Cudjoe Key Holiday Rentals

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Check prices for these dates

Tonight
22 Jan - 23 Jan
Tomorrow
23 Jan - 24 Jan
This weekend
24 Jan - 26 Jan
Next weekend
31 Jan - 2 Feb

Holiday Rentals in Cudjoe Key

Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes
On the beach, sun-loungers, beach towels

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

9.8 out of 10, Exceptional, (221)
"Everything was very nice. We enjoyed sitting down by the water any time. It was close to everything we were interested in seeing and doing. Great stay."
The price is HK$3,309
HK$7,057 total
includes taxes & fees
20 Feb - 21 Feb
Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes
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, (136)
"Property kept clean. Very quiet. Close to my family"
The price is HK$1,167
HK$2,218 total
includes taxes & fees
3 Feb - 4 Feb
Cottage with swimming pool and dockage, just minutes to Key West!
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, (131)
"Stayed here for a few nights during a multi stop trip to Florida. The location is perfect for accessing the best of the lower keys. We brought our kayaks and launched right from the property for a great paddle. Easy drive to Bahia Honda for some beach time and more paddling. Also a great jumping off location for spending a nice long day in Key West. Beautiful sunrise from this property as well. Would stay again. "
Cottage with Pool and Boat Dockage just minutes to Key West!
Ocean Perch, Dock, Open Water Views, 80' Heated Pool, Tennis, 20 Min to Key West
Outdoor dining

Ocean Perch, Dock, Open Water Views, 80' Heated Pool, Tennis, 20 Min to Key West

9.0 out of 10, Wonderful, (189)
"The view was amazing but the inside needs some work. Soft floors in one of the bedrooms and bathroom. There was one spot that we had to step over to avoid going right thru the floor. Outside furniture was in need of repair, chairs with broken slats. Most of the window blinds were either broken or didn't open at all. Compared to other properties in Venture Out (we had family staying in two other rentals two roads over) this was overpriced compared to the others we saw. "
Ocean Perch, Dock, Open Water Views, 80' Heated Pool, Tennis, 20 Min to Key West
3 night minimum! Spectacular Ocean Views!
A heated pool

3 night minimum! Spectacular Ocean Views!

8.4 out of 10, Very good, (18)
"Venture out is a great location for being on the water. This rental was reasonable, spacious and clean! We had an amazing stay with no issues!"
3 night minimum! Spectacular Ocean Views!
Oceanside Paradise: Kayaks, Free WiFi, A/C, Grill, Elevated Deck, 24hr Security
Exterior

Oceanside Paradise: Kayaks, Free WiFi, A/C, Grill, Elevated Deck, 24hr Security

9.8 out of 10, Exceptional, (234)
"Clean, easy access, friendly complex/neighborhood. "
Oceanside Paradise: Kayaks, Free WiFi, A/C, Grill, Elevated Deck, 24hr Security
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, (97)
"My family of 5 stayed at this place for 3 nights. It is very convenient to Key West and Big Pine Key for the activities we participated in. Easy check-in and great communication with owner. The only issue was the house we stayed in could use a little updating--one example was the peeling wallpaper and old-looking/poorly cut moulding in places. That said, we would definitely stay there again. It was a good place for the whole family."
The price is HK$2,723
HK$5,429 total
includes taxes & fees
6 Feb - 7 Feb
Just 20 miles from Key West! Oceanfront, dockage, swimming pool
Comfortable Waterfront Vacation Rental
Sun-loungers, beach towels

Comfortable Waterfront Vacation Rental

9.4 out of 10, Exceptional, (147)
"This place was perfect for a couple’s getaway! Close enough to Key West to drive over and far enough away from hustle and bustle. Great restaurants nearby. Bed was very comfortable! Our only complaint was that we often ran out of hot water when showering…not a dealbreaker though. "
Comfortable Waterfront Vacation Rental
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, (127)
"Perfect spot to chill with friends, enjoy the views, and the pool is beautiful."
The price is HK$1,245
HK$2,564 total
includes taxes & fees
27 Jan - 28 Jan
Cottage with Pool and Dockage, just minutes to Key West
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, (204)
"The property was assessed river and we had all of the amenities we needed. "
Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill
Tropical Getaway in Paradise.
Outdoor pool, a heated pool

Tropical Getaway in Paradise.

