A pier with a boat rental sign, a colorful building, and a calm sea.

Long Key Holiday Rentals

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Our top choices for Long Key holiday rentals

1. Ocean front gated privacy with 3 bedrooms and protected boat slip.

Ocean front gated privacy with 3 bedrooms and protected boat slip.
Layton
10.0 out of 10, Exceptional, (63 reviews)
"Awesome place all around!"
United States
Luke B.
The price is NZ$1,093
includes taxes & fees
24 Aug - 25 Aug
Ocean front gated privacy with 3 bedrooms and protected boat slip.

2. Large 1-bedroom apartment with full kitchen & AC

Large 1-bedroom apartment with full kitchen & AC
Plantation Key Colony
The price is NZ$574
includes taxes & fees
24 Aug - 25 Aug
Large 1-bedroom apartment with full kitchen & AC

3. Breezy Palms Resort

Breezy Palms Resort
2.5 star property
Matecumbe
8.8 out of 10, Excellent, (731 reviews)
"Great place to stay rooms were really nice nice boat ramp plenty of parking restaurants right down the street to eat at no complaints nice pool everybody was friendly room was ice cold from the air condition full kitchen nice balcony looking out over the ocean great stay"
United States
roger
The price is NZ$220
includes taxes & fees
1 Sept - 2 Sept
Breezy Palms Resort

4. Treasure Harbor

Treasure Harbor
3.0 star property
Islamorada
9.0 out of 10, Wonderful, (171 reviews)
"We loved sitting in the deck in the evening and again in the morning."
Canada
Molly
The price is NZ$471
includes taxes & fees
24 Aug - 25 Aug
Treasure Harbor

5. Yacht Haven Marina

Yacht Haven Marina
3.5 star property
Marathon
9.8 out of 10, Exceptional, (352 reviews)
"Fantastic place! It was super clean and looked just like the photos. We would stay here again!"
United States
Clara
The price is NZ$401
includes taxes & fees
1 Sept - 2 Sept
Yacht Haven Marina

6. Tropical Cottages

Tropical Cottages
3.0 star property
Marathon
8.6 out of 10, Excellent, (996 reviews)
"A/c was amazing, clean and beautiful cabins."
Canada
Natasha
The price is NZ$169
includes taxes & fees
2 Sept - 3 Sept
Tropical Cottages

7. Aqua Lodge Rentals At Coconut Cay

Aqua Lodge Rentals At Coconut Cay
3.5 star property
Marathon
9.6 out of 10, Exceptional, (232 reviews)
"I never give 5 stars but it was as advertised and good pricing and fun little spot. Keep it up folks.."
Canada
Wesley
The price is NZ$470
includes taxes & fees
13 Sept - 14 Sept
Aqua Lodge Rentals At Coconut Cay

8. 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, (55 reviews)
"Very nice villa "
United States
Grace L.
The price is NZ$809
includes taxes & fees
24 Aug - 25 Aug
Villa 5053 on Duck Key Boat Slip Available - 2BD 2.5BA

9. Villa 5028 on Duck Key Boat Slip Available - 2BD 2.5BA

Villa 5028 on Duck Key Boat Slip Available - 2BD 2.5BA
Duck Key
8.8 out of 10, Excellent, (9 reviews)
"Property was clean and comfortable with an excellent sunset view each evening."
United States
william d.
The price is NZ$809
includes taxes & fees
24 Aug - 25 Aug
Villa 5028 on Duck Key Boat Slip Available - 2BD 2.5BA

10. Knight's Key Suites

Knight's Key Suites
3.0 star property
Marathon
9.0 out of 10, Wonderful, (1,222 reviews)
"The rooms are always clean, no bugs, and walking distance to Sunset Grill."
United States
Cristina
The price is NZ$166
includes taxes & fees
3 Sept - 4 Sept
Knight's Key Suites

11. Seas the Keys Getaway with plunge pool/spa

Seas the Keys Getaway with plunge pool/spa
Marathon
9.6 out of 10, Exceptional, (15 reviews)
"Nice location "
United States
Gina W.
Seas the Keys Getaway with plunge pool/spa

12. Skipjack Resort & Marina

Skipjack Resort & Marina
3.0 star property
Marathon
8.6 out of 10, Excellent, (1,288 reviews)
"Great spot"
Canada
Justin
The price is NZ$313
includes taxes & fees
1 Sept - 2 Sept
Skipjack Resort & Marina

