Sugarloaf Shores Vacation Packages for 2026
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Sugarloaf Shores Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Hyatt Vacation Club at Sunset Harbor, Key West
Old Town Key West
$1,588
per person
Dec 3 - Dec 9
just found
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
Stay at this hotel in Key West. Enjoy free WiFi, parking (surcharge), and concierge services. Popular attractions Duval Street and Mallory Square are located nearby.
Very spacious two bedroom villas.
Reviewed on Sep 15, 2026
The Marker Key West Harbor Resort
Key West Historic District
$1,919
per person
Dec 3 - Dec 9
just found
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
Book a stay at this business-friendly hotel in Key West. Enjoy free WiFi, 3 outdoor pools, and breakfast (surcharge). Our guests praise the pool and the helpful staff in our reviews. Popular attractions Duval Street and Mallory Square are located nearby.
Southernmost Beach Resort and Guesthouses
Old Town Key West
$1,711
per person
Dec 3 - Dec 9
just found
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
Book a stay at this spa hotel in Key West. Enjoy free WiFi, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Duval Street and South Beach are located nearby.
Good first impression checking in. Staff was friendly and courteous. Room was ok off of the Tranquility pool. We did not like the heavy frosted sliding bathroom door, it was loud. There also needs to be counter space or cabinet of some sort in the bathroom. We brought a table in so we could put our toiletries on it. There should be another mirror somewhere in the room other than the one in the bathroom. Our light and fan was on some kind of timer and turned on and off automatically at random times. Turning on at 7 am was not cool. The beach was gross with all the sargassum and stunk really bad. We booked at this hotel due to being on the beach and we didn’t even go on it at all. The resort next door had really clean and usable beach. Not sure why ours was so bad. One of the pools is under construction. The bar off the beach was nice except for the smell. Food was good. Good reminder communications from the hotel on events and happenings at the pools. Overall, good food and drinks, friendly staff and easily accessible to the main streets.
Reviewed on Sep 15, 2026
Lighthouse Hotel - Key West Historic Inns
Old Town Key West
$2,709
per person
Dec 3 - Dec 9
just found
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
Stay at this hotel in Key West. Enjoy free breakfast, free WiFi, and daily housekeeping. Our guests praise the helpful staff in our reviews. Popular attractions Duval Street and Ernest Hemingway Home and Museum are located nearby.
It’s small but needs major repairs to the building
Most rooms had soft floors
Termites eating the property away
Orkin there for 3 days drilling on property to try to get a handle on it
One room the floor broke and the person chipped her ankle and got a high sprain ankle
Another had mold infestation and bed bugs
Reviewed on Sep 14, 2026
The Gardens Hotel
Old Town Key West
$2,233
per person
Dec 3 - Dec 9
just found
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
Book a stay at this business-friendly B&B in Key West. Enjoy free breakfast, free WiFi, and 2 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Duval Street and Ernest Hemingway Home and Museum are located nearby.
Wonderful property and staff! Annette, Luna and George, our pool bartenders and breakfast staff were outstanding. Front desk staff very helpful and pleasant as well.
Beautiful gardens and grounds, clean rooms, love that the pool is open all night for swimming. Live music every afternoon.
Great location centrally located in old town, convenient to everything! Will definitely book here again!
Reviewed on Sep 12, 2026
Ridley House - Key West Historic Inns
Key West Historic District
$1,778
per person
Dec 3 - Dec 9
just found
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
Stay at this hotel in Key West. Enjoy free breakfast, free WiFi, and daily housekeeping. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Duval Street and Mallory Square are located nearby.
The Ridley House is beautiful and full of old world charm. Large bedrooms and great location. Breakfast each day was fabulous. Not your typical continental breakfast! We stayed in room 6 with a front balcony on Caroline St. Within the first 5 minutes of us being there, we locked ourselves out of the room, on the balcony b/c the door locks automatically when it shuts! Luckily some passersby were able to get the front desk to help us and it was just a funny story after that. We noticed the ear plugs on the side tables due to the roosters crowing and they weren't kidding. We discovered some of them roost high up in the trees, level with the balcony, and sing their "little" songs all night long! Also, another funny story to tell about one of our trips to KW. I would stay at the Ridley House again, but perhaps a room farther away from the road. Ha
Reviewed on Sep 14, 2026
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See all available trips from Columbus to Sugarloaf Shores
View all tripsSugarloaf Shores Vacation Packages
Looking to save both time and money on your upcoming holiday to Sugarloaf Shores? The AARP Travel Center Powered by Expedia® can help you do both. We can assist you with hotel bookings, flights, car rentals and more. You can get almost everything you need here to make your trip to Sugarloaf Shores the best one yet. Our Travel Center is a one-stop shop where you can put together the best vacation package for you. AARP Travel Center has an amazing choice of flights and hotels, and Sugarloaf Shores endeavors to pull from.
Hotel Deals in Sugarloaf Shores
Our listings include accommodations that are close to all the Sugarloaf Shores points of interest, and some that are just outside the city center for a more restful retreat.
