Cudjoe Key Vacation Rentals

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Our top choices for Cudjoe Key vacation rentals

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Cudjoe Key
8.2 out of 10, Very Good, (50)
"Great area. Quiet and comfortable "
United States
nancy c.
$286 nightly
The price is $317
Dec 14 - Dec 15
Total with taxes and fees
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Charming cottages, dockage, pool, just minutes to Key West

Charming cottages, dockage, pool, just minutes to Key West
Cudjoe Key
8.6 out of 10, Excellent, (120)
"Jennifer was very nice and accommodating."
United States
Randy G.
$296 nightly
The price is $329
Dec 15 - Dec 16
Total with taxes and fees
Charming cottages, dockage, pool, just minutes to Key West

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.
$391 nightly
The price is $434
Dec 14 - Dec 15
Total with taxes and fees
DECEMBER SAVE 60% OFF! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

Endless Summer Hideaway - lot 181

Endless Summer Hideaway - lot 181
Cudjoe Key
$199 nightly
The price is $212
Dec 14 - Dec 15
Total with taxes and fees
Endless Summer Hideaway - lot 181

Atlantic View Luxury Villa with Pool

Atlantic View Luxury Villa with Pool
3.5 star property
Summerland Key
10.0 out of 10, Exceptional, (1)
"We were here for a night and it was great. A nice rustic feel on a big property, with good view. "
United States
Preetam
$874 nightly
The price is $983
Dec 14 - Dec 15
Total with taxes and fees
Atlantic View Luxury Villa with Pool

Seabreeze Escape WF RV Lot 489

Seabreeze Escape WF RV Lot 489
Cudjoe Key
8.0 out of 10, Very Good, (1)
$245 nightly
The price is $263
Dec 14 - Dec 15
Total with taxes and fees
Seabreeze Escape WF RV Lot 489

Island Time #110 Ocean Views - Cudjoe Key

Island Time #110 Ocean Views - Cudjoe Key
2.5 star property
Cudjoe Key
9.6 out of 10, Exceptional, (11)
"Our family had an amazing vacation! We love the house and hope to come back!! "
United States
Tammy G.
$585 nightly
The price is $650
Dec 15 - Dec 16
Total with taxes and fees
Island Time #110 Ocean Views - Cudjoe Key

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.
$504 nightly
The price is $560
Dec 14 - Dec 15
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
$533 nightly
The price is $592
Dec 14 - Dec 15
Total with taxes and fees
Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access

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.
$432 nightly
The price is $480
Jan 6 - Jan 7, 2026
Total with taxes and fees
Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds!

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.
$509 nightly
The price is $564
Dec 15 - Dec 16
Total with taxes and fees
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.
$483 nightly
The price is $536
Dec 15 - Dec 16
Total with taxes and fees
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
$560 nightly
The price is $621
Dec 14 - Dec 15
Total with taxes and fees
Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West

Galleon Getaway #533- Oceanfront Community

Galleon Getaway #533- Oceanfront Community
Cudjoe Key
$551 nightly
The price is $611
Dec 14 - Dec 15
Total with taxes and fees
Galleon Getaway #533- Oceanfront Community

Saltwater Serenity #392 - Ocean Views on Cudjoe Key

Saltwater Serenity #392 - Ocean Views on Cudjoe Key
Cudjoe Key
10.0 out of 10, Exceptional, (7)
"We had a great time. Everything was as listed. "
United States
Deah C.
$579 nightly
The price is $644
Dec 14 - Dec 15
Total with taxes and fees
Saltwater Serenity #392 - Ocean Views on Cudjoe Key

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.
$629 nightly
The price is $698
Dec 14 - Dec 15
Total with taxes and fees
Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West

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
$557 nightly
The price is $618
Dec 14 - Dec 15
Total with taxes and fees
Florida Keys Canal-Front 2BR/2BA w/ 35' Seawall, Dock & Spacious Comfort

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
$598 nightly
The price is $665
Jan 4 - Jan 5, 2026
Total with taxes and fees
Waterfront Getaway with 23' Seawall, Boat Access, Outdoor Dining & Cozy Interiors

Endless Ocean Views - RV589

Endless Ocean Views - RV589
Cudjoe Key
$307 nightly
The price is $331
Dec 14 - Dec 15
Total with taxes and fees
Endless Ocean Views - RV589

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
$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
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

Price trends for vacation rentals in Cudjoe Key

Less expensive
More expensive
This month
Next month
November
July
$315
$357
Month
Price
January
$357
February
$376
March
$345
April
$343
May
$349
June
$346
July
$381
August
$350
September
$265
October
$261
November
$240
December
$315
Price trend information excludes taxes and fees and is based on base rates for a nightly stay for 2 adults found in the last 7 days on our site and averaged for commonly viewed vacation rentals in Cudjoe Key. Select dates and complete search for nightly totals inclusive of taxes and fees.

Find out more about Cudjoe Key

Everything you need to know about Cudjoe Key vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Cudjoe Key vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Cudjoe Key vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Cudjoe Key vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Cudjoe Key. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Cudjoe Key in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $271 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Cudjoe Key rentals

At Expedia, we put the best Cudjoe Key vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Cudjoe Key rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Cudjoe Key vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Cudjoe Key. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.