
Sugarloaf Key Vacations from $445
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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.


Avi Lux Stay
East Fort Lauderdale
Price was $2,216, price is now $978 per person
$978
per person
Dec 5 - Dec 12
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
7.6/10 Good! (10 reviews)
If you are looking for a quiet place to stay this suite is NOT recommended. You can hear motorcycles and racing cars at all hours of the night. Valet is $60 per night mandatory payment required upon check in for the entire length of your stay tips not included. This is not stated in the description prior to booking. BEWARE.
Reviewed on Aug 28, 2025

The Retreat Collection at 1 Hotel & Homes South Beach
South Beach
Price was $21,549, price is now $10,089 per person
$10,089
per person
Jan 28 - Feb 2
found 8 hours 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


72 Park Miami Beach Boutique Residences by IliosRentals
North Beach
Price was $2,289, price is now $1,141 per person
$1,141
per person
Jan 28 - Feb 2
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.4/10 Very Good! (18 reviews)
We had a wonderful stay with our group of three adults and three children! Everything was very comfortable, and the apartment was beautiful, clean, and well-maintained. There is a convenient shuttle service to the beach, but the 10-minute walk is also perfectly fine, even with children. Communication was excellent, and any questions we had were answered quickly. Overall, a very pleasant experience for the whole family. We would definitely recommend this place and would happily stay here again!
Reviewed on Oct 17, 2026
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View all tripsWhat to do in Sugarloaf Key

Private Luxury Sandbar Excursion in Key West
$1,200
per traveler

Private Marathon Backcountry Fishing Charter
$750
per adult

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

Sugarloaf Key RV Resort & Cottages
311 Johnson Rd Summerland Key FL
9.2/10 Wonderful! (41 reviews)
"Clean and quiet bungalow that is convenient to Key West but far enough away to enjoy the quiet."
Reviewed on Nov 4, 2026

Margaritaville Beach House Key West
2001 South Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
$285 nightly
The price is $321 total per night from Nov 18 to Nov 19
$321 total
Nov 18 - Nov 19
Total with taxes and fees
8.8/10 Excellent! (1,814 reviews)
"Nice property"
Reviewed on Nov 4, 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 |
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Frequently asked questions
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- JetBlue Airways Boston (BOS) to Key West (EYW) flights
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- Flights from Orlando (MCO) to Key West (EYW)
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