Holiday Rentals in Longboat Key

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Our top choices for Longboat Key holiday rentals

Renovated Beach Paradise. Ground Floor unit 64

Renovated Beach Paradise. Ground Floor unit 64
Longboat Key
9.8 out of 10, Exceptional, (67 reviews)
"Everything was perfect the location was amazing Very clean and welcoming "
United States
Brian M.
The price is €350
includes taxes & fees
28 May - 29 May
Renovated Beach Paradise. Ground Floor unit 64

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
9.8 out of 10, Exceptional, (103 reviews)
"Location and view was amazing "
United States
joseph l.
Client texted view crazy Last minute cancellation Apr 25 - May 16th on sale

Drift & Dune – Longboat Beachfront #101 RVA

Drift & Dune – Longboat Beachfront #101 RVA
Longboat Key
8.6 out of 10, Excellent, (80 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 €310
includes taxes & fees
26 May - 27 May
Drift & Dune – Longboat Beachfront #101 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
9.2 out of 10, Wonderful, (44 reviews)
"Great stay and very friendly staff and host."
United States
Ida A.
The price is €467
includes taxes & fees
25 May - 26 May
Beach front 2 bed-2 bath private balcony, modern with Gulf front views

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, (90 reviews)
"Everything was great "
United States
kirt v.
The price is €356
includes taxes & fees
6 Jun - 7 Jun
Best views of the beach from your balcony Unit 301

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, (268 reviews)
"Was very fun and we found sharks teeth on the beach. Everything was perfect i will be back "
United States
victor y.
The price is €573
includes taxes & fees
20 Jun - 21 Jun
Cabana Beach Club - Beachfront Stunning Ocean View *Snow Bird Promo* Winter 2027

1BR Beach Getaway – Silver Sands #254 by RVA

1BR Beach Getaway – Silver Sands #254 by RVA
Longboat Key
9.2 out of 10, Wonderful, (95 reviews)
"Great view, clean, beautiful!"
United States
Bethany
The price is €352
includes taxes & fees
28 May - 29 May
1BR Beach Getaway – Silver Sands #254 by RVA

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 €388
includes taxes & fees
15 Jun - 16 Jun
Island Time!

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)
"Great location, and it was a clean, updated, and comfortable stay!!"
United States
Brian B.
The price is €782
includes taxes & fees
26 May - 27 May
Updated Beachfront Condo at Prestigious Long Boat Key Resort

Bright Beach Studio – Silver Sands #255A by RVA

Bright Beach Studio – Silver Sands #255A by RVA
Longboat Key
8.8 out of 10, Excellent, (68 reviews)
"Perfect location and well-maintained unit - highly recommend!"
United States
Philip K.
The price is €287
includes taxes & fees
26 May - 27 May
Bright Beach Studio – Silver Sands #255A by RVA

Gulf Views – Silver Sands #250, Longboat Key by RVA

Gulf Views – Silver Sands #250, Longboat Key by RVA
Longboat Key
9.0 out of 10, Wonderful, (77 reviews)
"The host staff were very helpful."
United States
Ann S.
The price is €361
includes taxes & fees
27 May - 28 May
Gulf Views – Silver Sands #250, Longboat Key by RVA

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 €373
includes taxes & fees
18 Jun - 19 Jun
Sunset and beach view from your balcony Unit 403

Oceanfront Bliss–Longboat Key Beach 106 by RVA

Oceanfront Bliss–Longboat Key Beach 106 by RVA
Longboat Key
8.8 out of 10, Excellent, (98 reviews)
"Steps away from the beach. Clean place with Murphy Bed, but they had a foam topper in the closet. Nice chairs and umbrellas with nice beach and pool. Would stay again"
United States
Anonymous traveller
The price is €264
includes taxes & fees
24 May - 25 May
Oceanfront Bliss–Longboat Key Beach 106 by 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)
"Host was wondeful!Location and condo fabulous!"
United States
Linda D.
The price is €368
includes taxes & fees
25 May - 26 May
THE BEACH CONDO #107 BEACHFRONT FULL VIEW

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)
"We had the most wonderful stay despite the cold temps for most it! The staff at our location are above and beyond to make sure you have everything you need! Highly recommend!"
United States
Sahra S.
The price is €291
includes taxes & fees
25 May - 26 May
Ground Floor, Steps to Sand – Silver Sands #243A by RVA

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)
"Staff was welcoming- place was clean and stay was great"
United States
Joseph S.
The price is €333
includes taxes & fees
25 May - 26 May
Gulf Front Escape – Silver Sands #252 by RVA

Gulf Breezes & Poolside Peace – Silver Sands #236 by RVA

Gulf Breezes & Poolside Peace – Silver Sands #236 by RVA
Longboat Key
9.2 out of 10, Wonderful, (79 reviews)
"We had a pleasant stay with no issues. Pool was warm and beach was very nice with plenty of soft dry sand up top. They have lounge chairs for you to use in both of these areas."
United States
Mark R.
The price is €324
includes taxes & fees
31 May - 1 Jun
Gulf Breezes & Poolside Peace – Silver Sands #236 by RVA

Affordable Beach Studio – Silver Sands #257A by RVA

Affordable Beach Studio – Silver Sands #257A by RVA
Longboat Key
9.6 out of 10, Exceptional, (78 reviews)
"Right on beach-perfect for a short stay"
United States
Sean P.
The price is €279
includes taxes & fees
27 May - 28 May
Affordable Beach Studio – Silver Sands #257A by RVA

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.
Sun, Sand & Silver Sands – Gulfside Resort #237 by RVA

Beachside Studio – Silver Sands #253A, Longboat Key

Beachside Studio – Silver Sands #253A, Longboat Key
Longboat Key
8.4 out of 10, Very good, (38 reviews)
"I really enjoyed my stay at the Silver Sands and will recommend your property"
United States
Jeff H.
Beachside Studio – Silver Sands #253A, Longboat Key
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 €264 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 22 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.