Key West Historic District Vacation Packages for 2026

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Key West Historic District Flight + Hotel packages

Price found within the past 48 hours. Click for updated prices.
The Penguin Hotel

The Penguin Hotel

South Beach
Save 100% on your flight
$702
per person
Nov 14 - Nov 21
found 19 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Miami (MIA)
Book a stay at this beach hotel in Miami Beach. Enjoy free WiFi, a beach locale, and breakfast (surcharge). Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Collins Avenue Shopping Area and Lincoln Road Mall are located nearby.
Hotel is showing some aging and the breakfast at the other / sister hotel was a zoo

Reviewed on Oct 12, 2026

Mondrian South Beach

Mondrian South Beach

South Beach
Save 100% on your flight
$833
per person
Nov 14 - Nov 21
found 19 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Miami (MIA)
Book a stay at this luxury hotel in Miami Beach. Enjoy free WiFi, a full-service spa, and a marina. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Collins Avenue Shopping Area and Lincoln Road Mall are located nearby.
Fontainebleau Miami Beach

Fontainebleau Miami Beach

Mid Beach
Save 100% on your flight
$1,387
per person
Nov 14 - Nov 21
found 19 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Miami (MIA)
Book a stay at this luxury hotel in Miami Beach. Enjoy free WiFi, 4 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Miami Beach Boardwalk and Lincoln Road Mall are located nearby.
Boulan South Beach

Boulan South Beach

South Beach
Save 100% on your flight
$753
per person
Nov 14 - Nov 21
found 19 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Miami (MIA)
Book a stay at this luxury hotel in Miami Beach. Enjoy a beach locale, 2 coffee shops/cafes, and a rooftop terrace. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Lincoln Road Mall and Collins Avenue Shopping Area are located nearby.
No hot water in the shower.

Reviewed on Oct 12, 2026

The Key West Hotel

The Key West Hotel

Key West Historic District
Save 100% on your flight
$3,272
per person
Nov 30 - Dec 7
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) 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.
Property was everything as described, clean, in the heart of the excitement that is Key West Pool was refreshing and close to tiki bar and local entertainment. The room was spacious, clean and comfy beds. There were issues and there was really no staff to address. Most impactive was the fire alarm. First started going off rang for a min or two, then reset. Happened a dozen times, each causing us to avoid sleep, leave room to make sure nothing was wrong. It wasn't. Then around 10 PM it went off and would not stop. Tried to call office, but nobody there after 6pm. Freaking insane, no emergency contact, maintenance number, nothing. We sent email in hopes it w May have been monitored... nope. Been 2 days and heard nothing back at all. Found the bartender at on site tici bar and though he abd is barback wete busy they found a ladder, called someone who told them to remove the devise. Eureka after almost 3 hours problem solved. Safety device removed and left peace and quite, perhaps fo fire warning, buy fine Also internet and this TV / entertainment no work. No maintenance, no visible router to reboot, be gave up and ended the insanity Maintenance guy was at the door early morning to properly troubleshoot or replace fire annunciator We only were booked for a night so when we checked out in morning front desk girl simply apologized and was actually sort of blowing us off as she was leaving the desk empty the service a near $600 o/n should offer

Reviewed on Oct 6, 2026

La Costa Beach Club

La Costa Beach Club

$1,252
per person
Dec 24 - Dec 29
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Miami (MIA)
Book a stay at this beach aparthotel in Pompano Beach. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the helpful staff in our reviews. Popular attractions Pompano Beach and Deerfield Beach are located nearby.
It wasnt bad. Simple and cheap

Reviewed on Oct 10, 2026

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Key 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 1651 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

Southernmost Beach Resort and Guesthouses

1319 Duval Street Key West FL
0.9 km from Key West Historic District
Book a stay at this spa hotel in Key West. Enjoy 3 outdoor pools, a full-service spa, and 2 poolside bars. Our guests praise the pool and the helpful staff in ...
Casa Marina Key West, Curio Collection by Hilton

Casa Marina Key West, Curio Collection by Hilton

1500 Reynolds Street Key West FL
1.25 km from Key West Historic District
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 Southernmost ...
The Southernmost Inn - Adults Only

The Southernmost Inn - Adults Only

525 United Street Key West FL
0.83 km from Key West Historic District
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. ...
Winslow's Bungalows - Key West Historic Inns

Winslow's Bungalows - Key West Historic Inns

725 Truman Avenue Key West FL
0.39 km from Key West Historic District
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 ...
Pier House Resort & Spa

Pier House Resort & Spa

1 Duval St Key West FL
0.95 km from Key West Historic District
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 ...
Opal Key Resort & Marina, Key West

Opal Key Resort & Marina, Key West

245 Front Street Key West FL
0.87 km from Key West Historic District
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. ...
Southwinds Motel

Southwinds Motel

1321 Simonton Street Key West FL
0.91 km from Key West Historic District
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. ...
Authors of Key West Guest House

Authors of Key West Guest House

725 White St. & Petronia Key West FL
0.65 km from Key West Historic District
Stay at this B&B in Key West. Enjoy free breakfast, free WiFi, and daily housekeeping. Our guests praise the helpful staff and the clean rooms in our reviews. ...
The Reach Key West, Curio Collection by Hilton

The Reach Key West, Curio Collection by Hilton

1435 Simonton Street Key West FL
1.04 km from Key West Historic District
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 ...
La Concha Key West, Autograph Collection

La Concha Key West, Autograph Collection

430 Duval St Key West FL
0.49 km from Key West Historic District
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 ...
Douglas House - Adults Only

Douglas House - Adults Only

419 Amelia St Key West FL
0.72 km from Key West Historic District
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 ...
Ocean Key Resort - A Noble House Resort

Ocean Key Resort - A Noble House Resort

Zero Duval St. Key West FL
1 km from Key West Historic District
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 ...
Duval House

Duval House

815 Duval St Key West FL
0.42 km from Key West Historic District
Stay at this B&B in Key West. Enjoy parking (surcharge), daily housekeeping, and a garden. Our guests praise the breakfast and the pool in our reviews. Popular ...
Paradise Inn Key West - Adults Only

Paradise Inn Key West - Adults Only

819 Simonton Street Key West FL
0.33 km from Key West Historic District
Book a stay at this business-friendly hotel in Key West. Enjoy free breakfast, parking (surcharge), and a garden. Our guests praise the breakfast and the pool ...
Hyatt Centric Key West Resort and Spa

Hyatt Centric Key West Resort and Spa

601 Front St Key West FL
0.83 km from Key West Historic District
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. ...
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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.

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.

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