Longboat Key Vacation Rentals

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Check prices for these dates

In two weeks
Jun 19 - Jun 21
In two months
Jul 31 - Aug 2
In three months
Aug 28 - Aug 30
In four months
Sep 25 - Sep 27

Our top choices for Longboat Key vacation rentals

On the beach

2 Bedroom Beachfront Condo by FVC

2 Bedroom Beachfront Condo by FVC
Longboat Key
9.6 out of 10, Exceptional, (45 reviews)
"Beautiful property with oversized balcony terrific for watching sunsets. Sandy beach was wonderful as was the pool. Property manager (FVC) was great to work with. Definitely recommend. "
United States
Daniel M.
2 Bedroom Beachfront Condo by FVC
Beach nearby

Renovated Beach Paradise. Ground Floor unit 64

Renovated Beach Paradise. Ground Floor unit 64
Longboat Key
9.8 out of 10, Exceptional, (68 reviews)
"Everything was perfect the location was amazing Very clean and welcoming "
United States
Brian M.
$359 nightly
The price is $395
Jun 7 - Jun 8
Total with taxes and fees
Renovated Beach Paradise. Ground Floor unit 64
On the beach

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.
$392 nightly
The price is $437
Jun 7 - Jun 8
Total with taxes and fees
Drift & Dune – Longboat Beachfront #101 RVA
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)
"Location #1. Clean #2"
United States
Eric C.
$396 nightly
The price is $441
Jun 24 - Jun 25
Total with taxes and fees
Silver Sands 1BR – Gulfside Comfort #255 by RVA
Beach nearby

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.
$380 nightly
The price is $418
Jun 12 - Jun 13
Total with taxes and fees
Best views of the beach from your balcony Unit 301
On the beach, beach umbrellas

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.
$376 nightly
The price is $419
Jun 10 - Jun 11
Total with taxes and fees
Gulf Views – Silver Sands #250, Longboat Key by RVA
Outdoor dining

Island Time on LBK: Open Sunday, $175/nt + Fees!

Island Time on LBK: Open Sunday, $175/nt + Fees!
Longboat Key
10.0 out of 10, Exceptional, (126 reviews)
"Great host! Amazing location. Loved the beach access and views! Highly recommended "
United States
Bonnie N.
$322 nightly
The price is $359
Jun 7 - Jun 8
Total with taxes and fees
Island Time on LBK: Open Sunday, $175/nt + Fees!
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.
$304 nightly
The price is $339
Jun 14 - Jun 15
Total with taxes and fees
Ground Floor, Steps to Sand – Silver Sands #243A 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
9.2 out of 10, Wonderful, (104 reviews)
"Staff was welcoming- place was clean and stay was great"
United States
Joseph S.
$348 nightly
The price is $387
Jun 10 - Jun 11
Total with taxes and fees
Gulf Front Escape – Silver Sands #252 by RVA
On the beach

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, (52 reviews)
"Great location. "
United States
Maureen R.
$400 nightly
The price is $446
Jun 17 - Jun 18
Total with taxes and fees
Charming 1-bedroom, beachfront condo in marvelous Longboat Key
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, (95 reviews)
"Great view, clean, beautiful!"
United States
Bethany
$414 nightly
The price is $461
Jun 12 - Jun 13
Total with taxes and fees
1BR Beach Getaway – Silver Sands #254 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, (78 reviews)
"The pool was disgusting, dirt and debris on the bottom and top so that was disappointing, while watching TV and sleeping a person actually opened up our porch door then the main door and just walked in and said they had booked the same room and had keys, what kind of place does not keep track of that and I'm not sure what the person was thinking the TV was on and it was up a little so I know they heard it from the outside but to get back to that place for allowing that to happen. He's lucky I...
United States
Joseph
Beachfront Studio – Cabana #5B by RVA
Dining

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.
$338 nightly
The price is $377
Jun 7 - Jun 8
Total with taxes and fees
The Beach on Longboat Key #227 Resort by RVA
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)
"We enjoyed this fun spot with private beach, pool, and more!"
United States
Willow C.
$310 nightly
The price is $345
Jun 9 - Jun 10
Total with taxes and fees
Gulfside Resort – Silver Sands #241A 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, (268 reviews)
"The unit has a perfect balcony view of the beach. The space was very clean and comfortable with many amenities including coolers and beach umbrellas. The property provides nice lounge chairs for the beach. The host Anna was quickly responsive to our questions and needs during our visit. Highly recommend this property !"
United States
Tracey s.
$597 nightly
The price is $664
Jun 20 - Jun 21
Total with taxes and fees
Cabana Beach Club - Beachfront Stunning Ocean View *Snow Bird Promo* Winter 2027
On the beach

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.
$795 nightly
The price is $886
Jun 8 - Jun 9
Total with taxes and fees
Updated Beachfront Condo at Prestigious Long Boat Key Resort
On the beach, beach umbrellas

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
$316 nightly
The price is $353
Jun 7 - Jun 8
Total with taxes and fees
Relax at Gulf – Silver Sands Resort #232, Longboat
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)
"We arrived late in the day and found the check in process well thought out and easy. The unit was very clean, the office staff very friendly and helpful. The whole facility was very quiet. Finally, the location was great, right on the beach. "
United States
Hal S.
Sunset and beach view from your balcony Unit 403
On the beach, sun loungers, beach towels

THE BEACH CONDO #107 BEACHFRONT FULL VIEW

THE BEACH CONDO #107 BEACHFRONT FULL VIEW
Longboat Key
9.8 out of 10, Exceptional, (93 reviews)
"Host was wondeful!Location and condo fabulous!"
United States
Linda D.
$409 nightly
The price is $456
Jul 5 - Jul 6
Total with taxes and fees
THE BEACH CONDO #107 BEACHFRONT FULL VIEW
On the beach, beach umbrellas

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.
$336 nightly
The price is $375
Jun 24 - Jun 25
Total with taxes and fees
Silver Sands #245A 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

Zota Beach Resort

Zota Beach Resort

10/10 Excellent
"Todo bien"
Jesus 2-night trip
Posted 9 hours ago
Zota Beach Resort

Price trends for vacation rentals in Longboat Key

Less expensive
More expensive
This month
Next month
October
February
$463
$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 $322 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 24 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.