Longboat Key Holiday Rentals

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Our top choices for Longboat Key holiday rentals

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.
The price is NZ$706
includes taxes & fees
28 Apr - 29 Apr
Sunset and beach view from your balcony Unit 403

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 NZ$1,485
includes taxes & fees
27 Apr - 28 Apr
Updated Beachfront Condo at Prestigious Long Boat Key Resort

Island Time!

Island Time!
Longboat Key
10.0 out of 10, Exceptional, (123 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
The price is NZ$743
includes taxes & fees
3 May - 4 May
Island Time!

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 NZ$621
includes taxes & fees
29 Apr - 30 Apr
Drift & Dune – Longboat Beachfront #101 RVA

Silver Sands 1BR – Gulfside Comfort #255 by RVA

Silver Sands 1BR – Gulfside Comfort #255 by RVA
Longboat Key
9.0 out of 10, Wonderful, (86 reviews)
"Location #1. Clean #2"
United States
Eric C.
The price is NZ$636
includes taxes & fees
28 Apr - 29 Apr
Silver Sands 1BR – Gulfside Comfort #255 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 NZ$581
includes taxes & fees
10 May - 11 May
Gulfside Resort – Silver Sands #241A 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, (96 reviews)
"Beautiful sunset view. "
United States
Rhonda V.
The price is NZ$507
includes taxes & fees
30 Apr - 1 May
Oceanfront Bliss–Longboat Key Beach 106 by RVA

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, (41 reviews)
"Small 2 story property right on the beach! The condo was clean and nicely laid out with room for the 3 of us. You can't beat the direct beach access and the shelling was great!"
United States
Jody S.
The price is NZ$898
includes taxes & fees
13 May - 14 May
Beach front 2 bed-2 bath private balcony, modern with Gulf front views

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, (32 reviews)
"Extremely convenient access to beach, Large pool, putting green, and pool toys made our stay very fun. "
United States
Maria
The price is NZ$894
includes taxes & fees
4 May - 5 May
Steps to Beach – Silver Sands 2BR Condo #243S by RVA

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 NZ$1,010
includes taxes & fees
9 May - 10 May
Are you ready for a luxury 5-floor penthouse 60 ft from water, 207 reviews

Cozy 1-bedroom apartment in delightful Longboat Key with AC

Cozy 1-bedroom apartment in delightful Longboat Key with AC
Longboat Key
Cozy 1-bedroom apartment in delightful Longboat Key with AC

Beachfront Studio – Cabana #5B by RVA

Beachfront Studio – Cabana #5B by RVA
Longboat Key
8.2 out of 10, Very good, (77 reviews)
"The pool was disgusting, dirt and debris on the bottom and top so that was disappointing, while watching TV and sleeping a person actually opened up our porch door then the main door and just walked in and said they had booked the same room and had keys, what kind of place does not keep track of that and I'm not sure what the person was thinking the TV was on and it was up a little so I know they heard it from the outside but to get back to that place for allowing that to happen. He's lucky I...
United States
Joseph
The price is NZ$524
includes taxes & fees
9 May - 10 May
Beachfront Studio – Cabana #5B 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, (78 reviews)
"Very nice place"
United States
Laurette C.
The price is NZ$641
includes taxes & fees
4 May - 5 May
The Beach on Longboat Key #227 Resort by RVA

Ocean Breeze, Mind at Ease!

Ocean Breeze, Mind at Ease!
Longboat Key
10.0 out of 10, Exceptional, (89 reviews)
"Great accommodations, excellent location, amazing host!"
United States
Ella F.
The price is NZ$686
includes taxes & fees
30 Apr - 1 May
Ocean Breeze, Mind at Ease!

Renovated Beach Paradise. Ground Floor unit 64

Renovated Beach Paradise. Ground Floor unit 64
Longboat Key
9.8 out of 10, Exceptional, (66 reviews)
"Everything was perfect the location was amazing Very clean and welcoming "
United States
Brian M.
The price is NZ$623
includes taxes & fees
28 Apr - 29 Apr
Renovated Beach Paradise. Ground Floor unit 64

THE BEACH CONDO #107 BEACHFRONT FULL VIEW

THE BEACH CONDO #107 BEACHFRONT FULL VIEW
Longboat Key
9.8 out of 10, Exceptional, (87 reviews)
"Incredible place. Already booked again!! "
United States
Julie T.
The price is NZ$764
includes taxes & fees
29 Apr - 30 Apr
THE BEACH CONDO #107 BEACHFRONT FULL VIEW

Relax at Gulf – Silver Sands Resort #232, Longboat

Relax at Gulf – Silver Sands Resort #232, Longboat
Longboat Key
9.2 out of 10, Wonderful, (79 reviews)
"Great beach access. Central location on the island. Not overcrowded. Ground floor unit was in good shape considering the hurricane in 2024.Bedroom could use blackout curtains (it gets bright in there in the AM) and the road noise was a bit loud."
United States
Mark G.
The price is NZ$558
includes taxes & fees
27 Apr - 28 Apr
Relax at Gulf – Silver Sands Resort #232, Longboat

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 NZ$600
includes taxes & fees
27 Apr - 28 Apr
Gulf Front Escape – Silver Sands #252 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, (100 reviews)
"Location and view was amazing "
United States
joseph l.
Client texted view crazy Last minute cancellation Apr 25 - May 16th on sale

Affordable Beach Studio – Silver Sands #257A by RVA

Affordable Beach Studio – Silver Sands #257A by RVA
Longboat Key
9.6 out of 10, Exceptional, (76 reviews)
"Right on beach-perfect for a short stay"
United States
Sean P.
The price is NZ$547
includes taxes & fees
10 May - 11 May
Affordable Beach Studio – Silver Sands #257A 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

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$507 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 18 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.