Longboat Key Vacation Rentals

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Check prices for these dates

In two weeks
Sep 12 - Sep 14
In one month
Sep 26 - Sep 28
In two months
Oct 24 - Oct 26
In three months
Nov 21 - Nov 23

Vacation Rentals in Longboat Key

Our top choices for Longboat Key vacation rentals

Sea Club I Beach Resort
On the beach, white sand

Sea Club I Beach Resort

3.0 star property
9.0 out of 10, Wonderful, (320)
"just an amazing staff and clean rooms! it was paradise will go back next year for sure!!"
Sea Club I Beach Resort
Flash Sale Late Sept-early Oct Take a Peek 1fabulous unit.
Property grounds

Flash Sale Late Sept-early Oct Take a Peek 1fabulous unit.

10.0 out of 10, Exceptional, (124)
"You can not get any closer to the beach than this. The view, the room and our property manager were all amazing. ZERO complaints. Can't wait to go back. "
The price is ￥29,062
￥67,853 total
includes taxes & fees
Sep 1 - Sep 2
Flash Sale Late Sept-early Oct Take a Peek 1fabulous unit.
THE BEACH #107 Summer special 210 nite+fees Beachfront Full View
On the beach, sun loungers, beach towels

THE BEACH #107 Summer special 210 nite+fees Beachfront Full View

10.0 out of 10, Exceptional, (73)
"Our second time here and it was wonderful again. Annette is very sweet and the place is perfect!"
The price is ￥30,927
￥58,555 total
includes taxes & fees
Sep 25 - Sep 26
THE BEACH #107 Summer special 210 nite+fees Beachfront Full View
Beach front 2 bed-2 bath private balcony, modern with Gulf front views
On the beach

Beach front 2 bed-2 bath private balcony, modern with Gulf front views

8.8 out of 10, Excellent, (25)
"Great view and nice place for a short stay. "
The price is ￥35,388
￥68,483 total
includes taxes & fees
Sep 1 - Sep 2
Beach front 2 bed-2 bath private balcony, modern with Gulf front views
Longboat Key beach house - 5 min walk to the beaches and top local restaurants
Sun loungers, beach towels

Longboat Key beach house - 5 min walk to the beaches and top local restaurants

9.4 out of 10, Exceptional, (28)
"What a beautiful propertyNicely decorated. Very convenient with 4 bedrooms all in one floor The peacocks are a nice touch. Access to the beach is very close with parking. The whole area is beautifulHighly recommended "
Longboat Key beach house - 5 min walk to the beaches and top local restaurants
Charming 1-bedroom, beachfront condo in marvelous Longboat Key
Outdoor dining

Charming 1-bedroom, beachfront condo in marvelous Longboat Key

9.0 out of 10, Wonderful, (17)
"The property was great for our family, loved having a pool and beach access. Super simple especially with a toddler in tow."
The price is ￥35,388
￥63,875 total
includes taxes & fees
Sep 1 - Sep 2
Charming 1-bedroom, beachfront condo in marvelous Longboat Key
GULF FRONT CONDO / PRIVATE PATIO / STEPS TO THE BEACH
On the beach

GULF FRONT CONDO / PRIVATE PATIO / STEPS TO THE BEACH

9.8 out of 10, Exceptional, (103)
"Very good location excellent apartament "
GULF FRONT CONDO / PRIVATE PATIO / STEPS TO THE BEACH
Charming 1-bedroom, beachfront condo in serene Longboat Key with WiFi, AC
On the beach

Charming 1-bedroom, beachfront condo in serene Longboat Key with WiFi, AC

6.6 out of 10, (7)
"Great location and beach access- pool is awesome! Unit doesn’t face the ocean, but it’s right there! Very low key- place is very clean. WiFi is spotty and would not be good if you are planning to work while staying- that is an island wide issue I believe- No stove, but has everything else a kitchen needs and a grill- we would come back! "
The price is ￥41,286
￥67,650 total
includes taxes & fees
Sep 10 - Sep 11
Charming 1-bedroom, beachfront condo in serene Longboat Key with WiFi, AC
Breathtaking Beach Front Property Ground Floor Condo
On the beach

Breathtaking Beach Front Property Ground Floor Condo

9.6 out of 10, Exceptional, (146)
"Fantastic beach and accommodations. Everyone we met were so nice and friendly. Best sunsets on the gulf!!!"
Breathtaking Beach Front Property Ground Floor Condo
Longboat Bay Club
Outdoor pool

