Holiday Homes in Cudjoe Key

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Featured Holiday Homes in Cudjoe Key and around

INCOMMUNICADO ~ Waterfront 2 BR/2 Ba w/ Dockage and Hot Tub!
Property grounds
INCOMMUNICADO ~ Waterfront 2 BR/2 Ba w/ Dockage and Hot Tub!
9.4 out of 10, Exceptional, (15)
"Nice, clean property with new appliances. Convenient to Key West. Great deck for hanging out in the morning with coffee or with a cocktail in the evening. Hogfish Bar, a great sandwich shop and French bakery all close and convenient to the property."
INCOMMUNICADO ~ Waterfront 2 BR/2 Ba w/ Dockage and Hot Tub!
OFF CALL ~ Rustic, Nautical Decor With King Primary Suite & Heated Pool!
A heated pool
OFF CALL ~ Rustic, Nautical Decor With King Primary Suite & Heated Pool!
9.6 out of 10, Exceptional, (64)
"Enjoyed our stay…..Dan was very helpful with the smart tv issue…."
OFF CALL ~ Rustic, Nautical Decor With King Primary Suite & Heated Pool!
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, (18)
"Good location as far walking distance to a Cuban food truck- Luna. Hogfish is a good restaurant, good seafood and good service, short walk. Property was clean. Beds comfortable. Mostly quiet. It’s about 3 miles from Key West."
ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub!
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
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
9.8 out of 10, Exceptional, (47)
"So glad we found this location. Nice and peaceful but close to anything we needed. Sitting on the porch was so relaxing, watching boats go by. The house was very comfortable. Only wish the 2nd bedroom had a working TV. Our host was quick to answer any issue we had and left some great suggestions on places to eat. I would definitely return to enjoy this beautiful location"
Old Florida Style, wrap around porch, boat basin for dockage, open water
Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill
A heated pool
Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill
9.8 out of 10, Exceptional, (187)
"Very cute house! I didn't want to leave. Had plenty of everything. I definitely will stay there again. I have recommennded this house to several people after returning from our trip. The house had really nice & big washer & dryer. Was nice to come home with a suitcase of clean clothes rather than a hamper of dirty clothes. I took my teenager son & his friend & they enjoyed the bikes & kayaks. They also made friends with a couple other teenagers at the pool the first night we were there. Pool is...
Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill
**PLANTATION TROPICALE @ CASA EAST** Grand Estate & Pool + LAST KEY SERVICES…
Property grounds
**PLANTATION TROPICALE @ CASA EAST** Grand Estate & Pool + LAST KEY SERVICES…
10.0 out of 10, Exceptional, (34)
"We traveled from Michigan celebrating my mother’s 75th birthday. I don’t know much about the company last key rentals. The concierge, Victor and awesome person and awesome man very knowledgeable. Very pleasant made me and my family feel right at home. To last key Victor went above and beyond to answer any questions and to make everyone feel as comfortable and was very supportive and knowledgeable of the community and surrounding areas. To the owner you have amazing property."
**PLANTATION TROPICALE @ CASA EAST** Grand Estate & Pool + LAST KEY SERVICES…
CASA DE VINO ~ Amazing Price for Charming Townhouse with Pool & Tiki!
Outdoor dining
CASA DE VINO ~ Amazing Price for Charming Townhouse with Pool & Tiki!
9.8 out of 10, Exceptional, (70)
"Condo was lovely. Plenty of room for all of us and enjoyed the outdoor porches. Pool was great, too. Fun watching the roosters/hens/baby chicks and the iguanas and lizards! Area was good -- some walking distance restaurants (Roostica, Hogfish Bar & Grill), very good Cuban coffee truck. Easy uber ride into Duval St. area."
CASA DE VINO ~ Amazing Price for Charming Townhouse with Pool & Tiki!
NEWLY REMODELED KITCHEN!! PET FRIENDLY! 3 Bedroom 3 bathroom home. Sleeps 8
Pool
NEWLY REMODELED KITCHEN!! PET FRIENDLY! 3 Bedroom 3 bathroom home. Sleeps 8
9.6 out of 10, Exceptional, (187)
"We were disappointed that paying over $600 per night and there wasn't even any soap in the bathrooms. If you were to put any money into the house, i would suggest energy and sound proof windows as you can hear everything that goes down US1"
NEWLY REMODELED KITCHEN!! PET FRIENDLY! 3 Bedroom 3 bathroom home. Sleeps 8
Paris Mango: Waterfront Luxury Home with Ocean View & Heated Private Pool!
Beach
Paris Mango: Waterfront Luxury Home with Ocean View & Heated Private Pool!
9.6 out of 10, Exceptional, (73)
"Would book again if visiting Key West"
Paris Mango: Waterfront Luxury Home with Ocean View & Heated Private Pool!
CORAL CABANA ~ Lush Porch Views of the Pool & Gardens, near Golf Course!
A heated pool
CORAL CABANA ~ Lush Porch Views of the Pool & Gardens, near Golf Course!
