Search Vacation Homes in Cudjoe Key

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Compare 495 Vacation Homes in Cudjoe Key with updated reviews, rates, and availability.

Outdoor dining
Poolside Cottage #411
10.0 out of 10, Exceptional, (16)
"My son and his new wife stayed here for their honeymoon and they absolutely loved it!"
The price is $216
$369 total
includes taxes & fees
May 28 - May 29
Poolside Cottage #411
Pool
Great Family Vacation Rental.
10.0 out of 10, Exceptional, (3)
"The townhome was nice and is located in a quaint community. The pool area was beautiful. We found that we needed to Uber into Key West since parking is very limited and we were told the bus service is often not on time."
Great Family Vacation Rental.
Outdoor dining
Poolside Cottage #412
10.0 out of 10, Exceptional, (6)
"Perfect location. Poolside. Friendly staff, excellent service ~ Brandy!!!"
The price is $216
$369 total
includes taxes & fees
Jun 5 - Jun 6
Poolside Cottage #412
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Outdoor pool, a heated pool
Casa Cay West Beautiful Tropical House 3 bedrooms 2 KING suites POOL 2 mi beach
10.0 out of 10, Exceptional, (388)
"We loved our stay at Judy’s place. It’s a short drive into downtown key west. We rented a car and took Ubers, which were readily available. The house was exactly as described and so nicely decorated. Had everything you need, including plenty of towels for bath and pool. Pool was very clean and relaxing. The house feels very private with all of the landscaping. Across the street is a great brewery, coffee shop and pizza/Italian restaurant. Judy was so helpful and responsive. Highly recommend to...
Casa Cay West Beautiful Tropical House 3 bedrooms 2 KING suites POOL 2 mi beach
Property grounds
Oceanfront Paradise w Dock for your 35' boat and Huge Tiki and Firepit. Dogs OK
10.0 out of 10, Exceptional, (5)
"We enjoyed our stay. This property was in a quiet area with a beautiful sunrise from the patio."
Oceanfront Paradise w Dock for your 35' boat and Huge Tiki and Firepit. Dogs OK
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…
Property grounds
Bayview Manor at Paradise Harbor with Private Pool and Dock!
10.0 out of 10, Exceptional, (4)
"his property was perfectly located in Key West and is accessible to all of the destinations via a short walk. Check-in was easy, the accommodations are beautiful, really appreciated our stay."
Bayview Manor at Paradise Harbor with Private Pool and Dock!
Beach
WATERFRONT fresh & cozy 2 bedroom 35 sea wall New UV light air purification
9.8 out of 10, Exceptional, (168)
"We kept our boat there and it was perfect it was blowing and the canal stayed protected from waves and they had everything you needed on site would definitely stay again."
WATERFRONT fresh & cozy 2 bedroom 35 sea wall New UV light air purification
Exterior
Oceanside Paradise: Kayaks, Free WiFi, A/C, Grill, Elevated Deck, 24hr Security
9.8 out of 10, Exceptional, (217)
"My daughter and I stayed in Cudjoe Key to be close to Key West. The location was good. The unit had everything we needed both inside and out. We grilled and cooked which was great. The beds were comfortable. Unfortunately, the weather did not cooperate and excursions were cancelled so we spent more time in Key West than we had planned. But the unit had lots of games and the TV had the tennis channel which was very nice. All in all, it was a good time."
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, (183)
"Very nice"
Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill
Property grounds
Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes
9.8 out of 10, Exceptional, (202)
"Fantastic property and location, our 2nd time there. Melanie, the host, is super responsive. I would highly recommend."
The price is $350
$442 total
includes taxes & fees
May 29 - May 30
Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes
Beach
**DOCKSIDE DAYDREAMS @ COCONUT MALLORY** Marina Villa + LAST KEY SERVICES…
9.8 out of 10, Exceptional, (73)
"It was easy to slip into island time with this great location. Place was immaculate, PM Charity, was present shortly after we arrived to be sure we had everything and answer any questions. We quickly made our way to the lovely pool for a swim. We walked on the dock and ducked into Gumbo's right on the water on property. The bar tender was welcoming and encouraged my teens to play a round of pool.It was truly a flawless stay."
**DOCKSIDE DAYDREAMS @ COCONUT MALLORY** Marina Villa + LAST KEY SERVICES…
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
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
A heated pool
Island Therapy
9.8 out of 10, Exceptional, (40)
"My family and I had a wonderful time here. There is a lot to do in the neighborhood when you aren't out in the water. I would stay hear again!!"
Island Therapy
Property grounds
Banana Breeze: Oceanview 4-bedroom home with private pool & lush landscaping!
9.8 out of 10, Exceptional, (79)
"Carpets were soiled, floors seemed not mopped and the refrigerator was dented."
Banana Breeze: Oceanview 4-bedroom home with private pool & lush landscaping!
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
Pool | Outdoor pool, a heated pool
Luxury 2/2 1/2 - FREE PARKING, WIFI, BIKES, BIG POOL, NEWLY RENOVATED
9.6 out of 10, Exceptional, (90)
"House was exactly as stated. We enjoyed it there. Close enough to downtown to enjoy it. Nice touch having the bikes there to use! Condo pool was great too. We enjoyed the amenities! Would stay again if we came back to the area!"
Luxury 2/2 1/2 - FREE PARKING, WIFI, BIKES, BIG POOL, NEWLY RENOVATED
Property grounds
Seaside Retreat: Waterfront Home with private heated pool & lush landscaping
9.6 out of 10, Exceptional, (46)
"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
Living area | TV
OFF CALL ~ Rustic, Nautical Decor With King Primary Suite & Heated Pool!
9.6 out of 10, Exceptional, (64)
"Enjoyed our stay…..Dan was very helpful with the smart tv issue…."
OFF CALL ~ Rustic, Nautical Decor With King Primary Suite & Heated Pool!
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, (202)
"Fantastic property and location, our 2nd time there. Melanie, the host, is super responsive. I would highly recommend."
The price is $350
$442 total
includes taxes & fees
May 29 - May 30
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, (174)
"Great location, 23 miles to Key West. View from deck is breathtaking."
Ocean Perch, Dock, Open Water Views, 80' Heated Pool, Tennis, 20 Min to Key West
Balcony
Just 20 miles from Key West! Oceanfront, dockage, swimming pool
8.4 out of 10, Very Good, (89)
"Good place. 3 bed rooms all with Queen size beds. It was perfect for us. We sat on the porch mostly when we were there and played games. Not a long ride to Key West. Overall- we were happy and would stay there again."
Just 20 miles from Key West! Oceanfront, dockage, swimming pool
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 Vacation Homes information

Number of reviews
1,528
Accommodation
495 Vacation Homes
Lowest Price
$216
Highest Price
$599

Recent reviews of Cudjoe Key hotels
Expedia verified reviews

The Laureate Key West

The Laureate Key West

5/5 Excellent
"Charming, lovely hotel. Would definitely return and not hesitate to recommend!"
A verified traveler stayed at The Laureate Key West
Posted 1 day ago
The Laureate Key West