Long Key Holiday Rentals

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Check prices for these dates

Tonight
30 Dec - 31 Dec
Tomorrow
31 Dec - 1 Jan
This weekend
2 Jan - 4 Jan
Next weekend
9 Jan - 11 Jan

Our top choices for Long Key holiday rentals

25-inch flat-screen TV with digital channels, TV
Treasure Harbor

Houseboat in Islamorada

Treasure Harbor
3.0 star property
9.0 out of 10, Wonderful, (120)
"Great spot! Will be back someday hopefully. "
Canada
Diane
Treasure Harbor
Exterior
Tropical Cottages

Cottage in Marathon

Tropical Cottages
3.0 star property
8.6 out of 10, Excellent, (914)
"Decent stay, easy check in and contactless checkout. Very quiet and nice place! "
United States
Swastik
The price is HK$1,127
HK$1,268 total
includes taxes & fees
11 Jan - 12 Jan 2026
Tropical Cottages
42-inch Smart TV with digital channels, Netflix, Hulu
Yacht Haven Marina

Houseboat in Marathon

Yacht Haven Marina
3.5 star property
9.8 out of 10, Exceptional, (245)
"Friendly staff and extremely clean."
United States
Travis
Yacht Haven Marina
Premium bedding, soundproofing, iron/ironing board, free WiFi
Knight's Key Suites

Aparthotel in Marathon

Knight's Key Suites
3.0 star property
9.0 out of 10, Wonderful, (1158)
"Very good location.. Clean room."
United States
Leonor
The price is HK$941
HK$1,225 total
includes taxes & fees
15 Jan - 16 Jan 2026
Knight's Key Suites
Exterior
Breezy Palms Resort

Aparthotel in Matecumbe

Breezy Palms Resort
2.5 star property
8.8 out of 10, Excellent, (600)
"Property was nice and easy to navigate, ocean view room was extra nice to have!"
United States
Lisa
The price is HK$1,188
HK$1,740 total
includes taxes & fees
8 Jan - 9 Jan 2026
Breezy Palms Resort
BBQ/picnic Area
Aqua Lodge Rentals At Coconut Cay

Houseboat in Marathon

Aqua Lodge Rentals At Coconut Cay
3.5 star property
9.6 out of 10, Exceptional, (200)
"A unique and interesting place to vacation. Relaxing yet close enough to things to do. I highly recommend the Aqua Loge rentals as a place to stay."
United States
Keith
Aqua Lodge Rentals At Coconut Cay
Property grounds
Fla Keys Luxury Houseboat, Prime Location-Steps to Fun, Food & Water Adventures

Houseboat in Tavernier

Fla Keys Luxury Houseboat, Prime Location-Steps to Fun, Food & Water Adventures
9.8 out of 10, Exceptional, (210)
"Heidi has a little bit of paradise on her houseboat! You must plan on staying!!"
United States
Toni M.
The price is HK$2,332
HK$3,895 total
includes taxes & fees
11 Jan - 12 Jan 2026
Fla Keys Luxury Houseboat, Prime Location-Steps to Fun, Food & Water Adventures
2 outdoor pools, open 8:00 AM to 6:00 PM, pool loungers
The Islands of Islamorada

Villa in Matecumbe

The Islands of Islamorada
4.0 star property
9.8 out of 10, Exceptional, (70)
"Great for family vacation with kids. love it"
United States
Dixania
The price is HK$4,733
HK$5,753 total
includes taxes & fees
7 Jan - 8 Jan 2026
The Islands of Islamorada
Marina
Skipjack Resort & Marina

Aparthotel in Marathon

Skipjack Resort & Marina
3.0 star property
8.6 out of 10, Excellent, (1218)
"Beautiful location clean rooms friendly staff "
United States
Tiffany
Skipjack Resort & Marina
Property grounds
1.5 Bedroom, 1 bath with back deck. Pet friendly with 2 Queen and 2 twin beds.

Houseboat in Tavernier

1.5 Bedroom, 1 bath with back deck. Pet friendly with 2 Queen and 2 twin beds.
10.0 out of 10, Exceptional, (2)
"The property manager was SO nice. She made sure we were comfortable as we brought a big dog. They made sure that the boat we chose was big enough for us! This was a super fun stay. We would absolutely stay here again. "
United States
Hannah B.
The price is HK$2,915
HK$3,591 total
includes taxes & fees
3 Jan - 4 Jan 2026
1.5 Bedroom, 1 bath with back deck. Pet friendly with 2 Queen and 2 twin beds.
Property grounds
Villa 5053 on Duck Key Boat Slip Available - 2BD 2.5BA

Holiday Home in Duck Key

Villa 5053 on Duck Key Boat Slip Available - 2BD 2.5BA
9.6 out of 10, Exceptional, (46)
"Clean property! Great views! Great communication with owner! Perfect location- close to marathon and key west! "
United States
candi b.
The price is HK$2,202
HK$4,919 total
includes taxes & fees
5 Jan - 6 Jan 2026
Villa 5053 on Duck Key Boat Slip Available - 2BD 2.5BA
Fridge, microwave, oven, stovetop
Villa 5086 on Duck Key Boat Slip Available - 2BD 1.5BA

