Holiday Rentals in Long Key

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Our top choices for Long Key holiday 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
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
The price is €130
includes taxes & fees
8 Jan - 9 Jan 2026
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
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
The price is €198
includes taxes & fees
11 Jan - 12 Jan 2026
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
The price is €138
includes taxes & fees
15 Jan - 16 Jan 2026
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.
The price is €438
includes taxes & fees
11 Jan - 12 Jan 2026
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
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
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.
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.
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
The price is €629
includes taxes & fees
6 Jan - 7 Jan 2026
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.
The price is €553
includes taxes & fees
5 Jan - 6 Jan 2026
Villa 5053 on Duck Key Boat Slip Available - 2BD 2.5BA
9.6 out of 10, Exceptional, (57)
"Very clean. "
United States
Oksana K.
The price is €555
includes taxes & fees
5 Jan - 6 Jan 2026
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.
The price is €640
includes taxes & fees
5 Jan - 6 Jan 2026
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.
The price is €552
includes taxes & fees
22 Jan - 23 Jan 2026
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.
The price is €551
includes taxes & fees
4 Jan - 5 Jan 2026
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.
The price is €564
includes taxes & fees
24 Dec - 25 Dec
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.
The price is €627
includes taxes & fees
5 Jan - 6 Jan 2026
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
The price is €550
includes taxes & fees
13 Jan - 14 Jan 2026
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 holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Long Key holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Long Key holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Long Key holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Long Key holiday rentals we have selected for you start as low as €130 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Long Key rentals

At Expedia, we put the best Long Key holiday 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 holiday.

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 holiday rental in Long Key?

Yes, there are holiday rentals close to the most popular sights in Long Key, or you can select a more secluded option if you're looking for a relaxing 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 holiday rentals that Long Key has to offer?

The Hammocks at Marathon: This holiday home rental outside of Long Key is located by the ocean, and has an outdoor pool, a balcony and a BBQ to put you at ease in your new surroundings. Kitchen amenities such as a microwave and a coffee maker can make your holiday run smoothly. You and your friends and family can relax into your holiday with amenities such as 1 hot tub.

How many holiday rentals are there in Long Key?

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

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 wider area.

What are holiday rentals like in Long Key?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Long Key. Holiday rentals feature amenities such as kitchens and laundry facilities so you'll have all the conveniences of home. If you're concerned about cleanliness, holiday rentals can offer a sense of security away from public hotel lifts and busy lobbies while still allowing you to travel. You'll also find more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a great choice for family trips or small group gatherings.