Compare Cudjoe Key Vacation Rentals

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Cudjoe Key Rentals

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

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

0.4 mi from city center
Guests staying at this cottage have access to laundry facilities, a garden, and barbecue grills.
Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West

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

0.44 mi from city center
The price is $634 per night
$634
includes taxes & fees
$571 per night
May 20 - May 21
Guests staying at this vacation home have access to laundry facilities, barbecue grills, and a garden.
Just 20 miles from Key West! Oceanfront, dockage, swimming pool

Just 20 miles from Key West! Oceanfront, dockage, swimming pool

1.27 mi from city center
The price is $539 per night
$539
includes taxes & fees
$486 per night
May 12 - May 13
At this vacation home, guests have access to features like laundry facilities. This smoke-free vacation home also has barbecue grills.
Cottage with Pool and Dockage, just minutes to Key West

Cottage with Pool and Dockage, just minutes to Key West

0.38 mi from city center
The price is $349 per night
$349
includes taxes & fees
$315 per night
May 5 - May 6
Guests staying at this cottage have access to laundry facilities, a garden, and barbecue grills.
Oasis - Ocean view with pool and hot tub

Oasis - Ocean view with pool and hot tub

0.43 mi from city center
Guests staying at this vacation home enjoy a hot tub, laundry facilities, and a garden. This smoke-free vacation home also has barbecue grills.
JUDY'S PLACE ~ 2 Bedroom, 1 Bathroom Home in Venture Out Community!

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

2.01 mi from city center
At this vacation home, guests have access to features like laundry facilities. Staff members can help with accommodation requests, and provide concierge services. This smoke-free vacation home also has barbecue grills.
Cottage with swimming pool and dockage, just minutes to Key West!

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

0.38 mi from city center
The price is $285 per night
$285
includes taxes & fees
$257 per night
May 30 - May 31
Guests staying at this cottage have access to laundry facilities, a garden, and barbecue grills.
Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes

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

0.43 mi from city center
The price is $717 per night
$717
includes taxes & fees
$646 per night
May 26 - May 27
Guests of this vacation home enjoy features like an outdoor pool, a gym, and laundry facilities. Other amenities at this beach vacation home include a garden and barbecue grills.
Ocean/Canal Views 21ft Dock - Venture Out #357

Ocean/Canal Views 21ft Dock - Venture Out #357

1.88 mi from city center
Guests staying at this vacation home enjoy a hot tub, laundry facilities, and barbecue grills.
Atlantic View Luxury Villa with Pool

Atlantic View Luxury Villa with Pool

3.5 out of 5
125 Colson Dr, Summerland Key, FL
0.56 mi from city center
The price is $983 per night
$983
includes taxes & fees
$874 per night
May 5 - May 6
Guests staying at Atlantic View Luxury Villa with Pool enjoy access to 7 outdoor pools, a children's pool, and free WiFi in public areas. If you drive, take advantage of free parking. Staff members can help with accommodation requests, and provide luggage storage. If you like to take your furry friend along on your adventures, this pet-friendly property offers an off-leash area. Additional amenities include a computer station, a terrace, and laundry facilities.
Old Wooden Bridge Resort and Marina

Old Wooden Bridge Resort and Marina

2.5 out of 5
1791 Bogie Drive, Big Pine Key, FL
Free Cancellation
Reserve now, pay when you stay
9.59 mi from city center
The price is $256 per night
$256
includes taxes & fees
$239 per night
May 5 - May 6
Guests staying at Old Wooden Bridge Resort and Marina enjoy access to a marina, an outdoor pool, and free WiFi in public areas. If you plan to drive, free parking is available. Staff members can answer questions about accommodations, and also provide front-desk service during limited hours. Additional amenities include express check-in, a terrace, and barbecue grills.
Aqua Lodges at Hurricane Hole Marina

Aqua Lodges at Hurricane Hole Marina

2 out of 5
5130 Overseas Hwy, Key West, FL
17.08 mi from city center
The price is $313 per night
$313
includes taxes & fees
$278 per night
May 5 - May 6
Guests staying at this houseboat enjoy features like a marina and free WiFi in public areas. You can put free parking to good use if you drive.
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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.

Cudjoe Key Large Group Rentals

How to Book Vacation Rentals in Cudjoe Key



🏠 What is the best price for Cudjoe Key vacation rentals?

Cudjoe Key vacation rentals range in price, starting at $256 per night.


🏠 What types of vacation rentals in Cudjoe Key can I rent?

Orbitz offers a wide range of Cudjoe Key rentals so you can plan the perfect vacation. Whether you're on a budget or looking for luxury, our rentals include spots for families, couples, activities, leisure, summer, winter, and more. Explore unique property types available such as cabins, cottages, private vacation homes, and Cudjoe Key condo rentals.


🏠 Is it free to cancel my Cudjoe Key vacation rental with Orbitz?

Most vacation rentals are free to cancel when you do so before the cancellation deadline. However, cancellation policies vary by property. Non-refundable bookings will not receive a refund. We recommend booking with free cancellation in case your plans change.


🏠 How do I find the best deals to rent a Cudjoe Key vacation rental with Orbitz?

There are many different options for finding the best deal to suit your needs. Choose exclusive offers on rentals in various locations in Cudjoe Key. You can filter by price range, guest rating, property type, neighborhood, and more to customize your search and view the best deals for you.


🏠 How can I cancel my vacation rental booking through Orbitz?

Change of plans? We get it. You can cancel most vacation rentals bookings by getting in touch with the property manager. Sign in to your account and navigate to ‘My Trips’. Choose ‘Itinerary’ to view the property’s contact details. For questions and concerns, you can always visit our customer service portal.


🏠 What are the advantages of booking a vacation rental in Cudjoe Key?

Vacation rentals are your home away from home, offering a different kind of experience than traditional hotels. They’re often the best option if you're looking for more space, more privacy, and a place to make your own. Find homes for all kinds of stays with Orbitz. Plan group vacations with short-term rentals or choose from our Cudjoe Key apartments and enjoy an extended stay.


🏠 Why should I book my vacation rental with Orbitz in Cudjoe Key?

Orbitz offers incredible deals and offers on a large selection of vacation rentals as your one-stop-shop for travel. You’ll get rewards back with every booking, and when you book your stay along with a rental car, flight, or activity, our Cudjoe Key package deals will get you even more savings.

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