Cudjoe Key Vacation Rentals

  • 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
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
In two weeks

Vacation Rentals in Cudjoe Key

Charming cottages, dockage, pool, just minutes to Key West

8.6 out of 10, Excellent, (106)
"Drove From CLE to The Keys with my dog and enjoyed the quietness of the property. 30 an hour from Key West. Great rate. Would recommend. "
The price is ¥33,586
¥61,594 total
includes taxes & fees
Feb 26 - Feb 27
Charming cottages, dockage, pool, just minutes to Key West

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

9.0 out of 10, Wonderful, (194)
"We loved the house! Thank you for being so flexible with us. We thought the second bedroom had 2 beds when we booked online but it only has 1."
Ocean Perch, Dock, Open Water Views, 80' Heated Pool, Tennis, 20 Min to Key West

Cottage with swimming pool and dockage, just minutes to Key West!

9.0 out of 10, Wonderful, (139)
"It was a very cute and small place to stay. My husband and I are very tall and felt a little cramped in the bathroom otherwise our stay was great. Check in and out was simple. "
The price is ¥29,854
¥50,809 total
includes taxes & fees
Mar 25 - Mar 26
Cottage with swimming pool and dockage, just minutes to Key West!

Cottage with Pool and Dockage, just minutes to Key West

9.2 out of 10, Wonderful, (133)
"We enjoyed our stay, would stay again. Communication was excellent. Property is just as pictured. Great location, great value for the price. Could use a little freshening up, light bulb in laundry room, etc."
The price is ¥41,049
¥71,034 total
includes taxes & fees
Mar 2 - Mar 3
Cottage with Pool and Dockage, just minutes to Key West

Cudjoe Cottages, swimming pool, just 20 miles from Key West

8.8 out of 10, Excellent, (131)
"Three employees traveling in the Keys stayed and all reported their complete satisfaction with the accommodations and location. Thank you!"
The price is ¥41,049
¥89,917 total
includes taxes & fees
Feb 25 - Feb 26
Cudjoe Cottages, swimming pool, just 20 miles from Key West

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

8.4 out of 10, Very Good, (100)
"Property was exaxtly as described. Could use some updating, but everything was clean and functioning. The house was plenty spacious, but we did spend most of out time on the deck. Wouod stay again! "
The price is ¥41,796
¥90,309 total
includes taxes & fees
Feb 28 - Mar 1
Just 20 miles from Key West! Oceanfront, dockage, swimming pool

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

9.2 out of 10, Wonderful, (67)
"My family and I enjoyed our stay. It was very convenient to everything we wanted to do. Would definitely stay again."
The price is ¥37,318
¥69,057 total
includes taxes & fees
Mar 5 - Mar 6
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Cottage with Pool and Boat Dockage just minutes to Key West!

8.6 out of 10, Excellent, (132)
"Perfect location for us 23 miles to key west. Restaurants near by, pool, fishing pier. Can't wait to come back and do it all over again!"
Cottage with Pool and Boat Dockage just minutes to Key West!

Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes

9.8 out of 10, Exceptional, (223)
"Great week in the Florida Keys. Home was extremely clean, very well equipped, had everything you needed to make you feel at home. Each bedroom had it's own ensuite bath and it was perfect for two couples. Location was excellent and would not hesitate to book here again.Thanks Melanie!"
The price is ¥59,708
¥130,350 total
includes taxes & fees
Mar 22 - Mar 23
Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes

Private Secluded Ocean View & Pool Near Key West

8.4 out of 10, Very Good, (85)
"This house is beautiful, it’s an old Keys style home, nautical, clean, beautiful views, we spent most of our time in the pool. Great place to just get away and relax. Love that is was off the beaten path. The palm trees, coconuts and yard is beautiful. The owner answered us almost immediately for any needs or questions we had. Will definitely make this a yearly trip. "
Private Secluded Ocean View & Pool Near Key West

FL Keys Cottage with Ocean Views - Venture Out Unit 395

8.8 out of 10, Excellent, (3)
"Very clean, comfortable beds. Close to everything we wanted to do!"
FL Keys Cottage with Ocean Views - Venture Out Unit 395

Atlantic View Luxury Villa with Pool

3.5 star property
10.0 out of 10, Exceptional, (1)
"We were here for a night and it was great. A nice rustic feel on a big property, with good view. "
The price is ¥75,568
¥137,258 total
includes taxes & fees
Mar 26 - Mar 27
Atlantic View Luxury Villa with Pool

Aqua Lodges at Hurricane Hole Marina

2.0 star property
8.8 out of 10, Excellent, (117)
"Awesome place, with a cool location right near the mangroves. Has a little restaurant and bar and gift shop, as well as kayak tours and rentals. Paddle boards too. We liked the visits from the manatees and nurse sharks near the fish cleaning station. Only negatives I have are that the ceiling fan chains were broken and harder to reach, some of the pillows were a bit yellowish and have seen better days and multiple devices like the Air conditioner and TV remotes batteries were dead, but they...
The price is ¥39,767
¥69,759 total
includes taxes & fees
Mar 3 - Mar 4
Aqua Lodges at Hurricane Hole Marina

Old Wooden Bridge Resort and Marina

2.5 star property
8.4 out of 10, Very Good, (191)
"Everything about it was great"
The price is ¥22,241
¥39,949 total
includes taxes & fees
Feb 24 - Feb 25
Old Wooden Bridge Resort and Marina

