Vacation Rentals in Cudjoe Key, Florida

50 Properties Available

Luxury * Panoramic Oceanfront Views * Boat Dock * Heated Pool Private vacation home
Luxury * Panoramic Oceanfront Views * Boat Dock * Heated Pool
$1141 / night
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105 - Newly renovated house Oceanside and Pool Private vacation home
105 - Newly renovated house Oceanside and Pool
$792 / night
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NAUTILUS...ocean front cottage retreat ~ Cottage
NAUTILUS...ocean front cottage retreat ~
$707 / night
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Rise And Shine On The Water Private vacation home
Rise And Shine On The Water
$697 / night
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Ocean-view snowbird retreat with private pool, rooftop, lanais, kayak & bikes Private vacation home
Ocean-view snowbird retreat with private pool, rooftop, lanais, kayak & bikes
$683 / night
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Oceanfront Seclusion, Oceanfront with pool Private vacation home
Oceanfront Seclusion, Oceanfront with pool
$622 / night
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WATERFRONT Seaside Sanctuary in the Keys with 35' SEAWALL FOR YOUR BOAT! Private vacation home
WATERFRONT Seaside Sanctuary in the Keys with 35' SEAWALL FOR YOUR BOAT!
$557 / night
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Modern Canal-Front Home with 35' Seawall, Bikes, Grill & Community Amenities Private vacation home
Modern Canal-Front Home with 35' Seawall, Bikes, Grill & Community Amenities
$549 / night
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Waterfront 2BR/2BA | 35' Seawall for 32' Boat | Beautiful Sunrises on Cudjoe Key Private vacation home
Waterfront 2BR/2BA | 35' Seawall for 32' Boat | Beautiful Sunrises on Cudjoe Key
$541 / night
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Ocean Vue in Cudjoe Key #469 Private vacation home
Ocean Vue in Cudjoe Key #469
$540 / night
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Sun Bake @ Sponge Cake, 64' Sea Wall, Great Seating, Fish Gulf or Atlantic Private vacation home
Sun Bake @ Sponge Cake, 64' Sea Wall, Great Seating, Fish Gulf or Atlantic
$530 / night
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Key Lime Hideaway - Oceanfront Gated Community, Amenities, 3BR Stilted Retreat Private vacation home
Key Lime Hideaway - Oceanfront Gated Community, Amenities, 3BR Stilted Retreat
$517 / night
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Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds! Private vacation home
Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds!
$511 / night
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Serenity in the Gardens Comfortable Coastal Living in the Florida Keys Private vacation home
Serenity in the Gardens Comfortable Coastal Living in the Florida Keys
$505 / night
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Modern comfort with a private pool, spa, kayaks, and ocean views Private vacation home
Modern comfort with a private pool, spa, kayaks, and ocean views
$500 / night
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"WEEKLY RENTAL" Florida Keys Pool & Waterfront Vacation Rental 108 Private vacation home
"WEEKLY RENTAL" Florida Keys Pool & Waterfront Vacation Rental 108
$496 / night
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2BR,2BA w KING Master,35' SeaWall-SS and Quartz Kitchen,Bikes, Kayaks and VIEWS Cottage
2BR,2BA w KING Master,35' SeaWall-SS and Quartz Kitchen,Bikes, Kayaks and VIEWS
$493 / night
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35' dock completely remodeled Home Private vacation home
35' dock completely remodeled Home
$492 / night
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OCEAN PARADISE AT VENTURE OUT + 4 BIKES & 2-2 PERSON KAYAKS! KING & QUEEN BEDS! Private vacation home
OCEAN PARADISE AT VENTURE OUT + 4 BIKES & 2-2 PERSON KAYAKS! KING & QUEEN BEDS!
$488 / night
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Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West Private vacation home
Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West
$486 / night
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Captains Quarters - Cudjoe Key - Pool- Up to 45' Boat Private vacation home
Captains Quarters - Cudjoe Key - Pool- Up to 45' Boat
$484 / night
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Blue Palms w/boat dock and saltwater pool. Private vacation home
Blue Palms w/boat dock and saltwater pool.
$482 / night
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Island Oasis ~ YOUR Paradise awaits in Venture Out Resort! Cottage
Island Oasis ~ YOUR Paradise awaits in Venture Out Resort!
$473 / night
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Canal Front Retreat w/ Ocean Views, 35' Dock & Golf Cart Option Private vacation home
Canal Front Retreat w/ Ocean Views, 35' Dock & Golf Cart Option
$463 / night
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Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access Private vacation home
Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access
$460 / night
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Canal front home @ Venture Out Resort in the Florida Keys! Private vacation home
Canal front home @ Venture Out Resort in the Florida Keys!
