Cudjoe Key, Florida

Vacation Rentals in Cudjoe Key, Florida

Discover 20 vacation rental properties in Cudjoe Key. From 1 to 3 bedrooms. Average $237/night. 100% have pools.

20 verified listings Book securely on VRBO Prices updated March 2026

20 properties available

Ocean Perch, Dock, Open Water Views, 80' Heated Pool, Tennis, 20 Min to Key West

Ocean Perch, Dock, Open Water Views, 80' Heated Pool, Tennis, 20 Min to Key West

2 beds 2 baths
PoolA/CWiFiBalcony
$274/night
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Cottage with Pool and Boat Dockage just minutes to Key West!

Cottage with Pool and Boat Dockage just minutes to Key West!

1 bed 1 bath
PoolA/CWiFiBalcony
$157/night
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Cottage with swimming pool and dockage, just minutes to Key West!

Cottage with swimming pool and dockage, just minutes to Key West!

1 bed 1 bath
PoolA/CWiFiBalcony
$157/night
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Cottage with Pool and Dockage, just minutes to Key West

Cottage with Pool and Dockage, just minutes to Key West

2 beds 1 bath
PoolA/CWiFiBalcony
$188/night
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Private Oceanfront Cottage with dockage, pool just minutes to Key West!

Private Oceanfront Cottage with dockage, pool just minutes to Key West!

1 bed 1 bath
PoolA/CWiFiBalcony
$185/night
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Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

2 beds 1 bath
PoolA/CWiFiBalcony
$241/night
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Canal Front, Spa/Pool, 2 Kayaks, 2 Bikes, 3 Bed, 2 Bath, Oceanside Home

Canal Front, Spa/Pool, 2 Kayaks, 2 Bikes, 3 Bed, 2 Bath, Oceanside Home

3 beds 2 baths
PoolA/CWiFiBalcony
$159/night
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Luxurious Oceanfront Home on Beach, Dock, Heat/Cool Pool, FirePit, Kayaks, Bikes

Luxurious Oceanfront Home on Beach, Dock, Heat/Cool Pool, FirePit, Kayaks, Bikes

2 beds 3 baths
PoolA/CWiFiBalcony
$359/night
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Walk to Beach, Open Water View from porch , dock, bikes, kayaks & snorkel gear

Walk to Beach, Open Water View from porch , dock, bikes, kayaks & snorkel gear

2 beds 1 bath
PoolA/CWiFiBalcony
$287/night
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Shore Thing at Venture Out With 50’ Private Dock, Bring Your Boat!

Shore Thing at Venture Out With 50’ Private Dock, Bring Your Boat!

2 beds 2 baths
PoolA/CWiFiBalcony
$277/night
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Cudjoe Bay Access Vacation House In Paradise

Cudjoe Bay Access Vacation House In Paradise

2 beds 1 bath
PoolA/CWiFiBalcony
$201/night
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Canal front, dockage, 2 bedroom, 2 bath

Canal front, dockage, 2 bedroom, 2 bath

2 beds 2 baths
PoolA/CWiFiBalcony
$240/night
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Comfortable Waterfront Vacation Rental

Comfortable Waterfront Vacation Rental

1 bed 1 bath
PoolA/CWiFiBalcony
$169/night
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Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes

Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes

2 beds 3 baths
PoolA/CWiFiBalcony
$353/night
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Dazzling Bayfront Home w/ 2 Boat Docks, Huge Deck, 1 Kayak, Pool Table -1 Dog OK

Dazzling Bayfront Home w/ 2 Boat Docks, Huge Deck, 1 Kayak, Pool Table -1 Dog OK

3 beds 2 baths
PoolA/CWiFiBalcony
$248/night
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LATITUDE ADJUSTMENT

LATITUDE ADJUSTMENT

2 beds 1 bath
PoolA/CWiFiBalcony
$155/night
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20 MINUTES TO KEY WEST , BOATERS PARADISE

20 MINUTES TO KEY WEST , BOATERS PARADISE

2 beds 1 bath
PoolA/CWiFiBalcony
$215/night
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Quaint cottage, pool, dockage just minutes to Key West!

Quaint cottage, pool, dockage just minutes to Key West!

2 beds 1 bath
PoolA/CWiFiBalcony
$208/night
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Canal front home @ Venture Out Resort in the Florida Keys!

Canal front home @ Venture Out Resort in the Florida Keys!

2 beds 2 baths
PoolA/CWiFiBalcony
$352/night
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**POSTCARD POINT @ VENTURE OUT** New Waterfront Home + LAST KEY SERVICES…

**POSTCARD POINT @ VENTURE OUT** New Waterfront Home + LAST KEY SERVICES…

2 beds 2 baths
PoolA/CWiFiBalcony
$312/night
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