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Longboat Key Holiday Rentals

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Our top choices for Longboat Key holiday rentals

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 NZ$712
includes taxes & fees
11 June - 12 June
Drift & Dune – Longboat Beachfront #101 RVA

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
1BR Beach Getaway – Silver Sands #254 by RVA

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, (91 reviews)
"Everything was great "
United States
kirt v.
The price is NZ$714
includes taxes & fees
12 June - 13 June
Best views of the beach from your balcony Unit 301

Beachfront Bliss: Beach Castle #1 by RVA

Beachfront Bliss: Beach Castle #1 by RVA
Longboat Key
9.0 out of 10, Wonderful, (48 reviews)
"Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was more than satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Loved the property and beach"
United States
Gary G.
The price is NZ$904
includes taxes & fees
21 June - 22 June
Beachfront Bliss: Beach Castle #1 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.
The price is NZ$881
includes taxes & fees
23 June - 24 June
Gulfside 2BR Condo–Silver Sands #257S

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 NZ$1,503
includes taxes & fees
16 June - 17 June
Updated Beachfront Condo at Prestigious Long Boat Key Resort

THE BEACH CONDO #107 BEACHFRONT FULL VIEW

THE BEACH CONDO #107 BEACHFRONT FULL VIEW
Longboat Key
9.8 out of 10, Exceptional, (94 reviews)
"Host was wondeful!Location and condo fabulous!"
United States
Linda D.
The price is NZ$783
includes taxes & fees
5 July - 6 July
THE BEACH CONDO #107 BEACHFRONT FULL VIEW

Pool & Beach Access – Silver Sands #241S by RVA

Pool & Beach Access – Silver Sands #241S by RVA
Longboat Key
9.0 out of 10, Wonderful, (19 reviews)
"Perfect location, good amenities, super retro vibe!"
United States
Christopher W.
The price is NZ$1,158
includes taxes & fees
21 June - 22 June
Pool & Beach Access – Silver Sands #241S by RVA

Gulf-View Beachfront Condo – Unit 203 – Longboat Key

Gulf-View Beachfront Condo – Unit 203 – Longboat Key
Longboat Key
Gulf-View Beachfront Condo – Unit 203 – Longboat Key

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)
"The unit has a perfect balcony view of the beach. The space was very clean and comfortable with many amenities including coolers and beach umbrellas. The property provides nice lounge chairs for the beach. The host Anna was quickly responsive to our questions and needs during our visit. Highly recommend this property !"
United States
Tracey s.
Cabana Beach Club - Beachfront Stunning Ocean View *Snow Bird Promo* Winter 2027

Affordable Beach Studio – Silver Sands #257A by RVA

Affordable Beach Studio – Silver Sands #257A by RVA
Longboat Key
9.6 out of 10, Exceptional, (79 reviews)
"Right on beach-perfect for a short stay"
United States
Sean P.
The price is NZ$564
includes taxes & fees
23 June - 24 June
Affordable Beach Studio – Silver Sands #257A by RVA

Island Time on LBK!

Island Time on LBK!
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 NZ$729
includes taxes & fees
26 June - 27 June
Island Time on LBK!

Seaside Escape – Beach Castle #24 by RVA

Seaside Escape – Beach Castle #24 by RVA
Longboat Key
9.2 out of 10, Wonderful, (49 reviews)
"Condo was clean, nicely decorated, comfy king bed and the property was charming and quiet.Appreciated the back deck and view of the bay.Also convenient to many restaurants and the beach.Also loved access to the club down the street."
United States
Jody B.
Seaside Escape – Beach Castle #24 by RVA

Beach Castle Bliss #22 by RVA

Beach Castle Bliss #22 by RVA
Longboat Key
9.6 out of 10, Exceptional, (46 reviews)
"Great place to stay"
United States
Michael W.
Beach Castle Bliss #22 by RVA

Oceanfront Oasis – Longboat Key 226 by RVA

Oceanfront Oasis – Longboat Key 226 by RVA
Longboat Key
9.2 out of 10, Wonderful, (132 reviews)
"Great beach!"
United States
Carolyn
The price is NZ$1,031
includes taxes & fees
24 June - 25 June
Oceanfront Oasis – Longboat Key 226 by RVA

Relax at Gulf – Silver Sands Resort #232, Longboat

Relax at Gulf – Silver Sands Resort #232, Longboat
Longboat Key
9.2 out of 10, Wonderful, (80 reviews)
"Very happy with my stay. Room was very clean, beautifully decorated and very comfortable. Perfect efficiency! Highly recommend"
United States
Gloria
The price is NZ$802
includes taxes & fees
12 June - 13 June
Relax at Gulf – Silver Sands Resort #232, Longboat

2BR Gulf View Condo Cabana Beach Club #7 by RVA

2BR Gulf View Condo Cabana Beach Club #7 by RVA
Longboat Key
9.6 out of 10, Exceptional, (76 reviews)
"It was a wonderful location "
United States
Kerri S.
The price is NZ$1,230
includes taxes & fees
5 July - 6 July
2BR Gulf View Condo Cabana Beach Club #7 by RVA

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

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 NZ$771
includes taxes & fees
15 June - 16 June
Ground Floor, Steps to Sand – Silver Sands #243A by RVA

Ocean Breeze: Open Tomorrow & Friday, $150/nt + Fees!

Ocean Breeze: Open Tomorrow & Friday, $150/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 NZ$866
includes taxes & fees
22 June - 23 June
Ocean Breeze: Open Tomorrow & Friday, $150/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, 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$603 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 24 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. 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.