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

Q: Why should I book my Upper Sugarloaf Sound vacation bundle with Travelocity?

With our Price Match Guarantee , we'll match any better price you find. Add to that our 24/7 support and high-quality service and the vacation you've been dreaming of is well within reach.

Upper Sugarloaf Sound 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 Sound?

If you love the sound of stress-free planning and big savings, our $355 Upper Sugarloaf Sound vacation package has got you sorted. With your flights and hotels sorted, organizing your getaway around this popular attraction is easier than ever.

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

You can snap up sensational Upper Sugarloaf Sound package deals with Travelocity. Select from 400 air carriers and 1,000,000 properties worldwide and turn your travel dreams into reality.

Why should I book my Upper Sugarloaf Sound vacation bundle with Travelocity?

With our Price Match Guarantee, we'll match any better price you find. Add to that our 24/7 support and high-quality service and the vacation you've been dreaming of is well within reach.

Top Upper Sugarloaf Sound hotel deals

Sugar Loaf Lodge

17001 Overseas Hwy, Summerland Key, FL

Free Cancellation

Reserve now, pay when you stay

$99 nightly

$111 total

Aug 10 - Aug 11

Total includes taxes and fees

This hotel features a marina, 2 outdoor tennis courts, and a restaurant. Enjoy the outdoor pool and perks like free self parking and free WiFi. A bar/lounge and a garden are also provided.

Pool

Parking included

Sublimely private luxury home with enveloping oceanfront views near Key West

This vacation home features a hot tub and a sauna. Families will appreciate the arcade/game room and barbecue grills. A garden and laundry facilities are also provided.

Pool

Hot Tub

The Sunset Suites of Pelico Palms

This vacation home featured laundry facilities and barbecue grills.

Pool

Kitchen

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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.