
Key Haven Vacations from $768
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The Latest Key Haven Vacation Packages
Price found within the past 48 hours. Click for updated prices.

Fitch Lodge - Key West Historic Inns
Key West Historic District
Save 100% on your flight
Price was $1,131, price is now $768 per person
$768
per person
Dec 15 - Dec 20
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
8.8/10 Excellent! (484 reviews)
Clean room. Friendly.
Reviewed on Oct 13, 2025

Winslow's Bungalows - Key West Historic Inns
Old Town Key West
Save 100% on your flight
Price was $1,553, price is now $951 per person
$951
per person
Dec 3 - Dec 7
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.2/10 Wonderful! (1,005 reviews)
Clean rooms and property. The grounds were so clean and taken care of. The landscape was so lush and exquisite. I loved everything about this property. Will be back.
Reviewed on Oct 13, 2025

Oceans Edge Key West Resort, Hotel & Marina
Save 100% on your flight
Price was $2,130, price is now $1,430 per person
$1,430
per person
Dec 24 - Dec 28
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
9/10 Wonderful! (1,722 reviews)
Staff was friendly and accommodating. The concierge booked trips for us and made some great recommendations for us.
Reviewed on Oct 8, 2025

The Key West Hotel
Key West Historic District
Save 100% on your flight
Price was $5,581, price is now $3,854 per person
$3,854
per person
Dec 24 - Dec 28
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
9.2/10 Wonderful! (496 reviews)
My wife and I have come to KeyWest for years, this by far the nicest and affordable with great music and staff. It's our new go to place!
Reviewed on Oct 3, 2025

Ella's Cottages - Key West Historic Inns
Old Town Key West
Save 100% on your flight
Price was $2,060, price is now $1,429 per person
$1,429
per person
Dec 24 - Dec 28
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
9.4/10 Exceptional! (375 reviews)
We really enjoyed our stay at Ella’s Cottages. It is a short walk to Duvall Street with lots of dining options close by. The suites were tucked into a beautifully landscaped property. I truly felt transported to a tropical island sanctuary. There were beach/pool towels on the lounge chairs by the pool. The pool itself is small but very clean and refreshing after a hot day. There were also tables in the pool area to dine or gather.
We upgraded our room to a larger room with a patio. The bathroom was nicely updated and very clean. Our bedroom area also was nicely updated and clean. The window AC unit worked hard to cool our room on the lowest setting. The ceiling fan helped.
The staff was very friendly and helped us find good suggestions of places to eat.
The continental breakfast was: essentially it’s a basket of croissants or bagels, bottled orange juice, yogurt cups, coffee, cheese packets, detox shots and two egg bites.
I would highly recommend Ella’s Cottages and would stay here again.
Reviewed on Sep 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
3 out of top 10 points of interest in this area
4.5/5(226 area reviews)
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

Oceans Edge Key West Resort, Hotel & Marina
5950 Peninsular Avenue, Key West, FL
Fully refundableReserve now, pay when you stay
$189 nightly
The price is $212 total per night from Oct 28 to Oct 29
$212 total
Oct 28 - Oct 29
Total with taxes and fees
8.8/10 Excellent! (1,728 reviews)
"Exceeded our expectations. Restaurant was amazing, everything was clean and up to date. They kept open communication via text messages daily. I am a night shift health care provider, I cannot tell you how much I needed this mini-vacay."
Reviewed on Oct 9, 2025

Southernmost Beach Resort and Guesthouses
1319 Duval Street, Key West, FL
Fully refundable
$234 nightly
The price is $264 total per night from Oct 29 to Oct 30
$264 total
Oct 29 - Oct 30
Total with taxes and fees
8.6/10 Excellent! (2,787 reviews)
"The balcony was not private it was outside our front door located outside. Other then that it was a great stay!"
Reviewed on Oct 13, 2025

Margaritaville Beach House Key West
2001 South Roosevelt Boulevard, Key West, FL
$235 nightly
The price is $264 total per night from Oct 27 to Oct 28
$264 total
Oct 27 - Oct 28
Total with taxes and fees
8.6/10 Excellent! (1,770 reviews)
"Property was fun, inviting and a great place to relax after a day in Old Town Key West. Shuttle to Old Town was great, food at Margaritaville was very good, staff very friendly. Jimmy Buffett tunes playing all the time was perfect!"
Reviewed on Oct 8, 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.