
Exclusive Robbie's Vacation Deals
Robbie's 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.

Almond Tree Inn Hotel - Adults Only
Old Town Key West
Save 100% on your flight
per person
Sep 26 - Sep 30
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.

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.

The Reach 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)
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.

Southernmost Beach Resort and Guesthouses
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)
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 Robbie's hotel deals

Beachside Resort & Residences
3841 N Roosevelt Blvd, Key West, FL
Free Cancellation
Reserve now, pay when you stay
$202 nightly
The price is $227 total per night
$227 total
Jul 20 - Jul 21
Total includes taxes and fees
This smoke-free hotel features a private beach, a marina, and 2 restaurants. Enjoy a day at the beach kayaking, or relax with sun loungers. Unwind with a drink at one of the 2 bars/lounges and enjoy freebies like WiFi in public areas and an area shuttle.
On private beach
Pool

Oceans Edge Key West Resort, Hotel & Marina
5950 Peninsular Avenue, Key West, FL
Free Cancellation
Reserve now, pay when you stay
$224 nightly
The price is $251 total per night
$251 total
Aug 10 - Aug 11
Total includes taxes and fees
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.
Pool
Pet friendly

The Perry Hotel & Marina Key West
7001 Shrimp Road, Key West, FL
Free Cancellation
Reserve now, pay when you stay
$218 nightly
The price is $245 total per night
$245 total
Aug 12 - Aug 13
Total includes taxes and fees
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.
Pool
Pet friendly
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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