
Exclusive Key West Express Vacation Deals

Key West Express vacation package deals
Price found within the past 48 hours. Click for updated prices.

GreenLinks Golf Villas at Lely Resort
Save 100% on your flight
Price was $892, price is now $582 per person
$582
per person
Jan 5 - Jan 9
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
A golf course, a full-service spa, and 2 outdoor tennis courts are all featured at this smoke-free aparthotel. Enjoy the outdoor pool and perks like free self parking. There's a restaurant and a bar/lounge for dining and drinks, and also a gym on site.

LaPlaya Beach & Golf Resort - A Noble House Resort
Vanderbilt Beach
Save 100% on your flight
Price was $1,126, price is now $617 per person
$617
per person
Dec 11 - Dec 14
found 2 days ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
This luxury resort features a private beach, a full-service spa, and 2 restaurants. Relax with sun loungers and beach umbrellas, and cool off with a drink at the beachside bar. Enjoy the outdoor pool and visit the 2 bars/lounges and beach bar for drinks.

Edison Beach House
Save 100% on your flight
Price was $1,830, price is now $1,117 per person
$1,117
per person
Dec 29 - Jan 2
found 1 hour ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
An outdoor pool, free self parking, and free newspapers are featured at this aparthotel. A terrace, a garden, and a picnic area are also on offer.

The Perry Hotel Naples
Save 100% on your flight
Price was $2,584, price is now $1,611 per person
$1,611
per person
Dec 30 - Jan 4
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
A marina, 2 restaurants, and 2 outdoor pools are all featured at this smoke-free hotel. Unwind with a drink at one of the 2 poolside bars and enjoy freebies like WiFi in public areas and a beach shuttle. Relax with a drink at one of the 2 bars/lounges and enjoy the a rooftop terrace.

Innovation Hotel
Save 100% on your flight
Price was $1,885, price is now $1,180 per person
$1,180
per person
Dec 30 - Jan 4
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
This smoke-free hotel features 2 restaurants, 2 outdoor tennis courts, and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Relax with a drink at the bar/lounge and enjoy free perks like buffet breakfast and free self parking.

Matanzas Inn Bayside Resort and Marina
Price was $1,600, price is now $1,056 per person
$1,056
per person
Dec 30 - Jan 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Enjoy the hot tub and perks like free self parking and free WiFi. A terrace, a picnic area, and luggage storage are also on offer.
Top Key West Express hotel deals

Margaritaville Beach Resort Fort Myers
251 Crescent Street, Fort Myers Beach, FL
$204 nightly
The price is $228 total per night
$228 total
Nov 3 - Nov 4
Total with taxes and fees
A full-service spa, 4 restaurants, and an outdoor pool are all featured at this smoke-free hotel. Relax with a drink at one of the 4 bars/lounges and get perks like free WiFi. You'll appreciate the 24-hour gym, beach bar, and concierge services.
Pool
Spa

Lani Kai Beachfront Resort
1400 Estero Blvd, Fort Myers Beach, FL
$184 nightly
The price is $206 total per night
$206 total
Oct 29 - Oct 30
Total with taxes and fees
This hotel features 2 beach bars, a bar/lounge, and a restaurant. Enjoy the outdoor pool and perks like free WiFi. There's a poolside bar on site, and a 24-hour front desk and laundry facilities are also provided.
Pool
Free WiFi

DiamondHead Beach Resort
2000 Estero Blvd, Fort Myers Beach, FL
$185 nightly
The price is $207 total per night
$207 total
Nov 3 - Nov 4
Total with taxes and fees
This smoke-free resort features 2 hot tubs, an outdoor pool, and a restaurant. Dine at the beachfront restaurant and relax with beach umbrellas. Enjoy the gym and perks like free self parking and free WiFi.
Pool
Hot Tub
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View all propertiesLowest 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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