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

Longboat Key Vacation Rentals

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Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Longboat Key vacation rentals

On the beach, beach umbrellas

1. Poolside Peace – Silver Sands Resort #242 by RVA

Poolside Peace – Silver Sands Resort #242 by RVA
Longboat Key
9.2 out of 10, Wonderful, (78 reviews)
"Great location just steps from the beach. Nice room for a little family weekend trip. The beach was beautiful & lots to do around the area. Definitely would love to come back! "
United States
Canaan B.
$388 nightly
The price is $433
Sep 22 - Sep 23
Total with taxes and fees
Poolside Peace – Silver Sands Resort #242 by RVA
On the beach, beach umbrellas

2. 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
$334 nightly
The price is $372
Sep 26 - Sep 27
Total with taxes and fees
1BR Beach Getaway – Silver Sands #254 by RVA
On the beach, beach umbrellas

3. Gulf Front Escape – Silver Sands #252 by RVA

Gulf Front Escape – Silver Sands #252 by RVA
Longboat Key
9.0 out of 10, Wonderful, (110 reviews)
"This place is a little dated but extremely clean! We will stay here again! The location to the beach was unmatchable!"
United States
Jessica C.
$332 nightly
The price is $370
Sep 22 - Sep 23
Total with taxes and fees
Gulf Front Escape – Silver Sands #252 by RVA
On the beach, beach umbrellas

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

Oceanfront 1BR – Silver Sands #257 by RVA
Longboat Key
8.8 out of 10, Excellent, (53 reviews)
"We loved this unit at Silver Sands and will book again. The only complaint we had was that there was a need for new pillows."
United States
Kinsley C.
$370 nightly
The price is $413
Sep 27 - Sep 28
Total with taxes and fees
Oceanfront 1BR – Silver Sands #257 by RVA
On the beach, beach umbrellas

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

Relax at Gulf – Silver Sands Resort #232, Longboat
Longboat Key
9.4 out of 10, Exceptional, (83 reviews)
"Very happy with my stay. Room was very clean, beautifully decorated and very comfortable. Perfect efficiency! Highly recommend"
United States
Gloria
$307 nightly
The price is $343
Sep 22 - Sep 23
Total with taxes and fees
Relax at Gulf – Silver Sands Resort #232, Longboat
On the beach, beach umbrellas

6. 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)
"Would def stay here again!"
United States
Tammie and David
$301 nightly
The price is $336
Sep 22 - Sep 23
Total with taxes and fees
Ground Floor, Steps to Sand – Silver Sands #243A by RVA
Beach nearby

7. Gulf Getaway – Beach Castle #12 by RVA

Gulf Getaway – Beach Castle #12 by RVA
Longboat Key
9.6 out of 10, Exceptional, (43 reviews)
"Amazing resort and housing. Will be back and enjoying all that Beach Castle has to offer!"
United States
Blake S.
$497 nightly
The price is $554
Sep 26 - Sep 27
Total with taxes and fees
Gulf Getaway – Beach Castle #12 by RVA
On the beach, beach umbrellas

8. 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.
$307 nightly
The price is $343
Sep 22 - Sep 23
Total with taxes and fees
Gulfside Resort – Silver Sands #241A by RVA
On the beach, sun loungers, beach towels

9. Sun, Sand, Savings: Open Tonite & Tomm, $100/nt + Fees!

Sun, Sand, Savings: Open Tonite & Tomm, $100/nt + Fees!
Longboat Key
10.0 out of 10, Exceptional, (97 reviews)
"Just got back from our long weekend trip to Longboat Key. Had a marvelous stay in the Vitamin Sea property. Everything was just perfect - really nice unit with all the necessities already stocked, steps from a beautiful beach and gorgeous sunsets, and great amenities (to include miniature golf)! Great pool for morning swims. Our host, Heidi, was a gem! Easy reservation/check-in and always making sure we had everything we needed. She even surprised us with a shell ornament gift and cinnamon...
United States
Richard
$226 nightly
The price is $252
Sep 22 - Sep 23
Total with taxes and fees
Sun, Sand, Savings: Open Tonite & Tomm, $100/nt + Fees!
On the beach, beach umbrellas

10. 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.
$299 nightly
The price is $333
Sep 22 - Sep 23
Total with taxes and fees
Silver Sands #245A Resort by RVA
On the beach, beach umbrellas

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

Affordable Beach Studio – Silver Sands #257A by RVA
Longboat Key
9.6 out of 10, Exceptional, (83 reviews)
"Lovely hotel right on the Gulf. Steps directly to the beach. Beautiful sunsets."
United States
SUSAN C.
$289 nightly
The price is $323
Sep 22 - Sep 23
Total with taxes and fees
Affordable Beach Studio – Silver Sands #257A by RVA
On the beach, beach umbrellas

