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

Oceans Edge Key West Resort, Hotel & Marina
Save 100% on your flight
Price was $834, price is now $551 per person
$551
per person
Oct 27 - Nov 1
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.

Hyatt Vacation Club at Windward Pointe, Key West
Save 100% on your flight
Price was $1,603, price is now $949 per person
$949
per person
Oct 18 - Oct 23
found 10 hours 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 Perry Hotel & Marina Key West
Save 100% on your flight
Price was $952, price is now $596 per person
$596
per person
Oct 27 - Nov 1
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.

Hyatt Vacation Club at Beach House, Key West
Save 100% on your flight
Price was $1,082, price is now $688 per person
$688
per person
Nov 16 - Nov 20
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) 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 self parking and free WiFi. A safe deposit box and concierge services are also provided.

Bishop Hotel Key West
Old Town Key West
Save 100% on your flight
Price was $1,434, price is now $961 per person
$961
per person
Oct 27 - Nov 1
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.

Douglas House
Old Town Key West
Save 100% on your flight
Price was $1,635, price is now $1,103 per person
$1,103
per person
Oct 27 - Nov 1
found 1 day ago
Roundtrip non-stop 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 terrace, a garden, and a picnic area are also on offer.
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
$184 nightly
The price is $207 total per night
$207 total
Sep 2 - Sep 3
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
$219 nightly
The price is $247 total per night
$247 total
Sep 2 - Sep 3
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

Hilton Garden Inn Key West / The Keys Collection
3850 N Roosevelt Blvd, Key West, FL
Free Cancellation
Reserve now, pay when you stay
$132 nightly
The price is $149 total per night
$149 total
Sep 2 - Sep 3
Total with taxes and fees
This smoke-free hotel includes 2 restaurants, an outdoor pool, and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Unwind with a drink at the bar/lounge and enjoy perks like a free area shuttle.
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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