9.8 out of 10, Exceptional, (97)
"Really enjoyed the stay. House was very clean. Only negative was the maintenance of the pool area coupd have been much better"
CORAL CABANA ~ Lush Porch Views of the Pool & Gardens, near Golf Course!
LICENSE TO CHILL ~ Waterfront 2 BR/2Ba in Cudjoe Key w/ Dockage & Parking!
Property grounds
LICENSE TO CHILL ~ Waterfront 2 BR/2Ba in Cudjoe Key w/ Dockage & Parking!
9.6 out of 10, Exceptional, (13)
"Annual family trip to the keys, a little fishing, a little snorkeling, some sailing……this place is soo convenient for all. Right on the water, close to everything. Second time we’ve stayed in this house. Will definitely return. Kudos to Dan and Wendy, made everything so easy. Thank you!!"
LICENSE TO CHILL ~ Waterfront 2 BR/2Ba in Cudjoe Key w/ Dockage & Parking!
Poolside Cottage #411
Outdoor dining
Poolside Cottage #411
10.0 out of 10, Exceptional, (17)
"Clean. Everything we needed in a key west stay."
The price is €344
includes taxes & fees
12 Jun - 13 Jun
Poolside Cottage #411
Cozy, Perfect Conch Cottage!
Pool
Cozy, Perfect Conch Cottage!
9.0 out of 10, Wonderful, (30)
"Our stay was great! The description is accurate. We enjoyed our 6 Mid-March days at "Cozy Perfect Conch Cottage." Yes, it's technically camping, but it's very NICE camping...in a campground...but a very NICE campground. The bed we used (there were only 2 of us) was super comfortable. The WiFi worked great. It was awesome having a full kitchen and washer/dryer. The towels were plentiful, soft and luxurious. Linens were also very soft and comfortable. Everything needed for basic cooking was...
Cozy, Perfect Conch Cottage!
Banana Breeze: Oceanview 4-bedroom home with private pool & lush landscaping!
Property grounds
Banana Breeze: Oceanview 4-bedroom home with private pool & lush landscaping!
9.8 out of 10, Exceptional, (80)
"This house was amazing. It's located close to the things we wanted to do in Key West without being in the middle of the chaos. We loved it."
Banana Breeze: Oceanview 4-bedroom home with private pool & lush landscaping!
Poolside Cottage #412
Outdoor dining
Poolside Cottage #412
10.0 out of 10, Exceptional, (6)
"Perfect location. Poolside. Friendly staff, excellent service ~ Brandy!!!"
The price is €345
includes taxes & fees
12 Jun - 13 Jun
Poolside Cottage #412
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, (90)
"Explain to people that there is an opportunity to park the truck with a trailer and that there are ramps for the boat because I myself did not take my boat thinking that there was nothing like that. Thanks "
Just 20 miles from Key West! Oceanfront, dockage, swimming pool
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, (217)
"My daughter and I stayed in Cudjoe Key to be close to Key West. The location was good. The unit had everything we needed both inside and out. We grilled and cooked which was great. The beds were comfortable. Unfortunately, the weather did not cooperate and excursions were cancelled so we spent more time in Key West than we had planned. But the unit had lots of games and the TV had the tennis channel which was very nice. All in all, it was a good time."
Oceanside Paradise: Kayaks, Free WiFi, A/C, Grill, Elevated Deck, 24hr Security
Casa Cay West Beautiful Tropical House 3 bedrooms 2 KING suites POOL 2 mi beach
Outdoor pool, a heated pool
Casa Cay West Beautiful Tropical House 3 bedrooms 2 KING suites POOL 2 mi beach
10.0 out of 10, Exceptional, (388)
"We loved our stay at Judy’s place. It’s a short drive into downtown key west. We rented a car and took Ubers, which were readily available. The house was exactly as described and so nicely decorated. Had everything you need, including plenty of towels for bath and pool. Pool was very clean and relaxing. The house feels very private with all of the landscaping. Across the street is a great brewery, coffee shop and pizza/Italian restaurant. Judy was so helpful and responsive. Highly recommend to...
Casa Cay West Beautiful Tropical House 3 bedrooms 2 KING suites POOL 2 mi beach
Seagate House by Brightwild | Waterfront w/Dock
Aerial view
Seagate House by Brightwild | Waterfront w/Dock
10.0 out of 10, Exceptional, (9)
"Overall the house was at a perfect distance from the main attractions, yet it’s a quiet gated neighborhood. A perfect place to have the whole family and friends gatherings and have a good time."
The price is €1,521
includes taxes & fees
17 Jun - 18 Jun
Seagate House by Brightwild | Waterfront w/Dock
New! Crestwood House by Brightwild | Huge Pool
Fridge, microwave, oven, stovetop
New! Crestwood House by Brightwild | Huge Pool
The price is €1,834
includes taxes & fees
16 Jun - 17 Jun
New! Crestwood House by Brightwild | Huge Pool
Don't see what you're looking for?
See all available properties in Cudjoe Key
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.

