Sugarloaf Key Vacation Packages 2026 from $341

Sugarloaf Key flight + hotel vacation packages

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

Barcelona Studios Guesthouse

South Beach

Save 100% on your flight

$341

per person

Nov 14 - Nov 18

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

Free WiFi in public areas, a garden, and a picnic area are available at this guesthouse. Express check-out and a virtual front desk are also provided.

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

$14,649

per person

Dec 17 - Dec 23

found 1 day ago

Roundtrip flight included

Boston (BOS) 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.

Miami Vacation Rentals - Downtown

Downtown Miami

Save 100% on your flight

$1,087

per person

Dec 5 - Dec 11

found 3 hours ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

This apartment features an outdoor pool and a 24-hour gym. Enjoy the sauna and perks like free WiFi. A poolside bar, a 24-hour front desk, and a terrace are also provided.

The Penguin Hotel

South Beach

Save 100% on your flight

$440

per person

Dec 9 - Dec 13

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

This hotel features a restaurant, an outdoor pool, and a bar/lounge. WiFi in public areas is free. Valet parking, a terrace, and a garden are also offered.

1 Hotel South Beach

South Beach

Save 100% on your flight

$2,037

per person

Dec 11 - Dec 15

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

A full-service spa, 3 restaurants, and 3 outdoor pools are all featured at this smoke-free hotel. Relax with beach cabanas, sun loungers, and beach umbrellas. There's fun for all ages with a children's club and a children's pool, and in-room childcare is an added bonus.

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

Beachside Resort & Residences

3841 N Roosevelt Blvd Key West FL

Free Cancellation

Reserve now, pay when you stay

$185 nightly

$208 total

Oct 4 - Oct 5

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

$168 nightly

$189 total

Oct 4 - Oct 5

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 Blvd Key West FL

Free Cancellation

Reserve now, pay when you stay

$265 nightly

$298 total

Oct 4 - Oct 5

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

$184 nightly

$207 total

Nov 1 - Nov 2

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

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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 $341. 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.