Cudjoe Key Vacation Packages
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Your Cudjoe Key Vacation
Say bye-bye to the hassle of planning and hello to a Cudjoe Key vacation package. With everything organized before you go, you can focus on discovering this city, starting with Sugarloaf Shores, which is great for families, fishing and views. Make your trip to Cudjoe Key even more fulfilling by including some sightseeing. Florida Keys Beaches, Sugarloaf Beach and Upper Sugarloaf Sound are among the most popular attractions worth exploring. Whoever you're going away with and whether your budget is big or small, your ultimate Cudjoe Key vacation is just a few clicks away with Expedia.
Top Cudjoe Key Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Cavalier Hotel South Beach
South Beach
Price was CA $2,655, price is now CA $1,319 per person
CA $1,319
per person
Jan 17 - Jan 24
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Miami (MIA)
8.6/10 Excellent! (1,002 reviews)
I loved that it was an unique property & easily accessible to everything.
Reviewed on Nov 5, 2026
The Retreat Collection at 1 Hotel & Homes South Beach
South Beach
Price was CA $15,066, price is now CA $7,188 per person
CA $7,188
per person
Feb 1 - Feb 4
found 14 hours ago
Roundtrip non-stop flight included
Montreal (YUL) 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
The Marlin Hotel
South Beach
Price was CA $2,561, price is now CA $1,373 per person
CA $1,373
per person
Jan 17 - Jan 24
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Miami (MIA)
9.2/10 Wonderful! (1,005 reviews)
Nice hotel. Room was clean. Bed and pillows very comfortable. Bathroom was tight but shower was nice.
There was some light that shown in from the back alley.
We didn’t like the fact that there was a mandatory $32.00 fee per person for a beach chair and towel. The weather was rainy but you still had to pay for it. Nice location a block to the beach. Lots of restaurants nearby.
Reviewed on Nov 4, 2026
CH Luxury Condos & Studios On The Beach
Hollywood Beach
Price was CA $3,764, price is now CA $2,046 per person
CA $2,046
per person
Dec 23 - Dec 29
found 6 hours ago
Roundtrip flight included
Montreal (YMQ) to Miami (MIA)
8.6/10 Excellent! (153 reviews)
Awesome location to the beach, bars, restaurants, and of course, the boardwalk. We loved the beautiful rooftop pool area. The staff everywhere were extremely helpful and communicative. Any questions we had were answered almost immediately through messaging. Very clean with comfortable beds. Had all the amenities we needed for a long weekend stay. If you're planning a visit to the Hollywood Beach area, we would highly recommend it.
Reviewed on Oct 20, 2026
Cudjoe Key Hotel Deals
Cottage with swimming pool and dockage, just minutes to Key West!
Cudjoe Key FL
9/10 Wonderful! (175 reviews)
"The view from the docks was great. Convenient location to go to all the key islands. Very relaxing. Enjoyed our stay for sure."
Reviewed on Oct 13, 2026
Private Oceanfront Cottage with dockage, pool just minutes to Key West!
Cudjoe Key FL
8.8/10 Excellent! (186 reviews)
"Finding the property by GPS is not easy. Turning at the truck sign works."
Reviewed on Oct 19, 2026
Cottage with Pool and Boat Dockage just minutes to Key West!
Cudjoe Key FL
8.6/10 Excellent! (170 reviews)
"This is an old quaint property.Right on the Atlanticside.Two docks.The pool is modern and very nice.Cottage is ideal for two.Old but clean"
Reviewed on Oct 27, 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.
What to do in Cudjoe Key
Discover US East Coast Self Guided Audio Tour
CA $205
per traveller
Full-Day Tour of Florida Keys Including Aquarium Encounters from Key West
CA $239
per adult
Frequently asked questions
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
