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Top hotels in Old Town Key West

Opal Key Resort & Marina, Key West

Opal Key Resort & Marina, Key West

4 out of 5
245 Front Street Key West FL
$294 nightly
The price is $331 total per night from Jun 11 to Jun 12
$331 total
Jun 11 - Jun 12
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 ...
"Opal key was an amazing place to stay. The entire staff were friendly and helpful. My wife and I were celebrating our 31st wedding anniversary and we kinda felt a little spoiled by the amenities and service. If there was a negative we couldn’t get the room temperature down to where we like it. But ..."

Reviewed on Jun 5, 2026

Opens in a new windowOpal Key Resort & Marina, 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
$210 nightly
The price is $236 total per night from Jun 10 to Jun 11
$236 total
Jun 10 - Jun 11
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 ...
"Beautiful property, nice location. Friendly staff."

Reviewed on Jun 4, 2026

Opens in a new windowWinslow's Bungalows - Key West Historic Inns
Heron House - Adult Only

Heron House - Adult Only

3.5 out of 5
512 Simonton St Key West FL
$170 nightly
The price is $191 total per night from Jun 8 to Jun 9
$191 total
Jun 8 - Jun 9
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 ...
"We enjoyed our stay, location was great!"

Reviewed on Jun 2, 2026

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 refundableReserve now, pay when you stay
$261 nightly
The price is $294 total per night from Jun 29 to Jun 30
$294 total
Jun 29 - Jun 30
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 ...
"Look, we had a nice time. I put "OK" for your survey questions which may seem like we didn't enjoy. But, it would be hard to put "Good" for your survey answers. The beach was unusable due to dead, smelly seaweed that permeated the main pool, overall exterior (stairs, pool area, etc.) rooster poop, ..."

Reviewed on Jun 5, 2026

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
$266 nightly
The price is $299 total per night from Jun 24 to Jun 25
$299 total
Jun 24 - Jun 25
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 resort. Clean. Would stay again. Only complaint is they were hosting a prom the week we stayed. Our room was close to the prom and we heard quite a bit of noise which made it difficult to sleep."

Reviewed on Jun 4, 2026

Opens in a new windowThe Reach Key West, Curio Collection by Hilton
Southwinds Motel

Southwinds Motel

2 out of 5
1321 Simonton Street Key West FL
$164 nightly
The price is $185 total per night from Jun 7 to Jun 8
$185 total
Jun 7 - Jun 8
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 ...
"Basic bare bones room, not new, its a motel but what else do you need in Key West, place to sleep and shower, this is a place to crash and isnt fancy but location is great, market across the street, bar and liquor store in front of motel, 5 min walk to Duvall and 1 block from beach. It does the job ..."

Reviewed on Jun 5, 2026

Opens in a new windowSouthwinds Motel
Wicker Guesthouse

Wicker Guesthouse

3.5 out of 5
913 Duval Street Key West FL
$79 nightly
The price is $89 total per night from Jun 15 to Jun 16
$89 total
Jun 15 - Jun 16
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, ...
"Great location to attractions and restaurants. Convenient breakfast which was simple but good. Staff were courteous and helpful. Only negative was no table or chair in room, so you had to use chairs and tables in courtyard."

Reviewed on Jun 5, 2026

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
$283 nightly
The price is $319 total per night from Jun 30 to Jul 1
$319 total
Jun 30 - Jul 1
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 ...
"c"

Reviewed on Jun 4, 2026

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
$161 nightly
The price is $181 total per night from Jun 10 to Jun 11
$181 total
Jun 10 - Jun 11
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 friendly staff helped us order our mopeds and even had someone pick us up"

Reviewed on Jun 3, 2026

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.

Recent Old Town Key West hotel reviews by fellow wanderers

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