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Cudjoe Key Holiday Rentals

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100 rentals in Cudjoe Key.
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Oceanview Estate 15 minutes from Key West - 6 bedroom accommodate 13 guests, holiday rental in Cudjoe Key

Oceanview Estate 15 minutes from Key West - 6 bedroom accommodate 13 guests

6 bedrooms
3 bathrooms
Sleeps 14
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4 other travellers have booked this property
Fandango, holiday rental in Cudjoe Key

Fandango

5 bedrooms
3 bathrooms
Sleeps 14
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1 other traveller has booked this property
Family Retreat-Ocean front home with private pool, holiday rental in Cudjoe Key

Family Retreat-Ocean front home with private pool

6 bedrooms
4 bathrooms
Sleeps 14
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Tropical Paradise Oceanfront Home with Pool, holiday rental in Cudjoe Key

Tropical Paradise Oceanfront Home with Pool

2 bedrooms
2 bathrooms
Sleeps 6
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Charming 3bedroom/2bath home in the Florida Keys, holiday rental in Cudjoe Key

Charming 3bedroom/2bath home in the Florida Keys

3 bedrooms
2 bathrooms
Sleeps 6
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3 other travellers have booked this property
Lafitte Landing, holiday rental in Cudjoe Key

Lafitte Landing

2 bedrooms
2 bathrooms
Sleeps 4
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Pirate's Cove, holiday rental in Cudjoe Key

Pirate's Cove

2 bedrooms
1 bathroom
Sleeps 4
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Quiet Waters, holiday rental in Cudjoe Key

Quiet Waters

3 bedrooms
2 bathrooms
Sleeps 6
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Paradise Bay, holiday rental in Cudjoe Key

Paradise Bay

3 bedrooms
2 bathrooms
Sleeps 6
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Palm Harbor, holiday rental in Cudjoe Key

Palm Harbor

3 bedrooms
2 bathrooms
Sleeps 8
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Egret's Landing, holiday rental in Cudjoe Key

Egret's Landing

3 bedrooms
2 bathrooms
Sleeps 6
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Cudjoe Ocean Shores, holiday rental in Cudjoe Key

Cudjoe Ocean Shores

3 bedrooms
2 bathrooms
Sleeps 6
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Keys Escape, holiday rental in Cudjoe Key

Keys Escape

3 bedrooms
3 bathrooms
Sleeps 6
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Paradise in the Lower Keys!, holiday rental in Cudjoe Key

Paradise in the Lower Keys!

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Beautiful home in oceanfront resort with pool & dock, 16 miles from Key West, holiday rental in Cudjoe Key

Beautiful home in oceanfront resort with pool & dock, 16 miles from Key West

2 bedrooms
3 bathrooms
Sleeps 6
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Beautiful Family-Friendly home, Dock, Heated Pool, near Key West, MM21.5, holiday rental in Cudjoe Key

Beautiful Family-Friendly home, Dock, Heated Pool, near Key West, MM21.5

2 bedrooms
3 bathrooms
Sleeps 6
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Direct Oceanfront - Atlantic Side - Dockage - Swimming Pool - Kayak, holiday rental in Cudjoe Key

Direct Oceanfront - Atlantic Side - Dockage - Swimming Pool - Kayak

3 bedrooms
2 bathrooms
Sleeps 7
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Comfortable Waterfront Vacation Rental, holiday rental in Cudjoe Key

Comfortable Waterfront Vacation Rental

1 bedroom
1 bathroom
Sleeps 4
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* OCEAN FRONT * Private 56' DOCK * 5 to 7 night min. **  MAXIMUM OCCUPANCY  4 **, holiday rental in Cudjoe Key

* OCEAN FRONT * Private 56' DOCK * 5 to 7 night min. ** MAXIMUM OCCUPANCY 4 **

2 bedrooms
2 bathrooms
Sleeps 6
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Opening available!! Sanitized and ready to go! New Central Air 7-2019, holiday rental in Cudjoe Key

Opening available!! Sanitized and ready to go! New Central Air 7-2019

2 bedrooms
1 bathroom
Sleeps 6
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Water Front Beautiful Home, holiday rental in Cudjoe Key

Water Front Beautiful Home

2 bedrooms
1 bathroom
Sleeps 4
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Cottage by the Sea 1BD/1BA  Boat Dockage Heated Pool, holiday rental in Cudjoe Key

Cottage by the Sea 1BD/1BA Boat Dockage Heated Pool

1 bedroom
1 bathroom
Sleeps 4
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5 O'Clock Somewhere, holiday rental in Cudjoe Key

5 O'Clock Somewhere

2 bedrooms
2 bathrooms
Sleeps 4
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REDUCED SPRING RATES!  Private Home in Waterfront Community Pool Kayaks Bikes, holiday rental in Cudjoe Key

REDUCED SPRING RATES! Private Home in Waterfront Community Pool Kayaks Bikes

2 bedrooms
3 bathrooms
Sleeps 6
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Cudjoe Cottage, holiday rental in Cudjoe Key

Cudjoe Cottage

2 bedrooms
2 bathrooms
Sleeps 4
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Island Therapy - Florida Keys, holiday rental in Cudjoe Key

Island Therapy - Florida Keys

2 bedrooms
2 bathrooms
Sleeps 6
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Paradise on Cudjoe Bay, holiday rental in Cudjoe Key

