Key West Historic District Vacation Packages for 2026
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Key West Historic District Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Riverside Hotel
East Fort Lauderdale
$630
per person
Oct 21 - Oct 26
found 21 hours ago
Roundtrip flight included
Philadelphia (PHL) to Miami (MIA)
Book a stay at this business-friendly hotel in Fort Lauderdale. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the pool and the restaurant in our reviews. Popular attractions Las Olas Boulevard and Las Olas Beach are located nearby.
Southernmost House - Adult Exclusive
Old Town Key West
$1,870
per person
Oct 11 - Oct 18
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Key West (EYW)
Book a stay at this beach hotel in Key West. Enjoy free breakfast, free WiFi, and parking (surcharge). Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Duval Street and South Beach are located nearby.
Great location and nice historic home
Reviewed on Aug 1, 2026
The Key West Hotel
Key West Historic District
$2,853
per person
Oct 11 - Oct 18
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Key West (EYW)
Stay at this guesthouse in Key West. Enjoy free WiFi, room service, and daily housekeeping. Popular attractions Duval Street and Mallory Square are located nearby.
This is the best place to stay in Key West! It is a hotel but it has the quaint B&B vibes. The tiki bar by the pool is amazing and they are adding food soon which makes it literally perfect. Close to everything you’d want to do- walk or scooter. 10/10 recommend!
Reviewed on Jul 27, 2026
Kona Kai Oasis
Old Town Key West
$1,446
per person
Oct 11 - Oct 18
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Key West (EYW)
Stay at this guesthouse in Key West. Enjoy free WiFi, free parking, and a garden. Our guests praise the helpful staff in our reviews. Popular attractions Duval Street and South Beach are located nearby.
Will be back again! Love it
Reviewed on Aug 5, 2026
Soleado Hotel
East Fort Lauderdale
$680
per person
Oct 21 - Oct 26
found 21 hours ago
Roundtrip flight included
Philadelphia (PHL) to Miami (MIA)
Stay at this aparthotel in Fort Lauderdale. Enjoy free WiFi, parking (surcharge), and daily housekeeping. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Fort Lauderdale Beach and Las Olas Beach are located nearby.
Pier House Resort & Spa
Key West Historic District
$1,786
per person
Oct 11 - Oct 18
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Key West (EYW)
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 in our reviews. Popular attractions Duval Street and Mallory Square are located nearby.
Don't see what you're looking for?
See all available trips from Columbus to Key West Historic District
View all tripsKey West Historic District Vacation Packages
Trying to plan a way to package your Key West Historic District flight and hotel, while saving some money? The AARP Travel Center Powered by Expedia® Key West Historic District vacation packages can help. We're here to book everything you'll need to make your Key West Historic District trip one to remember. Our Travel Center is a one-stop shop where you can put together the best vacation package for you and your family. AARP Travel Center has a fabulous list of flights and lodgings, as well as Key West Historic District activities to select from.
Key West Historic District Hotel Deals
You can choose from around 1646 hotels. Whether you want to stay in the heart of the city or pick a spot that is near all the Key West Historic District hot spots, we have plenty of options available.
We have great deals on everything from family-friendly resorts that check off all the vacation must-haves to inexpensive hotels which are great for those on a budget. You can scan all the options and pick the hotel that is ideal for you. With AARP Travel Center's Key West Historic District hotel packages, you not only get a great rate on your flight, but also a wonderful place to stay.
Things to do in Key West Historic District
Key West Historic District has around 25,755 people that call this city their home. If you wanted to take a break from the hustle and bustle of a big city, then you are in the right spot. There are around 14 great attractions in and around Key West Historic District that can make your vacation a bit of an adventure. Not sure where to begin? Here are a several things that the area is known for:
- Smathers Beach
- Audubon House & Tropical Gardens
- Harry S. Truman Little White House
- Mallory Square
You can also check out our "Things to Do" page for more inspiration or to reserve an activity in Key West Historic District.
Book Together and Save
As an AARP Member, you can take advantage of all the great savings. You can save on select hotels worldwide, flights, and even rental cars. No matter what vacation package you pick, your membership savings helps you get a great deal. The hardest packing you'll have to do is for your suitcase. Bundle now and get ready for your Key West Historic District vacation.
Top Hotel Deals
Southernmost Beach Resort and Guesthouses
1319 Duval Street Key West FL
Book a stay at this beach 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 ...
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. ...
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 ...
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 ...
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 ...
The Reach Key West, Curio Collection by Hilton
1435 Simonton Street Key West FL
Book a stay at this beach resort in Key West. Enjoy a full-service spa, a private beach, and breakfast (surcharge). Our guests praise the helpful staff and the ...
Southwinds Motel
1321 Simonton Street Key West FL
Stay at this hotel in Key West. Enjoy free breakfast, 2 outdoor pools, and parking (surcharge). Our guests praise the breakfast and the pool in our reviews. ...
