
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 $1,201, price is now $769 per person
$769
per person
Mar 22 - Mar 25
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.

The Key West Hotel
Key West Historic District
Save 100% on your flight
Price was $3,283, price is now $1,939 per person
$1,939
per person
Mar 18 - Mar 23
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.

Winslow's Bungalows - Key West Historic Inns
Old Town Key West
Save 100% on your flight
Price was $2,240, price is now $1,341 per person
$1,341
per person
Mar 18 - Mar 23
found 1 day ago
Roundtrip 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.

Oceans Edge Key West Resort, Hotel & Marina
Price was $3,361, price is now $2,084 per person
$2,084
per person
Feb 21 - Feb 28
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.

Southernmost Beach Resort and Guesthouses
Old Town Key West
Price was $3,703, price is now $2,435 per person
$2,435
per person
Feb 21 - Feb 28
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.

Pier House Resort & Spa
Key West Historic District
Save 100% on your flight
Price was $3,089, price is now $2,112 per person
$2,112
per person
Mar 18 - Mar 23
found 1 day ago
Roundtrip 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.
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
$306 nightly
The price is $344 total per night
$344 total
Jan 13 - Jan 14
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

Oceans Edge Key West Resort, Hotel & Marina
5950 Peninsular Avenue Key West FL
Free Cancellation
Reserve now, pay when you stay
$308 nightly
The price is $346 total per night
$346 total
Jan 13 - Jan 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
$383 nightly
The price is $431 total per night
$431 total
Jan 13 - Jan 14
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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