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. Breezy Palms Resort

Breezy Palms Resort
2.5 star property
Matecumbe
9.0 out of 10, Wonderful, (762 reviews)
"Such a great place to stay!!"
United States
Gavin
The price is NZ$238
includes taxes & fees
21 Oct - 22 Oct
Breezy Palms Resort

2. Tropical Cottages

Tropical Cottages
3.0 star property
Marathon
8.6 out of 10, Excellent, (1,005 reviews)
"Cute little cottage perfect for couples had an amazing stay and will definitely be back to tropical cottages again"
United States
Aaron
The price is NZ$159
includes taxes & fees
18 Oct - 19 Oct
Tropical Cottages

3. Knight's Key Suites

Knight's Key Suites
3.0 star property
Marathon
9.0 out of 10, Wonderful, (1,239 reviews)
"Clean, easy check in and check out, nice supplies in the kitchen"
United States
Mengqiao
The price is NZ$189
includes taxes & fees
13 Oct - 14 Oct
Knight's Key Suites

4. Aqua Lodge Rentals At Coconut Cay

Aqua Lodge Rentals At Coconut Cay
3.5 star property
Marathon
9.6 out of 10, Exceptional, (237 reviews)
"Never stayed in a houseboat before. It was a novel experience!"
United States
Susan
The price is NZ$435
includes taxes & fees
13 Oct - 14 Oct
Aqua Lodge Rentals At Coconut Cay

5. Yacht Haven Marina

Yacht Haven Marina
3.5 star property
Marathon
9.6 out of 10, Exceptional, (370 reviews)
"Loved staying in the aqua lodges, such a relaxing place."
United States
Lauren
The price is NZ$466
includes taxes & fees
19 Oct - 20 Oct
Yacht Haven Marina

6. Treasure Harbor

Treasure Harbor
3.0 star property
Islamorada
9.0 out of 10, Wonderful, (177 reviews)
"Beautiful unique place"
United States
Laura
The price is NZ$466
includes taxes & fees
10 Oct - 11 Oct
Treasure Harbor

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

Villa 5034 on Duck Key Boat Slip Available - 2BD 2.5BA
Duck Key
9.8 out of 10, Exceptional, (8 reviews)
"Great Location! The house was beautiful and clean We had a great time!"
United States
Andres
The price is NZ$909
includes taxes & fees
12 Oct - 13 Oct
Villa 5034 on Duck Key Boat Slip Available - 2BD 2.5BA

8. Skipjack Resort & Marina

Skipjack Resort & Marina
3.0 star property
Marathon
8.6 out of 10, Excellent, (1,293 reviews)
"Great spot"
Canada
Justin
The price is NZ$335
includes taxes & fees
12 Oct - 13 Oct
Skipjack Resort & Marina

9. 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)
"Awesome place to stay"
United States
Takuma F.
The price is NZ$930
includes taxes & fees
12 Oct - 13 Oct
Villa 5087 on Duck Key Boat Slip Available - 2BD 2.5BA

10. 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.
The price is NZ$820
includes taxes & fees
12 Oct - 13 Oct
Seas the Keys Getaway with plunge pool/spa

11. Aqua Lodges at 47th Street Gulfside

Aqua Lodges at 47th Street Gulfside
3.0 star property
Marathon
8.8 out of 10, Excellent, (59 reviews)
"Loved our stay at the aqua lodges 10/10 would do it again"
United States
Lauren
The price is NZ$434
includes taxes & fees
14 Oct - 15 Oct
Aqua Lodges at 47th Street Gulfside

12. 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$930
includes taxes & fees
12 Oct - 13 Oct
Villa 5008 on Duck Key Boat Slip Available - 2BD 1.5BA

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$930
includes taxes & fees
12 Oct - 13 Oct
Villa 5020 on Duck Key Boat Slip Available - 2BD 2.5BA

14. 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)
"Great location. Pretty views of Bay. Comfortable rooms. Enjoyed our brief stay for July 4th."
United States
Jorge D.
The price is NZ$909
includes taxes & fees
12 Oct - 13 Oct
Villa 5053 on Duck Key Boat Slip Available - 2BD 2.5BA

15. Villa 7079 on Duck Key - Boat Slip Available

Villa 7079 on Duck Key - Boat Slip Available
Marathon
The price is NZ$1,367
includes taxes & fees
12 Oct - 13 Oct
Villa 7079 on Duck Key - Boat Slip Available

16. 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$1,285
includes taxes & fees
12 Oct - 13 Oct
Villa 4204 on Duck Key Boat Slip Available - 3BD 2BA

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

Waterfront / Ocean Access Canal / Kamp Key / Homes
Matecumbe
8.8 out of 10, Excellent, (5 reviews)
"Excellent house. Very clean. We had a little trouble with the check in code and we were immediately contacted and the code was changed and we were in within minutes. The maintenance guy stopped by to make sure we got in and everything was good. EXCELLENT Customer Service!!!!!House was very well stocked with pots and pans and misc things needed for a week stay! Right on a nice little canal with plenty of room for our boat."
United States
Mike H.
The price is NZ$1,704
includes taxes & fees
12 Oct - 13 Oct
Waterfront / Ocean Access Canal / Kamp Key / Homes

18. 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$1,644
includes taxes & fees
19 Oct - 20 Oct
Lovely Water View! 3 Bed, 3 BA Townhome, Cabana Club: Oceanfront Beach, Pool!

19. 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, (45 reviews)
"We had a great stay!!"
United States
lissa h.
The price is NZ$1,356
includes taxes & fees
13 Oct - 14 Oct
Charming 3-bedroom house featuring a heated private pool.

20. Ocean View Penthouse | Retreat amenities: tennis court, heated Pool | Vista Key Two

Ocean View Penthouse | Retreat amenities: tennis court, heated Pool | Vista Key Two
Matecumbe
9.8 out of 10, Exceptional, (6 reviews)
"Absolutely great location with a well stocked kitchen for making great meals in and plenty of space to relax after a fun day in the sun!"
United States
Lauren M.
The price is NZ$1,958
includes taxes & fees
13 Oct - 14 Oct
Ocean View Penthouse | Retreat amenities: tennis court, heated Pool | Vista Key Two
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?

Bluegreen Vacations Hammocks at Marathon, Ascend Collection Resort: 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 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.