A tropical island with clear blue waters, palm trees, and a thatched-roof hut.

Search Vacation Homes in Cudjoe Key

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
24 Jul - 26 Jul
In two months
4 Sep - 6 Sep
In three months
2 Oct - 4 Oct
In four months
30 Oct - 1 Nov

Our top choices for Cudjoe Key vacation homes

A heated pool

Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access

Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access
Cudjoe Key
10.0 out of 10, Exceptional, (1 review)
"Excellent location - clean, quiet, well-kept community. Boat launch was key for us. Pool and beach looked very nice, but we didn't use. The unit is as described and has a nice patio out back that we used every day."
United States
Cheryl V.
The price is AED 617
AED 2,075 total
includes taxes & fees
12 Jul - 13 Jul
Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access
Exterior

SAVE BIG $$$ JULY/AUG. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

SAVE BIG $$$ JULY/AUG. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.8 out of 10, Exceptional, (93 reviews)
"Great location, very clean, and a responsive host. We enjoyed our stay and highly recommended this spot!"
United States
David T.
The price is AED 841
AED 1,950 total
includes taxes & fees
13 Jul - 14 Jul
SAVE BIG $$$ JULY/AUG. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Beach

Florida Keys Canal-Front 2BR/2BA w/ 35' Seawall, Dock & Spacious Comfort

Florida Keys Canal-Front 2BR/2BA w/ 35' Seawall, Dock & Spacious Comfort
Cudjoe Key
9.4 out of 10, Exceptional, (3 reviews)
The price is AED 771
AED 2,267 total
includes taxes & fees
12 Jul - 13 Jul
Florida Keys Canal-Front 2BR/2BA w/ 35' Seawall, Dock & Spacious Comfort
A heated pool

Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West

Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West
Cudjoe Key
8.0 out of 10, Very Good, (3 reviews)
" Great 2 bedroom home in a lovely vacation community . We enjoyed the 2 recliners to relax after a full day of exploring as well as in the morning with our coffee. The screened in patio was a nice perk as well . At check in , a calendar of events was provided and the staff were friendly and helpful. FYI : We enjoyed a gorgeous sunrise right by the beach near the pool ."
United States
jim b.
The price is AED 675
AED 2,133 total
includes taxes & fees
13 Jul - 14 Jul
Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West
Exterior

SAVE BIG $$$ JULY/AUG. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

SAVE BIG $$$ JULY/AUG. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.4 out of 10, Exceptional, (109 reviews)
"Enjoyed our stay at Venture Out. Loved having the water view. We used the pool, bikes and kayaks. Owners were very responsive. House was clean. Would definitely stay again."
United States
Lindsey S.
The price is AED 731
AED 1,815 total
includes taxes & fees
13 Jul - 14 Jul
SAVE BIG $$$ JULY/AUG. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
A heated pool

Waterfront 2BR/2BA | 35' Seawall for 32' Boat | Beautiful Sunrises on Cudjoe Key

Waterfront 2BR/2BA | 35' Seawall for 32' Boat | Beautiful Sunrises on Cudjoe Key
Cudjoe Key
10.0 out of 10, Exceptional, (3 reviews)
"Pool area was nice but only visited it once as so much to see and do!"
United States
Karen
The price is AED 868
AED 2,405 total
includes taxes & fees
15 Jul - 16 Jul
Waterfront 2BR/2BA | 35' Seawall for 32' Boat | Beautiful Sunrises on Cudjoe Key
Outdoor pool, a heated pool

Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds!

Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds!
Cudjoe Key
7.8 out of 10, Good, (20 reviews)
The price is AED 909
AED 1,886 total
includes taxes & fees
12 Jul - 13 Jul
Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds!
Beach

Canal Front Retreat w/ Ocean Views, 35' Dock & Golf Cart Option

Canal Front Retreat w/ Ocean Views, 35' Dock & Golf Cart Option
Cudjoe Key
9.2 out of 10, Wonderful, (15 reviews)
"Our family had an amazing vacation! We love the house and hope to come back!! "
United States
Tammy G.
The price is AED 733
AED 2,205 total
includes taxes & fees
16 Jul - 17 Jul
Canal Front Retreat w/ Ocean Views, 35' Dock & Golf Cart Option
Beach

Little Piece of Paradise #233 Waterfront Cottage with Dock, Pool & Canal Views

Little Piece of Paradise #233 Waterfront Cottage with Dock, Pool & Canal Views
Cudjoe Key
8.0 out of 10, Very Good, (1 review)
"The unit was very old and tired. As such, several windows did not open, the cook top light was not working, the shower surround was cracked and the joint caulking was bad to name some examples. However, the place was spotless when we arrived and with (needed) working AC. The kitchen is WELL appointed with cooking items, some spices, and baking supplies. The washer/dryer was a treat as we travel light. The waterfront deck/patio area was great for morning coffee and evening cocktails. Venture out...
United States
Pauline Y.
The price is AED 675
AED 2,148 total
includes taxes & fees
12 Jul - 13 Jul
Little Piece of Paradise #233 Waterfront Cottage with Dock, Pool & Canal Views
Property grounds

