Holiday Rentals in Longboat Key

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Our top choices for Longboat Key holiday rentals

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, (39 reviews)
"Great stay and very friendly staff and host."
United States
Ida A.
Beach front 2 bed-2 bath private balcony, modern with Gulf front views

Sea Grape Inn #2- Beachfront Property

Sea Grape Inn #2- Beachfront Property
Longboat Key
10.0 out of 10, Exceptional, (15 reviews)
"The location was amazing with beach front property. Strongly recommend this resort. Frankie g "
United States
Frank
Sea Grape Inn #2- Beachfront Property

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, (263 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 €606
includes taxes & fees
11 Apr - 12 Apr
Cabana Beach Club - Beachfront Stunning Ocean View *Snow Bird Promo* Winter 2027

1 Week left April 18 of a kind home right on the beach then booked till July

1 Week left April 18 of a kind home right on the beach then booked till July
Longboat Key
10.0 out of 10, Exceptional, (120 reviews)
"We loved our stay at the villa! The owner was always available to assist with any questions and allowed for a late check out as well. The house was well equipped. We all LOVED the location- right on the beach!"
United States
Brandy W.
The price is €779
includes taxes & fees
18 Apr - 19 Apr
1 Week left April 18 of a kind home right on the beach then booked till July

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 €367
includes taxes & fees
21 Apr - 22 Apr
Sunset and beach view from your balcony Unit 403

Vitamin Sea Escape: Open April 12th - 15th!

Vitamin Sea Escape: Open April 12th - 15th!
Longboat Key
10.0 out of 10, Exceptional, (88 reviews)
"Great accommodations, excellent location, amazing host!"
United States
Ella F.
Vitamin Sea Escape: Open April 12th - 15th!

Sun-Kissed Memories!

Sun-Kissed Memories!
Longboat Key
10.0 out of 10, Exceptional, (121 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 €367
includes taxes & fees
26 Apr - 27 Apr
Sun-Kissed Memories!

1BR Beach Getaway – Silver Sands #254 by RVA

1BR Beach Getaway – Silver Sands #254 by RVA
Longboat Key
9.2 out of 10, Wonderful, (93 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: Will stay here again"
United States
Chrissy C.
The price is €349
includes taxes & fees
7 May - 8 May
1BR Beach Getaway – Silver Sands #254 by RVA

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 €784
includes taxes & fees
12 Apr - 13 Apr
Updated Beachfront Condo at Prestigious Long Boat Key Resort

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, (89 reviews)
"Breathtaking view- super clean. Easy access. Perfect spot for a few days away with my husband."
United States
Ellen L.
The price is €358
includes taxes & fees
30 Apr - 1 May
Best views of the beach from your balcony Unit 301

Direct Beach Access – Silver Sands #249 by RVA

Direct Beach Access – Silver Sands #249 by RVA
Longboat Key
9.2 out of 10, Wonderful, (60 reviews)
"Perfect location "
United States
Rachel H.
The price is €539
includes taxes & fees
10 Apr - 11 Apr
Direct Beach Access – Silver Sands #249 by RVA

Gulfside Comfort – Beach Castle #4 by RVA

Gulfside Comfort – Beach Castle #4 by RVA
Longboat Key
9.0 out of 10, Wonderful, (44 reviews)
"Everything was great, would definitely stay again!"
United States
Shelly V.
Gulfside Comfort – Beach Castle #4 by RVA

Silver Sands #245S Resort by RVA

Silver Sands #245S Resort by RVA
Longboat Key
9.0 out of 10, Wonderful, (29 reviews)
"This place has an old Florida vibe. It was a great place to enjoy a weekend with friends. The condo had everything we needed and easy walk to the beach. We saw some beautiful sunsets."
United States
Janet S.
The price is €474
includes taxes & fees
8 Apr - 9 Apr
Silver Sands #245S Resort 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.
Gulfside 2BR Condo–Silver Sands #257S

Relax at Gulf – Silver Sands Resort #232, Longboat

Relax at Gulf – Silver Sands Resort #232, Longboat
Longboat Key
9.2 out of 10, Wonderful, (78 reviews)
"Was good. Decent place to work remotely. Open to better rate in the future to stay for a month."
United States
Dan S.
The price is €307
includes taxes & fees
13 Apr - 14 Apr
Relax at Gulf – Silver Sands Resort #232, Longboat

Beachfront Studio – Cabana #5B by RVA

Beachfront Studio – Cabana #5B by RVA
Longboat Key
8.2 out of 10, Very good, (76 reviews)
"Very nice place, clean and quiet. Staff very accommodating and professional. Definitely 5 star. "
United States
K M.
The price is €270
includes taxes & fees
23 Apr - 24 Apr
Beachfront Studio – Cabana #5B 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)
"Clean, cozy and right in the beach!! Was a perfect little getaway! "
United States
Michelle M.
The price is €291
includes taxes & fees
20 Apr - 21 Apr
Ground Floor, Steps to Sand – Silver Sands #243A by RVA

THE BEACH CONDO #107 BEACHFRONT FULL VIEW

THE BEACH CONDO #107 BEACHFRONT FULL VIEW
Longboat Key
10.0 out of 10, Exceptional, (86 reviews)
"Incredible place. Already booked again!! "
United States
Julie T.
The price is €387
includes taxes & fees
29 Apr - 30 Apr
THE BEACH CONDO #107 BEACHFRONT FULL VIEW

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.
Gulf Front Escape – Silver Sands #252 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, (76 reviews)
"The area and condo was perfect. The property was clean and well maintained. Highly recommended!"
United States
Fidel
The Beach on Longboat Key #227 Resort 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, 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 €305 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.