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, (454 reviews)
"Great place to stay,"
United States
Wilson
The price is CA $207
CA $262 total
includes taxes & fees
Sep 22 - Sep 23
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)
"The hotel was wonderful. Nice staff, room and location. Free beach chairs, towels and umbrella to use at the beach which is right across the street."
United States
robin
The price is CA $402
CA $454 total
includes taxes & fees
Sep 8 - Sep 9
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
The price is CA $177
CA $597 total
includes taxes & fees
Sep 2 - Sep 3
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, (477 reviews)
"Very clean room and just a short walk to the beach!"
United States
Ivet
The price is CA $225
CA $285 total
includes taxes & fees
Sep 1 - Sep 2
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, (2,433 reviews)
"This place was perfect!"
United States
Kat
The price is CA $157
CA $178 total
includes taxes & fees
Sep 9 - Sep 10
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
The price is CA $243
CA $467 total
includes taxes & fees
Sep 1 - Sep 2
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, (5,815 reviews)
"Great place to visit!"
United States
Margaret Lai Ling
The price is CA $155
CA $211 total
includes taxes & fees
Sep 2 - Sep 3
Tropical Beach Resorts

8. Gulf to Bay Island Oasis

Gulf to Bay Island Oasis
2.0 star property
Bradenton Beach
The price is CA $263
CA $816 total
includes taxes & fees
Sep 8 - Sep 9
Gulf to Bay Island Oasis

9. DOLPHIN PRIVATE HOUSE

DOLPHIN PRIVATE HOUSE
3.0 star property
Siesta Key Village
The price is CA $738
CA $834 total
includes taxes & fees
Sep 1 - Sep 2
DOLPHIN PRIVATE HOUSE

10. SeaSpray Resort

SeaSpray Resort
4.0 star property
Siesta Key
9.6 out of 10, Exceptional, (175 reviews)
"Beautiful hotel comfortable bed nice and friendly staff!!!!"
United States
Isabel
The price is CA $269
CA $304 total
includes taxes & fees
Sep 2 - Sep 3
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, (127 reviews)
"Right on beach, in a good area. Comfy beds, would stay here again"
United States
Katelyn
The price is CA $263
CA $333 total
includes taxes & fees
Sep 10 - Sep 11
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
The price is CA $115
CA $319 total
includes taxes & fees
Sep 11 - Sep 12
Tiny House Siesta

13. 3716 7th Ave W

3716 7th Ave W
3.0 star property
Bradenton
The price is CA $3,183
CA $4,179 total
includes taxes & fees
Sep 3 - Sep 4
3716 7th Ave W

14. Sun Outdoors Sarasota

Sun Outdoors Sarasota
2.5 star property
Fordville
The price is CA $601
CA $679 total
includes taxes & fees
Sep 8 - Sep 9
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
The price is CA $196
CA $992 total
includes taxes & fees
Sep 6 - Sep 7
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
The price is CA $132
CA $399 total
includes taxes & fees
Sep 1 - Sep 2
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
The price is CA $303
CA $620 total
includes taxes & fees
Sep 27 - Sep 28
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
The price is CA $161
CA $527 total
includes taxes & fees
Sep 1 - Sep 2
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, (1,180 reviews)
"Great place to stay"
United States
Michael
The price is CA $240
CA $335 total
includes taxes & fees
Sep 1 - Sep 2
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
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

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, cottages, cabins, villas... 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Longboat Key vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Longboat Key vacation rentals we have selected for you start as low as CA $420 per night. Entering your travel dates in the search wizard 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. 

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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 21 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.