
Sugarloaf Key Vacations from $465
Book a 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
Your Sugarloaf Key Vacation
From its highlights to its hidden gems, this city is best explored with a Sugarloaf Key vacation package. Check out hotels located in Sugarloaf Shores, which is good for families, fishing and views. Make your trip to Sugarloaf Key even more exciting by including some sightseeing. Florida Keys Beaches, Sugarloaf Beach and Upper Sugarloaf Sound are among the major attractions you'll want to explore. No matter your travel plans or budget, putting together the ultimate tailored Sugarloaf Key vacation is simple with Expedia.
The Latest Sugarloaf Key vacation packages
Price found within the past 48 hours. Click for updated prices.

Bay Breeze Premium Apartments By Eskape Collection
Save 100% on your flight
Price was $908, price is now $465 per person
$465
per person
Sep 10 - Sep 17
found 23 hours ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.8/10 Excellent! (223 reviews)
The host is very friendly and settings of the apartment is comfortable and cozy. Only minor thing is parking slot narrow.
Reviewed on Jun 29, 2026

Nobu Hotel Miami Beach
Mid Beach
Price was $1,282, price is now $593 per person
$593
per person
Sep 5 - Sep 10
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.6/10 Excellent! (1,418 reviews)
I was really shocked when I came to this hotel. I was expecting 5-star luxury for my weekend in Miami, but it was not that. The building is very old and needs renovating. Walls peeling, furniture chipped just very run down. The front desk was old looking, not to mention we had to wait a few minutes for someone to show up to check us in. The pool area was nice and the beds in the rooms were very comfortable. However the pool staff were not really attentive at all. We had to walk around and find them to place orders. Pretty disappointed in the hotel and will not be staying again or recommending if someone is looking for a 5-star luxury hotel in Miami.
Reviewed on Jun 27, 2026


Eden Roc Miami Beach
Mid Beach
Save 100% on your flight
Price was $1,058, price is now $536 per person
$536
per person
Sep 5 - Sep 10
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.6/10 Excellent! (3,293 reviews)
We loved staying at the Eden Roc! The room and the view was amazing! The staff was so friendly and accommodating! My only complaint is that the refrigerator was full of drinks you could purchase, but I rather have an empty refrigerator so I could store left overs or my own drinks. Also I wish we had a microwave. I rate this a 9/10. Special shout out to Joel with the conseirge desk! He was so amazing and super helpful! We would love to come back and stay!
Reviewed on Jun 29, 2026

Casablanca Miami Beach
North Beach
Price was $1,722, price is now $889 per person
$889
per person
Sep 4 - Sep 8
found 1 day ago
Roundtrip flight included
New York (JFK) 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
Don't see what you're looking for?
See all available trips from Columbus to Sugarloaf Key
View all tripsWhat to do in Sugarloaf Key

Luxury Sandbar and Snorkeling trip in Key West
$1,200
per traveler
Sugarloaf Key Hotel Deals

Sugarloaf Key Hotel at KOA Resort
251 Co Rd 939 Summerland Key FL
9.8/10 Exceptional! (591 reviews)
"I’ve got to say the room was the cleanest I’ve ever seen. When I can take off my shoes and walk barefooted and my feet stay clean I’m happy. The staff was marvelous, esp the bartenders. The ones that did Bingo and Kareokee were a lot of fun. I also ran into an older worker who was so very nice. The ..."
Reviewed on Jun 27, 2026

Beachside Resort & Residences
3841 N Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
$202 nightly
The price is $227 total per night from Jul 1 to Jul 2
$227 total
Jul 1 - Jul 2
Total with taxes and fees
8.6/10 Excellent! (2,316 reviews)
"The hotel overall looked like it needs an overhaul. None of the elevators were working.. it was past 4 pm and our room still wasn’t ready! The check in person really tried to assist.. but luckily it was only one night .."
Reviewed on Jun 29, 2026

