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

Longboat Key Vacation Rentals

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Our top choices for Longboat Key vacation rentals

1. 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, (450 reviews)
"Great place to stay,"
United States
Wilson
$163 nightly
The price is $185
Sep 22 - Sep 23
Total with taxes and fees
Pelican Post at Anna Maria Island Inn

2. Bridgewalk Resort

Bridgewalk Resort
3.5 star property
Bridge Street
9.4 out of 10, Exceptional, (825 reviews)
"loved it here"
United States
Hannah
$286 nightly
The price is $323
Aug 30 - Aug 31
Total with taxes and fees
Bridgewalk Resort

3. Cedar Run Resort - Roam Hospitality

Cedar Run Resort - Roam Hospitality
3.5 star property
South Bradenton
9.4 out of 10, Exceptional, (8 reviews)
"I would stay again, very accommodating"
United States
Deliondra
$373 nightly
The price is $422
Aug 31 - Sep 1
Total with taxes and fees
Cedar Run Resort - Roam Hospitality

4. 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, (476 reviews)
"Very clean room and just a short walk to the beach!"
United States
Ivet
$178 nightly
The price is $201
Sep 3 - Sep 4
Total with taxes and fees
Haley's at The Anna Maria Island Inn

5. Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key
2.5 star property
Sarasota
8.6 out of 10, Excellent, (2,429 reviews)
"This place was perfect!"
United States
Kat
$127 nightly
The price is $144
Sep 2 - Sep 3
Total with taxes and fees
Hibiscus Suites - Gateway to Siesta Key

6. 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
Aug 31 - Sep 1
Total with taxes and fees
Pet-friendly Bradenton Home 1.5 Mi to Cortez Beach

7. Tropical Beach Resorts

Tropical Beach Resorts
3.5 star property
South Village
9.4 out of 10, Exceptional, (5,797 reviews)
"Great place to visit!"
United States
Margaret Lai Ling
$134 nightly
The price is $152
Sep 2 - Sep 3
Total with taxes and fees
Tropical Beach Resorts

8. Gulf to Bay Island Oasis

Gulf to Bay Island Oasis
2.0 star property
Bradenton Beach
$545 nightly
The price is $616
Sep 8 - Sep 9
Total with taxes and fees
Gulf to Bay Island Oasis

9. DOLPHIN PRIVATE HOUSE

DOLPHIN PRIVATE HOUSE
3.0 star property
Siesta Key Village
$522 nightly
The price is $590
Aug 30 - Aug 31
Total with taxes and fees
DOLPHIN PRIVATE HOUSE

10. SeaSpray Resort

SeaSpray Resort
4.0 star property
Siesta Key
9.6 out of 10, Exceptional, (174 reviews)
"Beautiful hotel comfortable bed nice and friendly staff!!!!"
United States
Isabel
$202 nightly
The price is $228
Sep 2 - Sep 3
Total with taxes and fees
SeaSpray Resort

11. Seabreeze at Anna Maria Island Inn

Seabreeze at Anna Maria Island Inn
3.0 star property
Bradenton Beach
8.8 out of 10, Excellent, (124 reviews)
"I love how close I was to the beach"
United States
Rixie
$196 nightly
The price is $222
Sep 2 - Sep 3
Total with taxes and fees
Seabreeze at Anna Maria Island Inn

12. Tiny House Siesta

Tiny House Siesta
2.0 star property
Sarasota
8.4 out of 10, Very Good, (384 reviews)
"Great place"
United States
Mario
$197 nightly
The price is $222
Sep 7 - Sep 8
Total with taxes and fees
Tiny House Siesta

13. 3716 7th Ave W

3716 7th Ave W
3.0 star property
Bradenton
$2,691 nightly
The price is $3,040
Sep 3 - Sep 4
Total with taxes and fees
3716 7th Ave W

14. Sun Outdoors Sarasota

Sun Outdoors Sarasota
2.5 star property
Fordville
$410 nightly
The price is $463
Sep 11 - Sep 12
Total with taxes and fees
Sun Outdoors Sarasota

15. 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
$622 nightly
The price is $684
Aug 31 - Sep 1
Total with taxes and fees
Palm Tree Villas

16. Explore Sarasota: Condo w/ Pool Access, Near Dtwn

Explore Sarasota: Condo w/ Pool Access, Near Dtwn
3.5 star property
Sarasota
$254 nightly
The price is $287
Aug 30 - Aug 31
Total with taxes and fees
Explore Sarasota: Condo w/ Pool Access, Near Dtwn

17. 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
$435 nightly
The price is $470
Sep 28 - Sep 29
Total with taxes and fees
Alamanda Villas

18. Pineapple Paradise 1 13 min to Beach Fire Pit

Pineapple Paradise 1 13 min to Beach Fire Pit
2.0 star property
Central Sarasota
$331 nightly
The price is $375
Aug 30 - Aug 31
Total with taxes and fees
Pineapple Paradise 1 13 min to Beach Fire Pit

19. 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, (1,176 reviews)
"Great place to stay"
United States
Michael
$211 nightly
The price is $239
Aug 30 - Aug 31
Total with taxes and fees
Beach House Suites by the Don CeSar

20. Lulu's Key House Green 1/1 Upstairs

Lulu's Key House Green 1/1 Upstairs
3.5 star property
Siesta Key Village
$428 nightly
The price is $483
Aug 30 - Aug 31
Total with taxes and fees
Lulu's Key House Green 1/1 Upstairs
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

Price trends for vacation rentals in Longboat Key

Less expensive
More expensive
Next month
October
February
$374
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 $304 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?

Siesta Key Island Rentals: This vacation home rental near Longboat Key comes with WiFi so you can feel at home during your trip. This vacation rental also comes with free parking to give you added peace of mind.

How many vacation rentals are there in Longboat Key?

Choose from 20 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. Siesta Key Beach and Lido 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.