13. Villa 5020 on Duck Key Boat Slip Available - 2BD 2.5BA

Villa 5020 on Duck Key Boat Slip Available - 2BD 2.5BA
Duck Key
9.0 out of 10, Wonderful, (16 reviews)
"Everything was perfect. Great place to stay"
United States
Kirk r.
The price is NZ$870
includes taxes & fees
24 Aug - 25 Aug
Villa 5020 on Duck Key Boat Slip Available - 2BD 2.5BA

14. Villa 5087 on Duck Key Boat Slip Available - 2BD 2.5BA

Villa 5087 on Duck Key Boat Slip Available - 2BD 2.5BA
Duck Key
9.4 out of 10, Exceptional, (23 reviews)
"Great location, well equipped unit!Worked out perfectly"
United States
David N.
The price is NZ$910
includes taxes & fees
24 Aug - 25 Aug
Villa 5087 on Duck Key Boat Slip Available - 2BD 2.5BA

15. Tiny Villa, Big Ocean Views| Breathtaking Sunsets

Tiny Villa, Big Ocean Views| Breathtaking Sunsets
Duck Key
9.8 out of 10, Exceptional, (20 reviews)
"This was without a doubt one of the nicest places we have ever stayed! Our hostess was PHENOMENAL and went above and beyond to be sure we were comfortable and had everything we needed for our stay. Literally the best vacation we’ve had!!!’ I suggest this place to everyone!"
United States
Stephanie
Tiny Villa, Big Ocean Views| Breathtaking Sunsets

16. 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, (2 reviews)
"The location was perfect, house was very clean, and the view was breathtaking. We will 100% return."
United States
Gina A.
The price is NZ$870
includes taxes & fees
24 Aug - 25 Aug
Villa 5008 on Duck Key Boat Slip Available - 2BD 1.5BA

17. Charming 3-bedroom house featuring a heated private pool.

Charming 3-bedroom house featuring a heated private pool.
Duck Key
10.0 out of 10, Exceptional, (37 reviews)
"We had a great stay!!"
United States
lissa h.
The price is NZ$1,043
includes taxes & fees
28 Aug - 29 Aug
Charming 3-bedroom house featuring a heated private pool.

18. Waterfront / Ocean Access Canal / Kamp Key / Homes

Waterfront / Ocean Access Canal / Kamp Key / Homes
Matecumbe
10.0 out of 10, Exceptional, (3 reviews)
"Great VRBO we had an awesome vaction."
United States
Robert E.
The price is NZ$1,435
includes taxes & fees
8 Sept - 9 Sept
Waterfront / Ocean Access Canal / Kamp Key / Homes

19. Lovely Water View! 3 Bed, 3 BA Townhome, Cabana Club: Oceanfront Beach, Pool!

Lovely Water View! 3 Bed, 3 BA Townhome, Cabana Club: Oceanfront Beach, Pool!
Marathon
9.2 out of 10, Wonderful, (5 reviews)
"Place was perfect. Property manager was amazing and always answered questions within minutes. Definitely would stay again"
United States
lori p.
The price is NZ$1,595
includes taxes & fees
13 Sept - 14 Sept
Lovely Water View! 3 Bed, 3 BA Townhome, Cabana Club: Oceanfront Beach, Pool!

20. Villa 4204 on Duck Key Boat Slip Available - 3BD 2BA

Villa 4204 on Duck Key Boat Slip Available - 3BD 2BA
Marathon
9.8 out of 10, Exceptional, (6 reviews)
"The property was very clean."
United States
Kelsey S.
The price is NZ$1,221
includes taxes & fees
24 Aug - 25 Aug
Villa 4204 on Duck Key Boat Slip Available - 3BD 2BA
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

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Long Key holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Long Key. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Long Key. Seeing all the best attractions is bound to make you fall in love with Long Key. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Long Key short-term rentals, that won’t be hard to do.

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?

Coral Lagoon #13: Heated Pool, Views, easy Gulf & Atlantic Access via Vaca Cut: This holiday home rental outside of Long Key is located on the waterfront, and has an outdoor pool, a balcony and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games.

How many holiday rentals are there in Long Key?

Choose from 29 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.