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

Cudjoe Cottages, swimming pool, just 20 miles from Key West
Cudjoe Key
8.8 out of 10, Excellent, (161 reviews)
"This was our second stay here and just as we remembered. It was clean and we had everything we needed. Would recommend it for visiting Key West as its only a 30 minute drive in."
United States
John S.
The price is AED 992
AED 2,188 total
includes taxes & fees
15 Jul - 16 Jul
Cudjoe Cottages, swimming pool, just 20 miles from Key West
Exterior detail

Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key

Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key
Cudjoe Key
10.0 out of 10, Exceptional, (5 reviews)
"Very clean, charming home. Host was fast with responses."
United States
April W.
The price is AED 948
AED 2,482 total
includes taxes & fees
2 Aug - 3 Aug
Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key
A heated pool

Waterfront Getaway with 23' Seawall, Boat Access, Outdoor Dining & Cozy Interiors

Waterfront Getaway with 23' Seawall, Boat Access, Outdoor Dining & Cozy Interiors
Cudjoe Key
8.0 out of 10, Very Good, (1 review)
Waterfront Getaway with 23' Seawall, Boat Access, Outdoor Dining & Cozy Interiors
A heated pool

Blue Lobster Lodge #543 Open Coastal Retreat with Pool Near Key West

Blue Lobster Lodge #543 Open Coastal Retreat with Pool Near Key West
Cudjoe Key
8.8 out of 10, Excellent, (10 reviews)
"We loved our stayed and booked again for next year. Its in our price range, plenty of space and we were all so comfortable. Its our favorite house we have rented in the area and hope to be able to continue to enjoy it years to come. "
United States
Alisa M.
The price is AED 694
AED 2,184 total
includes taxes & fees
14 Jul - 15 Jul
Blue Lobster Lodge #543 Open Coastal Retreat with Pool Near Key West
A heated pool

Relax at Keys Time – 2BR Waterfront Rental and Boat Dock

Relax at Keys Time – 2BR Waterfront Rental and Boat Dock
Cudjoe Key
9.2 out of 10, Wonderful, (30 reviews)
"Close to Key West and lots of great boating"
United States
Simon S.
Relax at Keys Time – 2BR Waterfront Rental and Boat Dock
Exterior

Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West

Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West
Cudjoe Key
8.8 out of 10, Excellent, (101 reviews)
"short drive to downtown of course as long as traffic allows it...quiet stay beautiful views...bring mosquito repellent. "
United States
Lismary D.
The price is AED 1,157
AED 2,632 total
includes taxes & fees
22 Jul - 23 Jul
Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West
Beach nearby

Ocean Blue #265 | Open-Water Views, Pet-Friendly 2BR Retreat in Venture Out

Ocean Blue #265 | Open-Water Views, Pet-Friendly 2BR Retreat in Venture Out
Cudjoe Key
10.0 out of 10, Exceptional, (1 review)
"Great place , incredible view. Highly recommend."
United States
Alessandro M.
The price is AED 1,735
AED 3,425 total
includes taxes & fees
14 Jul - 15 Jul
Ocean Blue #265 | Open-Water Views, Pet-Friendly 2BR Retreat in Venture Out
A heated pool

Sailfish Haven #390 - Ocean Views, 35' seawall

Sailfish Haven #390 - Ocean Views, 35' seawall
Cudjoe Key
8.8 out of 10, Excellent, (6 reviews)
"It was a perfect home to stay in cudokey"
United States
Patricia H.
Sailfish Haven #390 - Ocean Views, 35' seawall
Terrace/patio

House of the Rising Sun - VO479

House of the Rising Sun - VO479
Cudjoe Key
8.8 out of 10, Excellent, (14 reviews)
"Located in a great community and location in the Keys. Wonderful trip, we will be back. Great communication from the host."
United States
Emily H.
The price is AED 1,286
AED 3,165 total
includes taxes & fees
24 Jul - 25 Jul
House of the Rising Sun - VO479
Beach

Sea La Vie #197 Oceanfront Home with 49' Dock, Heated Pool & Florida Keys Views

Sea La Vie #197 Oceanfront Home with 49' Dock, Heated Pool & Florida Keys Views
Cudjoe Key
9.4 out of 10, Exceptional, (13 reviews)
"Had a great time. Clean and comfortable home. "
United States
Chris H.
The price is AED 868
AED 2,405 total
includes taxes & fees
19 Jul - 20 Jul
Sea La Vie #197 Oceanfront Home with 49' Dock, Heated Pool & Florida Keys Views
Beach

Waterfront 2BR/2BA with 35' Dock – Island Breeze Keys Escape

Waterfront 2BR/2BA with 35' Dock – Island Breeze Keys Escape
Cudjoe Key
8.0 out of 10, Very Good, (2 reviews)
"It was a short trip but we enjoyed our stay! "
United States
Jennifer S.
Waterfront 2BR/2BA with 35' Dock – Island Breeze Keys Escape
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.
View all properties
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

The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West

10/10 Excellent
"Was upgraded to the best room on property without asking, after they learned we had missed a flight and were arriving late. Our third stay this year, the staff and property is beyond excellent."
Patrick Joseph 4-night trip
Posted 8 hours ago
The Perry Hotel & Marina Key West