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.
Paradise Inn Key West - Adults Only
Old Town Key West
$1,447
per person
Dec 23 - Dec 27
found 7 hours ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Key West (EYW)
Book a stay at this business-friendly hotel in Key West. Enjoy free breakfast, parking (surcharge), and a garden. Our guests praise the breakfast and the pool in our reviews. Popular attractions Duval Street and Ernest Hemingway Home and Museum are located nearby.
Very cute and clean property. The only thing I didn’t like was the fee for parking our rented golf cart in property.
Reviewed on Sep 30, 2026
The Key West Hotel
Key West Historic District
$2,504
per person
Nov 23 - Nov 30
found 1 day ago
Roundtrip non-stop flight included
Pittsburgh (PIT) 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.
The Marker Key West Harbor Resort
Key West Historic District
$1,856
per person
Dec 21 - Dec 26
found 15 hours ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
Book a stay at this business-friendly hotel in Key West. Enjoy free WiFi, 3 outdoor pools, and breakfast (surcharge). Our guests praise the pool and the helpful staff in our reviews. Popular attractions Duval Street and Mallory Square are located nearby.
The Gardens Hotel
Old Town Key West
$2,447
per person
Nov 23 - Nov 30
found 1 day ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Key West (EYW)
Book a stay at this business-friendly B&B in Key West. Enjoy free breakfast, free WiFi, and 2 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Duval Street and Ernest Hemingway Home and Museum are located nearby.
It is a GREAT property in Key West, right in the center of the action.
Reviewed on Sep 28, 2026
Hyatt Vacation Club at Sunset Harbor, Key West
Old Town Key West
$2,058
per person
Dec 21 - Dec 26
found 15 hours ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
Stay at this hotel in Key West. Enjoy free WiFi, parking (surcharge), and concierge services. Popular attractions Duval Street and Mallory Square are located nearby.
Amsterdam's Curry Mansion Inn
Key West Historic District
$1,517
per person
Nov 23 - Nov 30
found 1 day ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Key West (EYW)
Book a stay at this historic guesthouse in Key West. Enjoy free WiFi, beach cabanas (surcharge), and a business center. Our guests praise the pool and the clean rooms in our reviews. Popular attractions Duval Street and Mallory Square are located nearby.
Top Hotel Deals
Blue Flamingo Resort Key West
3820 North Roosevelt Boulevard Key West FL
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 ...
Southernmost Beach Resort and Guesthouses
1319 Duval Street Key West FL
Book a stay at this spa 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 ...
Margaritaville Beach House Key West
2001 South Roosevelt Blvd Key West FL
Book a stay at this beach hotel in Key West. Enjoy breakfast (surcharge), a free airport shuttle, and room service. Our guests praise the pool and the restaurant ...
Ibis Bay Beach Resort
3101 N. Roosevelt Blvd Key West FL
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. ...
Havana Cabana at Key West
3420 N. Roosevelt Blvd Key West FL
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 ...
Pier House Resort & Spa
1 Duval St Key West FL
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 ...
Beachside Resort & Residences
3841 N Roosevelt Blvd Key West FL
Book a stay at this beach hotel in Key West. Enjoy free WiFi, 2 restaurants, and a private beach. Our guests praise the pool and the helpful staff in our reviews. ...
Casa Marina Key West, Curio Collection by Hilton
1500 Reynolds Street Key West FL
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 South Beach ...
DoubleTree Resort by Hilton Grand Key - Key West
3990 S Roosevelt Blvd Key West FL
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 ...
Hilton Garden Inn Key West / The Keys Collection
3850 N Roosevelt Blvd Key West FL
Book a stay at this business-friendly hotel in Key West. Enjoy 2 restaurants, breakfast (surcharge), and a free area shuttle. Our guests praise the pool and ...
Hyatt Centric Key West Resort and Spa
601 Front St Key West FL
Book a stay at this beach resort in Key West. Enjoy free WiFi, a full-service spa, and a marina. Our guests praise the pool and the helpful staff in our reviews. ...
La Concha Key West, Autograph Collection
430 Duval St Key West FL
Book a stay at this business-friendly hotel in Key West. Enjoy free WiFi, 3 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
Hampton Inn Key West FL
3755 S Roosevelt Blvd Key West FL
Book a stay at this business-friendly hotel in Key West. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the breakfast and the ...
Parrot Key Hotel & Villas
2801 N Roosevelt Blvd Key West FL
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. ...
The Perry Hotel & Marina Key West
7001 Shrimp Road Key West FL
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 ...
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, Jan 26 - Fri, Jan 29
TPA
Tampa Intl.
EYW
Key West Intl.
$154
Roundtrip
found 4 days ago
Mon, Nov 16 - Thu, Nov 26
EWR
Newark Liberty Intl. Airport
EYW
Key West Intl.
$339
Roundtrip
found 1 day ago
Fri, Dec 11 - Thu, Dec 17
ATL
Hartsfield-Jackson Atlanta Intl.
EYW
Key West Intl.
$349
Roundtrip
found 14 hours ago
Sat, Nov 7 - Thu, Nov 12
BWI
Baltimore Washington Intl. Thurgood Marshall
EYW
Key West Intl.
$351
Roundtrip
found 1 day ago
Sun, Oct 18 - Thu, Oct 22
BOS
Logan Intl.
EYW
Key West Intl.
$427
Roundtrip
found 2 days ago
Best points of interest in Key West
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