Sugarloaf Key Vacation Packages 2025/2026 from $307

Sugarloaf Key flight + hotel vacation packages

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

The Penguin Hotel

South Beach

Save 100% on your flight

per person

Oct 10 - Oct 13

found 1 day ago

Roundtrip flight included

Baltimore (BWI) to Miami (MIA)

A restaurant and a bar/lounge are featured at this hotel. Valet parking, a terrace, and a garden are also offered.

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

per person

Sep 26 - Sep 30

found 1 day ago

Roundtrip flight included

Baltimore (BWI) 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.

The Shelborne By Proper, a Member of Design Hotels

South Beach

per person

Sep 27 - Oct 3

found 15 hours ago

Roundtrip flight included

Baltimore (BWI) 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.

Cavalier Hotel South Beach

South Beach

Save 100% on your flight

per person

Oct 10 - Oct 13

found 1 day ago

Roundtrip flight included

Baltimore (BWI) to Miami (MIA)

A restaurant and a bar/lounge are featured at this hotel. Valet parking, a terrace, and express check-out are also offered.

iCoconutGrove Vacation Rentals

Coconut Grove

per person

Sep 29 - Oct 4

found 11 hours ago

Roundtrip flight included

Baltimore (BWI) to Miami (MIA)

This hotel features an outdoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. There's a hot tub on site, and laundry facilities and wedding services 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

$194 nightly

$218 total

Aug 3 - Aug 4

Total includes 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

Southernmost Beach Resort and Guesthouses

1319 Duval Street, Key West, FL

Free Cancellation

$259 nightly

$291 total

Aug 4 - Aug 5

Total includes 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.

Pool

Spa

Blue Flamingo Resort Key West

3820 North Roosevelt Boulevard, Key West, FL

Free Cancellation

Reserve now, pay when you stay

$172 nightly

$193 total

Aug 19 - Aug 20

Total includes taxes and fees

This eco-certified 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

Pet friendly

Oceans Edge Key West Resort, Hotel & Marina

5950 Peninsular Avenue, Key West, FL

Free Cancellation

Reserve now, pay when you stay

$215 nightly

$242 total

Aug 10 - Aug 11

Total includes 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

Margaritaville Beach House Key West

2001 South Roosevelt Boulevard, Key West, FL

Free Cancellation

Reserve now, pay when you stay

$235 nightly

$264 total

Aug 10 - Aug 11

Total includes 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

Fairfield Inn and Suites by Marriott Key West

2400 N Roosevelt Blvd, Key West, FL

Free Cancellation

Reserve now, pay when you stay

$143 nightly

$161 total

Aug 17 - Aug 18

Total includes taxes and fees

This hotel features a restaurant, an outdoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the 24-hour gym and free continental breakfast each morning.

Pool

Breakfast included

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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.

Sugarloaf Beach

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

Upper Sugarloaf Key

4/5(21 reviews)

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

Frequently asked questions

How much are vacation packages to Sugarloaf Key?

Travelocity offers flight and hotel packages from just $307. 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.