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

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Check prices for these dates

In two weeks
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

Our top choices for Cudjoe Key holiday rentals

A two-story beachfront house with a balcony, a covered outdoor seating area, and a small boat dock.

1. Atlantic View Luxury Villa with Pool

Atlantic View Luxury Villa with Pool
3.5 star property
Summerland Key
7.4 out of 10, Good, (3 reviews)
"We were here for a night and it was great. A nice rustic feel on a big property, with good view. "
United States
Preetam
The price is Rp9.256.522
Rp17.456.594 total
includes taxes & fees
11 Oct - 12 Oct
Atlantic View Luxury Villa with Pool
A wooden deck with a railing, wicker chairs, and a view of greenery.

2. Starlight Serenity - Hideaway w Stunning Views

Starlight Serenity - Hideaway w Stunning Views
2.0 star property
Summerland Key
10.0 out of 10, Exceptional, (1 review)
"The host team is amazing and very responsive. The house is very beautiful inside and out. We loved grilling downstairs, so much room down there. We loved our stay here because it was very secluded, unlike Key West, where you are on top of each other. The location is perfect because you can still make it down to Key West in 25 minutes for activities and food."
United States
max
The price is Rp5.214.812
Rp12.396.538 total
includes taxes & fees
14 Oct - 15 Oct
Starlight Serenity - Hideaway w Stunning Views
A cozy room with a brown leather sofa, a white table, and a ceiling fan.

3. Old Wooden Bridge Resort and Marina

Old Wooden Bridge Resort and Marina
2.5 star property
Punta Brisa
8.6 out of 10, Excellent, (373 reviews)
"Best stop over before going to Key west. We enjoyed here a lot, parking our trailer was never a problem."
United States
Daisybel
The price is Rp1.568.958
Rp4.280.438 total
includes taxes & fees
28 Oct - 29 Oct
Old Wooden Bridge Resort and Marina
A marina with boats docked, a small docked boat with a thatched roof, and a restaurant with outdoor seating overlooking the water.

4. Aqua Lodges at Hurricane Hole Marina

Aqua Lodges at Hurricane Hole Marina
2.0 star property
Stock Island
8.8 out of 10, Excellent, (199 reviews)
"Unique stay on a boathouse! Clean place, plenty of room!"
United States
Kagni
The price is Rp1.754.715
Rp5.031.583 total
includes taxes & fees
9 Oct - 10 Oct
Aqua Lodges at Hurricane Hole Marina
A beachside resort with a wooden deck, palm trees, and a sunset view.

5. Grand Marina Suite by Brightwild Waterfront

Grand Marina Suite by Brightwild Waterfront
2.0 star property
Stock Island
10.0 out of 10, Exceptional, (3 reviews)
"Nice place "
United States
Pawel
The price is Rp7.093.446
Rp12.329.583 total
includes taxes & fees
12 Oct - 13 Oct
Grand Marina Suite by Brightwild Waterfront
Exterior

6. Island View 1BR Residence With Balcony

Island View 1BR Residence With Balcony
2.0 star property
Key West
10.0 out of 10, Exceptional, (3 reviews)
"Great place it is a full apartment with everything you could need and very clean "
United States
Luis
The price is Rp3.950.540
Rp6.107.622 total
includes taxes & fees
11 Oct - 12 Oct
Island View 1BR Residence With Balcony
Room

7. Resort View 1BR Suite

Resort View 1BR Suite
2.0 star property
Key West
9.0 out of 10, Wonderful, (4 reviews)
"Open sewage behind pool bar rude front desk grumpy bartender Nice condo good restaurant "
United States
Michael
The price is Rp4.087.229
Rp6.260.283 total
includes taxes & fees
13 Oct - 14 Oct
Resort View 1BR Suite
A wooden boardwalk leading to a building with a green roof, surrounded by palm trees and a body of water.

8. The Grenada Suite Pool View Private Balcony

The Grenada Suite Pool View Private Balcony
2.0 star property
Key West
9.0 out of 10, Wonderful, (2 reviews)
"A little dated, but clean and well located."
United States
Luis
The price is Rp4.417.648
Rp10.316.062 total
includes taxes & fees
27 Oct - 28 Oct
The Grenada Suite Pool View Private Balcony
A white two-story house with a balcony and a swimming pool.

9. Capmar House by Brightwild Huge Home Pool

Capmar House by Brightwild Huge Home Pool
2.0 star property
Raccoon Key
10.0 out of 10, Exceptional, (1 review)
"Wonderful property, 4 large bedroom and en suite bathroom, private pool we really liked our stay"
France
Karen
The price is Rp13.992.420
Rp28.809.981 total
includes taxes & fees
11 Oct - 12 Oct
Capmar House by Brightwild Huge Home Pool
A spacious foyer with a wooden staircase, a console table with decorative items, and a view of the outdoors through a glass door.

