A coastal cityscape with a sunset over the water, featuring several high-rise buildings and palm trees.

Longboat Key Holiday Rentals

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Longboat Key holiday rentals

A multi-story building with a light blue facade, featuring a restaurant named 'Bridge Street Bistro' and a sign for 'Island Time.'

1. Bridgewalk Resort

Bridgewalk Resort
3.5 star property
Bridge Street
9.4 out of 10, Exceptional, (835 reviews)
"I loved this hotel"
United States
Raisare
The price is S$453
includes taxes & fees
6 Oct - 7 Oct
Bridgewalk Resort
A modern building with a white exterior, a brick gable, and a palm tree in the foreground.

2. Pelican Post at Anna Maria Island Inn

Pelican Post at Anna Maria Island Inn
3.5 star property
Bradenton Beach
9.2 out of 10, Wonderful, (474 reviews)
"Great location and walking distance to the beach"
United States
Francesca
The price is S$278
includes taxes & fees
7 Oct - 8 Oct
Pelican Post at Anna Maria Island Inn
A modern bedroom with a large bed, a TV mounted on the wall, a wooden headboard, and a view of the sea through the balcony.

3. Seabreeze at Anna Maria Island Inn

Seabreeze at Anna Maria Island Inn
3.0 star property
Bradenton Beach
8.8 out of 10, Excellent, (139 reviews)
"Right on beach, in a good area. Comfy beds, would stay here again"
United States
Katelyn
The price is S$375
includes taxes & fees
4 Oct - 5 Oct
Seabreeze at Anna Maria Island Inn
A pool area with a waterfall feature, lounge chairs, and palm trees.

4. Tropical Beach Resorts

Tropical Beach Resorts
3.5 star property
South Village
9.4 out of 10, Exceptional, (5,937 reviews)
"Amazing resort,"
United States
kurt
The price is S$228
includes taxes & fees
4 Oct - 5 Oct
Tropical Beach Resorts
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.

5. SeaSpray Resort

SeaSpray Resort
4.0 star property
Siesta Key
9.6 out of 10, Exceptional, (187 reviews)
"Great place with a bunch of little touches that put it above and beyond"
United States
Rafe
The price is S$304
includes taxes & fees
3 Nov - 4 Nov
SeaSpray Resort
A water slide in a pool area with a rocky backdrop and a small waterfall.

6. Cedar Run Resort - Roam Hospitality

Cedar Run Resort - Roam Hospitality
3.5 star property
South Bradenton
9.2 out of 10, Wonderful, (10 reviews)
"I would stay again, very accommodating"
United States
Deliondra
Cedar Run Resort - Roam Hospitality
A modern outdoor seating area with two blue chairs and a large potted plant.

7. Pet-friendly Bradenton Home 1.5 Mi to Cortez Beach

Pet-friendly Bradenton Home 1.5 Mi to Cortez Beach
3.0 star property
Bradenton
10.0 out of 10, Exceptional, (3 reviews)
"Very nice place to stay. Clean and a lot of amenities. We enjoyed all the little touches that went into decorating the house, giving it a beach house feel. We would definitely stay here again. "
United States
Rob
The price is S$429
includes taxes & fees
6 Oct - 7 Oct
Pet-friendly Bradenton Home 1.5 Mi to Cortez Beach
A wooden boardwalk leading to a beach with a view of the ocean and clouds in the sky.

8. Haley's at The Anna Maria Island Inn

Haley's at The Anna Maria Island Inn
3.0 star property
Holmes Beach
8.6 out of 10, Excellent, (485 reviews)
"perfect"
United States
Danielle
The price is S$259
includes taxes & fees
7 Oct - 8 Oct
Haley's at The Anna Maria Island Inn
An outdoor patio with a grill, white chairs, and a red umbrella.

9. Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key
2.5 star property
Sarasota
8.8 out of 10, Excellent, (2,457 reviews)
"This place was perfect!"
United States
Kat
The price is S$197
includes taxes & fees
4 Oct - 5 Oct
Hibiscus Suites - Gateway to Siesta Key
A large orange armchair against a white wall with a 'Captiva' sign. There are two potted plants beside the chair.

10. Captiva Beach Resort

Captiva Beach Resort
3.0 star property
South Village
9.0 out of 10, Wonderful, (1,314 reviews)
"Clean room, beach access, easy parking, friendly staff"
United States
Karla
The price is S$247
includes taxes & fees
6 Oct - 7 Oct
Captiva Beach Resort
A covered outdoor bar area with seating, a pool, and a view of the outdoors.

11. Beach House Suites by the Don CeSar

Beach House Suites by the Don CeSar
3.0 star property
Belle Vista
9.0 out of 10, Wonderful, (1,202 reviews)
"Great place to stay"
United States
Michael
The price is S$407
includes taxes & fees
4 Oct - 5 Oct
Beach House Suites by the Don CeSar
A beach scene with waves gently lapping at the shore and the sun setting in the distance.

