta Heron Suites & Villas

Siesta Key

Christopher Robert

RM1,308 total

includes taxes & fees

19 Oct - 20 Oct

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

12. Siesta Sands Beach Resort 4th Floor With Elevator

South Village

A beach with a wooden picnic table, palm trees, and a clear blue sky.

13. Beach Road - Capri

Siesta Key

RM2,479 total

includes taxes & fees

20 Oct - 21 Oct

14. Siesta Sands Beach Resort Gulf View

South Village

Jessica

15. House of The Sun Siesta Key Crescent Beach

South Village

Margaret Theresa

RM3,028 total

includes taxes & fees

22 Oct - 23 Oct

A beach with tall grasses and a sunset sky.

16. Siesta Heron 6 / Sunset

Siesta Key

RM3,112 total

includes taxes & fees

21 Oct - 22 Oct

A kitchen with wooden cabinets, stainless steel appliances, a granite countertop, and a ceiling fan.

17. 4 Mi to Siesta Key Beach: Condo w/ Pool Access

Sarasota

Lori

RM1,228 total

includes taxes & fees

21 Oct - 22 Oct

A living room with a view of the ocean, a ceiling fan, and a wooden coffee table.

18. A Beach Retreat

Casey Key

Robin

RM850 total

includes taxes & fees

4 Nov - 5 Nov

A modern living room with a sofa, coffee table, and artwork on the walls.

19. Pineapple Paradise 1 13 min to Beach Fire Pit

Central Sarasota

RM1,445 total

includes taxes & fees

18 Oct - 19 Oct

20. Bridgewalk Resort

Bridge Street

Raisare

RM1,448 total

includes taxes & fees

25 Oct - 26 Oct

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Top Siesta Key Hotel Reviews

Tropical Beach Resorts

10/10 Excellent

"This Resort is wonderful"

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."

Tropical Breeze Resort

8/10 Good

"Place was great. It was clean. Amenities was nice prime location, walking distance to the beach walking distance to all the shops and restaurants. Only problem is once the front office is closed. You can’t get anything, unfortunately I didn’t realize we didn’t have bath towels so 10 o’clock calling them no response nothing. So make sure you check everything before the front office closes."

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!"

Find out more about Siesta Key

Search for holiday rentals in Siesta Key on Expedia.co.uk! You can easily find your home rentals, villas, holiday apartments in Siesta Key using one of the methods below:

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Frequently asked questions

Can I find a holiday rental in Siesta Key?

Yes, there are holiday rentals in Siesta Key close to St. Boniface Episcopal Church Labyrinth, or you can select a more secluded option if you're looking for a relaxing stay. Visitors to Siesta Key like the popular beaches and live music. You can also check out the entertainment venues while you're visiting.

What are some of the best holiday rentals that Siesta Key has to offer?

Siesta Key Island Rentals: This highly rated holiday home rental in Siesta Key comes with free WiFi so that you can feel at home during your trip. This holiday rental also comes with free parking to give you added peace of mind. Another good choice for your trip to Siesta Key is Siesta Heron Suites & Villas.

How many holiday rentals are there in Siesta Key?

With 401 Expedia holiday rentals, you're guaranteed to find just the right place for your Siesta Key stay.

What can I see and do in Siesta Key?

Siesta Key Beach and Crescent Beach are a couple of lovely local spots to enjoy the outdoors, whereas family-friendly attractions include Jim Neville Marine Preserve. While here, Safe Harbor Siesta Key and Point of Rocks are other places worth a visit.

What are holiday rentals like in Siesta Key?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Siesta Key. Holiday rentals offer extras like laundry facilities and kitchens so you'll have all the conveniences of home. If you're concerned about a sanitised environment, holiday rentals can provide a sense of security away from shared hotel lifts and lobbies packed with people while still allowing you the excitement and enjoyment of travel. You'll also find more space in a holiday rental than in a standard hotel, which makes a holiday rental an attractive option for a family trip or a small group gathering.

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Treat yourself

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Check prices for these dates

Our top choices for Siesta Key holiday rentals

1. Tropical Beach Resorts

2. SeaSpray Resort

3. Hibiscus Suites - Gateway to Siesta Key

4. Captiva Beach Resort

5. The Ringling Beach House

6. Tiny House Siesta

7. Yellow Palm Cottage, Heart of Siesta Key

8. BlueDolphin Cottage Walk To Siesta Beach

9. Siesta Vibe Pool Walk To Crescent Beach

10. Beach Tree Cottage,Walk To Beach& Siesta

11. Siesta Heron Suites & Villas

12. Siesta Sands Beach Resort 4th Floor With Elevator

13. Beach Road - Capri

14. Siesta Sands Beach Resort Gulf View

15. House of The Sun Siesta Key Crescent Beach

16. Siesta Heron 6 / Sunset

17. 4 Mi to Siesta Key Beach: Condo w/ Pool Access

18. A Beach Retreat

19. Pineapple Paradise 1 13 min to Beach Fire Pit

20. Bridgewalk Resort

Find holiday rentals that suit your style

Top Siesta Key Hotel Reviews

Tropical Beach Resorts

Cottages at Siesta Key Inn

Siesta Key Beach Resort and Suites

The Capri at Siesta

SeaSpray Resort

Tropical Breeze Resort

The Ringling Beach House

The Inn On Siesta Key

Siesta Key Island Rentals

Find out more about Siesta Key

Frequently asked questions

Go further with the Expedia app

Siesta Key Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Siesta Key holiday rentals

1. Tropical Beach Resorts

2. SeaSpray Resort

3. Hibiscus Suites - Gateway to Siesta Key

4. Captiva Beach Resort

5. The Ringling Beach House

6. Tiny House Siesta

7. Yellow Palm Cottage, Heart of Siesta Key

8. BlueDolphin Cottage Walk To Siesta Beach

9. Siesta Vibe Pool Walk To Crescent Beach

10. Beach Tree Cottage,Walk To Beach& Siesta

11. Siesta Heron Suites & Villas

12. Siesta Sands Beach Resort 4th Floor With Elevator

13. Beach Road - Capri

14. Siesta Sands Beach Resort Gulf View

15. House of The Sun Siesta Key Crescent Beach

16. Siesta Heron 6 / Sunset

17. 4 Mi to Siesta Key Beach: Condo w/ Pool Access

18. A Beach Retreat

19. Pineapple Paradise 1 13 min to Beach Fire Pit

20. Bridgewalk Resort

Find holiday rentals that suit your style

Top Siesta Key Hotel Reviews

Tropical Beach Resorts

Find out more about Siesta Key

Frequently asked questions

Go further with the Expedia app