Exclusive Monday Key Vacation Deals
Monday Key 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 $1,112, price is now $801 per person
$801
per person
Jul 10 - Jul 13
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.
The Perry Hotel & Marina Key West
Save 100% on your flight
Price was $1,699, price is now $1,195 per person
$1,195
per person
Jun 4 - Jun 11
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 Sunset Harbor, Key West
Old Town Key West
Price was $1,832, price is now $1,313 per person
$1,313
per person
Jun 26 - Jun 29
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.
The Key West Hotel
Key West Historic District
Save 100% on your flight
Price was $2,383, price is now $1,726 per person
$1,726
per person
May 28 - Jun 2
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.
Hyatt Vacation Club at Windward Pointe, Key West
Price was $1,422, price is now $1,031 per person
$1,031
per person
Jun 26 - Jun 29
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.
Tropical Dreaming by Avantstay 4 Blks to Beach! Private Pool!
Old Town Key West
Save 100% on your flight
Price was $3,441, price is now $2,540 per person
$2,540
per person
Jun 7 - Jun 12
found 20 hours 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.
Top Monday Key hotel deals
Blue Flamingo Resort Key West
3820 North Roosevelt Boulevard Key West FL
Free Cancellation
Reserve now, pay when you stay
$211 nightly
The price is $238 total per night
$238 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
Beachside Resort & Residences
3841 N Roosevelt Blvd Key West FL
Free Cancellation
Reserve now, pay when you stay
$256 nightly
The price is $288 total per night
$288 total
May 11 - May 12
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
$262 nightly
The price is $294 total per night
$294 total
May 18 - May 19
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
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.