Longboat Key Vacation Rentals

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

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

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.
$382 nightly
The price is $425
Jun 10 - Jun 11
Total with taxes and fees
Drift & Dune – Longboat Beachfront #101 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, (95 reviews)
"Great view, clean, beautiful!"
United States
Bethany
$393 nightly
The price is $438
Jun 12 - Jun 13
Total with taxes and fees
1BR Beach Getaway – Silver Sands #254 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, (91 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

Beachfront Bliss: Beach Castle #1 by RVA

Beachfront Bliss: Beach Castle #1 by RVA
Longboat Key
9.0 out of 10, Wonderful, (48 reviews)
"Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was more than satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Loved the property and beach"
United States
Gary G.
$504 nightly
The price is $561
Jun 9 - Jun 10
Total with taxes and fees
Beachfront Bliss: Beach Castle #1 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, (35 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: Very pleasant quiet community"
United States
Patty B.
$573 nightly
The price is $639
Jun 30 - Jul 1
Total with taxes and fees
Gulfside 2BR Condo–Silver Sands #257S
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 9 - Jun 10
Total with taxes and fees
Updated Beachfront Condo at Prestigious Long Boat Key Resort
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

Pool & Beach Access – Silver Sands #241S by RVA

Pool & Beach Access – Silver Sands #241S by RVA
Longboat Key
9.0 out of 10, Wonderful, (19 reviews)
"Perfect location, good amenities, super retro vibe!"
United States
Christopher W.
$483 nightly
The price is $538
Jun 9 - Jun 10
Total with taxes and fees
Pool & Beach Access – Silver Sands #241S by RVA
TV, offices

Gulf-View Beachfront Condo – Unit 203 – Longboat Key

Gulf-View Beachfront Condo – Unit 203 – Longboat Key
Longboat Key
$327 nightly
The price is $364
Jun 10 - Jun 11
Total with taxes and fees
Gulf-View Beachfront Condo – Unit 203 – Longboat Key
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, 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, (78 reviews)
"Right on beach-perfect for a short stay"
United States
Sean P.
$292 nightly
The price is $325
Jun 8 - Jun 9
Total with taxes and fees
Affordable Beach Studio – Silver Sands #257A by RVA
Outdoor dining

Island Time on LBK!

Island Time on LBK!
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.
$383 nightly
The price is $427
Jun 26 - Jun 27
Total with taxes and fees
Island Time on LBK!
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.
$302 nightly
The price is $336
Jun 8 - Jun 9
Total with taxes and fees
Seaside Escape – Beach Castle #24 by RVA
Beach nearby

Beach Castle Bliss #22 by RVA

Beach Castle Bliss #22 by RVA
Longboat Key
9.6 out of 10, Exceptional, (46 reviews)
"Great place to stay"
United States
Michael W.
$337 nightly
The price is $375
Jun 9 - Jun 10
Total with taxes and fees
Beach Castle Bliss #22 by RVA
On the beach

Oceanfront Oasis – Longboat Key 226 by RVA

Oceanfront Oasis – Longboat Key 226 by RVA
Longboat Key
9.2 out of 10, Wonderful, (132 reviews)
"Great beach!"
United States
Carolyn
$335 nightly
The price is $373
Jun 10 - Jun 11
Total with taxes and fees
Oceanfront Oasis – Longboat Key 226 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
9.2 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
$330 nightly
The price is $367
Jun 12 - Jun 13
Total with taxes and fees
Relax at Gulf – Silver Sands Resort #232, Longboat
On the beach

2BR Gulf View Condo Cabana Beach Club #7 by RVA

2BR Gulf View Condo Cabana Beach Club #7 by RVA
Longboat Key
9.6 out of 10, Exceptional, (76 reviews)
"It was a wonderful location "
United States
Kerri S.
$556 nightly
The price is $620
Jul 5 - Jul 6
Total with taxes and fees
2BR Gulf View Condo Cabana Beach Club #7 by RVA
On the beach

Luxurious Beachfront Jr. Suite by FVC

Luxurious Beachfront Jr. Suite by FVC
Longboat Key
9.4 out of 10, Exceptional, (80 reviews)
"The space was exactly as described, beautiful, comfortable, right on the beach with excellent balcony space. The kitchen has everything you need and the area is really amazing!"
United States
Debra J.
$679 nightly
The price is $755
Jun 20 - Jun 21
Total with taxes and fees
Luxurious Beachfront Jr. Suite by FVC
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
Jun 14 - Jun 15
Total with taxes and fees
Ground Floor, Steps to Sand – Silver Sands #243A by RVA
On the beach, sun loungers, beach towels

Ocean Breeze: Open Thursday & Friday, $199/nt + Fees!

Ocean Breeze: Open Thursday & Friday, $199/nt + Fees!
Longboat Key
10.0 out of 10, Exceptional, (93 reviews)
"Great accommodations, excellent location, amazing host!"
United States
Ella F.
$353 nightly
The price is $393
Jun 11 - Jun 12
Total with taxes and fees
Ocean Breeze: Open Thursday & Friday, $199/nt + Fees!
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Longboat Key Hotel Reviews

Zota Beach Resort

Zota Beach Resort

10/10 Excellent
"Staff was amazing! We will be back this summer for sure"
luis 1-night trip
Posted less than an hour 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 $342 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.