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Our top choices for Cudjoe Key holiday homes

9.4 out of 10, Exceptional, (101)
"Great location. "
United States
Davian k.
The price is HK$2,324
HK$4,857 total
includes taxes & fees
13 Jan - 14 Jan 2026
SAVE BIG $$$ JANUARY! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
9.8 out of 10, Exceptional, (82)
"The place is clean and convenient for anyone wanting to spend time on the water in the keys"
United States
Ubaldo G.
The price is HK$2,327
HK$4,861 total
includes taxes & fees
18 Jan - 19 Jan 2026
SAVE BIG $$ JANUARY! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!
The price is HK$1,633
HK$4,814 total
includes taxes & fees
13 Jan - 14 Jan 2026
Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access
The price is HK$2,041
HK$5,273 total
includes taxes & fees
13 Jan - 14 Jan 2026
Waterfront Getaway with 23' Seawall, Boat Access, Outdoor Dining & Cozy Interiors
The price is HK$1,984
HK$5,271 total
includes taxes & fees
13 Jan - 14 Jan 2026
Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West
8.4 out of 10, Very good, (119)
"Great experience "
United States
Peyton S.
The price is HK$2,529
HK$5,148 total
includes taxes & fees
2 Jan - 3 Jan 2026
Just 20 miles from Key West! Oceanfront, dockage, swimming pool
The price is HK$2,778
HK$6,074 total
includes taxes & fees
21 Jan - 22 Jan 2026
105 - Newly renovated house Oceanside and Pool
8.0 out of 10, Very good, (1)
"It was a short trip but we enjoyed our stay! "
United States
Jennifer S.
The price is HK$2,449
HK$5,787 total
includes taxes & fees
13 Jan - 14 Jan 2026
Waterfront 2BR/2BA with 35' Dock, Bikes & Kayaks – Island Breeze Keys Escape
8.8 out of 10, Excellent, (148)
"Boat access and docking spaces could be improved but overall not terrible. Spent a week here and enjoyed the stay. Quiet decent location. "
United States
bryan c.
The price is HK$2,918
HK$5,633 total
includes taxes & fees
2 Jan - 3 Jan 2026
Cudjoe Cottages, swimming pool, just 20 miles from Key West
10.0 out of 10, Exceptional, (1)
"Very clean! Good location. "
United States
January M.
The price is HK$2,655
HK$6,131 total
includes taxes & fees
4 Jan - 5 Jan 2026
Waterfront 2BR/2BA | 35' Seawall for 32' Boat | Beautiful Sunrises on Cudjoe Key
9.6 out of 10, Exceptional, (7)
"We really enjoyed our stay here. We really loved sitting on the back porch by the water and the closeness to the community pool and courts. "
United States
Lindsay C.
The price is HK$2,247
HK$5,547 total
includes taxes & fees
4 Jan - 5 Jan 2026
Reel Island Retreat #273 at Venture Out in the Florida Keys
10.0 out of 10, Exceptional, (4)
"Beautiful "
United States
Lisa P.
The price is HK$4,085
HK$7,942 total
includes taxes & fees
3 Jan - 4 Jan 2026
Oceanfront Cudjoe Key Home - 35' Seawall, Sunrise Views, Pool & Pet-Friendly
9.2 out of 10, Wonderful, (29)
"Close to Key West and lots of great boating"
United States
Simon S.
The price is HK$2,451
HK$5,808 total
includes taxes & fees
6 Jan - 7 Jan 2026
Relax at Keys Time – 2BR Waterfront Rental w/ Kayaks, Bikes, and Boat Dock
The price is HK$2,408
HK$5,803 total
includes taxes & fees
13 Jan - 14 Jan 2026
Florida Keys Canal-Front 2BR/2BA w/ 35' Seawall, Dock & Spacious Comfort
10.0 out of 10, Exceptional, (12)
"outstanding views and house is spotless!"
United States
Virginia L.
The price is HK$3,061
HK$7,123 total
includes taxes & fees
13 Jan - 14 Jan 2026
Stunning Ocean Views! 2BR Waterfront Home w/ Dock in Gated Keys Community

Holiday Home in Cudjoe Key

Mahi House #440 - 35' seawall
8.8 out of 10, Excellent, (3)
"Clean and excellent water access"
United States
Chris P.
The price is HK$2,451
HK$5,800 total
includes taxes & fees
4 Jan - 5 Jan 2026
Mahi House #440 - 35' seawall
The price is HK$4,489
HK$8,316 total
includes taxes & fees
13 Jan - 14 Jan 2026
Open-water home with stunning views, 42' seawall for 40' boat, modern updates, large balcony
9.8 out of 10, Exceptional, (143)
"Super relaxing! Great location! Wonderful views! "
United States
Allicia W.
The price is HK$4,081
HK$7,888 total
includes taxes & fees
13 Jan - 14 Jan 2026
Direct Oceanfront Cudjoe Key Escape 56' Dock, Ocean Views, Kayaks, Bikes & Pool

Holiday Home in Cudjoe Key

Post Card Point #319 - Ocean Views!
10.0 out of 10, Exceptional, (49)
"The Post Card Point was absolutely stunning. Very clean and welcoming. Perfect access to fishing, diving, lobstering! Filet Table right on the water. We loved it :) will definitely be back!!!"
United States
Dave J.
The price is HK$3,265
HK$7,383 total
includes taxes & fees
13 Jan - 14 Jan 2026
Post Card Point #319 - Ocean Views!
9.8 out of 10, Exceptional, (24)
"The location was very nice and secluded. The house was perfect for a family of five. The pool was great spent a lot of time in it. Lots to do in the area. The only complaint we had is the master bedroom bed mattress needs to be replaced. It seemed like it was very old possibly even broken communication with Karen was perfect. Everything about the trip was good :) "
United States
Michelle S.
The price is HK$8,800
HK$11,050 total
includes taxes & fees
21 Jan - 22 Jan 2026
Fishermen's Paradise | Pool, dock, gorgeous home
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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Top Cudjoe Key Hotel Reviews

Find out more about Cudjoe Key

Cudjoe Key Vacation Homes information

Number of reviews
690
Accommodation
849 Vacation Homes
Lowest Price
HK$4,814
Highest Price
HK$11,050

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