Cudjoe Key Pet-friendly Vacations
Book a Pet-friendly Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $2,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top Pet-friendly vacation packages in Cudjoe Key
Price found within the past 48 hours. Click for updated prices.
The Retreat Collection at 1 Hotel & Homes South Beach
South Beach
$10,794
per person
Sep 29 - Oct 4
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8/10 Very Good! (1 review)
Horrible checkin / checkout... Would never stay there again...Double charged me entire stay and still fighting to get someone to refund 2nd one that is so clearly a duplicate for same stay....
Reviewed on Jun 22, 2016
5* Pet-friendly vacations in Cudjoe Key
Price found within the past 48 hours. Click for updated prices.
The Retreat Collection at 1 Hotel & Homes South Beach
South Beach
$10,794
per person
Sep 29 - Oct 4
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8/10 Very Good! (1 review)
Horrible checkin / checkout... Would never stay there again...Double charged me entire stay and still fighting to get someone to refund 2nd one that is so clearly a duplicate for same stay....
Reviewed on Jun 22, 2016
3 Night Pet-friendly vacations in Cudjoe Key
Price found within the past 48 hours. Click for updated prices.
The Retreat Collection at 1 Hotel & Homes South Beach
South Beach
$7,348
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8/10 Very Good! (1 review)
Horrible checkin / checkout... Would never stay there again...Double charged me entire stay and still fighting to get someone to refund 2nd one that is so clearly a duplicate for same stay....
Reviewed on Jun 22, 2016
4 Night Pet-friendly vacations in Cudjoe Key
Price found within the past 48 hours. Click for updated prices.
The Retreat Collection at 1 Hotel & Homes South Beach
South Beach
$8,222
per person
Oct 8 - Oct 12
found 18 hours ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8/10 Very Good! (1 review)
Horrible checkin / checkout... Would never stay there again...Double charged me entire stay and still fighting to get someone to refund 2nd one that is so clearly a duplicate for same stay....
Reviewed on Jun 22, 2016
Top Pet-friendly Cudjoe Key Hotels
Luxury Pull Thru Rv lot with access to all the Resorts amenities!
Cudjoe Key FL
- 14 min drive from Florida Keys Beaches
An oceanfront vacation awaits at this family-friendly resort, where pets are welcome (fees apply). Bring along your four-legged friend for a pet-friendly ...
9.4/10 Exceptional! (16 reviews)
"This place was so much fun i want to move here!!! Everything worked out smoothly and was a great time. Will be back!"
Reviewed on Jul 25, 2026
ISLAND PARADISE
Cudjoe Key FL
- 14 min drive from Florida Keys Beaches
This family-friendly resort welcomes dogs (fees apply). Bring your four-legged friend with you for a pet-friendly getaway.
10/10 Exceptional! (34 reviews)
"We absolutely loved our stay here. The place was immaculate. The kitchen was fully stocked with anything you might need to cook. The bed was very comfortable. We will definitely book another stay here in the future!"
Reviewed on Aug 4, 2026
Cottage with Pool and Dockage, just minutes to Key West
Cudjoe Key FL
- 12 min drive from Florida Keys Beaches
Stay at this cottage in Summerland Key. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Florida Keys Beaches and Upper Sugarloaf Key are ...
9.4/10 Exceptional! (176 reviews)
"This location is very convenient for me as my family lives 5 miles from this place. Very clean and the host works well with the customer."
Reviewed on Aug 2, 2026
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.
Things to do
Key West Jet Ski Tour: The Only 2-Hour Island Lap.
$1,254
per traveler
More vacations you might like
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
