
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 Windward Pointe, Key West
Price was $1,774, price is now $1,238 per person
$1,238
per person
Apr 2 - Apr 6
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.

Oceans Edge Key West Resort, Hotel & Marina
Price was $2,768, price is now $1,797 per person
$1,797
per person
Mar 13 - Mar 19
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.

Southernmost Beach Resort and Guesthouses
Old Town Key West
Price was $3,021, price is now $2,102 per person
$2,102
per person
Mar 13 - Mar 19
found 1 day ago
Roundtrip 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 on business? Take advantage of the 2 conference rooms, along with dry cleaning/laundry services.

The Key West Hotel
Key West Historic District
Save 100% on your flight
Price was $2,801, price is now $1,987 per person
$1,987
per person
Mar 24 - Mar 28
found 2 days ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
An outdoor pool is featured at this guesthouse, along with free WiFi in public areas and a garden. Luggage storage and concierge services are also provided.

Ibis Bay Beach Resort
Northside Resort
Price was $1,975, price is now $1,411 per person
$1,411
per person
Mar 13 - Mar 19
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
This Art Deco hotel features a private beach, a marina, and a restaurant. Enjoy a day at the beach kayaking, or relax with sun loungers. Enjoy the outdoor pool and free perks like continental breakfast and WiFi in public areas.

Blue Flamingo Resort Key West
New Town
Price was $2,097, price is now $1,500 per person
$1,500
per person
Mar 13 - Mar 19
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
This hotel features 2 restaurants, 2 outdoor pools, and a 24-hour gym. There's fun for all ages with mini golf and an arcade/game room, and families will appreciate the picnic area. Unwind with a drink at one of the 2 poolside bars and enjoy freebies like WiFi in public areas and an area shuttle.
Frequently asked questions
Top South Beach hotel deals

Southernmost Beach Resort and Guesthouses
1319 Duval Street Key West FL
Free Cancellation
$579 nightly
The price is $651 total per night
$651 total
Mar 10 - Mar 11
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 on business? Take advantage of the 2 conference rooms, along with dry cleaning/laundry services.
Pool
Spa

The Reach Key West, Curio Collection by Hilton
1435 Simonton Street Key West FL
Free Cancellation
Reserve now, pay when you stay
$539 nightly
The price is $606 total per night
$606 total
Feb 11 - Feb 12
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

The Southernmost Inn - Adults Only
525 United Street Key West FL
Free Cancellation
Reserve now, pay when you stay
$489 nightly
The price is $550 total per night
$550 total
Mar 11 - Mar 12
Total with taxes and fees
This hotel's 2 outdoor pools and hot tub are among the featured amenities. Enjoy the free continental breakfast each morning. Self parking, a coffee shop, and a terrace are also offered.
Pool
Hot Tub
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.
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