Key Haven Vacation Rentals

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Our top choices for Key Haven vacation rentals

Vacation Home in Raccoon Key

Altair House at Lunara Bay
10.0 out of 10, Exceptional, (11)
"Great house. Large space, everything you need is there. "
United States
CRIMSON A.
$1,884 nightly
The price is $2,090
Dec 17 - Dec 18
Total with taxes and fees
Altair House at Lunara Bay

Vacation Home in Raccoon Key

Capmar House by Brightwild Huge Home Pool
2.0 star property
10.0 out of 10, Exceptional, (1)
"Wonderful property, 4 large bedroom and en suite bathroom, private pool we really liked our stay"
France
Karen
$1,646 nightly
The price is $1,852
Dec 17 - Dec 18
Total with taxes and fees
Capmar House by Brightwild Huge Home Pool

Vacation Home in Raccoon Key

Waterfront Luxury Home - Tidelands House
2.0 star property
$2,964 nightly
The price is $3,335
Jan 12 - Jan 13, 2026
Total with taxes and fees
Waterfront Luxury Home - Tidelands House
9.6 out of 10, Exceptional, (85)
"The views, pool, water and amenities are incredible! The host was welcoming and very accomidating!!Our family reunion with 23 people was the best at this location! So fun!"
United States
Diana G.
Real World MTV House-18 to 22 guests, Not Just a House Your Own Private Resort

Vacation Home in Raccoon Key

New Waterfront Home - Sunray House
2.0 star property
$2,964 nightly
The price is $3,335
Jan 12 - Jan 13, 2026
Total with taxes and fees
New Waterfront Home - Sunray House

Vacation Home in Raccoon Key

Brand New The Greenmoor House With Pool
2.0 star property
$2,587 nightly
The price is $2,911
Jan 12 - Jan 13, 2026
Total with taxes and fees
Brand New The Greenmoor House With Pool

Vacation Home in Raccoon Key

Parking Pool Dock - Shellstone House
2.0 star property
$3,105 nightly
The price is $3,493
Jan 12 - Jan 13, 2026
Total with taxes and fees
Parking Pool Dock - Shellstone House

Vacation Home in Raccoon Key

The Joyrise House at Solaire Lunara Bay
2.0 star property
$2,152 nightly
The price is $2,422
Jan 7 - Jan 8, 2026
Total with taxes and fees
The Joyrise House at Solaire Lunara Bay

Houseboat in Stock Island

Aqua Lodges at Hurricane Hole Marina
2.0 star property
8.8 out of 10, Excellent, (170)
"Location , staff , and aqua lodge were perfect."
United States
William
$271 nightly
The price is $304
Dec 17 - Dec 18
Total with taxes and fees
Aqua Lodges at Hurricane Hole Marina
3.5 star property
8.6 out of 10, Excellent, (321)
"Place was great bed was comfy and the water was HOT!!! "
United States
Angela
$305 nightly
The price is $343
Dec 22 - Dec 23
Total with taxes and fees
Hyatt Vacation Club at Sunset Harbor, Key West

Aparthotel in Key West

Ocean Front One Bedroom Residence
2.0 star property
Ocean Front One Bedroom Residence
2.0 star property
10.0 out of 10, Exceptional, (2)
"Great place it is a full apartment with everything you could need and very clean "
United States
Luis
$376 nightly
The price is $423
Dec 18 - Dec 19
Total with taxes and fees
Island View 1BR Residence With Balcony
2.0 star property
10.0 out of 10, Exceptional, (2)
"Clean and spacious. Great view from room!"
United States
Jacqueline
$476 nightly
The price is $536
Dec 17 - Dec 18
Total with taxes and fees
Ocean Front 1BR Suite With Direct Beach Access
9.6 out of 10, Exceptional, (413)
"Everything was excellent!"
United States
Susan L.
$349 nightly
The price is $387
Jan 14 - Jan 15, 2026
Total with taxes and fees
Steps from Duval, Pool on Site & Bikes Included!
3.0 star property
8.2 out of 10, Very Good, (821)
"The staff goes above and beyond very, very warm and nice people"
United States
erik
Coconut Mallory Resort And Marina By Kees Vacations
10.0 out of 10, Exceptional, (27)
"Clean room, amazing location, the host was very communicative and helpful. They had a car service ready to pick us up at the airport which was phenomenal. "
United States
Lauren S.
$342 nightly
The price is $376
Dec 17 - Dec 18
Total with taxes and fees
Heron Suite | Vibrant Retreat, Hot Tubs, Steps from Duval Street!
10.0 out of 10, Exceptional, (142)
"As always, the host and house provided a great experience in KW. We have stayed there multiple times and will continue coming back!"
United States
Tom H.
Heart of Downtown Key West Cottage With Off-Street Parking
7.8 out of 10, Good, (26)
"This was exactly what was advertised, it was clean, and in a great location. The on-site restaurant had great food. Also, all staff members we encountered were very friendly and accommodating. I hope it’s available for our next trip."
United States
Julie
$451 nightly
The price is $501
Dec 20 - Dec 21
Total with taxes and fees
Viking Yacht Getaway in the Keys !!NEW LOCATION!! !!Tons of Amenities!!

Vacation Home in Key West Historic District

Private Parking, Heated Pool - Sweet Caroline
8.6 out of 10, Excellent, (20)
"It is definitely an historic property with some cracks in the floor boards and bathrooms but it has its charms and the location is excellent! I would stay there again!"
United States
Martha B.
$740 nightly
The price is $822
Dec 21 - Dec 22
Total with taxes and fees
Private Parking, Heated Pool - Sweet Caroline
Charming 3-bedroom houseboat with AC in perfect Key West, Sleeps 10 Guests!
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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Top Key Haven Hotel Reviews

Find out more about Key Haven

Everything you need to know about Key Haven vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Key Haven vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Key Haven vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Key Haven vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Key Haven. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Key Haven in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $304 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Key Haven rentals

At Expedia, we put the best Key Haven vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Key Haven rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Key Haven vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Key Haven. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.