Longboat Key Holiday Rentals

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Our top choices for Longboat Key holiday 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
The price is AU$238
includes taxes & fees
1 May - 2 May
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
The price is AU$481
includes taxes & fees
19 Apr - 20 Apr
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, (621 reviews)
"Love this place"
United States
Marialis
The price is AU$268
includes taxes & fees
3 May - 4 May
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
The price is AU$425
includes taxes & fees
3 May - 4 May
Bridgewalk Resort

Tropical Beach Resorts

Tropical Beach Resorts
3.5 star property
South Village
9.4 out of 10, Exceptional, (5,420 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
The price is AU$330
includes taxes & fees
22 Apr - 23 Apr
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
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, (2,285 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
The price is AU$252
includes taxes & fees
19 Apr - 20 Apr
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
The price is AU$469
includes taxes & fees
27 Apr - 28 Apr
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
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
The price is AU$307
includes taxes & fees
27 Apr - 28 Apr
Tiny House Siesta

Sleeps 8 Pets Welcome Fenced In Backyard

Sleeps 8 Pets Welcome Fenced In Backyard
2.0 star property
Southgate
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
The price is AU$601
includes taxes & fees
19 Apr - 20 Apr
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, (1,079 reviews)
"Great place, would absolutely stay again."
United States
Malik
The price is AU$572
includes taxes & fees
13 May - 14 May
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, (389 reviews)
"Love this place "
United States
Leeanne
The price is AU$386
includes taxes & fees
12 May - 13 May
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, (1,232 reviews)
"Clean and very close to beach. "
United States
Daniel
The price is AU$341
includes taxes & fees
19 Apr - 20 Apr
Captiva Beach Resort

Artsy Getaway With Vibrant Design Flair

Artsy Getaway With Vibrant Design Flair
3.5 star property
Arlington Park
The price is AU$427
includes taxes & fees
21 Apr - 22 Apr
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, (444 reviews)
"Incredible location, great room! Loved everything! Would def come back!"
United States
Laís Fernanda
The price is AU$425
includes taxes & fees
12 May - 13 May
Haley's at The Anna Maria Island Inn

SeaSpray Resort

SeaSpray Resort
4.0 star property
Siesta Key
9.6 out of 10, Exceptional, (107 reviews)
"Perfect location, nice amenities for the beach, pet friendly, would stay here again! Super convenient and clean "
United States
Jayline
The price is AU$487
includes taxes & fees
6 May - 7 May
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
The price is AU$641
includes taxes & fees
7 May - 8 May
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
The price is AU$302
includes taxes & fees
3 May - 4 May
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

Find out more about Longboat Key

Everything you need to know about Longboat Key holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Longboat Key holiday rental for you. At Expedia, you can take your pick from private holiday 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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Longboat Key holiday 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 depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Longboat Key holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Longboat Key holiday rentals we have selected for you start as low as AU$472 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Longboat Key rentals

At Expedia, we put the best Longboat Key holiday 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 holiday.

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 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?

Siesta Key Island Rentals: This holiday home rental outside of Longboat Key comes with free WiFi so that you can feel at home during your trip. This holiday rental also comes with free parking to give you added peace of mind.

How many holiday rentals are there in Longboat Key?

Choose from 21 Expedia holiday rentals in Longboat Key for a memorable holiday.

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 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.