Sugarloaf Key Vacation Packages 2025/2026 from $283

Sugarloaf Key flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.

Broadmore Miami Beach

North Beach

Save 100% on your flight

$283

per person

Jan 21 - Jan 25

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

This hotel features a restaurant, an outdoor pool, and a bar/lounge. A coffee shop, a terrace, and luggage storage are also on offer.

Hawks Cay Resort

$1,099

per person

Jan 17 - Jan 24

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

This luxury hotel features a private beach, a full-service spa, and a marina. Spend a day at the beach snorkeling, or relax with sun loungers and beach umbrellas. There's fun for all ages with a children's club and a children's pool, and families will appreciate the picnic area.

The Shelborne By Proper, a Member of Design Hotels

South Beach

$878

per person

Jan 22 - Jan 26

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

A private beach, a 24-hour gym, and a restaurant are all featured at this boutique hotel. Relax with free beach cabanas and sun loungers, and cool off with a drink at the beachside bar. Relax with a drink at one of the 3 bars/lounges and get perks like free WiFi.

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

$7,502

per person

Jan 26 - Jan 30

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

This condo resort features 2 restaurants, 3 outdoor pools, and a gym. There's fun for all ages with a children's club and a children's pool, and babysitting is an added bonus. Enjoy the a rooftop terrace and perks like free WiFi.

President Villa

South Beach

$644

per person

Jan 14 - Jan 20

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

This hotel features a restaurant, an outdoor pool, and a bar/lounge. Guests will appreciate free perks like full breakfast and WiFi in public areas. Valet parking, a terrace, and luggage storage are also offered.

Top Sugarloaf Key hotels deals

Beachside Resort & Residences

3841 N Roosevelt Blvd, Key West, FL

Free Cancellation

Reserve now, pay when you stay

$193 nightly

$217 total

Nov 20 - Nov 21

Total with taxes and fees

This smoke-free hotel features a private beach, a marina, and 2 restaurants. Enjoy a day at the beach kayaking, or relax with sun loungers. Unwind with a drink at one of the 2 bars/lounges and enjoy freebies like WiFi in public areas and an area shuttle.

On private beach

Pool

Blue Flamingo Resort Key West

3820 North Roosevelt Boulevard, Key West, FL

Free Cancellation

Reserve now, pay when you stay

$148 nightly

$167 total

Nov 17 - Nov 18

Total with taxes and fees

This hotel features 2 restaurants, 2 outdoor pools, and a 24-hour gym. There's fun for all ages with mini golf and an arcade/game room, and families will appreciate the onsite laundry facilities. Unwind with a drink at one of the 2 poolside bars and enjoy freebies like WiFi in public areas and an area shuttle.

Pool

Hot Tub

Oceans Edge Key West Resort, Hotel & Marina

5950 Peninsular Avenue, Key West, FL

Free Cancellation

Reserve now, pay when you stay

$208 nightly

$234 total

Nov 30 - Dec 1

Total with taxes and fees

A marina, 6 outdoor pools, and a 24-hour gym are all featured at this smoke-free hotel. Business travelers can take advantage of the free WiFi in public areas. The restaurant provides options for dining, while the bar/lounge and poolside bar are great spots to unwind.

Pool

Pet friendly

Southernmost Beach Resort and Guesthouses

1319 Duval Street, Key West, FL

Free Cancellation

$242 nightly

$272 total

Nov 30 - Dec 1

Total with taxes and fees

This hotel features a full-service spa, 3 outdoor pools, and a restaurant. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. Traveling for business? Take advantage of the 24-hour business center, laundry service, and conference space.

Margaritaville Beach House Key West

2001 South Roosevelt Boulevard, Key West, FL

Free Cancellation

Reserve now, pay when you stay

$235 nightly

$264 total

Dec 2 - Dec 3

Total with taxes and fees

This hotel features a restaurant, an outdoor pool, and a bar/lounge. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including food and water bowls. There's a 24-hour gym on site, and a 24-hour front desk and dry cleaning are also provided.

Pool

Pet friendly

Hilton Garden Inn Key West / The Keys Collection

3850 N Roosevelt Blvd, Key West, FL

Free Cancellation

Reserve now, pay when you stay

$112 nightly

$126 total

Dec 1 - Dec 2

Total with taxes and fees

This smoke-free hotel includes 2 restaurants, an outdoor pool, and a hot tub. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the gym and perks like a free area shuttle.

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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.

Popular places to visit

Upper Sugarloaf Sound

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

Upper Sugarloaf Key

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

Sugarloaf Beach

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

Frequently asked questions

How much are vacation packages to Sugarloaf Key?

Travelocity offers flight and hotel packages from just $283. With such amazing deals, you'll be saying hello to Sugarloaf Key before too long.

How long should my Sugarloaf Key vacation be?

Many travelers like to spend roughly 2 nights in Sugarloaf Key. But that's not set in stone. Whether you opt to stay for a matter of days or weeks, you'll enjoy discovering all the fantastic things that this place has to offer.

Where can I get the best vacation package deals for Sugarloaf Key?

There are incredible Sugarloaf Key package deals to snap up with Travelocity. Did you know we partner with as many as 400 airlines and 1,000,000 properties worldwide? Remember this when you're ready to cross another destination off the old bucket list.

Why should I purchase my Sugarloaf Key vacation bundle via Travelocity?

From enchanting destinations to memorable experiences, we have everything you need to satisfy your wanderlust. Our 24/7 support will also make sure you're taken care of during your trip. And don't panic if you notice a lower price on your booking, we'll match it. That's our Price Match Guarantee.

Can I save on my Sugarloaf Key car rental if I bundle it with hotels and flights?

Combining your flight, hotel and car into a Sugarloaf Key vacation package is the best way to score an amazing deal. Plus, having your own set of wheels gives you the freedom to find your way to all those famous sights you want to check out. Sitting 120 mi away from Sugarloaf Key, PortMiami is one attraction that should have a place on your itinerary. Top up the tank and make a day trip of it.

What is the best time of year to go to Sugarloaf Key?

Going in the low season, April, September and October, has its upsides — think more affordable airfares and hotels and less bumping elbows with hordes of tourists. But there's magic in the air in the busiest season. More events will be staged and more attractions will be open in February, March and November. If you want to stretch your budget, has the thriftiest hotel rates. Expect to pay more for a bed in .

Which airport is best for Sugarloaf Key?

Key West Intl. Airport (EYW) is roughly 14 mi west of central Sugarloaf Key.

What is there to do in Sugarloaf Key?

While venturing off the beaten track is rewarding, you shouldn't ignore the well-known sights that make a place famous. Sugarloaf Beach and Upper Sugarloaf Sound are just two of them in Sugarloaf Key.

Where should I stay when visiting Sugarloaf Key?

If you're looking for a place to spend your nights, have a look at the Sugar Loaf Lodge. It's the top choice for many visitors.