Longboat Key Vacation Rentals

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Our top choices for Longboat Key vacation rentals

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 CA $545
CA $1,226 total
includes taxes & fees
Apr 28 - Apr 29
Updated Beachfront Condo at Prestigious Long Boat Key Resort

Island Time!

Island Time!
Longboat Key
10.0 out of 10, Exceptional, (124 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 CA $324
CA $604 total
includes taxes & fees
May 3 - May 4
Island Time!

Drift & Dune – Longboat Beachfront #101 RVA

Drift & Dune – Longboat Beachfront #101 RVA
Longboat Key
8.6 out of 10, Excellent, (79 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 $216
CA $505 total
includes taxes & fees
Apr 29 - Apr 30
Drift & Dune – Longboat Beachfront #101 RVA

Charming 1-bedroom, Beachfront condo in fabulous Longboat Key steps to the beach

Charming 1-bedroom, Beachfront condo in fabulous Longboat Key steps to the beach
Longboat Key
8.6 out of 10, Excellent, (20 reviews)
"It was in great condition and an overall good experience. "
United States
Ava G.
The price is CA $342
CA $609 total
includes taxes & fees
May 3 - May 4
Charming 1-bedroom, Beachfront condo in fabulous Longboat Key steps to the beach

THE BEACH CONDO #107 BEACHFRONT FULL VIEW

THE BEACH CONDO #107 BEACHFRONT FULL VIEW
Longboat Key
9.8 out of 10, Exceptional, (87 reviews)
"Incredible place. Already booked again!! "
United States
Julie T.
The price is CA $338
CA $616 total
includes taxes & fees
Apr 30 - May 1
THE BEACH CONDO #107 BEACHFRONT FULL VIEW

Client texted view crazy Last minute cancellation Apr 25 - May 16th on sale

Client texted view crazy Last minute cancellation Apr 25 - May 16th on sale
Longboat Key
10.0 out of 10, Exceptional, (100 reviews)
"Location and view was amazing "
United States
joseph l.
The price is CA $340
CA $746 total
includes taxes & fees
Apr 28 - Apr 29
Client texted view crazy Last minute cancellation Apr 25 - May 16th on sale

Ocean Breeze, Mind at Ease!

Ocean Breeze, Mind at Ease!
Longboat Key
10.0 out of 10, Exceptional, (89 reviews)
"Great accommodations, excellent location, amazing host!"
United States
Ella F.
The price is CA $292
CA $558 total
includes taxes & fees
Apr 30 - May 1
Ocean Breeze, Mind at Ease!

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)
"Beautiful View. Clean. Well Equipped. Comfortable Bed. Tiny Bathroom. Lovely Balcony with comfortable chairs. Old Resort. Stair access only. Access to unit via master bedroom."
United States
Susan T.
The price is CA $294
CA $565 total
includes taxes & fees
Apr 30 - May 1
Gulf Views – Silver Sands #250, Longboat Key by RVA

Are you ready for a luxury 5-floor penthouse 60 ft from water, 207 reviews

Are you ready for a luxury 5-floor penthouse 60 ft from water, 207 reviews
Longboat Key
10.0 out of 10, Exceptional, (207 reviews)
"Great location."
United States
Janet B.
The price is CA $409
CA $826 total
includes taxes & fees
May 9 - May 10
Are you ready for a luxury 5-floor penthouse 60 ft from water, 207 reviews

Sandy Toes & Sun Kissed Nose!

Sandy Toes & Sun Kissed Nose!
Longboat Key
9.6 out of 10, Exceptional, (10 reviews)
"We had a wonderful stay, the condo was very well equipped and the host was absolutely fantastic! "
United States
Emily L.
Sandy Toes & Sun Kissed Nose!

Beachfront Bliss on Longboat Key- Steps to the sand

Beachfront Bliss on Longboat Key- Steps to the sand
Longboat Key
8.6 out of 10, Excellent, (15 reviews)
"Great locale right on the beach "
United States
Carole
The price is CA $308
CA $566 total
includes taxes & fees
May 4 - May 5
Beachfront Bliss on Longboat Key- Steps to the sand

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, (77 reviews)
"Property was as indicated. Office staff was very friendly and accommodating. Property was quiet.We were just steps from the direct beach access."
United States
Leen S.
The price is CA $226
CA $479 total
includes taxes & fees
Apr 29 - Apr 30
Gulf Breezes & Poolside Peace – Silver Sands #236 by 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, (94 reviews)
"Great view, clean, beautiful!"
United States
Bethany
The price is CA $256
CA $518 total
includes taxes & fees
May 11 - May 12
1BR Beach Getaway – Silver Sands #254 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, (96 reviews)
"Beautiful sunset view. "
United States
Rhonda V.
The price is CA $178
CA $410 total
includes taxes & fees
Apr 30 - May 1
Oceanfront Bliss–Longboat Key Beach 106 by RVA

Beachfront Escape – Private Balcony, Gulf Views, No Street to Cross, Watch the Sunset from Your Balcony

Beachfront Escape – Private Balcony, Gulf Views, No Street to Cross, Watch the Sunset from Your Balcony
Longboat Key
9.8 out of 10, Exceptional, (144 reviews)
"Host was great. The accommodations were perfect for what we wanted and had everything we needed. And the view was spectacular! "
United States
Joan S.
Beachfront Escape – Private Balcony, Gulf Views, No Street to Cross, Watch the Sunset from Your Balcony

Relax at Gulf – Silver Sands Resort #232, Longboat

Relax at Gulf – Silver Sands Resort #232, Longboat
Longboat Key
9.2 out of 10, Wonderful, (79 reviews)
"Great beach access. Central location on the island. Not overcrowded. Ground floor unit was in good shape considering the hurricane in 2024.Bedroom could use blackout curtains (it gets bright in there in the AM) and the road noise was a bit loud."
United States
Mark G.
The price is CA $231
CA $486 total
includes taxes & fees
Apr 28 - Apr 29
Relax at Gulf – Silver Sands Resort #232, Longboat

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 CA $213
CA $462 total
includes taxes & fees
Apr 28 - Apr 29
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, (103 reviews)
"Perfect for our family "
United States
Alan B.
The price is CA $261
CA $526 total
includes taxes & fees
Apr 28 - Apr 29
Gulf Front Escape – Silver Sands #252 by RVA

Affordable Beach Studio – Silver Sands #257A by RVA

Affordable Beach Studio – Silver Sands #257A by RVA
Longboat Key
9.6 out of 10, Exceptional, (76 reviews)
"Right on beach-perfect for a short stay"
United States
Sean P.
The price is CA $200
CA $444 total
includes taxes & fees
May 3 - May 4
Affordable Beach Studio – Silver Sands #257A 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 $220
CA $471 total
includes taxes & fees
Apr 28 - Apr 29
Gulfside Resort – Silver Sands #241A 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 free 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 18 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.