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

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, (62 reviews)
"This is a beautiful place to stay for exploring the keys. We would stay here again."
United States
Mark H.
The price is NZ$1,688
includes taxes & fees
26 July - 27 July
Ocean front gated privacy with 3 bedrooms and protected boat slip.

Breezy Palms Resort

Breezy Palms Resort
2.5 star property
Matecumbe
8.8 out of 10, Excellent, (704 reviews)
"Enjoyed this place."
United States
Christopher
The price is NZ$260
includes taxes & fees
7 July - 8 July
Breezy Palms Resort

Tropical Cottages

Tropical Cottages
3.0 star property
Marathon
8.6 out of 10, Excellent, (984 reviews)
"It was a very enjoyable stay, highly recommend."
United States
Andrea
The price is NZ$207
includes taxes & fees
7 July - 8 July
Tropical Cottages

Knight's Key Suites

Knight's Key Suites
3.0 star property
Marathon
9.0 out of 10, Wonderful, (1,208 reviews)
"Great view of the 7 mile bridge, great restaurant close by"
United States
Eric
The price is NZ$213
includes taxes & fees
6 Aug - 7 Aug
Knight's Key Suites

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, (53 reviews)
"Very nice villa "
United States
Grace L.
The price is NZ$1,041
includes taxes & fees
3 Aug - 4 Aug
Villa 5053 on Duck Key Boat Slip Available - 2BD 2.5BA

Treasure Harbor

Treasure Harbor
3.0 star property
Islamorada
9.0 out of 10, Wonderful, (162 reviews)
"Amazing stay!"
United States
Amanda
The price is NZ$513
includes taxes & fees
7 July - 8 July
Treasure Harbor

Caloosa Cove Resort by CoolVacay

Caloosa Cove Resort by CoolVacay
3.0 star property
Matecumbe
9.8 out of 10, Exceptional, (7 reviews)
"Easy check in if you come After business hours. Kayaks and sport equipment available. Has a small beach which is unique to the Keys. Pool pretty much vacant at all times. Great views. Highly recommend."
United States
Dana
The price is NZ$520
includes taxes & fees
13 July - 14 July
Caloosa Cove Resort by CoolVacay

Bluegreen Vacations Hammocks at Marathon, Ascend Collection Resort

Bluegreen Vacations Hammocks at Marathon, Ascend Collection Resort
2.5 star property
Marathon
9.2 out of 10, Wonderful, (140 reviews)
"This was the perfect place, right on the ocean and a full kitchen so you can cook your own meals. The room was very clean, I loved that they had a laundry basket and laundry detergent in the room for you, came in handy seeing as we stayed for 7 days. Amazing place to watch the sunset from a hammock and we got lucky enough to see some nurse sharks at the docks right outside of our hotel."
United States
Andrew Jackson
The price is NZ$500
includes taxes & fees
12 July - 13 July
Bluegreen Vacations Hammocks at Marathon, Ascend Collection Resort

Marina View Escape with Pool, Tiki & Breakfast

Marina View Escape with Pool, Tiki & Breakfast
Marathon
10.0 out of 10, Exceptional, (3 reviews)
"Great area"
United States
Jennifer W.
The price is NZ$710
includes taxes & fees
8 July - 9 July
Marina View Escape with Pool, Tiki & Breakfast

Resort Condo with Marina Views, Pool, Tiki, Breakfast

Resort Condo with Marina Views, Pool, Tiki, Breakfast
Marathon
9.4 out of 10, Exceptional, (22 reviews)
"Great place to stay which had everything we needed. Very quiet. We loved it and would stay there again!"
United States
Heather K.
The price is NZ$788
includes taxes & fees
7 July - 8 July
Resort Condo with Marina Views, Pool, Tiki, Breakfast

Yacht Haven Marina

Yacht Haven Marina
3.5 star property
Marathon
9.8 out of 10, Exceptional, (333 reviews)
"We love the accommodations and ability to cook with a full kitchen."
United States
Cheryl
The price is NZ$469
includes taxes & fees
9 July - 10 July
Yacht Haven Marina

Skipjack Resort & Marina

Skipjack Resort & Marina
3.0 star property
Marathon
8.6 out of 10, Excellent, (1,279 reviews)
"I love the staff, really helping me when we need The place is excellent location, the bungalow was in pristine condition, and the area outside was wonderful"
United States
Ysabel
The price is NZ$417
includes taxes & fees
2 Aug - 3 Aug
Skipjack Resort & Marina

Flip-Flops & Sunshine: Islamorada Studio Escape

Flip-Flops & Sunshine: Islamorada Studio Escape
Matecumbe
10.0 out of 10, Exceptional, (6 reviews)
"Very nice clean place. Pool amazing with great views of ocean"
United States
Dawn S.
The price is NZ$594
includes taxes & fees
8 July - 9 July
Flip-Flops & Sunshine: Islamorada Studio Escape

Fla Keys Luxury Houseboat, Prime Location-Steps to Fun, Food & Water Adventures

Fla Keys Luxury Houseboat, Prime Location-Steps to Fun, Food & Water Adventures
Tavernier
9.8 out of 10, Exceptional, (219 reviews)
"Our host was amazing! Great location with lots to do! "
United States
Jamie B.
The price is NZ$919
includes taxes & fees
7 July - 8 July
Fla Keys Luxury Houseboat, Prime Location-Steps to Fun, Food & Water Adventures

Coastal Studio Getaway – Second Floor with Partial Water Views

Coastal Studio Getaway – Second Floor with Partial Water Views
Matecumbe
9.6 out of 10, Exceptional, (7 reviews)
"laid back and comfortable. "
United States
Joe M.
The price is NZ$590
includes taxes & fees
13 July - 14 July
Coastal Studio Getaway – Second Floor with Partial Water Views

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$1,087
includes taxes & fees
3 Aug - 4 Aug
Villa 5028 on Duck Key Boat Slip Available - 2BD 2.5BA

Resort Suite with Marina Views, Pool & Free Breakfast

Resort Suite with Marina Views, Pool & Free Breakfast
Marathon
The price is NZ$699
includes taxes & fees
8 July - 9 July
Resort Suite with Marina Views, Pool & Free Breakfast

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 NZ$1,853
includes taxes & fees
12 July - 13 July
Lovely Water View! 3 Bed, 3 BA Townhome, Cabana Club: Oceanfront Beach, Pool!

The Islands of Islamorada

The Islands of Islamorada
4.0 star property
Matecumbe
9.6 out of 10, Exceptional, (77 reviews)
"What a wonderful venue for our last 2 nights in the Keys. This place is a hidden gem. The entire staff, especially Edith, the bartender, were fantastic."
United States
Michael
The price is NZ$1,355
includes taxes & fees
7 July - 8 July
The Islands of Islamorada

Waterfront Suite with Pool, Tiki Bar & Marina

Waterfront Suite with Pool, Tiki Bar & Marina
Marathon
The price is NZ$739
includes taxes & fees
8 July - 9 July
Waterfront Suite with Pool, Tiki Bar & Marina
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, 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 NZ$207 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. 

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 33 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 Sombrero 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.