Find a Hotel in Old Town Key West

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Top hotels in Old Town Key West

Winslow's Bungalows - Key West Historic Inns

Winslow's Bungalows - Key West Historic Inns

4 out of 5
725 Truman Avenue, Key West, FL
Fully refundableReserve now, pay when you stay
$214 nightly
The price is $241 total per night from Oct 27 to Oct 28
$241 total
Oct 27 - Oct 28
Total with taxes and fees
This smoke-free hotel features 3 outdoor pools, a bar/lounge, and a poolside bar. Guests will appreciate free perks like continental breakfast and WiFi in public ...
Very clean

Reviewed on Oct 22, 2025

Opens in a new windowWinslow's Bungalows - Key West Historic Inns
Ella's Cottages - Key West Historic Inns

Ella's Cottages - Key West Historic Inns

3.5 out of 5
811 Simonton Street, Key West, FL
Fully refundableReserve now, pay when you stay
$254 nightly
The price is $286 total per night from Oct 27 to Oct 28
$286 total
Oct 27 - Oct 28
Total with taxes and fees
An outdoor pool, self parking, and concierge services are featured at this hotel. Guests will appreciate free perks like continental breakfast and WiFi in public ...
Large spacious updated room, excellent location and very quiet.

Reviewed on Oct 22, 2025

Opens in a new windowElla's Cottages - Key West Historic Inns
Opal Key Resort & Marina, Key West

Opal Key Resort & Marina, Key West

4 out of 5
245 Front Street, Key West, FL
$284 nightly
The price is $320 total per night from Oct 26 to Oct 27
$320 total
Oct 26 - Oct 27
Total with taxes and fees
A marina, a 24-hour gym, and a restaurant are all featured at this smoke-free hotel. Enjoy the outdoor pool and visit the 3 bars/lounges and poolside bar for ...
We enjoyed our stay at the Opal would definitely come back.

Reviewed on Oct 20, 2025

Opens in a new windowOpal Key Resort & Marina, Key West
Lighthouse Hotel - Key West Historic Inns

Lighthouse Hotel - Key West Historic Inns

3.5 out of 5
902 Whitehead St, Key West, FL
Fully refundableReserve now, pay when you stay
$244 nightly
The price is $275 total per night from Oct 27 to Oct 28
$275 total
Oct 27 - Oct 28
Total with taxes and fees
This hotel features an outdoor pool and a poolside bar. Guests will appreciate free perks like continental breakfast and WiFi in public areas. A terrace, a garden, ...
My friend and I had an amazing three days in Key West. Lighthouse Inn was a huge contributor to this awesomely positive experience. Rooms were clean and well-stocked with towels. My friend and I would always arrive at the tail end of breakfast. Even so, there was always an ample variety of food available. ...

Reviewed on Oct 22, 2025

Opens in a new windowLighthouse Hotel - Key West Historic Inns
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
1319 Duval Street, Key West, FL
Fully refundableReserve now, pay when you stay
$225 nightly
The price is $253 total per night from Oct 26 to Oct 27
$253 total
Oct 26 - Oct 27
Total with taxes and fees
This hotel features a full-service spa, 3 outdoor pools, and a restaurant. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. Traveling ...
A great place to stay!

Reviewed on Oct 18, 2025

Opens in a new windowSouthernmost Beach Resort and Guesthouses
Southwinds Motel

Southwinds Motel

2 out of 5
1321 Simonton Street, Key West, FL
$162 nightly
The price is $183 total per night from Oct 26 to Oct 27
$183 total
Oct 26 - Oct 27
Total with taxes and fees
This hotel features 2 outdoor pools and a bar/lounge. Enjoy the free continental breakfast each morning. A picnic area, luggage storage, and laundry facilities ...
There was an issue with the location and facilities of the room but they were resolved with no extra effort

Reviewed on Oct 21, 2025

Opens in a new windowSouthwinds Motel
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
Fully refundableReserve now, pay when you stay
$262 nightly
The price is $295 total per night from Oct 27 to Oct 28
$295 total
Oct 27 - Oct 28
Total with taxes and fees
This resort features a private beach, a full-service spa, and a restaurant. Traveling on business? Take advantage of the express check-out, laundry service, ...
Ty was the best bartender. He makes the best drinks and very friendly to everyone sitting at the bar. Food was good.

Reviewed on Oct 22, 2025

Opens in a new windowThe Reach Key West, Curio Collection by Hilton
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
Fully refundableReserve now, pay when you stay
$287 nightly
The price is $323 total per night from Oct 26 to Oct 27
$323 total
Oct 26 - Oct 27
Total with taxes and fees
A private beach, a full-service spa, and 2 outdoor pools are all featured at this smoke-free resort. Relax with sun loungers and beach umbrellas, and cool off ...
This hotel is beautiful. Great view from the room. Staff is amazing

Reviewed on Oct 19, 2025

Opens in a new windowCasa Marina Key West, Curio Collection by Hilton
The Southernmost Inn - Adults Only

The Southernmost Inn - Adults Only

3 out of 5
525 United Street, Key West, FL
$139 nightly
The price is $156 total per night from Oct 27 to Oct 28
$156 total
Oct 27 - Oct 28
Total with taxes and fees
This hotel's 2 outdoor pools and hot tub are among the featured amenities. Enjoy the free continental breakfast each morning. Self parking, a coffee shop, and ...
everyone was helpful

Reviewed on Oct 20, 2025

Opens in a new windowThe Southernmost Inn - Adults Only
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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.

Old Town Key West Hotel Guide

Don’t keep your travel plans on repeat year after year. The same city with the same hotel every season will bore you and give you an itch to go looking for something new. Expand your geographical horizons to more than just those five blocks around your usual haunt.

Nowhere else can you find better deals on Old Town Key West area hotels. You’ll find the best prices on the quirky, the haunted, the old, the new, and the legendary. If you’re wondering what side of the pricing scale some of these hotels fall on, you need not to worry. Compare cheap hotels near Old Town Key West to find the perfect one to will fit your budget.

Leave the ordinary routine you’re set on behind and go. Go anywhere you want. Anywhere that makes you think, “I wonder what that’s like?” Part of Travelocity’s mission is to get you off-the-beaten path and the hotels near Old Town Key West are perfect for that. Find your new favorite watering hole on a quiet street. Discover a place to escape for the weekend with tasty local fare and unique sights. We want you to consider the places outside your normal comfort zone. Browse our selection and find the ideal hotel, in a place you’d like to explore.

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