
Cudjoe Key Vacations from $382
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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.
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 $800, price is now $382 per person
$382
per person
Aug 19 - Aug 23
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Miami (MIA)
8.6/10 Excellent! (1,005 reviews)
I called 3 times for info, too book and for directions and parking and each time I called, it answered quickly and the front ask helped with whatever I needed. Check In was easy. Our rooms were spotlessly clean. We ate outside at their restaurant and service was quick and efficient. The food was excellent. We really loved their open coffee and ice water bar. It was a very nice amenity . They have an ice machine down stairs and I was down there filling up my ice bucket for my water bottles. E Z no problems. The location is great. The beach is across the street. The staff is warm and personable. Even when we are outside we never had to ID our selves as hotel guests, they just knew and always gave us a % discount which is really nice.
Reviewed on Jun 13, 2026

Casablanca Miami Beach
North Beach
Price was $5,491, price is now $2,130 per person
$2,130
per person
Sep 10 - Sep 14
found 5 hours ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
5.8/10 (324 reviews)
Room was clean and great location beside the beach. Room had kitchette and big fridge, microwave etc. so was great.
It was dated and internet didn't work in our room but worked well in the lobby. Great value for money :) happy with it.
Reviewed on Feb 22, 2026



Bay Breeze Premium Apartments By Eskape Collection
Save 100% on your flight
Price was $740, price is now $396 per person
$396
per person
Sep 10 - Sep 14
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.8/10 Excellent! (222 reviews)
The staff were very accommodating! The location was perfect. However, the apartment did not have basic kitchen items like dish soap, paper towels or spices, I had to DoorDash those items.
Reviewed on Jun 13, 2026
Cudjoe Key Hotel Deals

Blue Flamingo Resort Key West
3820 North Roosevelt Boulevard Key West FL
Fully refundableReserve now, pay when you stay
$175 nightly
The price is $197 total per night from Jun 21 to Jun 22
$197 total
Jun 21 - Jun 22
Total with taxes and fees
8.4/10 Very Good! (2,407 reviews)
"Blue Flamingo was a wonderful hotel and I will go back. The pools were lovely, but it would have been nice if one pool was designated to children and the other for adults. The room was lovely as well. Our only problem was with housekeeping. Upon cleaning our room, they took all the dirty towels but ..."
Reviewed on Jun 17, 2026

Hilton Garden Inn Key West / The Keys Collection
3850 N Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
$140 nightly
The price is $157 total per night from Jun 29 to Jun 30
$157 total
Jun 29 - Jun 30
Total with taxes and fees
8/10 Very Good! (1,239 reviews)
"We had a great time. No complimentary breakfast as advertised but the shuttle to downtown was great"
Reviewed on Jun 17, 2026

Margaritaville Beach House Key West
2001 South Roosevelt Boulevard Key West FL
Fully refundableReserve now, pay when you stay
$264 nightly
The price is $297 total per night from Jun 21 to Jun 22
$297 total
Jun 21 - Jun 22
Total with taxes and fees
8.8/10 Excellent! (1,848 reviews)
"The hotel was nice, but not as nice as some of the other Margaritaville resorts we’ve stayed at. The pool area is small and unfortunately the beach across the street was unusable. That’s not the hotel’s fault, but part of the reason I chose to stay there was the proximity to the beach. The rooms ..."
Reviewed on Jun 16, 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.
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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