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

Southernmost Point vacation package deals

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

The Perry Hotel & Marina Key West

Save 100% on your flight

$461

per person

Oct 19 - Oct 23

found 1 day ago

Roundtrip flight included

Boston (BOS) to Key West (EYW)

A marina, 2 restaurants, and 2 outdoor pools are all featured at this smoke-free hotel. Traveling for business? Take advantage of the free WiFi in public areas, laundry service, and conference space. 2 poolside bars and 2 bars/lounges are featured at this hotel, along with a 24-hour gym.

Lighthouse Hotel - Key West Historic Inns

Old Town Key West

Save 100% on your flight

$920

per person

Nov 21 - Nov 25

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

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, and a picnic area are also on offer.

Oceans Edge Key West Resort, Hotel & Marina

Save 100% on your flight

$547

per person

Oct 19 - Oct 23

found 1 day ago

Roundtrip flight included

Boston (BOS) to Key West (EYW)

A marina, 6 outdoor pools, and a 24-hour gym are all featured at this smoke-free hotel. Business travelers can take advantage of the free WiFi in public areas. The restaurant provides options for dining, while the bar/lounge and poolside bar are great spots to unwind.

Hyatt Vacation Club at Beach House, Key West

Save 100% on your flight

$699

per person

Nov 8 - Nov 12

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

This hotel features an outdoor pool and a hot tub. Relax with a drink at the bar/lounge and enjoy perks like free self parking and free WiFi. A safe deposit box and concierge services are also provided.

Winslow's Bungalows - Key West Historic Inns

Old Town Key West

Save 100% on your flight

$986

per person

Nov 21 - Nov 25

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

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 areas. Self parking, a garden, and luggage storage are also offered.

Casa Marina Key West, Curio Collection by Hilton

Old Town Key West

Save 100% on your flight

$987

per person

Nov 21 - Nov 25

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

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 with a drink at the beachside bar. Enjoy the gym and perks like free WiFi.

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 $461 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?

With as many as 400 air carriers and 1,000,000 hotels across the world, you can't beat Travelocity. Take advantage of our comprehensive range and pick up the best package deal to Southernmost Point. Doesn't it feel amazing when travel is that easy?

Why should I book my Southernmost Point vacation bundle via Travelocity?

Travel should be about making fantastic new memories and leaving all your worries behind — which is why we have a professional team of customer service experts on hand around-the-clock should you need them. On top of that, our Price Match Guarantee ensures you'll always get the best deal available on our huge range of package deals. So what are you waiting for? There's no time like the present to secure that vacation you've always dreamed of.

Top Southernmost Point hotel deals

Southernmost Beach Resort and Guesthouses

1319 Duval Street, Key West, FL

Free Cancellation

$207 nightly

$233 total

Sep 30 - Oct 1

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 for business? Take advantage of the 24-hour business center, laundry service, and conference space.

Pool

Spa

Casa Marina Key West, Curio Collection by Hilton

1500 Reynolds Street, Key West, FL

Free Cancellation

Reserve now, pay when you stay

$207 nightly

$232 total

Sep 25 - Sep 26

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 with a drink at the beachside bar. Enjoy the gym and perks like free WiFi.

On private beach

Pool

Hyatt Centric Key West Resort and Spa

601 Front St, Key West, FL

Free Cancellation

Reserve now, pay when you stay

$243 nightly

$273 total

Sep 22 - Sep 23

Total with taxes and fees

This eco-certified resort features a full-service spa, a marina, and a restaurant. Enjoy the outdoor pool and perks like free WiFi. Enjoy the 24-hour gym and unwind at the bar/lounge and poolside bar.

Pool

Spa

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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.