12. Silver Sands #245S Resort by RVA

Silver Sands #245S Resort by RVA
Longboat Key
9.0 out of 10, Wonderful, (31 reviews)
"Location, pool out the patio door, clean beach, just steps out door to ocean. Great staff at check-in & out. Clean grounds"
United States
Nancy J.
$498 nightly
The price is $556
Sep 22 - Sep 23
Total with taxes and fees
Silver Sands #245S Resort by RVA
On the beach

13. Beachfront Studio – Cabana #5B by RVA

Beachfront Studio – Cabana #5B by RVA
Longboat Key
8.2 out of 10, Very good, (84 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.
$278 nightly
The price is $309
Sep 22 - Sep 23
Total with taxes and fees
Beachfront Studio – Cabana #5B by RVA
On the beach, beach umbrellas

14. 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)
"Beach was perfect!"
United States
Carmela D.
$309 nightly
The price is $345
Sep 22 - Sep 23
Total with taxes and fees
Sun, Sand & Silver Sands – Gulfside Resort #237 by RVA
Beach nearby

15. Seaside Escape – Beach Castle #24 by RVA

Seaside Escape – Beach Castle #24 by RVA
Longboat Key
9.2 out of 10, Wonderful, (51 reviews)
"Loved staying here"
United States
James
$298 nightly
The price is $332
Sep 26 - Sep 27
Total with taxes and fees
Seaside Escape – Beach Castle #24 by RVA
On the beach, beach umbrellas

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

Coastal Comfort – Silver Sands Resort #233 by RVA
Longboat Key
8.8 out of 10, Excellent, (35 reviews)
"3rd time here already booked another trip. So easy! Love it here!"
United States
Emily
$295 nightly
The price is $328
Sep 22 - Sep 23
Total with taxes and fees
Coastal Comfort – Silver Sands Resort #233 by RVA
On the beach, beach umbrellas

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

Starfish Studio Silver Sands #247A – Studio/1BA Resort in LBK
Longboat Key
8.2 out of 10, Very good, (10 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
$298 nightly
The price is $332
Sep 22 - Sep 23
Total with taxes and fees
Starfish Studio Silver Sands #247A – Studio/1BA Resort in LBK
Smart TV

18. Sunset and beach view from your balcony Unit 403

Sunset and beach view from your balcony Unit 403
Longboat Key
9.8 out of 10, Exceptional, (119 reviews)
"TCI is a great place to stay. Close to the beach, grocery store, shopping and walking paths. The condo was very clean and has all the amenities needed. The staff if very approachable and easy to connect with for any questions. This is our 2nd stay and we will return."
United States
Anonymous traveler
$344 nightly
The price is $380
Oct 4 - Oct 5
Total with taxes and fees
Sunset and beach view from your balcony Unit 403
TV

19. 2BR Gulfside Paradise – Longboat Key by RVA

2BR Gulfside Paradise – Longboat Key by RVA
Longboat Key
9.8 out of 10, Exceptional, (87 reviews)
"Beautiful location- perfect for the whole family."
United States
Dana B.
$466 nightly
The price is $520
Sep 29 - Sep 30
Total with taxes and fees
2BR Gulfside Paradise – Longboat Key by RVA
Smart TV

20. End of summer sale Take a peek awesome reviews 50 feet from sand

End of summer sale Take a peek awesome reviews 50 feet from sand
Longboat Key
10.0 out of 10, Exceptional, (152 reviews)
"This location is one of our favorite vacation spots - we try to come back every spring. This room was recently renovated and looks great, and the view of the beach is very relaxing. The host is very experienced and makes this trip a breeze. We’ll be back!"
United States
Angie E.
$540 nightly
The price is $602
Oct 8 - Oct 9
Total with taxes and fees
End of summer sale Take a peek awesome reviews 50 feet from sand
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

Zota Beach Resort

Zota Beach Resort

10/10 Excellent
"Good location and beautiful beach."
Manuel 1-night trip
Posted 2 hours ago
Zota Beach Resort

Price trends for vacation rentals in Longboat Key

Less expensive
More expensive
Next month
October
February
$371
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 $252 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?

Tropical Villas of Venice Beach: This vacation home rental near Longboat Key is located near the beach and has an outdoor pool, a terrace, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, a microwave, and kitchenware. Make the most of the garden in this rental home to help you unwind.

How many vacation rentals are there in Longboat Key?

Choose from 16 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. Lido Beach and Siesta Key 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.