
Cudjoe Key Vacations from $447
Book a Hotel + Flight or Car together to unlock savings
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.
The Latest Cudjoe Key vacation packages
Price found within the past 48 hours. Click for updated prices.

Cavalier Hotel South Beach
South Beach
Save 100% on your flight
Price was $869, price is now $447 per person
$447
per person
Jan 21 - Jan 24
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Miami (MIA)
8.4/10 Very Good! (1,004 reviews)
Room was clean. Staff was friendly beach, restaurants and shops nearby. Also a convenient parking garage within walking distance.
Reviewed on Nov 4, 2025

The Shelborne By Proper, a Member of Design Hotels
South Beach
Price was $1,685, price is now $725 per person
$725
per person
Jan 21 - Jan 24
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Miami (MIA)
9.8/10 Exceptional! (39 reviews)
Fantastic experience. One of the best hotels we have stayed at. Shout out to Jenny, Marta , Shane and Louis, William and Josh and all of the other wonderful staff. Definitely recommend it and will certainly go back !
Reviewed on Nov 1, 2025



EAST Miami Residences
Downtown Miami
Price was $1,839, price is now $967 per person
$967
per person
Jan 8 - Jan 12
found 20 hours ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
9/10 Wonderful! (78 reviews)
Staff were very helpful and courteous! Amenities were excellent and room was cleaned everyday. Location was the best.
Reviewed on Nov 3, 2025
Cudjoe Key Hotel Deals

Oceans Edge Key West Resort, Hotel & Marina
5950 Peninsular Avenue, Key West, FL
Fully refundableReserve now, pay when you stay
$206 nightly
The price is $232 total per night from Nov 16 to Nov 17
$232 total
Nov 16 - Nov 17
Total with taxes and fees
8.8/10 Excellent! (1,733 reviews)
We’ve stayed here twice now. Staff is great, the shuttle into town is super convenient (hi Jeffrey!). We love that you can use the kayaks or paddleboards every day. The tiki hut crew is the best! The place is clean and I feel safe walking around there. It’s well lit and easy to navigate.
Reviewed on Nov 2, 2025

Blue Flamingo Resort Key West
3820 North Roosevelt Boulevard, Key West, FL
Fully refundableReserve now, pay when you stay
$157 nightly
The price is $177 total per night from Nov 18 to Nov 19
$177 total
Nov 18 - Nov 19
Total with taxes and fees
7.8/10 Good! (1,648 reviews)
Beautiful room, great view, love the pools, bars and lawn games
Reviewed on Nov 3, 2025

Beachside Resort & Residences
3841 N Roosevelt Blvd, Key West, FL
Fully refundableReserve now, pay when you stay
$193 nightly
The price is $217 total per night from Nov 12 to Nov 13
$217 total
Nov 12 - Nov 13
Total with taxes and fees
8.6/10 Excellent! (1,655 reviews)
Staff good but never clean our room
Reviewed on Nov 3, 2025
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.
Find the Best Cudjoe Key Vacation Packages
Cudjoe Key Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Key West Intl. Airport (EYW) |
Population | 1,750 |
Top Sights | Florida Keys Beaches, Sugarloaf Beach and Big Pine Key Flea Market |
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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.


















