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Cudjoe Key Vacation Rentals

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

Rental Home
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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**TIDEWATER VIEWS * VENTURE OUT** 2BR/2BA Cottage + 35’ Private Slip | 80’ Pool, vacation rental in Cudjoe Key
**TIDEWATER VIEWS * VENTURE OUT** 2BR/2BA Cottage + 35’ Private Slip | 80’ Pool, vacation rental in Cudjoe Key
**TIDEWATER VIEWS * VENTURE OUT** 2BR/2BA Cottage + 35’ Private Slip | 80’ Pool, vacation rental in Cudjoe Key

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

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Beautiful Family-Friendly home, Dock, Heated Pool, near Key West, MM21.5, vacation rental in Cudjoe Key
Beautiful Family-Friendly home, Dock, Heated Pool, near Key West, MM21.5, vacation rental in Cudjoe Key
Beautiful Family-Friendly home, Dock, Heated Pool, near Key West, MM21.5, vacation rental in Cudjoe Key

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

Rental Home
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Yellow Vacation home, Private heated Pool, boat dock. Tent sites., vacation rental in Cudjoe Key
Yellow Vacation home, Private heated Pool, boat dock. Tent sites., vacation rental in Cudjoe Key
Yellow Vacation home, Private heated Pool, boat dock. Tent sites., vacation rental in Cudjoe Key

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

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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White Vacation home, Private Boat Dockage, Heated Private Pool., vacation rental in Cudjoe Key
White Vacation home, Private Boat Dockage, Heated Private Pool., vacation rental in Cudjoe Key
White Vacation home, Private Boat Dockage, Heated Private Pool., vacation rental in Cudjoe Key

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

Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill, vacation rental in Cudjoe Key
Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill, vacation rental in Cudjoe Key
Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill, vacation rental in Cudjoe Key

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

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

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

Rental Home
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, vacation rental in Cudjoe Key
Keys Sanctuary In A  Gated Community With Dock And Pool  On Atlantic Ocean, vacation rental in Cudjoe Key
Keys Sanctuary In A  Gated Community With Dock And Pool  On Atlantic Ocean, vacation rental in Cudjoe Key

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

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

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

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

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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OCEAN PARADISE AT VENTURE OUT + 4 BIKES & 2-2 PERSON KAYAKS! KING & QUEEN BEDS!, vacation rental in Cudjoe Key
OCEAN PARADISE AT VENTURE OUT + 4 BIKES & 2-2 PERSON KAYAKS! KING & QUEEN BEDS!, vacation rental in Cudjoe Key
OCEAN PARADISE AT VENTURE OUT + 4 BIKES & 2-2 PERSON KAYAKS! KING & QUEEN BEDS!, vacation rental in Cudjoe Key

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

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

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

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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REDUCED SPRING RATES!  Private Home in Waterfront Community Pool Kayaks Bikes, vacation rental in Cudjoe Key
REDUCED SPRING RATES!  Private Home in Waterfront Community Pool Kayaks Bikes, vacation rental in Cudjoe Key
REDUCED SPRING RATES!  Private Home in Waterfront Community Pool Kayaks Bikes, vacation rental in Cudjoe Key

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

Rental Home
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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VO 173 2 Bed 2 Bath Silt Canal-Front, Ocean View, vacation rental in Cudjoe Key
VO 173 2 Bed 2 Bath Silt Canal-Front, Ocean View, vacation rental in Cudjoe Key
VO 173 2 Bed 2 Bath Silt Canal-Front, Ocean View, vacation rental in Cudjoe Key

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

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

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

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Waterfront 80' heated pool hottub Gorgeous views 20 mins to Key West & Marathon, vacation rental in Cudjoe Key
Waterfront 80' heated pool hottub Gorgeous views 20 mins to Key West & Marathon, vacation rental in Cudjoe Key
Waterfront 80' heated pool hottub Gorgeous views 20 mins to Key West & Marathon, vacation rental in Cudjoe Key

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

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Direct Ocean View! 5 Bed/3 Bath with room for everyone. Large pool and Dock!, vacation rental in Cudjoe Key
Direct Ocean View! 5 Bed/3 Bath with room for everyone. Large pool and Dock!, vacation rental in Cudjoe Key
Direct Ocean View! 5 Bed/3 Bath with room for everyone. Large pool and Dock!, vacation rental in Cudjoe Key

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

Rental Home
5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Crystal Clear Water Getaway!, vacation rental in Cudjoe Key
Crystal Clear Water Getaway!, vacation rental in Cudjoe Key
Crystal Clear Water Getaway!, vacation rental in Cudjoe Key

Crystal Clear Water Getaway!

