Long Key Vacation Rentals

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Our top choices for Long Key vacation rentals

Houseboat in Islamorada

Treasure Harbor
3.0 star property
9.0 out of 10, Wonderful, (117)
"I am obsessed with tiny houses and this one floats! It was so relaxing to sit on the deck and enjoy the view. The bed was very comfy and the gentle motion of the water put me right to sleep. The staff are friendly and helpful. Islamorada is beautiful and fun to explore."
United States
Mary
$277 nightly
The price is $312
Jan 8 - Jan 9, 2026
Total with taxes and fees
Treasure Harbor

Cottage in Marathon

Tropical Cottages
3.0 star property
8.6 out of 10, Excellent, (910)
"Decent stay, easy check in and contactless checkout. Very quiet and nice place! "
United States
Swastik
$135 nightly
The price is $152
Jan 8 - Jan 9, 2026
Total with taxes and fees
Tropical Cottages

Houseboat in Marathon

Yacht Haven Marina
3.5 star property
9.8 out of 10, Exceptional, (241)
"Friendly staff and extremely clean."
United States
Travis
$284 nightly
The price is $320
Jan 6 - Jan 7, 2026
Total with taxes and fees
Yacht Haven Marina

Aparthotel in Matecumbe

Breezy Palms Resort
2.5 star property
8.8 out of 10, Excellent, (590)
"we stayed in the beach front cottage kitchen was stocked room was clean and the views were great friendly staff "
United States
Terry
$230 nightly
The price is $259
Jan 8 - Jan 9, 2026
Total with taxes and fees
Breezy Palms Resort

Aparthotel in Marathon

Knight's Key Suites
3.0 star property
9.0 out of 10, Wonderful, (1157)
"Very good location.. Clean room."
United States
Leonor
$147 nightly
The price is $162
Jan 15 - Jan 16, 2026
Total with taxes and fees
Knight's Key Suites
9.8 out of 10, Exceptional, (210)
"Heidi has a little bit of paradise on her houseboat! You must plan on staying!!"
United States
Toni M.
$451 nightly
The price is $501
Jan 11 - Jan 12, 2026
Total with taxes and fees
Fla Keys Luxury Houseboat, Prime Location-Steps to Fun, Food & Water Adventures
3.5 star property
9.6 out of 10, Exceptional, (199)
"A unique and interesting place to vacation. Relaxing yet close enough to things to do. I highly recommend the Aqua Loge rentals as a place to stay."
United States
Keith
$345 nightly
The price is $388
Jan 11 - Jan 12, 2026
Total with taxes and fees
Aqua Lodge Rentals At Coconut Cay

Aparthotel in Marathon

Skipjack Resort & Marina
3.0 star property
8.6 out of 10, Excellent, (1218)
"Beautiful location clean rooms friendly staff "
United States
Tiffany
$262 nightly
The price is $295
Jan 5 - Jan 6, 2026
Total with taxes and fees
Skipjack Resort & Marina
10.0 out of 10, Exceptional, (2)
"The property manager was SO nice. She made sure we were comfortable as we brought a big dog. They made sure that the boat we chose was big enough for us! This was a super fun stay. We would absolutely stay here again. "
United States
Hannah B.
$415 nightly
The price is $462
Jan 3 - Jan 4, 2026
Total with taxes and fees
1.5 Bedroom, 1 bath with back deck. Pet friendly with 2 Queen and 2 twin beds.
9.0 out of 10, Wonderful, (4)
"Unit was very clean and recently remodeled. The building was a little difficult to find in the dark at night, but I would definitely recommend staying here again."
United States
Nancy M.
$367 nightly
The price is $408
Jan 13 - Jan 14, 2026
Total with taxes and fees
Tropical Oasis on Sombrero Beach in the Heart of Marathon FL

