Southernmost Point Vacation Deals: Southernmost Point, Old Town Key West Holidays

Southernmost Point vacation package deals

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

Caribbean House

Old Town Key West

CA $788

per person

Dec 1 - Dec 5

found 22 hours ago

Roundtrip flight included

Toronto (YTO) to Key West (EYW)

Stay at this 3-star B&B in Key West. Enjoy free breakfast, free WiFi, and parking (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Duval Street and Ernest Hemingway Home and Museum are located nearby.

Ella's Cottages - Key West Historic Inns

Old Town Key West

CA $1,020

per person

Dec 1 - Dec 5

found 22 hours ago

Roundtrip flight included

Toronto (YTO) to Key West (EYW)

Stay at this 3.5-star business-friendly hotel in Key West. Enjoy free breakfast, free WiFi, and parking (surcharge). Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Duval Street and Ernest Hemingway Home and Museum are located nearby.

Ridley House - Key West Historic Inns

Key West Historic District

CA $994

per person

Dec 1 - Dec 5

found 22 hours ago

Roundtrip flight included

Toronto (YTO) to Key West (EYW)

Stay at this 3.5-star hotel in Key West. Enjoy free breakfast, free WiFi, and daily housekeeping. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Duval Street and Mallory Square are located nearby.

Pier House Resort & Spa

Key West Historic District

CA $1,430

per person

Dec 1 - Dec 5

found 22 hours ago

Roundtrip flight included

Toronto (YTO) to Key West (EYW)

Stay at this 4-star beach resort in Key West. Enjoy a full-service spa, a private beach, and 2 bars/lounges. Our guests praise the pool and the bar in our reviews. Popular attractions Duval Street and Mallory Square are located nearby.

Lighthouse Hotel - Key West Historic Inns

Old Town Key West

CA $969

per person

Dec 1 - Dec 5

found 22 hours ago

Roundtrip flight included

Toronto (YTO) to Key West (EYW)

Stay at this 3.5-star hotel in Key West. Enjoy free breakfast, free WiFi, and daily housekeeping. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Duval Street and Ernest Hemingway Home and Museum are located nearby.

Hyatt Vacation Club at Beach House, Key West

CA $872

per person

Nov 9 - Nov 12

found 14 hours ago

Roundtrip non-stop flight included

Halifax (YHZ) to Key West (EYW)

Stay at this 3.5-star eco-certified hotel in Key West. Enjoy free WiFi, free parking, and concierge services. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Duval Street and Smathers Beach are located nearby.

Frequently asked questions

How much are vacation packages to Southernmost Point?

Let Travelocity take the hassle out of arranging your next big trip to Southernmost Point. Book our awesome CA $788 package deal and save both money and time. With your hotel and flights sorted, you can channel your energy into planning the fun parts of your adventure — like ticking off those must-see attractions!

Where can I get the best vacation package deals for Southernmost Point?

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Can I go on vacation to Southernmost Point at this time?

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Top Southernmost Point hotel deals

Southernmost Beach Resort and Guesthouses

1319 Duval Street, Key West, FL

Free cancellation

CA $244

CA $368 total

Oct 6 - Oct 7

includes taxes & fees

Stay at this 4-star beach hotel in Key West. Enjoy free WiFi, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the bar in our reviews. Popular attractions Duval Street and South Beach are located nearby.

Pool

Spa

Casa Marina Key West, Curio Collection by Hilton

1500 Reynolds Street, Key West, FL

Free cancellation

Reserve now, pay when you stay

CA $248

CA $362 total

Oct 14 - Oct 15

includes taxes & fees

Stay at this 4-star beach resort in Key West. Enjoy 2 outdoor pools, a full-service spa, and a private beach. Popular attractions Duval Street and South Beach are located nearby.

On private beach

Pool

The Reach Key West, Curio Collection by Hilton

1435 Simonton Street, Key West, FL

Free cancellation

Reserve now, pay when you stay

CA $275

CA $392 total

Oct 1 - Oct 2

includes taxes & fees

Stay at this 4-star beach resort in Key West. Enjoy a full-service spa, a private beach, and breakfast (surcharge). Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Duval Street and South Beach are located nearby.

On private beach

Pool

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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.