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
Aug 7 - Aug 9
In two months
Sep 18 - Sep 20
In three months
Oct 16 - Oct 18
In four months
Nov 13 - Nov 15

Our top choices for Longboat Key vacation rentals

On the beach

Beachfront Haven – Beach Castle #3 by RVA

Beachfront Haven – Beach Castle #3 by RVA
Longboat Key
9.2 out of 10, Wonderful, (58 reviews)
"The view was beautiful and much more unobstructed than I expected. Loved the private beach and access to chairs, propane grill and community pool."
United States
Dawn A.
Beachfront Haven – Beach Castle #3 by RVA
On the beach, sun loungers, beach towels

On the Gulf: Open July 27th & 28th!

On the Gulf: Open July 27th & 28th!
Longboat Key
10.0 out of 10, Exceptional, (94 reviews)
"The room has direct beach access, plenty of beach chairs. The water and amenities are beautiful, very comfortable bed and the owner couldn't have been any more pleasant or easier to deal with. We had a great stay. 5 stars."
United States
Chuck B.
$383 nightly
The price is $427
Aug 5 - Aug 6
Total with taxes and fees
On the Gulf: Open July 27th & 28th!
On the beach, beach umbrellas

Silver Sands 1BR – Gulfside Comfort #255 by RVA

Silver Sands 1BR – Gulfside Comfort #255 by RVA
Longboat Key
9.0 out of 10, Wonderful, (88 reviews)
"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: Beautiful beach, would stay again."
United States
Michael M.
$342 nightly
The price is $381
Aug 9 - Aug 10
Total with taxes and fees
Silver Sands 1BR – Gulfside Comfort #255 by RVA
On the beach, beach umbrellas

Gulfside 2BR Condo–Silver Sands #257S

Gulfside 2BR Condo–Silver Sands #257S
Longboat Key
8.6 out of 10, Excellent, (36 reviews)
"The location was perfect right on the beach"
United States
Ana
$514 nightly
The price is $574
Aug 11 - Aug 12
Total with taxes and fees
Gulfside 2BR Condo–Silver Sands #257S
On the beach, beach umbrellas

Affordable Beach Studio – Silver Sands #257A by RVA

Affordable Beach Studio – Silver Sands #257A by RVA
Longboat Key
9.6 out of 10, Exceptional, (80 reviews)
"Thirty steps to the sand! This unit was perfect for my one-person getaway to the beach. Clean and safe, friendly staff, and great location. I'll be back!"
United States
Susan F.
$292 nightly
The price is $325
Aug 9 - Aug 10
Total with taxes and fees
Affordable Beach Studio – Silver Sands #257A by RVA
On the beach, beach umbrellas

Gulf Front Escape – Silver Sands #252 by RVA

Gulf Front Escape – Silver Sands #252 by RVA
Longboat Key
9.0 out of 10, Wonderful, (106 reviews)
"Staff was welcoming- place was clean and stay was great"
United States
Joseph S.
$340 nightly
The price is $380
Aug 16 - Aug 17
Total with taxes and fees
Gulf Front Escape – Silver Sands #252 by RVA
Smart TV

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, (115 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
$371 nightly
The price is $408
Aug 9 - Aug 10
Total with taxes and fees
Sunset and beach view from your balcony Unit 403
Beach nearby

Beach Castle Bliss #22 by RVA

Beach Castle Bliss #22 by RVA
Longboat Key
9.6 out of 10, Exceptional, (47 reviews)
"Great place to stay"
United States
Michael W.
$324 nightly
The price is $361
Jul 26 - Jul 27
Total with taxes and fees
Beach Castle Bliss #22 by RVA
Property grounds

Cabana Beach Club - Beachfront Stunning Ocean View *Snow Bird Promo* Winter 2027

Cabana Beach Club - Beachfront Stunning Ocean View *Snow Bird Promo* Winter 2027
Longboat Key
9.8 out of 10, Exceptional, (269 reviews)
"Great location for the price! Also, it was well equipped with everything you need."
United States
LJ G.
$596 nightly
The price is $663
Jul 30 - Jul 31
Total with taxes and fees
Cabana Beach Club - Beachfront Stunning Ocean View *Snow Bird Promo* Winter 2027
On the beach, beach umbrellas

