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Holiday Homes in Cudjoe Key

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82 rentals in Cudjoe Key.
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Opening available!! Sanitized and ready to go!, holiday rental in Cudjoe Key

Opening available!! Sanitized and ready to go!

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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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
Match: Sleeps
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Paradise awaits you at Blue Moon!, holiday rental in Cudjoe Key

Paradise awaits you at Blue Moon!

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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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
Match: Sleeps
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**TIDEWATER VIEWS * VENTURE OUT** 2BR/2BA Cottage + 35’ Private Slip | 80’ Pool, holiday rental in Cudjoe Key

**TIDEWATER VIEWS * VENTURE OUT** 2BR/2BA Cottage + 35’ Private Slip | 80’ Pool

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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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
Match: Sleeps
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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
Match: Sleeps
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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
Match: Sleeps
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Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill, holiday rental in Cudjoe Key

Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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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
Match: Sleeps
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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
Match: Sleeps
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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
Match: Sleeps
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Crystal Clear Water Getaway!, holiday rental in Cudjoe Key

Crystal Clear Water Getaway!

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Tropical Getaway in a Fisherman's paradise, holiday rental in Cudjoe Key

Tropical Getaway in a Fisherman's paradise

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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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
Match: Sleeps
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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
Match: Sleeps
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OCEAN PARADISE AT VENTURE OUT + 4 BIKES & 2-2 PERSON KAYAKS! KING & QUEEN BEDS!, holiday rental in Cudjoe Key

OCEAN PARADISE AT VENTURE OUT + 4 BIKES & 2-2 PERSON KAYAKS! KING & QUEEN BEDS!

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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OCEAN FRONT: The Glass House, holiday rental in Cudjoe Key

OCEAN FRONT: The Glass House

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Peaceful and Ocean View Estate 15 minutes from Key West, holiday rental in Cudjoe Key

Peaceful and Ocean View Estate 15 minutes from Key West

4 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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VO 173 2 Bed 2 Bath Silt Canal-Front, Ocean View, holiday rental in Cudjoe Key

VO 173 2 Bed 2 Bath Silt Canal-Front, Ocean View

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Fandango, holiday rental in Cudjoe Key

Fandango

5 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
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Paradise Awaits, Stilt home on Canal for fisherman,or Rest and Relaxation, holiday rental in Cudjoe Key

Paradise Awaits, Stilt home on Canal for fisherman,or Rest and Relaxation

1 bedroom
2 bathrooms
Sleeps 6
Match: Sleeps
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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
Match: Sleeps
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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
Match: Sleeps
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Comfortable Waterfront Vacation Rental, holiday rental in Cudjoe Key

Comfortable Waterfront Vacation Rental

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Island Retreat With  35 Foot  Dock, holiday rental in Cudjoe Key

Island Retreat With 35 Foot Dock

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Shangri-la in the Keys! Enjoy the water views and a 45' dock space!, holiday rental in Cudjoe Key

Shangri-la in the Keys! Enjoy the water views and a 45' dock space!

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Lovely Furnished Home in Oceanfront Community w/Shared Boat Docks, Pool & Beac, holiday rental in Cudjoe Key

Lovely Furnished Home in Oceanfront Community w/Shared Boat Docks, Pool & Beac

2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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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
Match: Sleeps
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We know you need a vacation after this year!, holiday rental in Cudjoe Key

We know you need a vacation after this year!

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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LATITUDE ADJUSTMENT, holiday rental in Cudjoe Key

LATITUDE ADJUSTMENT

2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Resort Waterfront Home, holiday rental in Cudjoe Key

Resort Waterfront Home

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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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
Match: Sleeps
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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
Match: Sleeps
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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
Match: Sleeps
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PALM TREE PARADISE AT VENTURE OUT+ 4 BIKES, 2 KAYAKS, PATIO, QUEEN & FULL BEDS!, holiday rental in Cudjoe Key

PALM TREE PARADISE AT VENTURE OUT+ 4 BIKES, 2 KAYAKS, PATIO, QUEEN & FULL BEDS!

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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OCEANVIEW PARADISE AT VENTURE OUT+4 BIKES & 2-2 SEAT KAYAKS! KING & QUEEN BEDS!, holiday rental in Cudjoe Key

OCEANVIEW PARADISE AT VENTURE OUT+4 BIKES & 2-2 SEAT KAYAKS! KING & QUEEN BEDS!

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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WALK TO THE BEACH! Upscale Designer  2Bd/2Ba in Venture Out a Gated Communi, holiday rental in Cudjoe Key

WALK TO THE BEACH! Upscale Designer 2Bd/2Ba in Venture Out a Gated Communi

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Book Your Keys Getaway!!, holiday rental in Cudjoe Key

Book Your Keys Getaway!!

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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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
Match: Sleeps
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Night jasmine oceanfront vacation house, holiday rental in Cudjoe Key

Night jasmine oceanfront vacation house

4 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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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
Match: Sleeps
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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
Match: Sleeps
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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
Match: Sleeps
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Oceanfront home-swimming pool-boat ramp-dockage-just 20 miles from Key West, holiday rental in Cudjoe Key

Oceanfront home-swimming pool-boat ramp-dockage-just 20 miles from Key West

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Dog-friendly resort community home w/ shared pool, hot tub, & tennis court!, holiday rental in Cudjoe Key

Dog-friendly resort community home w/ shared pool, hot tub, & tennis court!

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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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
Match: Sleeps
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Paradise in the Keys close to oceanfront pool with 35' seawall, holiday rental in Cudjoe Key

Paradise in the Keys close to oceanfront pool with 35' seawall

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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CUDJOE KEY BOATER’S PARADISE ON THE WATER CLOSE TO KEY WEST - 22915 Bluegill Ln, holiday rental in Cudjoe Key

CUDJOE KEY BOATER’S PARADISE ON THE WATER CLOSE TO KEY WEST - 22915 Bluegill Ln

3 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Frequently Asked Questions about Cudjoe Key