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

Longboat Key Holiday Rentals

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Our top choices for Longboat Key holiday rentals

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

Island Time!

Island Time!
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.
The price is HK$2,156
HK$3,724 total
includes taxes & fees
16 Aug - 17 Aug
Island Time!

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)
"Excellent place to stay. "
United States
Hadley R.
The price is HK$1,560
HK$2,770 total
includes taxes & fees
28 Jul - 29 Jul
Beachfront- Longboat Key efficiency condo w/ king size bed, steps to sand.

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 HK$1,474
HK$2,989 total
includes taxes & fees
21 Jul - 22 Jul
The Beach on Longboat Key #227 Resort 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)
"Great location for the price! Also, it was well equipped with everything you need."
United States
LJ G.
The price is HK$2,372
HK$5,154 total
includes taxes & fees
18 Jul - 19 Jul
Cabana Beach Club - Beachfront Stunning Ocean View *Snow Bird Promo* Winter 2027

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 traveller
The price is HK$1,441
HK$3,284 total
includes taxes & fees
9 Aug - 10 Aug
Sunset and beach view from your balcony Unit 403

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 HK$1,960
HK$4,188 total
includes taxes & fees
19 Jul - 20 Jul
Gulfside 2BR Condo–Silver Sands #257S

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 HK$1,019
HK$2,349 total
includes taxes & fees
19 Jul - 20 Jul
Oceanfront Bliss–Longboat Key Beach 106 by RVA

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 HK$1,231
HK$2,627 total
includes taxes & fees
18 Jul - 19 Jul
Ground Floor, Steps to Sand – Silver Sands #243A by RVA

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 HK$1,850
HK$4,096 total
includes taxes & fees
20 Jul - 21 Jul
Roomy 2BR Retreat – Silver Sands #239 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, (96 reviews)
"Great view, clean, beautiful!"
United States
Bethany
The price is HK$1,443
HK$2,904 total
includes taxes & fees
11 Aug - 12 Aug
1BR Beach Getaway – Silver Sands #254 by RVA

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.
50 ft from sand, Private Island 125 +review

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 HK$1,450
HK$3,135 total
includes taxes & fees
17 Aug - 18 Aug
Drift & Dune – Longboat Beachfront #101 RVA

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 HK$1,764
HK$3,281 total
includes taxes & fees
11 Aug - 12 Aug
THE BEACH CONDO #107 BEACHFRONT FULL VIEW

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.
The price is HK$2,344
HK$4,777 total
includes taxes & fees
26 Jul - 27 Jul
Are you ready for a luxury 5-floor penthouse 60 ft from water, 207 reviews

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 HK$1,497
HK$2,985 total
includes taxes & fees
19 Jul - 20 Jul
Gulf Front Escape – Silver Sands #252 by RVA

Sunset and beach view from your balcony Unit 501

Sunset and beach view from your balcony Unit 501
Longboat Key
The price is HK$1,499
HK$2,974 total
includes taxes & fees
19 Jul - 20 Jul
Sunset and beach view from your balcony Unit 501

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 HK$2,375
HK$5,933 total
includes taxes & fees
11 Aug - 12 Aug
Updated Beachfront Condo at Prestigious Long Boat Key Resort

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 HK$1,403
HK$2,896 total
includes taxes & fees
23 Jul - 24 Jul
Newly Renovated 1BR – Cabana Beach #5 RVA

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 HK$1,199
HK$2,620 total
includes taxes & fees
26 Jul - 27 Jul
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

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 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 21 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.