Cudjoe Key Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 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
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.
The Marlin Hotel
South Beach
Price was CA $2,147, price is now CA $1,087 per person
CA $1,087
per person
Oct 9 - Oct 13
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
9.2/10 Wonderful! (1,002 reviews)
Perfect location for South Beach. One block off Ocean Drive with bars, restaurants, clubs, etc. all within walking distance & a great Italian restaurant on-property too.
Reviewed on Jul 13, 2026
Casablanca Miami Beach
North Beach
Price was CA $4,327, price is now CA $1,962 per person
CA $1,962
per person
Aug 20 - Aug 27
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Miami (MIA)
5.8/10 (324 reviews)
This was a very disappointing stay. The apartment was dirty, dusty, and hot. The temperature stayed around 77–78°F all night, yet the only bedding provided was thick comforters, making it impossible to sleep comfortably.
When I simply asked for thin bed sheets, the host became argumentative instead of trying to help. They kept saying they were a private owner, as if that somehow excused poor customer service or making guests uncomfortable. It wasn’t until I contacted Expedia that the host responded by providing what I initially asked for.
I didn’t want to spend my vacation dealing with unnecessary conflict, so we checked out after the first night instead of staying for the remaining five nights of our six-night reservation. I would not stay here again.
Reviewed on Jul 2, 2026
The Retreat Collection at 1 Hotel & Homes South Beach
South Beach
Price was CA $17,014, price is now CA $8,005 per person
CA $8,005
per person
Aug 24 - Aug 28
found 1 day ago
Roundtrip flight included
Montreal (YMQ) 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
Bentley Hotel South Beach
South Beach
Price was CA $2,416, price is now CA $1,496 per person
CA $1,496
per person
Sep 19 - Sep 26
found 5 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Miami (MIA)
9.4/10 Exceptional! (941 reviews)
Great location, really helpful staff, rooms were a great size, very generous breakfast. Would definitely stay again
Reviewed on Jul 14, 2026
Cudjoe Key Hotel Deals
Private Oceanfront Cottage with dockage, pool just minutes to Key West!
Cudjoe Key FL
8.6/10 Excellent! (177 reviews)
"Great location and price. 20 ish mins from Key West. Private dock and boat ramp shared with the other rentals on the property."
Reviewed on Jul 9, 2026
Beachside Resort & Residences
3841 N Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
The price is CA $180 per night from Aug 16 to Aug 17
CA $180
CA $337 total
Aug 16 - Aug 17
includes taxes & fees
Blue Flamingo Resort Key West
3820 North Roosevelt Boulevard Key West FL
Fully refundableReserve now, pay when you stay
The price is CA $188 per night from Aug 9 to Aug 10
CA $188
CA $291 total
Aug 9 - Aug 10
includes taxes & fees
8.4/10 Very good! (2,537 reviews)
"100 percent recommend!!"
Reviewed on Jul 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.
What to do in Cudjoe Key
Discover US East Coast Self Guided Audio Tour
CA $206
per traveller
Full-Day Tour of Florida Keys Including Aquarium Encounters from Key West
CA $240
per adult
Historic Key West Old Town Trolley Hop-On Hop-Off Tour
CA $79
per adult
88% of travellers recommend
Frequently asked questions
Explore a world of travel with Expedia
- Hotel Wedding Venues Hotels in Cudjoe Key
- All Inclusive Resorts and in Key West
- Key West Hotels
- Beach Hotel Hotels in Cutthroat Harbor Estates
- Kimpton Hotels in Lower Florida Keys
- Old Florida Style
- Ed & Ellen's Lodging Big Pine Key
- Summerland Key Hotels
- Adults Only Resorts & in Eden Pines
- Barnacle Resort
- Deer Run Bed & Breakfast
- Beautiful Family
- Big Pine Key Hotels
- Save BIG $$ JUNE/JULY! OCEANFRONT 4 BIKES & 2
- Resorts in Cudjoe Key
- Beachfront 3B/3B Fishing Oasis
- Resorts in Big Pine Key
- Apartments in Sugarloaf Key
- Palm COTTAGE
- Villa Jekjak
- Cheap Hotels in Big Pine Key
- Tree Top Paradise
- Villas in Summerland Key
- Cheap Hotels in Key West
- Beach Hotel Hotels in Key West
- Flights to Key West
- Flights from Ramrod Key
- Flights from Miami (MIA) to Key West (EYW)
- Flights from Melody Key
- Flights to Big Pine Key
- Flights from Montreal (YUL) to Key West (EYW)
- Flights from Orlando (MCO) to Key West (EYW)
- Flights from Detroit (DTW) to Key West (EYW)
- Flights to Summerland Key
- Flights from Fort Lauderdale (FLL) to Key West (EYW)
- Flights from Key West Intl.
- Flights from Summerland Key
- Flights from Toronto (YYZ) to Key West (EYW)
- Flights to Melody Key
- Flights from Ottawa (YOW) to Key West (EYW)
- Flights from Buffalo (BUF) to Key West (EYW)
- All inclusive Vacation Packages Lower Florida Keys
- Beach Vacation Packages Cudjoe Key
- Clarence S. Higgs Memorial Beach Park
- Curry Hammock State Park
- Mel Fisher Maritime Museum
- Crane Point Museum and Nature Center
- Fort Zachary Taylor Historic State Park
- Key West Vacations
- South Beach
- Florida Keys Eco - Discovery Center
- Key West Lighthouse and Keeper's Quarters Museum
- Visit Big Torch Key
- Seven Mile Bridge
- Fort East Martello Museum and Gallery
- Marathon Vacations
- Calusa Beach
- Visit Summerland Key
- Visit Little Torch Key
- Everglades National Park
- Anne's Beach
- Key West Shipwreck Museum
- Mallory Square
- Smathers Beach
- Sunset Park Beach
- Veterans Memorial Park & Beach
- All inclusive Vacation Packages Key West
- Visit Big Pine Key
- Harry S. Truman Little White House
- All inclusive Vacation Packages Sugarloaf Key
- Visit Sugarloaf Key
- Visit Cudjoe Key
- Islamorada Vacations
- History of Diving Museum
- Boca Chica Nude Beach
- Visit Ramrod Key
- Sombrero Beach
- Southernmost Point
- Duval Street
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
