Name: Southernmost Beach Resort and Guesthouses
Price range: $302 total
Rating: 8.8

Your Old Town Key West Vacation

Organizing your next exciting getaway just got a whole lot easier with a vacation package to Old Town Key West. Take in the best this neighborhood has to offer while making precious memories you'll replay for years. Some leading nearby attractions to check out during your trip to Old Town Key West include Ernest Hemingway Home and Museum, Audubon House and Tropical Gardens and Mallory Square. Expedia will help put your plans into action. Book your ideal Old Town Key West vacation now.

The Latest Old Town Key West Vacation Packages

Price found within the past 48 hours. Click for updated prices.

Hyatt Vacation Club at Windward Pointe, Key West

Save 100% on your flight

$1,063

per person

Jul 15 - Jul 19

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Key West (EYW)

9.4/10 Exceptional! (1,121 reviews)

Excellent stay! Walkable to the Smathers beach... rooms were very clean. Pool has great ocean view. Amenities were good!

Reviewed on Jun 9, 2026

Hyatt Vacation Club at Beach House, Key West

Save 100% on your flight

$1,154

per person

Jul 15 - Jul 19

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Key West (EYW)

9.4/10 Exceptional! (1,078 reviews)

Property well very clean and maintained. Staff was very friendly and accommodating. Rooms had everything you would need and very clean. Great place to stay!

Reviewed on Jun 8, 2026

The Key West Hotel

Key West Historic District

Save 100% on your flight

$1,169

per person

Aug 13 - Aug 16

found 1 day ago

Roundtrip non-stop flight included

Atlanta (ATL) to Key West (EYW)

9.2/10 Wonderful! (558 reviews)

We loved staying here and highly recommended it. Only thing that people might not like is the solo musicians play till 11pm every night. We didn’t mind it since we are not early birds.

Reviewed on Jun 7, 2026

Tropical Dreaming by Avantstay 4 Blks to Beach! Private Pool!

Old Town Key West

Save 100% on your flight

$3,199

per person

Jul 24 - Jul 30

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Key West (EYW)

10/10 Exceptional! (1 review)

Loved the closeness to Duval st and the privacy

Reviewed on Oct 17, 2025

Coconut Beach Resort

Old Town Key West

$1,162

per person

Jul 15 - Jul 19

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Key West (EYW)

8.8/10 Excellent! (193 reviews)

This was a great place to stay! Clean and well-placed on Key West. Pool and patio were great for getting some sun.

Reviewed on May 29, 2026

Where to stay in Old Town Key West

Find the best Old Town Key West areas and neighborhoods for the activities you enjoy most. Learn more about Old Town Key West

Key West Historic District

2 out of top 10 points of interest in this area

4.5/5(4,090 area reviews)

Old Town Key West boasts a rich history with 2485 historic buildings, and is home to popular attractions like Ernest Hemingway House and Mallory Square. Enjoy the lively atmosphere in the central business district.

Old Town Key West Hotel Deals

Southernmost Beach Resort and Guesthouses

1319 Duval Street Key West FL

Fully refundableReserve now, pay when you stay

$302 total

per night

Jun 22 - Jun 23

8.8/10 Excellent! (3,390 reviews)

"Very pleasantly surprised by the facilities. Staff was great, amenities and the very nice room were top notch."

Reviewed on Jun 13, 2026

Casa Marina Key West, Curio Collection by Hilton

1500 Reynolds Street Key West FL

Fully refundableReserve now, pay when you stay

$319 total

per night

Jun 23 - Jun 24

8.6/10 Excellent! (707 reviews)

"Very beautiful....feels like old money clasic vibes. Feels like you stepped back in time to an area when"

Reviewed on Jun 12, 2026

The Reach Key West, Curio Collection by Hilton

1435 Simonton Street Key West FL

Fully refundableReserve now, pay when you stay

$266 total

per night

Jun 24 - Jun 25

8.6/10 Excellent! (1,019 reviews)

"Stayed the first week of June. Rooms were nice but property felt very dated. Not a lot of beaches in Key West so was excited to find a property with a man made one. Unfortunately there was a ton of seaweed and it was essentially not usable. The pool was small and underwhelming. Food and drink on ..."

Reviewed on Jun 11, 2026

See all 1,287 properties in Old Town Key West

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.