Other property types in Cudjoe Key

Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes
Property grounds
Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes
9.8 out of 10, Exceptional, (204)
"Beautiful and quiet location. Close to Key West yet just far enough to be away from the crowds. Family thoroughly enjoyed it. Everything is as pictured and immaculately clean, truly a gem. Melanie was friendly, always available and always responsive."
The price is €418
includes taxes & fees
18 Jun - 19 Jun
Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes
Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill
A heated pool
Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill
9.8 out of 10, Exceptional, (187)
"Very cute house! I didn't want to leave. Had plenty of everything. I definitely will stay there again. I have recommennded this house to several people after returning from our trip. The house had really nice & big washer & dryer. Was nice to come home with a suitcase of clean clothes rather than a hamper of dirty clothes. I took my teenager son & his friend & they enjoyed the bikes & kayaks. They also made friends with a couple other teenagers at the pool the first night we were there. Pool is...
Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill
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, (90)
"Explain to people that there is an opportunity to park the truck with a trailer and that there are ramps for the boat because I myself did not take my boat thinking that there was nothing like that. Thanks "
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.

Cudjoe Key Holiday Homes information

Number of reviews
1,379
Accommodation
495 Holiday Homes
Lowest Price
€344
Highest Price
€344

Recent Reviews in Cudjoe Key
Expedia verified reviews

Hyatt Vacation Club at Windward Pointe, Key West

Hyatt Vacation Club at Windward Pointe, Key West

5/5 Excellent
"I liked everything there; the room was clean, all appliances were working good, the ocean view is perfect!"
A verified traveller stayed at Hyatt Vacation Club at Windward Pointe, Key West
Posted 2 days ago
Hyatt Vacation Club at Windward Pointe, Key West