
Sugarloaf Key Vacations from $365
Book a Hotel + Flight or Car together to unlock savings
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.

Creekside Inn
Price was $757, price is now $365 per person
$365
per person
Feb 6 - Feb 11
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
7.8/10 Good! (1,025 reviews)
The staff was friendly and welcoming and the restaurants were very close. On the 2nd day I needed a fresh set of towels and they delivered them quickly.
I will stay there again if I'm in Tavanier.
Reviewed on Nov 13, 2026


The Retreat Collection at 1 Hotel & Homes South Beach
South Beach
Price was $42,134, price is now $20,902 per person
$20,902
per person
Dec 30 - Jan 5
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


Avi Lux Stay
East Fort Lauderdale
Price was $1,407, price is now $736 per person
$736
per person
Jan 27 - Jan 31
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
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See all available trips from Columbus to Sugarloaf Key
View all tripsWhat to do in Sugarloaf Key

Private Marathon Backcountry Fishing Charter
$750
per adult

Guided Night Kayak Adventure Tour in Luminous Lagoon
$90
per adult
80% of travellers recommend
Sugarloaf Key Hotel Deals

Sugarloaf Key Hotel at KOA Resort
251 Co Rd 939 Summerland Key FL
9.8/10 Exceptional! (671 reviews)
"The property is meticulous. The rooms are spotless, and beautifully decorated. The balcony is very big and the views of the water are amazing. The pool and bar area are wonderful and the outside bar staff was excellent. Would recommend 10/10."
Reviewed on Nov 13, 2026

Sugarloaf Key RV Resort & Cottages
311 Johnson Rd Summerland Key FL
9.2/10 Wonderful! (44 reviews)
"Clean and new"
Reviewed on Nov 11, 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! (1,817 reviews)
"Muy bien hospedaje"
Reviewed on Nov 13, 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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- Visit Sugarloaf Key
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- Visit Florida Keys
- Upper Sugarloaf Sound
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- Visit Summerland Key
- Fort East Martello Museum and Gallery
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- Visit Ramrod Key
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- Florida Keys All Inclusive Vacation Packages
- Visit Cudjoe Key
- Big Pine Key Vacations
- Where to stay in Lower Florida Keys
- Visit Little Torch Key
- Smathers Beach
- Where to stay in Sugarloaf Key
- Clarence S. Higgs Memorial Beach Park
- Old Town Key West Vacations
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- Visit Lower Florida Keys
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- Visit Big Pine Key
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- Visit Boca Chica Key
- Where to stay in Marathon
- Lower Florida Keys All Inclusive Vacation Packages
- Visit New Town
- Where to stay in Boca Chica Key
- Florida Keys All Inclusive Vacation Packages
- Visit Downtown Key West
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.



