Longboat Bay Club

3.5 star property
10.0 out of 10, Exceptional, (1)
"Great property with beach access across the street! 2 br unit was huge as were the balconies. Our unit 105 was quite dated but still nice."
Longboat Bay Club
Flash sale Sept 2-4/ 7-13, 5-floor penthouse 60 feet from water, 150+ reviews
Property grounds

Flash sale Sept 2-4/ 7-13, 5-floor penthouse 60 feet from water, 150+ reviews

10.0 out of 10, Exceptional, (194)
"Very relaxing "
The price is ￥33,044
￥72,942 total
includes taxes & fees
Sep 2 - Sep 3
Flash sale Sept 2-4/ 7-13, 5-floor penthouse 60 feet from water, 150+ reviews
Country Club Long Boat Key Beach Villa 2B 3BA Pool No Hurricane Damage
Outdoor dining

Country Club Long Boat Key Beach Villa 2B 3BA Pool No Hurricane Damage

9.8 out of 10, Exceptional, (88)
"Very nice townhouse with excellent amenities. Located near great restaurants and beaches. Would definitely stay there again."
Country Club Long Boat Key Beach Villa 2B 3BA Pool No Hurricane Damage
Charming Cabana Beach Club #8 - Your Coastal retreat Awaits!#9 also available.
On the beach, sun loungers, beach towels

Charming Cabana Beach Club #8 - Your Coastal retreat Awaits!#9 also available.

9.8 out of 10, Exceptional, (152)
"Our stay was perfect! Everything we needed was in the unit and the communication with the owner was great. Can't wait to visit again soon."
Charming Cabana Beach Club #8 - Your Coastal retreat Awaits!#9 also available.
Sunset and Beach view unit 402
On the beach

Sunset and Beach view unit 402

10.0 out of 10, Exceptional, (4)
"Clean condo. Beautiful view of Gulf"
Sunset and Beach view unit 402
Longboat Key bliss. A perfect Retreat at Cabana Beach Club #9.Also available#8
On the beach, sun loungers, beach towels

Longboat Key bliss. A perfect Retreat at Cabana Beach Club #9.Also available#8

9.4 out of 10, Exceptional, (120)
"We were in town for a wedding and this spot was conveniently located and had great pool and beach access. "
Longboat Key bliss. A perfect Retreat at Cabana Beach Club #9.Also available#8
Charming Longboat Key Bungalow with beach access minutes away…
Sun loungers

Charming Longboat Key Bungalow with beach access minutes away…

2.0 star property
9.4 out of 10, Exceptional, (12)
"Very cute place. It was in a great spot for easy access to the beach and restaurants. "
The price is ￥19,773
￥58,804 total
includes taxes & fees
Sep 1 - Sep 2
Charming Longboat Key Bungalow with beach access minutes away…
LaPlaya 102B-Directly on the beach with the warm Gulf waters waiting!
On the beach, beach towels

LaPlaya 102B-Directly on the beach with the warm Gulf waters waiting!

9.8 out of 10, Exceptional, (8)
"We had a great time at La Playa. The beach is beautiful. The condo is nice, well stocked and quiet. Will definitely stay there again. Maybe next February."
LaPlaya 102B-Directly on the beach with the warm Gulf waters waiting!
Unforgettable Oceanfront Oasis-The Beach on Longboat Key #226 by RVA
A heated pool

Unforgettable Oceanfront Oasis-The Beach on Longboat Key #226 by RVA

9.2 out of 10, Wonderful, (118)
"Couldn't have been a better spot for our family"
Unforgettable Oceanfront Oasis-The Beach on Longboat Key #226 by RVA
Charming Beach Front Studio Steps to the Sand and Gulf
On the beach, sun loungers

Charming Beach Front Studio Steps to the Sand and Gulf

9.8 out of 10, Exceptional, (18)
"Loved everything about our stay. Will definitely be back!"
Charming Beach Front Studio Steps to the Sand and Gulf
Direct Gulf Views! Spacious 2BR Beachfront Condo Cabana Beach Club #7 by RVA
On the beach

Direct Gulf Views! Spacious 2BR Beachfront Condo Cabana Beach Club #7 by RVA

9.6 out of 10, Exceptional, (68)
"Fantastic location at beach front."
Direct Gulf Views! Spacious 2BR Beachfront Condo Cabana Beach Club #7 by RVA
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

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 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 171 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.