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Our top choices for Cudjoe Key vacation homes

DECEMBER SAVE 60% OFF! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

DECEMBER SAVE 60% OFF! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.4 out of 10, Exceptional, (101)
"Great location. "
United States
Davian k.
The price is ¥46,587
¥96,407 total
includes taxes & fees
Jan 10 - Jan 11, 2026
DECEMBER SAVE 60% OFF! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds!

Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds!
Cudjoe Key
7.6 out of 10, Good, (13)
"Good experience. The property is well place and the Venture is really nice and quiet."
United States
Primeau J.
The price is ¥34,746
¥74,926 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds!

Island Time #110 Ocean Views - Cudjoe Key

Island Time #110 Ocean Views - Cudjoe Key
2.5 star property
Cudjoe Key
9.4 out of 10, Exceptional, (12)
"Our family had an amazing vacation! We love the house and hope to come back!! "
United States
Tammy G.
The price is ¥36,810
¥101,244 total
includes taxes & fees
Dec 16 - Dec 17
Island Time #110 Ocean Views - Cudjoe Key

Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access

Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access
Cudjoe Key
The price is ¥29,448
¥92,028 total
includes taxes & fees
Dec 16 - Dec 17
Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access

Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West

Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West
Cudjoe Key
8.8 out of 10, Excellent, (155)
"The property was excellent. The location was perfect. Quiet and relaxing. "
United States
Jonathan K.
The price is ¥38,563
¥87,945 total
includes taxes & fees
Dec 16 - Dec 17
Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West

Just 20 miles from Key West! Oceanfront, dockage, swimming pool

Just 20 miles from Key West! Oceanfront, dockage, swimming pool
Cutthroat Harbor Estates
8.4 out of 10, Very Good, (118)
"Great experience "
United States
Peyton S.
The price is ¥35,057
¥83,534 total
includes taxes & fees
Dec 16 - Dec 17
Just 20 miles from Key West! Oceanfront, dockage, swimming pool

Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West

Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West
2.0 star property
Cudjoe Key
The price is ¥32,720
¥96,175 total
includes taxes & fees
Dec 16 - Dec 17
Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West

Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West

Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West
Cudjoe Key
8.6 out of 10, Excellent, (89)
"We had a great time and will be back. "
United States
Michelle K.
The price is ¥46,743
¥107,937 total
includes taxes & fees
Dec 16 - Dec 17
Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West

Waterfront Getaway with 23' Seawall, Boat Access, Outdoor Dining & Cozy Interiors

Waterfront Getaway with 23' Seawall, Boat Access, Outdoor Dining & Cozy Interiors
2.0 star property
Cudjoe Key
The price is ¥40,900
¥104,600 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Waterfront Getaway with 23' Seawall, Boat Access, Outdoor Dining & Cozy Interiors

Galleon Getaway #533- Oceanfront Community

Galleon Getaway #533- Oceanfront Community
Cudjoe Key
The price is ¥31,902
¥95,568 total
includes taxes & fees
Dec 17 - Dec 18
Galleon Getaway #533- Oceanfront Community

Florida Keys Canal-Front 2BR/2BA w/ 35' Seawall, Dock & Spacious Comfort

Florida Keys Canal-Front 2BR/2BA w/ 35' Seawall, Dock & Spacious Comfort
Cudjoe Key
The price is ¥32,720
¥96,175 total
includes taxes & fees
Dec 16 - Dec 17
Florida Keys Canal-Front 2BR/2BA w/ 35' Seawall, Dock & Spacious Comfort

Waterfront 2BR/2BA with 35' Dock, Bikes & Kayaks – Island Breeze Keys Escape

Waterfront 2BR/2BA with 35' Dock, Bikes & Kayaks – Island Breeze Keys Escape
2.0 star property
Cudjoe Key
The price is ¥49,080
¥114,114 total
includes taxes & fees
Jan 2 - Jan 3, 2026
Waterfront 2BR/2BA with 35' Dock, Bikes & Kayaks – Island Breeze Keys Escape

105 - Newly renovated house Oceanside and Pool

105 - Newly renovated house Oceanside and Pool
Cudjoe Key
The price is ¥57,338
¥122,965 total
includes taxes & fees
Dec 16 - Dec 17
105 - Newly renovated house Oceanside and Pool

Reel Island Retreat #273 at Venture Out in the Florida Keys

Reel Island Retreat #273 at Venture Out in the Florida Keys
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 ¥44,990
¥111,538 total
includes taxes & fees
Dec 16 - Dec 17
Reel Island Retreat #273 at Venture Out in the Florida Keys

Relax at Keys Time – 2BR Waterfront Rental w/ Kayaks, Bikes, and Boat Dock

Relax at Keys Time – 2BR Waterfront Rental w/ Kayaks, Bikes, and Boat Dock
Cudjoe Key
9.2 out of 10, Wonderful, (28)
"Close to Key West and lots of great boating"
United States
Simon S.
The price is ¥44,990
¥111,538 total
includes taxes & fees
Dec 16 - Dec 17
Relax at Keys Time – 2BR Waterfront Rental w/ Kayaks, Bikes, and Boat Dock

Mahi House #440 - 35' seawall

Mahi House #440 - 35' seawall
Cudjoe Key
10.0 out of 10, Exceptional, (2)
"Clean and excellent water access"
United States
Chris P.
The price is ¥44,990
¥111,538 total
includes taxes & fees
Dec 16 - Dec 17
Mahi House #440 - 35' seawall

Waterfront 2BR/2BA | 35' Seawall for 32' Boat | Beautiful Sunrises on Cudjoe Key

Waterfront 2BR/2BA | 35' Seawall for 32' Boat | Beautiful Sunrises on Cudjoe Key
2.0 star property
Cudjoe Key
The price is ¥53,170
¥119,180 total
includes taxes & fees
Dec 16 - Dec 17
Waterfront 2BR/2BA | 35' Seawall for 32' Boat | Beautiful Sunrises on Cudjoe Key

Salty Breeze #161 - Canal Front Venture Out Home on Cudjoe Key

Salty Breeze #161 - Canal Front Venture Out Home on Cudjoe Key
2.0 star property
Cudjoe Key
9.0 out of 10, Wonderful, (7)
"Great place! Perfect location"
United States
Troy B.
The price is ¥53,170
¥121,673 total
includes taxes & fees
Dec 16 - Dec 17
Salty Breeze #161 - Canal Front Venture Out Home on Cudjoe Key

Oceanfront Cudjoe Key Home - 35' Seawall, Sunrise Views, Pool & Pet-Friendly

Oceanfront Cudjoe Key Home - 35' Seawall, Sunrise Views, Pool & Pet-Friendly
Cudjoe Key
10.0 out of 10, Exceptional, (3)
"Beautiful "
United States
Lisa P.
The price is ¥77,710
¥152,555 total
includes taxes & fees
Dec 17 - Dec 18
Oceanfront Cudjoe Key Home - 35' Seawall, Sunrise Views, Pool & Pet-Friendly

Open-water home with stunning views, 42' seawall for 40' boat, modern updates, large balcony

Open-water home with stunning views, 42' seawall for 40' boat, modern updates, large balcony
2.0 star property
Cudjoe Key
Open-water home with stunning views, 42' seawall for 40' boat, modern updates, large balcony
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

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Cudjoe Key Vacation Homes information

Number of reviews
525
Accommodation
849 Vacation Homes
Lowest Price
¥74,926
Highest Price
¥152,555

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