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)
"Beach is beautiful, location is great. Room was clean. Rhe bed"
United States
Kellie B.
$308 nightly
The price is $343
Jul 21 - Jul 22
Total with taxes and fees
Gulfside Resort – Silver Sands #241A by RVA
On the beach, beach umbrellas

Relax at Gulf – Silver Sands Resort #232, Longboat

Relax at Gulf – Silver Sands Resort #232, Longboat
Longboat Key
9.4 out of 10, Exceptional, (81 reviews)
"Very happy with my stay. Room was very clean, beautifully decorated and very comfortable. Perfect efficiency! Highly recommend"
United States
Gloria
$319 nightly
The price is $355
Jul 22 - Jul 23
Total with taxes and fees
Relax at Gulf – Silver Sands Resort #232, Longboat
Beach nearby

Seaside Escape – Beach Castle #24 by RVA

Seaside Escape – Beach Castle #24 by RVA
Longboat Key
9.2 out of 10, Wonderful, (49 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.
$316 nightly
The price is $352
Jul 26 - Jul 27
Total with taxes and fees
Seaside Escape – Beach Castle #24 by RVA
On the beach, beach umbrellas

Bright Beach Studio – Silver Sands #255A by RVA

Bright Beach Studio – Silver Sands #255A by RVA
Longboat Key
8.8 out of 10, Excellent, (69 reviews)
"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: Our experience was fantastic and everything was just as described. The place was clean and close to everything."
United States
Chris C.
$297 nightly
The price is $331
Jul 21 - Jul 22
Total with taxes and fees
Bright Beach Studio – Silver Sands #255A by RVA
On the beach

Beachfront Studio – Cabana #5B by RVA

Beachfront Studio – Cabana #5B by RVA
Longboat Key
8.2 out of 10, Very Good, (81 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 $310
Jul 23 - Jul 24
Total with taxes and fees
Beachfront Studio – Cabana #5B by RVA
On the beach, beach umbrellas

1BR Beach Getaway – Silver Sands #254 by RVA

1BR Beach Getaway – Silver Sands #254 by RVA
Longboat Key
9.2 out of 10, Wonderful, (96 reviews)
"Great view, clean, beautiful!"
United States
Bethany
$336 nightly
The price is $374
Jul 22 - Jul 23
Total with taxes and fees
1BR Beach Getaway – Silver Sands #254 by RVA
On the beach, beach umbrellas

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, (43 reviews)
"Enjoyed our stay"
United States
Susan C.
$308 nightly
The price is $343
Aug 11 - Aug 12
Total with taxes and fees
Sun, Sand & Silver Sands – Gulfside Resort #237 by RVA
On the beach, beach umbrellas

Silver Sands #245S Resort by RVA

Silver Sands #245S Resort by RVA
Longboat Key
9.0 out of 10, Wonderful, (30 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.
$453 nightly
The price is $504
Jul 21 - Jul 22
Total with taxes and fees
Silver Sands #245S Resort by RVA
On the beach, beach umbrellas

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, (63 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.
$303 nightly
The price is $338
Jul 22 - Jul 23
Total with taxes and fees
Ground Floor, Steps to Sand – Silver Sands #243A by RVA
On the beach, beach umbrellas

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
$300 nightly
The price is $334
Aug 9 - Aug 10
Total with taxes and fees
Starfish Studio Silver Sands #247A – Studio/1BA Resort in LBK
Property grounds

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, (211 reviews)
"Great location."
United States
Janet B.
$548 nightly
The price is $610
Jul 26 - Jul 27
Total with taxes and fees
Are you ready for a luxury 5-floor penthouse 60 ft from water, 207 reviews
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

Oceanfront Oasis – Longboat Key 226 by RVA

Oceanfront Oasis – Longboat Key 226 by RVA

10/10 Excellent
"The ocean view was great. The room was very clean and we enjoyed the stay."
Sherri G. 2-night trip
Posted 4 days ago
Oceanfront Oasis – Longboat Key 226 by RVA

Price trends for vacation rentals in Longboat Key

Less expensive
More expensive
Next month
October
February
$384
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 $310 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 free 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. 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.