Longboat Key, Florida

Vacation Rentals in Longboat Key, Florida

Discover 71 vacation rental properties in Longboat Key. From 1 to 5 bedrooms. Average $301/night. 100% have pools.

71 verified listings Book securely on VRBO Prices updated March 2026

71 properties available

Open Thursday, June 27th, $225/nt!

Open Thursday, June 27th, $225/nt!

1 bath
PoolA/CWiFiBalcony
$269/night
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Breathtaking Beach Front Property Ground Floor Condo

Breathtaking Beach Front Property Ground Floor Condo

2 beds 2 baths
PoolA/CWiFiBalcony
$260/night
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2/2 GULF SIDE UPDATED APARTMENT Seasonal special, 6/25 to 29, 2024-275.00 night

2/2 GULF SIDE UPDATED APARTMENT Seasonal special, 6/25 to 29, 2024-275.00 night

2 beds 2 baths
PoolA/CWiFiBalcony
$296/night
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Silver Sands #237 Resort by RVA

Silver Sands #237 Resort by RVA

1 bath
PoolA/CWiFiBalcony
$204/night
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The Beach on Longboat Key #226 Resort by RVA

The Beach on Longboat Key #226 Resort by RVA

1 bath
PoolA/CWiFiBalcony
$384/night
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Wonderful Canal Front Condo! See Manatees Right From Your Doorstep!Cabana #10

Wonderful Canal Front Condo! See Manatees Right From Your Doorstep!Cabana #10

1 bed 1 bath
PoolA/CWiFiBalcony
$204/night
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Direct Beachfront Gulf with Amazing Views

Direct Beachfront Gulf with Amazing Views

2 beds 2 baths
PoolA/CWiFiBalcony
$439/night
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Silver Sands #242 Resort by RVA

Silver Sands #242 Resort by RVA

1 bed 1 bath
PoolA/CWiFiBalcony
$339/night
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Silver Sands #232 Resort by RVA

Silver Sands #232 Resort by RVA

1 bed 1 bath
PoolA/CWiFiBalcony
$283/night
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Longboat Key Cedars Beach House-Pet Friendly-2 Minute Walk To The Beach

Longboat Key Cedars Beach House-Pet Friendly-2 Minute Walk To The Beach

2 beds 2 baths
PoolA/CWiFiBalcony
$165/night
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Beach view. Year-round Balcony Sunsets. Just renovated.

Beach view. Year-round Balcony Sunsets. Just renovated.

1 bed 1 bath
PoolA/CWiFiBalcony
$255/night
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Gorgeous Condo On The Beautiful Longboat Key beach! Also available next door #8

Gorgeous Condo On The Beautiful Longboat Key beach! Also available next door #8

1 bed 1 bath
PoolA/CWiFiBalcony
$225/night
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THE BEACH, condo #107, PRIVATE BEACH

THE BEACH, condo #107, PRIVATE BEACH

1 bath
PoolA/CWiFiBalcony
$250/night
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The Beach on Longboat Key #225 Resort by RVA

The Beach on Longboat Key #225 Resort by RVA

1 bed 1 bath
PoolA/CWiFiBalcony
$419/night
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Silver Sands #239 Resort by RVA

Silver Sands #239 Resort by RVA

2 beds 1 bath
PoolA/CWiFiBalcony
$347/night
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Luxury Beach Condo with Breathtaking Views Upgraded! PROMO 2024 !!,

Luxury Beach Condo with Breathtaking Views Upgraded! PROMO 2024 !!,

2 beds 2 baths
PoolA/CWiFiBalcony
$325/night
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The Beach on Longboat Key #220 Resort by RVA

The Beach on Longboat Key #220 Resort by RVA

1 bath
PoolA/CWiFiBalcony
$248/night
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Beautiful Updated Beachfront Condo on the Gulf of Mexico

Beautiful Updated Beachfront Condo on the Gulf of Mexico

2 beds 2 baths
PoolA/CWiFiBalcony
$262/night
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Beach Front No Crossing Needed Condo Paradise. Ground Floor. Full kitchen.

Beach Front No Crossing Needed Condo Paradise. Ground Floor. Full kitchen.

1 bed 1 bath
PoolA/CWiFiBalcony
$199/night
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Beach View Condo- Quiet & Secluded with Private Beach

Beach View Condo- Quiet & Secluded with Private Beach

2 beds 2 baths
PoolA/CWiFiBalcony
$372/night
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Beach Front No Crossing Needed One Bedroom Condo. Fully Renovated. Ground Floor.

Beach Front No Crossing Needed One Bedroom Condo. Fully Renovated. Ground Floor.

1 bed 1 bath
PoolA/CWiFiBalcony
$236/night
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Updated Beach Style Condo at Sand Cay with Great Ocean Views.

Updated Beach Style Condo at Sand Cay with Great Ocean Views.

