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.
The Marker Key West Harbor Resort
Key West Historic District
Price was $1,765, price is now $1,354 per person
$1,354
per person
Dec 19 - Dec 23
found 1 day ago
Roundtrip flight included
Charlotte (CLT) 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.
Really nice boutique hotel with a great location, delicious food, pleasant service and lovely pool area. Will definitely return and recommend to others.
Reviewed on Nov 3, 2026
The Key West Hotel
Key West Historic District
Save 100% on your flight
Price was $3,899, price is now $2,479 per person
$2,479
per person
Jan 19 - Jan 24
found 24 hours ago
Roundtrip non-stop flight included
Indianapolis (IND) 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.
Clean, clean, clean. Hidden! Elite Backyard Oasis. Top Tier bar and fantastic nightly entertainment. If your traveling with anyone under 25, choose different. Will be back, no doubt!
Reviewed on Oct 29, 2026
Casita de Catherine by Avantstay 1 Block to Duval St w/ Hot Tub!
Old Town Key West
Price was $2,841, price is now $2,143 per person
$2,143
per person
Jan 20 - Jan 25
found 1 day ago
Roundtrip non-stop flight included
Indianapolis (IND) to Key West (EYW)
Stay at this cottage in Key West. Enjoy a beach locale, patios, and in-room washers/dryers. Popular attractions Duval Street and Southernmost Point are located nearby.
The Gardens Hotel
Old Town Key West
Price was $2,480, price is now $1,915 per person
$1,915
per person
Dec 19 - Dec 23
found 1 day ago
Roundtrip flight included
Charlotte (CLT) 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.
Best place we have stayed. The staff was amazing location perfect and the room was perfect
Reviewed on Nov 3, 2026
Orchid Key Inn - Adults Only
Old Town Key West
Price was $1,883, price is now $1,474 per person
$1,474
per person
Dec 19 - Dec 23
found 1 day ago
Roundtrip flight included
Charlotte (CLT) to Key West (EYW)
Stay at this hotel in Key West. Enjoy free breakfast, parking (surcharge), and a 24-hour front desk. Our guests praise the breakfast and the pool in our reviews. Popular attractions Duval Street and Mallory Square are located nearby.
Wonderful experience!
Great staff
Awesome location!
Amazing pool and hot tub!
On site bar..!
Reviewed on Nov 3, 2026
Duval Breeze by Avantstay Great Location Close to Beach & Nightlife Shared Pool! Week Long Stays
Old Town Key West
Price was $2,758, price is now $2,175 per person
$2,175
per person
Dec 19 - Dec 23
found 1 day ago
Roundtrip flight included
Charlotte (CLT) to Key West (EYW)
Stay at this cottage in Key West. Enjoy free parking, balconies, and in-room washers/dryers. Popular attractions Duval Street and Mallory Square are located nearby.
Location, comfort and great customer service! A great place for a family to stay and share in some fun together!!
Reviewed on Jul 26, 2026
Top Hotel Deals
Margaritaville Beach House Key West
2001 South Roosevelt Blvd Key West FL
5.06 km from city center
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 ...
Havana Cabana at Key West
3420 N. Roosevelt Blvd Key West FL
3.05 km from city center
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 ...
Blue Flamingo Resort Key West
3820 North Roosevelt Boulevard Key West FL
2.4 km from city center
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 ...
Beachside Resort & Residences
3841 N Roosevelt Blvd Key West FL
2.25 km from city center
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. ...
Ibis Bay Beach Resort
3101 N. Roosevelt Blvd Key West FL
3.86 km from city center
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. ...
Casa Marina Key West, Curio Collection by Hilton
1500 Reynolds Street Key West FL
6.83 km from city center
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
2.87 km from city center
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 ...
Southernmost Beach Resort and Guesthouses
1319 Duval Street Key West FL
7.32 km from city center
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 ...
Hilton Garden Inn Key West / The Keys Collection
3850 N Roosevelt Blvd Key West FL
2.32 km from city center
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 ...
Parrot Key Hotel & Villas
2801 N Roosevelt Blvd Key West FL
4.34 km from city center
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 Southernmost Inn - Adults Only
525 United Street Key West FL
7.28 km from city center
Stay at this hotel in Key West. Enjoy free breakfast, 2 outdoor pools, and parking (surcharge). Our guests praise the breakfast and the pool in our reviews. ...
Fairfield by Marriott Inn & Suites Key West at The Keys Collection
3852 North Roosevelt Boulevard Key West FL
2.35 km from city center
Book a stay at this business-friendly hotel in Key West. Enjoy free breakfast, free parking, and a fitness center. Our guests praise the breakfast and the pool ...
Hilton Key West Resort & Marina
5950 Peninsular Avenue Key West FL
2.07 km from city center
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 ...
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.
Mon, Dec 7 - Wed, Dec 9
CLT
Charlotte-Douglas Intl.
EYW
Key West Intl.
$167 Roundtrip, found 6 days ago
$167
Roundtrip
found 6 days ago
Tue, Dec 1 - Sat, Dec 5
CLT
Charlotte-Douglas Intl.
EYW
Key West Intl.
$402 Roundtrip, found 6 days ago
$402
Roundtrip
found 6 days ago
Sat, Feb 6 - Sat, Feb 13
PHL
Philadelphia Intl.
EYW
Key West Intl.
$513 Roundtrip, found 5 days ago
$513
Roundtrip
found 5 days ago
Wed, Dec 30 - Mon, Jan 4
PHL
Philadelphia Intl.
EYW
Key West Intl.
$895 Roundtrip, found 4 days ago
$895
Roundtrip
found 4 days ago