A coastal cityscape with a sunset over the water, featuring several high-rise buildings and palm trees.

Longboat Key Vacation Rentals

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Check prices for these dates

In two weeks
Jul 31 - Aug 2
In two months
Sep 11 - Sep 13
In three months
Oct 9 - Oct 11
In four months
Nov 6 - Nov 8

Our top choices for Longboat Key vacation rentals

Beach nearby

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.
Best views of the beach from your balcony Unit 301
Outdoor dining

Island Time: Open Sunday, $225/nt + Fees!

Island Time: Open Sunday, $225/nt + Fees!
Longboat Key
10.0 out of 10, Exceptional, (130 reviews)
"Gorgeous view! Steps to the beach! The host was so accommodating & had great communication. We would highly recommend!"
United States
Angie T.
Island Time: Open Sunday, $225/nt + Fees!
On the beach

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, (21 reviews)
The price is ￥32,448
￥57,498 total
includes taxes & fees
Jul 28 - Jul 29
Beachfront- Longboat Key efficiency condo w/ king size bed, steps to sand.
Dining

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, (82 reviews)
"Great location and great views!"
United States
Mark H.
The price is ￥33,465
￥65,589 total
includes taxes & fees
Aug 10 - Aug 11
The Beach on Longboat Key #227 Resort by RVA
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)
"Great location for the price! Also, it was well equipped with everything you need."
United States
LJ G.
The price is ￥49,078
￥106,662 total
includes taxes & fees
Jul 18 - Jul 19
Cabana Beach Club - Beachfront Stunning Ocean View *Snow Bird Promo* Winter 2027
Smart TV

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 traveler
The price is ￥29,850
￥68,057 total
includes taxes & fees
Aug 9 - Aug 10
Sunset and beach view from your balcony Unit 403
On the beach, beach umbrellas

Gulfside 2BR Condo–Silver Sands #257S

Gulfside 2BR Condo–Silver Sands #257S
Longboat Key
8.6 out of 10, Excellent, (36 reviews)
"The location was perfect right on the beach"
United States
Ana
The price is ￥46,238
￥94,290 total
includes taxes & fees
Jul 19 - Jul 20
Gulfside 2BR Condo–Silver Sands #257S
On the beach

Oceanfront Bliss–Longboat Key Beach 106 by RVA

Oceanfront Bliss–Longboat Key Beach 106 by RVA
Longboat Key
8.8 out of 10, Excellent, (103 reviews)
"Very clean room and property. Very pleased with our stay. Would highly recommend."
United States
Andrea O.
The price is ￥26,804
￥56,635 total
includes taxes & fees
Aug 9 - Aug 10
Oceanfront Bliss–Longboat Key Beach 106 by RVA
On the beach, beach umbrellas

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 ￥25,342
￥54,235 total
includes taxes & fees
Jul 19 - Jul 20
Ground Floor, Steps to Sand – Silver Sands #243A by RVA
On the beach, beach umbrellas

Roomy 2BR Retreat – Silver Sands #239 by RVA

Roomy 2BR Retreat – Silver Sands #239 by RVA
Longboat Key
9.6 out of 10, Exceptional, (48 reviews)
"Condo was great! Lots of space, clean, and great location"
United States
Sherry R.
The price is ￥38,176
￥84,359 total
includes taxes & fees
Jul 27 - Jul 28
Roomy 2BR Retreat – Silver Sands #239 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, (96 reviews)
"Great view, clean, beautiful!"
United States
Bethany
The price is ￥29,891
￥60,820 total
includes taxes & fees
Aug 13 - Aug 14
1BR Beach Getaway – Silver Sands #254 by RVA
Property grounds

50 ft from sand, Private Island 125 +review

50 ft from sand, Private Island 125 +review
Longboat Key
10.0 out of 10, Exceptional, (135 reviews)
"Excellent location. Beautifully furnished. Steps from the beach!"
United States
Laurie B.
The price is ￥45,324
￥93,843 total
includes taxes & fees
Jul 17 - Jul 18
50 ft from sand, Private Island 125 +review
On the beach

Drift & Dune – Longboat Beachfront #101 RVA

Drift & Dune – Longboat Beachfront #101 RVA
Longboat Key
8.6 out of 10, Excellent, (83 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 ￥29,728
￥65,703 total
includes taxes & fees
Aug 13 - Aug 14
Drift & Dune – Longboat Beachfront #101 RVA
On the beach, sun loungers, beach towels

THE BEACH CONDO #107 BEACHFRONT FULL VIEW

THE BEACH CONDO #107 BEACHFRONT FULL VIEW
Longboat Key
10.0 out of 10, Exceptional, (95 reviews)
"Host was wondeful!Location and condo fabulous!"
United States
Linda D.
The price is ￥36,504
￥67,743 total
includes taxes & fees
Aug 14 - Aug 15
THE BEACH CONDO #107 BEACHFRONT FULL VIEW
Property grounds

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, (211 reviews)
"Great location."
United States
Janet B.
Are you ready for a luxury 5-floor penthouse 60 ft from water, 207 reviews
On the beach, beach umbrellas

Gulf Front Escape – Silver Sands #252 by RVA

Gulf Front Escape – Silver Sands #252 by RVA
Longboat Key
9.0 out of 10, Wonderful, (106 reviews)
"Staff was welcoming- place was clean and stay was great"
United States
Joseph S.
The price is ￥31,028
￥61,858 total
includes taxes & fees
Jul 19 - Jul 20
Gulf Front Escape – Silver Sands #252 by RVA
TV, offices

Sunset and beach view from your balcony Unit 501

Sunset and beach view from your balcony Unit 501
Longboat Key
Sunset and beach view from your balcony Unit 501
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)
The price is ￥49,159
￥122,300 total
includes taxes & fees
Aug 14 - Aug 15
Updated Beachfront Condo at Prestigious Long Boat Key Resort
On the beach

Newly Renovated 1BR – Cabana Beach #5 RVA

Newly Renovated 1BR – Cabana Beach #5 RVA
Longboat Key
8.8 out of 10, Excellent, (75 reviews)
"The view and beach access was amazing. Loved our stay. "
United States
Julie F.
The price is ￥28,916
￥59,491 total
includes taxes & fees
Aug 9 - Aug 10
Newly Renovated 1BR – Cabana Beach #5 RVA
On the beach, beach umbrellas

Starfish Studio Silver Sands #247A – Studio/1BA Resort in LBK

Starfish Studio Silver Sands #247A – Studio/1BA Resort in LBK
Longboat Key
8.0 out of 10, Very Good, (9 reviews)
"Nice place, clean, conveniently located, right on the beach, very helpful/friendly manager. We didn’t use the pool but it was clean and well taken care of, also heated. Beach was awesome, soft clean sand, clear water. Would like to stay here again."
United States
William
The price is ￥24,855
￥53,651 total
includes taxes & fees
Jul 17 - Jul 18
Starfish Studio Silver Sands #247A – Studio/1BA Resort in LBK
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

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

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

10/10 Excellent
"Great little place to enjoy the beach"
Victoria F. 2-night trip
Posted 6 hours ago
Beachfront- Longboat Key efficiency condo w/ king size bed, steps to sand.

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 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 21 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. Lido Beach and Siesta Key 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.