Cudjoe Key Vacation Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

This weekend
Next weekend

Vacation Rentals in Cudjoe Key

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!

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

8.6 out of 10, Excellent, (143)
"We had a nice stay at the cottages. Location worked well for our fishing excursions and access across the street to old RT 1 to walk the dogs. "
Cottage with Pool and Boat Dockage just minutes to Key West!

Private Secluded Ocean View & Pool Near Key West

8.2 out of 10, Very good, (92)
"We stayed for my husband’s surprise 40th birthday weekend. Kazi was an amazing host and made the booking/arrival/departure process so easy. His hospitality was amazing and we can’t wait to come back."
Private Secluded Ocean View & Pool Near Key West

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 CA $309
CA $741 total
includes taxes & fees
Aug 2 - Aug 3
Just 20 miles from Key West! Oceanfront, dockage, swimming pool

Endless Summer Hideaway - lot 181

The price is CA $233
CA $413 total
includes taxes & fees
Aug 14 - Aug 15
Endless Summer Hideaway - lot 181

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

8.8 out of 10, Excellent, (72)
"Very nice quiet place for your lower key vacation. Nice accommodations and easy drive to Key West and Islamorada and several state parks. "
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

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

9.8 out of 10, Exceptional, (235)
"We (family of 5) really enjoyed our stay. All the equipment was as listed and in great condition. The location was perfect if you're looking for a less hectic Florida Keys experience."
The price is CA $493
CA $1,129 total
includes taxes & fees
Aug 13 - Aug 14
Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes, Boat Dock

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 CA $818
CA $1,401 total
includes taxes & fees
Aug 2 - Aug 3
Atlantic View Luxury Villa with Pool

Old Wooden Bridge Resort and Marina

2.5 star property
8.6 out of 10, Excellent, (252)
"I love ❤️ this place "
The price is CA $155
CA $368 total
includes taxes & fees
Aug 12 - Aug 13
Old Wooden Bridge Resort and Marina

Aqua Lodges at Hurricane Hole Marina

2.0 star property
8.8 out of 10, Excellent, (160)
"It was a great place to stay! There were a few bugs in the aqua Lodge in the kitchen area, but other than that awesome place!"
The price is CA $107
CA $351 total
includes taxes & fees
Aug 10 - Aug 11
Aqua Lodges at Hurricane Hole Marina

Coconut Mallory Resort And Marina By Kees Vacations

3.0 star property
8.2 out of 10, Very good, (818)
"Great place really nice rooms"
Coconut Mallory Resort And Marina By Kees Vacations

Living the Dream Key West Style

10.0 out of 10, Exceptional, (19)
"Great hosts and great accommodations!"
The price is CA $370
CA $461 total
includes taxes & fees
Aug 2 - Aug 3
Living the Dream Key West Style

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

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

7.4 out of 10, Good, (10)
"We were here celebrating 55th birthdays and had a blast. Great location and communication with Capt. We will return for sure, hoping to make it an annual get together."
The price is CA $488
CA $1,098 total
includes taxes & fees
Aug 11 - Aug 12
Charming 4-bedroom Yacht with AC, Pool, fitness room in fantastic Key West

ATLANTIC BREEZE ~ 2B/2BA Renovated Retreat w/ Pool, Fitness Area & Beach!

9.8 out of 10, Exceptional, (209)
"perfect for families with young kids"
ATLANTIC BREEZE ~ 2B/2BA Renovated Retreat w/ Pool, Fitness Area & Beach!

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

10.0 out of 10, Exceptional, (7)
"The ideal getaway, I brought a grill and a pan and did all the cooking outside on the deck. Took paddle boards through mangrove tunnels and saw tons of fish. Had a baby sea turtle swim up to the boat. "
The price is CA $223
CA $367 total
includes taxes & fees
Jul 31 - Aug 1
Florida Keys Living: Your Charming Houseboat Getaway in the Florida Keys!

Direct Oceanfront Cottage-Sunrise View- #2,

8.6 out of 10, Excellent, (186)
"Quiet area, ocean view, roomy place for family of 3. Will stay again, thank you! "
Direct Oceanfront Cottage-Sunrise View- #2,

The Salt Cay | Updated! Stunning Sunset View, Pool!

10.0 out of 10, Exceptional, (19)
"Place was so clean and perfect location! Very quiet and relaxing"
The price is CA $141
CA $481 total
includes taxes & fees
Aug 5 - Aug 6
The Salt Cay | Updated! Stunning Sunset View, Pool!

Cat Island Suite | Beautifully Renovated w/ Pool!

10.0 out of 10, Exceptional, (21)
"Great location. Enjoyed our stay!!"
The price is CA $141
CA $477 total
includes taxes & fees
Aug 13 - Aug 14
Cat Island Suite | Beautifully Renovated w/ Pool!

Sunshine Key RV Resort & Marina

2.0 star property
8.8 out of 10, Excellent, (154)
"I loved staying at Sunshine key"
Sunshine Key RV Resort & Marina
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

Top Cudjoe Key Hotel Reviews

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.