Cudjoe Key Holiday Rentals

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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, (219)
"Perfect location with sunset views and kayaking "
The price is HK$2,333
HK$5,783 total
includes taxes & fees
7 Jan - 8 Jan 2025
Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes
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!
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, (186)
"We picked this place for the view and it didnt disappoint. We brought our electric bikes and used them pretty much everywhere. "
Ocean Perch, Dock, Open Water Views, 80' Heated Pool, Tennis, 20 Min to Key West
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, (232)
"The unit was spotless and perhaps one of the best equipped places we have stayed at with VRBO. Everything worked, the utensil drawers were overflowing, extra towels and bedding were provided. There was even a printer available. There were 6 bicycles to pick from and several kayaks (although it was too windy to use this time). Everything in the description is accurate. 5 of 5 rating."
Oceanside Paradise: Kayaks, Free WiFi, A/C, Grill, Elevated Deck, 24hr Security
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, (199)
"The Property was as advertised. Great location, had everything we needed, served as both a fantastic base camp between outings and home base. We were able to experience everything we wanted for Thanksgiving as well as hit all the Florida Key highlights (Key West, Bahia Honda , and Piegon Key to list a few), the Venture Out location amenities and activities were a fantastic fit for us as well. Would 100% come back and we are even looking for future dates already. "
Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill
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, (96)
"This place was nice and came as advertised. Location is solid and near a few good restaurants and bars. It could have been a little cleaner but overall was in good shape. Would stay again. Price is good for what you get. "
The price is HK$1,750
HK$4,192 total
includes taxes & fees
23 Dec - 24 Dec
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, (145)
"I was here for a wedding in key west..i had a great time on Cudjoe Key. I would definitely stay at this location again..the pool are is very nice and you can see the sunrise every morning. "
Comfortable Waterfront Vacation Rental
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, (170)
"The check was very smooth; everyone friendly and helpful with local suggestions. Location was great! Nice and quiet"
The price is HK$1,003
HK$1,906 total
includes taxes & fees
23 Dec - 24 Dec
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, (106)
"Nice for affordable price "
The price is HK$1,603
HK$2,896 total
includes taxes & fees
7 Jan - 8 Jan 2025
Aqua Lodges at Hurricane Hole Marina
Poolside Cottage #411
Outdoor dining

Poolside Cottage #411

10.0 out of 10, Exceptional, (33)
"Really nice place to stay. We had a pleasant stay and the property was great "
The price is HK$2,628
HK$4,072 total
includes taxes & fees
8 Jan - 9 Jan 2025
Poolside Cottage #411
34’ Catamaran Sailboat
Interior

34’ Catamaran Sailboat

9.6 out of 10, Exceptional, (28)
"The property was great and the host was very responsive to communication. "
34’ Catamaran Sailboat
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!
ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub!
Terrace/patio

ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub!

9.0 out of 10, Wonderful, (31)
"Peaceful and paradise!"
ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub!
Sunshine Key RV Resort & Marina
Sun deck

Sunshine Key RV Resort & Marina

2.0 star property
8.8 out of 10, Excellent, (141)
"Nice place to relax"
Sunshine Key RV Resort & Marina
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$5,443
HK$6,847 total
includes taxes & fees
3 Jan - 4 Jan 2025
The Crystalmarine Suite – Rustic Luxury on the Sea
Real World MTV House-18 to 22 guests, Not Just a House Your Own Private Resort
Aerial view

Real World MTV House-18 to 22 guests, Not Just a House Your Own Private Resort

9.6 out of 10, Exceptional, (82)
"Great trip with 16 people for a 50th birthday party. Host was very helpful and informative throughout the trip. Great for large groups."
Real World MTV House-18 to 22 guests, Not Just a House Your Own Private 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$2,646
HK$4,825 total
includes taxes & fees
11 Jan - 12 Jan 2025
The Caroline Suite | 1 bed, 1 bath condo w/shared pool
Luxury 62' Yacht! In a Beautiful Resort
Outdoor pool, a heated pool

Luxury 62' Yacht! In a Beautiful Resort

10.0 out of 10, Exceptional, (7)
"Excellent boat, excellent stay. Would love to return."
Luxury 62' Yacht! In a Beautiful 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.
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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, (219)
"Perfect location with sunset views and kayaking "
The price is HK$2,333
HK$5,783 total
includes taxes & fees
7 Jan - 8 Jan 2025
Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes
Oceans Edge Key West Resort, Hotel & Marina
6 outdoor pools, free pool cabanas, pool umbrellas

Oceans Edge Key West Resort, Hotel & Marina

4.0 star property
8.8 out of 10, Excellent, (1531)
"Great place to stay "
The price is HK$2,327
HK$3,081 total
includes taxes & fees
8 Jan - 9 Jan 2025
Oceans Edge Key West Resort, Hotel & Marina
Beachside Resort & Residences
Outdoor pool, pool umbrellas, pool loungers

Beachside Resort & Residences

3.5 star property
8.4 out of 10, Very good, (1014)
"Just nice. No worries"
The price is HK$1,452
HK$2,027 total
includes taxes & fees
6 Jan - 7 Jan 2025
Beachside Resort & Residences
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.