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Longboat Key Vacation Rentals

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Our top choices for Longboat Key vacation rentals

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
$363 nightly
The price is $405
Jul 19 - Jul 20
Total with taxes and fees
1BR Beach Getaway – Silver Sands #254 by RVA

Oceanfront Bliss–Longboat Key Beach 106 by RVA

Oceanfront Bliss–Longboat Key Beach 106 by RVA
Longboat Key
8.8 out of 10, Excellent, (102 reviews)
"Beautiful sunset view. "
United States
Rhonda V.
$314 nightly
The price is $350
Jul 19 - Jul 20
Total with taxes and fees
Oceanfront Bliss–Longboat Key Beach 106 by RVA

Roomy 2BR Retreat – Silver Sands #239 by RVA

Roomy 2BR Retreat – Silver Sands #239 by RVA
Longboat Key
9.6 out of 10, Exceptional, (48 reviews)
"Condo was great! Lots of space, clean, and great location"
United States
Sherry R.
$420 nightly
The price is $468
Jun 28 - Jun 29
Total with taxes and fees
Roomy 2BR Retreat – Silver Sands #239 by RVA

Drift & Dune – Longboat Beachfront #101 RVA

Drift & Dune – Longboat Beachfront #101 RVA
Longboat Key
8.6 out of 10, Excellent, (82 reviews)
"Check in and out was easy, the pool and condo were great, and the location was awesome!"
United States
Bailey B.
$476 nightly
The price is $531
Jun 28 - Jun 29
Total with taxes and fees
Drift & Dune – Longboat Beachfront #101 RVA

Relax at Gulf – Silver Sands Resort #232, Longboat

Relax at Gulf – Silver Sands Resort #232, Longboat
Longboat Key
9.2 out of 10, Wonderful, (80 reviews)
"Very happy with my stay. Room was very clean, beautifully decorated and very comfortable. Perfect efficiency! Highly recommend"
United States
Gloria
$318 nightly
The price is $354
Jul 26 - Jul 27
Total with taxes and fees
Relax at Gulf – Silver Sands Resort #232, Longboat

THE BEACH CONDO #107 BEACHFRONT FULL VIEW

THE BEACH CONDO #107 BEACHFRONT FULL VIEW
Longboat Key
10.0 out of 10, Exceptional, (92 reviews)
"Host was wondeful!Location and condo fabulous!"
United States
Linda D.
$410 nightly
The price is $457
Jul 5 - Jul 6
Total with taxes and fees
THE BEACH CONDO #107 BEACHFRONT FULL VIEW

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, (268 reviews)
"Great location for the price! Also, it was well equipped with everything you need."
United States
LJ G.
$595 nightly
The price is $662
Jul 13 - Jul 14
Total with taxes and fees
Cabana Beach Club - Beachfront Stunning Ocean View *Snow Bird Promo* Winter 2027

Island Time: Open July 7 - 10!

Island Time: Open July 7 - 10!
Longboat Key
10.0 out of 10, Exceptional, (129 reviews)
"Great host! Amazing location. Loved the beach access and views! Highly recommended "
United States
Bonnie N.
$381 nightly
The price is $425
Jul 19 - Jul 20
Total with taxes and fees
Island Time: Open July 7 - 10!

Charming 1-bedroom, beachfront condo in marvelous Longboat Key

Charming 1-bedroom, beachfront condo in marvelous Longboat Key
Longboat Key
9.0 out of 10, Wonderful, (56 reviews)
"Adorable and clean place. Perfect location with beach and pool so close by. Loved everything about the stay!"
United States
Alene D.
$400 nightly
The price is $446
Jun 28 - Jun 29
Total with taxes and fees
Charming 1-bedroom, beachfront condo in marvelous Longboat Key

Oceanfront Oasis – Longboat Key 226 by RVA

Oceanfront Oasis – Longboat Key 226 by RVA
Longboat Key
9.2 out of 10, Wonderful, (133 reviews)
"Great beach!"
United States
Carolyn
$379 nightly
The price is $422
Jun 29 - Jun 30
Total with taxes and fees
Oceanfront Oasis – Longboat Key 226 by RVA

Sandy Toes: Open July 26 - 31!

Sandy Toes: Open July 26 - 31!
Longboat Key
9.8 out of 10, Exceptional, (13 reviews)
"We had a wonderful stay, the condo was very well equipped and the host was absolutely fantastic! "
United States
Emily L.
$409 nightly
The price is $456
Jul 21 - Jul 22
Total with taxes and fees
Sandy Toes: Open July 26 - 31!

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, (79 reviews)
"The host staff were very helpful."
United States
Ann S.
$397 nightly
The price is $442
Jul 19 - Jul 20
Total with taxes and fees
Gulf Views – Silver Sands #250, Longboat Key by RVA

Gulf Front Escape – Silver Sands #252 by RVA

Gulf Front Escape – Silver Sands #252 by RVA
Longboat Key
9.2 out of 10, Wonderful, (104 reviews)
"Staff was welcoming- place was clean and stay was great"
United States
Joseph S.
$344 nightly
The price is $384
Jul 19 - Jul 20
Total with taxes and fees
Gulf Front Escape – Silver Sands #252 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)
"Great location, and it was a clean, updated, and comfortable stay!!"
United States
Brian B.
$659 nightly
The price is $734
Jun 27 - Jun 28
Total with taxes and fees
Updated Beachfront Condo at Prestigious Long Boat Key Resort

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.
$302 nightly
The price is $337
Jun 30 - Jul 1
Total with taxes and fees
Ground Floor, Steps to Sand – Silver Sands #243A by RVA

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.
$327 nightly
The price is $364
Jul 23 - Jul 24
Total with taxes and fees
Newly Renovated 1BR – Cabana Beach #5 RVA

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
Jun 28 - Jun 29
Total with taxes and fees
Sun, Sand & Silver Sands – Gulfside Resort #237 by RVA

Silver Sands #245A Resort by RVA

Silver Sands #245A Resort by RVA
Longboat Key
8.6 out of 10, Excellent, (62 reviews)
"Location and facilities wer excellent. "
United States
donald m.
$306 nightly
The price is $341
Jun 28 - Jun 29
Total with taxes and fees
Silver Sands #245A Resort by RVA

Beachside Studio – Silver Sands #253A, Longboat Key

Beachside Studio – Silver Sands #253A, Longboat Key
Longboat Key
8.4 out of 10, Very Good, (38 reviews)
"I really enjoyed my stay at the Silver Sands and will recommend your property"
United States
Jeff H.
$295 nightly
The price is $329
Jun 30 - Jul 1
Total with taxes and fees
Beachside Studio – Silver Sands #253A, Longboat Key

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, (81 reviews)
"Great location and great views!"
United States
Mark H.
$375 nightly
The price is $418
Jul 15 - Jul 16
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
October
February
$458
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 $341 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 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. Our travelers also rate Country Club Long Boat Key Beach Villa 2B 3BA Pool as a favorite home for rent in Longboat Key.

How many vacation rentals are there in Longboat Key?

Choose from 26 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.