Key Haven Vacation Packages for 2026
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Key Haven Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Blue Flamingo Resort Key West
New Town
Save 100% on your flight
Price was $1,574, price is now $1,125 per person
$1,125
per person
Apr 28 - May 5
found 16 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
Book a stay at this family-friendly hotel in Key West. Enjoy free WiFi, 2 outdoor pools, and 2 restaurants. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Duval Street and Smathers Beach are located nearby.
The Key West Hotel
Key West Historic District
Save 100% on your flight
Price was $5,438, price is now $3,210 per person
$3,210
per person
Apr 28 - May 5
found 16 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
Stay at this guesthouse in Key West. Enjoy free WiFi, room service, and daily housekeeping. Popular attractions Duval Street and Mallory Square are located nearby.
Oceans Edge Key West Resort, Hotel & Marina
Save 100% on your flight
Price was $2,047, price is now $1,399 per person
$1,399
per person
Apr 28 - May 5
found 16 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
Book a stay at this luxury hotel in Key West. Enjoy free WiFi, 6 outdoor pools, and a marina. Our guests praise the pool and the restaurant in our reviews. Popular attractions Duval Street and Smathers Beach are located nearby.
Havana Cabana at Key West
New Town
Save 100% on your flight
Price was $1,986, price is now $1,388 per person
$1,388
per person
Apr 28 - May 5
found 16 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
Book a stay at this business-friendly hotel in Key West. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the pool and the helpful staff in our reviews. Popular attractions Duval Street and Smathers Beach are located nearby.
Lighthouse Hotel - Key West Historic Inns
Old Town Key West
Save 100% on your flight
Price was $2,978, price is now $2,106 per person
$2,106
per person
Apr 28 - May 5
found 16 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
Stay at this hotel in Key West. Enjoy free breakfast, free WiFi, and daily housekeeping. Our guests praise the helpful staff in our reviews. Popular attractions Duval Street and Ernest Hemingway Home and Museum are located nearby.
Southernmost Beach Resort and Guesthouses
Old Town Key West
Save 100% on your flight
Price was $2,627, price is now $1,890 per person
$1,890
per person
Apr 28 - May 5
found 16 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
Book a stay at this beach hotel in Key West. Enjoy free WiFi, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Duval Street and Southernmost Point are located nearby.
Top Hotel Deals
Southernmost Beach Resort and Guesthouses
1319 Duval Street Key West FL
7.37 km from Key Haven
Book a stay at this beach hotel in Key West. Enjoy free WiFi, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our ...
Ibis Bay Beach Resort
3101 N. Roosevelt Blvd Key West FL
3.98 km from Key Haven
Book a stay at this beach hotel in Key West. Enjoy free breakfast, free WiFi, and a private beach. Our guests praise the breakfast and the pool in our reviews. ...
Oceans Edge Key West Resort, Hotel & Marina
5950 Peninsular Avenue Key West FL
1.7 km from Key Haven
Book a stay at this luxury hotel in Key West. Enjoy free WiFi, 6 outdoor pools, and a marina. Our guests praise the pool and the restaurant in our reviews. Popular ...
Blue Flamingo Resort Key West
3820 North Roosevelt Boulevard Key West FL
2.49 km from Key Haven
Book a stay at this family-friendly hotel in Key West. Enjoy free WiFi, 2 outdoor pools, and 2 restaurants. Our guests praise the pool and the helpful staff ...
DoubleTree Resort by Hilton Grand Key - Key West
3990 S Roosevelt Blvd Key West FL
2.77 km from Key Haven
Book a stay at this business-friendly resort in Key West. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff ...
Havana Cabana at Key West
3420 N. Roosevelt Blvd Key West FL
3.18 km from Key Haven
Book a stay at this business-friendly hotel in Key West. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the pool and the helpful ...
Margaritaville Beach House Key West
2001 South Roosevelt Boulevard Key West FL
5.03 km from Key Haven
Book a stay at this beach hotel in Key West. Enjoy breakfast (surcharge), room service, and a 24-hour fitness center. Our guests praise the pool and the restaurant ...
Parrot Key Hotel & Villas
2801 N Roosevelt Blvd Key West FL
4.45 km from Key Haven
Book a stay at this beach hotel in Key West. Enjoy free WiFi, 4 outdoor pools, and breakfast (surcharge). Our guests praise the pool and the bar in our reviews. ...
Pier House Resort & Spa
1 Duval St Key West FL
7.82 km from Key Haven
Book a stay at this beach resort in Key West. Enjoy a full-service spa, a private beach, and 2 bars/lounges. Our guests praise the pool and the helpful staff ...
Casa Marina Key West, Curio Collection by Hilton
1500 Reynolds Street Key West FL
6.87 km from Key Haven
Book a stay at this beach resort in Key West. Enjoy 2 outdoor pools, a full-service spa, and a private beach. Popular attractions Duval Street and Southernmost ...
The Perry Hotel & Marina Key West
7001 Shrimp Road Key West FL
1.64 km from Key Haven
Book a stay at this business-friendly hotel in Key West. Enjoy free WiFi, 2 outdoor pools, and 2 restaurants. Our guests praise the pool and the helpful staff ...
Hyatt Vacation Club at Beach House, Key West
5051 Overseas Highway Key West FL
2.1 km from Key Haven
Stay at this hotel in Key West. Enjoy free WiFi, free parking, and concierge services. Our guests praise the helpful staff and the clean rooms in our reviews. ...
NYAH Key West - Adults Only
420 Margaret Street Key West FL
7.1 km from Key Haven
Stay at this guesthouse in Key West. Enjoy free breakfast, 3 outdoor pools, and a rooftop terrace. Our guests praise the pool and the helpful staff in our reviews. ...
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.
Top Flight Deals
These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.
Tue, Mar 3 - Tue, Mar 17
ORD
O'Hare Intl.
EYW
Key West Intl.
$177 Roundtrip, found 4 days ago
$177
Roundtrip
found 4 days ago
Thu, Mar 5 - Tue, Mar 10
BOS
Logan Intl.
EYW
Key West Intl.
$233 Roundtrip, found 3 days ago
$233
Roundtrip
found 3 days ago
Tue, Mar 3 - Wed, Mar 18
ORD
O'Hare Intl.
EYW
Key West Intl.
$329 Roundtrip, found 4 days ago
$329
Roundtrip
found 4 days ago
Thu, Mar 5 - Tue, Mar 10
BOS
Logan Intl.
EYW
Key West Intl.
$737 Roundtrip, found 3 days ago
$737
Roundtrip
found 3 days ago