
Exclusive Robbie's Vacation Deals

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

Winslow's Bungalows - Key West Historic Inns
Old Town Key West
Price was $1,406, price is now $1,040 per person
$1,040
per person
Jul 22 - Jul 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.

Brisa Del Mar by Avantstay Communal Pool Gated Community Ocean Front
Save 100% on your flight
Price was $3,441, price is now $2,433 per person
$2,433
per person
Jul 16 - Jul 23
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
An outdoor pool is featured at this cottage, along with free WiFi in public areas.

The Key West Hotel
Key West Historic District
Save 100% on your flight
Price was $2,266, price is now $1,609 per person
$1,609
per person
Jul 22 - Jul 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.

The Gardens Hotel
Old Town Key West
Save 100% on your flight
Price was $1,979, price is now $1,461 per person
$1,461
per person
Jul 22 - Jul 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.

Southernmost Beach Resort and Guesthouses
Old Town Key West
Save 100% on your flight
Price was $1,574, price is now $1,169 per person
$1,169
per person
Jul 17 - Jul 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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 on business? Take advantage of the 2 conference rooms, along with dry cleaning/laundry services.

Duval Breeze by Avantstay Great Location Close to Beach & Nightlife Shared Pool! Week Long Stays
Old Town Key West
Save 100% on your flight
Price was $3,795, price is now $2,822 per person
$2,822
per person
Jul 25 - Aug 1
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
This cottage doesn't skimp on freebies - guests receive free WiFi and free self parking. An outdoor pool is also provided.
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
$203 nightly
The price is $228 total per night
$228 total
Jun 11 - Jun 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

Oceans Edge Key West Resort, Hotel & Marina
5950 Peninsular Avenue Key West FL
Free Cancellation
Reserve now, pay when you stay
$252 nightly
The price is $284 total per night
$284 total
Jun 7 - Jun 8
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
$244 nightly
The price is $274 total per night
$274 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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