Longboat Key Vacation Rentals

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Our top choices for Longboat Key vacation rentals

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 CA $661
CA $1,451 total
includes taxes & fees
Jun 6 - Jun 7
2 Bedroom Beachfront Condo by FVC

Renovated Beach Paradise. Ground Floor unit 64

Renovated Beach Paradise. Ground Floor unit 64
Longboat Key
9.8 out of 10, Exceptional, (68 reviews)
"Everything was perfect the location was amazing Very clean and welcoming "
United States
Brian M.
The price is CA $261
CA $589 total
includes taxes & fees
Jun 7 - Jun 8
Renovated Beach Paradise. Ground Floor unit 64

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 CA $196
CA $485 total
includes taxes & fees
Jun 2 - Jun 3
Drift & Dune – Longboat Beachfront #101 RVA

Silver Sands 1BR – Gulfside Comfort #255 by RVA

Silver Sands 1BR – Gulfside Comfort #255 by RVA
Longboat Key
9.0 out of 10, Wonderful, (87 reviews)
"Location #1. Clean #2"
United States
Eric C.
The price is CA $259
CA $526 total
includes taxes & fees
Jun 4 - Jun 5
Silver Sands 1BR – Gulfside Comfort #255 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, (90 reviews)
"Everything was great "
United States
kirt v.
The price is CA $253
CA $574 total
includes taxes & fees
Jun 12 - Jun 13
Best views of the beach from your balcony Unit 301

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 CA $297
CA $576 total
includes taxes & fees
Jun 4 - Jun 5
Gulf Views – Silver Sands #250, Longboat Key by RVA

Island Time on LBK!

Island Time on LBK!
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 CA $310
CA $588 total
includes taxes & fees
Jun 21 - Jun 22
Island Time on LBK!

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 CA $215
CA $466 total
includes taxes & fees
Jun 4 - Jun 5
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 CA $263
CA $527 total
includes taxes & fees
Jun 3 - Jun 4
Gulf Front Escape – Silver Sands #252 by RVA

Charming 1-bedroom, beachfront condo in marvelous Longboat Key

Charming 1-bedroom, beachfront condo in marvelous Longboat Key
Longboat Key
9.0 out of 10, Wonderful, (51 reviews)
"Great location. "
United States
Maureen R.
The price is CA $345
CA $614 total
includes taxes & fees
Jun 4 - Jun 5
Charming 1-bedroom, beachfront condo in marvelous Longboat Key

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 CA $492
CA $839 total
includes taxes & fees
Jun 21 - Jun 22
1BR Beach Getaway – Silver Sands #254 by RVA

Beachfront Studio – Cabana #5B by RVA

Beachfront Studio – Cabana #5B by RVA
Longboat Key
8.2 out of 10, Very good, (78 reviews)
"The pool was disgusting, dirt and debris on the bottom and top so that was disappointing, while watching TV and sleeping a person actually opened up our porch door then the main door and just walked in and said they had booked the same room and had keys, what kind of place does not keep track of that and I'm not sure what the person was thinking the TV was on and it was up a little so I know they heard it from the outside but to get back to that place for allowing that to happen. He's lucky I...
United States
Joseph
The price is CA $207
CA $429 total
includes taxes & fees
Jun 4 - Jun 5
Beachfront Studio – Cabana #5B 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 price is CA $258
CA $524 total
includes taxes & fees
Jun 2 - Jun 3
The Beach on Longboat Key #227 Resort by RVA

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 CA $222
CA $472 total
includes taxes & fees
Jun 3 - Jun 4
Gulfside Resort – Silver Sands #241A by RVA

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 CA $417
CA $918 total
includes taxes & fees
Jun 20 - Jun 21
Cabana Beach Club - Beachfront Stunning Ocean View *Snow Bird Promo* Winter 2027

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 CA $550
CA $1,237 total
includes taxes & fees
Jun 8 - Jun 9
Updated Beachfront Condo at Prestigious Long Boat Key Resort

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 CA $234
CA $492 total
includes taxes & fees
Jun 8 - Jun 9
Relax at Gulf – Silver Sands Resort #232, Longboat

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)
"We arrived late in the day and found the check in process well thought out and easy. The unit was very clean, the office staff very friendly and helpful. The whole facility was very quiet. Finally, the location was great, right on the beach. "
United States
Hal S.
The price is CA $274
CA $605 total
includes taxes & fees
Jun 18 - Jun 19
Sunset and beach view from your balcony Unit 403

THE BEACH CONDO #107 BEACHFRONT FULL VIEW

THE BEACH CONDO #107 BEACHFRONT FULL VIEW
Longboat Key
9.8 out of 10, Exceptional, (93 reviews)
"Host was wondeful!Location and condo fabulous!"
United States
Linda D.
The price is CA $359
CA $644 total
includes taxes & fees
Jun 19 - Jun 20
THE BEACH CONDO #107 BEACHFRONT FULL VIEW

Silver Sands #245A Resort by RVA

Silver Sands #245A Resort by RVA
Longboat Key
8.6 out of 10, Excellent, (62 reviews)
"Location and facilities wer excellent. "
United States
donald m.
The price is CA $212
CA $459 total
includes taxes & fees
Jun 3 - Jun 4
Silver Sands #245A 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

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Longboat Key. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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.