Search Holiday Rentals in Long Key

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May 2 - May 3
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May 3 - May 4
This weekend
May 3 - May 5
Next weekend
May 10 - May 12

Top Holiday Rentals in Long Key

Standard Bungalow | Living area | 42-inch Smart TV with digital channels, Netflix, Hulu
Yacht Haven Marina
3.5 star property
10.0 out of 10, Exceptional, (42)
"Enjoyed coffee in the mornings on the porch facing the water. Had a great time. "
The price is £251
includes taxes & fees
16 May - 17 May
Yacht Haven Marina
Exclusive Cabin | Living area | Flat-screen TV
Cabins at Bonefish Bay
3.0 star property
10.0 out of 10, Exceptional, (8)
"Had a great time! Loved having so much room. The rest of the property was great and the entire staff was so friendly!! Close to restaurants, but also quietly nestled off the main highway. Just a real gem! Wish we could've stayed longer!! Will absolutely stay here again!"
Cabins at Bonefish Bay
Beach nearby, sun-loungers, beach towels
One of the Best Private Beaches in US! Great Location fun activities-Fast Wifi!
10.0 out of 10, Exceptional, (180)
"Beautiful property, well maintained and perfect location. It’s quiet and peaceful but close to some great restaurants and activities. All the stress just melted away! Thank you, Michael, for being a wonderful host!"
One of the Best Private Beaches in US! Great Location fun activities-Fast Wifi!
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Beach nearby
Life in Paradise w/ Boat Slip at #1 Rated Resort in Marathon - Coral Lagoon
10.0 out of 10, Exceptional, (189)
"This was a great vacation for my daughter's 18 birthday with some friends and family. We saw manatees the first morning out back in the canal. There was always some type of animal in the very sheltered canal if you have a boat. We brought our pontoon boat and had a day of very bad weather. We never worried once because we could see the boat from the back porch (50 yards away) and the canal is very sheltered and nice. You have access to the ocean and the bay side as soon as you go around the...
Life in Paradise w/ Boat Slip at #1 Rated Resort in Marathon - Coral Lagoon
Property grounds
Southern Diversion Estate-see our reduced rates
10.0 out of 10, Exceptional, (81)
"Our family takes an annual trip together, there were 17 of us this time. The property had something for everyone, best aspects are the sunsets and the infinity pool. The property manager was one of the best we've ever had- very responsive."
Southern Diversion Estate-see our reduced rates
Terrace/patio
COZY FAMILY HOME-POOL-HOTTUB -5 minute drive to sombrero beach-private property
10.0 out of 10, Exceptional, (27)
"This house is roomy, clean, and located perfectly in Marathon for anywhere in the Keys you may want to travel to. The hot tub, pool, and grill were well used by us all, and communication with the host was immediate and friendly. We will stay there again on next trip to the Florida Keys."
COZY FAMILY HOME-POOL-HOTTUB -5 minute drive to sombrero beach-private property
Beach nearby, beach towels
Canal Front Pool Home with Dockage, Jetted Pool, Tiki Hut, 2 Kayaks & 2 Bikes!
10.0 out of 10, Exceptional, (35)
"Very nice property, wonderful outdoor area to just relax at and look at the canal. We saw two manatees (Mom and Baby) just slowly swimming by. The house was great, very welcoming and comfortable and tastefully decorated with great furnishings."
Canal Front Pool Home with Dockage, Jetted Pool, Tiki Hut, 2 Kayaks & 2 Bikes!
Property grounds
Lovely oceanfront home with dock, deck, patio, WiFi, W/D, & AC - great view
9.8 out of 10, Exceptional, (6)
"Excellent"
Lovely oceanfront home with dock, deck, patio, WiFi, W/D, & AC - great view
Outdoor pool, a heated pool
Ocean front with private beach and pool
9.8 out of 10, Exceptional, (34)
"Great view Quiet and private setting Beach good for walking, not for swimming Nice pool Condo attractive, comfortable beds, kitchen well supplied, all appliances worked"
Ocean front with private beach and pool
Pool
P98 - 2698 Sombrero Blvd
9.8 out of 10, Exceptional, (8)
"We LOVED this home! Everything was spotless, looked new - just as pictured. The kitchen had everything you could need to cook. Each room had a bathroom and a TV. We were vacationing with our two little kids and the pool was perfect for them and we spent every minute out there enjoying the beautiful outdoors space. This is our 4th time renting in Marathon and this house was by far our favorite."
P98 - 2698 Sombrero Blvd
A heated pool
Gorgeous Getaway with a Lush Yard, Private Pool, & Free WiFi
9.8 out of 10, Exceptional, (16)
"Property very comfy. Beds were awesome. Pool was great."
Gorgeous Getaway with a Lush Yard, Private Pool, & Free WiFi
Front of property
Aqua Lodge Rentals At Coconut Cay
3.5 star property
9.6 out of 10, Exceptional, (101)
"Very clean, comfortable and relaxing. "
The price is £326
includes taxes & fees
21 May - 22 May
Aqua Lodge Rentals At Coconut Cay
Private beach
Oceanfront Sandy Beach Vacation Rental Unit 1
9.6 out of 10, Exceptional, (98)
"Was absolutely breath taking. Was a beautiful place to stay and was so homey. Highly recommended and hope to stay there again"
Oceanfront Sandy Beach Vacation Rental Unit 1
A heated pool
COZY COTTAGE WITH PRIVATE DIPPING POOL OVERLOOKING BLUE WATER LAGOON
9.6 out of 10, Exceptional, (60)
"Cute little townhouse, clean and well stocked. We live on the west coast of Florida, my daughter and her family were staying at Hawks Cay for 5 days. We decided to drive over and see them. The location was awesome for us, this townhome is on Hawks Cay property, we brought bikes which made it super convenient getting to and from the hotel. The yard is adorable, our dog enjoyed dropping & retrieving his toys from the spa/pool. We will definitely be back!"
COZY COTTAGE WITH PRIVATE DIPPING POOL OVERLOOKING BLUE WATER LAGOON
Signature House, 4 Bedrooms, Bay View (Manatee) | Beach/ocean view
Mangrove Marina and Resort Aqualodge Houseboats
3.0 star property
9.4 out of 10, Exceptional, (315)
"Absolutely beautiful! Cant wait to come back and stay here again."
Mangrove Marina and Resort Aqualodge Houseboats
Outdoor pool, pool loungers
Knight's Key Suites
3.0 star property
9.0 out of 10, Wonderful, (1024)
"The room was very clean and you are across a restaurant so don’t need to drive anywhere unless you want to."
The price is £142
includes taxes & fees
5 May - 6 May
Knight's Key Suites
On the beach
Casa De La Playa Oceanfront the Key to the Beach and 3 kayaks included
9.0 out of 10, Wonderful, (6)
"We had a great time on our family vacation at Casa De La Playa. We especially enjoyed the pool, pool toys, kayaks, back porch, and tropical landscaping. We also enjoyed using the beach toys and beach tent at area beaches."
Casa De La Playa Oceanfront the Key to the Beach and 3 kayaks included
Fridge, microwave, oven, stovetop
Two-story waterfront condo with patio, balconies & boating
9.0 out of 10, Wonderful, (86)
"The property was as listed! The check in process was easy and everything we needed was conveniently provided. The only issues we ran into were that we couldn’t get the tv’s to work properly. Otherwise it was the perfect place!"
Two-story waterfront condo with patio, balconies & boating
Fridge, microwave, oven, stovetop
Capt Craig's 1 Bedroom /1 Bath Apartment in Islamorada, Florida Keys
9.0 out of 10, Wonderful, (4)
"We had an excellent stay. Loved the place and look forward to staying here again in the future."
The price is £205
includes taxes & fees
7 May - 8 May
Capt Craig's 1 Bedroom /1 Bath Apartment in Islamorada, Florida Keys
Fridge, microwave, oven, stovetop
Waterfront retreat with balcony views, kayak, SUP, central AC & washer/dryer
9.0 out of 10, Wonderful, (35)
"This area is great and the homes are nice with ample room and all the things you need. The good parts are the views are amazing, kitchen is nicely stocked, beds are comfy, no bugs, nice pillows and nice decor. If your looking for just a nice house to stay at this is a great spot. There were only a few minor issues with the space, the dish washer did not work, after 3 days of trying I somehow got it to run once. I had seen this issue on previous reviews so it gave me some concern that this was...
Waterfront retreat with balcony views, kayak, SUP, central AC & washer/dryer
Don't see what you're looking for?
See all available properties in Long Key
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.

