Cudjoe Key Vacation Rentals

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Check prices for these dates

Next weekend
May 9 - May 11
In two weeks
May 16 - May 18
In one month
May 30 - Jun 1
In two months
Jun 27 - Jun 29

Browse Select Cudjoe Key Vacation Homes

ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub!
Terrace/patio

ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub!

8.8 out of 10, Excellent, (45)
"It was just the right place for my family. We really enjoyed the view and close proximity to Key West. "
ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub!
Captain's Daughter: Oversized home for the whole family w/private pool & dock
A heated pool

Captain's Daughter: Oversized home for the whole family w/private pool & dock

9.8 out of 10, Exceptional, (126)
"Very large, modern, and quiet home, perfect for a large family vacation! It made our 7 days on Key West the best!"
Captain's Daughter: Oversized home for the whole family w/private pool & dock
Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West
Fridge, microwave, oven, stovetop

Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West

8.8 out of 10, Excellent, (146)
"Good location "
The price is CA $415
CA $876 total
includes taxes & fees
May 1 - May 2
Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West
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!

9.8 out of 10, Exceptional, (82)
"We very much enjoyed our stay. Very nice condo and beautiful pool close to Key West and Botanical Gardens which we enjoyed!"
OFF CALL ~ Rustic, Nautical Decor With King Primary Suite & Heated Pool!
Cudjoe Cottages, swimming pool, just 20 miles from Key West
Outdoor dining

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

8.8 out of 10, Excellent, (139)
"Great location and house was clean. "
Cudjoe Cottages, swimming pool, just 20 miles from Key West
**DOCKSIDE DAYDREAMS @ COCONUT MALLORY** Marina Villa + LAST KEY SERVICES…
Beach

**DOCKSIDE DAYDREAMS @ COCONUT MALLORY** Marina Villa + LAST KEY SERVICES…

9.8 out of 10, Exceptional, (87)
"Great House, but tight for 5 adults, not sure how 6 adults would fit"
**DOCKSIDE DAYDREAMS @ COCONUT MALLORY** Marina Villa + LAST KEY SERVICES…
Keys 3 Bedroom Corner Home near Beach & Key West
Fridge, microwave, oven, stovetop

Keys 3 Bedroom Corner Home near Beach & Key West

9.8 out of 10, Exceptional, (6)
"Great location, right in the middle keys, easy access to everything. "
The price is CA $414
CA $996 total
includes taxes & fees
May 5 - May 6
Keys 3 Bedroom Corner Home near Beach & Key West
Private Secluded Ocean View & Pool Near Key West
Outdoor pool, a heated pool

Private Secluded Ocean View & Pool Near Key West

8.4 out of 10, Very good, (89)
"Property was as advertised "
Private Secluded Ocean View & Pool Near Key West
Poolside Cottage #412
Outdoor dining

Poolside Cottage #412

9.6 out of 10, Exceptional, (22)
"The property and our place was really nice. Would definitely stay again. "
The price is CA $310
CA $525 total
includes taxes & fees
May 5 - May 6
Poolside Cottage #412
JUDY'S PLACE ~ 2 Bedroom, 1 Bathroom Home in Venture Out Community!
Shower, hair dryer, towels

JUDY'S PLACE ~ 2 Bedroom, 1 Bathroom Home in Venture Out Community!

10.0 out of 10, Exceptional, (1)
"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!
Palmgale Estate | Gorgeous KW Home w/ Heated Pool
Pool

Palmgale Estate | Gorgeous KW Home w/ Heated Pool

2.0 star property
The price is CA $1,091
CA $2,698 total
includes taxes & fees
May 27 - May 28
Palmgale Estate | Gorgeous KW Home w/ Heated Pool
COCONUT TELEGRAPH ~ Waterfront 2 BR/2Ba in Cudjoe Key w/ Dockage & Parking!
Outdoor dining

COCONUT TELEGRAPH ~ Waterfront 2 BR/2Ba in Cudjoe Key w/ Dockage & Parking!

9.6 out of 10, Exceptional, (32)
"Excellent views, very quiet, pool was outstanding "
COCONUT TELEGRAPH ~ Waterfront 2 BR/2Ba in Cudjoe Key w/ Dockage & Parking!
Poolside Cottage #411
Outdoor dining

Poolside Cottage #411

10.0 out of 10, Exceptional, (42)
"Lovely home to stay in for a couple of nights on Key West"
The price is CA $310
CA $515 total
includes taxes & fees
May 4 - May 5
Poolside Cottage #411
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, (73)
"Clean well equipped great location"
Old Florida Style, wrap around porch, boat basin for dockage, open water
One of the very few beach houses with a daily, rental license in the Keys.
Outdoor pool

One of the very few beach houses with a daily, rental license in the Keys.

8.8 out of 10, Excellent, (59)
"Overall very happy with our experience. Very easy communication with the owner and overall just very happy with the entire experience. Will Definitely book again"
The price is CA $759
CA $1,837 total
includes taxes & fees
May 21 - May 22
One of the very few beach houses with a daily, rental license in the Keys.
INCOMMUNICADO ~ Waterfront 2 BR/2 Ba w/ Dockage and Hot Tub!
Property grounds

INCOMMUNICADO ~ Waterfront 2 BR/2 Ba w/ Dockage and Hot Tub!

9.2 out of 10, Wonderful, (40)
"Beautiful property, amazing outdoor space on the water, clean and comfortable Given the cleaning fees are 50% of the cost I was little annoyed at how much check out chores are required of the guests. "
INCOMMUNICADO ~ Waterfront 2 BR/2 Ba w/ Dockage and Hot Tub!
Mother Ocean: Waterfront 4 Bedroom 3 Bath luxury Oceanfront home with pool
Terrace/patio

Mother Ocean: Waterfront 4 Bedroom 3 Bath luxury Oceanfront home with pool

9.4 out of 10, Exceptional, (66)
"We had a great stay! We enjoyed our week in Key West. The area was easy to get a Uber or taxi and not far from anything we wanted to do. We were able to grill as well. The response time from the property management was easy and they were quick to respond. "
Mother Ocean: Waterfront 4 Bedroom 3 Bath luxury Oceanfront home with pool
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, (108)
"The whole experience was decent until the last night. We met with a lot of termites and two cockroaches"
Just 20 miles from Key West! Oceanfront, dockage, swimming pool
Key West - Stock Island
Miscellaneous

Key West - Stock Island

4.0 star property
9.6 out of 10, Exceptional, (24)
"Nice place. Everything was as described. "
Key West - Stock Island
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, (217)
"Good accomodations"
Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill
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.
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Other property types in Cudjoe Key

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, (135)
"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!
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, (145)
"We had a wonderful stay in a small cottage in Cudjoe Key. It was a fun little place stay. Location was great for visiting the other Keys. I would seriously look at staying in one of the bigger cottages if I brought my family down. Thank you very much!"
The price is CA $207
CA $394 total
includes taxes & fees
May 30 - May 31
Cottage with swimming pool and dockage, just minutes to Key West!
Cottage with Pool and Dockage, just minutes to Key West
Pool

Cottage with Pool and Dockage, just minutes to Key West

9.2 out of 10, Wonderful, (140)
"We had a wonderful time at your place. Thank you for having us, we loved the Keys!"
The price is CA $242
CA $482 total
includes taxes & fees
May 1 - May 2
Cottage with Pool and Dockage, just minutes to Key West
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.