A coastal cityscape with a sunset over the water, featuring several high-rise buildings and palm trees.

Longboat Key Vacation Rentals

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Check prices for these dates

In two weeks
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

Our top choices for Longboat Key vacation rentals

A modern building with a white exterior, a brick gable, and a palm tree in the foreground.

1. 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, (454 reviews)
"Great place to stay,"
United States
Wilson
The price is P9,975
P12,624 total
includes taxes & fees
Sep 22 - Sep 23
Pelican Post at Anna Maria Island Inn
A two-story building with a balcony, palm trees, and outdoor seating.

2. Bridgewalk Resort

Bridgewalk Resort
3.5 star property
Bridge Street
9.4 out of 10, Exceptional, (826 reviews)
"The hotel was wonderful. Nice staff, room and location. Free beach chairs, towels and umbrella to use at the beach which is right across the street."
United States
robin
The price is P17,994
P20,333 total
includes taxes & fees
Sep 8 - Sep 9
Bridgewalk Resort
A water slide in a pool area with a rocky backdrop and a small waterfall.

3. Cedar Run Resort - Roam Hospitality

Cedar Run Resort - Roam Hospitality
3.5 star property
South Bradenton
9.4 out of 10, Exceptional, (8 reviews)
"I would stay again, very accommodating"
United States
Deliondra
The price is P8,592
P27,510 total
includes taxes & fees
Sep 3 - Sep 4
Cedar Run Resort - Roam Hospitality
A wooden boardwalk leading to a beach with a view of the ocean and clouds in the sky.

4. 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, (477 reviews)
"Very clean room and just a short walk to the beach!"
United States
Ivet
The price is P9,416
P11,917 total
includes taxes & fees
Sep 3 - Sep 4
Haley's at The Anna Maria Island Inn
An outdoor patio with a grill, white chairs, and a red umbrella.

5. Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key
2.5 star property
Sarasota
8.6 out of 10, Excellent, (2,434 reviews)
"This place was perfect!"
United States
Kat
The price is P8,473
P9,574 total
includes taxes & fees
Sep 2 - Sep 3
Hibiscus Suites - Gateway to Siesta Key
A modern outdoor seating area with two blue chairs and a large potted plant.

6. 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 P10,896
P20,919 total
includes taxes & fees
Sep 2 - Sep 3
Pet-friendly Bradenton Home 1.5 Mi to Cortez Beach
A pool area with a waterfall feature, lounge chairs, and palm trees.

7. Tropical Beach Resorts

Tropical Beach Resorts
3.5 star property
South Village
9.4 out of 10, Exceptional, (5,819 reviews)
"Great place to visit!"
United States
Margaret Lai Ling
The price is P6,938
P9,462 total
includes taxes & fees
Sep 2 - Sep 3
Tropical Beach Resorts

8. Gulf to Bay Island Oasis

Gulf to Bay Island Oasis
2.0 star property
Bradenton Beach
The price is P11,772
P36,541 total
includes taxes & fees
Sep 8 - Sep 9
Gulf to Bay Island Oasis

9. DOLPHIN PRIVATE HOUSE

DOLPHIN PRIVATE HOUSE
3.0 star property
Siesta Key Village
The price is P33,060
P37,358 total
includes taxes & fees
Sep 2 - Sep 3
DOLPHIN PRIVATE HOUSE
A modern living room with a flat-screen TV on a wooden cabinet, a grey sofa with patterned cushions, and a large window with sheer curtains.

10. SeaSpray Resort

SeaSpray Resort
4.0 star property
Siesta Key
9.6 out of 10, Exceptional, (175 reviews)
"Beautiful hotel comfortable bed nice and friendly staff!!!!"
United States
Isabel
The price is P12,832
P14,501 total
includes taxes & fees
Sep 2 - Sep 3
SeaSpray Resort
A modern bedroom with a large bed, a TV mounted on the wall, a wooden headboard, and a view of the sea through the balcony.

11. Seabreeze at Anna Maria Island Inn

Seabreeze at Anna Maria Island Inn
3.0 star property
Bradenton Beach
8.8 out of 10, Excellent, (128 reviews)
"Right on beach, in a good area. Comfy beds, would stay here again"
United States
Katelyn
The price is P13,413
P16,975 total
includes taxes & fees
Sep 8 - Sep 9
Seabreeze at Anna Maria Island Inn
A compact living space with a kitchen, a dining area, and a sofa with cushions.

12. Tiny House Siesta

Tiny House Siesta
2.0 star property
Sarasota
8.4 out of 10, Very Good, (384 reviews)
"Great place"
United States
Mario
The price is P5,248
P14,377 total
includes taxes & fees
Sep 19 - Sep 20
Tiny House Siesta
A modern kitchen with white cabinetry, a central island, pendant lighting, and a dining area with a white sofa and table.

13. 3716 7th Ave W

3716 7th Ave W
3.0 star property
Bradenton
The price is P146,941
P192,119 total
includes taxes & fees
Sep 3 - Sep 4
3716 7th Ave W

14. Sun Outdoors Sarasota

Sun Outdoors Sarasota
2.5 star property
Fordville
The price is P28,018
P31,661 total
includes taxes & fees
Sep 14 - Sep 15
Sun Outdoors Sarasota
A beach scene with waves gently lapping at the shore and the sun setting in the distance.

15. 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 P8,737
P41,229 total
includes taxes & fees
Sep 7 - Sep 8
Palm Tree Villas
A modern kitchen with a stainless steel refrigerator, granite countertops, wooden cabinets, and two bar stools.

16. Explore Sarasota: Condo w/ Pool Access, Near Dtwn

Explore Sarasota: Condo w/ Pool Access, Near Dtwn
3.5 star property
Sarasota
The price is P5,915
P17,873 total
includes taxes & fees
Sep 14 - Sep 15
Explore Sarasota: Condo w/ Pool Access, Near Dtwn
An outdoor deck with tables and chairs, a striped umbrella, and a view of the beach.

17. Alamanda Villas

Alamanda Villas
3.5 star property
Holmes Beach
8.4 out of 10, Very Good, (11 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 P14,445
P28,870 total
includes taxes & fees
Sep 17 - Sep 18
Alamanda Villas

18. Pineapple Paradise 1 13 min to Beach Fire Pit

Pineapple Paradise 1 13 min to Beach Fire Pit
2.0 star property
Central Sarasota
Pineapple Paradise 1 13 min to Beach Fire Pit
A covered outdoor bar area with seating, a pool, and a view of the outdoors.

19. 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, (1,180 reviews)
"Great place to stay"
United States
Michael
The price is P12,095
P16,481 total
includes taxes & fees
Sep 2 - Sep 3
Beach House Suites by the Don CeSar
An aerial view of a coastal city with a long sandy beach, numerous hotels, and clear blue waters.

20. Lulu's Key House Green 1/1 Upstairs

Lulu's Key House Green 1/1 Upstairs
3.5 star property
Siesta Key Village
Lulu's Key House Green 1/1 Upstairs
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

Zota Beach Resort

Zota Beach Resort

8/10 Good
"Everything was great but would rather skip the valet parking. Would rather park and secure my own auto."
Anthony 1-night trip
Posted 10 hours ago
Zota Beach Resort

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:

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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 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?

Longboat Key Beaches and Jewfish Key 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.