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Holiday Rentals in Long Key

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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)
"This is a beautiful place to stay for exploring the keys. We would stay here again."
United States
Mark H.
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, (719 reviews)
"my 2nd time staying here and i will be back for a 3rd"
United States
Tristan
The price is €143
includes taxes & fees
10 Aug - 11 Aug
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 €1,156
includes taxes & fees
16 Aug - 17 Aug
Ocean View Penthouse | Retreat amenities: tennis court, heated Pool | Vista Key Two

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

Waterfront / Ocean Access Canal / Kamp Key / Homes
Matecumbe
10.0 out of 10, Exceptional, (2 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 €956
includes taxes & fees
22 Aug - 23 Aug
Waterfront / Ocean Access Canal / Kamp Key / Homes

5. 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 €684
includes taxes & fees
17 Aug - 18 Aug
Charming 3-bedroom house featuring a heated private pool.

6. 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)
"Great stay. I love being on the boardwalk. "
United States
Rachael C.
The price is €576
includes taxes & fees
8 Aug - 9 Aug
Villa 7075 on Duck Key Boat Slip Available - 2BD 2.5BA

7. 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 €971
includes taxes & fees
19 Aug - 20 Aug
Waterfront! 4 Bed/3 BA Townhome, 32FTDock, Cabana Club, Paddleboard, Beach Gear!

8. 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
The price is €445
includes taxes & fees
9 Aug - 10 Aug
Tiny Villa, Big Ocean Views| Breathtaking Sunsets

9. 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.
Villa 5023 on Duck Key Boat Slip Available - 2BD 1.5BA

10. 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 €552
includes taxes & fees
1 Sept - 2 Sept
Villa 5087 on Duck Key Boat Slip Available - 2BD 2.5BA

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 €517
includes taxes & fees
10 Aug - 11 Aug
Villa 5053 on Duck Key Boat Slip Available - 2BD 2.5BA

12. 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 €503
includes taxes & fees
11 Aug - 12 Aug
Villa 5028 on Duck Key Boat Slip Available - 2BD 2.5BA

13. 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 €1,141
includes taxes & fees
11 Aug - 12 Aug
Villa 7218 on Duck Key - 3 BR & 3 BA - Boat Slip Available

14. 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 €244
includes taxes & fees
12 Aug - 13 Aug
Treasure Harbor

15. 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 €575
includes taxes & fees
19 Aug - 20 Aug
Villa 5020 on Duck Key Boat Slip Available - 2BD 2.5BA

16. 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 €846
includes taxes & fees
19 Aug - 20 Aug
Lovely Water View! 3 Bed, 3 BA Townhome, Cabana Club: Oceanfront Beach, Pool!

17. 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)
"Great location, great accomodation, hot tub and patio in the back area was great for relaxing in the evenings."
United States
Justus
The price is €436
includes taxes & fees
31 Aug - 1 Sept
Seas the Keys Getaway with plunge pool/spa

18. 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 €786
includes taxes & fees
10 Aug - 11 Aug
Villa 4204 on Duck Key Boat Slip Available - 3BD 2BA

19. 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 €530
includes taxes & fees
1 Sept - 2 Sept
Villa 5008 on Duck Key Boat Slip Available - 2BD 1.5BA

20. Villa 7205 on Duck Key - 3 BR & 3 BA - Boat Slip available

Villa 7205 on Duck Key - 3 BR & 3 BA - Boat Slip available
Duck Key
The price is €1,182
includes taxes & fees
10 Aug - 11 Aug
Villa 7205 on Duck Key - 3 BR & 3 BA - Boat Slip available
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 €88 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. 

Explore a world of travel with Expedia

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?

ASK ABOUT Sept-Oct2026 SPECIAL! 14Bd10Bth Home Comfortably Accommodates Up to 30: This holiday home rental outside of Long Key is located by the ocean, and has an outdoor pool, a fireplace and a BBQ 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 that you can cook with friends or family. It offers a balcony, a garden and a selection of games so that you can immerse yourself in your holiday.

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.