Longboat Key Vacation Rentals

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Check prices for these dates

In two weeks
Jun 12 - Jun 14
In two months
Jul 24 - Jul 26
In three months
Aug 21 - Aug 23
In four months
Sep 18 - Sep 20

Our top choices for Longboat Key vacation rentals

On the beach

2 Bedroom Beachfront Condo by FVC

2 Bedroom Beachfront Condo by FVC
Longboat Key
9.6 out of 10, Exceptional, (45 reviews)
"Beautiful property with oversized balcony terrific for watching sunsets. Sandy beach was wonderful as was the pool. Property manager (FVC) was great to work with. Definitely recommend. "
United States
Daniel M.
The price is ￥76,338
￥167,570 total
includes taxes & fees
Jun 6 - Jun 7
2 Bedroom Beachfront Condo by FVC
On the beach, beach umbrellas

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 ￥39,656
￥85,055 total
includes taxes & fees
Jun 2 - Jun 3
Pool & Beach Access – Silver Sands #241S by RVA
On the beach

Unwind by the Waves – Beach Castle #5 by RVA

Unwind by the Waves – Beach Castle #5 by RVA
Longboat Key
9.0 out of 10, Wonderful, (38 reviews)
"Great location and very clean. "
United States
Kenneth E.
Unwind by the Waves – Beach Castle #5 by RVA
On the beach

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 ￥28,508
￥63,171 total
includes taxes & fees
Jun 2 - Jun 3
Drift & Dune – Longboat Beachfront #101 RVA
On the beach, beach umbrellas

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 ￥39,496
￥85,817 total
includes taxes & fees
Jun 4 - Jun 5
Steps to Beach – Silver Sands 2BR Condo #243S by RVA
On the beach

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 ￥47,778
￥86,199 total
includes taxes & fees
Jun 16 - Jun 17
Beach front 2 bed-2 bath private balcony, modern with Gulf front views
Property grounds

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 had everything we could possibly want. Everything to prepare wonderful meals and ability to grill and eat outdoors. Great location, clean unit, wonderful host who went the extra mile. "
United States
Mary L.
The price is ￥48,176
￥104,702 total
includes taxes & fees
Jun 20 - Jun 21
Cabana Beach Club - Beachfront Stunning Ocean View *Snow Bird Promo* Winter 2027
Outdoor dining

Island Time!

Island Time!
Longboat Key
10.0 out of 10, Exceptional, (126 reviews)
"Great host! Amazing location. Loved the beach access and views! Highly recommended "
United States
Bonnie N.
The price is ￥39,815
￥70,839 total
includes taxes & fees
Jun 21 - Jun 22
Island Time!
Beach nearby

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
On the beach, sun loungers, beach towels

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 ￥41,408
￥71,046 total
includes taxes & fees
Jun 23 - Jun 24
THE BEACH CONDO #107 BEACHFRONT FULL VIEW
On the beach

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 ￥86,956
￥132,493 total
includes taxes & fees
Jun 21 - Jun 22
Beachfront Bliss: Beach Castle #1 by RVA
On the beach, beach umbrellas

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 ￥54,785
￥93,173 total
includes taxes & fees
Jun 12 - Jun 13
1BR Beach Getaway – Silver Sands #254 by RVA
Smart TV

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, (145 reviews)
"A very considerate and available host! The condo was everything we could have wanted. Great location! Will return"
United States
Kathleen R.
The price is ￥44,503
￥93,101 total
includes taxes & fees
May 31 - Jun 1
Take a peek awesome reviews 50 feet from sand
Property grounds

Gulfside Comfort – Beach Castle #4 by RVA

Gulfside Comfort – Beach Castle #4 by RVA
Longboat Key
9.0 out of 10, Wonderful, (46 reviews)
"Everything was great, would definitely stay again!"
United States
Shelly V.
The price is ￥94,760
￥142,267 total
includes taxes & fees
Jun 20 - Jun 21
Gulfside Comfort – Beach Castle #4 by RVA
On the beach

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 ￥63,545
￥141,127 total
includes taxes & fees
Jun 2 - Jun 3
Updated Beachfront Condo at Prestigious Long Boat Key Resort
On the beach

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.
The price is ￥64,381
￥119,708 total
includes taxes & fees
Jun 20 - Jun 21
Luxurious Beachfront Jr. Suite by FVC
On the beach

3-bedroom, 3 bath condo in beautiful Longboat Key. Beachfront views w/ pool.

3-bedroom, 3 bath condo in beautiful Longboat Key. Beachfront views w/ pool.
Longboat Key
9.4 out of 10, Exceptional, (3 reviews)
"Great stay. Everything we needed. Communication with host was outstanding ! Perfect !!"
United States
Joe A.
3-bedroom, 3 bath condo in beautiful Longboat Key. Beachfront views w/ pool.
On the beach, beach umbrellas

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 ￥27,117
￥56,087 total
includes taxes & fees
May 31 - Jun 1
Relax at Gulf – Silver Sands Resort #232, Longboat
On the beach, beach umbrellas

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 ￥25,800
￥54,314 total
includes taxes & fees
Jun 2 - Jun 3
Gulfside Resort – Silver Sands #241A by RVA
On the beach, beach umbrellas

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 ￥30,578
￥60,834 total
includes taxes & fees
Jun 2 - Jun 3
Gulf Front Escape – Silver Sands #252 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

Oceanfront Bliss–Longboat Key Beach 106 by RVA

Oceanfront Bliss–Longboat Key Beach 106 by RVA

10/10 Excellent
"Beautiful location, steps from the beach. Close to necessities"
Chad C. 2-night trip
Posted 9 hours ago
Oceanfront Bliss–Longboat Key Beach 106 by RVA

Find out more about Longboat Key

Search for holiday rentals in Longboat Key on Expedia! You can easily find your home rentals, villas, holiday apartments in Longboat Key using one of the methods below:

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Look no further and take a look at our great range of rental properties in Longboat Key!

Frequently asked questions

Can I find a vacation rental in Longboat Key?

Yes, we have vacation rentals near popular local attractions in Longboat Key, or you can go with a secluded option if you're looking for relaxation. 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 vacation rentals that Longboat Key has to offer?

Siesta Key Island Rentals: This vacation home rental near Longboat Key comes with WiFi so you can feel at home during your trip. This vacation rental also comes with free parking to give you added peace of mind.

How many vacation rentals are there in Longboat Key?

Choose from 23 Expedia vacation rentals in Longboat Key for a memorable vacation.

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 vacation rentals like in Longboat Key?

Vacation rentals are privately owned accommodations you can stay in for several days or more in Longboat Key. Vacation rentals offer amenities like kitchens and laundry facilities so you'll have everything you need. If you're concerned about a clean environment, vacation rentals can provide a sense of seclusion away from public hotel elevators and busy reception areas while still allowing you to travel. You'll also find more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is an attractive choice for a family getaway.