9.4 out of 10, Exceptional, (84)
"Venture Out resort is nice and this cozy trailer is good!"
Tropical Getaway in Paradise.
FL Keys Cottage with Ocean Views - Venture Out Unit 395
Fridge, microwave, oven, stovetop

FL Keys Cottage with Ocean Views - Venture Out Unit 395

8.8 out of 10, Excellent, (3)
"Very clean, comfortable beds. Close to everything we wanted to do!"
FL Keys Cottage with Ocean Views - Venture Out Unit 395
Old Wooden Bridge Resort and Marina
Living area

Old Wooden Bridge Resort and Marina

2.5 star property
8.4 out of 10, Very good, (179)
"Our stay in cabin 9 (turquoise one) was great. This cabin was perfect for our needs and we brought two dogs with us, no issues with that. We loved our stay but to be transparent this is really no frills. There is no sink sponge, no aluminum foil no nothing extra in the kitchen so bring your own!! The mattresses are VERY firm. There were a few small cosmetic issues that could be addressed in this cabin that would make a huge difference, example, crooked drawer front in kitchen, pinned drapes...
The price is HK$1,004
HK$1,907 total
includes taxes & fees
26 Jan - 27 Jan
Old Wooden Bridge Resort and Marina
Aqua Lodges at Hurricane Hole Marina
Restaurant

Aqua Lodges at Hurricane Hole Marina

2.0 star property
8.8 out of 10, Excellent, (112)
"We loved staying on the houseboat."
The price is HK$1,183
HK$2,425 total
includes taxes & fees
28 Jan - 29 Jan
Aqua Lodges at Hurricane Hole Marina
34’ Catamaran Sailboat
Interior

34’ Catamaran Sailboat

9.4 out of 10, Exceptional, (30)
"We had a wonderful time. It is an older, smaller boat but we enjoyed it. There is a port a pot in the cabin but there is a huge shower and bathroom under the carport. We were able to fish right off the boat. Frank will answer texts pretty quickly. "
34’ Catamaran Sailboat
Poolside Cottage #411
Outdoor dining

Poolside Cottage #411

10.0 out of 10, Exceptional, (36)
"Great little condo - perfect for our family to visit Key West! "
The price is HK$1,892
HK$3,143 total
includes taxes & fees
28 Jan - 29 Jan
Poolside Cottage #411
Direct Oceanfront Cottage-Sunrise View- #2,
On the beach

Direct Oceanfront Cottage-Sunrise View- #2,

8.6 out of 10, Excellent, (169)
"It was kind of exciting. the cops showed up on the property and on the next door property to the North, there was a tree of stolen bouys and a stolen crab trap. It was quiet. there was a bit of a flood when it rained but within a day or 2 the water was gone. we had trouble opening the slider on the deck and I think there was moisture in the door. Hopefully we left it pretty clean. we had to be at the airport by 6:30. thank you, it was a wonderful stay. Patty "
Direct Oceanfront Cottage-Sunrise View- #2,
SIGNIFICANTLY DISCOUNTED!! 45' Sea Ray Yacht Located in 5 Star Resort!
Property grounds

SIGNIFICANTLY DISCOUNTED!! 45' Sea Ray Yacht Located in 5 Star Resort!

9.8 out of 10, Exceptional, (16)
"Staying on the Grand Admiral was really awesome for my wife and I. The location at Perry Marina was exceptional. The whole process was very easy, working with Kathy for booking, Stephanie for check-in and Captain John for our charter, everything went smooth. "
SIGNIFICANTLY DISCOUNTED!! 45' Sea Ray Yacht Located in 5 Star Resort!
The Caroline Suite | 1 bed, 1 bath condo w/shared pool
Fridge, microwave, coffee/tea maker, cookware/dishes/utensils

The Caroline Suite | 1 bed, 1 bath condo w/shared pool

9.4 out of 10, Exceptional, (12)
"Place was clear, ready, and in a great area. If your looking for a good place in key west this is it"
The price is HK$3,073
HK$5,332 total
includes taxes & fees
23 Jan - 24 Jan
The Caroline Suite | 1 bed, 1 bath condo w/shared pool
The Crystalmarine Suite – Rustic Luxury on the Sea
Interior

The Crystalmarine Suite – Rustic Luxury on the Sea

10.0 out of 10, Exceptional, (2)
"This VRBO is a dream for those looking to escape the hustle and bustle of everyday life. With its unique location, it provides a perfect blend of adventure and relaxation. Whether you're looking to reconnect with nature or simply unwind in a beautiful setting, this floating house offers an unparalleled experience."
The price is HK$5,446
HK$6,905 total
includes taxes & fees
27 Jan - 28 Jan
The Crystalmarine Suite – Rustic Luxury on the Sea
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 types of properties in Cudjoe Key you may be interested in

Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes
On the beach, sun-loungers, beach towels

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

9.8 out of 10, Exceptional, (221)
"Everything was very nice. We enjoyed sitting down by the water any time. It was close to everything we were interested in seeing and doing. Great stay."
The price is HK$3,309
HK$7,057 total
includes taxes & fees
20 Feb - 21 Feb
Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes
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, (136)
"Property kept clean. Very quiet. Close to my family"
The price is HK$1,167
HK$2,218 total
includes taxes & fees
3 Feb - 4 Feb
Cottage with swimming pool and dockage, just minutes to Key West!
Ibis Bay Beach Resort
Outdoor pool, pool umbrellas, pool loungers

Ibis Bay Beach Resort

2.5 star property
8.0 out of 10, Very good, (1721)
"Didn’t have regular TV."
The price is HK$1,919
HK$2,368 total
includes taxes & fees
26 Jan - 27 Jan
Ibis Bay Beach Resort
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.

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.