Search Vacation Homes in Cudjoe Key

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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.
$547 nightly
The price is $609
Jan 10 - Jan 11, 2026
Total with taxes and fees
DECEMBER SAVE 60% OFF! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

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

DECEMBER SAVE 60% OFF OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!
Cudjoe Key
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.
$551 nightly
The price is $613
Jan 15 - Jan 16, 2026
Total with taxes and fees
DECEMBER SAVE 60% OFF OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!

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
$550 nightly
The price is $611
Jan 4 - Jan 5, 2026
Total with taxes and fees
Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access

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
$589 nightly
The price is $654
Jan 4 - Jan 5, 2026
Total with taxes and fees
Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near 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
$605 nightly
The price is $672
Jan 4 - Jan 5, 2026
Total with taxes and fees
Waterfront Getaway with 23' Seawall, Boat Access, Outdoor Dining & Cozy Interiors

105 - Newly renovated house Oceanside and Pool

105 - Newly renovated house Oceanside and Pool
Cudjoe Key
$735 nightly
The price is $777
Jan 21 - Jan 22, 2026
Total with taxes and fees
105 - Newly renovated house Oceanside and Pool

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
8.0 out of 10, Very Good, (1)
"It was a short trip but we enjoyed our stay! "
United States
Jennifer S.
$658 nightly
The price is $732
Jan 2 - Jan 3, 2026
Total with taxes and fees
Waterfront 2BR/2BA with 35' Dock, Bikes & Kayaks – Island Breeze Keys Escape

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.
$641 nightly
The price is $712
Jan 4 - Jan 5, 2026
Total with taxes and fees
Reel Island Retreat #273 at Venture Out in the Florida Keys

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
$668 nightly
The price is $741
Jan 3 - Jan 4, 2026
Total with taxes and fees
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

Waterfront 2BR/2BA | 35' Seawall for 32' Boat | Beautiful Sunrises on Cudjoe Key
2.0 star property
Cudjoe Key
$692 nightly
The price is $770
Jan 4 - Jan 5, 2026
Total with taxes and fees
Waterfront 2BR/2BA | 35' Seawall for 32' Boat | Beautiful Sunrises on Cudjoe Key

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.
$663 nightly
The price is $737
Jan 6 - Jan 7, 2026
Total with taxes and fees
Relax at Keys Time – 2BR Waterfront Rental w/ Kayaks, Bikes, and Boat Dock

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.
$920 nightly
The price is $1,021
Jan 3 - Jan 4, 2026
Total with taxes and fees
Oceanfront Cudjoe Key Home - 35' Seawall, Sunrise Views, Pool & Pet-Friendly

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.
$670 nightly
The price is $744
Jan 4 - Jan 5, 2026
Total with taxes and fees
Mahi House #440 - 35' seawall

Stunning Ocean Views! 2BR Waterfront Home w/ Dock in Gated Keys Community

Stunning Ocean Views! 2BR Waterfront Home w/ Dock in Gated Keys Community
Cudjoe Key
10.0 out of 10, Exceptional, (11)
"outstanding views and house is spotless!"
United States
Virginia L.
$816 nightly
The price is $906
Jan 13 - Jan 14, 2026
Total with taxes and fees
Stunning Ocean Views! 2BR Waterfront Home w/ Dock in Gated Keys Community

Post Card Point #319 - Ocean Views!

Post Card Point #319 - Ocean Views!
Cudjoe Key
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.
$857 nightly
The price is $951
Jan 2 - Jan 3, 2026
Total with taxes and fees
Post Card Point #319 - Ocean Views!

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
$958 nightly
The price is $1,065
Jan 3 - Jan 4, 2026
Total with taxes and fees
Open-water home with stunning views, 42' seawall for 40' boat, modern updates, large balcony

Direct Oceanfront Cudjoe Key Escape 56' Dock, Ocean Views, Kayaks, Bikes & Pool

Direct Oceanfront Cudjoe Key Escape 56' Dock, Ocean Views, Kayaks, Bikes & Pool
Cudjoe Key
9.8 out of 10, Exceptional, (143)
"Super relaxing! Great location! Wonderful views! "
United States
Allicia W.
$903 nightly
The price is $1,004
Jan 5 - Jan 6, 2026
Total with taxes and fees
Direct Oceanfront Cudjoe Key Escape 56' Dock, Ocean Views, Kayaks, Bikes & Pool

Fishermen's Paradise | Pool, dock, gorgeous home

Fishermen's Paradise | Pool, dock, gorgeous home
Big Pine Key
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.
$1,278 nightly
The price is $1,406
Jan 21 - Jan 22, 2026
Total with taxes and fees
Fishermen's Paradise | Pool, dock, gorgeous home

Old Florida Style, wrap around porch, boat basin for dockage, open water

Old Florida Style, wrap around porch, boat basin for dockage, open water
Little Torch Key
9.6 out of 10, Exceptional, (88)
"This place really had it all , one of my best stays yet anywhere. "
United States
Charles M.
$739 nightly
The price is $821
Jan 1 - Jan 2, 2026
Total with taxes and fees
Old Florida Style, wrap around porch, boat basin for dockage, open water

Kelly's Kabin - Adorable Private Summerland Key Cottage

Kelly's Kabin - Adorable Private Summerland Key Cottage
Summerland Key
9.8 out of 10, Exceptional, (122)
"We enjoyed our stay! Great little house and location. "
United States
Lisa K.
$461 nightly
The price is $511
Dec 22 - Dec 23
Total with taxes and fees
Kelly's Kabin - Adorable Private Summerland Key Cottage
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
631
Accommodation
849 Vacation Homes
Lowest Price
$511
Highest Price
$1,406

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