
Exclusive Robbie's Vacation Deals

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

Paradise Inn Key West - Adults Only
Old Town Key West
Price was $1,330, price is now $973 per person
$973
per person
Dec 13 - Dec 18
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
This hotel features an outdoor pool and a hot tub. Enjoy the free self-serve breakfast each morning. Self parking, a terrace, and a garden are also offered.

The Key West Hotel
Key West Historic District
Save 100% on your flight
Price was $3,295, price is now $2,126 per person
$2,126
per person
Nov 24 - Nov 30
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.

Kona Kai Oasis
Old Town Key West
Save 100% on your flight
Price was $1,605, price is now $1,139 per person
$1,139
per person
Nov 24 - Nov 30
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
An outdoor pool, free self parking, and concierge services are featured at this guesthouse. WiFi in public areas is free. A garden, a picnic area, and luggage storage are also on offer.

The Perry Hotel & Marina Key West
Save 100% on your flight
Price was $1,729, price is now $1,230 per person
$1,230
per person
Nov 24 - Nov 30
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
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.

The Gardens Hotel
Old Town Key West
Save 100% on your flight
Price was $2,241, price is now $1,610 per person
$1,610
per person
Dec 13 - Dec 18
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
2 outdoor pools, 2 bars/lounges, and a restaurant are among this bed & breakfast's featured amenities. Business travelers can take advantage of the free WiFi in public areas. Relax with a drink at the poolside bar and enjoy the free cooked-to-order breakfast each morning.

Orchid Key Inn - Adults Only
Old Town Key West
Price was $1,560, price is now $1,152 per person
$1,152
per person
Dec 13 - Dec 18
found 1 day ago
Roundtrip 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 continental breakfast each morning. Self parking, a garden, and dry cleaning are also offered.
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
$185 nightly
The price is $208 total per night
$208 total
Oct 8 - Oct 9
Total with 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

Blue Flamingo Resort Key West
3820 North Roosevelt Boulevard Key West FL
Free Cancellation
Reserve now, pay when you stay
$168 nightly
The price is $189 total per night
$189 total
Oct 11 - Oct 12
Total with taxes and fees
This hotel features 2 restaurants, 2 outdoor pools, and a 24-hour gym. There's fun for all ages with mini golf and a playground, 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.
Pool
Hot Tub

Hilton Key West Resort & Marina
5950 Peninsular Avenue Key West FL
$172 nightly
The price is $194 total per night
$194 total
Oct 15 - Oct 16
Total with taxes and fees
A marina, 6 outdoor pools, and a 24-hour gym are all featured at this smoke-free hotel. Traveling on business? Take advantage of the free WiFi in public areas and Internet in public areas. The restaurant provides options for dining, while the bar/lounge and poolside bar are great spots to unwind.
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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