Longboat Key Vacation Rentals

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Our top choices for Longboat Key vacation rentals

Venice Beach Villas

Venice Beach Villas
3.0 star property
Venice Island
9.4 out of 10, Exceptional, (478 reviews)
"Exceptional location both to the beach and restaurants. The facility has everything you need to augment your stay: bikes, beach chairs and umbrellas, coolers and pool floats. The room is immaculate too."
United States
Kathy
$152 nightly
The price is $172
May 11 - May 12
Total with taxes and fees
Venice Beach Villas

4 Mi to Siesta Key Beach: Condo w/ Private Patio

4 Mi to Siesta Key Beach: Condo w/ Private Patio
3.5 star property
Sarasota
$309 nightly
The price is $345
Apr 19 - Apr 20
Total with taxes and fees
4 Mi to Siesta Key Beach: Condo w/ Private Patio

A Beach Retreat

A Beach Retreat
2.5 star property
Casey Key
9.2 out of 10, Wonderful, (620 reviews)
"Love this place"
United States
Marialis
$189 nightly
The price is $214
Apr 27 - Apr 28
Total with taxes and fees
A Beach Retreat

Bridgewalk Resort

Bridgewalk Resort
3.5 star property
Bridge Street
9.4 out of 10, Exceptional, (789 reviews)
"So nice to walk to restaurants and shops. Very walkable. Clean. Updated and relaxing atmosphere. Parking was really convenient and accessible. Would stay again."
United States
Deborah
$263 nightly
The price is $297
Apr 29 - Apr 30
Total with taxes and fees
Bridgewalk Resort

Tropical Beach Resorts

Tropical Beach Resorts
3.5 star property
South Village
9.4 out of 10, Exceptional, (5,414 reviews)
"We had a very nice time and the resort was centrally located and right down the road from the beach. "
United States
Christopher Kevin
$226 nightly
The price is $256
Apr 30 - May 1
Total with taxes and fees
Tropical Beach Resorts

Family Fun: Ping Pong, Bbq, Walk to Park Nearby

Family Fun: Ping Pong, Bbq, Walk to Park Nearby
3.0 star property
Fruitville
$501 nightly
The price is $566
Apr 17 - Apr 18
Total with taxes and fees
Family Fun: Ping Pong, Bbq, Walk to Park Nearby

Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key
2.5 star property
Sarasota
8.6 out of 10, Excellent, (2,281 reviews)
"Clean room, quiet and in a location convenient to Siesta Key. The pool is very nice, although located at the front of the property alongside a busy road. Would definitely recommend this hotel, especially if a kitchenette is desired."
United States
CAROLYN
$163 nightly
The price is $184
Apr 14 - Apr 15
Total with taxes and fees
Hibiscus Suites - Gateway to Siesta Key

Siesta Heron Suites & Villas

Siesta Heron Suites & Villas
3.5 star property
Siesta Key
8.4 out of 10, Very Good, (41 reviews)
"Clean rooms, convenient location, nice property and amenities. Simple check-in and check-out"
United States
Christopher Robert
$303 nightly
The price is $342
Apr 14 - Apr 15
Total with taxes and fees
Siesta Heron Suites & Villas

Tropical Villas of Venice Beach

Tropical Villas of Venice Beach
3.5 star property
Venice Island
9.6 out of 10, Exceptional, (247 reviews)
"Staff very accommodating."
United States
Genevieve
$209 nightly
The price is $236
Apr 23 - Apr 24
Total with taxes and fees
Tropical Villas of Venice Beach

Tiny House Siesta

Tiny House Siesta
2.0 star property
Sarasota
8.4 out of 10, Very Good, (362 reviews)
"super clean and comfortable. we were 4 people and had a very comfortable and lovely stay. i felt super at home and the location is very centralized to everything "
United States
Adanna
$198 nightly
The price is $223
Apr 27 - Apr 28
Total with taxes and fees
Tiny House Siesta

Sleeps 8 Pets Welcome Fenced In Backyard

Sleeps 8 Pets Welcome Fenced In Backyard
2.0 star property
Southgate
$294 nightly
The price is $332
Apr 14 - Apr 15
Total with taxes and fees
Sleeps 8 Pets Welcome Fenced In Backyard

Siesta Key Island Rentals

Siesta Key Island Rentals
3.0 star property
Siesta Key
9.6 out of 10, Exceptional, (65 reviews)
"We had a wonderful time-perfect location to beach and village. Was nice to come back to a very comfortable and relaxing home. Definitely recommend-5 stars! "
United States
Laura
$361 nightly
The price is $408
Apr 15 - Apr 16
Total with taxes and fees
Siesta Key Island Rentals

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, (1,078 reviews)
"Great place, would absolutely stay again."
United States
Malik
$399 nightly
The price is $451
May 11 - May 12
Total with taxes and fees
Beach House Suites by the Don CeSar

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, (388 reviews)
"Love this place "
United States
Leeanne
$257 nightly
The price is $290
May 12 - May 13
Total with taxes and fees
Pelican Post at Anna Maria Island Inn

Captiva Beach Resort

Captiva Beach Resort
3.0 star property
South Village
9.0 out of 10, Wonderful, (1,230 reviews)
"Clean and very close to beach. "
United States
Daniel
$235 nightly
The price is $263
Apr 19 - Apr 20
Total with taxes and fees
Captiva Beach Resort

Artsy Getaway With Vibrant Design Flair

Artsy Getaway With Vibrant Design Flair
3.5 star property
Arlington Park
$273 nightly
The price is $309
Apr 20 - Apr 21
Total with taxes and fees
Artsy Getaway With Vibrant Design Flair

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, (443 reviews)
"Incredible location, great room! Loved everything! Would def come back!"
United States
Laís Fernanda
$300 nightly
The price is $339
May 12 - May 13
Total with taxes and fees
Haley's at The Anna Maria Island Inn

SeaSpray Resort

SeaSpray Resort
4.0 star property
Siesta Key
9.6 out of 10, Exceptional, (106 reviews)
"Perfect location, nice amenities for the beach, pet friendly, would stay here again! Super convenient and clean "
United States
Jayline
$309 nightly
The price is $349
May 4 - May 5
Total with taxes and fees
SeaSpray Resort

Alamanda Villas

Alamanda Villas
3.5 star property
Holmes Beach
9.0 out of 10, Wonderful, (8 reviews)
"Very clean and the perfect location! Close to the beach, restaurants, and the grocery! We loved the heated pool in February. "
United States
Robert
$448 nightly
The price is $484
May 14 - May 15
Total with taxes and fees
Alamanda Villas

Casey Key Resort - Gulf Shores

Casey Key Resort - Gulf Shores
3.0 star property
Casey Key
8.4 out of 10, Very Good, (272 reviews)
"Great place"
United States
tony
$219 nightly
The price is $247
May 3 - May 4
Total with taxes and fees
Casey Key Resort - Gulf Shores
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
September
February
$428
$417
Month
Price
January
$438
February
$560
March
$507
April
$428
May
$417
June
$501
July
$494
August
$449
September
$389
October
$402
November
$416
December
$436
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 $313 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 21 Expedia vacation rentals in Longboat Key for a memorable vacation.

What can I see and do in Longboat Key?

Jewfish Key and Longboat Key Beaches 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.