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Top hotels in Old Town Key West

Douglas House - Adults Only

Douglas House - Adults Only

3 out of 5
419 Amelia St Key West FL
$128 nightly
The price is $144 total per night from Sep 9 to Sep 10
$144 total
Sep 9 - Sep 10
Total with taxes and fees
An outdoor pool is featured at this guesthouse, along with free WiFi in public areas and a terrace. A garden, a picnic area, and luggage storage are also on ...
"Loved this property. Have been coming to KW for last 40+ years and never stayed here? Great location. Our room was more like and apartment. We were down from Miami for rum festival and were close to all of the different events at Douglas. The property was meticulously kept. The staff was helpful. ..."

Reviewed on Sep 2, 2026

Opens in a new windowDouglas House - Adults Only
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
$240 nightly
The price is $270 total per night from Sep 7 to Sep 8
$270 total
Sep 7 - Sep 8
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, ...
"Great boutique hotel! The room was clean, the bed was very comfortable, and the location was perfect—just one block from Duval Street, with restaurants nearby. Breakfast was also better than I expected! Live music by the pool (afternoon and during breakfast) and at night was very quiet! Overall, ..."

Reviewed on Aug 30, 2026

Opens in a new windowLighthouse Hotel - Key West Historic Inns
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
$246 nightly
The price is $277 total per night from Sep 28 to Sep 29
$277 total
Sep 28 - Sep 29
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, ...
"Staff was very helpful and nice"

Reviewed on Sep 3, 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
$152 nightly
The price is $171 total per night from Sep 7 to Sep 8
$171 total
Sep 7 - Sep 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 ...
"Great location. Nice pool. Parking. Thirsty Rooster 🐓 bar out front was so much fun and a great vibe. Not to mention a close distance to Duval St. Where the action is. Deli and groceries across the street as well. We will be back"

Reviewed on Sep 3, 2026

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 refundableReserve now, pay when you stay
$210 nightly
The price is $237 total per night from Sep 13 to Sep 14
$237 total
Sep 13 - Sep 14
Total with taxes and fees
A full-service spa, 3 outdoor pools, and a restaurant are all featured at this hotel. Traveling on business? Take advantage of the 2 conference rooms, along ...
Opens in a new windowSouthernmost Beach Resort and Guesthouses
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
$272 nightly
The price is $306 total per night from Sep 13 to Sep 14
$306 total
Sep 13 - Sep 14
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 ...
Opens in a new windowCasa Marina Key West, Curio Collection by Hilton
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
$240 nightly
The price is $270 total per night from Sep 7 to Sep 8
$270 total
Sep 7 - Sep 8
Total with taxes and fees
This smoke-free hotel features 3 outdoor pools, a bar/lounge, and a poolside bar. WiFi in public areas is free. Self parking, a garden, and luggage storage are ...
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
Fully refundableReserve now, pay when you stay
$294 nightly
The price is $331 total per night from Sep 7 to Sep 8
$331 total
Sep 7 - Sep 8
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 ...
Opens in a new windowOpal Key Resort & Marina, Key West
Silver Palms Inn & Historic Homes

Silver Palms Inn & Historic Homes

3.5 out of 5
830 Truman Ave Key West FL
Fully refundableReserve now, pay when you stay
$149 nightly
The price is $168 total per night from Sep 8 to Sep 9
$168 total
Sep 8 - Sep 9
Total with taxes and fees
An outdoor pool is featured at this hotel, along with free WiFi in public areas and luggage storage. Enjoy the free continental breakfast each morning. There's ...
Opens in a new windowSilver Palms Inn & Historic Homes
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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

The Reach Key West, Curio Collection by Hilton

The Reach Key West, Curio Collection by Hilton

5 out of 5
Posted 4 hours ago
Travelocity Verified Review
"Staff was very helpful and nice"
A verified traveler stayed at The Reach Key West, Curio Collection by Hilton
The Reach Key West, Curio Collection by Hilton

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