
Key Haven Vacations from $494
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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
Save 100% on your flight
per person
Oct 5 - Oct 10
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.6/10 Exceptional! (1,024 reviews)
We enjoyed our stay very much and will be staying here again in the near future. Everything about it was very nice with beautiful views of the property.
Reviewed on Aug 4, 2025


The Perry Hotel & Marina Key West
Save 100% on your flight
per person
Sep 5 - Sep 10
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.4/10 Exceptional! (1,044 reviews)
Great experience overall! Clean hotel and pool, great local food and convenient shuttle service to downtown Key West.
We did on site laundry… were told one price for a bag of clothing and were charged another, even though all items fit into their laundry bag and closed.
We had the mimosa package special upon booking and it was never delivered upon, they stated we would get that refunded to us.
Those were our only two complaints!
Reviewed on Aug 5, 2025

Southernmost Beach Resort and Guesthouses
Old Town Key West
Save 100% on your flight
per person
Sep 5 - Sep 10
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
8.6/10 Excellent! (2,611 reviews)
Life is not perfect however it’s the accommodations and customer service that makes the difference. I could share with you everything that was wrong but I would rather focus on the effort that Annette and Davoli made to make everything perfect!!!! Excellent customer service!!
The location is close to everything and the pool parties are a lot of fun! This is a great place to relax and have fun!!!
Anne Marie could benefit from additional customer service training.
FYI: The private beach is not clean or available for swimming.
Reviewed on Aug 5, 2025
Key Haven Hotel Deals

Beachside Resort & Residences
3841 N Roosevelt Blvd, Key West, FL
Fully refundableReserve now, pay when you stay
$194 nightly
The price is $218 total per night from Aug 11 to Aug 12
$218 total
Aug 11 - Aug 12
Total includes taxes and fees
8.4/10 Very Good! (1,416 reviews)
"The unit was very spacious which was perfect for a family. The view from our unit was spectacular."
Reviewed on Aug 2, 2025

Blue Flamingo Resort Key West
3820 North Roosevelt Boulevard, Key West, FL
Fully refundableReserve now, pay when you stay
$164 nightly
The price is $184 total per night from Sep 3 to Sep 4
$184 total
Sep 3 - Sep 4
Total includes taxes and fees
7.6/10 Good! (1,533 reviews)
"The staff and the manager are so nice I had a small issue with my room after the first night and the manager was so kind to move us to a new and gave us a 50.00 bar credit for the inconvenience he was very understanding about the issue and took care of it right away this property is family friendly ..."
Reviewed on Aug 4, 2025

Southernmost Beach Resort and Guesthouses
1319 Duval Street, Key West, FL
Fully refundable
$244 nightly
The price is $275 total per night from Aug 25 to Aug 26
$275 total
Aug 25 - Aug 26
Total includes taxes and fees
8.6/10 Excellent! (2,651 reviews)
"Great place, my wife and I love it!"
Reviewed on Aug 2, 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.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.