Longboat Key Holiday Rentals

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Tonight
22 Jan - 23 Jan
Tomorrow
23 Jan - 24 Jan
This weekend
24 Jan - 26 Jan
Next weekend
31 Jan - 2 Feb

Holiday Rentals in Longboat Key

Beach view. Year-round Balcony Sunsets. Just renovated.
Property grounds

Beach view. Year-round Balcony Sunsets. Just renovated.

9.8 out of 10, Exceptional, (76)
"We spend every new years at this apartment and love it. Perfect location, in great condition, feet from the beach, and close to all kinds of restaurants, ice cream shops, and stores. Great communication from the owner and building management. Can't wait to go back!"
Beach view. Year-round Balcony Sunsets. Just renovated.
Sea Club I Beach Resort
On the beach, white sand

Sea Club I Beach Resort

3.0 star property
9.0 out of 10, Wonderful, (301)
"I love that this property is right on the beach. We were there over Christmas. The property was not fully booked, so it was fairly quiet. The Gulf was too cold for us, but we enjoyed using the the provided lounge chairs to relax on the beach. Lots of shelling to do. Not a lot of people at this time. Pool was not a bad temperature and was clean. The property looks like an old motor lodge, but they have kept it nice. Our room did not have a lot of updates, but it was sufficient. A roll of paper...
Sea Club I Beach Resort
Charming Cabana Beach Club #8 - Your Coastal retreat Awaits!#9 also available.
On the beach, sun-loungers, beach towels

Charming Cabana Beach Club #8 - Your Coastal retreat Awaits!#9 also available.

9.8 out of 10, Exceptional, (137)
"Cute little cottage with 2br, 1ba. Very clean, close to the beach. Lots of supplies for the beach. Could use softer towels in bathroom and perhaps some instructions on the shower as it was quite hot on any setting. Prior communication was slow but once there was pretty attentive. "
Charming Cabana Beach Club #8 - Your Coastal retreat Awaits!#9 also available.
Silver Sands #236 Resort by RVA
On the beach, beach umbrellas

Silver Sands #236 Resort by RVA

9.2 out of 10, Wonderful, (63)
"Great location, friendly staff, vrbo needs updated cooking pots/pans dishes, etc. Probably to be expected after the hurricane, but if open, then these need to be updated so people staying have the ability to eat in while there. Otherwise, great stay, all you need for the beach! "
Silver Sands #236 Resort by RVA
Longboat Key beach house - 5 min walk to the beaches and top local restaurants
Sun-loungers, beach towels

Longboat Key beach house - 5 min walk to the beaches and top local restaurants

9.6 out of 10, Exceptional, (13)
"The property looked exactly like the photos. It was clean, in a very quiet neighbourhood close to the beach & some good restaurants. Beds were comfortable. Kitchen could have done with more stock (there were 8 of us staying & not enough crockery or cutlery) but wasn’t a huge issue. We loved the location & how quiet it was, so would definitely stay again."
Longboat Key beach house - 5 min walk to the beaches and top local restaurants
Luxury Beach Condo with Breathtaking Views Upgraded! PROMO 2024 !!,
Exterior

Luxury Beach Condo with Breathtaking Views Upgraded! PROMO 2024 !!,

9.8 out of 10, Exceptional, (231)
"Very nice condo furnished with almost everything you would need. Great beach and sunset views. Near to nice restaurants, grocery store and St. Armands. Area at the time of our stay is still recovering from last summers hurricane, but slowly returning to one of our favorite areas to visit. We would definitely rent this unit again. "
Luxury Beach Condo with Breathtaking Views Upgraded! PROMO 2024 !!,
Breathtaking Beach Front Property Ground Floor Condo
On the beach

Breathtaking Beach Front Property Ground Floor Condo

9.6 out of 10, Exceptional, (131)
"The condo was perfect for a long weekend visiting my aunt on Longboat Key. The place was as expected, clean, kitchen supplied with necessary items, a deck just off the pool. Great staff with easy check in and out. I will stay here again "
Breathtaking Beach Front Property Ground Floor Condo
Waterfront home with private beach, a private pool, and water activities! Moku
On the beach

