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

Hyatt Vacation Club at Beach House, Key West
Save 100% on your flight
per person
Oct 27 - Oct 30
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.

Almond Tree Inn Hotel - Adults Only
Old Town Key West
Save 100% on your flight
per person
Oct 9 - Oct 13
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.

Orchid Key Inn - Adults Only
Old Town Key West
Save 100% on your flight
per person
Oct 9 - Oct 13
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
Save 100% on your flight
per person
Oct 23 - Oct 26
found 1 day ago
Roundtrip 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.

Hyatt Vacation Club at Windward Pointe, Key West
per person
Oct 31 - Nov 2
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.

Southernmost Beach Resort and Guesthouses
Old Town Key West
per person
Oct 9 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
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.
Frequently asked questions
Top South Beach hotel deals

Southernmost Beach Resort and Guesthouses
1319 Duval Street, Key West, FL
Free Cancellation
$237 nightly
The price is $266 total per night
$266 total
Aug 24 - Aug 25
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
$274 nightly
The price is $308 total per night
$308 total
Sep 2 - Sep 3
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
$292 nightly
The price is $329 total per night
$329 total
Sep 7 - Sep 8
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
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.