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

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, (834 reviews)
"I loved this hotel"
United States
Raisare
$314 nightly
The price is $355
Oct 6 - Oct 7
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, (474 reviews)
"Great location and walking distance to the beach"
United States
Francesca
$214 nightly
The price is $241
Oct 6 - Oct 7
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, (139 reviews)
"Right on beach, in a good area. Comfy beds, would stay here again"
United States
Katelyn
$266 nightly
The price is $301
Oct 4 - Oct 5
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, (5,932 reviews)
"Amazing resort,"
United States
kurt
$158 nightly
The price is $179
Oct 4 - Oct 5
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, (186 reviews)
"Property and room were beautiful!! Right across the street from the beach ⛱️"
United States
Michelle Suzanne
$234 nightly
The price is $265
Oct 20 - Oct 21
Total with taxes and fees
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
$297 nightly
The price is $336
Oct 2 - Oct 3
Total with taxes and fees
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
$199 nightly
The price is $225
Oct 7 - Oct 8
Total with taxes and fees
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, (2,456 reviews)
"This place was perfect!"
United States
Kat
$127 nightly
The price is $144
Oct 15 - Oct 16
Total with taxes and fees
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
$177 nightly
The price is $197
Oct 6 - Oct 7
Total with taxes and fees
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, (1,201 reviews)
"Great place to stay"
United States
Michael
$280 nightly
The price is $316
Oct 5 - Oct 6
Total with taxes and fees
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
$583 nightly
The price is $640
Oct 4 - Oct 5
Total with taxes and fees
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
$431 nightly
The price is $466
Nov 1 - Nov 2
Total with taxes and fees
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
$181 nightly
The price is $205
Oct 8 - Oct 9
Total with taxes and fees
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
$486 nightly
The price is $550
Oct 6 - Oct 7
Total with taxes and fees
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
$313 nightly
The price is $354
Oct 4 - Oct 5
Total with taxes and fees
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
$210 nightly
The price is $237
Oct 4 - Oct 5
Total with taxes and fees
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
$341 nightly
The price is $385
Oct 4 - Oct 5
Total with taxes and fees
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
$236 nightly
The price is $264
Oct 2 - Oct 3
Total with taxes and fees
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, (45 reviews)
"Clean rooms, convenient location, nice property and amenities. Simple check-in and check-out"
United States
Christopher Robert
$276 nightly
The price is $312
Oct 6 - Oct 7
Total with taxes and fees
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 1 day ago
The Resort at Longboat Key Club

Price trends for vacation rentals in Longboat Key

Less expensive
More expensive
This month
Next month
October
February
$371
$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 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.