
Exclusive Robbie's Vacation Deals

Robbie's vacation package deals
Price found within the past 48 hours. Click for updated prices.

Blue Flamingo Resort Key West
New Town
Save 100% on your flight
Price was $1,785, price is now $1,192 per person
$1,192
per person
Mar 21 - Mar 28
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.

Havana Cabana at Key West
New Town
Save 100% on your flight
Price was $2,199, price is now $1,351 per person
$1,351
per person
Mar 21 - Mar 28
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Business travelers can take advantage of the free WiFi in public areas. Enjoy the hot tub and perks like free self parking.

Ibis Bay Beach Resort
Northside Resort
Save 100% on your flight
Price was $2,060, price is now $1,303 per person
$1,303
per person
Mar 21 - Mar 28
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.

The Key West Hotel
Key West Historic District
Save 100% on your flight
Price was $6,860, price is now $4,466 per person
$4,466
per person
Mar 21 - Mar 28
found 1 day 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.

Pier House Resort & Spa
Key West Historic District
Save 100% on your flight
Price was $3,709, price is now $2,424 per person
$2,424
per person
Apr 29 - May 3
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
This smoke-free resort features a private beach, a full-service spa, and a restaurant. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. Traveling on business? Take advantage of the 2 conference rooms, business center, and express check-in.

Bishop Hotel Key West
Old Town Key West
Save 100% on your flight
Price was $2,438, price is now $1,621 per person
$1,621
per person
Mar 21 - Mar 28
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
This guesthouse's 2 outdoor pools and hot tub are among the featured amenities. Unwind with a drink at the poolside bar and enjoy perks like free continental breakfast and free WiFi. There's luggage storage and multilingual staff can provide around-the-clock assistance.
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
$406 nightly
The price is $456 total per night
$456 total
Mar 12 - Mar 13
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
$434 nightly
The price is $488 total per night
$488 total
Mar 1 - Mar 2
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
$429 nightly
The price is $483 total per night
$483 total
Feb 11 - Feb 12
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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