Cudjoe Key Holiday Rentals

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Holiday Rentals in Cudjoe Key

Property grounds
Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes
9.8 out of 10, Exceptional, (204)
"Overall, a very nice property in a good location, with good amenities. Located near several good Restaurants, especially the Square Grouper. Communication with Host was very good."
The price is NZ$721
includes taxes & fees
18 Jun - 19 Jun
Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes
Balcony
Just 20 miles from Key West! Oceanfront, dockage, swimming pool
8.4 out of 10, Very good, (89)
"Good place. 3 bed rooms all with Queen size beds. It was perfect for us. We sat on the porch mostly when we were there and played games. Not a long ride to Key West. Overall- we were happy and would stay there again."
Just 20 miles from Key West! Oceanfront, dockage, swimming pool
Pool
Cozy, Perfect Conch Cottage!
9.0 out of 10, Wonderful, (30)
"Our stay was great! The description is accurate. We enjoyed our 6 Mid-March days at "Cozy Perfect Conch Cottage." Yes, it's technically camping, but it's very NICE camping...in a campground...but a very NICE campground. The bed we used (there were only 2 of us) was super comfortable. The WiFi worked great. It was awesome having a full kitchen and washer/dryer. The towels were plentiful, soft and luxurious. Linens were also very soft and comfortable. Everything needed for basic cooking was...
Cozy, Perfect Conch Cottage!
Save an average of 15% on thousands of hotels when you're signed in
A heated pool
Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill
9.8 out of 10, Exceptional, (185)
"Highly recommend"
Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill
Exterior
Oceanside Paradise: Kayaks, Free WiFi, A/C, Grill, Elevated Deck, 24hr Security
9.8 out of 10, Exceptional, (217)
"My daughter and I stayed in Cudjoe Key to be close to Key West. The location was good. The unit had everything we needed both inside and out. We grilled and cooked which was great. The beds were comfortable. Unfortunately, the weather did not cooperate and excursions were cancelled so we spent more time in Key West than we had planned. But the unit had lots of games and the TV had the tennis channel which was very nice. All in all, it was a good time."
Oceanside Paradise: Kayaks, Free WiFi, A/C, Grill, Elevated Deck, 24hr Security
Outdoor dining
Ocean Perch, Dock, Open Water Views, 80' Heated Pool, Tennis, 20 Min to Key West
9.2 out of 10, Wonderful, (175)
"The view was wonderful. Great place to see sunrise every morning. This was a girls trip. If you are just there for fishing, this place is perfect. The refrigerator and freezer smelled of fish. Even after 3 nights, the smell was strong. I recommend bringing some arm and hammer baking soda for both fridge and freezer. The place is pretty close to Key West, so location is great. The neighbors were cleaning their fish right off the dock, so there were many seagulls. With seagulls, comes poop. They...
Ocean Perch, Dock, Open Water Views, 80' Heated Pool, Tennis, 20 Min to Key West
Outdoor pool, a heated pool
Tropical Getaway in Paradise.
9.4 out of 10, Exceptional, (80)
"It met our needs. Was generally clean. The bathroom was very clean. The beds were clean. The floors and surfaces were ok. The washer and dryer were great. The hot water was good. Nothing to complain about the house. The resort was nice and quiet. Very peaceful. Security did a good job, the resort is well staffed and the bathhouses were very clean. The pool was awesome. Bring your own darts and tennis equipment, the resort doesn’t provide them or have them. I would say the extra $125 was kind...
Tropical Getaway in Paradise.
Sun-loungers, beach towels
Comfortable Waterfront Vacation Rental
9.4 out of 10, Exceptional, (138)
"Other than the mile hike to front door, jk ( wheel chair ramp) the place was great. Plenty of room for docking my boat, clean with all the amenities. I would stay here again. Outdoor space is great on balcony and canal side. Its nice to be able to flush the boat engine after a day out and spray salt off as well. Thank you for the use of your home."
Comfortable Waterfront Vacation Rental
A heated pool
3 night minimum! Spectacular Ocean Views!
8.2 out of 10, Very good, (15)
"Unit was slightly smaller than what we were expecting by the pictures. Very clean, except for the floor in main area. Walking around left the soles of your feet very dirty. Used mop that was provided and it cleaned up nicely. When roll-out bed was out, there was no room to maneuver in the room. Everything worked as expected. Neighborhood was quiet and nice. Manager was responsive and very helpful. A lot of amenities were provided and appreciated."