2 beds 2 baths
PoolA/CWiFiBalcony
$337/night
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Longboat Key Beachfront - Beautifully Updated with Prime Location

Longboat Key Beachfront - Beautifully Updated with Prime Location

2 beds 2 baths
PoolA/CWiFiBalcony
$216/night
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Steps from the Water with Spectacular Bay Views

Steps from the Water with Spectacular Bay Views

2 beds 2 baths
PoolA/CWiFiBalcony
$90/night
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The Beach on Longboat Key #224 Resort by RVA

The Beach on Longboat Key #224 Resort by RVA

1 bed 1 bath
PoolA/CWiFiBalcony
$382/night
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Cute canal front Cottage with dock & boat lift and pool ,short walk to the beach

Cute canal front Cottage with dock & boat lift and pool ,short walk to the beach

2 beds 2 baths
PoolA/CWiFiBalcony
$357/night
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Silver Sands #252 Resort by RVA

Silver Sands #252 Resort by RVA

1 bed 1 bath
PoolA/CWiFiBalcony
$325/night
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Renovated beachfront 2brm by FVC

Renovated beachfront 2brm by FVC

2 beds 2 baths
PoolA/CWiFiBalcony
$690/night
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Perfect Beach View Large 2 bedroom

Perfect Beach View Large 2 bedroom

2 beds 2 baths
PoolA/CWiFiBalcony
$685/night
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2 bedroom beachfront condo by FVC

2 bedroom beachfront condo by FVC

2 beds 2 baths
PoolA/CWiFiBalcony
$436/night
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Tastefully decorated and spacious studio overlooking Island Lagoon.

Tastefully decorated and spacious studio overlooking Island Lagoon.

1 bath
PoolA/CWiFiBalcony
$240/night
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Longboat Key Club!! Direct Beachfront!!

Longboat Key Club!! Direct Beachfront!!

1 bed 1 bath
PoolA/CWiFiBalcony
$246/night
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Client texted and said View Crazy.Added remote blinds & drape accents pic soon

Client texted and said View Crazy.Added remote blinds & drape accents pic soon

1 bed 1 bath
PoolA/CWiFiBalcony
$293/night
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Luxurious Beachfront Suite by FVC

Luxurious Beachfront Suite by FVC

1 bath
PoolA/CWiFiBalcony
$277/night
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Bird's eye beach view by FVC

Bird's eye beach view by FVC

2 beds 2 baths
PoolA/CWiFiBalcony
$578/night
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Tasteful 2brm Beachfront luxury

Tasteful 2brm Beachfront luxury

2 beds 2 baths
PoolA/CWiFiBalcony
$692/night
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Beautiful Beach Longboat Key Townhouse

Beautiful Beach Longboat Key Townhouse

2 beds 2 baths
PoolA/CWiFiBalcony
$230/night
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Club Suite at Longboat Key Club

Club Suite at Longboat Key Club

1 bed 1 bath
PoolA/CWiFiBalcony
$494/night
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Unit #202 Sand Cay Beach Resort Gulf Front

Unit #202 Sand Cay Beach Resort Gulf Front

2 beds 2 baths
PoolA/CWiFiBalcony
$363/night
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Gorgeous condo on the beautiful Longboat Key beach.Next door #9 also available.

Gorgeous condo on the beautiful Longboat Key beach.Next door #9 also available.

2 beds 1 bath
PoolA/CWiFiBalcony
$235/night
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Beachfront Incredible Panoramic Gulf View and The Most Beautiful Sunset.

Beachfront Incredible Panoramic Gulf View and The Most Beautiful Sunset.

1 bed 1 bath
PoolA/CWiFiBalcony
$260/night
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Steps from the beach on Longboat Key

Steps from the beach on Longboat Key

1 bed 1 bath
PoolA/CWiFiBalcony
$132/night
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Open Friday, $125/nt!

Open Friday, $125/nt!

1 bed 1 bath
PoolA/CWiFiBalcony
$267/night
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Dolphin Tale #12 Condo by RVA

Dolphin Tale #12 Condo by RVA

2 beds 2 baths
PoolA/CWiFiBalcony
$184/night
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Waterfront condo with pool, tennis court, fitness center, internet, W/D, & AC

Waterfront condo with pool, tennis court, fitness center, internet, W/D, & AC

2 beds 2 baths
PoolA/CWiFiBalcony
$112/night
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White sands and no crowds! High end yet low key beachfront condo in Longboat Key

White sands and no crowds! High end yet low key beachfront condo in Longboat Key

2 beds 2 baths
PoolA/CWiFiBalcony
$166/night
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Panoramic beach View and amazing Sunset.

Panoramic beach View and amazing Sunset.

1 bed 1 bath
PoolA/CWiFiBalcony
$267/night
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Last Minute cancel June 29-July 6Take a Peek fabulous unit

Last Minute cancel June 29-July 6Take a Peek fabulous unit

1 bed 1 bath
PoolA/CWiFiBalcony
$292/night
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Showing 48 of 71 properties

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