Sugarloaf Key Vacations from $467

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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.
The W - Bayshore Unit 1003

The W - Bayshore Unit 1003

3 out of 5
East Fort Lauderdale
Price was $1,199, price is now $467 per person
$467
per person
Jul 14 - Jul 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
7.4/10 Good! (3 reviews)
I thoroughly enjoyed my stay at this hotel. The host was incredibly friendly and attentive, and the communication was prompt and efficient. The hotel itself was beautiful, and the staff was incredibly kind and helpful.

Reviewed on May 20, 2026

Casablanca Miami Beach

Casablanca Miami Beach

3 out of 5
North Beach
Price was $5,507, price is now $2,319 per person
$2,319
per person
Aug 21 - Aug 25
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) 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

MirabileCondoDwntown MIA Brickell w PRKG

MirabileCondoDwntown MIA Brickell w PRKG

5 out of 5
Downtown Miami
Save 100% on your flight
Price was $1,058, price is now $487 per person
$487
per person
Jul 24 - Jul 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
2/10 (2 reviews)
Brickell Bay 3318

Brickell Bay 3318

3 out of 5
Brickell
Price was $1,140, price is now $532 per person
$532
per person
Jul 10 - Jul 13
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
No reviews
Brickell Bay 3505

Brickell Bay 3505

3 out of 5
Brickell
Price was $1,921, price is now $900 per person
$900
per person
Jul 17 - Jul 24
found 17 hours ago
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
9.4/10 Exceptional! (3 reviews)
Great place and location! The pool was amazing.

Reviewed on May 9, 2026

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Discover the most popular places to visit in Sugarloaf Key

Sugarloaf Beach

Sugarloaf Beach

Why not spend a lazy afternoon at Sugarloaf Beach during your trip to Summerland Key?

Sugarloaf Beach

Upper Sugarloaf Key

Commune with nature and explore the great outdoors at Upper Sugarloaf Key during your travels in Summerland Key.

Upper Sugarloaf Key

Upper Sugarloaf Sound

Commune with nature and explore the great outdoors at Upper Sugarloaf Sound during your travels in Summerland Key.

Upper Sugarloaf Sound

What to do in Sugarloaf Key

Marathon Backcountry Permit

Marathon Backcountry Fishing Charter

$667
per traveler
Marathon Backcountry Fishing Charter
Golden Glare Fishing Charter with Experienced Captain

Golden Glare Fishing Charter with Experienced Captain

$650
per traveler
Golden Glare Fishing Charter with Experienced Captain
Private Luxury Sandbar Excursion

Private Luxury Sandbar Excursion

$1,200
per traveler
Private Luxury Sandbar Excursion
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
9.8/10 Exceptional! (577 reviews)
"This KOA was an amazing place to stay with plenty to do and close to great things to do in the Keys. Close to Key West, Big Pine Key and Marathon! Beautiful facilities and kids loved the play/swim area."

Reviewed on Jun 5, 2026

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Sugarloaf Key Hotel at KOA Resort
Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

4 out of 5
3820 North Roosevelt Boulevard Key West FL
Fully refundableReserve now, pay when you stay
$179 nightly
The price is $201 total per night from Jul 6 to Jul 7
$201 total
Jul 6 - Jul 7
Total with taxes and fees
8.4/10 Very Good! (2,331 reviews)
"The resort staff were very nice and accommodating the only issue we had was with the bartender"

Reviewed on Jun 5, 2026

Blue Flamingo Resort Key West
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
1319 Duval Street Key West FL
Fully refundableReserve now, pay when you stay
$261 nightly
The price is $294 total per night from Jun 29 to Jun 30
$294 total
Jun 29 - Jun 30
Total with taxes and fees
8.8/10 Excellent! (3,362 reviews)
"Look, we had a nice time. I put "OK" for your survey questions which may seem like we didn't enjoy. But, it would be hard to put "Good" for your survey answers. The beach was unusable due to dead, smelly seaweed that permeated the main pool, overall exterior (stairs, pool area, etc.) rooster poop, ..."

Reviewed on Jun 5, 2026

Southernmost Beach Resort and Guesthouses
See all 3,452 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 $467 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.