Search Vacation Homes in Cudjoe Key

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Compare 563 Vacation Homes in Cudjoe Key with updated reviews, rates, and availability.

INCOMMUNICADO ~ Waterfront 2 BR/2 Ba w/ Dockage and Hot Tub!
9.4 out of 10, Exceptional, 15 reviews
"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!
ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub!
8.8 out of 10, Excellent, 18 reviews
"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!
Just 20 miles from Key West! Oceanfront, dockage, swimming pool
8.4 out of 10, Very Good, 90 reviews
"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
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OFF CALL ~ Rustic, Nautical Decor With King Primary Suite & Heated Pool!
9.6 out of 10, Exceptional, 64 reviews
"Enjoyed our stay…..Dan was very helpful with the smart tv issue…."
OFF CALL ~ Rustic, Nautical Decor With King Primary Suite & Heated Pool!
Old Florida Style, wrap around porch, boat basin for dockage, open water
9.8 out of 10, Exceptional, 47 reviews
"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
Poolside Cottage #411
10.0 out of 10, Exceptional, 17 reviews
"Clean. Everything we needed in a key west stay."
The price is $216
$362 total
includes taxes & fees
Jun 4 - Jun 5
Poolside Cottage #411
NEWLY REMODELED KITCHEN!! PET FRIENDLY! 3 Bedroom 3 bathroom home. Sleeps 8
9.6 out of 10, Exceptional, 186 reviews
"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
Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill
9.8 out of 10, Exceptional, 186 reviews
"All amenities were operational and organized. check in/check out process was easy. i thoroughly enjoyed my stay with friends. thanks"
Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill
Casa Cay West Beautiful Tropical House 3 bedrooms 2 KING suites POOL 2 mi beach
10.0 out of 10, Exceptional, 388 reviews
"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
OCEAN FRONT PARADISE/290 ft PRIVATE DOCK/AWESOME VIEWS
9.2 out of 10, Wonderful, 91 reviews
"Location and outdoor living space was awesome!"
OCEAN FRONT PARADISE/290 ft PRIVATE DOCK/AWESOME VIEWS
Paris Mango: Waterfront Luxury Home with Ocean View & Heated Private Pool!
9.6 out of 10, Exceptional, 73 reviews
"Would book again if visiting Key West"
Paris Mango: Waterfront Luxury Home with Ocean View & Heated Private Pool!
**PLANTATION TROPICALE @ CASA EAST** Grand Estate & Pool + LAST KEY SERVICES…
10.0 out of 10, Exceptional, 34 reviews
"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…
CORAL CABANA ~ Lush Porch Views of the Pool & Gardens, near Golf Course!
9.8 out of 10, Exceptional, 97 reviews
"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!
CASA DE VINO ~ Amazing Price for Charming Townhouse with Pool & Tiki!
9.8 out of 10, Exceptional, 70 reviews
"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!
LICENSE TO CHILL ~ Waterfront 2 BR/2Ba in Cudjoe Key w/ Dockage & Parking!
9.6 out of 10, Exceptional, 13 reviews
"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!
Cozy, Perfect Conch Cottage!
9.0 out of 10, Wonderful, 30 reviews
"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!
Oceanside Paradise: Kayaks, Free WiFi, A/C, Grill, Elevated Deck, 24hr Security
9.8 out of 10, Exceptional, 217 reviews
"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
HAVANA DAYDREAMING ~ Waterfront 1 BR/1 Ba w/ Dockage & Hot Tub!
9.6 out of 10, Exceptional, 13 reviews
"What a great place. Easy to get to. Close to everything and right on the water. We will def stay here again. Highly recommended."
HAVANA DAYDREAMING ~ Waterfront 1 BR/1 Ba w/ Dockage & Hot Tub!
WATERFRONT PARADISE AT VENTURE OUT+4 BIKES & 2-2 SEAT KAYAKS! KING & QUEEN BEDS
9.6 out of 10, Exceptional, 73 reviews
"We always enjoy staying at venture out. They have everything you need right on the premises. Janet’s house was perfect for myself and three kids. Right on the canal so the kids could fish and even had a manatee come right up to us. We will definitely be back."
The price is $179
$475 total
includes taxes & fees
Jun 4 - Jun 5
WATERFRONT PARADISE AT VENTURE OUT+4 BIKES & 2-2 SEAT KAYAKS! KING & QUEEN BEDS
Casa Calypso- Beautiful Tropical Style House 3 KING Beds POOL 2 mi to beach
10.0 out of 10, Exceptional, 188 reviews
"The property exceeded our expectations. Very comfortable and great location. Just minutes from downtown Key West and next to a CVS. Great pizzeria as well just outside the community. Loved the secure entrance and safety of the location. Highly recommend!"
Casa Calypso- Beautiful Tropical Style House 3 KING Beds POOL 2 mi to beach
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
9.8 out of 10, Exceptional, 204 reviews
"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 $350
$442 total
includes taxes & fees
Jun 18 - Jun 19
Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes
Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill
9.8 out of 10, Exceptional, 186 reviews
"All amenities were operational and organized. check in/check out process was easy. i thoroughly enjoyed my stay with friends. thanks"
Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill
Just 20 miles from Key West! Oceanfront, dockage, swimming pool
8.4 out of 10, Very Good, 90 reviews
"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 Vacation Homes information

Number of reviews
1,645
Accommodation
563 Vacation Homes
Lowest Price
$179
Highest Price
$216

Recent reviews of Cudjoe Key hotels
Expedia verified reviews