A coastal cityscape with a sunset over the water, featuring several high-rise buildings and palm trees.

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
Jul 17 - Jul 19
In two months
Aug 28 - Aug 30
In three months
Sep 25 - Sep 27
In four months
Oct 23 - Oct 25

Our top choices for Longboat Key vacation rentals

On the beach, sun loungers, beach towels

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.
$406 nightly
The price is $453
Jul 5 - Jul 6
Total with taxes and fees
THE BEACH CONDO #107 BEACHFRONT FULL VIEW
Outdoor dining

Island Time: Open Sun, July 19th, $250/nt + Fees!

Island Time: Open Sun, July 19th, $250/nt + Fees!
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.
$410 nightly
The price is $457
Jul 19 - Jul 20
Total with taxes and fees
Island Time: Open Sun, July 19th, $250/nt + Fees!
Property grounds

Are you ready for a luxury 5-floor penthouse 60 ft from water, 207 reviews

Are you ready for a luxury 5-floor penthouse 60 ft from water, 207 reviews
Longboat Key
10.0 out of 10, Exceptional, (210 reviews)
"Great location."
United States
Janet B.
$543 nightly
The price is $605
Jul 11 - Jul 12
Total with taxes and fees
Are you ready for a luxury 5-floor penthouse 60 ft from water, 207 reviews
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
$318 nightly
The price is $355
Jul 12 - Jul 13
Total with taxes and fees
Relax at Gulf – Silver Sands Resort #232, Longboat
On the beach

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, (49 reviews)
"Beautiful view and beach!"
United States
Rebecca M.
$483 nightly
The price is $538
Jul 28 - Jul 29
Total with taxes and fees
Beach front 2 bed-2 bath private balcony, modern with Gulf front views
Smart TV

Take a peek awesome reviews 50 feet from sand

Take a peek awesome reviews 50 feet from sand
Longboat Key
10.0 out of 10, Exceptional, (147 reviews)
"A very considerate and available host! The condo was everything we could have wanted. Great location! Will return"
United States
Kathleen R.
$544 nightly
The price is $606
Jul 9 - Jul 10
Total with taxes and fees
Take a peek awesome reviews 50 feet from sand
On the beach

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.
$309 nightly
The price is $344
Jul 6 - Jul 7
Total with taxes and fees
Oceanfront Bliss–Longboat Key Beach 106 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)
"Great location for the price! Also, it was well equipped with everything you need."
United States
LJ G.
$596 nightly
The price is $663
Jul 13 - Jul 14
Total with taxes and fees
Cabana Beach Club - Beachfront Stunning Ocean View *Snow Bird Promo* Winter 2027
Exterior

Beach Bliss: Open Wednesday, July 8th, $250/nt + Fees!

Beach Bliss: Open Wednesday, July 8th, $250/nt + Fees!
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.
$379 nightly
The price is $423
Jul 21 - Jul 22
Total with taxes and fees
Beach Bliss: Open Wednesday, July 8th, $250/nt + Fees!
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.
$661 nightly
The price is $736
Jul 6 - Jul 7
Total with taxes and fees
Updated Beachfront Condo at Prestigious Long Boat Key Resort
On the beach, sun loungers, beach towels

Vitamin Seaside: Open July 27th - 31st!

Vitamin Seaside: Open July 27th - 31st!
Longboat Key
10.0 out of 10, Exceptional, (93 reviews)
"Great accommodations, excellent location, amazing host!"
United States
Ella F.
$473 nightly
The price is $528
Jul 27 - Jul 28
Total with taxes and fees
Vitamin Seaside: Open July 27th - 31st!
On the beach, beach umbrellas

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
$480 nightly
The price is $535
Jul 26 - Jul 27
Total with taxes and fees
Steps to Beach – Silver Sands 2BR Condo #243S by 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)
"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: Beautiful beach, would stay again."
United States
Michael M.
$359 nightly
The price is $400
Jul 11 - Jul 12
Total with taxes and fees
Silver Sands 1BR – Gulfside Comfort #255 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.
$341 nightly
The price is $380
Jul 15 - Jul 16
Total with taxes and fees
The Beach on Longboat Key #227 Resort by RVA
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
Jul 19 - Jul 20
Total with taxes and fees
Ground Floor, Steps to Sand – Silver Sands #243A by RVA
Beach nearby

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
$337 nightly
The price is $372
Jul 11 - Jul 12
Total with taxes and fees
Step from the Beach.Renovated ground Floor unit 63
TV, offices

Sunset and beach view from your balcony Unit 501

Sunset and beach view from your balcony Unit 501
Longboat Key
$350 nightly
The price is $390
Jul 19 - Jul 20
Total with taxes and fees
Sunset and beach view from your balcony Unit 501
On the beach, beach umbrellas

Cozy Beach Studio – Silver Sands #251A by RVA

Cozy Beach Studio – Silver Sands #251A by RVA
Longboat Key
8.6 out of 10, Excellent, (54 reviews)
"Rating Details: The property manager was very helpful. The vacation rental was clean. 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: Great place I myself like the bigger rooms,"
United States
Susan G.
$290 nightly
The price is $323
Jul 5 - Jul 6
Total with taxes and fees
Cozy Beach Studio – Silver Sands #251A by RVA
On the beach, beach umbrellas

Bright Beach Studio – Silver Sands #255A by RVA

Bright Beach Studio – Silver Sands #255A by RVA
Longboat Key
8.8 out of 10, Excellent, (69 reviews)
"The communication was excellent and the staff very friendly. I would recommend this stay for anyone requiring a small room with easy beach access. My only negative was that the bathroomneeds updating. Overall this is a great location for beach lovers! "
United States
rebecca g.
$298 nightly
The price is $332
Jul 6 - Jul 7
Total with taxes and fees
Bright Beach Studio – Silver Sands #255A by RVA
On the beach, beach umbrellas

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
Jul 5 - Jul 6
Total with taxes and fees
Sun, Sand & Silver Sands – Gulfside Resort #237 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.
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

8/10 Good
"We chose this location for our weekend honeymoon. This hotel is beautiful and so well maintained. The only reason I'm giving a 4 star review is because the AC wasn't working on our first night. When we called Front Desk we were given a new room. They gave us keys and all, and when we walked into the new room it was dirty and there were no sheets, meaning it was a room that was not ready. No other room was available, so we had to sleep back in our original 78 degrees room with two fans they were kind to offer. The reason I mention this incident is with no intention to discredit this hotel, its just that we were so tired and hot after the weeding we were looking forward to some rest. After that moment, everything was perfect. The staff was great. AC was fixed next morning, The Viento restaurant was the highlight of our stay, all thanks to our server Roger who was the most attentive and gentle server. The food was A+. Beach A++. We would love to go back in the future :)"
Anel 3-night trip
Posted 7 hours ago
Zota Beach Resort

Price trends for vacation rentals in Longboat Key

Less expensive
More expensive
This month
Next month
October
February
$458
$384
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 $311 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?

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.