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.

Hyatt Vacation Club at Windward Pointe, Key West

Save 100% on your flight

$956

per person

Oct 18 - Oct 23

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

This hotel features an outdoor pool, a hot tub, and a restaurant. Guests will appreciate free perks like free self parking and WiFi in public areas. A snack bar/deli, concierge services, and barbecue grills are also on offer.

Oceans Edge Key West Resort, Hotel & Marina

Save 100% on your flight

$1,151

per person

Nov 2 - Nov 9

found 1 day ago

Roundtrip non-stop 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.

Lighthouse Hotel - Key West Historic Inns

Old Town Key West

Save 100% on your flight

$1,351

per person

Nov 2 - Nov 9

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.

Bishop Hotel Key West

Old Town Key West

Save 100% on your flight

$1,007

per person

Nov 12 - Nov 19

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

This guesthouse's 2 outdoor pools and hot tub are among the featured amenities. Unwind with a drink at the poolside bar and enjoy perks like free continental breakfast and free WiFi. There's luggage storage and multilingual staff can provide around-the-clock assistance.

Winslow's Bungalows - Key West Historic Inns

Old Town Key West

Save 100% on your flight

$1,436

per person

Nov 2 - Nov 9

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.

The Perry Hotel & Marina Key West

Save 100% on your flight

$1,827

per person

Nov 2 - Nov 9

found 1 day ago

Roundtrip non-stop 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.

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 $956 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

$229 nightly

$258 total

Sep 8 - Sep 9

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

The Reach Key West, Curio Collection by Hilton

1435 Simonton Street, Key West, FL

Free Cancellation

Reserve now, pay when you stay

$277 nightly

$312 total

Sep 15 - Sep 16

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, and valet parking. Enjoy the outdoor pool and unwind at the bar/lounge and poolside bar.

On private beach

Pool

Casa Marina Key West, Curio Collection by Hilton

1500 Reynolds Street, Key West, FL

Free Cancellation

Reserve now, pay when you stay

$274 nightly

$308 total

Sep 2 - Sep 3

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

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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.