Upper Sugarloaf Key Vacation Deals: Upper Sugarloaf Key, Summerland Key Vacations

Upper Sugarloaf Key vacation package deals

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

Barcelona Studios Guesthouse

South Beach

Save 100% on your flight

$240

per person

Oct 23 - Oct 26

found 1 day ago

Roundtrip flight included

Atlanta (ATL) 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

$8,235

per person

Dec 4 - Dec 7

found 7 hours ago

Roundtrip flight included

Atlanta (ATL) 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.

Ridley House - Key West Historic Inns

Key West Historic District

Save 100% on your flight

$990

per person

Dec 5 - Dec 9

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Key West (EYW)

An outdoor pool is featured at this hotel, along with free WiFi in public areas and luggage storage. Enjoy the free buffet breakfast each morning. Concierge services are provided for your convenience.

Park Central South Beach

South Beach

Save 100% on your flight

$566

per person

Oct 30 - Nov 3

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Miami (MIA)

This historic resort features 2 restaurants, 2 outdoor pools, and a 24-hour gym. Relax with a drink at the bar/lounge and enjoy perks like free WiFi. There's a poolside bar on site, and a 24-hour front desk and concierge services are also provided.

Frequently asked questions

How much are vacation packages to Upper Sugarloaf Key?

You'll want to check out Travelocity's affordable $240 Upper Sugarloaf Key package deal. With all the cash you save on hotels and flights, you'll be able to splash out on some local travel experiences. Upper Sugarloaf Key, here you come!

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

It's difficult to beat Travelocity when it comes to putting together your Upper Sugarloaf Key package deal. There are as many as 400 partner airlines and 1,000,000 properties worldwide to select from. Lock in your trip now and get ready to cross another destination off your to-do list.

Why should I book my Upper Sugarloaf Key vacation package via Travelocity?

From incredible destinations to thrilling experiences, we have everything you need to satisfy your love for travel. Our 24/7 customer care will also ensure you're taken care of before, during and after your vacation. And don't panic if you notice a cheaper price on your reservation, we'll match it. That's our Price Match Guarantee.

Top Upper Sugarloaf Key hotel deals

Sugarloaf Key Hotel at KOA Resort

251 Co Rd 939, Summerland Key, FL

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

Escape to the Keys! Pet-Friendly Sugarloaf Key Bungalow - Great Amenities (84)

Stay at this cottage in Summerland Key. Enjoy free WiFi and air conditioning. Popular attractions Florida Keys Beaches and Upper Sugarloaf Key are located nearby.

Pet friendly

Free WiFi

Pet-Friendly Bungalow in Sugarloaf Key, FL - Fantastic Amenities (83)

Stay at this cottage in Summerland Key. Enjoy free WiFi and air conditioning. Popular attractions Florida Keys Beaches and Upper Sugarloaf Key are located nearby.

Pet friendly

Free WiFi

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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.