
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 $1,070, price is now $614 per person
$614
per person
Jan 30 - Feb 2
found 1 day ago
Roundtrip 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
Save 100% on your flight
Price was $3,730, price is now $2,145 per person
$2,145
per person
Mar 5 - Mar 10
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.

Oceans Edge Key West Resort, Hotel & Marina
Save 100% on your flight
Price was $3,524, price is now $2,070 per person
$2,070
per person
Feb 6 - Feb 9
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.

Southernmost Beach Resort and Guesthouses
Old Town Key West
Save 100% on your flight
Price was $1,862, price is now $1,191 per person
$1,191
per person
Feb 6 - Feb 9
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.

The Perry Hotel & Marina Key West
Save 100% on your flight
Price was $1,647, price is now $1,130 per person
$1,130
per person
Feb 6 - Feb 9
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 Windward Pointe, Key West
Price was $1,604, price is now $1,109 per person
$1,109
per person
Mar 26 - Mar 29
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) 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.
Top Monday Key hotel deals

Beachside Resort & Residences
3841 N Roosevelt Blvd Key West FL
Free Cancellation
Reserve now, pay when you stay
$313 nightly
The price is $352 total per night
$352 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

The Fairhaven House at Solaire Lunara Bay
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.
Breakfast included
Parking included
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.