Coconut Mallory Resort And Marina By Kees Vacations

3.0 star property
8.2 out of 10, Very Good, (803)
"Great location, clean, and good customer service. wish they had fishing rods and more to do around the property, and the AC didn't keep the upstairs cool, very hot up there at night. overall, happy about the stay."
Coconut Mallory Resort And Marina By Kees Vacations

Charming 4-bedroom Yacht with AC, Pool, fitness room in fantastic Key West

10.0 out of 10, Exceptional, (4)
"Was just a teaser initial trip to Key West but staying on the water was awesome! Beautiful views and great amenities. Kevin and Captain Philip were great throughout the whole process including great local recommendations! One thing to note, if you are 6’ plus, will need to watch your head and the steps downstairs require concentration. As a shorter person (barely 5’!) it all worked perfectly for me! Look forward to staying again and taking the boat out next time! "
Charming 4-bedroom Yacht with AC, Pool, fitness room in fantastic Key West

Florida Keys Living: Your Charming Houseboat Getaway in the Florida Keys!

10.0 out of 10, Exceptional, (3)
"I didn’t really know what I was getting into, but I’m glad I didn’t cancel. This was such a beautiful experience to have shared with just myself. The bed was comfortable and I slept really well both nights. The second night, I had to rent a kayak from the marina (40) to get to the house. It was a beautiful sunset paddle. It’s easy enough, but even as an experienced paddler, it’s about 20 minutes . I had to leave around 5am to catch my flight and paddled back to the marina in pitch black. It was...
The price is ¥28,361
¥45,378 total
includes taxes & fees
Feb 27 - Feb 28
Florida Keys Living: Your Charming Houseboat Getaway in the Florida Keys!

Poolside Cottage #411

9.8 out of 10, Exceptional, (38)
"Quiet area close to everything we were looking for. "
The price is ¥50,453
¥77,863 total
includes taxes & fees
Mar 3 - Mar 4
Poolside Cottage #411

TRAVEL THE KEYS OR JUST RELAX AT THE DOCK

9.4 out of 10, Exceptional, (27)
"We had a bunch of guys stay here recently while we were in town for a fishing trip. We also had the penthouse at The Perry hotel but ended up spending more time on on the 3rd deck roof of the boat! It's an older boat but very cool with lots of character, plenty of room 8 guys in their 30s to sleep with everyone getting their own bed. It's hard to beat the location and price honestly! We rented golf carts from the hotel used those to explore the beaches and downtown area. The marina is only 10...
TRAVEL THE KEYS OR JUST RELAX AT THE DOCK

Penthouse Beach Ocean Views- Live the Dream

9.6 out of 10, Exceptional, (232)
"We had a great stay at this property. Mike was easy to work with. We has an issue with our key pad to enter the apartment. I called Mike and he solved immediately. Very personable and helpful. I hope we get a chance to come back. "
Penthouse Beach Ocean Views- Live the Dream
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.
Don't see what you're looking for?
See all available properties in Cudjoe Key
Save an average of 15% on thousands of hotels when you're signed in

Other types of properties in Cudjoe Key you may be interested in

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

9.0 out of 10, Wonderful, (194)
"We loved the house! Thank you for being so flexible with us. We thought the second bedroom had 2 beds when we booked online but it only has 1."
Ocean Perch, Dock, Open Water Views, 80' Heated Pool, Tennis, 20 Min to Key West

Cottage with swimming pool and dockage, just minutes to Key West!

9.0 out of 10, Wonderful, (139)
"It was a very cute and small place to stay. My husband and I are very tall and felt a little cramped in the bathroom otherwise our stay was great. Check in and out was simple. "
The price is ¥29,854
¥50,809 total
includes taxes & fees
Mar 25 - Mar 26
Cottage with swimming pool and dockage, just minutes to Key West!

FL Keys Cottage with Ocean Views - Venture Out Unit 395

8.8 out of 10, Excellent, (3)
"Very clean, comfortable beds. Close to everything we wanted to do!"
FL Keys Cottage with Ocean Views - Venture Out Unit 395
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.

Frequently asked questions

Can I find vacation rentals in Cudjoe Key?

Yes, we give you a choice of vacation rentals close to well known points of interest in Cudjoe Key, or you can choose a more remote option if you're looking for relaxation. Cudjoe Key is known for its seafood restaurants and seaside.

What's the top vacation rental that Cudjoe Key has to offer?

3 night minimum! Spectacular Ocean Views!: This Cudjoe Key vacation home rental offers a balcony, a barbecue grill, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Our travelers also rate Ocean Perch, Dock, Open Water Views, 80' Heated Pool, Tennis, 20 Min to Key West as a favorite home for rent in Cudjoe Key.

How many vacation rentals are there in Cudjoe Key?

With 205 Expedia vacation rentals, you're sure to find just the right place for your Cudjoe Key stay.

What can I see and do in Cudjoe Key?

While exploring the area, visit family-friendly sights like Key West Visitors Center, or get outside and enjoy nature at Florida Keys Beaches. Boca Chica Beach and Calusa Beach are a couple of places you'll find in the larger area.

What are vacation rentals like in Cudjoe Key?

Vacation rentals are private properties you can stay in for a few days or a quick weekend in Cudjoe Key. Vacation rentals offer amenities such as laundry facilities and kitchens so you'll be comfy for your stay. If you're concerned about cleanliness, vacation rentals can offer a sense of privacy away from shared hotel elevators and busy lobbies while still allowing you to travel. You'll also find more space in a vacation rental than in a traditional hotel, which makes a vacation rental an attractive choice for a small group gathering.