
Sugarloaf Key Vacations from $344
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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.

Private Apartment at the Congress
South Beach
Save 100% on your flight
Price was $592, price is now $344 per person
$344
per person
Aug 26 - Aug 29
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
5.6/10 (11 reviews)
Really friendly staff, easy check in and even accommodated early check in. Roof top pool was clean and spacious with a nice bar.
Reviewed on Jul 9, 2026

Casablanca Miami Beach
North Beach
Price was $9,488, price is now $4,203 per person
$4,203
per person
Oct 8 - Oct 12
found 12 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Miami (MIA)
5.8/10 (326 reviews)
Pleas don’t book the apartment in this hotel. It’s not associated with the hotel services. The 2nd room has 3 beds all bed sheets were dirty. The has prior hair from guest before us. Behind the headboard I found a dirty t-shirt. Hall restroom tub was rusted and peeling, I was disgusted to see that. The other restroom still had a long hair in the tub. Sanitary is NOT a priority for the owner of this apartment. The price I paid for my 4 day was a steel. Also, beach gear was a laugh in the face. No beach chair, no wagon and the umbrella covered 1 person. I reached out to the person but never showed up with clean sheets. I had to invest in my stay detergent, sanitizing wipes, trash bags and toilet covers. Let me know forget to say, on my first stay the bottom of my feet was all black from the floors being super dirty. The only good thing of the place was the beach distance.
Reviewed on Jul 23, 2026

The Retreat Collection at 1 Hotel & Homes South Beach
South Beach
Price was $13,429, price is now $7,191 per person
$7,191
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip flight included
Boston (BOS) 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

President Hotel Villa
South Beach
Price was $843, price is now $469 per person
$469
per person
Oct 3 - Oct 10
found 9 hours ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.2/10 Very Good! (1,010 reviews)
I love this hotel. Great location, super cute decorative lobby and good breakfast options. Staff was also very nice and professional . My room was so clean and it was huge . I loved everything about it. The only thing was the power went out in the entire hotel for about 2-3 hours. That was very scary because there was a dad and his young daughter that almost got stuck in the elevator just as it happened . He had to pry to door open to get them out. I was worried because I also had a small child with me and i didn’t want our room to start getting hot since the ac went off and I wasn’t able to charge my phone . That’s the only issue I had . I do understand that it’s an old boutique hotel (that has been renovated externally ) so the internal wiring may be older than some of the newer hotels and the ac is fighting against that dense Miami heat. However there should be major upgrades to the wiring and there should also be backup generators for emergency situations like that. I would love to stay here again but I am nervous that it may happen again.
Reviewed on Jul 23, 2026

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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 RV Resort & Cottages
311 Johnson Rd Summerland Key FL
9.4/10 Exceptional! (21 reviews)
"Great location with short drive to Key Eest. Nice salt water lake to fish in. Comfortable accommodations."
Reviewed on Jul 22, 2026

Sugarloaf Key Hotel at KOA Resort
251 Co Rd 939 Summerland Key FL

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 Aug 17 to Aug 18
$227 total
Aug 17 - Aug 18
Total with taxes and fees
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 |
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- 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
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