Longboat Key Vacation Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

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
The price is P6,834
P7,722 total
includes taxes & fees
May 11 - May 12
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 P8,099
P22,414 total
includes taxes & fees
Apr 19 - Apr 20
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 P10,205
P11,532 total
includes taxes & fees
May 12 - May 13
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 P17,333
P19,586 total
includes taxes & fees
May 3 - May 4
Bridgewalk Resort

Tropical Beach Resorts

Tropical Beach Resorts
3.5 star property
South Village
9.4 out of 10, Exceptional, (5,424 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 P11,678
P14,756 total
includes taxes & fees
May 3 - May 4
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 P9,592
P10,839 total
includes taxes & fees
May 4 - May 5
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 P8,050
P21,185 total
includes taxes & fees
May 12 - May 13
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
The price is P10,205
P12,888 total
includes taxes & fees
Apr 23 - Apr 24
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 P5,414
P13,421 total
includes taxes & fees
May 10 - May 11
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 P13,324
P26,317 total
includes taxes & fees
Apr 22 - Apr 23
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 P15,632
P20,381 total
includes taxes & fees
Apr 20 - Apr 21
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 P14,929
P18,894 total
includes taxes & fees
May 12 - May 13
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 P12,368
P14,994 total
includes taxes & fees
Apr 29 - Apr 30
Captiva Beach Resort

Artsy Getaway With Vibrant Design Flair

Artsy Getaway With Vibrant Design Flair
3.5 star property
Arlington Park
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 P14,678
P18,577 total
includes taxes & fees
May 5 - May 6
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 P18,571
P20,985 total
includes taxes & fees
May 4 - May 5
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 P15,539
P29,878 total
includes taxes & fees
May 4 - May 5
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 P10,980
P13,028 total
includes taxes & fees
May 3 - May 4
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Longboat Key Hotel Reviews

Find out more about Longboat Key

Search for holiday rentals in Longboat Key on Expedia! You can easily find your home rentals, villas, holiday apartments in Longboat Key using one of the methods below:

  • View our selection of featured holiday rentals in Longboat Key
  • Use the map to find apartments and other holiday homes in the Longboat Key neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Longboat Key while they last

Look no further and take a look at our great range of rental properties in Longboat Key!

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.