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Cudjoe Key Holiday Apartments

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112 rentals in Cudjoe Key.
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Luxurious Oceanfront Home on Beach, Dock, Heat/Cool Pool, Kayaks, FirePit, Bikes

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
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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, holiday rental in Cudjoe Key
**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

Holiday Rental House
2 bedrooms
2 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, holiday rental in Cudjoe Key
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

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
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White Vacation home, Private Boat Dockage, Heated Private Pool., holiday rental in Cudjoe Key
White Vacation home, Private Boat Dockage, Heated Private Pool., holiday rental in Cudjoe Key
White Vacation home, Private Boat Dockage, Heated Private Pool., holiday rental in Cudjoe Key

White Vacation home, Private Boat Dockage, Heated Private Pool.

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Yellow Vacation home, Private heated Pool, boat dock. Tent sites., holiday rental in Cudjoe Key
Yellow Vacation home, Private heated Pool, boat dock. Tent sites., holiday rental in Cudjoe Key
Yellow Vacation home, Private heated Pool, boat dock. Tent sites., holiday rental in Cudjoe Key

Yellow Vacation home, Private heated Pool, boat dock. Tent sites.

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
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Luxury Home #111-Pool,Dock,Kayaks,Bikes,On Ocean near Key West,Free Trailer Keep, holiday rental in Cudjoe Key
Luxury Home #111-Pool,Dock,Kayaks,Bikes,On Ocean near Key West,Free Trailer Keep, holiday rental in Cudjoe Key
Luxury Home #111-Pool,Dock,Kayaks,Bikes,On Ocean near Key West,Free Trailer Keep, holiday rental in Cudjoe Key

Luxury Home #111-Pool,Dock,Kayaks,Bikes,On Ocean near Key West,Free Trailer Keep

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
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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, holiday rental in Cudjoe Key
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

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
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Luxury Home #109-Pool,Dock,Kayaks,Bikes,On Ocean near Key West,Free Trailer Keep, holiday rental in Cudjoe Key
Luxury Home #109-Pool,Dock,Kayaks,Bikes,On Ocean near Key West,Free Trailer Keep, holiday rental in Cudjoe Key
Luxury Home #109-Pool,Dock,Kayaks,Bikes,On Ocean near Key West,Free Trailer Keep, holiday rental in Cudjoe Key

Luxury Home #109-Pool,Dock,Kayaks,Bikes,On Ocean near Key West,Free Trailer Keep

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Keys Sanctuary In A  Gated Community With Dock And Pool  On Atlantic Ocean, holiday rental in Cudjoe Key
Keys Sanctuary In A  Gated Community With Dock And Pool  On Atlantic Ocean, holiday rental in Cudjoe Key
Keys Sanctuary In A  Gated Community With Dock And Pool  On Atlantic Ocean, holiday rental in Cudjoe Key

Keys Sanctuary In A Gated Community With Dock And Pool On Atlantic Ocean

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
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OCEAN FRONT: The Glass House

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
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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!, holiday rental in Cudjoe Key
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!

Holiday Rental House
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, holiday rental in Cudjoe Key
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

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Dock, Htd 80' Pool, Deep Channel, 15 Min To Key West, holiday rental in Cudjoe Key
Dock, Htd 80' Pool, Deep Channel, 15 Min To Key West, holiday rental in Cudjoe Key
Dock, Htd 80' Pool, Deep Channel, 15 Min To Key West, holiday rental in Cudjoe Key

Dock, Htd 80' Pool, Deep Channel, 15 Min To Key West

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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35' Seawall Sparkling , 30min from Keywest, WIFI, BBQ Grill, Pool, holiday rental in Cudjoe Key
35' Seawall Sparkling , 30min from Keywest, WIFI, BBQ Grill, Pool, holiday rental in Cudjoe Key
35' Seawall Sparkling , 30min from Keywest, WIFI, BBQ Grill, Pool, holiday rental in Cudjoe Key

35' Seawall Sparkling , 30min from Keywest, WIFI, BBQ Grill, Pool

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
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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, holiday rental in Cudjoe Key
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

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

Crystal Clear Water Getaway!