3 night minimum! Spectacular Ocean Views!
Fridge, microwave, oven, stovetop
FL Keys Cottage with Ocean Views - Venture Out Unit 395
8.0 out of 10, Very good, (2)
"Great location and nice park amenities. Kids really liked the Venture Out pool."
FL Keys Cottage with Ocean Views - Venture Out Unit 395
2 Bedroom Aqua Lodge # 13 Barracuda | Living area
Old Wooden Bridge Resort and Marina
2.5 star property
8.6 out of 10, Excellent, (126)
"Amazing stay in a boat!"
The price is NZ$409
includes taxes & fees
30 May - 31 May
Old Wooden Bridge Resort and Marina
Sundeck
Sunshine Key RV Resort & Marina
2.0 star property
8.8 out of 10, Excellent, (130)
"Nice place, very clean and quiet. The chair and sofa bed was peeling and the kitchen ledge is uneven so we almost fell."
Sunshine Key RV Resort & Marina
Outdoor dining
Poolside Cottage #411
10.0 out of 10, Exceptional, (16)
"My son and his new wife stayed here for their honeymoon and they absolutely loved it!"
The price is NZ$601
includes taxes & fees
4 Jun - 5 Jun
Poolside Cottage #411
Fridge, cookware/dishes/utensils, dining tables
34’ Catamaran Sailboat
9.4 out of 10, Exceptional, (25)
"Friendly, easy access and close to desired destination "
34’ Catamaran Sailboat
Property grounds
SIGNIFICANTLY DISCOUNTED!! 45' Sea Ray Yacht Located in 5 Star Resort!
10.0 out of 10, Exceptional, (10)
"The Yacht was beautiful. The marina was amazing. The marina and resort had excellent restaurants and bars. It was very cool to see all of the boats coming and going. It was an easy Uber ride to Key West and enjoy the fast pace life. Then it was wonderful to come back to the quiet of the marina. Would highly recommend a stay here."
SIGNIFICANTLY DISCOUNTED!! 45' Sea Ray Yacht Located in 5 Star Resort!
Restaurant
Aqua Lodges at Hurricane Hole Marina
2.0 star property
8.8 out of 10, Excellent, (86)
"It’s an experience, it’s not a luxury stay. It’s sort of like staying in a camper with a septic holding tank that can get pretty smelly next to a working marina, with fish charters and a fish cleaning station. One morning we had to use a spare paddle to shoe away a stinky dead fish head so it wouldn’t get trapped under our unit and smell up the place. Staying on the water was unique but in mid May it would have been nice for more shade on the little deck. I’d save it for the slightly cooler...
The price is NZ$599
includes taxes & fees
2 Jun - 3 Jun
Aqua Lodges at Hurricane Hole Marina
Pool
Luxury High End, 2 Bikes, Highspeed Wi-Fi, Work station, Pool, Hot Tub, Gym
9.8 out of 10, Exceptional, (258)
"We really enjoyed our stay at this property. The condo was clean and well supplied with essentials. The property is well maintained and safe. We were able to use the included bicycles to get to most locations we wanted to go in old town. Southernmost point was a leisurely 15 min bike ride away. The property owner communicated well with us and answered all of our questions. The only thing we were not prepared for was the traffic noise. The unit does face a busy street, so you can hear vehicles...
Luxury High End, 2 Bikes, Highspeed Wi-Fi, Work station, Pool, Hot Tub, Gym
Property grounds
40'yacht in Paradise Awaits You!
9.6 out of 10, Exceptional, (23)
"We had a really nice couple of days on this boat. We are older (over 60), and we weren't sure if it was going to be our thing. It was good though! The host was amazingly helpful. We loved the private beach and pool right around the corner. We have been to Key West a lot, so we didn't need to do all the tourist stuff. We mostly stayed on Stock Island. It was easy to get Ubers, so we didn't bother with a car or golf cart. If we were staying longer, we probably would have rented a golf cart. The...
40'yacht in Paradise Awaits You!
On the beach, sun-loungers, beach towels
GATED OCEANFRONT CONDO AT SMATHER'S BEACH
9.2 out of 10, Wonderful, (109)
"My husband and I visit Key West every year. We don’t go to frequent Duval Street we go for the warmth of the sun, artist fairs, sunsets, our favorite restaurants and our favorite shops. My husband does go fishing with the guys once or twice. But we come back and feel as though we’ve been in paradise. When your husband is a farmer it does really seem like paradise 😂"
GATED OCEANFRONT CONDO AT SMATHER'S BEACH
Property grounds
ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub!
8.8 out of 10, Excellent, (18)
"Good location as far walking distance to a Cuban food truck- Luna. Hogfish is a good restaurant, good seafood and good service, short walk. Property was clean. Beds comfortable. Mostly quiet. It’s about 3 miles from Key West."
ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub!
Don't see what you're looking for?
See all available properties in Cudjoe Key
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.

