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
Key West Dolphin Watch & Snorkel Combo With Unlimited Beer & Wine
$55
per adult
92% of travellers recommend
Sunset Sail in Key West with Beverages Included
$79
per adult
98% of travellers recommend
Old Town Key West Hotel Deals
Southernmost Beach Resort and Guesthouses
1319 Duval Street Key West FL
The price is $269 total per night from Sep 28 to Sep 29
$269 total
per night
Sep 28 - Sep 29
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 ...
8.6/10 Excellent! (3,608 reviews)
"The check in staff was not friendly. The elevator in our building wasn’t working, the pool was closed and the beach was closed because of Scargasim. Also there was a $50.00 per night parking fee and none of these points were discussed with us beforehand and no discounts were offered. Two other couples ..."
Reviewed on Sep 16, 2026
Casa Marina Key West, Curio Collection by Hilton
1500 Reynolds Street Key West FL
The price is $315 total per night from Sep 27 to Sep 28
$315 total
per night
Sep 27 - Sep 28
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 ...
8.4/10 Very Good! (916 reviews)
"We booked an oceanfront balcony room, but ended up on the first floor. We asked to be put on an upper floor or for a partial refund and the staff refused both."
Reviewed on Sep 17, 2026
Southwinds Motel
1321 Simonton Street Key West FL
The price is $174 total per night from Sep 20 to Sep 21
$174 total
per night
Sep 20 - Sep 21
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! (1,379 reviews)
"Second time staying at this hotel and will be back ASAP"
Reviewed on Sep 16, 2026
Winslow's Bungalows - Key West Historic Inns
725 Truman Avenue Key West FL
The price is $270 total per night from Sep 20 to Sep 21
$270 total
per night
Sep 20 - Sep 21
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 ...
9.2/10 Wonderful! (1,421 reviews)
"We had a nice stay overall. The breakfast was wonderful. The pools were amazing. The property was beautiful and you could see that the staff realt tried hard to make it nice. The staff was very helpful with any issues. We would stay here again. A few things were misnleading such as the water at the ..."
Reviewed on Sep 16, 2026
The Reach Key West, Curio Collection by Hilton
1435 Simonton Street Key West FL
The price is $263 total per night from Sep 29 to Sep 30
$263 total
per night
Sep 29 - Sep 30
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 ...
Opal Key Resort & Marina, Key West
245 Front Street Key West FL
The price is $331 total per night from Sep 20 to Sep 21
$331 total
per night
Sep 20 - Sep 21
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! (1,191 reviews)
"This place had everything we needed. Can’t wait to come back!"
Reviewed on Sep 16, 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
- Houseboats in Key West
- Ocean View in Key West
- Resorts in Key West
- Hotels in Key West
- Highgate Independent Hotels in Key West
- All-Inclusive in Key West
- 3 Star Hotels in Key West
- Best Western Hotels in Key West
- Truman Annex Hotels
- 4 Star Hotels in Key West
- Old Town Key West Hotels
- Key West Historic District Hotels
- Sunset Key Hotels
- Downtown Key West Hotels
- Flights from Orlando (MCO) to Key West (EYW)
- Flights from Tampa (TPA) to Key West (EYW)
- Flights to Stock Island
- Flights to Key West Intl.
- JetBlue Airways Boston (BOS) to Key West (EYW) flights
- Flights to Fleming Key
- Flights to Sugarloaf Key
- Delta Air Lines Atlanta (ATL) to Key West (EYW) flights
- Flights to Key West
- Flights to Raccoon Key
- Old Town Key West Vacations
- Ernest Hemingway Home & Museum
- Key West All Inclusive Vacation Packages
- Visit Downtown Key West
- Visit Sugarloaf Key
- Visit New Town
- Visit Key West Historic District
- Key West All Inclusive Vacation Packages
- Where to stay in Lower Sugarloaf Key
- Where to stay in Boca Chica Key
- Where to stay in Dredgers Key
- Visit Key West
- Where to stay in Key West
- Duval Street
- Key Haven All Inclusive Vacation Packages
- Visit Stock Island
- Where to stay in Sugarloaf Key
- Where to stay in Key Haven
- Fleming Key All Inclusive Vacation Packages
- Visit Uptown - Upper Duval
- Visit Dredgers Key
- Visit Lower Florida Keys
- Mallory Square
- Visit Boca Chica Key
- Lower Florida Keys All Inclusive Vacation Packages
- Visit Truman Annex
- Key West All Inclusive Vacation Packages
- Where to stay in Stock Island
- Big Pine Key Vacations
- Visit Cow Key
- Where to stay in Lower Florida Keys
- Key West All Inclusive Vacation Packages
- Where to stay in Cudjoe Key
- Visit Fleming Key
- Visit Summerland Key
- Key West Vacations
- Visit Bahama Village
- Clarence S. Higgs Memorial
- Key Haven All Inclusive Vacation Packages
- Fleming Key All Inclusive Vacation Packages
- Where to stay in Big Pine Key
- Stock Island All Inclusive Vacation Packages
- Marathon Vacations
- Key West All Inclusive Vacation Packages
- Cow Key Vacations
- Visit Historic Seaport
- Things to do in Boca Chica Key
- Things to do in Summerland Key
- Things to do in Ramrod Key
- Things to do in Marathon
- Things to do in Little Torch Key
- Things to do in Cudjoe Key
- Things to do in Key West
- Things to do in Lower Keys
- Things to do in Sugarloaf Key
- Things to do in Big Pine Key
- Things to do in Stock Island
