Longboat Key Vacation Rentals

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Our top choices for Longboat Key vacation rentals

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.
$339 nightly
The price is $373
Jan 11 - Jan 12, 2026
Total with taxes and fees
Renovated Beach Paradise. Ground Floor unit 64

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.
$411 nightly
The price is $458
Jan 4 - Jan 5, 2026
Total with taxes and fees
Ground Floor Oceanview: Lots of January Availability!

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.
$403 nightly
The price is $450
Dec 31 - Jan 1, 2026
Total with taxes and fees
Charming Longboat Key Bungalow with beach access minutes away…

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.
$377 nightly
The price is $415
Jan 30 - Jan 31, 2026
Total with taxes and fees
Sunset and Beach view unit 402

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.
$376 nightly
The price is $419
Jan 2 - Jan 3, 2026
Total with taxes and fees
Gulfside Getaway – Silver Sands Resort #235 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.
$240 nightly
The price is $268
Jan 9 - Jan 10, 2026
Total with taxes and fees
Beachfront Studio – Cabana #5B 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
$426 nightly
The price is $475
Jan 23 - Jan 24, 2026
Total with taxes and fees
2BR Gulfside Paradise – Longboat Key by RVA

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.
$346 nightly
The price is $386
Jan 4 - Jan 5, 2026
Total with taxes and fees
THE BEACH CONDO #107 BEACHFRONT FULL VIEW

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.
$486 nightly
The price is $541
Jan 12 - Jan 13, 2026
Total with taxes and fees
Beach front 2 bed-2 bath private balcony, modern with Gulf front views

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, (85)
"The perfect beach cottage for our wedding anniversary. We had everything we needed including beautiful weather ."
United States
Julie Q.
$371 nightly
The price is $415
Jan 3 - Jan 4, 2026
Total with taxes and fees
One-Bedroom Beach Condo on Longboat Key: January Availability!

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.
$906 nightly
The price is $1,013
Jan 3 - Jan 4, 2026
Total with taxes and fees
Updated Beachfront Condo at Prestigious Long Boat Key Resort

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.
$367 nightly
The price is $405
Jan 23 - Jan 24, 2026
Total with taxes and fees
Best views of the beach from your balcony Unit 301

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.
$1,021 nightly
The price is $1,139
Jan 12 - Jan 13, 2026
Total with taxes and fees
3-bedroom, 3 bath condo in beautiful Longboat Key. Beachfront views w/ pool.

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
$411 nightly
The price is $458
Jan 4 - Jan 5, 2026
Total with taxes and fees
Direct Oceanview on LBK: Lots of January Availability!

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
$449 nightly
The price is $500
Jan 12 - Jan 13, 2026
Total with taxes and fees
Steps to Beach – Silver Sands 2BR Condo #243S by RVA

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.
$282 nightly
The price is $314
Dec 31 - Jan 1, 2026
Total with taxes and fees
Beachside Studio – Silver Sands #253A, Longboat Key

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.
$293 nightly
The price is $328
Jan 23 - Jan 24, 2026
Total with taxes and fees
Newly Renovated 1BR – Cabana Beach #5 RVA

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.
$303 nightly
The price is $336
Jan 8 - Jan 9, 2026
Total with taxes and fees
Right on the beach.Renovated ground Floor unit 63.

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.
$355 nightly
The price is $396
Jan 1 - Jan 2, 2026
Total with taxes and fees
Beachfront Bliss on Longboat Key- Steps to the sand

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
$313 nightly
The price is $350
Jan 11 - Jan 12, 2026
Total with taxes and fees
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

Price trends for vacation rentals in Longboat Key

Less expensive
More expensive
Next month
December
March
$344
Month
Price
January
$344
February
$431
March
$555
April
$440
May
$426
June
$485
July
$477
August
$412
September
$348
October
$348
November
$357
December
$327
Price trend information excludes taxes and fees and is based on base rates for a nightly stay for 2 adults found in the last 7 days on our site and averaged for commonly viewed vacation rentals in Longboat Key. Select dates and complete search for nightly totals inclusive of taxes and fees.

Find out more about Longboat Key

Everything you need to know about Longboat Key vacation rentals

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

Longboat Key vacation 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 low season months. For more hustle and bustle, you may prefer to visit Longboat Key in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $297 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Longboat Key rentals

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

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 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.