Villa in Matecumbe

The Islands of Islamorada
4.0 star property
9.8 out of 10, Exceptional, (70)
"Great for family vacation with kids. love it"
United States
Dixania
$658 nightly
The price is $740
Jan 5 - Jan 6, 2026
Total with taxes and fees
The Islands of Islamorada
9.6 out of 10, Exceptional, (18)
"I just finished a detailed response to the owner. We were well satisfied with the property and it's location."
United States
Michael S.
Waterfront Fun: Pool, Marina, Tiki Bar & Beach!
9.6 out of 10, Exceptional, (46)
"Clean property! Great views! Great communication with owner! Perfect location- close to marathon and key west! "
United States
candi b.
$572 nightly
The price is $636
Jan 5 - Jan 6, 2026
Total with taxes and fees
Villa 5053 on Duck Key Boat Slip Available - 2BD 2.5BA
9.6 out of 10, Exceptional, (57)
"Very clean. "
United States
Oksana K.
$574 nightly
The price is $638
Jan 5 - Jan 6, 2026
Total with taxes and fees
Villa 5027 on Duck Key Boat Slip Available - 2BD 2.5BA
8.0 out of 10, Very Good, (2)
"Great Home & Location & Enjoyable Stay! Thanks!"
United States
James J.
$649 nightly
The price is $721
Jan 12 - Jan 13, 2026
Total with taxes and fees
Charming 2-bedroom house in Marathon with pool
9.2 out of 10, Wonderful, (18)
"Property was very nice, everything as expected based on listing. Very good place for families."
United States
Nicholas H.
$576 nightly
The price is $640
Jan 11 - Jan 12, 2026
Total with taxes and fees
Villa 5087 on Duck Key Boat Slip Available - 2BD 2.5BA
9.4 out of 10, Exceptional, (32)
"A short weekend getaway was made perfect in this villa. The location is idyllic; especially the balcony overlooking the bay with a perfect sunset view. The home was well-appointed, simple yet all the necessities were covered. Communication with the property manager was excellent. Definitely will book again. "
United States
Natasha A.
$570 nightly
The price is $634
Jan 4 - Jan 5, 2026
Total with taxes and fees
Villa 5023 on Duck Key Boat Slip Available - 2BD 1.5BA
10.0 out of 10, Exceptional, (13)
"Beautiful views. Very nice accommodations. Wonderfull location!"
United States
michael h.
$606 nightly
The price is $647
Dec 24 - Dec 25
Total with taxes and fees
Tiny Villa, Big Ocean Views| Breathtaking Sunsets
10.0 out of 10, Exceptional, (1)
"The location was perfect, house was very clean, and the view was breathtaking. We will 100% return."
United States
Gina A.
$649 nightly
The price is $721
Jan 5 - Jan 6, 2026
Total with taxes and fees
Villa 5008 on Duck Key Boat Slip Available - 2BD 1.5BA
9.2 out of 10, Wonderful, (30)
"Wonderful experience, great views, clean rooms, great amount of space. Great price"
United States
Race
$564 nightly
The price is $628
Jan 13 - Jan 14, 2026
Total with taxes and fees
Villa 7075 on Duck Key Boat Slip Available - 2BD 2.5BA
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 Long Key Hotel Reviews

Find out more about Long Key

Everything you need to know about Long Key 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 Long Key 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 Long Key vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Long Key vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Long Key. 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 Long Key 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 $152 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 Long Key rentals

At Expedia, we put the best Long Key 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 Long Key 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 Long Key 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 Long Key. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Can I find a vacation rental in Long Key?

Yes, there are vacation rentals close to popular attractions in Long Key, or you can select a more secluded option if you want a relaxing place to stay. Nature enthusiasts will enjoy the beaches in Long Key. Make sure you have time to check out the seafood restaurants while you're in the area.

What are some of the best vacation home rentals in Long Key?

The Hammocks at Marathon: This vacation home rental near Long Key is located by the ocean and has an outdoor pool, a balcony, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities like a microwave and a coffee maker can make your vacation run smoothly. You and your friends and family can relax into your vacation with amenities like a hot tub.

How many vacation rentals are there in Long Key?

Choose from 34 Expedia vacation rentals in Long Key for a memorable vacation.

What can I see and do in Long Key?

While exploring the area, visit family-friendly sights like Crane Point Museum and Nature Center, or get outside and enjoy nature at Fiesta Key. Long Key State Park and Anne's Beach are a couple of places you'll find in the larger area.

What are vacation rentals like in Long Key?

Vacation rentals are privately owned properties you can reserve for a couple days or more in Long Key. Vacation rentals feature amenities like laundry facilities and kitchens so you'll have a home away from home. If you're concerned about a clean environment, a vacation rental can provide a sense of safety away from public hotel elevators and busy front desks while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is an attractive option for small groups.