Villa in Duck Key

Villa 5086 on Duck Key Boat Slip Available - 2BD 1.5BA
8.6 out of 10, Excellent, (25)
"Great location! We enjoyed our time there."
United States
Erin T.
The price is HK$1,973
HK$4,691 total
includes taxes & fees
11 Jan - 12 Jan 2026
Villa 5086 on Duck Key Boat Slip Available - 2BD 1.5BA
Outdoor pool
Tropical Oasis on Sombrero Beach in the Heart of Marathon FL

Condo in Marathon

Tropical Oasis on Sombrero Beach in the Heart of Marathon FL
2.0 star property
9.0 out of 10, Wonderful, (4)
"Unit was very clean and recently remodeled. The building was a little difficult to find in the dark at night, but I would definitely recommend staying here again."
United States
Nancy M.
The price is HK$1,224
HK$3,024 total
includes taxes & fees
13 Jan - 14 Jan 2026
Tropical Oasis on Sombrero Beach in the Heart of Marathon FL
TV
Villa 5034 on Duck Key Boat Slip Available - 2BD 2.5BA

Villa in Duck Key

Villa 5034 on Duck Key Boat Slip Available - 2BD 2.5BA
10.0 out of 10, Exceptional, (4)
"Everything about the stay was nice. "
United States
Mario S.
The price is HK$2,202
HK$4,958 total
includes taxes & fees
8 Jan - 9 Jan 2026
Villa 5034 on Duck Key Boat Slip Available - 2BD 2.5BA
Exterior
Villa 5008 on Duck Key Boat Slip Available - 2BD 1.5BA

Villa in Duck Key

Villa 5008 on Duck Key Boat Slip Available - 2BD 1.5BA
10.0 out of 10, Exceptional, (1)
"The location was perfect, house was very clean, and the view was breathtaking. We will 100% return."
United States
Gina A.
The price is HK$2,712
HK$5,586 total
includes taxes & fees
15 Jan - 16 Jan 2026
Villa 5008 on Duck Key Boat Slip Available - 2BD 1.5BA
Exterior
Villa 5023 on Duck Key Boat Slip Available - 2BD 1.5BA

Holiday Home in Duck Key

Villa 5023 on Duck Key Boat Slip Available - 2BD 1.5BA
9.4 out of 10, Exceptional, (32)
"A short weekend getaway was made perfect in this villa. The location is idyllic; especially the balcony overlooking the bay with a perfect sunset view. The home was well-appointed, simple yet all the necessities were covered. Communication with the property manager was excellent. Definitely will book again. "
United States
Natasha A.
The price is HK$2,202
HK$4,802 total
includes taxes & fees
4 Jan - 5 Jan 2026
Villa 5023 on Duck Key Boat Slip Available - 2BD 1.5BA
Property grounds
Villa 7075 on Duck Key Boat Slip Available - 2BD 2.5BA

Villa in Marathon

Villa 7075 on Duck Key Boat Slip Available - 2BD 2.5BA
9.2 out of 10, Wonderful, (30)
"Wonderful experience, great views, clean rooms, great amount of space. Great price"
United States
Race
The price is HK$2,202
HK$4,872 total
includes taxes & fees
13 Jan - 14 Jan 2026
Villa 7075 on Duck Key Boat Slip Available - 2BD 2.5BA
1 bedroom, iron/ironing board, free WiFi, bed sheets
Waterfront Fun: Pool, Marina, Tiki Bar & Beach!

Condo in Marathon

Waterfront Fun: Pool, Marina, Tiki Bar & Beach!
9.6 out of 10, Exceptional, (18)
"Very cute place, clean, everything we needed was provided. Great view of the bay and short distance to anything you need. Would recommend & stay again if we came back!"
United States
Lindsey T.
The price is HK$1,625
HK$3,489 total
includes taxes & fees
5 Jan - 6 Jan 2026
Waterfront Fun: Pool, Marina, Tiki Bar & Beach!
Property grounds
Charming 2-bedroom house in Marathon with pool

Holiday Home in Marathon

Charming 2-bedroom house in Marathon with pool
8.0 out of 10, Very good, (2)
"Great Home & Location & Enjoyable Stay! Thanks!"
United States
James J.
The price is HK$2,155
HK$5,662 total
includes taxes & fees
12 Jan - 13 Jan 2026
Charming 2-bedroom house in Marathon with pool
Beach
Tiny Villa, Big Ocean Views| Breathtaking Sunsets

Holiday Home in Duck Key

Tiny Villa, Big Ocean Views| Breathtaking Sunsets
10.0 out of 10, Exceptional, (13)
"Beautiful views. Very nice accommodations. Wonderfull location!"
United States
michael h.
The price is HK$2,441
HK$5,028 total
includes taxes & fees
7 Jan - 8 Jan 2026
Tiny Villa, Big Ocean Views| Breathtaking Sunsets
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

Amara Cay Resort

Amara Cay Resort

10/10 Excellent
"Was very nice , Did order cookies and brownies for the room Christmas night and that never happened! Fishing pole rental was ridiculous Food was great and good Keylime dessert ! "
Kathryn 3-night trip
Posted 2 days ago
Amara Cay Resort

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:

  • View our selection of featured holiday rentals in Long Key
  • Use the map to find apartments and other holiday homes in the Long Key neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Long Key while they last

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

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?

The Hammocks at Marathon: 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. You and your friends and family can relax into your holiday with amenities such as 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 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.