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 Jul 1 to Jul 2
$197 total
Jul 1 - Jul 2
Total with taxes and fees
8.4/10 Very Good! (2,470 reviews)
"Excellent room with a gorgeous view! Three adults staying in a two bed room can feel tight but that was no issue at Blue Flamingo. They have truly covered all of the details. You will have an amazing visit!!!"
Reviewed on Jun 30, 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 Sugarloaf Key Vacation Packages
Sugarloaf Key Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Key West Intl. Airport (EYW) |
Max Temp Winter | 75ºF |
Max Temp Summer | 85ºF |
Top Sights | Florida Keys Beaches, Boca Chica Nude Beach and Sugarloaf Beach |
More vacations you might like
Frequently asked questions
Explore a world of travel with Expedia
- Summerland Key Hotels
- Oceanfront Hotels in Marathon
- Key West Hotels
- Key West Historic District Hotels
- Family Hotels in Key West
- Resorts in Key West
- Hotels near Duval Street
- All-Inclusive Resorts in Key West
- Oceanfront Hotels in Key West
- Beach Hotels in Key West
- Cheap Hotels in Key West
- Houseboats in Key West
- Adults Only Resorts & in Key West
- Flights from Columbus (CMH) to Key West (EYW)
- Flights to Marathon
- Flights from Cleveland (CLE) to Key West (EYW)
- Flights from St. Louis (STL) to Key West (EYW)
- Flights from Newark Liberty Intl. Airport (EWR) to Key West (EYW)
- Flights from Denver (DEN) to Key West (EYW)
- Flights from Chicago (ORD) to Key West (EYW)
- Flights from Fort Myers (RSW) to Key West (EYW)
- Flights from Detroit (DTW) to Key West (EYW)
- Flights from New York (JFK) to Key West (EYW)
- Flights from Houston (IAH) to Key West (EYW)
- Flights from Atlanta (ATL) to Key West (EYW)
- Flights from Baltimore (BWI) to Key West (EYW)
- Flights from Tampa (TPA) to Key West (EYW)
- Flights from Hartford (BDL) to Key West (EYW)
- Flights from Charlotte (CLT) to Key West (EYW)
- Flights from Dallas (DFW) to Key West (EYW)
- Flights from Orlando (MCO) to Key West (EYW)
- Flights from Raleigh (RDU) to Key West (EYW)
- Flights to Key West
- Flights from West Palm Beach (PBI) to Key West (EYW)
- Flights from Philadelphia (PHL) to Key West (EYW)
- Flights from Pittsburgh (PIT) to Key West (EYW)
- Flights from Indianapolis (IND) to Key West (EYW)
- Flights from Nashville (BNA) to Key West (EYW)
- Flights from Sarasota (SRQ) to Key West (EYW)
- Flights from Fort Lauderdale (FLL) to Key West (EYW)
- Flights from Jacksonville (JAX) to Key West (EYW)
- Flights from Miami (MIA) to Key West (EYW)
- Flights from Washington (DCA) to Key West (EYW)
- Flights from Key West Intl.
- Flights from Minneapolis (MSP) to Key West (EYW)
- Flights from Boston (BOS) to Key West (EYW)
- Flights from Florida Keys Marathon
- Visit Sugarloaf Key
- Ernest Hemingway Home and Museum
- Key West Butterfly and Nature Conservatory
- Museum of Art & History at the Custom House
- Mallory Dock
- Key West Vacations
- Key West Tropical Forest and Botanical Garden
- Fort Zachary Taylor Historic State Park
- Key West Firehouse Museum
- Clarence S. Higgs Memorial Beach Park
- Stock Island Yacht Club & Marina
- Key West Shipwreck Museum
- Jackson Square
- San Carlos Institute - Casa Cuba
- Bahama Village Vacations
- Tennessee Williams Key West Exhibit
- Visit Downtown Key West
- Waterfront Playhouse
- Schooner Western Union
- The Kite House
- Old Town Key West Vacations
- All inclusive Vacation Packages Key West
- Sombrero Beach
- Sails To Rails Museum at Flagler Station
- Looe Key National Marine Sanctuary
- Cook Island
- Key West Historic District Vacations
- Summerland Key Vacations
- Visit Big Pine Key
- Duval Street
- Fort East Martello Museum and Gallery
- Seven Mile Bridge
- Boca Chica Nude Beach
- Upper Sugarloaf Sound
- Robbie's
- Mallory Square
- Key West National Wildlife Refuge
- Big Pine Key Flea Market
- Smathers Beach
- Key West Burlesque Theater
- Southernmost Point
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.





