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Ocean Perch, Dock, Open Water Views, 80' Heated Pool, Tennis, 20 Min to Key West, vacation rental in Cudjoe Key
Ocean Perch, Dock, Open Water Views, 80' Heated Pool, Tennis, 20 Min to Key West, vacation rental in Cudjoe Key
Ocean Perch, Dock, Open Water Views, 80' Heated Pool, Tennis, 20 Min to Key West, vacation rental in Cudjoe Key

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

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Ocean front with dock, heated pool, vacation rental in Cudjoe Key
Ocean front with dock, heated pool, vacation rental in Cudjoe Key
Ocean front with dock, heated pool, vacation rental in Cudjoe Key

Ocean front with dock, heated pool

Rental Home
6 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
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Oceanfront Home with Pool and Beach, vacation rental in Cudjoe Key
Oceanfront Home with Pool and Beach, vacation rental in Cudjoe Key
Oceanfront Home with Pool and Beach, vacation rental in Cudjoe Key

Oceanfront Home with Pool and Beach

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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LATITUDE ADJUSTMENT, vacation rental in Cudjoe Key
LATITUDE ADJUSTMENT, vacation rental in Cudjoe Key
LATITUDE ADJUSTMENT, vacation rental in Cudjoe Key

LATITUDE ADJUSTMENT

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

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Oceanfront Million $$ View, vacation rental in Cudjoe Key
Oceanfront Million $$ View, vacation rental in Cudjoe Key
Oceanfront Million $$ View, vacation rental in Cudjoe Key

Oceanfront Million $$ View

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Comfortable Waterfront Vacation Rental, vacation rental in Cudjoe Key
Comfortable Waterfront Vacation Rental, vacation rental in Cudjoe Key
Comfortable Waterfront Vacation Rental, vacation rental in Cudjoe Key

Comfortable Waterfront Vacation Rental

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Private Oceanfront Cottage with dockage, pool just minutes to Key West!, vacation rental in Cudjoe Key
Private Oceanfront Cottage with dockage, pool just minutes to Key West!, vacation rental in Cudjoe Key
Private Oceanfront Cottage with dockage, pool just minutes to Key West!, vacation rental in Cudjoe Key

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

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Opening available!! Sanitized and ready to go!, vacation rental in Cudjoe Key
Opening available!! Sanitized and ready to go!, vacation rental in Cudjoe Key
Opening available!! Sanitized and ready to go!, vacation rental in Cudjoe Key

Opening available!! Sanitized and ready to go!

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Relaxing and Inviting home in gated community, vacation rental in Cudjoe Key
Relaxing and Inviting home in gated community, vacation rental in Cudjoe Key
Relaxing and Inviting home in gated community, vacation rental in Cudjoe Key

Relaxing and Inviting home in gated community

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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WATERFRONT fresh & cozy 2 bedroom 35 sea wall
New UV light air purification safe, vacation rental in Cudjoe Key
WATERFRONT fresh & cozy 2 bedroom 35 sea wall
New UV light air purification safe, vacation rental in Cudjoe Key
WATERFRONT fresh & cozy 2 bedroom 35 sea wall
New UV light air purification safe, vacation rental in Cudjoe Key

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

Rental Home
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Sparkling Clean & New Turn Key 1Bd/1Ba, vacation rental in Cudjoe Key
Sparkling Clean & New Turn Key 1Bd/1Ba, vacation rental in Cudjoe Key
Sparkling Clean & New Turn Key 1Bd/1Ba, vacation rental in Cudjoe Key

Sparkling Clean & New Turn Key 1Bd/1Ba

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Fandango, vacation rental in Cudjoe Key
Fandango, vacation rental in Cudjoe Key
Fandango, vacation rental in Cudjoe Key

Fandango

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

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

Rental Home
3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Key Lime Cottage in Cudjoe Key, vacation rental in Cudjoe Key
Key Lime Cottage in Cudjoe Key, vacation rental in Cudjoe Key
Key Lime Cottage in Cudjoe Key, vacation rental in Cudjoe Key

