Holiday Homes in Cudjoe Key

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Featured Holiday Homes in Cudjoe Key

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 AU$572
per night
14 May - 15 May
Poolside Cottage #411
Property grounds
Casa Capri Beautiful Tropical style house with 3 King Suites POOL 2 mi to BEACH
10.0 out of 10, Exceptional, (225)
"Judy was extremely responsive and a joy to work with. This was a great property for our purposes. We needed three separate sleeping rooms with their own baths. We also needed a full kitchen and the patio grill for meal prep. All needs were met!"
Casa Capri Beautiful Tropical style house with 3 King Suites POOL 2 mi to BEACH
Property grounds
Old Florida Style, wrap around porch, boat basin for dockage, open water
9.8 out of 10, Exceptional, (43)
"This property is awesome!! Great location! Had a blast on the porch and paddle boarding from the front lagoon. Only issue was the AC leaked in ceiling and master bedroom bc we turned them down too low. This should be noted on house rules to avoid it happening to future renters. Other than that small issue I would love to return and stay here again ASAP. Thank you Susan for your hospitality!"
Old Florida Style, wrap around porch, boat basin for dockage, open water
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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 AU$681
per night
29 May - 30 May
Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes
Property grounds
Beautiful Family-Friendly, Dock, Marina, Heated Pool, near Key West, MM21.5
10.0 out of 10, Exceptional, (193)
"Love the location. Great little gated neighborhood. KW is an easy drive and there is a lot to do in the immediate area. Would definitely stay again."
Beautiful Family-Friendly, Dock, Marina, Heated Pool, near Key West, MM21.5
Fridge, microwave, oven, stovetop
Nautical Wheeler: Waterfront Home with private Pool & lush landscaping
9.8 out of 10, Exceptional, (72)
"The whole process for a newbie was absolutely easy. The property was 5 star. The experience was perfect. Had two issues both were taken care of immediately. Will use again."
Nautical Wheeler: Waterfront Home with private Pool & lush landscaping
Property grounds
Seaside Retreat: Waterfront Home with private heated pool & lush landscaping
9.6 out of 10, Exceptional, (45)
"This was a beautiful house in a great location. Very large, easily fit everyone comfortably. Awesome."
Seaside Retreat: Waterfront Home with private heated pool & lush landscaping
A heated pool
Dock, Htd 80' Pool, Deep Channel, 15 Min To Key West
9.6 out of 10, Exceptional, (168)
"Stayed with another couple and thoroughly enjoyed the cottage. The porch is an awesome place to enjoy your morning coffee and the dock is an even better place to enjoy the sunset and a glass of wine! The property has all the amenities for a great vacation."
Dock, Htd 80' Pool, Deep Channel, 15 Min To Key West
Fridge, microwave, oven, stovetop
Kelly's Kabin - Adorable Private Summerland Key Cottage
9.8 out of 10, Exceptional, (98)
"House was conveniently located, cute and exactly what we needed"
The price is AU$791
per night
13 May - 14 May
Kelly's Kabin - Adorable Private Summerland Key Cottage
Property grounds
Banana Breeze: Oceanview 4-bedroom home with private pool & lush landscaping!
9.8 out of 10, Exceptional, (78)
"stayed here with friends and family for my wedding in Key West. The house was gorgeous. The view of the water was gorgeous. Hanging out at the observation deck was also gorgeous. Pictures do not give enough justice to the amazing place this is. will stay there again."
Banana Breeze: Oceanview 4-bedroom home with private pool & lush landscaping!
Pool
NEWLY REMODELED KITCHEN!! PET FRIENDLY! 3 Bedroom 3 bathroom home. Sleeps 8
9.6 out of 10, Exceptional, (184)
"The house was great and the weekend trip was awesome!"
NEWLY REMODELED KITCHEN!! PET FRIENDLY! 3 Bedroom 3 bathroom home. Sleeps 8
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
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
Pool
Fanta Sea in Cudjoe Key!
10.0 out of 10, Exceptional, (9)
"Ocean breezes, star-filled skies, and calming open water views were augmented by an adorable and perfectly clean house with absolutely everything we needed. Kayaks and bikes made for fun outings, and Key West was close enough for several day trips. We would stay here again in a heartbeat."
Fanta Sea in Cudjoe Key!
Property grounds
**PLANTATION TROPICALE @ CASA EAST** Grand Estate & Pool + LAST KEY SERVICES…
10.0 out of 10, Exceptional, (34)
"We traveled from Michigan celebrating my mother’s 75th birthday. I don’t know much about the company last key rentals. The concierge, Victor and awesome person and awesome man very knowledgeable. Very pleasant made me and my family feel right at home. To last key Victor went above and beyond to answer any questions and to make everyone feel as comfortable and was very supportive and knowledgeable of the community and surrounding areas. To the owner you have amazing property."
**PLANTATION TROPICALE @ CASA EAST** Grand Estate & Pool + LAST KEY SERVICES…
Exterior
One of the very few beach houses with a daily, rental license in the Keys.
9.0 out of 10, Wonderful, (47)
"Layout of house and location are perfect. The owners were very communicative and responsive."
One of the very few beach houses with a daily, rental license in the Keys.
Beach
WATERFRONT fresh & cozy 2 bedroom 35 sea wall New UV light air purification
9.8 out of 10, Exceptional, (165)
"Relaxing and beautiful!"
WATERFRONT fresh & cozy 2 bedroom 35 sea wall New UV light air purification
Property grounds
Palms Resort at Sugarloaf Beach - Main House
9.6 out of 10, Exceptional, (10)
"Our family of 11 ( me, my husband, our daughters, their husbands and children ages 10 mos to 4 years old) stayed for a week at the end of Feb. The house was immaculate, views were breathtaking, amenities perfect. The beach/ocean was perfect for the kids, sand play, shell searches, and shallow water! We saw dolphins not far from the dock! Tom was fantastic and helped in every way possible from tips of where to eat, things to do, even supplied a baby gate to keep our lil ones safe! We all were sad...
Palms Resort at Sugarloaf Beach - Main House
Beach nearby
Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West
9.0 out of 10, Wonderful, (59)
"Overall everything was nice. There were a few issues which I addressed with our host. Shower door broken, and no gas in gas grill. Location was beautiful and quiet setting. Our family enjoyed our Cudjoe Key stay"
Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West
A heated pool
Captain's Daughter: Oversized home for the whole family w/private pool & dock
9.8 out of 10, Exceptional, (106)
"When the listing said property had a dock I assumed it would have a water view. It didn’t. That being said the pool and backyard were very nice. The house was well appointed and very clean. Lots of towels, extra pillows and blankets available. Water pressure and warm water was adequate. Two off street parking spots at the front door and plenty of off street parking always available. Would rent this property again"
Captain's Daughter: Oversized home for the whole family w/private pool & dock
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 property types in Cudjoe Key

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 AU$681
per night
29 May - 30 May
Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes
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
Lake
Cudjoe Key, FL RV Resort RV Lot
8.0 out of 10, Very good, (4)
"Had a wonderful stay"
The price is AU$197
per night
5 May - 6 May
Cudjoe Key, FL RV Resort RV Lot
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.

Cudjoe Key Holiday Homes information

Number of reviews
1,912
Accommodation
480 Holiday Homes
Lowest Price
AU$572
Highest Price
AU$796

Recent Reviews in Cudjoe Key
Expedia verified reviews