From Sugarloaf Shores hotels with swimming pools and on-site restaurants, to boutique accommodations that add all the thoughtful touches, you'll find a hotel here that will make your trip astounding. With AARP Travel Center's Sugarloaf Shores hotel packages, you not only get a great rate on your flight, but also a wonderful place to stay.
Things to do in Sugarloaf Shores
The fact that you are traveling to Sugarloaf Shores means your trip will already be off to a great start. A little curiosity and asking the right people, like your hotel's concierge, goes a long way into having a unique experience.
Looking for more? Then Check out AARP Travel Center's "Things to Do" Page.
Package Your Sugarloaf Shores Vacation and Save
As an AARP Member, you can cash in on all the great deals. You'll save on select hotels worldwide, flights, and car rentals. No matter what Sugarloaf Shores vacation package you choose, your membership savings helps you get a great deal. So what are you waiting for? Book now and get ready for your Sugarloaf Shores vacation.
Top Hotel Deals
Southernmost Beach Resort and Guesthouses
1319 Duval Street Key West FL
Book a stay at this spa hotel in Key West. Enjoy free WiFi, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our ...
Blue Flamingo Resort Key West
3820 North Roosevelt Boulevard Key West FL
Book a stay at this family-friendly hotel in Key West. Enjoy free WiFi, 2 outdoor pools, and 2 restaurants. Our guests praise the pool and the helpful staff ...
Margaritaville Beach House Key West
2001 South Roosevelt Blvd Key West FL
Book a stay at this beach hotel in Key West. Enjoy breakfast (surcharge), a free airport shuttle, and room service. Our guests praise the pool and the restaurant ...
Ibis Bay Beach Resort
3101 N. Roosevelt Blvd Key West FL
Book a stay at this beach hotel in Key West. Enjoy free breakfast, free WiFi, and a private beach. Our guests praise the breakfast and the pool in our reviews. ...
Havana Cabana at Key West
3420 N. Roosevelt Blvd Key West FL
Book a stay at this business-friendly hotel in Key West. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the pool and the helpful ...
Pier House Resort & Spa
1 Duval St Key West FL
Book a stay at this beach resort in Key West. Enjoy a full-service spa, a private beach, and 2 bars/lounges. Our guests praise the pool and the helpful staff ...
Beachside Resort & Residences
3841 N Roosevelt Blvd Key West FL
Book a stay at this beach hotel in Key West. Enjoy free WiFi, 2 restaurants, and a private beach. Our guests praise the pool and the helpful staff in our reviews. ...
Casa Marina Key West, Curio Collection by Hilton
1500 Reynolds Street Key West FL
Book a stay at this beach resort in Key West. Enjoy 2 outdoor pools, a full-service spa, and a private beach. Popular attractions Duval Street and South Beach ...
Hyatt Vacation Club at Windward Pointe, Key West
3675 South Roosevelt Boulevard Key West FL
Stay at this hotel in Key West. Enjoy free WiFi, free parking, and a snack bar/deli. Our guests praise the pool and the helpful staff in our reviews. Popular ...
DoubleTree Resort by Hilton Grand Key - Key West
3990 S Roosevelt Blvd Key West FL
Book a stay at this business-friendly resort in Key West. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff ...
Hilton Garden Inn Key West / The Keys Collection
3850 N Roosevelt Blvd Key West FL
Book a stay at this business-friendly hotel in Key West. Enjoy 2 restaurants, breakfast (surcharge), and a free area shuttle. Our guests praise the pool and ...
Hyatt Centric Key West Resort and Spa
601 Front St Key West FL
Book a stay at this beach resort in Key West. Enjoy free WiFi, a full-service spa, and a marina. Our guests praise the pool and the helpful staff in our reviews. ...
Hampton Inn Key West FL
3755 S Roosevelt Blvd Key West FL
Book a stay at this business-friendly hotel in Key West. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the breakfast and the ...
La Concha Key West, Autograph Collection
430 Duval St Key West FL
Book a stay at this business-friendly hotel in Key West. Enjoy free WiFi, 3 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
Parrot Key Hotel & Villas
2801 N Roosevelt Blvd Key West FL
Book a stay at this beach hotel in Key West. Enjoy free WiFi, 4 outdoor pools, and breakfast (surcharge). Our guests praise the pool and the bar in our reviews. ...
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See all available properties in Sugarloaf Shores
View all propertiesLowest 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.
Top Flight Deals
These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.
Wed, Oct 7 - Mon, Oct 19
ATL
Hartsfield-Jackson Atlanta Intl.
MIA
Miami Intl.
$50
Roundtrip
found 4 days ago
Sat, Nov 7 - Tue, Nov 17
BOS
Logan Intl.
MIA
Miami Intl.
$159
Roundtrip
found 2 days ago
Tue, Oct 6 - Tue, Oct 20
BOS
Logan Intl.
MIA
Miami Intl.
$159
Roundtrip
found 3 hours ago
Sat, Nov 7 - Tue, Nov 17
BOS
Logan Intl.
MIA
Miami Intl.
$233
Roundtrip
found 2 days ago
Tue, Nov 3 - Tue, Nov 10
LGA
LaGuardia
MIA
Miami Intl.
$236
Roundtrip
found 1 day ago
Best points of interest in Summerland Key
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