
Key Haven Vacations from $663
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $1,045 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
The Latest Key Haven Vacation Packages
Price found within the past 48 hours. Click for updated prices.

Hyatt Vacation Club at Windward Pointe, Key West
Price was $1,319, price is now $663 per person
$663
per person
Jan 8 - Jan 12
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
9.6/10 Exceptional! (1,002 reviews)
The villa is just great! This property is 10/10.
Reviewed on Dec 1, 2025

Oceans Edge Key West Resort, Hotel & Marina
Save 100% on your flight
Price was $1,598, price is now $840 per person
$840
per person
Feb 5 - Feb 8
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9/10 Wonderful! (1,736 reviews)
Had hoped for something in room or on door for a 60th birthday I pre-wrote about at booking but nothing. The resort was nice but didn’t have great view or privacy on first floor. Having bikes & kayaks available is a very nice perk. Renting a scooter for the 4days made it easy to get to Duval St. We didn’t use the resort transportation. I stumbled upon yoga at pool once but it was almost over. Instructor was good. More activities throughout the day and night would be great. It would be helpful if resort informed Expedia/all guests a week before arrival of amenity options details and price. I booked a scooter on my own from home and felt I overpaid by 100. but didn’t know the concierge could’ve arranged and for less. Planning starts at booking not arrival. Both years stays room booked wasn’t ready on arrival so I settled for another one ready now but not what I wanted. Going on a boat even once would’ve made stay special. Even a meet n greet daily 3p or 4p boat ride for 30min would make your place on the water really special to stay at. Friendly staff and clean modern rooms.
Reviewed on Dec 1, 2025

Hyatt Vacation Club at Beach House, Key West
Save 100% on your flight
Price was $1,619, price is now $855 per person
$855
per person
Jan 25 - Jan 30
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.4/10 Exceptional! (1,002 reviews)
Todo muy bueno y lindo y muy tranquilo perfectas vacaciones
Reviewed on Nov 29, 2025

The Key West Hotel
Key West Historic District
Save 100% on your flight
Price was $2,674, price is now $1,512 per person
$1,512
per person
Feb 5 - Feb 8
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.2/10 Wonderful! (505 reviews)
Beautiful private oasis
Reviewed on Nov 25, 2025

The Perry Hotel & Marina Key West
Save 100% on your flight
Price was $1,214, price is now $697 per person
$697
per person
Feb 5 - Feb 8
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.4/10 Exceptional! (1,151 reviews)
The property was nice. The shuttle to key west was great. The bed in the room was terrible hard as a rock. Needs to be updated. And the chairs on the balcony were not comfortable at all. Other than that we really enjoyed our time here.
Reviewed on Nov 30, 2025
Where to stay in Key Haven
Find the best Key Haven areas and neighborhoods for the activities you enjoy most. Learn more about Key Haven

Old Town Key West
4 out of top 10 points of interest in this area
Old Town, the historic heart of Key West, boasts a central business district and numerous tourist attractions. Explore the Key West Aquarium, Ernest Hemingway House, Mallory Square, and more in this vibrant area.
Key Haven Hotel Deals

Beachside Resort & Residences
3841 N Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
$202 nightly
The price is $228 total per night from Dec 16 to Dec 17
$228 total
Dec 16 - Dec 17
Total with taxes and fees
8.6/10 Excellent! (1,720 reviews)
Great room, restaurant, and shuttle!
Reviewed on Nov 26, 2025

Blue Flamingo Resort Key West
3820 North Roosevelt Boulevard Key West FL
Fully refundableReserve now, pay when you stay
$151 nightly
The price is $170 total per night from Dec 4 to Dec 5
$170 total
Dec 4 - Dec 5
Total with taxes and fees
7.8/10 Good! (1,730 reviews)
Everything was beautiful and it was a pleasure to stay there. Will stay again.
Reviewed on Nov 25, 2025

Oceans Edge Key West Resort, Hotel & Marina
5950 Peninsular Avenue Key West FL
Fully refundableReserve now, pay when you stay
$203 nightly
The price is $228 total per night from Dec 2 to Dec 3
$228 total
Dec 2 - Dec 3
Total with taxes and fees
8.8/10 Excellent! (1,748 reviews)
The property was beautiful. The staff was welcoming and helpful. The room and accommodations were wonderful. Enjoyed the convenience of the concierge services as well as the shuttle. Everyone from the bellmen Sam to the shuttle drivers were friendly and made the time spent on property a joy.
Reviewed on Nov 25, 2025
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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.























