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. 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 CA $405
CA $497 total
includes taxes & fees
Oct 26 - Oct 27
Bridgewalk Resort

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 CA $238
CA $302 total
includes taxes & fees
Nov 17 - Nov 18
Pelican Post at Anna Maria Island Inn

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 CA $263
CA $333 total
includes taxes & fees
Nov 18 - Nov 19
Seabreeze at Anna Maria Island Inn

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
The price is CA $194
CA $256 total
includes taxes & fees
Nov 24 - Nov 25
Tropical Beach Resorts

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 CA $292
CA $330 total
includes taxes & fees
Nov 2 - Nov 3
SeaSpray Resort

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 CA $244
CA $309 total
includes taxes & fees
Oct 28 - Oct 29
Haley's at The Anna Maria Island Inn

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 CA $245
CA $470 total
includes taxes & fees
Oct 26 - Oct 27
Pet-friendly Bradenton Home 1.5 Mi to Cortez Beach

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 CA $164
CA $185 total
includes taxes & fees
Nov 24 - Nov 25
Hibiscus Suites - Gateway to Siesta Key

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 CA $1,203
CA $1,927 total
includes taxes & fees
Nov 6 - Nov 7
AMI Gulf Lookout-views Of The Gulf From Every Room-rooftop Terrace

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 CA $991
CA $1,785 total
includes taxes & fees
Nov 6 - Nov 7
AMI Gulf Lookout-views Of The Gulf From Every Room-rooftop Terrace

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 CA $90
CA $842 total
includes taxes & fees
Oct 30 - Oct 31
Palm Tree Villas

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 CA $219
CA $271 total
includes taxes & fees
Oct 26 - Oct 27
Captiva Beach Resort

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 CA $335
CA $442 total
includes taxes & fees
Nov 4 - Nov 5
Beach House Suites by the Don CeSar

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 CA $273
CA $583 total
includes taxes & fees
Oct 26 - Oct 27
Alamanda Villas

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 CA $77
CA $276 total
includes taxes & fees
Oct 30 - Oct 31
Tiny House Siesta

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 CA $258
CA $292 total
includes taxes & fees
Nov 4 - Nov 5
A Beach Retreat

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 CA $261
CA $321 total
includes taxes & fees
Oct 28 - Oct 29
Casey Key Resort

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 CA $196
CA $502 total
includes taxes & fees
Oct 26 - Oct 27
Beach View 100ft To Beach and SPA

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

20. Siesta Vibe Pool Walk To Crescent Beach

Siesta Vibe Pool Walk To Crescent Beach
2.0 star property
South Village
The price is CA $167
CA $546 total
includes taxes & fees
Oct 26 - Oct 27
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.
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Top Longboat Key Hotel Reviews

Find out more about Longboat Key

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Longboat Key. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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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?

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.