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Waterfront 80' heated pool hottub Gorgeous views 20 mins to Key West & Marathon, holiday rental in Cudjoe Key
Waterfront 80' heated pool hottub Gorgeous views 20 mins to Key West & Marathon, holiday rental in Cudjoe Key
Waterfront 80' heated pool hottub Gorgeous views 20 mins to Key West & Marathon, holiday rental in Cudjoe Key

Waterfront 80' heated pool hottub Gorgeous views 20 mins to Key West & Marathon

Holiday Rental House
2 bedrooms
2 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, holiday rental in Cudjoe Key
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

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Direct Ocean View! 5 Bed/3 Bath with room for everyone. Large pool and Dock!, holiday rental in Cudjoe Key
Direct Ocean View! 5 Bed/3 Bath with room for everyone. Large pool and Dock!, holiday rental in Cudjoe Key
Direct Ocean View! 5 Bed/3 Bath with room for everyone. Large pool and Dock!, holiday rental in Cudjoe Key

Direct Ocean View! 5 Bed/3 Bath with room for everyone. Large pool and Dock!

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Ocean front with dock, heated pool, holiday rental in Cudjoe Key
Ocean front with dock, heated pool, holiday rental in Cudjoe Key
Ocean front with dock, heated pool, holiday rental in Cudjoe Key

Ocean front with dock, heated pool

Holiday Rental House
6 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
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Oceanfront Million $$ View, holiday rental in Cudjoe Key
Oceanfront Million $$ View, holiday rental in Cudjoe Key
Oceanfront Million $$ View, holiday rental in Cudjoe Key

Oceanfront Million $$ View

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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LATITUDE ADJUSTMENT, holiday rental in Cudjoe Key
LATITUDE ADJUSTMENT, holiday rental in Cudjoe Key
LATITUDE ADJUSTMENT, holiday rental in Cudjoe Key

LATITUDE ADJUSTMENT

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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BIG BLUE waits for you in the sunny Keys

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Opening available!! Sanitized and ready to go!, holiday rental in Cudjoe Key
Opening available!! Sanitized and ready to go!, holiday rental in Cudjoe Key
Opening available!! Sanitized and ready to go!, holiday rental in Cudjoe Key

Opening available!! Sanitized and ready to go!

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Private Oceanfront Cottage with dockage, pool just minutes to Key West!, holiday rental in Cudjoe Key
Private Oceanfront Cottage with dockage, pool just minutes to Key West!, holiday rental in Cudjoe Key
Private Oceanfront Cottage with dockage, pool just minutes to Key West!, holiday rental in Cudjoe Key

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

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Relaxing and Inviting home in gated community, holiday rental in Cudjoe Key
Relaxing and Inviting home in gated community, holiday rental in Cudjoe Key
Relaxing and Inviting home in gated community, holiday rental in Cudjoe Key

Relaxing and Inviting home in gated community

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Oceanfront Home with Pool and Beach, holiday rental in Cudjoe Key
Oceanfront Home with Pool and Beach, holiday rental in Cudjoe Key
Oceanfront Home with Pool and Beach, holiday rental in Cudjoe Key

Oceanfront Home with Pool and Beach

Holiday Rental House
3 bedrooms
3 bathrooms
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, holiday rental in Cudjoe Key
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

Holiday Rental House
2 bedrooms
1 bathroom
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, holiday rental in Cudjoe Key
Sparkling Clean & New Turn Key 1Bd/1Ba, holiday rental in Cudjoe Key

Sparkling Clean & New Turn Key 1Bd/1Ba

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Fandango, holiday rental in Cudjoe Key
Fandango, holiday rental in Cudjoe Key
Fandango, holiday rental in Cudjoe Key

Fandango

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
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Canal Front, Spa/Pool, 2 Kayaks, 3 Bed, 2 Bath, Oceanside Home, holiday rental in Cudjoe Key
Canal Front, Spa/Pool, 2 Kayaks, 3 Bed, 2 Bath, Oceanside Home, holiday rental in Cudjoe Key
Canal Front, Spa/Pool, 2 Kayaks, 3 Bed, 2 Bath, Oceanside Home, holiday rental in Cudjoe Key

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

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Comfortable Waterfront Vacation Rental, holiday rental in Cudjoe Key
Comfortable Waterfront Vacation Rental, holiday rental in Cudjoe Key
Comfortable Waterfront Vacation Rental, holiday rental in Cudjoe Key

Comfortable Waterfront Vacation Rental

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Tropical Paradise Oceanfront Home with Pool, holiday rental in Cudjoe Key
Tropical Paradise Oceanfront Home with Pool, holiday rental in Cudjoe Key
Tropical Paradise Oceanfront Home with Pool, holiday rental in Cudjoe Key

Tropical Paradise Oceanfront Home with Pool

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
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Key Lime Cottage in Cudjoe Key, holiday rental in Cudjoe Key
Key Lime Cottage in Cudjoe Key, holiday rental in Cudjoe Key
Key Lime Cottage in Cudjoe Key, holiday rental in Cudjoe Key

Key Lime Cottage in Cudjoe Key

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Fishermen’s paradise � FLORIDA KEYS ARE NOW OPEN!

