
Exclusive Southernmost Point Vacation Deals
Southernmost Point vacation package deals
Price found within the past 48 hours. Click for updated prices.

Hyatt Vacation Club at Windward Pointe, Key West
per person
Sep 20 - Sep 22
found 1 day ago
Roundtrip 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.

Orchid Key Inn - Adults Only
Old Town Key West
Save 100% on your flight
per person
Aug 18 - Aug 23
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
This hotel features a bar/lounge, a poolside bar, and an outdoor pool. Enjoy the hot tub and free perks like continental breakfast and WiFi in public areas. Self parking, a garden, and dry cleaning are also offered.

Casa Marina Key West, Curio Collection by Hilton
Old Town Key West
per person
Sep 26 - Sep 30
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.

Lighthouse Hotel - Key West Historic Inns
Old Town Key West
per person
Sep 26 - Sep 28
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.

Winslow's Bungalows - Key West Historic Inns
Old Town Key West
per person
Sep 26 - Sep 28
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.

Almond Tree Inn Hotel - Adults Only
Old Town Key West
per person
Sep 26 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
This hotel features a bar/lounge, a poolside bar, and an outdoor pool. Business travelers can take advantage of the free WiFi in public areas. Enjoy the hot tub and free continental breakfast each morning.
Frequently asked questions
Top Southernmost Point hotel deals

Southernmost Beach Resort and Guesthouses
1319 Duval Street, Key West, FL
Free Cancellation
$259 nightly
The price is $291 total per night
$291 total
Aug 4 - Aug 5
Total includes 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
$270 nightly
The price is $304 total per night
$304 total
Aug 5 - Aug 6
Total includes 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

The Reach Key West, Curio Collection by Hilton
1435 Simonton Street, Key West, FL
Free Cancellation
Reserve now, pay when you stay
$236 nightly
The price is $266 total per night
$266 total
Jul 18 - Jul 19
Total includes 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
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View all propertiesLowest 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.