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

Longboat Key Vacation Rentals

  • 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
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Longboat Key vacation 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, (842 reviews)
"I loved this hotel"
United States
Raisare
The price is AED 1,062
AED 1,303 total
includes taxes & fees
26 Oct - 27 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, (481 reviews)
"Great location and walking distance to the beach"
United States
Francesca
The price is AED 625
AED 791 total
includes taxes & fees
17 Nov - 18 Nov
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, (151 reviews)
"Beautiful place"
United States
Danay
The price is AED 734
AED 929 total
includes taxes & fees
18 Nov - 19 Nov
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, (6,010 reviews)
"Loved our stay"
United States
Julie anne
The price is AED 509
AED 670 total
includes taxes & fees
25 Nov - 26 Nov
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, (201 reviews)
"The room was clean and the staff were very kind."
United States
Geraldine
The price is AED 774
AED 874 total
includes taxes & fees
3 Nov - 4 Nov
SeaSpray Resort
A wooden boardwalk leading to a beach with a view of the ocean and clouds in the sky.

6. 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, (492 reviews)
"perfect"
United States
Danielle
The price is AED 682
AED 863 total
includes taxes & fees
27 Oct - 28 Oct
Haley's at The Anna Maria Island Inn
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 AED 643
AED 1,234 total
includes taxes & fees
26 Oct - 27 Oct
Pet-friendly Bradenton Home 1.5 Mi to Cortez Beach
An outdoor patio with a grill, white chairs, and a red umbrella.

8. Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key
2.5 star property
Sarasota
8.8 out of 10, Excellent, (2,472 reviews)
"This place was perfect!"
United States
Kat
The price is AED 475
AED 537 total
includes taxes & fees
26 Oct - 27 Oct
Hibiscus Suites - Gateway to Siesta Key
An aerial view of a coastal resort with a long beachfront, clear turquoise waters, and a dense cluster of buildings along the shore.

9. AMI Gulf Lookout-views Of The Gulf From Every Room-rooftop Terrace

AMI Gulf Lookout-views Of The Gulf From Every Room-rooftop Terrace
3.5 star property
Bradenton Beach
The price is AED 3,157
AED 5,054 total
includes taxes & fees
6 Nov - 7 Nov
AMI Gulf Lookout-views Of The Gulf From Every Room-rooftop Terrace
An aerial view of a coastal resort with a long beachfront, clear turquoise waters, and a dense cluster of buildings along the shore.

10. AMI Gulf Lookout-views Of The Gulf From Every Room-rooftop Terrace

AMI Gulf Lookout-views Of The Gulf From Every Room-rooftop Terrace
3.0 star property
Bradenton Beach
The price is AED 2,600
AED 4,681 total
includes taxes & fees
6 Nov - 7 Nov
AMI Gulf Lookout-views Of The Gulf From Every Room-rooftop Terrace
A beach scene with waves gently lapping at the shore and the sun setting in the distance.

11. 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 AED 236
AED 2,208 total
includes taxes & fees
30 Oct - 31 Oct
Palm Tree Villas
A large orange armchair against a white wall with a 'Captiva' sign. There are two potted plants beside the chair.

12. Captiva Beach Resort

Captiva Beach Resort
3.0 star property
South Village
9.0 out of 10, Wonderful, (1,325 reviews)
"Clean room, beach access, easy parking, friendly staff"
United States
Karla
The price is AED 573
AED 710 total
includes taxes & fees
26 Oct - 27 Oct
Captiva Beach Resort
A covered outdoor bar area with seating, a pool, and a view of the outdoors.

13. 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, (1,224 reviews)
"Great place to stay"
United States
Michael
The price is AED 879
AED 1,159 total
includes taxes & fees
1 Nov - 2 Nov
Beach House Suites by the Don CeSar
An outdoor deck with tables and chairs, a striped umbrella, and a view of the beach.

14. Alamanda Villas

Alamanda Villas
3.5 star property
Holmes Beach
8.6 out of 10, Excellent, (12 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 AED 740
AED 1,561 total
includes taxes & fees
27 Oct - 28 Oct
Alamanda Villas
A compact living space with a kitchen, a dining area, and a sofa with cushions.

15. Tiny House Siesta

Tiny House Siesta
2.0 star property
Sarasota
8.4 out of 10, Very good, (390 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 AED 220
AED 744 total
includes taxes & fees
29 Oct - 30 Oct
Tiny House Siesta
A living room with a view of the ocean, a ceiling fan, and a wooden coffee table.

16. A Beach Retreat

A Beach Retreat
2.5 star property
Casey Key
9.2 out of 10, Wonderful, (694 reviews)
"Enjoyed our stay"
United States
Robin
The price is AED 677
AED 765 total
includes taxes & fees
4 Nov - 5 Nov
A Beach Retreat
A wooden structure with a thatched roof overlooking a beach.

17. Casey Key Resort

Casey Key Resort
3.0 star property
Casey Key
8.4 out of 10, Very good, (284 reviews)
"Close to the water."
United States
jay
The price is AED 685
AED 843 total
includes taxes & fees
28 Oct - 29 Oct
Casey Key Resort
A patio with a sun lounger, a table with chairs, and an umbrella.

18. Beach View 100ft To Beach and SPA

Beach View 100ft To Beach and SPA
2.0 star property
Siesta Key Village
The price is AED 534
AED 1,338 total
includes taxes & fees
28 Oct - 29 Oct
Beach View 100ft To Beach and SPA
An indoor pool with three beach balls, a covered patio area, and a view of the surrounding garden.

19. 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
Sarasota Family Home Private Heated Pool Relax
A modern dining area with a large table, chairs, and a patterned rug.

20. Siesta Vibe Pool Walk To Crescent Beach

Siesta Vibe Pool Walk To Crescent Beach
2.0 star property
South Village
The price is AED 439
AED 1,432 total
includes taxes & fees
26 Oct - 27 Oct
Siesta Vibe Pool Walk To Crescent Beach
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Longboat Key Hotel Reviews

The Resort at Longboat Key Club

The Resort at Longboat Key Club

10/10 Excellent
"Great hotel"
Carlos 1-night trip
Posted 2 hours ago
The Resort at Longboat Key Club

Frequently asked questions

Can I find a vacation rental in Longboat Key?

Yes, we have vacation rentals near popular local attractions in Longboat Key, or you can go with a secluded option if you're looking for relaxation. 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 vacation rentals that Longboat Key has to offer?

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

How many vacation rentals are there in Longboat Key?

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

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 vacation rentals like in Longboat Key?

Vacation rentals are privately owned accommodations you can stay in for several days or more in Longboat Key. Vacation rentals offer amenities like kitchens and laundry facilities so you'll have everything you need. If you're concerned about a clean environment, vacation rentals can provide a sense of seclusion away from public hotel elevators and busy reception areas while still allowing you to travel. You'll also find more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is an attractive choice for a family getaway.