Fleming Key Vacation Packages for 2026
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Fleming Key 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
found 10 hours ago
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
found 10 hours ago
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
found 10 hours ago
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.
Booked this place for the location and how many pools they had. Didn’t know until we got there that the largest pool was under renovation and completely out of service. Not the end of the world but this made the other 2 pools (combined they were the size of the 1 that was closed) more cramped. Then I booked an ocean view room. Always do. Only to find out when we get there that the beach access is closed due to the awful smelling seaweed (sargassum) that is washing up. Again, not the end of the world but it smells gross! Overall, stay was relaxing but could’ve been better. Sheets always felt like they had sand in them after the cleaning crew would come in and make the bed up so I always had to wipe them out before we got in for the evening. Older rooms but you can tell they are trying to renovate and make them nicer/newer. Overall pretty happy with the place
Reviewed on Sep 15, 2026
Lighthouse Hotel - Key West Historic Inns
Old Town Key West
$2,709
per person
Dec 3 - Dec 9
found 10 hours ago
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
found 10 hours ago
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
found 10 hours ago
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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View all tripsFleming Key Vacation Packages
Hoping to save time and money on your next vacation to Fleming Key? The AARP Travel Center Powered by Expedia® can help you do both. We're here to book everything you'll need to make your Fleming Key trip one to remember. Our Travel Center is a one-stop shop where you can put together the best Fleming Key vacation package for you. AARP Travel Center has a fabulous choice of flights and lodgings, and Fleming Key things to do to pull from.
Hotel Deals in Fleming Key
Our listings include lodgings that are close to all the Fleming Key points of interest, and others that are just outside the city center for a quieter retreat.
From Fleming Key hotels with swimming pools and on-site restaurants, to boutique accommodations that add all the extra touches, you'll get a hotel here that will make your trip astounding. With AARP Travel Center's Fleming Key hotel packages, you not only get a great rate on your flight, but also a great place to stay.
Things to do in Fleming Key
The fact that you are traveling to Fleming Key means your vacation is off to a fabulous start. A little curiosity and asking the right people, like your hotel's concierge, goes a long way into having a unique experience.
The AARP Travel Center "Things to Do" page has more great activities that you can book.
Package Your Fleming Key Vacation and Save
With so much going on in Fleming Key, you'll be wanting to plan your itinerary, not devoting time to finding the cheapest hotel. The AARP Travel Center Powered by Expedia® allows you to quickly reserve everything you want, and save a little money on your vacation. You can coordinate your whole trip, including activities in Fleming Key from only one place. So what are you waiting for? Book now and save!
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 ...
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 ...
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. ...
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. ...
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 ...
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.
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 5 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 13 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 Key West
- Duval Street Vacations
- Southernmost Point Vacations
- Mallory Square Vacations
- Smathers Beach Vacations
- Ernest Hemingway Home and Museum Vacations
- Fort Zachary Taylor Historic State Park Vacations
- South Beach Vacations
- Clarence S. Higgs Memorial Beach Park Vacations
- Key West Golf Club Vacations
- Florida Keys National Marine Sanctuary Vacations
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