Cudjoe Key Holiday Rentals

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Holiday Rentals in Cudjoe Key

Poolside Cottage #411
Outdoor dining
Poolside Cottage #411
10.0 out of 10, Exceptional, (14)
"This place was so quiet and comfortable and was the perfect stay for us in Key West. The hosts are top notch."
The price is HK$1,690
HK$2,889 total
includes taxes & fees
28 May - 29 May
Poolside Cottage #411
52' Power Catamaran Yacht at Luxury Resort Marina
Outdoor dining
52' Power Catamaran Yacht at Luxury Resort Marina
10.0 out of 10, Exceptional, (11)
"We had a great time about Blue Jeans! Louie is an amazing host, as responsive as possible, also took us out for a cruise around Key West, AC works great! Easy Golf kart ride from the marina to down town key west. Pool at the marina was nice as well."
52' Power Catamaran Yacht at Luxury Resort Marina
SIGNIFICANTLY DISCOUNTED!! 45' Sea Ray Yacht Located in 5 Star Resort!
Property grounds
SIGNIFICANTLY DISCOUNTED!! 45' Sea Ray Yacht Located in 5 Star Resort!
10.0 out of 10, Exceptional, (9)
"Sunset cruise was amazing around key west with captain lombardi"
SIGNIFICANTLY DISCOUNTED!! 45' Sea Ray Yacht Located in 5 Star Resort!
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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, (6)
"Great property, staff was excellent and the captain was fantastic. We will be back !!!"
Luxury 62' Yacht! In a Beautiful Resort
Poolside Cottage #412
Outdoor dining
Poolside Cottage #412
10.0 out of 10, Exceptional, (6)
"Perfect location. Poolside. Friendly staff, excellent service ~ Brandy!!!"
The price is HK$1,690
HK$2,850 total
includes taxes & fees
9 May - 10 May
Poolside Cottage #412
Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes
Property grounds
Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes
9.8 out of 10, Exceptional, (201)
"The property and townhouse were all very nice. If your wanting to go to Key West multiple times during the week, this location is a quick 21 miles. Townhouse was very accommodating for two couples. Pool and tiki patio areas were all clean, plenty of seating, and quiet. Only con would be bicycles need attention due to flat tires. We would book this property in the future."
The price is HK$2,738
HK$3,455 total
includes taxes & fees
13 May - 14 May
Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes
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, (216)
"Beautiful house in a gated community. Comfortable beds and a well stocked kitchen. 35 min to Key West, close to beaches and great restaurants nearby. We would not hesitate to stay here again!"
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, (180)
"very well stocked and clean, Will be back for sure"
Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill
Luxury High End, 2 Bikes, Highspeed Wi-Fi, Work station, Pool, Hot Tub, Gym
Pool
Luxury High End, 2 Bikes, Highspeed Wi-Fi, Work station, Pool, Hot Tub, Gym
9.8 out of 10, Exceptional, (257)
"This property and host exceeded all of our expectations. It was spacious, comfortable, and welcoming with its amazing kitchen, breezy rooms, and friendly neighbors. The hosts were a pleasure to work with and easy to reach whenever we wished to communicate with them. 10/10 would return to this property. I highly recommend it!"
Luxury High End, 2 Bikes, Highspeed Wi-Fi, Work station, Pool, Hot Tub, Gym
**CONCH IN THE TREETOPS @ 1800 ATLANTIC** Beach Condo / Pool + LAST KEY SERVICES
Pool
**CONCH IN THE TREETOPS @ 1800 ATLANTIC** Beach Condo / Pool + LAST KEY SERVICES
9.8 out of 10, Exceptional, (147)
"Host was an outstanding communicator. Check-in process was fully remote and seamless! Thank you, Victor Redd! (Also the Key Lime pie was a hit!). The property itself was great and has its own little private oasis with the pool and private beach. Our place didn’t have the ocean view, but we didn’t need to pay all the extra money per night for that because we spent our time at 1800 Atlantic either at the pool, at Smithers Beach right next door, or Sleeping! The rest of the time we spent enjoying...
**CONCH IN THE TREETOPS @ 1800 ATLANTIC** Beach Condo / Pool + LAST KEY SERVICES
Tom's Spectacular OceanFront 3 Bdrm Endless Atlantic view, Key West Amazing
A heated pool
Tom's Spectacular OceanFront 3 Bdrm Endless Atlantic view, Key West Amazing
9.8 out of 10, Exceptional, (102)
"Excellent top drawer"
Tom's Spectacular OceanFront 3 Bdrm Endless Atlantic view, Key West Amazing
Old Florida Style, wrap around porch, boat basin for dockage, open water
Property grounds
Old Florida Style, wrap around porch, boat basin for dockage, open water
9.8 out of 10, Exceptional, (43)
"Great quiet location on the water. Quick communication with the property manager and easy check in and check out process. Definitely recommend it."
Old Florida Style, wrap around porch, boat basin for dockage, open water
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, (80)
"Great place for a group to hang out in Key West"
The price is HK$15,637
HK$29,679 total
includes taxes & fees
13 May - 14 May
Real World MTV House-18 to 22 guests, Not Just a House Your Own Private Resort
Comfortable Waterfront Vacation Rental
Sun-loungers, beach towels
Comfortable Waterfront Vacation Rental
9.4 out of 10, Exceptional, (136)
"Right price for location 35 minutes from Key West."
Comfortable Waterfront Vacation Rental
Tropical Getaway in Paradise.
Outdoor pool, a heated pool
Tropical Getaway in Paradise.
9.4 out of 10, Exceptional, (79)
"The property was everything it said in the listing. It was clean, comfortable and a grest place to sit and relax after a day full of adventures. We were visiting our son who lives on Summerland Key and works for the Boy Scouts. It was centrally located so we could go east or west and explore. Thanks for making this trip enjoyable, and relaxing. Sincerely, the Meyers'"
Tropical Getaway in Paradise.
34’ Catamaran Sailboat
Fridge, cookware/dishes/utensils, dining tables
34’ Catamaran Sailboat
9.4 out of 10, Exceptional, (22)
"So glad we stayed here! It is exactly what I was looking for. A unique way to visit Key West. It was nice to open the hatches and have a nice breeze and great view of the stars. He has a nice bathroom with shower in the car port. The host was great with communication and was really cool. Definitely recommend"
34’ Catamaran Sailboat
Steps To The Beach And The Sunrise-No Contact Check-In
Beach
Steps To The Beach And The Sunrise-No Contact Check-In
9.4 out of 10, Exceptional, (93)
"After you have visited Duval Street with all the restaurants, museums and shopping you will appreciate what this condo has to offer. This condo offers you the relaxation that Key West also offers. The beach is directly across the street from this unit. Plus there are beach lounge chairs, umbrellas, kayaks, and paddle boards you can rent. The condo book is filled with all the information you need."
Steps To The Beach And The Sunrise-No Contact Check-In
Mother Ocean: Waterfront 4 Bedroom 3 Bath luxury Oceanfront home with pool
Property grounds
Mother Ocean: Waterfront 4 Bedroom 3 Bath luxury Oceanfront home with pool
9.4 out of 10, Exceptional, (44)
"Wonderful place. We rented 7 bikes and were able to store them in the garage and ride wherever we needed to go. Didn’t need to go much since the place was so great, between the pool and the spacious open kitchen and decks we were able to cook and make cocktails."
Mother Ocean: Waterfront 4 Bedroom 3 Bath luxury Oceanfront home with pool
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
9.2 out of 10, Wonderful, (173)
"Wonderful location and community. Enjoyed the ping pong, tennis & pickleball! Bikes & kayaks would have been great. The house was comfortable and cute. Had to call host for a repair and was taken care of within an hour. Cleanliness could have been better - dusty and cabinets/drawers could use attention. Very happy with our stay."
Ocean Perch, Dock, Open Water Views, 80' Heated Pool, Tennis, 20 Min to Key West
Cozy, Perfect Conch Cottage!
Pool
Cozy, Perfect Conch Cottage!
9.2 out of 10, Wonderful, (29)
"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!
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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

Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes
Property grounds
Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes
9.8 out of 10, Exceptional, (201)
"The property and townhouse were all very nice. If your wanting to go to Key West multiple times during the week, this location is a quick 21 miles. Townhouse was very accommodating for two couples. Pool and tiki patio areas were all clean, plenty of seating, and quiet. Only con would be bicycles need attention due to flat tires. We would book this property in the future."
The price is HK$2,738
HK$3,455 total
includes taxes & fees
13 May - 14 May
Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes
Havana Cabana at Key West
Outdoor pool, pool loungers
Havana Cabana at Key West
4.0 star property
8.8 out of 10, Excellent, (1440)
"The pool and courtyard was beautiful, food was delicious, bar and staff was very nice, great service. We enjoyed our stay."
The price is HK$2,339
HK$3,142 total
includes taxes & fees
13 May - 14 May
Havana Cabana at Key West
Margaritaville Beach House Key West
Beach nearby, white sand
Margaritaville Beach House Key West
4.0 star property
8.6 out of 10, Excellent, (1740)
"Nice"
The price is HK$1,830
HK$2,555 total
includes taxes & fees
27 May - 28 May
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.

Search for holiday rentals in Cudjoe Key on Expedia! You can easily find your home rentals, villas, holiday apartments in Cudjoe Key using one of the methods below:

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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

The Laureate Key West

The Laureate Key West

5/5 Excellent
"Very nice. We’re having a good time in the Key's. "
A verified traveller stayed at The Laureate Key West
Posted 9 hours ago
The Laureate Key West