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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, (115 reviews)
"TCI is a great place to stay. Close to the beach, grocery store, shopping and walking paths. The condo was very clean and has all the amenities needed. The staff if very approachable and easy to connect with for any questions. This is our 2nd stay and we will return."
United States
Anonymous traveller
Sunset and beach view from your balcony Unit 403

Luxurious Beachfront Jr. Suite by FVC

Luxurious Beachfront Jr. Suite by FVC
Longboat Key
9.4 out of 10, Exceptional, (80 reviews)
"The space was exactly as described, beautiful, comfortable, right on the beach with excellent balcony space. The kitchen has everything you need and the area is really amazing!"
United States
Debra J.
Luxurious Beachfront Jr. Suite by FVC

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, (33 reviews)
"Extremely convenient access to beach, Large pool, putting green, and pool toys made our stay very fun. "
United States
Maria
The price is £400
includes taxes & fees
24 Jun - 25 Jun
Steps to Beach – Silver Sands 2BR Condo #243S by RVA

The Beach on Longboat Key #227 Resort by RVA

The Beach on Longboat Key #227 Resort by RVA
Longboat Key
9.2 out of 10, Wonderful, (81 reviews)
"Great location and great views!"
United States
Mark H.
The Beach on Longboat Key #227 Resort 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, (102 reviews)
"Beautiful sunset view. "
United States
Rhonda V.
The price is £233
includes taxes & fees
21 Jun - 22 Jun
Oceanfront Bliss–Longboat Key Beach 106 by RVA

Island Time: Open July 7 - 10!

Island Time: Open July 7 - 10!
Longboat Key
10.0 out of 10, Exceptional, (127 reviews)
"Great host! Amazing location. Loved the beach access and views! Highly recommended "
United States
Bonnie N.
The price is £341
includes taxes & fees
19 Jul - 20 Jul
Island Time: Open July 7 - 10!

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)
"Great location for the price! Also, it was well equipped with everything you need."
United States
LJ G.
The price is £503
includes taxes & fees
13 Jul - 14 Jul
Cabana Beach Club - Beachfront Stunning Ocean View *Snow Bird Promo* Winter 2027

THE BEACH CONDO #107 BEACHFRONT FULL VIEW

THE BEACH CONDO #107 BEACHFRONT FULL VIEW
Longboat Key
10.0 out of 10, Exceptional, (92 reviews)
"Host was wondeful!Location and condo fabulous!"
United States
Linda D.
The price is £347
includes taxes & fees
23 Jun - 24 Jun
THE BEACH CONDO #107 BEACHFRONT FULL VIEW

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 £284
includes taxes & fees
21 Jun - 22 Jun
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)
"Great location, and it was a clean, updated, and comfortable stay!!"
United States
Brian B.
The price is £566
includes taxes & fees
28 Jun - 29 Jun
Updated Beachfront Condo at Prestigious Long Boat Key Resort

Drift & Dune – Longboat Beachfront #101 RVA

Drift & Dune – Longboat Beachfront #101 RVA
Longboat Key
8.6 out of 10, Excellent, (81 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 £498
includes taxes & fees
30 Jun - 1 Jul
Drift & Dune – Longboat Beachfront #101 RVA

Take a peek awesome reviews 50 feet from sand

Take a peek awesome reviews 50 feet from sand
Longboat Key
10.0 out of 10, Exceptional, (147 reviews)
"A very considerate and available host! The condo was everything we could have wanted. Great location! Will return"
United States
Kathleen R.
Take a peek awesome reviews 50 feet from sand

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, (63 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 £256
includes taxes & fees
19 Jul - 20 Jul
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, (104 reviews)
"Staff was welcoming- place was clean and stay was great"
United States
Joseph S.
The price is £292
includes taxes & fees
21 Jun - 22 Jun
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, (81 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 £264
includes taxes & fees
24 Jun - 25 Jun
Gulf Breezes & Poolside Peace – Silver Sands #236 by RVA

Beachfront- Longboat Key efficiency condo w/ king size bed, steps to sand.

Beachfront- Longboat Key efficiency condo w/ king size bed, steps to sand.
Longboat Key
8.4 out of 10, Very good, (19 reviews)
"Excellent place to stay. "
United States
Hadley R.
The price is £270
includes taxes & fees
5 Jul - 6 Jul
Beachfront- Longboat Key efficiency condo w/ king size bed, steps to sand.

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)
"Beach is beautiful, location is great. Room was clean. Rhe bed"
United States
Kellie B.
The price is £261
includes taxes & fees
21 Jun - 22 Jun
Gulfside Resort – Silver Sands #241A by RVA

Step from the Beach.Renovated ground Floor unit 63

Step from the Beach.Renovated ground Floor unit 63
Longboat Key
9.4 out of 10, Exceptional, (72 reviews)
"Our stay was excellent. Nice and clean and plenty of room however it doesn’t have a beach view, but the beach is a very short, easy walk. Staff was extra nice, especially Margaret."
United States
Faye
Step from the Beach.Renovated ground Floor unit 63

50 ft from sand, Private Island 125 +review

50 ft from sand, Private Island 125 +review
Longboat Key
10.0 out of 10, Exceptional, (134 reviews)
"Jim is a great host - he is great at communicating before, during, and at the end of the stay. The condo we stayed in was exactly as described and was wonderful!!"
United States
Robin G.
The price is £450
includes taxes & fees
21 Jun - 22 Jun
50 ft from sand, Private Island 125 +review

Vitamin Sea: Open Tuesday, $199/nt + Fees!

Vitamin Sea: Open Tuesday, $199/nt + Fees!
Longboat Key
10.0 out of 10, Exceptional, (93 reviews)
"Great accommodations, excellent location, amazing host!"
United States
Ella F.
The price is £317
includes taxes & fees
23 Jun - 24 Jun
Vitamin Sea: Open Tuesday, $199/nt + Fees!
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 £245 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. 

Explore a world of travel with Expedia

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 23 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 Coquina 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.