
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
Save 100% on your flight
Price was $1,657, price is now $1,082 per person
$1,082
per person
Jul 31 - Aug 4
found 1 day ago
Roundtrip non-stop 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.

Hyatt Vacation Club at Beach House, Key West
Price was $1,876, price is now $1,227 per person
$1,227
per person
Aug 9 - Aug 15
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 WiFi. Self parking, concierge services, and barbecue grills are also on offer.

Hyatt Vacation Club at Sunset Harbor, Key West
Old Town Key West
Save 100% on your flight
Price was $1,843, price is now $1,228 per person
$1,228
per person
Jul 31 - Aug 4
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. WiFi in public areas is free.

Coconut Beach Resort
Old Town Key West
Save 100% on your flight
Price was $2,047, price is now $1,392 per person
$1,392
per person
Aug 5 - Aug 11
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
A private beach and an outdoor pool are featured at this smoke-free resort. Enjoy the hot tub and perks like free self parking and free WiFi. A computer station, dry cleaning, and luggage storage are also on offer.

The Key West Hotel
Key West Historic District
Save 100% on your flight
Price was $1,857, price is now $1,285 per person
$1,285
per person
Jul 31 - Aug 4
found 1 day ago
Roundtrip non-stop 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.

Amelia Home by Avantstay In Historic Old Town w/ Pool
Old Town Key West
Save 100% on your flight
Price was $3,356, price is now $2,409 per person
$2,409
per person
Aug 16 - Aug 22
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
An outdoor pool is featured at this cottage, along with free WiFi in public areas and barbecue grills.
Frequently asked questions
Top Robbie's hotel deals

Blue Flamingo Resort Key West
3820 North Roosevelt Boulevard Key West FL
Free Cancellation
Reserve now, pay when you stay
$184 nightly
The price is $207 total per night
$207 total
May 26 - May 27
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

Oceans Edge Key West Resort, Hotel & Marina
5950 Peninsular Avenue Key West FL
Free Cancellation
Reserve now, pay when you stay
$251 nightly
The price is $283 total per night
$283 total
Jun 15 - Jun 16
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
$186 nightly
The price is $210 total per night
$210 total
May 26 - May 27
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
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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