$445 / night
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SAVE BIG $$$ OCT./NOV. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS Private vacation home
SAVE BIG $$$ OCT./NOV. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
$444 / night
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Pelican's Roost, Waterfront comfort at Venture Out Private vacation home
Pelican's Roost, Waterfront comfort at Venture Out
$436 / night
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35' Seawall Sparkling , 30min from Keywest, WIFI, BBQ Grill, Pool Mobile home
35' Seawall Sparkling , 30min from Keywest, WIFI, BBQ Grill, Pool
$432 / night
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Manatee Hideaway #461 - Cudjoe Key, Canal Front Private vacation home
Manatee Hideaway #461 - Cudjoe Key, Canal Front
$420 / night
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Piece Of Eight - Venture Out 279 Private vacation home
Piece Of Eight - Venture Out 279
$419 / night
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Mile Marker Mahi - Venture Out #465 Cottage
Mile Marker Mahi - Venture Out #465
$413 / night
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Waterfront, Boat Dock, Heated Pool, Amenities #573, Waterfront Home, Heated Pool, Boat Dock Private vacation home
Waterfront, Boat Dock, Heated Pool, Amenities #573, Waterfront Home, Heated Pool, Boat Dock
$402 / night
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MANATEE HIDEAWAY 35' Seawall with Easy Ocean Access Atlantic Open Water or Gulf Private vacation home
MANATEE HIDEAWAY 35' Seawall with Easy Ocean Access Atlantic Open Water or Gulf
$397 / night
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Beach house in the Keys - VO074 Private vacation home
Beach house in the Keys - VO074
$375 / night
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Upscale Ocean-Front Escape w/ Private Pool, Dock & Open Water Views Private vacation home
Upscale Ocean-Front Escape w/ Private Pool, Dock & Open Water Views
$370 / night
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Location, location, location briefly describes this small piece of Paradise. Cottage
Location, location, location briefly describes this small piece of Paradise.
$360 / night
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Beautiful Ocean view with 35' private seawall, 80' Heated Pool, Hottub Private vacation home
Beautiful Ocean view with 35' private seawall, 80' Heated Pool, Hottub
$352 / night
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Awesome water front keys home 3bedroom, 2 bath. 20 miles from Key West! Private vacation home
Awesome water front keys home 3bedroom, 2 bath. 20 miles from Key West!
$341 / night
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Ocean view, Heated-chilled pool, Outdoor kitchen, downstairs bathroom w\/ shower! Private vacation home
Ocean view, Heated-chilled pool, Outdoor kitchen, downstairs bathroom w\/ shower!
$325 / night
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Lime in the coconut Private vacation home
Lime in the coconut
$322 / night
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Dazzling Bayfront Home w\/ 2 Boat Docks, Huge Deck, 1 Kayak, Pool Table -1 Dog OK Private vacation home
Dazzling Bayfront Home w\/ 2 Boat Docks, Huge Deck, 1 Kayak, Pool Table -1 Dog OK
$321 / night
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VO 173 2 Bed 2 Bath Silt Canal-Front, Ocean View Private vacation home
VO 173 2 Bed 2 Bath Silt Canal-Front, Ocean View
$309 / night
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3 bedroom, 2 bath, canal home with hot tub Private vacation home
3 bedroom, 2 bath, canal home with hot tub
$309 / night
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waterfront cottage near key west, sleeps 6 Cottage
waterfront cottage near key west, sleeps 6
$307 / night
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COCONUT TELEGRAPH ~ Waterfront 2 BR\/2Ba in Cudjoe Key w\/ Dockage & Parking! Private vacation home
COCONUT TELEGRAPH ~ Waterfront 2 BR\/2Ba in Cudjoe Key w\/ Dockage & Parking!
$307 / night
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BIG BLUE waits for you in the sunny Keys Private vacation home
BIG BLUE waits for you in the sunny Keys
$300 / night
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LICENSE TO CHILL ~ Waterfront 2 BR\/2Ba in Cudjoe Key w\/ Dockage & Parking! Private vacation home
LICENSE TO CHILL ~ Waterfront 2 BR\/2Ba in Cudjoe Key w\/ Dockage & Parking!
$293 / night
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Waterfront home with numerous amenities on popular Cudjoe Key! Mobile home
Waterfront home with numerous amenities on popular Cudjoe Key!
$291 / night
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Beautiful, 2100 sq ft 3/2 w/ocean views & easy ocean & gulf access. Private vacation home
Beautiful, 2100 sq ft 3/2 w/ocean views & easy ocean & gulf access.
$290 / night
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