
Exclusive Smathers Beach Vacation Deals
Smathers Beach vacation package deals
Price found within the past 48 hours. Click for updated prices.

Oceans Edge Key West Resort, Hotel & Marina
Price was $2,766, price is now $1,625 per person
$1,625
per person
Dec 23 - Dec 29
found 1 day ago
Roundtrip 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
Price was $3,242, price is now $1,745 per person
$1,745
per person
Dec 23 - Dec 29
found 1 day ago
Roundtrip 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
Price was $3,005, price is now $1,683 per person
$1,683
per person
Dec 23 - Dec 29
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 Key West Hotel
Key West Historic District
Price was $5,587, price is now $3,247 per person
$3,247
per person
Dec 23 - Dec 29
found 1 day ago
Roundtrip 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.

Southernmost House
Old Town Key West
Save 100% on your flight
Price was $4,130, price is now $2,405 per person
$2,405
per person
Nov 23 - Nov 30
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Unwind with a drink at the poolside bar and enjoy perks like free continental breakfast and free WiFi. Self parking, a terrace, and a garden are also offered.

Lighthouse Hotel - Key West Historic Inns
Old Town Key West
Price was $2,868, price is now $1,718 per person
$1,718
per person
Dec 23 - Dec 29
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
This hotel features an outdoor pool and a poolside bar. 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.
Frequently asked questions
Top Smathers Beach hotel deals

Margaritaville Beach House Key West
2001 South Roosevelt Boulevard, Key West, FL
Free Cancellation
Reserve now, pay when you stay
$235 nightly
The price is $264 total per night
$264 total
Nov 18 - Nov 19
Total with taxes and fees
This hotel features a restaurant, an outdoor pool, and a bar/lounge. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including food and water bowls. There's a 24-hour gym on site, and a 24-hour front desk and dry cleaning are also provided.
Pool
Pet friendly

Parrot Key Hotel & Villas
2801 N Roosevelt Blvd, Key West, FL
Free Cancellation
Reserve now, pay when you stay
$194 nightly
The price is $218 total per night
$218 total
Nov 16 - Nov 17
Total with taxes and fees
This smoke-free hotel features 4 outdoor pools, a gym, and a restaurant. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. Unwind with a drink at the bar/lounge and enjoy perks like a free beach shuttle.
Pool
Free WiFi

Fairfield Inn and Suites by Marriott Key West
2400 N Roosevelt Blvd, Key West, FL
Free Cancellation
Reserve now, pay when you stay
$135 nightly
The price is $152 total per night
$152 total
Oct 26 - Oct 27
Total with taxes and fees
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the 24-hour gym and free continental breakfast each morning.
Pool
Breakfast 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.
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