Exclusive Robbie's Vacation Deals
Robbie's vacation package deals
Price found within the past 48 hours. Click for updated prices.
Oceans Edge Key West Resort, Hotel & Marina
Save 100% on your flight
Price was $1,307, price is now $802 per person
$802
per person
Dec 15 - Dec 22
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.
Winslow's Bungalows - Key West Historic Inns
Old Town Key West
Save 100% on your flight
Price was $1,980, price is now $1,158 per person
$1,158
per person
Dec 15 - Dec 22
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.
Lighthouse Hotel - Key West Historic Inns
Old Town Key West
Save 100% on your flight
Price was $1,905, price is now $1,125 per person
$1,125
per person
Dec 15 - Dec 22
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.
Ella's Cottages - Key West Historic Inns
Old Town Key West
Save 100% on your flight
Price was $1,506, price is now $923 per person
$923
per person
Nov 15 - Nov 19
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
An outdoor pool, self parking, and concierge services are featured at this hotel. 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.
Fitch Lodge - Key West Historic Inns
Key West Historic District
Save 100% on your flight
Price was $1,549, price is now $954 per person
$954
per person
Dec 15 - Dec 22
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
An outdoor pool is featured at this hotel, along with free WiFi in public areas and luggage storage. Enjoy the free on-the-go breakfast each morning. Concierge services are provided for your convenience.
Hyatt Vacation Club at Beach House, Key West
Save 100% on your flight
Price was $1,405, price is now $872 per person
$872
per person
Dec 1 - Dec 6
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.
Frequently asked questions
Top Robbie's hotel deals
Oceans Edge Key West Resort, Hotel & Marina
5950 Peninsular Avenue, Key West, FL
Free Cancellation
Reserve now, pay when you stay
$189 nightly
The price is $213 total per night
$213 total
Oct 13 - Oct 14
Total with 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
$165 nightly
The price is $186 total per night
$186 total
Oct 14 - Oct 15
Total with 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
DoubleTree Resort by Hilton Grand Key - Key West
3990 S Roosevelt Blvd, Key West, FL
Free Cancellation
Reserve now, pay when you stay
$165 nightly
The price is $186 total per night
$186 total
Oct 12 - Oct 13
Total with taxes and fees
This resort features a restaurant, an outdoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and free airport shuttle. Enjoy the 24-hour gym and perks like a free beach shuttle.
Pool
Free airport shuttle
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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