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Longboat Key Vacation Rentals

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Check prices for these dates

In two weeks
Jan 16 - Jan 18
In two months
Feb 27 - Mar 1
In three months
Mar 27 - Mar 29
In four months
Apr 24 - Apr 26

Our top choices for Longboat Key vacation rentals

Beach nearby
Renovated Beach Paradise. Ground Floor unit 64

Renovated Beach Paradise. Ground Floor unit 64

Renovated Beach Paradise. Ground Floor unit 64
Longboat Key
10.0 out of 10, Exceptional, (61)
"Beach is beautiful and condo is convient to all. Condo is very comfortable and as shown and described. We will definitely stay again."
United States
Kim S.
The price is ￥23,486
￥58,526 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Renovated Beach Paradise. Ground Floor unit 64
On the beach, sun loungers, beach towels
Ground Floor Oceanview: Lots of January Availability!

Ground Floor Oceanview: Lots of January Availability!

Ground Floor Oceanview: Lots of January Availability!
2.0 star property
Longboat Key
9.6 out of 10, Exceptional, (10)
" Lovely unit right on the beach. Well stocked and so tastefully decorated. Very quiet area of Longboat Key. Will most definitely go back. "
United States
Joe M.
The price is ￥40,160
￥71,732 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Ground Floor Oceanview: Lots of January Availability!
Sun loungers
Charming Longboat Key Bungalow with beach access minutes away…

Charming Longboat Key Bungalow with beach access minutes away…

Charming Longboat Key Bungalow with beach access minutes away…
2.0 star property
Longboat Key
9.4 out of 10, Exceptional, (12)
"Enjoyed our stay in this quiet little place with close access to restaurants and just a few minutes from Bradenton. Would come back!"
United States
Todd B.
The price is ￥27,901
￥70,399 total
includes taxes & fees
Dec 31 - Jan 1, 2026
Charming Longboat Key Bungalow with beach access minutes away…
Beach nearby
Sunset and Beach view unit 402

Sunset and Beach view unit 402

Sunset and Beach view unit 402
Longboat Key
9.8 out of 10, Exceptional, (14)
"Accommodation were outstanding with beautiful views of the gulf!"
United States
Mike C.
Sunset and Beach view unit 402
On the beach, beach umbrellas
Gulfside Getaway – Silver Sands Resort #235 by RVA

Gulfside Getaway – Silver Sands Resort #235 by RVA

Gulfside Getaway – Silver Sands Resort #235 by RVA
Longboat Key
8.8 out of 10, Excellent, (30)
"Very relaxing"
United States
Susan D.
The price is ￥28,496
￥69,329 total
includes taxes & fees
Jan 2 - Jan 3, 2026
Gulfside Getaway – Silver Sands Resort #235 by RVA
Dining
Beachfront Studio – Cabana #5B by RVA

Beachfront Studio – Cabana #5B by RVA

Beachfront Studio – Cabana #5B by RVA
Longboat Key
8.2 out of 10, Very Good, (73)
"Very nice place, clean and quiet. Staff very accommodating and professional. Definitely 5 star. "
United States
K M.
Beachfront Studio – Cabana #5B by RVA
On the beach
2BR Gulfside Paradise – Longboat Key by RVA

2BR Gulfside Paradise – Longboat Key by RVA

2BR Gulfside Paradise – Longboat Key by RVA
Longboat Key
9.8 out of 10, Exceptional, (74)
"Very clean "
United States
Lana
2BR Gulfside Paradise – Longboat Key by RVA
On the beach, sun loungers, beach towels
THE BEACH CONDO #107 BEACHFRONT FULL VIEW

THE BEACH CONDO #107 BEACHFRONT FULL VIEW

THE BEACH CONDO #107 BEACHFRONT FULL VIEW
Longboat Key
10.0 out of 10, Exceptional, (81)
"Beautiful location and the beach is amazing "
United States
Heather A.
The price is ￥31,157
￥60,932 total
includes taxes & fees
Jan 5 - Jan 6, 2026
THE BEACH CONDO #107 BEACHFRONT FULL VIEW
On the beach
Beach front 2 bed-2 bath private balcony, modern with Gulf front views

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

Beach front 2 bed-2 bath private balcony, modern with Gulf front views
Longboat Key
9.0 out of 10, Wonderful, (34)
"Great stay and very friendly staff and host."
United States
Ida A.
Beach front 2 bed-2 bath private balcony, modern with Gulf front views
On the beach, sun loungers, beach towels
One-Bedroom Beach Condo on Longboat Key: January Availability!

One-Bedroom Beach Condo on Longboat Key: January Availability!

One-Bedroom Beach Condo on Longboat Key: January Availability!
Longboat Key
10.0 out of 10, Exceptional, (84)
"The perfect beach cottage for our wedding anniversary. We had everything we needed including beautiful weather ."
United States
Julie Q.
The price is ￥35,228
￥64,906 total
includes taxes & fees
Jan 3 - Jan 4, 2026
One-Bedroom Beach Condo on Longboat Key: January Availability!
A heated pool
Updated Beachfront Condo at Prestigious Long Boat Key Resort

Updated Beachfront Condo at Prestigious Long Boat Key Resort

Updated Beachfront Condo at Prestigious Long Boat Key Resort
Longboat Key
8.4 out of 10, Very Good, (15)
"Perfect view, super clean, convenient, was the perfect size for me and my husband. We stayed for our 10 year anniversary and everything was perfect. "
United States
HALEY B.
The price is ￥80,634
￥164,086 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Updated Beachfront Condo at Prestigious Long Boat Key Resort
Smart TV, offices
Best views of the beach from your balcony Unit 301

Best views of the beach from your balcony Unit 301

Best views of the beach from your balcony Unit 301
Longboat Key
9.8 out of 10, Exceptional, (88)
"It was so great loved everything in the home"
United States
TERRY C.
The price is ￥28,965
￥63,465 total
includes taxes & fees
Jan 23 - Jan 24, 2026
Best views of the beach from your balcony Unit 301
On the beach
3-bedroom, 3 bath condo in beautiful Longboat Key. Beachfront views w/ pool.