10. Evershore House Pool Parking Dock

Evershore House Pool Parking Dock
2.0 star property
Raccoon Key
The price is Rp13.992.420
Rp28.809.981 total
includes taxes & fees
20 Oct - 21 Oct
Evershore House Pool Parking Dock
A two-story house with a swimming pool, surrounded by greenery and palm trees.

11. Seagate House by Brightwild Waterfront w Dock

Seagate House by Brightwild Waterfront w Dock
2.0 star property
Raccoon Key
The price is Rp13.992.420
Rp28.809.981 total
includes taxes & fees
20 Oct - 21 Oct
Seagate House by Brightwild Waterfront w Dock
A swimming pool with a green-roofed building nearby, surrounded by palm trees.

12. Tortuga Suite Sparkling Pool Hot Tub

Tortuga Suite Sparkling Pool Hot Tub
2.0 star property
Key West
The price is Rp3.970.014
Rp9.812.475 total
includes taxes & fees
11 Oct - 12 Oct
Tortuga Suite Sparkling Pool Hot Tub
A spacious living area with a blue sofa, a grey armchair, and a wooden coffee table. Large sliding glass doors lead to a pool and outdoor furniture.

13. Suncoast House by Brightwild Pool Boat Dock

Suncoast House by Brightwild Pool Boat Dock
2.0 star property
Raccoon Key
The price is Rp14.476.558
Rp32.551.448 total
includes taxes & fees
19 Oct - 20 Oct
Suncoast House by Brightwild Pool Boat Dock
A spacious kitchen with a marble island, pendant lighting, and a dining area with chairs and a table.

14. New Crestwood House by Brightwild Huge Pool

New Crestwood House by Brightwild Huge Pool
2.0 star property
Raccoon Key
The price is Rp19.308.700
Rp39.531.032 total
includes taxes & fees
12 Oct - 13 Oct
New Crestwood House by Brightwild Huge Pool
A living room with two sofas, a coffee table, and a view of the outdoors.

15. Waterlane House by Brightwild Pool Boat Dock

Waterlane House by Brightwild Pool Boat Dock
2.0 star property
Raccoon Key
The price is Rp13.992.420
Rp28.809.981 total
includes taxes & fees
20 Oct - 21 Oct
Waterlane House by Brightwild Pool Boat Dock
A spacious kitchen with a large island, white cabinetry, and pendant lighting.

16. Aquaria House by Brightwild Pool Boat Dock

Aquaria House by Brightwild Pool Boat Dock
2.0 star property
Raccoon Key
The price is Rp14.476.558
Rp29.345.874 total
includes taxes & fees
11 Oct - 12 Oct
Aquaria House by Brightwild Pool Boat Dock
A modern kitchen with a central island, bar stools, and a large window.

17. Brand New Catchlight House With Private Pool

Brand New Catchlight House With Private Pool
3.0 star property
Raccoon Key
The price is Rp19.747.535
Rp40.024.722 total
includes taxes & fees
11 Oct - 12 Oct
Brand New Catchlight House With Private Pool
A spacious kitchen with a large island, pendant lighting, and a dining area with a table and chairs.

18. New Windrose House by Brightwild Pool

New Windrose House by Brightwild Pool
2.0 star property
Raccoon Key
The price is Rp18.662.961
Rp38.816.523 total
includes taxes & fees
18 Oct - 19 Oct
New Windrose House by Brightwild Pool
A two-story house with a pool, surrounded by palm trees and a clear sky.

19. Mirador House by Brightwild Pool Dock

Mirador House by Brightwild Pool Dock
2.0 star property
Raccoon Key
The price is Rp13.992.420
Rp32.017.705 total
includes taxes & fees
12 Oct - 13 Oct
Mirador House by Brightwild Pool Dock
A spacious living area with a wooden dining table, comfortable seating, a flat-screen TV, and large windows offering a view of the outdoors.

20. Spindrift House by Brightwild Huge Pool Dock

Spindrift House by Brightwild Huge Pool Dock
2.0 star property
Raccoon Key
The price is Rp13.992.420
Rp28.809.981 total
includes taxes & fees
12 Oct - 13 Oct
Spindrift House by Brightwild Huge Pool Dock
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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Top Cudjoe Key Hotel Reviews

Hampton Inn Key West FL

Hampton Inn Key West FL

10/10 Excellent
"I took my kids on an end of summer trip to Key West. I travel a lot and have never stayed at a Hampton Inn, so we weren’t sure what to expect. Check in was easy and the front desk staff explained everything in detail. Our room was clean and spacious and the balcony was a nice add on. We also enjoyed the pool, which was clean and a the water was a good temperature. The bar was amazing and the food at rheir restaurant was good and a good value for the price. We loved the amenities such as their shuttle and the activities desk, where we learned about a lot of fun options and ended up choosing the day-long Extreme Adventure (excellent by the way). It made it easy to find activities and ideas of things to do; plus she had coupons for basically everything. The breakfast was also awesome. My kids loved that they constantly changed out the waffle batter. We had a blast and look forward to staying here again next year!!"
Erin 4-night trip
Posted less than an hour ago
Hampton Inn Key West FL

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