Longboat Key Vacation Rentals

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Our top choices for Longboat Key vacation rentals

Island Time!

Island Time!
Longboat Key
10.0 out of 10, Exceptional, (125 reviews)
"Great host! Amazing location. Loved the beach access and views! Highly recommended "
United States
Bonnie N.
$378 nightly
The price is $422
May 13 - May 14
Total with taxes and fees
Island Time!

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
9.2 out of 10, Wonderful, (44 reviews)
"Small 2 story property right on the beach! The condo was clean and nicely laid out with room for the 3 of us. You can't beat the direct beach access and the shelling was great!"
United States
Jody S.
$486 nightly
The price is $541
May 13 - May 14
Total with taxes and fees
Beach front 2 bed-2 bath private balcony, modern with Gulf front views

THE BEACH CONDO #107 BEACHFRONT FULL VIEW

THE BEACH CONDO #107 BEACHFRONT FULL VIEW
Longboat Key
9.8 out of 10, Exceptional, (89 reviews)
"Incredible place. Already booked again!! "
United States
Julie T.
$404 nightly
The price is $452
May 10 - May 11
Total with taxes and fees
THE BEACH CONDO #107 BEACHFRONT FULL VIEW

Are you ready for a luxury 5-floor penthouse 60 ft from water, 207 reviews

Are you ready for a luxury 5-floor penthouse 60 ft from water, 207 reviews
Longboat Key
10.0 out of 10, Exceptional, (207 reviews)
"Great location."
United States
Janet B.
$507 nightly
The price is $565
May 10 - May 11
Total with taxes and fees
Are you ready for a luxury 5-floor penthouse 60 ft from water, 207 reviews

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, (89 reviews)
"Everything was great "
United States
kirt v.
$377 nightly
The price is $415
May 29 - May 30
Total with taxes and fees
Best views of the beach from your balcony Unit 301

Drift & Dune – Longboat Beachfront #101 RVA

Drift & Dune – Longboat Beachfront #101 RVA
Longboat Key
8.6 out of 10, Excellent, (80 reviews)
"Check in and out was easy, the pool and condo were great, and the location was awesome!"
United States
Bailey B.
$323 nightly
The price is $361
May 13 - May 14
Total with taxes and fees
Drift & Dune – Longboat Beachfront #101 RVA

Silver Sands 1BR – Gulfside Comfort #255 by RVA

Silver Sands 1BR – Gulfside Comfort #255 by RVA
Longboat Key
9.0 out of 10, Wonderful, (87 reviews)
"Location #1. Clean #2"
United States
Eric C.
$340 nightly
The price is $379
May 12 - May 13
Total with taxes and fees
Silver Sands 1BR – Gulfside Comfort #255 by RVA

Client texted view crazy Last minute cancellation Apr 25 - May 16th on sale

Client texted view crazy Last minute cancellation Apr 25 - May 16th on sale
Longboat Key
10.0 out of 10, Exceptional, (101 reviews)
"Location and view was amazing "
United States
joseph l.
$510 nightly
The price is $568
May 12 - May 13
Total with taxes and fees
Client texted view crazy Last minute cancellation Apr 25 - May 16th on sale

Gulf Front Escape – Silver Sands #252 by RVA

Gulf Front Escape – Silver Sands #252 by RVA
Longboat Key
9.2 out of 10, Wonderful, (103 reviews)
"Staff was welcoming- place was clean and stay was great"
United States
Joseph S.
$346 nightly
The price is $385
May 11 - May 12
Total with taxes and fees
Gulf Front Escape – Silver Sands #252 by RVA

1BR Beach Getaway – Silver Sands #254 by RVA

1BR Beach Getaway – Silver Sands #254 by RVA
Longboat Key
9.2 out of 10, Wonderful, (95 reviews)
"Great view, clean, beautiful!"
United States
Bethany
$328 nightly
The price is $366
May 13 - May 14
Total with taxes and fees
1BR Beach Getaway – Silver Sands #254 by RVA

Beachfront Bliss on Longboat Key- Steps to the sand

Beachfront Bliss on Longboat Key- Steps to the sand
Longboat Key
8.6 out of 10, Excellent, (17 reviews)
"Great locale right on the beach "
United States
Carole
$372 nightly
The price is $414
May 10 - May 11
Total with taxes and fees
Beachfront Bliss on Longboat Key- Steps to the sand

