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.

Cavalier Hotel South Beach

South Beach

Save 100% on your flight

per person

Oct 15 - Oct 21

found 1 day ago

Roundtrip flight included

Boston (BOS) 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.

Casablanca Miami Beach

North Beach

per person

Oct 8 - Oct 15

found 12 hours ago

Roundtrip flight included

New York (JFK) to Miami (MIA)

An outdoor pool, valet parking, and laundry facilities are featured at this aparthotel. A grocery/convenience store, a communal living room, and express check-out are also on offer.

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

per person

Oct 15 - Oct 21

found 1 day ago

Roundtrip flight included

Boston (BOS) 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.

Park Central South Beach

South Beach

per person

Oct 15 - Oct 21

found 1 day ago

Roundtrip flight included

Boston (BOS) 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.

Henrosa Hotel

South Beach

Save 100% on your flight

per person

Oct 15 - Oct 21

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.

Pelican Grand Beach Resort - A Noble House Resort

East Fort Lauderdale

Save 100% on your flight

per person

Oct 12 - Oct 16

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

This luxury hotel features a private beach, a full-service spa, and 2 restaurants. Enjoy the outdoor pool and unwind at the bar/lounge and poolside bar.

Frequently asked questions

How much are vacation packages to Upper Sugarloaf Key?

You'll want to check out Travelocity's affordable $355 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.