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

Longboat Key Vacation Rentals

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Aug 28 - Aug 30
In two months
Oct 9 - Oct 11
In three months
Nov 6 - Nov 8
In four months
Dec 4 - Dec 6

Our top choices for Longboat Key vacation rentals

On the beach, sun loungers, beach towels

1. Vitamin Sea: Open August 17th & 18th!

Vitamin Sea: Open August 17th & 18th!
Longboat Key
10.0 out of 10, Exceptional, (96 reviews)
"Absolutely loved our stay in LBK. Heidi is a wonderful communicative host and made our vacation perfect. We definitely will be returning next year ! "
United States
Jessica L.
$330 nightly
The price is $368
Aug 29 - Aug 30
Total with taxes and fees
Vitamin Sea: Open August 17th & 18th!
On the beach, beach umbrellas

2. Relax at Gulf – Silver Sands Resort #232, Longboat

Relax at Gulf – Silver Sands Resort #232, Longboat
Longboat Key
9.4 out of 10, Exceptional, (82 reviews)
"Very happy with my stay. Room was very clean, beautifully decorated and very comfortable. Perfect efficiency! Highly recommend"
United States
Gloria
$321 nightly
The price is $357
Aug 13 - Aug 14
Total with taxes and fees
Relax at Gulf – Silver Sands Resort #232, Longboat
On the beach, beach umbrellas

3. Affordable Beach Studio – Silver Sands #257A by RVA

Affordable Beach Studio – Silver Sands #257A by RVA
Longboat Key
9.6 out of 10, Exceptional, (82 reviews)
"Lovely hotel right on the Gulf. Steps directly to the beach. Beautiful sunsets."
United States
SUSAN C.
$293 nightly
The price is $327
Aug 13 - Aug 14
Total with taxes and fees
Affordable Beach Studio – Silver Sands #257A by RVA
On the beach

4. Beachfront Studio – Cabana #5B by RVA

Beachfront Studio – Cabana #5B by RVA
Longboat Key
8.2 out of 10, Very Good, (82 reviews)
"The cabana was a fantastic place to escape. It had easy access to both the beach and the pool. My kids loved every moment there."
United States
Roxana P.
$281 nightly
The price is $312
Aug 11 - Aug 12
Total with taxes and fees
Beachfront Studio – Cabana #5B by RVA
On the beach, beach umbrellas

5. Silver Sands Serenity – Unit 234 by RVA

Silver Sands Serenity – Unit 234 by RVA
Longboat Key
9.4 out of 10, Exceptional, (32 reviews)
" Great location, office staff are very pleasant, room was very spacious with everything you need"
United States
GLENNA M.
$273 nightly
The price is $304
Aug 13 - Aug 14
Total with taxes and fees
Silver Sands Serenity – Unit 234 by RVA
On the beach, beach umbrellas

6. Gulfside Resort – Silver Sands #241A by RVA

Gulfside Resort – Silver Sands #241A by RVA
Longboat Key
8.4 out of 10, Very Good, (51 reviews)
"Beach is beautiful, location is great. Room was clean. Rhe bed"
United States
Kellie B.
$311 nightly
The price is $347
Aug 11 - Aug 12
Total with taxes and fees
Gulfside Resort – Silver Sands #241A by RVA
Beach nearby

7. Beach Castle Bliss #22 by RVA

Beach Castle Bliss #22 by RVA
Longboat Key
9.6 out of 10, Exceptional, (48 reviews)
"The walks to the bay and Gulf were shorter than we anticipated (bonus: a couple of restaurants are a short walk away, too). Sunrise over the bay just a few steps from our unit, and sunsets over the Gulf just across the street. The unit itself was clean, comfortable, with plenty of space. And the pool area is very well maintained. Overall, it's exactly what we wanted from our Longboat Key getaway."
United States
Robert S.
$324 nightly
The price is $361
Aug 11 - Aug 12
Total with taxes and fees
Beach Castle Bliss #22 by RVA
On the beach, beach umbrellas

8. 1BR Beach Getaway – Silver Sands #254 by RVA

1BR Beach Getaway – Silver Sands #254 by RVA
Longboat Key
9.2 out of 10, Wonderful, (98 reviews)
"Great view, clean, beautiful!"
United States
Bethany
$338 nightly
The price is $376
Aug 11 - Aug 12
Total with taxes and fees
1BR Beach Getaway – Silver Sands #254 by RVA
Beach nearby

9. Seaside Escape – Beach Castle #24 by RVA

Seaside Escape – Beach Castle #24 by RVA
Longboat Key
9.2 out of 10, Wonderful, (51 reviews)
"Condo was clean, nicely decorated, comfy king bed and the property was charming and quiet.Appreciated the back deck and view of the bay.Also convenient to many restaurants and the beach.Also loved access to the club down the street."
United States
Jody B.
$302 nightly
The price is $336
Aug 11 - Aug 12
Total with taxes and fees
Seaside Escape – Beach Castle #24 by RVA
On the beach, beach umbrellas

10. Sun, Sand & Silver Sands – Gulfside Resort #237 by RVA

Sun, Sand & Silver Sands – Gulfside Resort #237 by RVA
Longboat Key
8.8 out of 10, Excellent, (44 reviews)
"Enjoyed our stay"
United States
Susan C.
$315 nightly
The price is $351
Aug 11 - Aug 12
Total with taxes and fees
Sun, Sand & Silver Sands – Gulfside Resort #237 by RVA
On the beach, beach umbrellas

