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Top hotels in Old Town Key West

Douglas House

Douglas House

3 out of 5
419 Amelia St Key West FL
$449 nightly
The price is $505 total per night from Mar 10 to Mar 11
$505 total
Mar 10 - Mar 11
Total with taxes and fees
An outdoor pool, self parking, and concierge services are featured at this guesthouse. WiFi in public areas is free. A terrace, a garden, and a picnic area are ...
The staff were professional and courteous, the pool area was nice and a great addition in warmer weather, however this review is specific to room 1108D. This room consists of two bedrooms, a kitchen, a large living are and a huge balcony overlooking Duval Street.

Reviewed on Feb 10, 2026

Opens in a new windowDouglas House
Duval House

Duval House

3 out of 5
815 Duval St Key West FL
$401 nightly
The price is $448 total per night from Mar 8 to Mar 9
$448 total
Mar 8 - Mar 9
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.
We had a lovely, large room in a cottage. The common areas- gardens and walkways were beautiful. Very authentic Key West experience. The breakfasts were great!

Reviewed on Feb 13, 2026

Opens in a new windowDuval House
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
$552 nightly
The price is $622 total per night from Mar 12 to Mar 13
$622 total
Mar 12 - Mar 13
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 clean.

Reviewed on Feb 13, 2026

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
$614 nightly
The price is $691 total per night from Mar 4 to Mar 5
$691 total
Mar 4 - Mar 5
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 ...
Awsome resort. Great food and staff

Reviewed on Feb 11, 2026

Opens in a new windowOpal Key Resort & Marina, Key West
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
1319 Duval Street Key West FL
Fully refundable
$620 nightly
The price is $698 total per night from Mar 19 to Mar 20
$698 total
Mar 19 - Mar 20
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 ...
Everything was wonderful! I highly recommend and would come again.

Reviewed on Feb 12, 2026

Opens in a new windowSouthernmost Beach Resort and Guesthouses
Southwinds Motel

Southwinds Motel

2 out of 5
1321 Simonton Street Key West FL
$407 nightly
The price is $458 total per night from Feb 25 to Feb 26
$458 total
Feb 25 - Feb 26
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 ...
The rooms were clean, the staff was polite and helpful, and the provided light breakfast options provided were good.

Reviewed on Feb 13, 2026

Opens in a new windowSouthwinds Motel
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
$634 nightly
The price is $713 total per night from Mar 4 to Mar 5
$713 total
Mar 4 - Mar 5
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, ...
Location

Reviewed on Feb 9, 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
$707 nightly
The price is $796 total per night from Mar 1 to Mar 2
$796 total
Mar 1 - Mar 2
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 ...
Great location !! Beach was wonderful. Beautiful place. Definitely will be back.

Reviewed on Feb 9, 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
$499 nightly
The price is $561 total per night from Mar 1 to Mar 2
$561 total
Mar 1 - Mar 2
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 small but clean

Reviewed on Feb 14, 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.

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