Old Town Key West, FL
Key West
Visit Old Town Key West
Stay near popular Old Town Key West attractions
Things to do
Dolphin Watch Catamaran Sunset Sail w/ Tapas and Open Bar
$79
per adult
94% of travellers recommend
Key West Rum & Reggae: Snorkel & Sunset Sail Combo
$69
per adult
88% of travellers recommend
Shipwreck Treasure Museum Tickets
$19
per adult
80% of travellers recommend
Afternoon Reef Snorkel & Catamaran Sail w/ Open Bar in Key West
$68
per adult
90% of travellers recommend
Miami to Key West Day Trip with Activity Options
$39
per adult
84% of travellers recommend
Old Town Key West Hotel Deals
Southernmost Beach Resort and Guesthouses
1319 Duval Street Key West FL
Fully refundable
$203 nightly
The price is $228 total per night from Sep 1 to Sep 2
$228 total
Sep 1 - Sep 2
Total with taxes and fees
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 ...
8.8/10 Excellent! (3,510 reviews)
"Amazing stay from start to finish. Checking in was a breeze with a bottle of wine to start the stay. Had surf and turf at Cafe which was tender and cooked to perfection. The room was gorgeous with partial ocean view, breathtaking. They are redoing beach which they disclosed in advance, which when ..."
Reviewed on Aug 12, 2026
Casa Marina Key West, Curio Collection by Hilton
1500 Reynolds Street Key West FL
$286 nightly
The price is $322 total per night from Aug 24 to Aug 25
$322 total
Aug 24 - Aug 25
Total with taxes and fees
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 ...
8.6/10 Excellent! (843 reviews)
"Incredible property. We loved the rich history of this hotel. The recent updates only made the property even more wonderful."
Reviewed on Aug 12, 2026
The Reach Key West, Curio Collection by Hilton
1435 Simonton Street Key West FL
$216 nightly
The price is $243 total per night from Sep 3 to Sep 4
$243 total
Sep 3 - Sep 4
Total with taxes and fees
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 ...
8.6/10 Excellent! (1,014 reviews)
"Our room was nice. Very clean and the staff was pleasant. We wish we knew we couldn’t use the beach because of the seaweed."
Reviewed on Aug 11, 2026
Southwinds Motel
1321 Simonton Street Key West FL
$146 nightly
The price is $164 total per night from Aug 31 to Sep 1
$164 total
Aug 31 - Sep 1
Total with taxes and fees
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. ...
8.6/10 Excellent! (1,377 reviews)
"Old and worn out! Many physical and administrative issues. Also, extreme fees that were unknown until we arrived. We did not save money (as we thought) by using Expedia! Lots of detailed problems I won’t get into now, just don’t book a room at Southwinds in Key West."
Reviewed on Aug 11, 2026
Douglas House - Adults Only
419 Amelia St Key West FL
$109 nightly
The price is $123 total per night from Aug 25 to Aug 26
$123 total
Aug 25 - Aug 26
Total with taxes and fees
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 ...
9.6/10 Exceptional! (486 reviews)
"The room was large and clean. We liked the additional coffee station by the pool. The room could of uses a few more towels."
Reviewed on Aug 11, 2026
Opal Key Resort & Marina, Key West
245 Front Street Key West FL
$294 nightly
The price is $331 total per night from Aug 13 to Aug 14
$331 total
Aug 13 - Aug 14
Total with taxes and fees
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. ...
9.2/10 Wonderful! (1,179 reviews)
"I was pleasantly surprised by this hotel. The rooms are ample and well cared for. The Mexican restaurant embedded in the hotel was also an unexpected highlight. Everything was great with this stay. I would book again for sure."
Reviewed on Aug 12, 2026
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.
Check Old Town Key West hotel availability
Where to stay in Old Town Key West
Find the best Old Town Key West areas and neighborhoods for the activities you enjoy most. Learn more about Old Town Key West
Learn more about Old Town Key West
Downtown Key West
If you're spending some time in Downtown Key West, Duval Street and Ernest Hemingway Home and Museum are top sights worth seeing.
Key West Historic District
Travelers to Key West Historic District praise its fantastic nightlife. If you've got some more time to explore, be sure to make a stop by Duval Street and Florida Keys Beaches.
New Town
Though New Town might not have many top sights, you can venture to the surrounding area to see attractions like Smathers Beach and Key West Tropical Forest and Botanical Garden.
Uptown - Upper Duval
If you're spending some time in Uptown - Upper Duval, Duval Street and Florida Keys Beaches are top sights worth seeing.