Gulf Views – Silver Sands #250, Longboat Key by RVA

Gulf Views – Silver Sands #250, Longboat Key by RVA
Longboat Key
9.0 out of 10, Wonderful, (77 reviews)
"Beautiful beach, great views from the balcony, we had a great stay."
United States
Meghan P.
$374 nightly
The price is $417
May 11 - May 12
Total with taxes and fees
Gulf Views – Silver Sands #250, Longboat Key by RVA

Ground Floor, Steps to Sand – Silver Sands #243A by RVA

Ground Floor, Steps to Sand – Silver Sands #243A by RVA
Longboat Key
8.6 out of 10, Excellent, (62 reviews)
"Would def stay here again!"
United States
Tammie and David
$303 nightly
The price is $338
May 12 - May 13
Total with taxes and fees
Ground Floor, Steps to Sand – Silver Sands #243A by RVA

The Beach on Longboat Key #227 Resort by RVA

The Beach on Longboat Key #227 Resort by RVA
Longboat Key
9.0 out of 10, Wonderful, (80 reviews)
"Very nice place"
United States
Laurette C.
$332 nightly
The price is $371
May 13 - May 14
Total with taxes and fees
The Beach on Longboat Key #227 Resort by RVA

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, (19 reviews)
"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.
$795 nightly
The price is $886
May 9 - May 10
Total with taxes and fees
Updated Beachfront Condo at Prestigious Long Boat Key Resort

Relax at Gulf – Silver Sands Resort #232, Longboat

Relax at Gulf – Silver Sands Resort #232, Longboat
Longboat Key
9.2 out of 10, Wonderful, (79 reviews)
"Great beach access. Central location on the island. Not overcrowded. Ground floor unit was in good shape considering the hurricane in 2024.Bedroom could use blackout curtains (it gets bright in there in the AM) and the road noise was a bit loud."
United States
Mark G.
$316 nightly
The price is $353
May 10 - May 11
Total with taxes and fees
Relax at Gulf – Silver Sands Resort #232, Longboat

Beachfront Studio – Cabana #5B by RVA

Beachfront Studio – Cabana #5B by RVA
Longboat Key
8.2 out of 10, Very Good, (77 reviews)
"The pool was disgusting, dirt and debris on the bottom and top so that was disappointing, while watching TV and sleeping a person actually opened up our porch door then the main door and just walked in and said they had booked the same room and had keys, what kind of place does not keep track of that and I'm not sure what the person was thinking the TV was on and it was up a little so I know they heard it from the outside but to get back to that place for allowing that to happen. He's lucky I...
United States
Joseph
$273 nightly
The price is $305
May 13 - May 14
Total with taxes and fees
Beachfront Studio – Cabana #5B by RVA

Newly Renovated 1BR – Cabana Beach #5 RVA

Newly Renovated 1BR – Cabana Beach #5 RVA
Longboat Key
8.8 out of 10, Excellent, (74 reviews)
"The view and beach access was amazing. Loved our stay. "
United States
Julie F.
$327 nightly
The price is $364
May 15 - May 16
Total with taxes and fees
Newly Renovated 1BR – Cabana Beach #5 RVA

Affordable Beach Studio – Silver Sands #257A by RVA

Affordable Beach Studio – Silver Sands #257A by RVA
Longboat Key
9.6 out of 10, Exceptional, (77 reviews)
"Right on beach-perfect for a short stay"
United States
Sean P.
$290 nightly
The price is $323
May 12 - May 13
Total with taxes and fees
Affordable Beach Studio – Silver Sands #257A by RVA

Gulfside Resort – Silver Sands #241A by RVA

Gulfside Resort – Silver Sands #241A by RVA
Longboat Key
8.4 out of 10, Very Good, (49 reviews)
"We enjoyed this fun spot with private beach, pool, and more!"
United States
Willow C.
$303 nightly
The price is $338
May 13 - May 14
Total with taxes and fees
Gulfside Resort – Silver Sands #241A 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
This month
Next month
September
March
$385
$476
Month
Price
January
$426
February
$440
March
$510
April
$408
May
$385
June
$476
July
$463
August
$391
September
$368
October
$373
November
$380
December
$414
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 $344 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 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.