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

NYAH Key West - Adults Only
Key West Historic District
per person
Jun 6 - Jun 9
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
This guesthouse's 3 outdoor pools and a rooftop terrace are among the featured amenities. Enjoy the hot tub and free continental breakfast each morning. There's a bar/lounge on site, and a 24-hour front desk and concierge services are also provided.

Southernmost Beach Resort
Old Town Key West
Save 100% on your flight
per person
Jun 9 - Jun 15
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.

Bishop Hotel Key West
Old Town Key West
Save 100% on your flight
per person
Jun 9 - Jun 15
found 1 day ago
Roundtrip non-stop 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.

Oceans Edge Key West Resort, Hotel & Marina
Save 100% on your flight
per person
Jun 9 - Jun 15
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.

The Perry Hotel & Marina Key West
Save 100% on your flight
per person
Jun 9 - Jun 15
found 1 day ago
Roundtrip non-stop 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.

Havana Cabana at Key West - Adults Only
New Town
Save 100% on your flight
per person
Jun 9 - Jun 15
found 1 day ago
Roundtrip non-stop 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.
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
The price is $265 per night
$265
includes taxes & fees
$236 per night
May 11 - May 12
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
The price is $286 per night
$286
includes taxes & fees
$254 per night
May 19 - May 20
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

Beachside Resort & Residences
3841 N Roosevelt Blvd, Key West, FL
Free Cancellation
Reserve now, pay when you stay
The price is $267 per night
$267
includes taxes & fees
$238 per night
May 6 - May 7
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
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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