Old Town Key West, FL
Explore a world of travel with Expedia
- Key West Hotels
- Oceanfront Hotels in Key West
- Condo Rentals in Key West
- Key West Historic District Hotels
- All-Inclusive Resorts in Key West
- Adults Only Resorts & in Key West
- Houseboats in Key West
- Pet-Friendly Hotels in Key West
- Cheap Hotels in Key West
- Romantic Hotels in Key West
- Resorts in Key West
- Family Hotels in Key West
- Beach Hotels in Key West
- Hotels near Duval Street
- Flights from Minneapolis (MSP) to Key West (EYW)
- Flights from Philadelphia (PHL) to Key West (EYW)
- Flights from Washington (DCA) to Key West (EYW)
- Flights from Jacksonville (JAX) to Key West (EYW)
- Flights from Richmond (RIC) to Key West (EYW)
- Flights from Tampa (TPA) to Key West (EYW)
- Flights from Hartford (BDL) to Key West (EYW)
- Flights from Nashville (BNA) to Key West (EYW)
- Flights from Charlotte (CLT) to Key West (EYW)
- Flights from Providence (PVD) to Key West (EYW)
- Flights from Pensacola (PNS) to Key West (EYW)
- Flights from Louisville (SDF) to Key West (EYW)
- Flights from Denver (DEN) to Key West (EYW)
- Flights from Chicago (ORD) to Key West (EYW)
- Flights from Cleveland (CLE) to Key West (EYW)
- Flights from Detroit (DTW) to Key West (EYW)
- Flights from Los Angeles (LAX) to Key West (EYW)
- Flights from Fort Myers (RSW) to Key West (EYW)
- Flights from Baltimore (BWI) to Key West (EYW)
- Flights from Newark Liberty Intl. Airport (EWR) to Key West (EYW)
- Flights from Miami (MIA) to Key West (EYW)
- Flights from Pittsburgh (PIT) to Key West (EYW)
- Flights from Charleston (CHS) to Key West (EYW)
- Flights from Kansas City (MCI) to Key West (EYW)
- Flights from Raleigh (RDU) to Key West (EYW)
- Flights from St. Louis (STL) to Key West (EYW)
- Flights from Cincinnati (CVG) to Key West (EYW)
- Flights from Columbus (CMH) to Key West (EYW)
- Flights from West Palm Beach (PBI) to Key West (EYW)
- Flights from Fort Lauderdale (FLL) to Key West (EYW)
- Flights from Atlanta (ATL) to Key West (EYW)
- Flights from Houston (IAH) to Key West (EYW)
- Flights from New Orleans (MSY) to Key West (EYW)
- Flights from Dallas (DFW) to Key West (EYW)
- Flights from Key West Intl.
- Flights from Boston (BOS) to Key West (EYW)
- Flights from Buffalo (BUF) to Key West (EYW)
- Flights from Naples (APF) to Key West (EYW)
- Flights from Orlando (MCO) to Key West (EYW)
- Flights from Indianapolis (IND) to Key West (EYW)
- Flights from Grand Rapids (GRR) to Key West (EYW)
- Flights from Sarasota (SRQ) to Key West (EYW)
- Flights from Washington (IAD) to Key West (EYW)
- Flights to Key West
- Flights from New York (JFK) to Key West (EYW)
- Visit Monroe County
- Visit Cudjoe Key
- Visit Geiger Key
- Visit Dredgers Key
- Visit Uptown - Upper Duval
- Old Town Key West Vacations
- All inclusive Vacation Packages Key West
- Visit Ramrod Key
- Visit Boca Chica Key
- Visit Stock Island
- Visit Downtown Key West
- Clarence S. Higgs Memorial Beach Park
- Key West Vacations
- Visit Melody Key
- Visit Sugarloaf Shores
- Visit Sugarloaf Key
- Visit Lower Keys
- Visit Sunset Key
- Visit Big Torch Key
- Visit Lower Florida Keys
- Key West Historic District Vacations
- Visit Truman Annex
- Visit Little Torch Key
- Visit Key West Historic District
- Ernest Hemingway Home and Museum
- Visit Big Pine Key
- Visit Rockland Key
- Visit Eden Pines
- Smathers Beach
- Visit Cow Key
- Visit Fleming Key
- Visit Historic Seaport
- Visit New Town
- Visit Summerland Key
- Visit Bahama Village
- Visit Raccoon Key
- Visit Key West
