Longboat Key Vacation Rentals

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Our top choices for Longboat Key vacation rentals

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
9.0 out of 10, Wonderful, (40 reviews)
"Great stay and very friendly staff and host."
United States
Ida A.
Beach front 2 bed-2 bath private balcony, modern with Gulf front views

Sea Grape Inn #2- Beachfront Property

Sea Grape Inn #2- Beachfront Property
Longboat Key
10.0 out of 10, Exceptional, (15 reviews)
"The location was amazing with beach front property. Strongly recommend this resort. Frankie g "
United States
Frank
Sea Grape Inn #2- Beachfront Property

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, (263 reviews)
"Was very fun and we found sharks teeth on the beach. Everything was perfect i will be back "
United States
victor y.
$623 nightly
The price is $695
Apr 11 - Apr 12
Total with taxes and fees
Cabana Beach Club - Beachfront Stunning Ocean View *Snow Bird Promo* Winter 2027

1 Week left April 18 of a kind home right on the beach then booked till July

1 Week left April 18 of a kind home right on the beach then booked till July
Longboat Key
10.0 out of 10, Exceptional, (120 reviews)
"We loved our stay at the villa! The owner was always available to assist with any questions and allowed for a late check out as well. The house was well equipped. We all LOVED the location- right on the beach!"
United States
Brandy W.
$810 nightly
The price is $902
Apr 18 - Apr 19
Total with taxes and fees
1 Week left April 18 of a kind home right on the beach then booked till July

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.
$388 nightly
The price is $428
Apr 21 - Apr 22
Total with taxes and fees
Sunset and beach view from your balcony Unit 403

Vitamin Sea Escape: Open Sunday & Tuesday!

Vitamin Sea Escape: Open Sunday & Tuesday!
Longboat Key
10.0 out of 10, Exceptional, (88 reviews)
"Great accommodations, excellent location, amazing host!"
United States
Ella F.
$378 nightly
The price is $422
Apr 22 - Apr 23
Total with taxes and fees
Vitamin Sea Escape: Open Sunday & Tuesday!

Sun-Kissed Memories!

Sun-Kissed Memories!
Longboat Key
10.0 out of 10, Exceptional, (121 reviews)
"Great hostess, very thoughtful and kind. She thought of everything, we didn’t have to leave the premises. The location is unbelievable and the condo is gorgeous. We will definitely stay again!!"
United States
Amy K
$378 nightly
The price is $422
Apr 26 - Apr 27
Total with taxes and fees
Sun-Kissed Memories!

1BR Beach Getaway – Silver Sands #254 by RVA

1BR Beach Getaway – Silver Sands #254 by RVA
Longboat Key
9.2 out of 10, Wonderful, (93 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: Will stay here again"
United States
Chrissy C.
$356 nightly
The price is $398
May 7 - May 8
Total with taxes and fees
1BR Beach Getaway – Silver Sands #254 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)
"Perfect view, super clean, convenient, was the perfect size for me and my husband. We stayed for our 10 year anniversary and everything was perfect. "
United States
HALEY B.
$795 nightly
The price is $886
Apr 12 - Apr 13
Total with taxes and fees
Updated Beachfront Condo at Prestigious Long Boat Key Resort

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, (89 reviews)
"Breathtaking view- super clean. Easy access. Perfect spot for a few days away with my husband."
United States
Ellen L.
$380 nightly
The price is $418
Apr 30 - May 1
Total with taxes and fees
Best views of the beach from your balcony Unit 301

Direct Beach Access – Silver Sands #249 by RVA

Direct Beach Access – Silver Sands #249 by RVA
Longboat Key
9.2 out of 10, Wonderful, (60 reviews)
"Perfect location "
United States
Rachel H.
$558 nightly
The price is $622
Apr 10 - Apr 11
Total with taxes and fees
Direct Beach Access – Silver Sands #249 by RVA

Gulfside Comfort – Beach Castle #4 by RVA

Gulfside Comfort – Beach Castle #4 by RVA
Longboat Key
9.0 out of 10, Wonderful, (44 reviews)
"Everything was great, would definitely stay again!"
United States
Shelly V.
$460 nightly
The price is $513
Apr 12 - Apr 13
Total with taxes and fees
Gulfside Comfort – Beach Castle #4 by RVA

Silver Sands #245S Resort by RVA

Silver Sands #245S Resort by RVA
Longboat Key
9.0 out of 10, Wonderful, (29 reviews)
"This place has an old Florida vibe. It was a great place to enjoy a weekend with friends. The condo had everything we needed and easy walk to the beach. We saw some beautiful sunsets."
United States
Janet S.
$538 nightly
The price is $601
May 9 - May 10
Total with taxes and fees
Silver Sands #245S Resort by RVA

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.
$528 nightly
The price is $588
Apr 17 - Apr 18
Total with taxes and fees
Gulfside 2BR Condo–Silver Sands #257S

Relax at Gulf – Silver Sands Resort #232, Longboat

Relax at Gulf – Silver Sands Resort #232, Longboat
Longboat Key
9.2 out of 10, Wonderful, (78 reviews)
"Was good. Decent place to work remotely. Open to better rate in the future to stay for a month."
United States
Dan S.
$314 nightly
The price is $351
Apr 13 - Apr 14
Total with taxes and fees
Relax at Gulf – Silver Sands Resort #232, Longboat

Beachfront Studio – Cabana #5B by RVA

Beachfront Studio – Cabana #5B by RVA
Longboat Key
8.2 out of 10, Very Good, (76 reviews)
"Very nice place, clean and quiet. Staff very accommodating and professional. Definitely 5 star. "
United States
K M.
$274 nightly
The price is $306
Apr 23 - Apr 24
Total with taxes and fees
Beachfront Studio – Cabana #5B by RVA

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)
"Clean, cozy and right in the beach!! Was a perfect little getaway! "
United States
Michelle M.
$301 nightly
The price is $336
Apr 16 - Apr 17
Total with taxes and fees
Ground Floor, Steps to Sand – Silver Sands #243A by RVA

THE BEACH CONDO #107 BEACHFRONT FULL VIEW

THE BEACH CONDO #107 BEACHFRONT FULL VIEW
Longboat Key
10.0 out of 10, Exceptional, (86 reviews)
"Incredible place. Already booked again!! "
United States
Julie T.
$408 nightly
The price is $454
Apr 29 - Apr 30
Total with taxes and fees
THE BEACH CONDO #107 BEACHFRONT FULL VIEW

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)
"Perfect for our family "
United States
Alan B.
$347 nightly
The price is $386
Apr 27 - Apr 28
Total with taxes and fees
Gulf Front Escape – Silver Sands #252 by RVA

The Beach on Longboat Key #227 Resort by RVA

The Beach on Longboat Key #227 Resort by RVA
Longboat Key
9.0 out of 10, Wonderful, (76 reviews)
"The area and condo was perfect. The property was clean and well maintained. Highly recommended!"
United States
Fidel
$371 nightly
The price is $413
Apr 30 - May 1
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
This month
Next month
September
March
$416
$425
Month
Price
January
$445
February
$559
March
$635
April
$416
May
$425
June
$493
July
$488
August
$432
September
$389
October
$399
November
$416
December
$442
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 $332 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 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 20 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.