Sugarloaf Key Vacation Packages 2026 from $553

Sugarloaf Key flight + hotel vacation packages

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

Family Pool Home by Hollywood Beach

Hollywood Hills

$553

per person

Jul 16 - Jul 19

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Miami (MIA)

An outdoor pool, free self parking, and laundry facilities are featured at this vacation home. WiFi in public areas is free. Barbecue grills and a virtual front desk are also provided.

The W - Bayshore Unit 1003

East Fort Lauderdale

$562

per person

Jul 2 - Jul 6

found 24 hours ago

Roundtrip flight included

Atlanta (ATL) to Miami (MIA)

This apartment features dry cleaning, laundry facilities, and valet parking. Staff at the 24-hour front desk can provide around-the-clock assistance.

3BR Pool House Sleeps 8

Driftwood

$607

per person

Jun 24 - Jun 28

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Miami (MIA)

An outdoor pool, free self parking, and barbecue grills are featured at this vacation home. WiFi in public areas is free. A garden is also provided.

Brickell Bay 3304

Brickell

$596

per person

Jul 8 - Jul 12

just found

Roundtrip flight included

New York (NYC) to Miami (MIA)

This apartment features dry cleaning, laundry facilities, and free self parking. Staff at the 24-hour front desk can provide around-the-clock assistance.

Cavalier Hotel South Beach

South Beach

$634

per person

Jul 17 - Jul 20

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Miami (MIA)

A restaurant and a bar/lounge are featured at this hotel. WiFi in public areas is free. Valet parking, a terrace, and express check-out are also offered.

Top Sugarloaf Key hotels deals

Sugarloaf Key Hotel at KOA Resort

251 Co Rd 939 Summerland Key FL

Get rates

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

Blue Flamingo Resort Key West

3820 North Roosevelt Boulevard Key West FL

Free Cancellation

Reserve now, pay when you stay

$195 nightly

$219 total

May 31 - Jun 1

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

Hot Tub

Margaritaville Beach House Key West

2001 South Roosevelt Boulevard Key West FL

Free Cancellation

Reserve now, pay when you stay

$261 nightly

$294 total

May 27 - May 28

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

Casa Marina Key West, Curio Collection by Hilton

1500 Reynolds Street Key West FL

Free Cancellation

Reserve now, pay when you stay

$363 nightly

$409 total

May 10 - May 11

Total with taxes and fees

A private beach, a full-service spa, and 2 outdoor pools are all featured at this smoke-free resort. Relax with sun loungers and beach umbrellas, and cool off with a drink at the beachside bar. Enjoy the gym and perks like free WiFi.

On private beach

Pool

Southernmost Beach Resort and Guesthouses

1319 Duval Street Key West FL

Free Cancellation

$312 nightly

$352 total

May 25 - May 26

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 on business? Take advantage of the 2 conference rooms, along with dry cleaning/laundry services.

Pool

Spa

Hilton Garden Inn Key West / The Keys Collection

3850 N Roosevelt Blvd Key West FL

Free Cancellation

Reserve now, pay when you stay

$177 nightly

$199 total

May 10 - May 11

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.

Pool

Hot Tub

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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

Sugarloaf Beach

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

Upper Sugarloaf Key

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

Upper Sugarloaf Sound

Commune with nature and explore the great outdoors at Upper Sugarloaf Sound 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 $553. 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.