Exclusive Monday Key Vacation Deals
Monday Key vacation package deals
Price found within the past 48 hours. Click for updated prices.
Hyatt Vacation Club at Beach House, Key West
Save 100% on your flight
Price was $1,484, price is now $867 per person
$867
per person
Feb 1 - Feb 5
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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.
The Key West Hotel
Key West Historic District
Price was $2,574, price is now $1,391 per person
$1,391
per person
Feb 1 - Feb 5
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
Save 100% on your flight
Price was $1,518, price is now $885 per person
$885
per person
Feb 1 - Feb 5
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.
Oceans Edge Key West Resort, Hotel & Marina
Save 100% on your flight
Price was $1,760, price is now $1,084 per person
$1,084
per person
Feb 1 - Feb 5
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.
Ella's Cottages - Key West Historic Inns
Old Town Key West
Save 100% on your flight
Price was $2,023, price is now $1,293 per person
$1,293
per person
Feb 1 - Feb 5
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. Guests will appreciate free perks like continental breakfast and WiFi in public areas. A terrace, a garden, and a picnic area are also on offer.
Winslow's Bungalows - Key West Historic Inns
Old Town Key West
Save 100% on your flight
Price was $1,600, price is now $1,033 per person
$1,033
per person
Feb 1 - Feb 5
found 1 day ago
Roundtrip non-stop 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.
Top Monday Key hotel deals
Beachside Resort & Residences
3841 N Roosevelt Blvd Key West FL
Free Cancellation
Reserve now, pay when you stay
$295 nightly
The price is $331 total per night
$331 total
Jan 4 - Jan 5, 2026
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
$292 nightly
The price is $328 total per night
$328 total
Jan 26 - Jan 27, 2026
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
Parking Pool Dock - Shellstone House
Key West FL
$2,970 nightly
The price is $3,341 total per night
$3,341 total
Jan 12 - Jan 13, 2026
Total with taxes and fees
This vacation home doesn't skimp on freebies - guests receive free WiFi and free self parking. A garden and barbecue grills are also provided.
Parking included
Free WiFi
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.