Holiday Homes in Cudjoe Key

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Featured Holiday Homes in Cudjoe Key and around

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!

INCOMMUNICADO ~ Waterfront 2 BR/2 Ba w/ Dockage and Hot Tub!

9.6 out of 10, Exceptional, (30)
"This was a very smooth, perfect 5 night visit. The property offered us everything that we could need. It was a short drive to Duval St and all of the activities in Key West yet the property was very peaceful with a wonderful waterfront patio that we sat out on and enjoyed. The hot tub was a nice treat as well. I have to mention the incredible responsiveness of the property manager. Every question that I had they responded to within minutes which was very much appreciated. "
INCOMMUNICADO ~ Waterfront 2 BR/2 Ba w/ Dockage and Hot Tub!

OFF CALL ~ Rustic, Nautical Decor With King Primary Suite & Heated Pool!

9.6 out of 10, Exceptional, (75)
"This was our first time staying in an air b&b. We absolutely loved our stay! We wish we would have booked for longer. We highly recommend this place as it was super clean, spacious, and relaxing! We will be back! "
OFF CALL ~ Rustic, Nautical Decor With King Primary Suite & Heated Pool!

Beachside @ Torchview Waterfront Retreat

9.8 out of 10, Exceptional, (37)
"I had a wonderful 3 weeks stay at Beachside@Torchview. I loved the privacy of the house, the gorgeous sunset views, and the peaceful mornings sitting out on the deck while drinking my morning coffee. I would highly recommend this house for anyone looking for a quiet getaway in the busy Florida Keys. It was everything I had hoped for, and I will definitely be staying here again if I decide to return to the Keys next year. The house was very clean and suited my needs perfectly, and the host...
Beachside @ Torchview Waterfront Retreat

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 €515
includes taxes & fees
8 Jan - 9 Jan 2025
Poolside Cottage #411

Banana Breeze: Oceanview 4-bedroom home with private pool & lush landscaping!

9.8 out of 10, Exceptional, (97)
"Great place to stay very kid friendly and a short golfcart ride to everything "
Banana Breeze: Oceanview 4-bedroom home with private pool & lush landscaping!

Old Florida Style, wrap around porch, boat basin for dockage, open water

9.8 out of 10, Exceptional, (58)
"Our family of five adults and a dog had a fantastic week at this beautiful house! We had plenty of space, it was super clean and well kept. The countertop ice maker was definitely appreciated! We didn’t cook but all the tools you could need are there. We did place an Instacart order from Publix for a few things and delivery was no problem. Lots of restaurants are within a short drive and Kiki’s right down the road was a plus and had great food. We spent most mornings and evenings hanging out on...
Old Florida Style, wrap around porch, boat basin for dockage, open water

CORAL CABANA ~ Lush Porch Views of the Pool & Gardens, near Golf Course!

9.8 out of 10, Exceptional, (110)
"Ok location. 10 minutes to key west. Nice pool"
CORAL CABANA ~ Lush Porch Views of the Pool & Gardens, near Golf Course!

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 €731
includes taxes & fees
7 Jan - 8 Jan 2025
Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes

Poolside Cottage #412

9.8 out of 10, Exceptional, (15)
"Quiet area of the key west neighbors quiet, nice bike ride to key west and grocery store was close by. Would recommend renting from the resort"
The price is €512
includes taxes & fees
6 Jan - 7 Jan 2025
Poolside Cottage #412

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!

NEWLY REMODELED KITCHEN!! PET FRIENDLY! 3 Bedroom 3 bathroom home. Sleeps 8

9.6 out of 10, Exceptional, (196)
"Exactly as advertised with an incredible host. We had a great time in Key West! "
NEWLY REMODELED KITCHEN!! PET FRIENDLY! 3 Bedroom 3 bathroom home. Sleeps 8

HAVANA DAYDREAMING ~ Waterfront 1 BR/1 Ba w/ Dockage & Hot Tub!

9.8 out of 10, Exceptional, (22)
"Clean, cozy and cute "
HAVANA DAYDREAMING ~ Waterfront 1 BR/1 Ba w/ Dockage & Hot Tub!

3/4 Time: Oceanfront, luxury home with private pool & lush landscaping

9.8 out of 10, Exceptional, (69)
"We had an amazing stay, this place was everything shown as well as more!! We at first were worried about the location being so far from Duval, however we could not have been more wrong. EVERYTHING you could want or need you can walk to, we were very happy with our stay and the host. Thank you. Don’t hesitate to book this unit, we will be back!!"
3/4 Time: Oceanfront, luxury home with private pool & lush landscaping

Luxury 2/2 1/2 - FREE PARKING, WIFI, BIKES, BIG POOL, NEWLY RENOVATED

9.6 out of 10, Exceptional, (99)
"Everything was good"
Luxury 2/2 1/2 - FREE PARKING, WIFI, BIKES, BIG POOL, NEWLY RENOVATED

CASA DE VINO ~ Amazing Price for Charming Townhouse with Pool & Tiki!

9.8 out of 10, Exceptional, (76)
"Overall the home was really good and in a very good location. We would definitely rent again. The check in process was great and instructions were clear on how to operate everything. Parking was great and the home had everything we needed to cook in and room to spread out and to also sit and eat together as a family."
CASA DE VINO ~ Amazing Price for Charming Townhouse with Pool & Tiki!

COCONUT TELEGRAPH ~ Waterfront 2 BR/2Ba in Cudjoe Key w/ Dockage & Parking!

9.4 out of 10, Exceptional, (28)
"Super nice place Comfortable Couch Comfortable Bed"
COCONUT TELEGRAPH ~ Waterfront 2 BR/2Ba in Cudjoe Key w/ Dockage & Parking!

Southern Comfort: Luxury Waterfront Home with private pool & lush landscaping

9.6 out of 10, Exceptional, (52)
"Great property for families."
Southern Comfort: Luxury Waterfront Home with private pool & lush landscaping

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 €530
includes taxes & fees
23 Dec - 24 Dec
Just 20 miles from Key West! Oceanfront, dockage, swimming pool

Nautical Wheeler: Waterfront Home with private Pool & lush landscaping

9.8 out of 10, Exceptional, (83)
"The house was fantastic and very clean! Beautiful views, and great location! "
Nautical Wheeler: Waterfront Home with private Pool & lush landscaping
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 property types in Cudjoe Key

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 €731
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!

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

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
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.