Waterfront home with private beach, a private pool, and water activities! Moku

10.0 out of 10, Exceptional, (2)
"We had a great stay! It was definitely an experience. It was a peaceful island getaway. If you are able to stay here I recommend it! Any issues we had the AMI team had a quick and efficient response-the only issues we had was our door code didn’t work for all the doors but they responded quickly and got us in in a blink of an eye, and the trash bins outside were almost full but they were out the next day to empty them so no complaints with that! Our only thing was the water in the house is VERY...
Waterfront home with private beach, a private pool, and water activities! Moku
Direct Beachfront Gulf with Amazing Views
On the beach, sun-loungers, beach towels

Direct Beachfront Gulf with Amazing Views

9.8 out of 10, Exceptional, (90)
"Beautiful location. Quiet, relaxing spot on beach with excellent sunsets every evening. The condo is comfortable and well appointed. "
Direct Beachfront Gulf with Amazing Views
Beautiful Beach Longboat Key Townhouse
Beach nearby, sun-loungers, beach towels

Beautiful Beach Longboat Key Townhouse

10.0 out of 10, Exceptional, (16)
"The condo was very cleaned and had everything you needed to have a comfortable stay. The kitchen was well stocked with things you may need to cook, beach towels, chairs, umbrellas, toys were provided. The communication with the owner was easy and he got back to me on a few questions promptly. Being at Cedars is great- there is access to a fitness center, pool, tennis, pickleball and bikes. It also has access to the bay. Overall, would recommend."
Beautiful Beach Longboat Key Townhouse
Oceanside Condo on LBK!
On the beach, sun-loungers, beach towels

Oceanside Condo on LBK!

10.0 out of 10, Exceptional, (65)
"The condo was perfect for us. Heidi is by far the best host we’ve ever stayed with!! She has thought of everything one might need. It’s just a few steps down to the beach - which was wonderful! Brought home some pretty shells. We will stay here again!!"
The price is HK$2,326
HK$4,246 total
includes taxes & fees
29 Jan - 30 Jan
Oceanside Condo on LBK!
Beach View Condo- Quiet & Secluded with Private Beach
On the beach, sun-loungers, beach towels

Beach View Condo- Quiet & Secluded with Private Beach

10.0 out of 10, Exceptional, (22)
"Cannot be more happy with our 6 day stay. The area is close to restaurants (Harry’s for the win), is perfectly situated on the beach where you avoid the crowds, and Danielle was so wonderful at making sure we had everything set for the visit. Will be back for sure!!"
Beach View Condo- Quiet & Secluded with Private Beach
Panoramic beach View and amazing Sunset.
Property grounds

Panoramic beach View and amazing Sunset.

9.8 out of 10, Exceptional, (96)
"Great location and clean."
The price is HK$2,529
HK$4,705 total
includes taxes & fees
2 Feb - 3 Feb
Panoramic beach View and amazing Sunset.
THE BEACH, condo #107, Grounds under repair
Sun-loungers, beach towels

THE BEACH, condo #107, Grounds under repair

9.8 out of 10, Exceptional, (60)
"Very nice "
The price is HK$973
HK$2,324 total
includes taxes & fees
28 Jan - 29 Jan
THE BEACH, condo #107, Grounds under repair
Updated Beachfront Condo at Prestigious Long Boat Key Resort
A heated pool

Updated Beachfront Condo at Prestigious Long Boat Key Resort

8.6 out of 10, Excellent, (11)
"Secluded property in a gated community. Beach and ocean views tremendous. Loved sitting on the balcony (which is twice as long as the picture) and drinking coffee while relaxing in the morning."
The price is HK$4,010
HK$7,834 total
includes taxes & fees
23 Jan - 24 Jan
Updated Beachfront Condo at Prestigious Long Boat Key Resort
The Beach on Longboat Key #220 Resort by RVA
On the beach

The Beach on Longboat Key #220 Resort by RVA

8.0 out of 10, Very good, (42)
"We enjoyed our stay! We had all the necessaries for a few days at the beach. It’s a great price point if you’re just looking for a little rest on the beach. There are local restaurants just a few miles down the road. The only think I would suggest is that the property provide a broom for the room. You’re at the beach so of course, there is going to be sand. We are planning on coming back. "
The Beach on Longboat Key #220 Resort by RVA
Gulf Getaway with Porch + Direct Beach Access!
Beach nearby

Gulf Getaway with Porch + Direct Beach Access!

