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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
$214 nightly
The price is $241 total per night from Dec 1 to Dec 2
$241 total
Dec 1 - Dec 2
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 ...
"The Douglas House is a wonderful place to stay. Our room exceeded our expectations and the staff was very friendly and helpful. We will definitely stay here again."

Reviewed on Nov 1, 2026

Opens in a new windowDouglas House - Adults 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
$272 nightly
The price is $306 total per night from Nov 15 to Nov 16
$306 total
Nov 15 - Nov 16
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, free WiFi ...
"A mixed bag. Good: - location. - quiet (apart from the Roosters and party goers). - beach cafe food. - pool. - beds. - balcony room (part ocean view). Bad: - parking charges. - bad hotel management putting our family in the middle of an obvious group of party people. - grumpy and rude pool bar staff. ..."

Reviewed on Nov 1, 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
$244 nightly
The price is $275 total per night from Nov 3 to Nov 4
$275 total
Nov 3 - Nov 4
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, ...
"I love that it's right on the water and I'm able to use the amenities at the neighboring resort"

Reviewed on Nov 1, 2026

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
$304 nightly
The price is $342 total per night from Nov 4 to Nov 5
$342 total
Nov 4 - Nov 5
Total with taxes and fees
A private beach, a full-service spa, and 2 outdoor pools are all featured at this smoke-free resort. Relax with sun loungers and beach umbrellas, and cool off ...
"First off do not go through Expedia; the hotel supposedly could not tell me how much the nightly rate was when I called because it was booked through a “third party” and then the hotel charged me an additional 500$ (nightly Resort Charge + tax) when we checked out after I paid for the resort and ..."

Reviewed on Nov 1, 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
$219 nightly
The price is $246 total per night from Nov 3 to Nov 4
$246 total
Nov 3 - Nov 4
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 happy with our stay and our time in Key West, thank you!"

Reviewed on Nov 1, 2026

Opens in a new windowThe Southernmost Inn - Adults Only
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
$245 nightly
The price is $276 total per night from Nov 3 to Nov 4
$276 total
Nov 3 - Nov 4
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 Nov 4 to Nov 5
$331 total
Nov 4 - Nov 5
Total with taxes and fees
A marina, a 24-hour gym, and a restaurant are all featured at this luxury 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
Southwinds Motel

Southwinds Motel

2 out of 5
1321 Simonton Street Key West FL
$180 nightly
The price is $202 total per night from Dec 1 to Dec 2
$202 total
Dec 1 - Dec 2
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 ...
Opens in a new windowSouthwinds Motel
Duval House

Duval House

3 out of 5
815 Duval St Key West FL
$211 nightly
The price is $234 total per night from Nov 11 to Nov 12
$234 total
Nov 11 - Nov 12
Total with taxes and fees
This bed & breakfast features a terrace, concierge services, and self parking. A garden, a picnic area, and express check-in are also on offer.
Opens in a new windowDuval House
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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

Douglas House - Adults Only

Douglas House - Adults Only

5 out of 5
Posted 11 hours ago
Travelocity Verified Review
"The Douglas House is a wonderful place to stay. Our room exceeded our expectations and the staff was very friendly and helpful. We will definitely stay here again."
A verified traveler stayed at Douglas House - Adults Only
Douglas House - Adults Only

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