Holiday Rentals in Long Key

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Our top choices for Long Key holiday rentals

Villa 5053 on Duck Key Boat Slip Available - 2BD 2.5BA

Villa 5053 on Duck Key Boat Slip Available - 2BD 2.5BA
Duck Key
9.6 out of 10, Exceptional, (51 reviews)
"It was a pleasant stay and the host was prompt when reaching out to him."
United States
Jill B.
The price is €643
includes taxes & fees
7 Jun - 8 Jun
Villa 5053 on Duck Key Boat Slip Available - 2BD 2.5BA

Knight's Key Suites

Knight's Key Suites
3.0 star property
Marathon
9.0 out of 10, Wonderful, (1,192 reviews)
"Ocean view from room balcony."
United States
Brian
The price is €108
includes taxes & fees
1 Jun - 2 Jun
Knight's Key Suites

Treasure Harbor

Treasure Harbor
3.0 star property
Islamorada
9.0 out of 10, Wonderful, (153 reviews)
"Amazing stay!"
United States
Amanda
The price is €274
includes taxes & fees
14 May - 15 May
Treasure Harbor

Tropical Cottages

Tropical Cottages
3.0 star property
Marathon
8.6 out of 10, Excellent, (967 reviews)
"Great place nice people "
United States
Mark
The price is €124
includes taxes & fees
19 May - 20 May
Tropical Cottages

Luxe Beachfront Villa

Luxe Beachfront Villa
3.0 star property
Matecumbe
The price is €1,520
includes taxes & fees
21 May - 22 May
Luxe Beachfront Villa

Breezy Palms Resort

Breezy Palms Resort
2.5 star property
Matecumbe
8.8 out of 10, Excellent, (671 reviews)
"Place was nicer inside than out. Great location."
United States
Marcos
The price is €111
includes taxes & fees
13 May - 14 May
Breezy Palms Resort

Villa 5034 on Duck Key Boat Slip Available - 2BD 2.5BA

Villa 5034 on Duck Key Boat Slip Available - 2BD 2.5BA
Duck Key
10.0 out of 10, Exceptional, (6 reviews)
"Everything about the stay was nice. "
United States
Mario S.
The price is €545
includes taxes & fees
11 May - 12 May
Villa 5034 on Duck Key Boat Slip Available - 2BD 2.5BA

Sunset Access + Boat Basin | Walkable Islamorada

Sunset Access + Boat Basin | Walkable Islamorada
Matecumbe
10.0 out of 10, Exceptional, (45 reviews)
"Great location, stay, and nice to have the boat slip in the back yard. Will book again."
United States
Orion T.
The price is €453
includes taxes & fees
1 Jun - 2 Jun
Sunset Access + Boat Basin | Walkable Islamorada

Skipjack Resort & Marina

Skipjack Resort & Marina
3.0 star property
Marathon
8.6 out of 10, Excellent, (1,262 reviews)
"The staff was very nice, our room was spacious and comfortable, the area has lots to do"
United States
Carol
The price is €232
includes taxes & fees
31 May - 1 Jun
Skipjack Resort & Marina

Villa 5023 on Duck Key Boat Slip Available - 2BD 1.5BA

Villa 5023 on Duck Key Boat Slip Available - 2BD 1.5BA
Duck Key
9.4 out of 10, Exceptional, (36 reviews)
"Perfect for our get away"
United States
Kelly H.
The price is €643
includes taxes & fees
7 Jun - 8 Jun
Villa 5023 on Duck Key Boat Slip Available - 2BD 1.5BA

The Islands of Islamorada

The Islands of Islamorada
4.0 star property
Matecumbe
9.6 out of 10, Exceptional, (75 reviews)
"What a wonderful venue for our last 2 nights in the Keys. This place is a hidden gem. The entire staff, especially Edith, the bartender, were fantastic."
United States
Michael
The price is €600
includes taxes & fees
11 May - 12 May
The Islands of Islamorada