11. Silver Sands #245A Resort by RVA

Silver Sands #245A Resort by RVA
Longboat Key
8.6 out of 10, Excellent, (63 reviews)
"Liked"
United States
jacquelynn b.
$303 nightly
The price is $337
Aug 23 - Aug 24
Total with taxes and fees
Silver Sands #245A Resort by RVA
On the beach, beach umbrellas

12. Starfish Studio Silver Sands #247A – Studio/1BA Resort in LBK

Starfish Studio Silver Sands #247A – Studio/1BA Resort in LBK
Longboat Key
8.0 out of 10, Very Good, (9 reviews)
"Nice place, clean, conveniently located, right on the beach, very helpful/friendly manager. We didn’t use the pool but it was clean and well taken care of, also heated. Beach was awesome, soft clean sand, clear water. Would like to stay here again."
United States
William
$302 nightly
The price is $336
Aug 16 - Aug 17
Total with taxes and fees
Starfish Studio Silver Sands #247A – Studio/1BA Resort in LBK
On the beach, beach umbrellas

13. Oceanfront 1BR – Silver Sands #257 by RVA

Oceanfront 1BR – Silver Sands #257 by RVA
Longboat Key
8.8 out of 10, Excellent, (53 reviews)
"Blown away at location and amenities! Spent 20 yrs renting on AMI, no more......this is what AMI used to be. Laid back, family oriented. Brittany checked us in and was soo very friendly. Room was great, rented for myself, spouse, and 2 adult children and we had plenty of room. Only thing that was disconcerting was the adjoining room.......we heard EVERYTHING coming from under the door which connects to the bedrooms. We will book again, but stuff towels under that door to help with the noise. "
United States
Kelly
$358 nightly
The price is $399
Aug 11 - Aug 12
Total with taxes and fees
Oceanfront 1BR – Silver Sands #257 by RVA
On the beach

14. Oceanfront Oasis – Longboat Key 226 by RVA

Oceanfront Oasis – Longboat Key 226 by RVA
Longboat Key
9.4 out of 10, Exceptional, (136 reviews)
"Great beach!"
United States
Carolyn
$288 nightly
The price is $321
Aug 11 - Aug 12
Total with taxes and fees
Oceanfront Oasis – Longboat Key 226 by RVA
On the beach, beach umbrellas

15. Coastal Comfort – Silver Sands Resort #233 by RVA

Coastal Comfort – Silver Sands Resort #233 by RVA
Longboat Key
8.8 out of 10, Excellent, (34 reviews)
"3rd time here already booked another trip. So easy! Love it here!"
United States
Emily
$293 nightly
The price is $327
Aug 16 - Aug 17
Total with taxes and fees
Coastal Comfort – Silver Sands Resort #233 by RVA
On the beach

16. Oceanfront Bliss–Longboat Key Beach 106 by RVA

Oceanfront Bliss–Longboat Key Beach 106 by RVA
Longboat Key
8.8 out of 10, Excellent, (107 reviews)
"Great location"
United States
Amy R.
$273 nightly
The price is $304
Aug 13 - Aug 14
Total with taxes and fees
Oceanfront Bliss–Longboat Key Beach 106 by RVA
On the beach, beach umbrellas

17. 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, (64 reviews)
"We had the most wonderful stay despite the cold temps for most it! The staff at our location are above and beyond to make sure you have everything you need! Highly recommend!"
United States
Sahra S.
$305 nightly
The price is $340
Aug 16 - Aug 17
Total with taxes and fees
Ground Floor, Steps to Sand – Silver Sands #243A by RVA
Beach nearby

18. 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, (93 reviews)
"Everything was great "
United States
kirt v.
$360 nightly
The price is $395
Aug 23 - Aug 24
Total with taxes and fees
Best views of the beach from your balcony Unit 301
Beach nearby

19. Gulf Getaway – Beach Castle #12 by RVA

Gulf Getaway – Beach Castle #12 by RVA
Longboat Key
9.6 out of 10, Exceptional, (43 reviews)
"Enjoyed the condo and area. Well equipped and relaxing. "
United States
Robert P.
$358 nightly
The price is $399
Aug 12 - Aug 13
Total with taxes and fees
Gulf Getaway – Beach Castle #12 by RVA
On the beach

20. Newly Renovated 1BR – Cabana Beach #5 RVA

Newly Renovated 1BR – Cabana Beach #5 RVA
Longboat Key
8.8 out of 10, Excellent, (75 reviews)
"The view and beach access was amazing. Loved our stay. "
United States
Julie F.
$322 nightly
The price is $359
Aug 11 - Aug 12
Total with taxes and fees
Newly Renovated 1BR – Cabana Beach #5 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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Longboat Key Hotel Reviews

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

10/10 Excellent
"Enjoyed our oceanfront room. The view was amazing and the beach was beautiful. Would book again"
Mark P. 2-night trip
Posted 15 hours ago
Are you ready for a luxury 5-floor penthouse 60 ft from water, 207 reviews

Price trends for vacation rentals in Longboat Key

Less expensive
More expensive
This month
Next month
October
February
$384
$374
Month
Price
January
$430
February
$539
March
$484
April
$441
May
$409
June
$463
July
$458
August
$384
September
$374
October
$371
November
$394
December
$429
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 $304 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.

Explore a world of travel with Expedia

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 20 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.