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

Long Key Vacation Rentals

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Our top choices for Long Key vacation 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)
"This is a beautiful place to stay for exploring the keys. We would stay here again."
United States
Mark H.
The price is ¥39,903
¥111,368 total
includes taxes & fees
Aug 23 - Aug 24
Ocean front gated privacy with 3 bedrooms and protected boat slip.

2. Breezy Palms Resort

Breezy Palms Resort
2.5 star property
Matecumbe
8.8 out of 10, Excellent, (714 reviews)
"my 2nd time staying here and i will be back for a 3rd"
United States
Tristan
The price is ¥16,663
¥21,292 total
includes taxes & fees
Aug 13 - Aug 14
Breezy Palms Resort

3. 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
10.0 out of 10, Exceptional, (2 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 ¥89,390
¥203,294 total
includes taxes & fees
Aug 16 - Aug 17
Ocean View Penthouse | Retreat amenities: tennis court, heated Pool | Vista Key Two

4. 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, (164 reviews)
"Kitchen was well-equipped. Views were spectacular and the peaceful setting was everything we needed and hoped for! Would definitely consider this place for a future stay. My kids' favorite feature was the nearby Cabana Club!"
United States
Ryan K.
The price is ¥67,834
¥180,340 total
includes taxes & fees
Aug 18 - Aug 19
Waterfront! 4 Bed/3 BA Townhome, 32FTDock, Cabana Club, Paddleboard, Beach Gear!

5. Treasure Harbor

Treasure Harbor
3.0 star property
Islamorada
9.0 out of 10, Wonderful, (166 reviews)
"The houseboat were a great experience not only for the kid's but the adults also. Seeing the manatees swim around the cove was awesome! It was a great place to meet your neighbors as the porches are very close. The swimming pool is a great addition to the property! If going back to the area, I would definitely go there again! We really enjoyed our visit there!"
United States
Kelly
The price is ¥19,967
¥44,908 total
includes taxes & fees
Aug 5 - Aug 6
Treasure Harbor

6. 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, (34 reviews)
"We had a great stay!!"
United States
lissa h.
The price is ¥58,813
¥125,345 total
includes taxes & fees
Aug 4 - Aug 5
Charming 3-bedroom house featuring a heated private pool.

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, (7 reviews)
"Everything about the stay was nice. "
United States
Mario S.
The price is ¥42,305
¥99,166 total
includes taxes & fees
Aug 3 - Aug 4
Villa 5034 on Duck Key Boat Slip Available - 2BD 2.5BA

8. 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 ¥40,197
¥97,520 total
includes taxes & fees
Aug 3 - Aug 4
Villa 5087 on Duck Key Boat Slip Available - 2BD 2.5BA

9. 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, (3 reviews)
"House was fantastic. Back deck and pool area were so nice !!!"
United States
Ryan M.
The price is ¥135,509
¥246,757 total
includes taxes & fees
Aug 4 - Aug 5
Villa 7218 on Duck Key - 3 BR & 3 BA - Boat Slip Available

10. Villa 7071 on Duck Key Boat Slip Available - 3BD 3BA

Villa 7071 on Duck Key Boat Slip Available - 3BD 3BA
Marathon
10.0 out of 10, Exceptional, (4 reviews)
"Hawks Cay is a really beautiful spot. Frank’s place is nice, clean and convenient to Marathon "
United States
Morgan W.
The price is ¥87,626
¥186,983 total
includes taxes & fees
Aug 4 - Aug 5
Villa 7071 on Duck Key Boat Slip Available - 3BD 3BA

11. 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 ¥39,272
¥94,638 total
includes taxes & fees
Aug 3 - Aug 4
Villa 5053 on Duck Key Boat Slip Available - 2BD 2.5BA

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 ¥46,854
¥104,923 total
includes taxes & fees
Aug 30 - Aug 31
Villa 5008 on Duck Key Boat Slip Available - 2BD 1.5BA

13. 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)
"Great location, beautiful views and clean. "
United States
Deb S. S.
The price is ¥42,313
¥100,228 total
includes taxes & fees
Aug 3 - Aug 4
Villa 5023 on Duck Key Boat Slip Available - 2BD 1.5BA

14. Knight's Key Suites

Knight's Key Suites
3.0 star property
Marathon
9.0 out of 10, Wonderful, (1,218 reviews)
"The rooms are always clean, no bugs, and walking distance to Sunset Grill."
United States
Cristina
The price is ¥13,701
¥18,846 total
includes taxes & fees
Aug 18 - Aug 19
Knight's Key Suites

15. 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
9.0 out of 10, Wonderful, (4 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 ¥47,883
¥155,819 total
includes taxes & fees
Aug 16 - Aug 17
Lovely Water View! 3 Bed, 3 BA Townhome, Cabana Club: Oceanfront Beach, Pool!

16. Yacht Haven Marina

Yacht Haven Marina
3.5 star property
Marathon
9.8 out of 10, Exceptional, (347 reviews)
"Incredible stay , very unique and cozy . Friendly staff ,we will most definitely stay here again. My son had a blast at this place oh and pet friendly even better ."
United States
Christian
The price is ¥18,085
¥42,790 total
includes taxes & fees
Aug 29 - Aug 30
Yacht Haven Marina

17. 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 ¥55,704
¥139,879 total
includes taxes & fees
Aug 12 - Aug 13
Villa 4204 on Duck Key Boat Slip Available - 3BD 2BA

18. Skipjack Resort & Marina

Skipjack Resort & Marina
3.0 star property
Marathon
8.6 out of 10, Excellent, (1,282 reviews)
"I will stay here again"
United States
Peter
The price is ¥23,549
¥32,956 total
includes taxes & fees
Aug 23 - Aug 24
Skipjack Resort & Marina

19. 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, (15 reviews)
"Everything was perfect. Great place to stay"
United States
Kirk r.
The price is ¥50,916
¥107,737 total
includes taxes & fees
Aug 11 - Aug 12
Villa 5020 on Duck Key Boat Slip Available - 2BD 2.5BA

20. Aqua Lodge Rentals At Coconut Cay

Aqua Lodge Rentals At Coconut Cay
3.5 star property
Marathon
9.6 out of 10, Exceptional, (229 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 ¥20,934
¥48,349 total
includes taxes & fees
Aug 30 - Aug 31
Aqua Lodge Rentals At Coconut Cay
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

Search for holiday rentals in Long Key on Expedia! You can easily find your home rentals, villas, holiday apartments in Long Key using one of the methods below:

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Look no further and take a look at our great range of rental properties in Long Key!

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?

ASK ABOUT Sept-Oct2026 SPECIAL! 14Bd10Bth Home Comfortably Accommodates Up to 30: This vacation home rental near Long Key is located by the ocean and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. It has 14 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a balcony, a garden, and a selection of games so you can immerse yourself in your vacation.

How many vacation rentals are there in Long Key?

Choose from 32 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.