Long Key Holiday Rental Travel Info

Number of holiday rentals
29
Popular accommodation
Long Key private holiday homes
Known landmarks
Anne's Beach, Sunset Drive Beach and San Pedro Underwater Archaeological Preserve State Park
International airports
Miami, FL (MIA-Miami Intl.) and Key West, FL (EYW-Key West Intl.)

Other types of properties in Long Key you may be interested in

Exterior
Lime Tree Bay Resort
3.5 star property
9.0 out of 10, Wonderful, (1000)
"My husband and I stayed for one night for our anniversary. We got the studio suite across the street from the main property. We loved our stay for the 1 night - pool was nice, beachy areas were lovely. They have lots of amenities - outdoor chess, hammocks, paddle boards, kayaks, bikes, tennis courts and pickle ball… it’s never ending. Our only complaint would be that the studio is not really “across the street”- it’s across US1 and down a ways. We had to drive. Like I said, we didn’t mind at all...
The price is £184
includes taxes & fees
5 May - 6 May
Lime Tree Bay Resort
Private beach, white sand, sun-loungers, beach towels
Chesapeake Beach Resort
2.5 star property
9.0 out of 10, Wonderful, (1301)
"Amazing!"
The price is £198
includes taxes & fees
5 May - 6 May
Chesapeake Beach Resort
Private beach, sun-loungers, beach umbrellas, beach towels
Cheeca Lodge & Spa
4.0 star property
9.0 out of 10, Wonderful, (1004)
"Everything "
The price is £328
includes taxes & fees
16 May - 17 May
Cheeca Lodge & Spa
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.

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 £142 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?

Aqua Lodge Rentals At Coconut Cay: This holiday home rental outside of Long Key is located near the beach, and offers an outdoor pool, air conditioning and daily housekeeping to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a full-sized fridge, a stovetop and a microwave.

How many holiday rentals are there in Long Key?

Choose from 31 Expedia holiday rentals in Long Key for a memorable holiday.

What can I see and do in Long Key?

Fiesta Key and Long Key State Park are a couple of lovely local spots to get outside and enjoy nature. Anne's Beach and Bud n' Mary's Dive Center 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.

Recent reviews of Long Key properties
Expedia verified reviews

Chesapeake Beach Resort

Chesapeake Beach Resort

5/5 Excellent
"Amazing!"
A verified traveller stayed at Chesapeake Beach Resort
Posted 2 days ago
Chesapeake Beach Resort