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Longboat Key Vacation Rentals

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Our top choices for Longboat Key vacation rentals

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, (91 reviews)
"Everything was great "
United States
kirt v.
$422 nightly
The price is $466
Jun 21 - Jun 22
Total with taxes and fees
Best views of the beach from your balcony Unit 301

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.
$274 nightly
The price is $306
Jun 21 - Jun 22
Total with taxes and fees
Oceanfront Bliss–Longboat Key Beach 106 by RVA

Beachfront- Longboat Key efficiency condo w/ king size bed, steps to sand.

Beachfront- Longboat Key efficiency condo w/ king size bed, steps to sand.
Longboat Key
8.4 out of 10, Very Good, (19 reviews)
"Excellent place to stay. "
United States
Hadley R.
$320 nightly
The price is $356
Jul 5 - Jul 6
Total with taxes and fees
Beachfront- Longboat Key efficiency condo w/ king size bed, steps to sand.

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.
$411 nightly
The price is $458
Jun 23 - Jun 24
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.
$587 nightly
The price is $654
Jul 13 - Jul 14
Total with taxes and fees
Cabana Beach Club - Beachfront Stunning Ocean View *Snow Bird Promo* Winter 2027

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.
$309 nightly
The price is $344
Jun 21 - Jun 22
Total with taxes and fees
Gulfside Resort – Silver Sands #241A by RVA

Island Time: Open July 7 - 10!

Island Time: Open July 7 - 10!
Longboat Key
10.0 out of 10, Exceptional, (127 reviews)
"Great host! Amazing location. Loved the beach access and views! Highly recommended "
United States
Bonnie N.
$383 nightly
The price is $427
Jul 19 - Jul 20
Total with taxes and fees
Island Time: Open July 7 - 10!

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
$331 nightly
The price is $369
Jun 21 - Jun 22
Total with taxes and fees
1BR Beach Getaway – Silver Sands #254 by RVA

Step from the Beach.Renovated ground Floor unit 63

Step from the Beach.Renovated ground Floor unit 63
Longboat Key
9.4 out of 10, Exceptional, (72 reviews)
"Our stay was excellent. Nice and clean and plenty of room however it doesn’t have a beach view, but the beach is a very short, easy walk. Staff was extra nice, especially Margaret."
United States
Faye
$319 nightly
The price is $352
Jun 24 - Jun 25
Total with taxes and fees
Step from the Beach.Renovated ground Floor unit 63

50 ft from sand, Private Island 125 +review

50 ft from sand, Private Island 125 +review
Longboat Key
10.0 out of 10, Exceptional, (134 reviews)
"Jim is a great host - he is great at communicating before, during, and at the end of the stay. The condo we stayed in was exactly as described and was wonderful!!"
United States
Robin G.
$539 nightly
The price is $601
Jun 21 - Jun 22
Total with taxes and fees
50 ft from sand, Private Island 125 +review

Vitamin Sea: Open Tuesday, $199/nt + Fees!

Vitamin Sea: Open Tuesday, $199/nt + Fees!
Longboat Key
10.0 out of 10, Exceptional, (93 reviews)
"Great accommodations, excellent location, amazing host!"
United States
Ella F.
$376 nightly
The price is $419
Jun 23 - Jun 24
Total with taxes and fees
Vitamin Sea: Open Tuesday, $199/nt + Fees!

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)
"Location #1. Clean #2"
United States
Eric C.
$341 nightly
The price is $380
Jun 24 - Jun 25
Total with taxes and fees
Silver Sands 1BR – Gulfside Comfort #255 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)
$664 nightly
The price is $739
Jun 22 - Jun 23
Total with taxes and fees
Updated Beachfront Condo at Prestigious Long Boat Key Resort

Drift & Dune – Longboat Beachfront #101 RVA

Drift & Dune – Longboat Beachfront #101 RVA
Longboat Key
8.6 out of 10, Excellent, (81 reviews)
"Check in and out was easy, the pool and condo were great, and the location was awesome!"
United States
Bailey B.
$592 nightly
The price is $660
Jun 30 - Jul 1
Total with taxes and fees
Drift & Dune – Longboat Beachfront #101 RVA

Steps to Beach – Silver Sands 2BR Condo #243S by RVA

Steps to Beach – Silver Sands 2BR Condo #243S by RVA
Longboat Key
9.2 out of 10, Wonderful, (33 reviews)
"Extremely convenient access to beach, Large pool, putting green, and pool toys made our stay very fun. "
United States
Maria
$482 nightly
The price is $537
Jun 24 - Jun 25
Total with taxes and fees
Steps to Beach – Silver Sands 2BR Condo #243S 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.
$341 nightly
The price is $381
Jun 21 - Jun 22
Total with taxes and fees
Gulf Front Escape – Silver Sands #252 by 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
$298 nightly
The price is $333
Jun 21 - Jun 22
Total with taxes and fees
Relax at Gulf – Silver Sands Resort #232, Longboat

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 24 - Jun 25
Total with taxes and fees
Ground Floor, Steps to Sand – Silver Sands #243A by RVA

Sandy Toes: Open July 26 - 31!

Sandy Toes: Open July 26 - 31!
Longboat Key
9.8 out of 10, Exceptional, (12 reviews)
"We had a wonderful stay, the condo was very well equipped and the host was absolutely fantastic! "
United States
Emily L.
$383 nightly
The price is $427
Jul 8 - Jul 9
Total with taxes and fees
Sandy Toes: Open July 26 - 31!

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.
$371 nightly
The price is $413
Jul 21 - Jul 22
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 $323 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 23 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 Coquina 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.