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Longboat Key Vacation Rentals

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Our top choices for Longboat Key vacation rentals

Aparthotel in South Village

Tropical Beach Resorts
3.5 star property
9.4 out of 10, Exceptional, (5,218 reviews)
"Great place to stay. Very nice getaway. "
United States
Joyeeta
$164 nightly
The price is $185
Jan 12 - Jan 13
Total with taxes and fees
Tropical Beach Resorts
3.5 star property
9.6 out of 10, Exceptional, (306 reviews)
"The rooms were perfect, and the staff was great. The location was perfect and peaceful"
United States
Marybeth
$384 nightly
The price is $434
Jan 19 - Jan 20
Total with taxes and fees
The Residences at Siesta Key Beach by Hyatt Vacation Club

Mobile Home in Sarasota

Tiny House Siesta
2.0 star property
8.4 out of 10, Very Good, (346 reviews)
"Enjoyable stay. "
United States
Lori
$207 nightly
The price is $234
Jan 27 - Jan 28
Total with taxes and fees
Tiny House Siesta

Apartment in Holmes Beach

Haley's at The Anna Maria Island Inn
3.0 star property
8.6 out of 10, Excellent, (412 reviews)
"Location was perfect and room did the job nicely for our stay."
United States
Marcellena
$131 nightly
The price is $148
Jan 12 - Jan 13
Total with taxes and fees
Haley's at The Anna Maria Island Inn

Apartment in Bradenton Beach

Pelican Post at Anna Maria Island Inn
3.0 star property
9.2 out of 10, Wonderful, (337 reviews)
"Amazing location! Clean and well kept! Adding a microwave and black out curtains would be a bonus because the room isnt dark at night due to the spot light above the door! "
United States
Bernadette
$156 nightly
The price is $177
Jan 18 - Jan 19
Total with taxes and fees
Pelican Post at Anna Maria Island Inn

Condo in South Village

Captiva Beach Resort
3.0 star property
9.0 out of 10, Wonderful, (1,188 reviews)
"Excellent place and location, "
United States
Richard
$241 nightly
The price is $270
Jan 12 - Jan 13
Total with taxes and fees
Captiva Beach Resort

Condo in Casey Key

A Beach Retreat
2.5 star property
9.2 out of 10, Wonderful, (584 reviews)
"Room was nice & staff was friendly. "
United States
Paula
$184 nightly
The price is $208
Jan 12 - Jan 13
Total with taxes and fees
A Beach Retreat

Aparthotel in Belle Vista

Beach House Suites by the Don CeSar
3.0 star property
8.8 out of 10, Excellent, (1,036 reviews)
"Great hotel "
United States
sandra
$277 nightly
The price is $314
Jan 12 - Jan 13
Total with taxes and fees
Beach House Suites by the Don CeSar
2.5 star property
8.6 out of 10, Excellent, (2,229 reviews)
"Very nice place !"
United States
Ivette
$144 nightly
The price is $163
Jan 14 - Jan 15
Total with taxes and fees
Hibiscus Suites - Gateway to Siesta Key

Apartment in Bradenton Beach

Seabreeze at Anna Maria Island Inn
3.0 star property
9.0 out of 10, Wonderful, (68 reviews)
"Very great stay will stay again "
United States
Joseph
$182 nightly
The price is $206
Jan 13 - Jan 14
Total with taxes and fees
Seabreeze at Anna Maria Island Inn

Vacation Home in Siesta Key

Siesta Heron Suites & Villas
3.5 star property
8.6 out of 10, Excellent, (38 reviews)
"Clean pool great apartment could use more seating in living room. Beach chairs was cool patio was awesome parking good water pressure great bed clean and comfy "
United States
jason
$308 nightly
The price is $349
Jan 13 - Jan 14
Total with taxes and fees
Siesta Heron Suites & Villas

Apartment in Holmes Beach

Palm Tree Villas
3.0 star property
9.2 out of 10, Wonderful, (172 reviews)
"We had a great stay! The property was located within a short walk to the beach. We will be back!"
United States
Anonymous traveler
$576 nightly
The price is $632
Jan 13 - Jan 14
Total with taxes and fees
Palm Tree Villas

Aparthotel in Bridge Street

Bridgewalk Resort
3.5 star property
9.4 out of 10, Exceptional, (772 reviews)
"Staff was great, room very nice"
United States
LeeAnn
$236 nightly
The price is $267
Jan 25 - Jan 26
Total with taxes and fees
Bridgewalk Resort

Cottage in Siesta Key

The Inn On Siesta Key
3.5 star property
10.0 out of 10, Exceptional, (192 reviews)
"Great place to stay! "
United States
Carlos
$210 nightly
The price is $238
Jan 12 - Jan 13
Total with taxes and fees
The Inn On Siesta Key
2.0 star property
10.0 out of 10, Exceptional, (1 review)
"Great little place to stay and enjoy the nearby beaches and restaurants! The communication was on point. We will be back "
United States
Jacob
$364 nightly
The price is $410
Jan 18 - Jan 19
Total with taxes and fees
Coastal Breeze Siesta - Turtle

Apartment in Casey Key

Casey Key Resort - Gulf Shores
3.0 star property
8.4 out of 10, Very Good, (267 reviews)
"Very helpful and nice staff. Lovely room, great location. Adorable cottage"
United States
Hilary
$372 nightly
The price is $420
Jan 12 - Jan 13
Total with taxes and fees
Casey Key Resort - Gulf Shores

Aparthotel in Siesta Key

SeaSpray Resort
4.0 star property
9.4 out of 10, Exceptional, (84 reviews)
"Very clean very quiet and a great location to the beach."
United States
Dave
$339 nightly
The price is $383
Jan 12 - Jan 13
Total with taxes and fees
SeaSpray Resort
3.0 star property
$430 nightly
The price is $482
Feb 8 - Feb 9
Total with taxes and fees
3 Mi to Downtown Bradenton: Family Home w/ Yard!

Condo in Holmes Beach

Alamanda Villas
3.5 star property
9.6 out of 10, Exceptional, (4 reviews)
"The location is wonderful for beach access,places to eat and grocery is block away. Small parking area if more than one couple stay. Had a great stay."
United States
Traci
$421 nightly
The price is $454
Jan 12 - Jan 13
Total with taxes and fees
Alamanda Villas
2.0 star property
$828 nightly
The price is $936
Jan 12 - Jan 13
Total with taxes and fees
Waterfront Heated Pool House Kayaks Boat Dock
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
This month
Next month
January
March
$320
$459
Month
Price
January
$320
February
$459
March
$556
April
$454
May
$419
June
$495
July
$482
August
$413
September
$359
October
$358
November
$371
December
$394
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 $335 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.

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 free 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 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. Siesta Key Beach and St. Armands Circle 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.