Cheap 2025 Key West Historic District Hotels

Choose from 1766 Key West Historic District Hotel Deals

Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
1319 Duval Street, Key West, FL
Free Cancellation
0.96 km from Key West Historic District
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Stay at this 4-star beach hotel in Key West. Enjoy free WiFi, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the bar in our reviews. ...
Hyatt Centric Key West Resort and Spa

Hyatt Centric Key West Resort and Spa

4 out of 5
601 Front St, Key West, FL
Free Cancellation
Reserve now, pay when you stay
0.83 km from Key West Historic District
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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 bar in our reviews. Popular ...
The Southernmost Inn - Adults Only

The Southernmost Inn - Adults Only

3 out of 5
525 United Street, Key West, FL
Free Cancellation
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0.83 km from Key West Historic District
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Stay at this 3-star hotel in Key West. Enjoy free breakfast, 2 outdoor pools, and parking (surcharge). Our guests praise the breakfast and the pool in our reviews. ...
Casa Marina Key West, Curio Collection by Hilton

Casa Marina Key West, Curio Collection by Hilton

4 out of 5
1500 Reynolds Street, Key West, FL
Free Cancellation
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1.25 km from Key West Historic District
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Stay at this 4-star beach resort in Key West. Enjoy 2 outdoor pools, a full-service spa, and a private beach. Popular attractions Duval Street and South Beach ...
La Concha Key West, Autograph Collection

La Concha Key West, Autograph Collection

4 out of 5
430 Duval St, Key West, FL
Free Cancellation
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0.49 km from Key West Historic District
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Book a stay at this business-friendly hotel in Key West. Enjoy free WiFi, 3 restaurants, and 2 bars/lounges. Our guests praise the bar and the helpful staff ...
Pier House Resort & Spa

Pier House Resort & Spa

4 out of 5
1 Duval St, Key West, FL
Free Cancellation
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0.95 km from Key West Historic District
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Stay at this 4-star beach resort in Key West. Enjoy a full-service spa, a private beach, and 2 bars/lounges. Our guests praise the pool and the bar in our reviews. ...
NYAH Key West - Adults Only

NYAH Key West - Adults Only

3 out of 5
420 Margaret Street, Key West, FL
Free Cancellation
Reserve now, pay when you stay
0.34 km from Key West Historic District
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Stay at this 3-star guesthouse in Key West. Enjoy free breakfast, 3 outdoor pools, and a rooftop terrace. Our guests praise the pool and the helpful staff in ...
The Reach Key West, Curio Collection by Hilton

The Reach Key West, Curio Collection by Hilton

4 out of 5
1435 Simonton Street, Key West, FL
1.04 km from Key West Historic District
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Stay at this 4-star beach resort in Key West. Enjoy a full-service spa, a private beach, and breakfast (surcharge). Our guests praise the helpful staff and the ...
Orchid Key Inn - Adults Only

Orchid Key Inn - Adults Only

3.5 out of 5
1004 Duval St, Key West, FL
0.57 km from Key West Historic District
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Stay at this 3.5-star hotel in Key West. Enjoy free breakfast, free WiFi, 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

4 out of 5
725 Truman Avenue, Key West, FL
Free Cancellation
Reserve now, pay when you stay
0.39 km from Key West Historic District
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Stay at this 4-star hotel in Key West. Enjoy free breakfast, free WiFi, and 3 outdoor pools. Our guests praise the breakfast and the pool in our reviews. Popular ...
Duval House

Duval House

3 out of 5
815 Duval St, Key West, FL
0.44 km from Key West Historic District
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Stay at this 3-star B&B in Key West. Enjoy parking (surcharge), daily housekeeping, and a garden. Our guests praise the breakfast and the pool in our reviews. ...
Bishop Hotel Key West

Bishop Hotel Key West

4 out of 5
822 Fleming St, Key West, FL
0.28 km from Key West Historic District
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Stay at this 4-star guesthouse in Key West. Enjoy free breakfast, free WiFi, and 2 outdoor pools. Popular attractions Duval Street and Ernest Hemingway Home ...
The Marker Key West Harbor Resort

The Marker Key West Harbor Resort

4 out of 5
200 William Street, Key West, FL
0.61 km from Key West Historic District
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Stay at this 4-star eco-certified hotel in Key West. Enjoy free WiFi, 3 outdoor pools, and breakfast (surcharge). Our guests praise the pool and the bar in our ...
Southwinds Motel

Southwinds Motel

2 out of 5
1321 Simonton Street, Key West, FL
0.91 km from Key West Historic District
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Stay at this hotel in Key West. Enjoy free breakfast, 2 outdoor pools, and a 24-hour front desk. Our guests praise the breakfast and the pool in our reviews. ...
Opal Key Resort & Marina, Key West

Opal Key Resort & Marina, Key West

4 out of 5
245 Front Street, Key West, FL
Free Cancellation
Reserve now, pay when you stay
0.87 km from Key West Historic District
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Stay at this 4-star hotel in Key West. Enjoy a marina, 3 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in ...
The Cabana Inn Key West - Adults Only

The Cabana Inn Key West - Adults Only

3 out of 5
413 Applerouth Lane, Key West, FL
Free Cancellation
Reserve now, pay when you stay
0.49 km from Key West Historic District
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Stay at this 3-star guesthouse in Key West. Enjoy free breakfast, parking (surcharge), and daily housekeeping. Our guests praise the breakfast and the pool in ...
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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.

Take the Family to Key West Historic District

Looking to plan your next big trip with the whole family? Key West Historic District offers some of the best family-friendly activities, hotels, and amenities, so you can rest easy, because your clan is going to love the vacation that you plan. And with the AARP Travel Center Powered by Expedia® as your guide, traveling to Key West Historic District will be easy. You'll find that with your member status, you can combine your members-only discount with the best rates from Expedia. Forget stressing over the cost—you'll be getting the best value available.

Family-Friendly Activities in Key West Historic District

Once you and your family get to Key West Historic District, you'll need some fun activities that everyone will want to be a part of. Some favorites in the area include Punta Tombo, National Naval Aviation Museum, or La Plage de Maui. Remember to check the weather forecast before you pack your bags, so you don't have any surprises along the way. You may experience a longer than usual commute time, so please prepare in advance and double-check your reservation and excursion schedule.

Key West Historic District Kid-Friendly Hotels

If you are looking for quality time at your hotel, our family-friendly accommodations have an array of amenities that will make your trip extra comfortable. From kids' clubs, roll-away beds, cribs, and enormous rooms, you won't have to lift a finger to make sure the entire crew is satisfied with the accommodations you pick.

Your kids and grandkids will be thrilled to stay at one of our Key West Historic District kid-friendly hotels. And the adults will love that they're located near attractions, dining options, and activities.

Book Now & Save

If you're looking to make a legendary family getaway that you and your relatives will reminisce over for years, you're in good hands with AARP Travel. Whether you're looking for a crazy activity, educational enjoyment, or just some laid-back family time, all you have to do is pack your bags and get ready to share memories that will last a lifetime. Pack your bags and load your family up in the car, because Key West Historic District awaits.