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Longboat Key Holiday Rentals

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Our top choices for Longboat Key holiday 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 NZ$623
includes taxes & fees
26 Oct - 27 Oct
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 NZ$378
includes taxes & fees
17 Nov - 18 Nov
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, (150 reviews)
"Beautiful place"
United States
Danay
The price is NZ$422
includes taxes & fees
18 Nov - 19 Nov
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 NZ$324
includes taxes & fees
24 Nov - 25 Nov
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 NZ$413
includes taxes & fees
2 Nov - 3 Nov
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 NZ$388
includes taxes & fees
28 Oct - 29 Oct
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 NZ$590
includes taxes & fees
26 Oct - 27 Oct
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 NZ$267
includes taxes & fees
4 Nov - 5 Nov
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 NZ$2,414
includes taxes & fees
6 Nov - 7 Nov
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 NZ$2,236
includes taxes & fees
6 Nov - 7 Nov
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 NZ$1,055
includes taxes & fees
30 Oct - 31 Oct
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 NZ$339
includes taxes & fees
26 Oct - 27 Oct
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 NZ$554
includes taxes & fees
2 Nov - 3 Nov
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 NZ$756
includes taxes & fees
26 Oct - 27 Oct
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 NZ$356
includes taxes & fees
30 Oct - 31 Oct
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 NZ$365
includes taxes & fees
4 Nov - 5 Nov
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 NZ$403
includes taxes & fees
28 Oct - 29 Oct
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 NZ$652
includes taxes & fees
26 Oct - 27 Oct
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 NZ$684
includes taxes & fees
26 Oct - 27 Oct
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 holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Longboat Key holiday 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. 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 holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Longboat Key. 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 Longboat Key. 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 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 holiday 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 Longboat Key short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find a holiday rental in Longboat Key?

Yes, there are holiday rentals close to the most popular sights in Longboat Key, or you can select a more secluded option if you're looking for a relaxing stay. 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 holiday rentals that Longboat Key has to offer?

Tropical Villas of Venice Beach: This holiday home rental outside of Longboat Key is located near the beach, and has an outdoor pool, a terrace and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a microwave and kitchenware. Make the most of garden in this rental home to help you unwind.

How many holiday rentals are there in Longboat Key?

Choose from 17 Expedia holiday rentals in Longboat Key for a memorable holiday.

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 holiday rentals like in Longboat Key?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Longboat Key. Holiday rentals offer extras like WiFi and washers and dryers so you'll have all the comforts of home. If you're concerned about a clean environment, holiday rentals can provide a sense of privacy away from public hotel lifts and bustling concierge desks while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a popular choice for a family trip.