9.2 out of 10, Wonderful, (35)
"We had an awesome time at Longboat Key. It’s our favorite place and this was a perfect location to the beach, and the shops at St. Armand’s Circle. We will def book again and again!"
Gulf Getaway with Porch + Direct Beach Access!
Beachfront With Incredible Panoramic Gulf View and The Most Beautiful Sunset.
On the beach, sun-loungers, beach towels

Beachfront With Incredible Panoramic Gulf View and The Most Beautiful Sunset.

9.8 out of 10, Exceptional, (129)
"This condo was very impressive. Everything was clean and well maintained. The staff was very engaging. But the sunsets were spectacular. We were right on the ocean!"
The price is HK$1,206
HK$2,977 total
includes taxes & fees
25 Jan - 26 Jan
Beachfront With Incredible Panoramic Gulf View and The Most Beautiful Sunset.
Silver Sands #237 Resort by RVA
On the beach, beach umbrellas

Silver Sands #237 Resort by RVA

9.0 out of 10, Wonderful, (38)
"Steps to the beach and included towels, beach chairs and umbrellas. Staff was extremely nice and we enjoyed the joke of the day while checking in!"
Silver Sands #237 Resort by RVA
Beach Front No Crossing Needed One Bedroom Condo. Fully Renovated. Ground Floor.
On the beach, sun-loungers, beach towels

Beach Front No Crossing Needed One Bedroom Condo. Fully Renovated. Ground Floor.

9.8 out of 10, Exceptional, (55)
"Great location, beautiful beaches, and very nice unit. Beautiful grounds and easy access to the beach. We also enjoyed the heated pool! "
The price is HK$1,004
HK$2,743 total
includes taxes & fees
12 Feb - 13 Feb
Beach Front No Crossing Needed One Bedroom Condo. Fully Renovated. Ground Floor.
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.
Don't see what you're looking for?
See all available properties in Longboat Key
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other types of properties in Longboat Key you may be interested in

Zota Beach Resort
Breakfast, lunch and dinner served

Zota Beach Resort

4.0 star property
9.0 out of 10, Wonderful, (1000)
"Zota resort exceeded our expectations with excellent service, spacious room, luxurious bedding and toiletries, direct access to a great beach."
The price is HK$2,328
HK$2,979 total
includes taxes & fees
23 Jan - 24 Jan
Zota Beach Resort
The St. Regis Longboat Key Resort
View from property

The St. Regis Longboat Key Resort

5.0 star property
10.0 out of 10, Exceptional, (10)
"Loved it"
The price is HK$8,784
HK$10,410 total
includes taxes & fees
11 Feb - 12 Feb
The St. Regis Longboat Key Resort
The Resort at Longboat Key Club
Exterior

The Resort at Longboat Key Club

4.0 star property
9.0 out of 10, Wonderful, (639)
"Staff excellent. Elevators need work. Rooms very nice. Beach excellent "
The price is HK$4,158
HK$5,050 total
includes taxes & fees
23 Jan - 24 Jan
The Resort at Longboat Key Club
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.

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?

JAN. SPECIALS Beachfront, PRIVATE BEACH ON THE WATERFRONT, Bring your dog: This holiday home rental outside of Longboat Key is located on the beach, and has a balcony, a selection of games and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as 1 hot tub.

How many holiday rentals are there in Longboat Key?

Choose from 176 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. Other places in town to visit include Cannons Marina and Harborside Golf Course at Longboat Key Club.

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.