Paradise on Cudjoe Bay

2 bedrooms
3 bathrooms
Sleeps 6
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6 other travellers have booked this property
Magnificent Ocean view with 35' dock , Canal home in gated Venture Out Resort, holiday rental in Cudjoe Key

Magnificent Ocean view with 35' dock , Canal home in gated Venture Out Resort

2 bedrooms
2 bathrooms
Sleeps 6
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6 other travellers have booked this property
Home with Open Ocean,Spectacular Sunset views & Private Launch (28 day rentals), holiday rental in Cudjoe Key

Home with Open Ocean,Spectacular Sunset views & Private Launch (28 day rentals)

2 bedrooms
2 bathrooms
Sleeps 6
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Blue Palms Retreat. ocean front w/pool and dock for your boat., holiday rental in Cudjoe Key

Blue Palms Retreat. ocean front w/pool and dock for your boat.

3 bedrooms
2 bathrooms
Sleeps 8
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Waterside Bay, holiday rental in Cudjoe Key

Waterside Bay

3 bedrooms
3 bathrooms
Sleeps 6
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Catch of the Day!, holiday rental in Cudjoe Key

Catch of the Day!

2 bedrooms
2 bathrooms
Sleeps 6
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Hogfish  Retreat, holiday rental in Cudjoe Key

Hogfish Retreat

2 bedrooms
2 bathrooms
Sleeps 6
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Neptune's End Waterfront Retreat, holiday rental in Cudjoe Key

Neptune's End Waterfront Retreat

4 bedrooms
3 bathrooms
Sleeps 10
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Ocean Perch, Dock, Open Water Views, 80' Heated Pool, Tennis, 20 Min to Key West, holiday rental in Cudjoe Key

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

2 bedrooms
2 bathrooms
Sleeps 5
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Resort Waterfront Home, holiday rental in Cudjoe Key

Resort Waterfront Home

2 bedrooms
2 bathrooms
Sleeps 5
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Waterfront Relaxation and Barefoot Sunsets, holiday rental in Cudjoe Key

Waterfront Relaxation and Barefoot Sunsets

3 bedrooms
3 bathrooms
Sleeps 6
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Key Lime Cottage in Cudjoe Key, holiday rental in Cudjoe Key

Key Lime Cottage in Cudjoe Key

2 bedrooms
2 bathrooms
Sleeps 6
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BIG BLUE waits for you in the sunny Keys, holiday rental in Cudjoe Key

BIG BLUE waits for you in the sunny Keys

2 bedrooms
2 bathrooms
Sleeps 6
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WATERFRONT fresh & cozy 2 bedroom 35 sea wall New UV light air purification safe, holiday rental in Cudjoe Key

WATERFRONT fresh & cozy 2 bedroom 35 sea wall New UV light air purification safe

2 bedrooms
1 bathroom
Sleeps 6
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Dolphin House (#386) with beautiful open water views, holiday rental in Cudjoe Key

Dolphin House (#386) with beautiful open water views

2 bedrooms
2 bathrooms
Sleeps 4
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Relaxing and Inviting home in gated community, holiday rental in Cudjoe Key

Relaxing and Inviting home in gated community

2 bedrooms
1 bathroom
Sleeps 4
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MAGNIFICENT OCEAN VIEW w/35' of DOCKAGE!! Gated Resort with many activities., holiday rental in Cudjoe Key

MAGNIFICENT OCEAN VIEW w/35' of DOCKAGE!! Gated Resort with many activities.

2 bedrooms
2 bathrooms
Sleeps 6
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Venture Out - Waterfront Paradise   2/1, with  35' Dock and open water views!, holiday rental in Cudjoe Key

Venture Out - Waterfront Paradise 2/1, with 35' Dock and open water views!

2 bedrooms
1 bathroom
Sleeps 6
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“Key's Life' Ocean Views, Sunsets and Tropical Breezes Await You!!!”, holiday rental in Cudjoe Key

“Key's Life' Ocean Views, Sunsets and Tropical Breezes Await You!!!”

3 bedrooms
2 bathrooms
Sleeps 6
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Sparkling Clean & New Turn Key 1Bd/1Ba, holiday rental in Cudjoe Key

Sparkling Clean & New Turn Key 1Bd/1Ba

1 bedroom
1 bathroom
Sleeps 4
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Venture Out #465 2/2 Tropical Getaway on Canal with Open Water View, holiday rental in Cudjoe Key

Venture Out #465 2/2 Tropical Getaway on Canal with Open Water View

2 bedrooms
2 bathrooms
Sleeps 4
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Luxurious Oceanfront Home on Beach, Dock, Heat/Cool Pool, Kayaks, FirePit, Bikes, holiday rental in Cudjoe Key

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

2 bedrooms
3 bathrooms
Sleeps 6
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Brand new 4 bedroom 4 bath home with a beautiful pool and dock near Key West., holiday rental in Cudjoe Key

Brand new 4 bedroom 4 bath home with a beautiful pool and dock near Key West.

4 bedrooms
4 bathrooms
Sleeps 10
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Yellow vacation home, water view, boat dock, heated private pool., holiday rental in Cudjoe Key

Yellow vacation home, water view, boat dock, heated private pool.

3 bedrooms
2 bathrooms
Sleeps 6
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