Other types of properties in Cudjoe Key you may be interested in

Property grounds
Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes
9.8 out of 10, Exceptional, (204)
"Overall, a very nice property in a good location, with good amenities. Located near several good Restaurants, especially the Square Grouper. Communication with Host was very good."
The price is NZ$721
includes taxes & fees
18 Jun - 19 Jun
Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes
6 outdoor pools, free pool cabanas, pool umbrellas
Oceans Edge Key West Resort, Hotel & Marina
4.0 star property
9.0 out of 10, Wonderful, (1508)
"Excellent resort "
The price is NZ$417
includes taxes & fees
10 Jun - 11 Jun
Oceans Edge Key West Resort, Hotel & Marina
Beach nearby, white sand
Margaritaville Beach House Key West
4.0 star property
8.6 out of 10, Excellent, (1767)
"Very convenient with all the amenities..... would recommend it to anyone "
The price is NZ$522
includes taxes & fees
4 Jun - 5 Jun
Margaritaville Beach House 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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Cudjoe Key holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Cudjoe Key. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Cudjoe Key. Seeing all the best attractions is bound to make you fall in love with Cudjoe Key. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Cudjoe Key short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find holiday rentals in Cudjoe Key?

Yes, there are holiday rentals close to the most popular sights in Cudjoe Key, or you can select a more secluded option if you're looking for a relaxing stay. Cudjoe Key is known for its seafood restaurants and seaside.

What are some of the best holiday rentals that Cudjoe Key has to offer?

3 night minimum! Spectacular Ocean Views!: This highly rated holiday home rental in Cudjoe Key offers a balcony, a BBQ and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Our travellers also rate Ocean Perch, Dock, Open Water Views, 80' Heated Pool, Tennis, 20 Min to Key West as a favourite home for rent in Cudjoe Key.

How many holiday rentals are there in Cudjoe Key?

With 205 Expedia holiday rentals, you're guaranteed to find just the right place for your Cudjoe Key stay.

What can I see and do in Cudjoe Key?

While exploring the area, visit family-friendly sights like Key West Visitors Center, or get outside and enjoy nature at Florida Keys Beaches. Boca Chica Beach and Calusa Beach are a couple of places you'll find in the wider area.

What are holiday rentals like in Cudjoe Key?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Cudjoe Key. Holiday rentals provide amenities such as patios, hot tubs and fire pits so you'll have everything you want. If you're concerned about a clean environment, a holiday rental can offer a sense of seclusion away from shared hotel lifts and busy lobbies while still allowing you the enjoyment of travel. You'll also have more space in a holiday rental than in a standard hotel, which makes a holiday rental a popular choice for family trips or small group gatherings.

Recent reviews of Cudjoe Key properties
Expedia verified reviews