Douglas House - Adults Only
419 Amelia St Key West FL
Stay at this guesthouse in Key West. Enjoy free WiFi, daily housekeeping, and a garden. Popular attractions Duval Street and Ernest Hemingway Home and Museum ...
Opal Key Resort & Marina, Key West
245 Front Street Key West FL
Stay at this hotel in Key West. Enjoy a marina, 3 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. ...
The Marker Key West Harbor Resort
200 William Street Key West FL
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 ...
Winslow's Bungalows - Key West Historic Inns
725 Truman Avenue Key West FL
Stay at this hotel in Key West. Enjoy free WiFi, 3 outdoor pools, and breakfast (surcharge). Our guests praise the breakfast and the pool in our reviews. Popular ...
Ocean Key Resort - A Noble House Resort
Zero Duval St. Key West FL
Book a stay at this spa resort in Key West. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the helpful staff in our reviews. Popular ...
Heron House - Adult Only
512 Simonton St Key West FL
Stay at this B&B in Key West. Enjoy free breakfast, free WiFi, and a rooftop terrace. Our guests praise the breakfast and the pool in our reviews. Popular attractions ...
The Southernmost Inn - Adults Only
525 United Street Key West FL
Stay at this hotel in Key West. Enjoy free breakfast, 2 outdoor pools, and parking (surcharge). Our guests praise the breakfast and the pool in our reviews. ...
Eden House
1015 Fleming St Key West FL
Stay at this hotel in Key West. Enjoy free WiFi, in-room massages, and a 24-hour front desk. Our guests praise the pool and the helpful staff in our reviews. ...
Don't see what you're looking for?
See all available properties in Key West Historic District
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.
Thu, Aug 27 - Wed, Sep 2
ATL
Hartsfield-Jackson Atlanta Intl.
MIA
Miami Intl.
$90
Roundtrip
found 10 hours ago
Wed, Sep 9 - Sat, Sep 12
BOS
Logan Intl.
MIA
Miami Intl.
$159
Roundtrip
found 5 days ago
Wed, Sep 9 - Sat, Sep 12
BOS
Logan Intl.
MIA
Miami Intl.
$159
Roundtrip
found 5 days ago
Sun, Sep 6 - Fri, Sep 11
ORD
O'Hare Intl.
MIA
Miami Intl.
$171
Roundtrip
found 1 day ago
Wed, Sep 9 - Sat, Sep 12
BOS
Logan Intl.
MIA
Miami Intl.
$179
Roundtrip
found 5 days ago
Best points of interest in Key West
- Duval Street Vacations
- Mallory Square Vacations
- Fort Zachary Taylor Historic State Park Vacations
- Ernest Hemingway Home and Museum Vacations
- South Beach Vacations
- Key West Butterfly and Nature Conservatory Vacations
- Harry S. Truman Little White House Vacations
- Key West Lighthouse and Keeper's Quarters Museum Vacations
- Florida Keys Eco - Discovery Center Vacations
- Oldest House Museum and Garden Vacations
More AARP Member Vacation Packages
- Las Vegas Vacations
- New York Vacations
- Orlando Vacations
- Los Angeles Vacations
- Miami Vacations
- San Francisco Vacations
- New Orleans Vacations
- Chicago Vacations
- Fort Lauderdale Vacations
- Boston Vacations
- Honolulu Vacations
- San Diego Vacations
- Washington Vacations
- Toronto Vacations
- Anaheim Vacations
- Atlanta Vacations
- Nashville Vacations
- Seattle Vacations
- Phoenix Vacations
- Myrtle Beach Vacations
- Vancouver Vacations
- Palm Springs Vacations
- Denver Vacations
- Tampa Vacations
- Niagara Falls Vacations
- San Antonio Vacations
- Atlantic City Vacations
- Philadelphia Vacations
- Austin Vacations
- Dallas Vacations
More Types of Hotels
- Hotels with Air Conditioning in Key West Historic District
- Hotels with a Pool in Key West Historic District
- Hotels with WiFi in Key West Historic District
- Beach Hotels in Key West Historic District
- Hotel with wifi in Key West Historic District
- Hotel with a Concierge in Key West Historic District
- Hotels with Bars in Key West Historic District
- Hotels with Balconies in Key West Historic District
- Family Hotels in Key West Historic District
- Hotels with Complimentary Breakfast in Key West Historic District
- Luxury Hotels in Key West Historic District
- Hotels with Hot Tubs in Key West Historic District
- Resorts & Hotels with Spas in Key West Historic District
- Hotels with smoking rooms in Key West Historic District
- Smoke Free Hotels in Key West Historic District
- Cheap Hotels in Key West Historic District
- Adults Only Resorts & Hotels in Key West Historic District
- Pet-friendly Hotels in Key West Historic District
- Oceanfront Hotels in Key West Historic District
- Hotels with Free Airport Shuttle in Key West Historic District
- Hotels on the River in Key West Historic District
- Hotels with Early Check-in in Key West Historic District
- Lakefront Hotels in Key West Historic District
- Gay friendly Hotels in Key West Historic District
- Scuba Diving in Key West Historic District