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
$284 nightly
The price is $320 total per night from Dec 17 to Dec 18
$320 total
Dec 17 - Dec 18
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 ...
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Reviewed on Dec 2, 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 Dec 15 to Dec 16
$286 total
Dec 15 - Dec 16
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 ...
This is such a charming property. Our room was expansive and so comfortable. But it’s the delightful paths that meander thru trees and cottages that give this property such charm and delight. The staff was superlative!!! Everything was clean and bright and prompt.

Reviewed on Dec 3, 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
Fully refundableReserve now, pay when you stay
$284 nightly
The price is $320 total per night from Dec 14 to Dec 15
$320 total
Dec 14 - Dec 15
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 ...
Excellent

Reviewed on Dec 2, 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
$174 nightly
The price is $196 total per night from Dec 7 to Dec 8
$196 total
Dec 7 - Dec 8
Total with taxes and fees
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 ...
Nice place

Reviewed on Dec 1, 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
$280 nightly
The price is $315 total per night from Dec 17 to Dec 18
$315 total
Dec 17 - Dec 18
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 ...
Resort was fantastic and grounds were kept beautiful and clean. Staff was friendly and helpful. We ate at onsite restaurant and food was delicious.

Reviewed on Dec 5, 2025

Opens in a new windowSouthernmost Beach Resort and Guesthouses
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
$239 nightly
The price is $269 total per night from Dec 14 to Dec 15
$269 total
Dec 14 - Dec 15
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, ...
Great location great food too. Outdated could use new paint and updating but staff terrific. Will co e again

Reviewed on Dec 1, 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
$319 nightly
The price is $359 total per night from Dec 7 to Dec 8
$359 total
Dec 7 - Dec 8
Total with taxes and fees
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, ...
We really enjoyed our stay! The location was perfect. The room was cute and comfortable. Free parking was a plus. The grounds are beautiful. The staff was super friendly. The only thing guests should be aware of is that the office holds your keys in case they need to move cars around due to limited ...

Reviewed on Nov 30, 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
Fully refundableReserve now, pay when you stay
$299 nightly
The price is $336 total per night from Dec 15 to Dec 16
$336 total
Dec 15 - Dec 16
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 ...
Love this hotel ! One of my favorite here at the Keys ! Beautiful view and hotel !

Reviewed on Nov 30, 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
Fully refundableReserve now, pay when you stay
$149 nightly
The price is $168 total per night from Dec 16 to Dec 17
$168 total
Dec 16 - Dec 17
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 ...
The entire property is impressively clean from the room and dining area to the swimming pool. The bathroom is small, but has new and spotless fixtures. The surrounding area is calm and quiet, and the hotel’s close proximity to the beach makes the stay even better.

Reviewed on Dec 3, 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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