Longboat Key Vacation Rentals

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Our top choices for Longboat Key vacation rentals

Renovated Beach Paradise. Ground Floor unit 64

Renovated Beach Paradise. Ground Floor unit 64
Longboat Key
9.8 out of 10, Exceptional, (67 reviews)
"Everything was perfect the location was amazing Very clean and welcoming "
United States
Brian M.
$348 nightly
The price is $382
May 21 - May 22
Total with taxes and fees
Renovated Beach Paradise. Ground Floor unit 64

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
9.8 out of 10, Exceptional, (103 reviews)
"Location and view was amazing "
United States
joseph l.
Client texted view crazy Last minute cancellation Apr 25 - May 16th on sale

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.
$374 nightly
The price is $416
May 26 - May 27
Total with taxes and fees
Drift & Dune – Longboat Beachfront #101 RVA

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)
"Great stay and very friendly staff and host."
United States
Ida A.
$486 nightly
The price is $541
May 25 - May 26
Total with taxes and fees
Beach front 2 bed-2 bath private balcony, modern with Gulf front views

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, (90 reviews)
"Everything was great "
United States
kirt v.
$439 nightly
The price is $484
Jun 6 - Jun 7
Total with taxes and fees
Best views of the beach from your balcony Unit 301

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)
"Was very fun and we found sharks teeth on the beach. Everything was perfect i will be back "
United States
victor y.
$590 nightly
The price is $657
Jun 12 - Jun 13
Total with taxes and fees
Cabana Beach Club - Beachfront Stunning Ocean View *Snow Bird Promo* Winter 2027

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
$363 nightly
The price is $405
May 25 - May 26
Total with taxes and fees
1BR Beach Getaway – Silver Sands #254 by RVA

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
Jun 7 - Jun 8
Total with taxes and fees
Island Time!

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)
"Beautiful location"
United States
W Cabot T.
$795 nightly
The price is $886
May 26 - May 27
Total with taxes and fees
Updated Beachfront Condo at Prestigious Long Boat Key Resort

Bright Beach Studio – Silver Sands #255A by RVA

Bright Beach Studio – Silver Sands #255A by RVA
Longboat Key
8.8 out of 10, Excellent, (68 reviews)
"Perfect location and well-maintained unit - highly recommend!"
United States
Philip K.
$296 nightly
The price is $330
May 21 - May 22
Total with taxes and fees
Bright Beach Studio – Silver Sands #255A by RVA

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)
"The host staff were very helpful."
United States
Ann S.
$371 nightly
The price is $414
May 27 - May 28
Total with taxes and fees
Gulf Views – Silver Sands #250, Longboat Key by RVA

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, (113 reviews)
"Beach view with sunset!!"
United States
joseph l.
$393 nightly
The price is $434
Jun 18 - Jun 19
Total with taxes and fees
Sunset and beach view from your balcony Unit 403

Oceanfront Bliss–Longboat Key Beach 106 by RVA

Oceanfront Bliss–Longboat Key Beach 106 by RVA
Longboat Key
8.8 out of 10, Excellent, (98 reviews)
"Steps away from the beach. Clean place with Murphy Bed, but they had a foam topper in the closet. Nice chairs and umbrellas with nice beach and pool. Would stay again"
United States
Anonymous traveler
$269 nightly
The price is $300
May 24 - May 25
Total with taxes and fees
Oceanfront Bliss–Longboat Key Beach 106 by RVA

THE BEACH CONDO #107 BEACHFRONT FULL VIEW

THE BEACH CONDO #107 BEACHFRONT FULL VIEW
Longboat Key
9.8 out of 10, Exceptional, (89 reviews)
"Beautiful location and the beach is amazing "
United States
Heather A.
$379 nightly
The price is $423
May 25 - May 26
Total with taxes and fees
THE BEACH CONDO #107 BEACHFRONT FULL VIEW

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)
"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.
$300 nightly
The price is $335
May 25 - May 26
Total with taxes and fees
Ground Floor, Steps to Sand – Silver Sands #243A 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, (103 reviews)
"Staff was welcoming- place was clean and stay was great"
United States
Joseph S.
$344 nightly
The price is $383
May 25 - May 26
Total with taxes and fees
Gulf Front Escape – Silver Sands #252 by RVA

Gulf Breezes & Poolside Peace – Silver Sands #236 by RVA

Gulf Breezes & Poolside Peace – Silver Sands #236 by RVA
Longboat Key
9.2 out of 10, Wonderful, (79 reviews)
"We had a pleasant stay with no issues. Pool was warm and beach was very nice with plenty of soft dry sand up top. They have lounge chairs for you to use in both of these areas."
United States
Mark R.
$316 nightly
The price is $352
May 31 - Jun 1
Total with taxes and fees
Gulf Breezes & Poolside Peace – Silver Sands #236 by 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, (78 reviews)
"Right on beach-perfect for a short stay"
United States
Sean P.
$289 nightly
The price is $322
May 21 - May 22
Total with taxes and fees
Affordable Beach Studio – Silver Sands #257A by 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, (42 reviews)
"Enjoyed our stay"
United States
Susan C.
$309 nightly
The price is $344
May 31 - Jun 1
Total with taxes and fees
Sun, Sand & Silver Sands – Gulfside Resort #237 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.
$307 nightly
The price is $342
May 21 - May 22
Total with taxes and fees
Beachside Studio – Silver Sands #253A, Longboat Key
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
September
February
$454
Month
Price
January
$428
February
$567
March
$531
April
$448
May
$376
June
$454
July
$476
August
$398
September
$366
October
$383
November
$380
December
$427
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 $300 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 22 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.