Search Holiday Homes in Cudjoe Key

    price find illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Save instantly and earn perks with One Key
    Learn about One Key
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
15 Aug - 17 Aug
In two weeks
22 Aug - 24 Aug
In one month
5 Sept - 7 Sept
In two months
3 Oct - 5 Oct

Browse Select Cudjoe Key Holiday Homes

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
Dining

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
Pool

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
Fridge, microwave, oven, stovetop

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 £464
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
Property grounds

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 £537
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!
A heated 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!
Terrace/patio

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
Exterior

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
Beach nearby

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. "
The price is £552
includes taxes & fees
7 Aug - 8 Aug
Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West
Torchview Lookout- Secluded Waterfront Retreat With 240’ Dock On Niles Channel
Fridge, microwave, oven, stovetop

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

9.6 out of 10, Exceptional, (57)
"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!
Marina

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!
Marina

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!
Property grounds

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
Property grounds

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
Exterior

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
Marina

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!
Property grounds

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

8.8 out of 10, Excellent, (53)
"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, (93)
"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
Balcony

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 £415
includes taxes & fees
13 Aug - 14 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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Cudjoe Key Hotel Reviews

Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

10/10 Excellent
"I loved my experience"
Thamiris 1-night trip
Posted 23 hours ago
Blue Flamingo Resort Key West