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

Longboat Key Vacation Rentals

Check prices for these dates

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

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
$314 nightly
The price is $355
Oct 26 - Oct 27
Total with taxes and fees
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
$203 nightly
The price is $229
Nov 2 - Nov 3
Total with taxes and fees
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, (150 reviews)
"Beautiful place"
United States
Danay
$204 nightly
The price is $230
Nov 18 - Nov 19
Total with taxes and fees
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, (6,009 reviews)
"Loved our stay"
United States
Julie anne
$163 nightly
The price is $184
Nov 25 - Nov 26
Total with taxes and fees
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
$209 nightly
The price is $236
Nov 2 - Nov 3
Total with taxes and fees
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
$196 nightly
The price is $221
Oct 28 - Oct 29
Total with taxes and fees
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
$297 nightly
The price is $336
Oct 26 - Oct 27
Total with taxes and fees
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
$123 nightly
The price is $139
Oct 26 - Oct 27
Total with taxes and fees
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
$1,218 nightly
The price is $1,376
Nov 6 - Nov 7
Total with taxes and fees
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
$1,137 nightly
The price is $1,275
Nov 6 - Nov 7
Total with taxes and fees
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
$560 nightly
The price is $613
Oct 30 - Oct 31
Total with taxes and fees
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
$173 nightly
The price is $194
Oct 28 - Oct 29
Total with taxes and fees
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
$283 nightly
The price is $320
Nov 1 - Nov 2
Total with taxes and fees
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
$408 nightly
The price is $439
Oct 27 - Oct 28
Total with taxes and fees
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
$179 nightly
The price is $202
Oct 29 - Oct 30
Total with taxes and fees
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
$205 nightly
The price is $231
Nov 4 - Nov 5
Total with taxes and fees
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
$236 nightly
The price is $264
Oct 26 - Oct 27
Total with taxes and fees
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
$321 nightly
The price is $362
Oct 26 - Oct 27
Total with taxes and fees
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 spacious living area with a dining table, black chairs, a white sofa, 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
$358 nightly
The price is $405
Oct 26 - Oct 27
Total with taxes and fees
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 BEACH CONDO #107 BEACHFRONT FULL VIEW

THE BEACH CONDO #107 BEACHFRONT FULL VIEW

8/10 Good
"Close to beach and cozy"
Peter 1-night trip
Posted 15 hours ago
THE BEACH CONDO #107 BEACHFRONT FULL VIEW

Price trends for vacation rentals in Longboat Key

Less expensive
More expensive
Next month
October
February
$394
Month
Price
January
$430
February
$539
March
$484
April
$441
May
$409
June
$463
July
$458
August
$384
September
$374
October
$371
November
$394
December
$429
Price trend information excludes taxes and fees and is based on base rates for a nightly stay for 2 adults found in the last 7 days on our site and averaged for commonly viewed vacation rentals in Longboat Key. Select dates and complete search for nightly totals inclusive of taxes and fees.

Find out more about Longboat Key

Everything you need to know about Longboat Key vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Longboat Key vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Longboat Key vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Longboat Key vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Longboat Key. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Longboat Key in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $336 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Longboat Key rentals

At Expedia, we put the best Longboat Key vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Longboat Key rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Longboat Key vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Longboat Key. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

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.