Canal Front Luxury Condo with Pool + Breakfast

Canal Front Luxury Condo with Pool + Breakfast
Marathon
9.8 out of 10, Exceptional, (27 reviews)
"Super easy check in, great location in the Keys and very quiet in the room."
United States
Eric
The price is €363
includes taxes & fees
11 May - 12 May
Canal Front Luxury Condo with Pool + Breakfast

Villa 7218 on Duck Key - 3 BR & 3 BA - Boat Slip Available

Villa 7218 on Duck Key - 3 BR & 3 BA - Boat Slip Available
Duck Key
10.0 out of 10, Exceptional, (2 reviews)
"House was fantastic. Back deck and pool area were so nice !!!"
United States
Ryan M.
The price is €956
includes taxes & fees
11 May - 12 May
Villa 7218 on Duck Key - 3 BR & 3 BA - Boat Slip Available

Villa 5086 on Duck Key Boat Slip Available - 2BD 1.5BA

Villa 5086 on Duck Key Boat Slip Available - 2BD 1.5BA
Duck Key
8.6 out of 10, Excellent, (28 reviews)
"Great location! We enjoyed our time there."
United States
Erin T.
The price is €470
includes taxes & fees
10 May - 11 May
Villa 5086 on Duck Key Boat Slip Available - 2BD 1.5BA

Villa 5008 on Duck Key Boat Slip Available - 2BD 1.5BA

Villa 5008 on Duck Key Boat Slip Available - 2BD 1.5BA
Duck Key
10.0 out of 10, Exceptional, (1 review)
"The location was perfect, house was very clean, and the view was breathtaking. We will 100% return."
United States
Gina A.
The price is €544
includes taxes & fees
18 May - 19 May
Villa 5008 on Duck Key Boat Slip Available - 2BD 1.5BA

Villa 7075 on Duck Key Boat Slip Available - 2BD 2.5BA

Villa 7075 on Duck Key Boat Slip Available - 2BD 2.5BA
Marathon
9.2 out of 10, Wonderful, (32 reviews)
"Wonderful experience, great views, clean rooms, great amount of space. Great price"
United States
Race
The price is €545
includes taxes & fees
11 May - 12 May
Villa 7075 on Duck Key Boat Slip Available - 2BD 2.5BA

Waterfront! 4 Bed/3 BA Townhome, 32FTDock, Cabana Club, Paddleboard, Beach Gear!

Waterfront! 4 Bed/3 BA Townhome, 32FTDock, Cabana Club, Paddleboard, Beach Gear!
Marathon
10.0 out of 10, Exceptional, (163 reviews)
"Everything was as advertised. Meredith was so helpful and on it. Very well maintained and clean. "
United States
John J.
Waterfront! 4 Bed/3 BA Townhome, 32FTDock, Cabana Club, Paddleboard, Beach Gear!

Brand New Marina Suite with Pool + Free Breakfast

Brand New Marina Suite with Pool + Free Breakfast
Marathon
10.0 out of 10, Exceptional, (1 review)
"Very clean and convenient to shops and restaurants "
United States
JOHN
The price is €428
includes taxes & fees
12 May - 13 May
Brand New Marina Suite with Pool + Free Breakfast

Yacht Haven Marina

Yacht Haven Marina
3.5 star property
Marathon
9.6 out of 10, Exceptional, (306 reviews)
"Fabulous place and location. Can not wait to go back"
United States
Dianne
The price is €245
includes taxes & fees
7 Jun - 8 Jun
Yacht Haven Marina

1.5 Bedroom, 1 bath with back deck. Pet friendly with 2 Queen and 2 twin beds.

1.5 Bedroom, 1 bath with back deck. Pet friendly with 2 Queen and 2 twin beds.
Tavernier
9.6 out of 10, Exceptional, (4 reviews)
"Our stay was fantastic !We had everything we needed, including absolutely stunning subsets.I would stay here again in a heartbeat."
United States
Tina P.
The price is €405
includes taxes & fees
7 Jun - 8 Jun
1.5 Bedroom, 1 bath with back deck. Pet friendly with 2 Queen and 2 twin beds.
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 €108 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. Kick off your shoes and enjoy yourself with a selection of games and 1 hot tub.

How many holiday rentals are there in Long Key?

Choose from 32 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.