Key Lime Cottage in Cudjoe Key

Rental Home
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Shangri-la in the Keys! Enjoy the water views and a 45' dock space!, vacation rental in Cudjoe Key
Shangri-la in the Keys! Enjoy the water views and a 45' dock space!, vacation rental in Cudjoe Key
Shangri-la in the Keys! Enjoy the water views and a 45' dock space!, vacation rental in Cudjoe Key

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

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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WALK TO THE BEACH! Upscale Designer 2Bd/2Ba in Venture Out a Gated Communi

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Tropical Paradise Oceanfront Home with Pool, vacation rental in Cudjoe Key
Tropical Paradise Oceanfront Home with Pool, vacation rental in Cudjoe Key
Tropical Paradise Oceanfront Home with Pool, vacation rental in Cudjoe Key

Tropical Paradise Oceanfront Home with Pool

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Best Value! Waterfront, High Speed Wi-Fi., vacation rental in Cudjoe Key
Best Value! Waterfront, High Speed Wi-Fi., vacation rental in Cudjoe Key
Best Value! Waterfront, High Speed Wi-Fi., vacation rental in Cudjoe Key

Best Value! Waterfront, High Speed Wi-Fi.

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Fishermen’s paradise � FLORIDA KEYS ARE NOW OPEN!

Rental Home
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, vacation rental in Cudjoe Key
Cute, Affordable Keys house in Venture Out gated community 19 miles from Key Wes, vacation rental in Cudjoe Key
Cute, Affordable Keys house in Venture Out gated community 19 miles from Key Wes, vacation rental in Cudjoe Key

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

Rental Home
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Dolphin House (#386) with beautiful open water views, vacation rental in Cudjoe Key
Dolphin House (#386) with beautiful open water views, vacation rental in Cudjoe Key
Dolphin House (#386) with beautiful open water views, vacation rental in Cudjoe Key

Dolphin House (#386) with beautiful open water views

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

Resort Waterfront Home

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Cudjoe Cottages, swimming pool, kayaks, 20 miles from Key West

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Direct Oceanfront - Atlantic Side - Dockage - Swimming Pool - Kayak, vacation rental in Cudjoe Key
Direct Oceanfront - Atlantic Side - Dockage - Swimming Pool - Kayak, vacation rental in Cudjoe Key
Direct Oceanfront - Atlantic Side - Dockage - Swimming Pool - Kayak, vacation rental in Cudjoe Key

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

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Beautiful Ocean view with 35' private seawall, 80' Heated Pool, Hottub, vacation rental in Cudjoe Key
Beautiful Ocean view with 35' private seawall, 80' Heated Pool, Hottub, vacation rental in Cudjoe Key
Beautiful Ocean view with 35' private seawall, 80' Heated Pool, Hottub, vacation rental in Cudjoe Key

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

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

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

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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WATERFRONT PARADISE AT VENTURE OUT+4 BIKES & 2-2 SEAT KAYAKS! KING & QUEEN BEDS

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Family Retreat-Ocean front home with private pool, vacation rental in Cudjoe Key
Family Retreat-Ocean front home with private pool, vacation rental in Cudjoe Key
Family Retreat-Ocean front home with private pool, vacation rental in Cudjoe Key

Family Retreat-Ocean front home with private pool

Rental Home
6 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
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Paradise Awaits, Stilt home on Canal for fisherman,or Rest and Relaxation, vacation rental in Cudjoe Key
Paradise Awaits, Stilt home on Canal for fisherman,or Rest and Relaxation, vacation rental in Cudjoe Key
Paradise Awaits, Stilt home on Canal for fisherman,or Rest and Relaxation, vacation rental in Cudjoe Key

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

Rental Home
1 bedroom
2 bathrooms
Sleeps 6
Match: Sleeps
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Ocean view home -Private launch & breath taking sunset views-min 28 day rentals, vacation rental in Cudjoe Key
Ocean view home -Private launch & breath taking sunset views-min 28 day rentals, vacation rental in Cudjoe Key
Ocean view home -Private launch & breath taking sunset views-min 28 day rentals, vacation rental in Cudjoe Key

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

Rental Home
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, vacation rental in Cudjoe Key
Stilt home on beautiful open water with multi-level decks and screened porch, vacation rental in Cudjoe Key
Stilt home on beautiful open water with multi-level decks and screened porch, vacation rental in Cudjoe Key

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

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Frequently Asked Questions about Cudjoe Key