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Our top choices for Longboat Key holiday rentals

Island Time!

Island Time!
Longboat Key
10.0 out of 10, Exceptional, (125 reviews)
"Great host! Amazing location. Loved the beach access and views! Highly recommended "
United States
Bonnie N.
The price is £313
includes taxes & fees
13 May - 14 May
Island Time!

Charming 1-bedroom, Beachfront condo in fabulous Longboat Key steps to the beach

Charming 1-bedroom, Beachfront condo in fabulous Longboat Key steps to the beach
Longboat Key
8.8 out of 10, Excellent, (21 reviews)
"It was in great condition and an overall good experience. "
United States
Ava G.
The price is £329
includes taxes & fees
11 May - 12 May
Charming 1-bedroom, Beachfront condo in fabulous Longboat Key steps to 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)
"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.
The price is £667
includes taxes & fees
18 May - 19 May
Updated Beachfront Condo at Prestigious Long Boat Key Resort

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.
The price is £285
includes taxes & fees
11 May - 12 May
Gulf Front Escape – Silver Sands #252 by RVA

Gulf Getaway – Beach Castle #12 by RVA

Gulf Getaway – Beach Castle #12 by RVA
Longboat Key
9.6 out of 10, Exceptional, (42 reviews)
"Very nice unit. Comfortable, clean, well equipped. Great location. "
United States
EUGENE O.
The price is £291
includes taxes & fees
7 May - 8 May
Gulf Getaway – Beach Castle #12 by RVA

Oceanfront Bliss–Longboat Key Beach 106 by RVA

Oceanfront Bliss–Longboat Key Beach 106 by RVA
Longboat Key
8.8 out of 10, Excellent, (97 reviews)
"Beautiful sunset view. "
United States
Rhonda V.
The price is £247
includes taxes & fees
16 May - 17 May
Oceanfront Bliss–Longboat Key Beach 106 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.
The price is £432
includes taxes & fees
28 May - 29 May
Gulfside 2BR Condo–Silver Sands #257S

Sandy Toes & Sun Kissed Nose!

Sandy Toes & Sun Kissed Nose!
Longboat Key
9.6 out of 10, Exceptional, (10 reviews)
"We had a wonderful stay, the condo was very well equipped and the host was absolutely fantastic! "
United States
Emily L.
The price is £313
includes taxes & fees
18 May - 19 May
Sandy Toes & Sun Kissed Nose!

Drift & Dune – Longboat Beachfront #101 RVA

Drift & Dune – Longboat Beachfront #101 RVA
Longboat Key
8.6 out of 10, Excellent, (79 reviews)
"Check in and out was easy, the pool and condo were great, and the location was awesome!"
United States
Bailey B.
The price is £239
includes taxes & fees
6 May - 7 May
Drift & Dune – Longboat Beachfront #101 RVA

THE BEACH CONDO #107 BEACHFRONT FULL VIEW

THE BEACH CONDO #107 BEACHFRONT FULL VIEW
Longboat Key
9.8 out of 10, Exceptional, (89 reviews)
"Incredible place. Already booked again!! "
United States
Julie T.
The price is £347
includes taxes & fees
10 May - 11 May
THE BEACH CONDO #107 BEACHFRONT FULL VIEW

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, (207 reviews)
"Great location."
United States
Janet B.
The price is £411
includes taxes & fees
10 May - 11 May
Are you ready for a luxury 5-floor penthouse 60 ft from water, 207 reviews

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, (80 reviews)
"Very nice place"
United States
Laurette C.
The price is £280
includes taxes & fees
11 May - 12 May
The Beach on Longboat Key #227 Resort 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)
"Would def stay here again!"
United States
Tammie and David
The price is £248
includes taxes & fees
13 May - 14 May
Ground Floor, Steps to Sand – Silver Sands #243A by RVA

Beachfront Bliss on Longboat Key- Steps to the sand

Beachfront Bliss on Longboat Key- Steps to the sand
Longboat Key
8.6 out of 10, Excellent, (17 reviews)
"Great locale right on the beach "
United States
Carole
The price is £304
includes taxes & fees
18 May - 19 May
Beachfront Bliss on Longboat Key- Steps to the sand

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, (42 reviews)
"Enjoyed our stay"
United States
Susan C.
The price is £255
includes taxes & fees
13 May - 14 May
Sun, Sand & Silver Sands – Gulfside Resort #237 by RVA

Client texted view crazy Last minute cancellation Apr 25 - May 16th on sale

Client texted view crazy Last minute cancellation Apr 25 - May 16th on sale
Longboat Key
10.0 out of 10, Exceptional, (101 reviews)
"Location and view was amazing "
United States
joseph l.
The price is £439
includes taxes & fees
19 May - 20 May
Client texted view crazy Last minute cancellation Apr 25 - May 16th on sale

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

Pool & Beach Access – Silver Sands #241S by RVA
Longboat Key
8.8 out of 10, Excellent, (18 reviews)
"Perfect location, good amenities, super retro vibe!"
United States
Christopher W.
The price is £368
includes taxes & fees
6 May - 7 May
Pool & Beach Access – Silver Sands #241S by RVA

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.
The price is £253
includes taxes & fees
13 May - 14 May
Gulfside Resort – Silver Sands #241A by RVA

1BR Beach Getaway – Silver Sands #254 by RVA

1BR Beach Getaway – Silver Sands #254 by RVA
Longboat Key
9.2 out of 10, Wonderful, (94 reviews)
"Great view, clean, beautiful!"
United States
Bethany
The price is £277
includes taxes & fees
11 May - 12 May
1BR Beach Getaway – Silver Sands #254 by RVA

Ocean Breeze: June & July Availability!

Ocean Breeze: June & July Availability!
Longboat Key
10.0 out of 10, Exceptional, (90 reviews)
"Great accommodations, excellent location, amazing host!"
United States
Ella F.
Ocean Breeze: June & July Availability!
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

Find out more about Longboat Key

Everything you need to know about Longboat Key holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Longboat Key holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Longboat Key holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Longboat Key holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Longboat Key holiday rentals we have selected for you start as low as £247 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Longboat Key rentals

At Expedia, we put the best Longboat Key holiday 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 holiday.

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 holiday rental in Longboat Key?

Yes, there are holiday rentals close to the most popular sights in Longboat Key, or you can select a more secluded option if you're looking for a relaxing stay. 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 holiday rentals that Longboat Key has to offer?

Siesta Key Island Rentals: This holiday home rental outside of Longboat Key comes with free WiFi so that you can feel at home during your trip. This holiday rental also comes with free parking to give you added peace of mind.

How many holiday rentals are there in Longboat Key?

Choose from 20 Expedia holiday rentals in Longboat Key for a memorable holiday.

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 holiday rentals like in Longboat Key?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Longboat Key. Holiday rentals offer extras like WiFi and washers and dryers so you'll have all the comforts of home. If you're concerned about a clean environment, holiday rentals can provide a sense of privacy away from public hotel lifts and bustling concierge desks while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a popular choice for a family trip.