Holiday Homes in Cudjoe Key

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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 €529
includes taxes & fees
10 Jan - 11 Jan 2026
DECEMBER SAVE 60% OFF! 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 €531
includes taxes & fees
18 Jan - 19 Jan 2026
DECEMBER SAVE 60% OFF OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!
The price is €535
includes taxes & fees
4 Jan - 5 Jan 2026
Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access
The price is €676
includes taxes & fees
21 Jan - 22 Jan 2026
105 - Newly renovated house Oceanside and Pool
The price is €571
includes taxes & fees
4 Jan - 5 Jan 2026
Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West
The price is €588
includes taxes & fees
4 Jan - 5 Jan 2026
Waterfront Getaway with 23' Seawall, Boat Access, Outdoor Dining & Cozy Interiors
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 €635
includes taxes & fees
2 Jan - 3 Jan 2026
Waterfront 2BR/2BA with 35' Dock, Bikes & Kayaks – Island Breeze Keys Escape
10.0 out of 10, Exceptional, (3)
"Beautiful "
United States
Lisa P.
The price is €894
includes taxes & fees
3 Jan - 4 Jan 2026
Oceanfront Cudjoe Key Home - 35' Seawall, Sunrise Views, Pool & Pet-Friendly
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 €625
includes taxes & fees
4 Jan - 5 Jan 2026
Reel Island Retreat #273 at Venture Out in the Florida Keys
9.2 out of 10, Wonderful, (28)
"Close to Key West and lots of great boating"
United States
Simon S.
The price is €642
includes taxes & fees
6 Jan - 7 Jan 2026
Relax at Keys Time – 2BR Waterfront Rental w/ Kayaks, Bikes, and Boat Dock
The price is €649
includes taxes & fees
3 Jan - 4 Jan 2026
Florida Keys Canal-Front 2BR/2BA w/ 35' Seawall, Dock & Spacious Comfort
Waterfront 2BR/2BA | 35' Seawall for 32' Boat | Beautiful Sunrises on Cudjoe Key

Holiday Home in Cudjoe Key

Mahi House #440 - 35' seawall
10.0 out of 10, Exceptional, (2)
"Clean and excellent water access"
United States
Chris P.
The price is €649
includes taxes & fees
5 Jan - 6 Jan 2026
Mahi House #440 - 35' seawall
10.0 out of 10, Exceptional, (11)
"outstanding views and house is spotless!"
United States
Virginia L.
The price is €858
includes taxes & fees
23 Jan - 24 Jan 2026
Stunning Ocean Views! 2BR Waterfront Home w/ Dock in Gated Keys Community
The price is €925
includes taxes & fees
3 Jan - 4 Jan 2026
Open-water home with stunning views, 42' seawall for 40' boat, modern updates, large balcony

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 €833
includes taxes & fees
2 Jan - 3 Jan 2026
Post Card Point #319 - Ocean Views!
9.8 out of 10, Exceptional, (143)
"Super relaxing! Great location! Wonderful views! "
United States
Allicia W.
The price is €885
includes taxes & fees
6 Jan - 7 Jan 2026
Direct Oceanfront Cudjoe Key Escape 56' Dock, Ocean Views, Kayaks, Bikes & Pool
6.0 out of 10, (1)
"The house was not thoroughly cleaned. The cabinets and under the place mats were dirty. When we opened the pack and play it had an orange substance caked all over inside. We tried to watch tv and remote had no batteries, we tried the second remote and that didn’t work either. "
United States
Heather H.
The price is €654
includes taxes & fees
22 Jan - 23 Jan 2026
Charming 3-bedroom house in Big Pine Key near Beach and Key West
9.8 out of 10, Exceptional, (23)
"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 €1,232
includes taxes & fees
21 Jan - 22 Jan 2026
Fishermen's Paradise | Pool, dock, gorgeous home
9.6 out of 10, Exceptional, (88)
"This place really had it all , one of my best stays yet anywhere. "
United States
Charles M.
The price is €718
includes taxes & fees
1 Jan - 2 Jan 2026
Old Florida Style, wrap around porch, boat basin for dockage, open water
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 Holiday Homes information

Number of reviews
510
Accommodation
849 Holiday Homes
Lowest Price
€529
Highest Price
€1,232

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