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Cute, Affordable Keys house in Venture Out gated community 19 miles from Key Wes, holiday rental in Cudjoe Key
Cute, Affordable Keys house in Venture Out gated community 19 miles from Key Wes, holiday rental in Cudjoe Key
Cute, Affordable Keys house in Venture Out gated community 19 miles from Key Wes, holiday rental in Cudjoe Key

Cute, Affordable Keys house in Venture Out gated community 19 miles from Key Wes

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Resort Waterfront Home, holiday rental in Cudjoe Key
Resort Waterfront Home, holiday rental in Cudjoe Key
Resort Waterfront Home, holiday rental in Cudjoe Key

Resort Waterfront Home

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
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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!, holiday rental in Cudjoe Key
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!

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Cudjoe Cottages, swimming pool, kayaks, 20 miles from Key West

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
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WALK TO THE BEACH! Upscale Designer 2Bd/2Ba in Venture Out a Gated Communi

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
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WATERFRONT PARADISE AT VENTURE OUT+4 BIKES & 2-2 SEAT KAYAKS! KING & QUEEN BEDS

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

Dolphin House (#386) with beautiful open water views

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
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Beautiful Ocean view with 35' private seawall, 80' Heated Pool, Hottub, holiday rental in Cudjoe Key
Beautiful Ocean view with 35' private seawall, 80' Heated Pool, Hottub, holiday rental in Cudjoe Key
Beautiful Ocean view with 35' private seawall, 80' Heated Pool, Hottub, holiday rental in Cudjoe Key

Beautiful Ocean view with 35' private seawall, 80' Heated Pool, Hottub

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

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

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Best Value! Waterfront, High Speed Wi-Fi., holiday rental in Cudjoe Key
Best Value! Waterfront, High Speed Wi-Fi., holiday rental in Cudjoe Key
Best Value! Waterfront, High Speed Wi-Fi., holiday rental in Cudjoe Key

Best Value! Waterfront, High Speed Wi-Fi.

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
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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, holiday rental in Cudjoe Key
Family Retreat-Ocean front home with private pool, holiday rental in Cudjoe Key

Family Retreat-Ocean front home with private pool

Holiday Rental House
6 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
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Family Friendly 2 Bedroom 1 Bath, 32' Seawall, 4 Bikes, 3 Kayaks, WiFi, 2 TV', holiday rental in Cudjoe Key
Family Friendly 2 Bedroom 1 Bath, 32' Seawall, 4 Bikes, 3 Kayaks, WiFi, 2 TV', holiday rental in Cudjoe Key
Family Friendly 2 Bedroom 1 Bath, 32' Seawall, 4 Bikes, 3 Kayaks, WiFi, 2 TV', holiday rental in Cudjoe Key

Family Friendly 2 Bedroom 1 Bath, 32' Seawall, 4 Bikes, 3 Kayaks, WiFi, 2 TV'

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Ocean view home -Private launch & breath taking sunset views-min 28 day rentals, holiday rental in Cudjoe Key
Ocean view home -Private launch & breath taking sunset views-min 28 day rentals, holiday rental in Cudjoe Key
Ocean view home -Private launch & breath taking sunset views-min 28 day rentals, holiday rental in Cudjoe Key

Ocean view home -Private launch & breath taking sunset views-min 28 day rentals

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Stilt home on beautiful open water with multi-level decks and screened porch, holiday rental in Cudjoe Key
Stilt home on beautiful open water with multi-level decks and screened porch, holiday rental in Cudjoe Key
Stilt home on beautiful open water with multi-level decks and screened porch, holiday rental in Cudjoe Key

Stilt home on beautiful open water with multi-level decks and screened porch

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Cottage with Pool and Dockage, just minutes to Key West, holiday rental in Cudjoe Key
Cottage with Pool and Dockage, just minutes to Key West, holiday rental in Cudjoe Key
Cottage with Pool and Dockage, just minutes to Key West, holiday rental in Cudjoe Key

Cottage with Pool and Dockage, just minutes to Key West

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Frequently Asked Questions about Cudjoe Key