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
The price is $308 total per night from Dec 17 to Dec 18
$308 total
per night
Dec 17 - Dec 18
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 ...
This place is AMAZING! From the gorgeous landscaping, to the delicious free breakfast, to the beautiful room we had...I can't say enough. We will definitely stay here every time we're in KW. We had 3 other couples with us and they all said the same. Top notch!

Reviewed on Dec 16, 2025

Opens in a new windowWinslow's Bungalows - 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
The price is $353 total per night from Dec 17 to Dec 18
$353 total
per night
Dec 17 - Dec 18
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 ...
Great helpful staff

Reviewed on Dec 14, 2025

Opens in a new windowOpal Key Resort & Marina, Key West
Heron House - Adult Only

Heron House - Adult Only

3.5 out of 5
512 Simonton St Key West FL
The price is $190 total per night from Dec 17 to Dec 18
$190 total
per night
Dec 17 - Dec 18
This bed & breakfast features an outdoor pool and a rooftop terrace. Guests will appreciate free perks like continental breakfast and WiFi in public areas. A ...
Everything was great! Loved the clean room, prompt delivery of towels and the breakfast daily was excellent. The staff was very nice and very helpful! I highly recommend and we will be back Thank you.

Reviewed on Dec 13, 2025

Opens in a new windowHeron House - Adult Only
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
1319 Duval Street Key West FL
Fully refundable
The price is $285 total per night from Dec 18 to Dec 19
$285 total
per night
Dec 18 - Dec 19
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 ...
Room was spotless. Only complaint was the water took awhile to heat up

Reviewed on Dec 10, 2025

Opens in a new windowSouthernmost Beach Resort and Guesthouses
The Palms Hotel

The Palms Hotel

3 out of 5
820 White St Key West FL
The price is $245 total per night from Dec 17 to Dec 18
$245 total
per night
Dec 17 - Dec 18
This guesthouse features a bar/lounge, a poolside bar, and an outdoor pool. Guests will appreciate free perks like continental breakfast and WiFi in public areas. ...
Simply serving coffee in real cups would make a big difference. Skip the breakfast, great local restaurants right around the corner. Wonderful Staff, great recommendations on food and things to do.

Reviewed on Dec 10, 2025

Opens in a new windowThe Palms Hotel
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
The price is $284 total per night from Dec 18 to Dec 19
$284 total
per night
Dec 18 - Dec 19
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, ...
Staff was amazing, friendly, and helpful

Reviewed on Dec 11, 2025

Opens in a new windowThe Reach Key West, Curio Collection by Hilton
Wicker Guesthouse

Wicker Guesthouse

3.5 out of 5
913 Duval Street Key West FL
The price is $291 total per night from Dec 17 to Dec 18
$291 total
per night
Dec 17 - Dec 18
This guesthouse features an outdoor pool and a bar/lounge. Guests will appreciate free perks like free self parking and WiFi in public areas. A terrace, a garden, ...
So quiet, quaint and clean!

Reviewed on Dec 13, 2025

Opens in a new windowWicker Guesthouse
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
The price is $410 total per night from Dec 17 to Dec 18
$410 total
per night
Dec 17 - Dec 18
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 ...
The resort was nice and the pools were very nice. The pool staff was friendly and accommodating. The room was clean but the toilet in the bathroom ran non stop , the housecleaning wasn’t done daily but they did bring us towels and water upon our request. We love to walk but it is a distance to walk ...

Reviewed on Dec 10, 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
The price is $213 total per night from Dec 18 to Dec 19
$213 total
per night
Dec 18 - Dec 19
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 ...
Hot tub and pool was great! Breakfast had multiple options. Rooms could have been a little cleaner. Walls were dirty. Tv remote was very dirty. It was a great stay overall.

Reviewed on Dec 15, 2025

Opens in a new windowThe Southernmost Inn - Adults Only
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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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