3-bedroom, 3 bath condo in beautiful Longboat Key. Beachfront views w/ pool.

3-bedroom, 3 bath condo in beautiful Longboat Key. Beachfront views w/ pool.
Longboat Key
10.0 out of 10, Exceptional, (2)
"Great stay. Everything we needed. Communication with host was outstanding ! Perfect !!"
United States
Joe A.
3-bedroom, 3 bath condo in beautiful Longboat Key. Beachfront views w/ pool.
Outdoor dining
Direct Oceanview on LBK: Lots of January Availability!

Direct Oceanview on LBK: Lots of January Availability!

Direct Oceanview on LBK: Lots of January Availability!
Longboat Key
10.0 out of 10, Exceptional, (116)
"Great hostess, very thoughtful and kind. She thought of everything, we didn’t have to leave the premises. The location is unbelievable and the condo is gorgeous. We will definitely stay again!!"
United States
Amy K
The price is ￥40,160
￥71,732 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Direct Oceanview on LBK: Lots of January Availability!
Fridge, microwave, oven, stovetop
Steps to Beach – Silver Sands 2BR Condo #243S by RVA

Steps to Beach – Silver Sands 2BR Condo #243S by RVA

Steps to Beach – Silver Sands 2BR Condo #243S by RVA
Longboat Key
9.2 out of 10, Wonderful, (31)
"Extremely convenient access to beach, Large pool, putting green, and pool toys made our stay very fun. "
United States
Maria
The price is ￥38,673
￥82,929 total
includes taxes & fees
Jan 12 - Jan 13, 2026
Steps to Beach – Silver Sands 2BR Condo #243S by RVA
On the beach, beach umbrellas
Beachside Studio – Silver Sands #253A, Longboat Key

Beachside Studio – Silver Sands #253A, Longboat Key

Beachside Studio – Silver Sands #253A, Longboat Key
Longboat Key
8.6 out of 10, Excellent, (36)
"I really enjoyed my stay at the Silver Sands and will recommend your property"
United States
Jeff H.
The price is ￥24,425
￥52,273 total
includes taxes & fees
Dec 31 - Jan 1, 2026
Beachside Studio – Silver Sands #253A, Longboat Key
On the beach
Newly Renovated 1BR – Cabana Beach #5 RVA

Newly Renovated 1BR – Cabana Beach #5 RVA

Newly Renovated 1BR – Cabana Beach #5 RVA
Longboat Key
8.8 out of 10, Excellent, (71)
"Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: The condo was clean and had all that we needed for our two night stay. Loved it will be back again... just a little walk to the beach and some he pool was very nice as well."
United States
Nancy C.
The price is ￥27,869
￥54,675 total
includes taxes & fees
Jan 23 - Jan 24, 2026
Newly Renovated 1BR – Cabana Beach #5 RVA
Beach nearby
Right on the beach.Renovated ground Floor unit 63.

Right on the beach.Renovated ground Floor unit 63.

Right on the beach.Renovated ground Floor unit 63.
Longboat Key
9.6 out of 10, Exceptional, (57)
"Excellent, clean, and friendly"
United States
John G.
The price is ￥23,486
￥52,686 total
includes taxes & fees
Jan 8 - Jan 9, 2026
Right on the beach.Renovated ground Floor unit 63.
Outdoor dining
Beachfront Bliss on Longboat Key- Steps to the sand

Beachfront Bliss on Longboat Key- Steps to the sand

Beachfront Bliss on Longboat Key- Steps to the sand
Longboat Key
7.0 out of 10, Good, (2)
"Location was perfect for the beach access we were looking for. The unit was small with a few minor glitches, but it was clean.The property and pool were well mantained and there were no issues with check-in."
United States
GLEN R.
The price is ￥33,819
￥62,954 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Beachfront Bliss on Longboat Key- Steps to the sand
Property grounds
The Beach on Longboat Key #227 Resort by RVA

The Beach on Longboat Key #227 Resort by RVA

The Beach on Longboat Key #227 Resort by RVA
Longboat Key
9.2 out of 10, Wonderful, (71)
"The area and condo was perfect. The property was clean and well maintained. Highly recommended!"
United States
Fidel
The price is ￥29,279
￥58,556 total
includes taxes & fees
Jan 11 - Jan 12, 2026
The Beach on Longboat Key #227 Resort 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

THE BEACH CONDO #107 BEACHFRONT FULL VIEW

THE BEACH CONDO #107 BEACHFRONT FULL VIEW

10/10 Excellent
"we loved that is is right in the beach. Amenities were adequate for our short stay and the apt was clean. We would stay here again for sure!"
Joy D. 5-night trip
Posted 10 days ago
THE BEACH CONDO #107 BEACHFRONT FULL VIEW

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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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 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 22 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 St. Armands Circle 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.