Holiday Homes in Cudjoe Key

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Check prices for these dates

Next weekend
8 Aug - 10 Aug
In two weeks
15 Aug - 17 Aug
In one month
29 Aug - 31 Aug
In two months
26 Sept - 28 Sept

Featured Holiday Homes in Cudjoe Key

JUDY'S PLACE ~ 2 Bedroom, 1 Bathroom Home in Venture Out Community!
Pool

JUDY'S PLACE ~ 2 Bedroom, 1 Bathroom Home in Venture Out Community!

10.0 out of 10, Exceptional, (3)
"The place was just as pictured, very comfortable and private. Very clean and spacious. The only issue we had was trying to get the back door to lock. "
JUDY'S PLACE ~ 2 Bedroom, 1 Bathroom Home in Venture Out Community!
Waterfront luxury home with private pool
Relax in a spacious living area with a dining table, sofa, and comfortable seating.

Waterfront luxury home with private pool

9.8 out of 10, Exceptional, (78)
"We had a wonderful stay at 3/4 time! It is a beautiful VRBO to use in Key West. We truly appreciated all the thoughtful touches that made the place feel like a home away from home.The location was perfect, and the space was clean, comfortable, and well-equipped for a relaxing getaway. We absolueltly loved the heated pool. It was the perfect base for exploring Key West, and we’re already looking forward to our next visit."
Waterfront luxury home with private pool
Tropical Key West out of the way
Relax in a serene pool area surrounded by lush greenery and palm trees, complete with lounge chairs and umbrellas.

Tropical Key West out of the way

9.4 out of 10, Exceptional, (172)
"Thanks for the stay, we loved the pool and peaceful quiet while still being so close to everything. Family dinners on the porch were also a great and relaxing alternative to every meal out. "
Tropical Key West out of the way
Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West
Enjoy cooking and dining in this well-equipped kitchen with a central island, oven, and ample counter space.

Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West

9.0 out of 10, Wonderful, (151)
"The place was spacious, very clean and beautiful!"
The price is AU$941
includes taxes & fees
10 Aug - 11 Aug
Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West
Old Florida Style, wrap around porch, boat basin for dockage, open water
Relax on the waterfront with Adirondack chairs and a small dining table.

Old Florida Style, wrap around porch, boat basin for dockage, open water

9.6 out of 10, Exceptional, (77)
"Very nice place to stay. Quick and efficient communication with host! Seemless check in and check out process. "
The price is AU$1,090
includes taxes & fees
18 Aug - 19 Aug
Old Florida Style, wrap around porch, boat basin for dockage, open water
CORAL CABANA ~ Lush Porch Views of the Pool & Gardens, near Golf Course!
Dining

CORAL CABANA ~ Lush Porch Views of the Pool & Gardens, near Golf Course!

9.8 out of 10, Exceptional, (136)
"Property was clean and comfortable with everything we needed. Only complaint is the late check in time."
CORAL CABANA ~ Lush Porch Views of the Pool & Gardens, near Golf Course!
Oceanview home with private pool & lush landscaping!
Relax in a serene outdoor oasis with a patio, wicker lounge chairs, and a refreshing pool.

Oceanview home with private pool & lush landscaping!

9.8 out of 10, Exceptional, (111)
"Great place to stay very kid friendly and a short golfcart ride to everything "
Oceanview home with private pool & lush landscaping!
HAVANA DAYDREAMING ~ Waterfront 1 BR/1 Ba w/ Dockage & Hot Tub!
Relax on the deck with a hot tub and tranquil views of the water.

HAVANA DAYDREAMING ~ Waterfront 1 BR/1 Ba w/ Dockage & Hot Tub!

9.6 out of 10, Exceptional, (42)
"Very nice retreat on the water. Enjoyed our views from the porch."
HAVANA DAYDREAMING ~ Waterfront 1 BR/1 Ba w/ Dockage & Hot Tub!
Oceanside Paradise: Kayaks, Free WiFi, A/C, Grill, Elevated Deck, 24hr Security
Enjoy ocean views from the spacious balcony and covered porch of this coastal retreat.

Oceanside Paradise: Kayaks, Free WiFi, A/C, Grill, Elevated Deck, 24hr Security

9.8 out of 10, Exceptional, (250)
"Home was clean and great location! Would definitely stay here again! "
Oceanside Paradise: Kayaks, Free WiFi, A/C, Grill, Elevated Deck, 24hr Security
Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West
Enjoy a serene beach experience with a clear ocean view, lounge chairs, and a dock for water activities.

Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West

8.8 out of 10, Excellent, (85)
"Property was adequate but could use a few updates. The location was great. Easy to get to Key West near good local restaurants and beaches. Would stay again. "
Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West
Torchview Lookout- Secluded Waterfront Retreat With 240’ Dock On Niles Channel
Enjoy cooking in this well-equipped kitchen with a central island and standard appliances.

Torchview Lookout- Secluded Waterfront Retreat With 240’ Dock On Niles Channel

9.6 out of 10, Exceptional, (56)
"It was a beautiful home and Francine, our host, was most accommodating."
Torchview Lookout- Secluded Waterfront Retreat With 240’ Dock On Niles Channel
3-Story spacious conch style home w/ private pool & dock!
Walk along the pier and enjoy the scenic views of the surrounding water.

3-Story spacious conch style home w/ private pool & dock!

9.8 out of 10, Exceptional, (131)
"We had a wonderful stay in Key West and this house was great for everything we needed!"
3-Story spacious conch style home w/ private pool & dock!
Luxury Waterfront Home with Private Pool and Dock!
Stroll along the waterfront pier, taking in the serene views of the calm waters.

Luxury Waterfront Home with Private Pool and Dock!

9.8 out of 10, Exceptional, (81)
"Great place and location. Nice and quiet but not far from the action. Pics don’t really do it justice. Would definitely return "
Luxury Waterfront Home with Private Pool and Dock!
Waterfront Luxury Home with private pool!
Relax in a serene outdoor space with a deck, pool, and comfortable seating areas surrounded by lush greenery.

Waterfront Luxury Home with private pool!

9.4 out of 10, Exceptional, (75)
"What a beautiful home and an amazing stay!! We had a fantastic time! (Missing the helicopter pad and private dock though) haha just a joke from the guest book!! It was PERFECT!!!"
Waterfront Luxury Home with private pool!
Casa Capri Beautiful Tropical with 3 King Suites - 2 miles to beach
Escape to a serene tropical oasis with lush gardens and a charming two-story building.

Casa Capri Beautiful Tropical with 3 King Suites - 2 miles to beach

10.0 out of 10, Exceptional, (236)
"Great property with easy access to everything. "
Casa Capri Beautiful Tropical with 3 King Suites - 2 miles to beach
20 MINUTES TO KEY WEST , BOATERS PARADISE
Enjoy waterfront views and access to a marina from this coastal property.

20 MINUTES TO KEY WEST , BOATERS PARADISE

9.4 out of 10, Exceptional, (57)
"Great little spot, location was perfect, house was cozy, and the host was fantastic! The staff at Venture Out were also extremely courteous. Would definitely stay here again. "
20 MINUTES TO KEY WEST , BOATERS PARADISE
Big Pine Key Unique Direct Ocean Access with 10K lbs private dock boat lift
Boats dock at the marina, offering a serene waterfront view.

Big Pine Key Unique Direct Ocean Access with 10K lbs private dock boat lift

9.4 out of 10, Exceptional, (8)
"We had a wonderful holiday vacation. Thank you Kelly and Walter for sharing your vacation rental with our family."
Big Pine Key Unique Direct Ocean Access with 10K lbs private dock boat lift
ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub!
Relax on a lakeside deck with a thatched-roof structure nearby, perfect for a serene escape.

ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub!

8.8 out of 10, Excellent, (52)
"Peaceful and paradise!"
ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub!
Private Secluded Ocean View & Pool Near Key West
Outdoor pool, a heated pool

Private Secluded Ocean View & Pool Near Key West

8.2 out of 10, Very good, (92)
"Everything was exactly as described, the host was gracious and communicative, the house is great for a large group and a quiet location"
Private Secluded Ocean View & Pool Near Key West
Just 20 miles from Key West! Oceanfront, dockage, swimming pool
Guests can enjoy a serene waterfront experience from this tranquil dock surrounded by lush greenery.

Just 20 miles from Key West! Oceanfront, dockage, swimming pool

8.4 out of 10, Very good, (114)
"Deer in the front yard, perfect location, clean and friendly "
The price is AU$842
includes taxes & fees
4 Aug - 5 Aug
Just 20 miles from Key West! Oceanfront, dockage, swimming pool
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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