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
$254 nightly
The price is $286 total per night from Nov 30 to Dec 1
$286 total
Nov 30 - Dec 1
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 nice facility. Loved that we had our own space yet could walk a short walk to the pool, breakfast area or the bar.

Reviewed on Nov 9, 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
$234 nightly
The price is $263 total per night from Dec 2 to Dec 3
$263 total
Dec 2 - Dec 3
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 ...
Such a nice please thank you so much !

Reviewed on Nov 7, 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 Nov 30 to Dec 1
$320 total
Nov 30 - Dec 1
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 ...
The staff was excellent ! Super nice , accommodating, professional . The room was very clean and nice . Just what I expected . Probably the nicest staff I’ve ever dealt with in hotels I’ve been in . Which has been a lot . Thank you !

Reviewed on Nov 14, 2025

Opens in a new windowOpal Key Resort & Marina, Key West
Paradise Inn Key West - Adults Only

Paradise Inn Key West - Adults Only

3.5 out of 5
819 Simonton Street Key West FL
Fully refundableReserve now, pay when you stay
$192 nightly
The price is $216 total per night from Nov 30 to Dec 1
$216 total
Nov 30 - Dec 1
Total with taxes and fees
This hotel features an outdoor pool and a hot tub. Enjoy the free continental breakfast each morning. Self parking, a terrace, and a garden are also ...
Clean

Reviewed on Nov 15, 2025

Opens in a new windowParadise Inn Key West - Adults Only
Southwinds Motel

Southwinds Motel

2 out of 5
1321 Simonton Street Key West FL
$166 nightly
The price is $187 total per night from Nov 17 to Nov 18
$187 total
Nov 17 - Nov 18
Total with taxes and fees
This hotel features 2 outdoor pools and a bar/lounge. Enjoy the free continental breakfast each morning. Self parking, a picnic area, and luggage storage are ...
Nice motel traditional Key West building in a great position for downtown. Room was clean nice beds bathroom is very dated but clean. Staff were excellent.

Reviewed on Nov 14, 2025

Opens in a new windowSouthwinds Motel
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
1319 Duval Street Key West FL
Fully refundable
$249 nightly
The price is $280 total per night from Nov 30 to Dec 1
$280 total
Nov 30 - Dec 1
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 ...
Air conditioning was very loud which prevented a higher rating

Reviewed on Nov 10, 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
$283 nightly
The price is $319 total per night from Dec 1 to Dec 2
$319 total
Dec 1 - Dec 2
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, ...
It was great

Reviewed on Nov 10, 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
$299 nightly
The price is $336 total per night from Dec 14 to Dec 15
$336 total
Dec 14 - Dec 15
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 was a pleasant experience We enjoyed the amenities, restaurant and pool Staff was very nice, especially the morning Cafe Thank you 🙏

Reviewed on Nov 12, 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
$156 nightly
The price is $176 total per night from Nov 19 to Nov 20
$176 total
Nov 19 - Nov 20
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 ...
Very courteous staff. Stayed at this hotel many times. Love the ambiance and location near Duval Street.

Reviewed on Nov 15, 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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