Sugarloaf Key Vacation Packages 2026 from $358

Sugarloaf Key flight + hotel vacation packages

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

Creekside Inn

$358

per person

Jan 30 - Feb 4

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

This smoke-free motel's marina and 2 outdoor pools are some of the highlights. Guests will appreciate free perks like free self parking and WiFi in public areas. A picnic area and barbecue grills are also provided.

Henrosa Hotel

South Beach

$582

per person

Jan 24 - Jan 30

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

This hotel features free WiFi in public areas, concierge services, and valet parking. A terrace, a garden, and luggage storage are also on offer.

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

$9,425

per person

Jan 18 - Jan 23

found 1 day ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Miami (MIA)

This aparthotel 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.

501 First Studio Balcony by Palermo Home

Downtown Miami

$780

per person

Jan 16 - Jan 21

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

An outdoor pool is featured at this apartment, along with valet parking. WiFi in public areas is free. Staff at the 24-hour front desk can provide around-the-clock assistance.

Eurostars Winter Haven

South Beach

Save 100% on your flight

$746

per person

Feb 3 - Feb 7

found 21 hours ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

This hotel features a restaurant, a rooftop terrace, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and valet parking. A coffee shop, a terrace, and luggage storage are also on offer.

Top Sugarloaf Key hotels deals

Sugarloaf Key Hotel at KOA Resort

251 Co Rd 939 Summerland Key FL

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The private beach and marina are among the highlights at this hotel. Enjoy the outdoor pool and perks like free self parking and free WiFi. You'll appreciate the hot tub, bar/lounge, and snack bar/deli.

On private beach

Pool

Sugarloaf Key RV Resort & Cottages

311 Johnson Rd Summerland Key FL

Get rates

An outdoor pool, free self parking, and laundry facilities are featured at this vacation home. WiFi in public areas is free. Luggage storage is also provided.

Pool

Pet friendly

Margaritaville Beach House Key West

2001 South Roosevelt Blvd Key West FL

$285 nightly

$321 total

Nov 18 - Nov 19

Total with taxes and fees

This hotel features a restaurant, an outdoor pool, and a bar/lounge. Enjoy the 24-hour gym and perks like a free airport shuttle. You'll appreciate the hot tub, poolside bar, and concierge services.

Pool

Hot Tub

Havana Cabana at Key West

3420 N. Roosevelt Blvd Key West FL

Free Cancellation

Reserve now, pay when you stay

$172 nightly

$194 total

Nov 30 - Dec 1

Total with taxes and fees

This hotel features a restaurant, an outdoor pool, and a bar/lounge. Business travelers can take advantage of the free WiFi in public areas. Enjoy the hot tub and perks like free self parking.

Pool

Hot Tub

Blue Flamingo Resort Key West

3820 North Roosevelt Boulevard Key West FL

Free Cancellation

Reserve now, pay when you stay

$175 nightly

$197 total

Nov 16 - Nov 17

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 a playground, and families will appreciate the picnic area. 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

Beachside Resort & Residences

3841 N Roosevelt Blvd Key West FL

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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

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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.

Frequently asked questions

How much are vacation packages to Sugarloaf Key?

Travelocity offers flight and hotel packages from just $358. 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.