Sugarloaf Key Vacations from $732

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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.
Glam Miami Nightlife - Resort Pool - Downtown

Glam Miami Nightlife - Resort Pool - Downtown

4 out of 5
Downtown Miami
Price was $1,409, price is now $732 per person
$732
per person
Jan 13 - Jan 16
found 8 hours ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
10/10 Exceptional! (1 review)
Loved this stay! The place was PERFECT. Could not ask for more!! Will definitely staying here again next time I’m in Miami.

Reviewed on Oct 20, 2026

Avi Lux Stay

Avi Lux Stay

4.5 out of 5
East Fort Lauderdale
Price was $2,168, price is now $778 per person
$778
per person
Dec 5 - Dec 12
found 10 hours 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

The Retreat Collection at 1 Hotel & Homes South Beach

5 out of 5
South Beach
Price was $20,316, price is now $9,557 per person
$9,557
per person
Jan 19 - Jan 24
found 23 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) 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

501 First Studio Balcony by Palermo Home

501 First Studio Balcony by Palermo Home

2 out of 5
Downtown Miami
Price was $1,806, price is now $864 per person
$864
per person
Jan 17 - Jan 23
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
No reviews

501 First - Rooftop Pool - Gym

501 First - Rooftop Pool - Gym

2.5 out of 5
Downtown Miami
Price was $1,641, price is now $847 per person
$847
per person
Jan 17 - Jan 23
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
No reviews

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What to do in Sugarloaf Key

Private Luxury Sandbar Excursion

Private Luxury Sandbar Excursion in Key West

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

Private Marathon Backcountry Fishing Charter

$750
per adult
Private Marathon Backcountry Fishing Charter
Luxury Sandbar and Snorkeling trip in Key West

Luxury Sandbar and Snorkeling trip in Key West

$1,200
per traveler
Luxury Sandbar and Snorkeling trip in Key West
See all activities in Sugarloaf Key

Sugarloaf Key Hotel Deals

Sugarloaf Key Hotel at KOA Resort

Sugarloaf Key Hotel at KOA Resort

3 out of 5
251 Co Rd 939 Summerland Key FL
Get rates
Sugarloaf Key Hotel at KOA Resort
Sugarloaf Key RV Resort & Cottages

Sugarloaf Key RV Resort & Cottages

3 out of 5
311 Johnson Rd Summerland Key FL
9.2/10 Wonderful! (38 reviews)
"The size of the bungalow was perfect. Being on the lake was an added benefit especially with the "historic" king tides."

Reviewed on Oct 30, 2026

Get rates
Sugarloaf Key RV Resort & Cottages
Margaritaville Beach House Key West

Margaritaville Beach House Key West

4 out of 5
2001 South Roosevelt Blvd Key West FL
$285 nightly
The price is $321 total per night from Nov 15 to Nov 16
$321 total
Nov 15 - Nov 16
Total with taxes and fees
8.8/10 Excellent! (1,810 reviews)
"I like to stay there. It’s very nice. The property is kept up very clean. Maybe get a little bit bigger trash cans for us"

Reviewed on Nov 1, 2026

Margaritaville Beach House Key West
See all 3,446 properties in Sugarloaf Key
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

How much does a Sugarloaf Key vacation package cost?
Offering excellent value package deals from $732 on Expedia, you'll be thrilled with how little a vacation to Sugarloaf Key costs! Our packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Sugarloaf Key?
April, September and October are great times to search for cheap Sugarloaf Key vacation packages. Choosing to travel in less busy periods means you can generally find lower prices on flights and accommodations.
How many days is enough for Sugarloaf Key?
For your Sugarloaf Key vacation, a few days will be enough to explore all the highlights. Be sure to visit Upper Sugarloaf Sound — it's one of the major sights in this destination. If you're looking for more activities, think about basing yourself here and venturing off on some day tours from Sugarloaf Key.
Is it worth booking a vacation package to Sugarloaf Key?
Sugarloaf Key has everything you need for a fantastic break — hiking, walking trails and nature are just the start. Whether you want to check out sights like Florida Keys Beaches and Sugarloaf Beach, or take the path less traveled, there's plenty to do on your Sugarloaf Key vacation.
How to find the best Sugarloaf Key package deals?
Start your search for a Sugarloaf Key package deal by entering your destination and preferred trip dates under our "Packages" tab. Then add a few filters, like "Popular locations" and "Amenities," to fine-tune the results to your exact style. You can also sort by "Package discount" and browse offers that come with big savings. If you don't find the ideal Sugarloaf Key package deal right away, just change your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Sugarloaf Key adventure off to a flying start.
Is it cheaper to book a Sugarloaf Key vacation as a package?
An Expedia vacation package could land you considerable savings when compared to booking flights and accommodations separately. Better still, you can customize your Sugarloaf Key getaway to match your exact style. Pick your preferred flight time, select the hotel type and add a rental car. Explore our bundles to see how much you can save.
When to book a vacation package to Sugarloaf Key?
If you're considering an impromptu Sugarloaf Key trip, browse our last-minute deals that can be booked up to one week before you take off. Don't want to leave things to the last minute? You can score sensational deals on your hotels and flights by booking ahead.
How to plan a trip to Sugarloaf Key?

  1. Choose when to go: Check your diary and pack your bags. Your favorite time of year and the available activities will also help you decide when to visit Sugarloaf Key.
  2. Calculate your budget: Make sure you have enough money to cover everything from food and transportation to airfares and activities. Your hotel will probably be the largest expense during your trip to Sugarloaf Key.
  3. Use our trip planning tool to explore Sugarloaf Key: Research every part of your trip to Sugarloaf Key with this handy planner. Invite your friends and family to collaborate on a group getaway, search for stays or things to do and make bookings.
  4. Work out your trip length: Consider how long you'd like to spend exploring Sugarloaf Key. Plan your itinerary so you can get to all the activities and attractions you're interested in without rushing.
  5. Bundle your hotel and flights: Awesome destination, check. Length of stay, check. All that's left now is to find a Sugarloaf Key vacation package that brings all your bookings together.
  6. Book experiences or activities in advance: Whether it's a ticket to a major attraction or a walking tour, you won't have to worry about missing out on the highlights of Sugarloaf Key. Find all the incredible things to do in Sugarloaf Key with our dedicated travel guide.

Does Expedia offer Book Now, Pay Later Sugarloaf Key vacation packages?
Your Sugarloaf Key break is meant to be an escape from your daily routine, not a reason for money worries. So to allow you a little more flexibility, we've teamed up with online lender Affirm to offer you our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and break down the cost over 3, 6 or 12 months. Plus, there aren't any late payment fees or hidden costs to worry about.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.