12. Palm Tree Villas

Palm Tree Villas
3.0 star property
Holmes Beach
9.2 out of 10, Wonderful, (174 reviews)
"It was just a beautiful stay and love to come back next year!!"
United States
Allison
The price is S$803
includes taxes & fees
4 Oct - 5 Oct
Palm Tree Villas
An outdoor deck with tables and chairs, a striped umbrella, and a view of the beach.

13. Alamanda Villas

Alamanda Villas
3.5 star property
Holmes Beach
8.4 out of 10, Very good, (11 reviews)
"The condo was great! Couldn’t have asked for a better place to start our first time in AMI!"
United States
Josephine
The price is S$571
includes taxes & fees
7 Oct - 8 Oct
Alamanda Villas
A compact living space with a kitchen, a dining area, and a sofa with cushions.

14. Tiny House Siesta

Tiny House Siesta
2.0 star property
Sarasota
8.4 out of 10, Very good, (387 reviews)
"It's a very cute tiny house in a great location. Walking distance to Siesta Keys beach and numerous restaurants. I loved the decor in the sea turtle house. I would definitely stay here again next time I'm in Florida."
United States
Staci
The price is S$262
includes taxes & fees
8 Oct - 9 Oct
Tiny House Siesta
A modern kitchen with white cabinets, a microwave, and an oven. There is a dining table with chairs and a decorative bowl.

15. Sarasota Family Home Private Heated Pool Relax

Sarasota Family Home Private Heated Pool Relax
2.0 star property
Whitfield Estates
2.0 out of 10, (1 review)
"Very disappointing stay Unfortunately, our experience at this property was very disappointing. The biggest issue was the air conditioning, which was not working properly during our entire stay. The first night was already very uncomfortable, but during the day it seemed to cool a little better, so we decided not to request a technician at that point. However, the second night was even worse, and the heat made it extremely difficult to sleep and enjoy our stay. We did report the problem to the...
United States
German
The price is S$684
includes taxes & fees
6 Oct - 7 Oct
Sarasota Family Home Private Heated Pool Relax
A pair of stacked front-loading washing machines in a commercial setting.

16. Beach View 100ft To Beach and SPA

Beach View 100ft To Beach and SPA
2.0 star property
Siesta Key Village
The price is S$449
includes taxes & fees
4 Oct - 5 Oct
Beach View 100ft To Beach and SPA
A living room with a view of the ocean, a ceiling fan, and a wooden coffee table.

17. A Beach Retreat

A Beach Retreat
2.5 star property
Casey Key
9.2 out of 10, Wonderful, (686 reviews)
"Great stay!!"
United States
Genghis
The price is S$273
includes taxes & fees
5 Oct - 6 Oct
A Beach Retreat
A covered outdoor area with a wooden table and chairs, a white door, and a yellow wall.

18. Yellow Palm Cottage, Heart of Siesta Key

Yellow Palm Cottage, Heart of Siesta Key
2.0 star property
Siesta Key Village
The price is S$470
includes taxes & fees
4 Oct - 5 Oct
Yellow Palm Cottage, Heart of Siesta Key
A wooden structure with a thatched roof overlooking a beach.

19. Casey Key Resort

Casey Key Resort
3.0 star property
Casey Key
8.4 out of 10, Very good, (284 reviews)
"Nice little property,very well kept.Host was very nice and helpful.Will be back again."
United States
Greg
The price is S$294
includes taxes & fees
18 Oct - 19 Oct
Casey Key Resort
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.

20. Siesta Heron Suites & Villas

Siesta Heron Suites & Villas
3.5 star property
Siesta Key
8.4 out of 10, Very good, (46 reviews)
"Clean rooms, convenient location, nice property and amenities. Simple check-in and check-out"
United States
Christopher Robert
The price is S$376
includes taxes & fees
4 Oct - 5 Oct
Siesta Heron Suites & Villas
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Longboat Key Hotel Reviews

The Resort at Longboat Key Club

The Resort at Longboat Key Club

10/10 Excellent
"Perfect location and great service right on the beach"
Bradley 1-night trip
Posted 3 days ago
The Resort at Longboat Key Club

Frequently asked questions

Can I find a holiday rental in Longboat Key?

Yes, there are holiday rentals close to the most popular sights in Longboat Key, or you can select a more secluded option if you're looking for a relaxing stay. Nature enthusiasts will enjoy the popular beaches in Longboat Key. Make sure you have time to check out the monuments while you're in the area.

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

Tropical Villas of Venice Beach: This holiday home rental outside of Longboat Key is located near the beach, and has an outdoor pool, a terrace and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a microwave and kitchenware. Make the most of garden in this rental home to help you unwind.

How many holiday rentals are there in Longboat Key?

Choose from 17 Expedia holiday rentals in Longboat Key for a memorable holiday.

What can I see and do in Longboat Key?

Longboat Key Beaches and Jewfish Key are a couple of lovely local spots to get outside and enjoy nature. Lido Beach and Siesta Key Beach are other popular places to visit in the area.

What are holiday rentals like in Longboat Key?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Longboat Key. Holiday rentals offer extras like WiFi and washers and dryers so you'll have all the comforts of home. If you're concerned about a clean environment, holiday rentals can provide a sense of privacy away from public hotel lifts and bustling concierge desks while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a popular choice for a family trip.