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
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Sep 12 - Sep 14
In two months
Oct 24 - Oct 26
In three months
Nov 21 - Nov 23
In four months
Dec 19 - Dec 21

Vacation Rentals in Cudjoe Key

Newly Remodeled! Gated Community on Open Water, Dock, Heated Pool, Kayaks, Bikes
On the beach, beach towels

Newly Remodeled! Gated Community on Open Water, Dock, Heated Pool, Kayaks, Bikes

9.8 out of 10, Exceptional, (237)
"Clean and inviting property, great location, attentive host. Highly recommend."
The price is ￥51,429
￥120,143 total
includes taxes & fees
Aug 26 - Aug 27
Newly Remodeled! Gated Community on Open Water, Dock, Heated Pool, Kayaks, Bikes
Cottage with Pool and Boat Dockage just minutes to Key West!
Exterior

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

8.6 out of 10, Excellent, (144)
"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. "
The price is ￥18,368
￥37,323 total
includes taxes & fees
Aug 27 - Aug 28
Cottage with Pool and Boat Dockage just minutes to Key West!
Waterfront Home
Terrace/patio

Waterfront Home

8.8 out of 10, Excellent, (168)
"Great price great location "
Waterfront Home
Cottage with swimming pool and dockage, just minutes to Key West!
Miscellaneous

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

9.0 out of 10, Wonderful, (153)
"The cottage was comfortable, and the bed was just right. We were in the Keys for a funeral, so not much running around."
Cottage with swimming pool and dockage, just minutes to Key West!
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!
Old Wooden Bridge Resort and Marina
2 Bedroom Aqua Lodge # 13 Barracuda | Living area | Flat-screen TV

Old Wooden Bridge Resort and Marina

2.5 star property
8.6 out of 10, Excellent, (257)
"River boat houses, pool, kayak rentals. "
Old Wooden Bridge Resort and Marina
Aqua Lodges at Hurricane Hole Marina
Restaurant

Aqua Lodges at Hurricane Hole Marina

2.0 star property
8.8 out of 10, Excellent, (161)
"The stay was beautiful "
The price is ￥8,761
￥34,487 total
includes taxes & fees
Aug 27 - Aug 28
Aqua Lodges at Hurricane Hole Marina
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, (78)
"Took the team down to the keys for a little R&R"
Old Florida Style, wrap around porch, boat basin for dockage, open water
Sunshine Key RV Resort & Marina
Kayaking

Sunshine Key RV Resort & Marina

2.0 star property
8.8 out of 10, Excellent, (156)
"I loved staying at Sunshine key"
Sunshine Key RV Resort & Marina
Luxury High End, 2 Bikes, Highspeed Wi-Fi, Work station, Pool, Hot Tub, Gym
Outdoor pool, a heated pool

Luxury High End, 2 Bikes, Highspeed Wi-Fi, Work station, Pool, Hot Tub, Gym

9.8 out of 10, Exceptional, (296)
"Excellent accommodations, gorgeous condon"
Luxury High End, 2 Bikes, Highspeed Wi-Fi, Work station, Pool, Hot Tub, Gym
Two-bedroom, two-bath condo close to the Ocean. Full kitchen, living r & balcony
Sport court

Two-bedroom, two-bath condo close to the Ocean. Full kitchen, living r & balcony

9.0 out of 10, Wonderful, (26)
"Great place, great location, great communication from host!"
The price is ￥33,796
￥56,885 total
includes taxes & fees
Aug 26 - Aug 27
Two-bedroom, two-bath condo close to the Ocean. Full kitchen, living r & balcony
GOOD VISIBILITY ~ 4 Bedroom, 3 Bathroom Condo w/ Pool and Ocean Views!
A heated pool

GOOD VISIBILITY ~ 4 Bedroom, 3 Bathroom Condo w/ Pool and Ocean Views!

9.8 out of 10, Exceptional, (44)
"Wonderful view, lot's of space, great location "
GOOD VISIBILITY ~ 4 Bedroom, 3 Bathroom Condo w/ Pool and Ocean Views!
The Salt Cay | Updated! Stunning Sunset View, Pool!
A heated pool

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

9.8 out of 10, Exceptional, (24)
"Place was so clean and perfect location! Very quiet and relaxing"
The price is ￥14,106
￥50,011 total
includes taxes & fees
Aug 26 - Aug 27
The Salt Cay | Updated! Stunning Sunset View, 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, (55)
"Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: great place, great location! we'll be back year after year!"
ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub!
Docked in Paradise
Terrace/patio

Docked in Paradise

The price is ￥42,980
￥62,497 total
includes taxes & fees
Sep 1 - Sep 2
Docked in Paradise
Oceanview home with private pool & lush landscaping!
A heated pool

Oceanview home with private pool & lush landscaping!

9.8 out of 10, Exceptional, (114)
"Great place to stay very kid friendly and a short golfcart ride to everything "
Oceanview home with private pool & lush landscaping!
Living the Dream Key West Style
Marina

Living the Dream Key West Style

10.0 out of 10, Exceptional, (21)
"Great hosts and great accommodations!"
The price is ￥39,542
￥50,217 total
includes taxes & fees
Aug 26 - Aug 27
Living the Dream Key West Style
Oversized home for the whole family w/private pool & dock
A heated pool

Oversized home for the whole family w/private pool & dock

9.8 out of 10, Exceptional, (134)
"It met all our needs. Loved the location!! Particularly loved the great room off the kitchen…great family times were had by all!"
Oversized home for the whole family w/private pool & dock
Coconut Mallory Resort And Marina By Kees Vacations
Meeting facility

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
Direct Ocean View from Your Condo-No Contact Check-In
Outdoor dining

Direct Ocean View from Your Condo-No Contact Check-In

9.4 out of 10, Exceptional, (159)
"We loved this lovely condo. Close to beach, pool and activities. Clean and had everything you need. "
Direct Ocean View from Your Condo-No Contact Check-In
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

Hampton Inn Key West FL

Hampton Inn Key West FL

10/10 Excellent
"We just got home from a week stay at the Hampton Inn resort. Our room was comfortable and received daily cleaning service. The frig and microwave was nice to have. Love the first two middle buildings that surround the pool. The pool was a good size and clean. The Cheekie Hut provided great service and good food, available to order until 7 or a little after in the evening. The breakfast provided was always good with a large variety. The team was pleasant to work with and assisted us with anything we needed. The shuttle to and from airport was super convenient and was a great option to get downtown, running every 45 minutes. We would definitely recommend this property. Keep in mind, you do need the shuttle or another form of transportation to get to the old town area and duval street."
Sherrie 7-night trip
Posted 2 days ago
Hampton Inn Key West FL