Long Key Vacation Rentals from $101: Search Short-Term 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.

Layton

Mark H.

$620 nightly

Aug 23 - Aug 24

Total with taxes and fees

2. Breezy Palms Resort

Matecumbe

Tristan

$139 nightly

Sep 1 - Sep 2

Total with taxes and fees

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

Matecumbe

Lauren M.

$1,204 nightly

Aug 16 - Aug 17

Total with taxes and fees

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

Matecumbe

"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."

Mike H.

$1,000 nightly

Aug 22 - Aug 23

Total with taxes and fees

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

Duck Key

lissa h.

$664 nightly

Aug 18 - Aug 19

Total with taxes and fees

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

Marathon

Rachael C.

$569 nightly

Aug 8 - Aug 9

Total with taxes and fees

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

Marathon

Ryan K.

$1,018 nightly

Aug 19 - Aug 20

Total with taxes and fees

8. Tiny Villa, Big Ocean Views| Breathtaking Sunsets

Duck Key

Stephanie

$484 nightly

Aug 9 - Aug 10

Total with taxes and fees

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Top Long Key Hotel Reviews

Lime Tree Bay Resort

10/10 Excellent

"Was very nice and clean"

Islander Resort

8/10 Good

"We really enjoyed our stay. I’m not giving five stars only because I don’t think the property is a true five-star hotel, but it is still very good. The room was clean, the staff was very polite and friendly, and we felt comfortable throughout our stay. Overall, we had a great experience and would gladly come back."

Tranquility Bay Beachfront Hotel and Resort

8/10 Good

"Very good setting and good ideas/resort layout. When we arrived to check in, reception couldnt find our booking so took longer than expected. We asked about the sunset boat tour at reception but were told this was a third party on the beach who close at 5 so unable to get further info, would be good if the reception staff could provide more information or take bookings as they are advertising it. Food and drink at the hotel are expensive. General buildings and rooms could do with a bit of tidying up in places. Fire alarm panel in the building we were staying in was beeping with a fault most of the night so didnt manage to sleep too well."

Rainbow Bend Resort

10/10 Excellent

"Staff was friendly. Room was great stocked with dishes microwave full size frig. Spacious and had a pull out couch bed that was so helpful. Had a front area with tables and chairs, plus umbrellas. Pool was clean and refreshing. They even had kayaks, paddle boards to use for free. Bikes for free. Even breakfast for free. And not just your continental one, we had eggs, pancakes, bacon,sausage, French toast, It was awesome. I’m so glad I chose them. I felt safe since I travel alone with my teenager that means a lot to me. It’s close to a lot of excursions and beaches."

Find out more about Long Key

Everything you need to know about Long Key vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Long Key vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Long Key vacation 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 low season months. For more hustle and bustle, you may prefer to visit Long Key in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $101 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Long Key rentals

At Expedia, we put the best Long Key vacation 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 vacation.

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.

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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.

Long Key Vacation Rentals

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Check prices for these dates

Our top choices for Long Key vacation rentals

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

2. Breezy Palms Resort

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

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

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

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

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

8. Tiny Villa, Big Ocean Views| Breathtaking Sunsets

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

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

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

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

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

14. Treasure Harbor

15. 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!

17. Seas the Keys Getaway with plunge pool/spa

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

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

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

Find vacation rentals that suit your style

Top Long Key Hotel Reviews

Lime Tree Bay Resort

Find out more about Long Key

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