Longboat Key Holiday Rentals

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Holiday Rentals in Longboat Key

THE BEACH CONDO #107 BEACHFRONT FULL VIEW

Longboat Key
9.8 out of 10, Exceptional, (80)
"Beautiful location and the beach is amazing "
United States
Heather A.
The price is NZ$674
includes taxes & fees
14 Dec - 15 Dec
THE BEACH CONDO #107 BEACHFRONT FULL VIEW

Sea Club I Beach Resort

3.0 star property
Longboat Key
9.2 out of 10, Wonderful, (335)
"Very nice beach themed bungalow. Loved the quiet and the views. "
United States
Jennifer
Sea Club I Beach Resort

Right on the beach.Renovated ground Floor unit 63.

Longboat Key
9.4 out of 10, Exceptional, (56)
"Excellent, clean, and friendly"
United States
John G.
The price is NZ$565
includes taxes & fees
28 Dec - 29 Dec
Right on the beach.Renovated ground Floor unit 63.

Now Open! 7-Night Deal – Oceanfront w/ Private Balcony & Stunning Views

Longboat Key
9.6 out of 10, Exceptional, (84)
"Great owners, fantastic beach. Hope to be back "
United States
John O.
Now Open! 7-Night Deal – Oceanfront w/ Private Balcony & Stunning Views

Charming 1-bedroom, beachfront condo in marvelous Longboat Key

Longboat Key
9.0 out of 10, Wonderful, (25)
"The property was great for our family, loved having a pool and beach access. Super simple especially with a toddler in tow."
United States
Cara
The price is NZ$827
includes taxes & fees
16 Dec - 17 Dec
Charming 1-bedroom, beachfront condo in marvelous Longboat Key

Flash sale 5-floor penthouse 60 feet from water, 150+ reviews

Longboat Key
10.0 out of 10, Exceptional, (203)
"Unit was exactly as advertised plus spotlessly clean. Owner was wonderful to communicate with. Felt like we were guests in his home. We’ve already reserved for next year. "
United States
Brian B.
Flash sale 5-floor penthouse 60 feet from water, 150+ reviews

Sunset and beach view from your balcony Unit 403

Longboat Key
9.8 out of 10, Exceptional, (107)
"Gorgeous view and comfortable interior. Great beach access and good pool. "
United States
Tanya M.
The price is NZ$678
includes taxes & fees
8 Dec - 9 Dec
Sunset and beach view from your balcony Unit 403

Luxury Beach Condo - Ocean View w/ Fireplace. 2br/2ba. Full Kitchen

Longboat Key
9.8 out of 10, Exceptional, (255)
"A very nice quite getaway with family. Right on the beach. The place was lovely and the owner was always there to answer any questions. Thank you Ann for a great Vacation!!"
United States
Michaela G.
Luxury Beach Condo - Ocean View w/ Fireplace. 2br/2ba. Full Kitchen

Sunset and Beach view unit 402

Longboat Key
9.8 out of 10, Exceptional, (13)
"Loved our stay. Margaret at the front desk was amazing. Hope to come back again soon. "
United States
slimetastic !.
The price is NZ$744
includes taxes & fees
18 Dec - 19 Dec
Sunset and Beach view unit 402

GULF FRONT CONDO / PRIVATE PATIO / STEPS TO THE BEACH

Longboat Key
9.8 out of 10, Exceptional, (105)
"This is our 4th year in this condo and we absolutely love it. Such a comfortable space and a perfect location. "
United States
Leilah S.
GULF FRONT CONDO / PRIVATE PATIO / STEPS TO THE BEACH

Oceanfront Oasis – Longboat Key 226 by RVA

Longboat Key
9.2 out of 10, Wonderful, (121)
"We had a beautiful trip, the Oceanfront Oais is phenomenal!"
United States
kata
The price is NZ$548
includes taxes & fees
13 Dec - 14 Dec
Oceanfront Oasis – Longboat Key 226 by RVA

Longboat Key, FL 2bd/2ba condo available! Steps to the beach!

Longboat Key
Longboat Key, FL 2bd/2ba condo available! Steps to the beach!

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

Longboat Key
9.8 out of 10, Exceptional, (154)
"Just as advertised, very nice location"
United States
Roxanne P.
Charming Cabana Beach Club #8 - Your Coastal retreat Awaits!#9 also available.

Flash Sale Late OCT - NOV take a peek

Longboat Key
10.0 out of 10, Exceptional, (136)
"We had a wonderful stay. Can’t say enough about the beautiful views! Would definitely come back!"
United States
Sharon H.
Flash Sale Late OCT - NOV take a peek

Best views of the beach from your balcony Unit 301

Longboat Key
9.8 out of 10, Exceptional, (88)
"It was so great loved everything in the home"
United States
TERRY C.
Best views of the beach from your balcony Unit 301

Client texted view crazy ON SALE

Longboat Key
10.0 out of 10, Exceptional, (96)
"Longboat Key is just beautiful and quiet. This condo has excellent access to the beach. We enjoyed our stay. "
United States
Nick S.
Client texted view crazy ON SALE

Longboat Bay Club by Coolvacay

3.5 star property
Longboat Key
10.0 out of 10, Exceptional, (1)
"Great property with beach access across the street! 2 br unit was huge as were the balconies. Our unit 105 was quite dated but still nice."
United States
Andrew
Longboat Bay Club by Coolvacay

Charming Beach Front Studio Steps to the Sand and Gulf

Longboat Key
9.8 out of 10, Exceptional, (21)
"A nice efficient place to stay."
United States
George B.
Charming Beach Front Studio Steps to the Sand and Gulf

Breathtaking Beach Front Property Ground Floor Condo

Longboat Key
9.6 out of 10, Exceptional, (152)
"This property was perfect for our sister trip! Location, property condition and communication was excellent! "
United States
Nora W.
Breathtaking Beach Front Property Ground Floor Condo

Wonderful Canal Front Condo! See Manatees Right From Your Doorstep!Cabana #10

Longboat Key
9.0 out of 10, Wonderful, (47)
"Once again we had a wonderful stay here. Great if you want to rent a boat and so peaceful!"
United States
Melanie M.
Wonderful Canal Front Condo! See Manatees Right From Your Doorstep!Cabana #10
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, 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 NZ$548 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 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 24 Expedia holiday rentals in Longboat Key for a memorable holiday.

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. Lido Beach and Siesta Key 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.