Long Key Vacation Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
Aug 26 - Aug 27
Tomorrow
Aug 27 - Aug 28
This weekend
Aug 29 - Aug 31
Next weekend
Sep 5 - Sep 7

Vacation Rentals in Long Key

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

Treasure Harbor

3.0 star property
8.8 out of 10, Excellent, (102)
"Unique House boat experience, friendly staff. "
The price is ￥13,224
￥35,542 total
includes taxes & fees
Sep 2 - Sep 3
Treasure Harbor
Breezy Palms Resort
Exterior

Breezy Palms Resort

2.5 star property
8.8 out of 10, Excellent, (518)
"Best kept secret, love staying here,!"
The price is ￥11,360
￥20,438 total
includes taxes & fees
Sep 15 - Sep 16
Breezy Palms Resort
Yacht Haven Marina
42-inch Smart TV with digital channels, Netflix, Hulu

Yacht Haven Marina

3.5 star property
9.8 out of 10, Exceptional, (197)
"We loved our weekend stay here. "
Yacht Haven Marina
Cabins at Bonefish Bay
Deluxe Bungalow | Terrace/patio

Cabins at Bonefish Bay

3.0 star property
9.8 out of 10, Exceptional, (60)
"Awesome cabins!"
Cabins at Bonefish Bay
Tropical Cottages
Exterior

Tropical Cottages

3.0 star property
8.6 out of 10, Excellent, (855)
"Wish check in was sooner but made out well, very quiet, personal parking, food truck near by and was all around a good stay"
The price is ￥11,818
￥13,295 total
includes taxes & fees
Aug 27 - Aug 28
Tropical Cottages
Skipjack Resort & Marina
Marina

Skipjack Resort & Marina

3.0 star property
8.6 out of 10, Excellent, (1199)
"Great stay"
Skipjack Resort & Marina
Private Island ~Oceanfront-Fishing-Diving~ FL Keys
Exterior

Private Island ~Oceanfront-Fishing-Diving~ FL Keys

10.0 out of 10, Exceptional, (20)
"We had a great relaxing and quiet vacation with great views and daily visits by dolphins, turtles and resident iguanas. Great place to get away from it all."
Private Island ~Oceanfront-Fishing-Diving~ FL Keys
The Islands of Islamorada
2 outdoor pools, open 8:00 AM to 6:00 PM, sun loungers

The Islands of Islamorada

4.0 star property
9.8 out of 10, Exceptional, (66)
"Absolutely outstanding resort. Legitimate 5 star property. "
The price is ￥80,817
￥99,020 total
includes taxes & fees
Sep 5 - Sep 6
The Islands of Islamorada
Knight's Key Suites
1 bedroom, premium bedding, soundproofing, iron/ironing board

Knight's Key Suites

3.0 star property
9.0 out of 10, Wonderful, (1142)
"Nice roomy accommodations and helpful staff I would stay here again "
The price is ￥10,286
￥14,731 total
includes taxes & fees
Sep 8 - Sep 9
Knight's Key Suites
The Hammocks at Marathon
Outdoor pool, pool umbrellas, sun loungers

The Hammocks at Marathon

2.5 star property
9.0 out of 10, Wonderful, (98)
"Very nice and clean nice pool area nice tity bar an restant easy to get in and out good gym area"
The Hammocks at Marathon
Aqua Lodge Rentals At Coconut Cay
BBQ/picnic area

Aqua Lodge Rentals At Coconut Cay

3.5 star property
9.6 out of 10, Exceptional, (178)
"Very very nice place"
Aqua Lodge Rentals At Coconut Cay
Aqua Lodges at 47th Street Gulfside
Deluxe Cabin, Lagoon View | Private kitchen | Toaster, dining tables

Aqua Lodges at 47th Street Gulfside

3.0 star property
8.6 out of 10, Excellent, (50)
"10/10 property and boat was clean. It was perfect for my family with 2 littles. "
Aqua Lodges at 47th Street Gulfside
Piece of Paradise located at Hawks Cay in Duck Key
Pool

Piece of Paradise located at Hawks Cay in Duck Key

9.4 out of 10, Exceptional, (3)
"Amazing place. "
Piece of Paradise located at Hawks Cay in Duck Key
Fishing and Family Fun paradise Oceanfront 60'ft dock 3 bed 2bath private pool
Outdoor pool, a heated pool

Fishing and Family Fun paradise Oceanfront 60'ft dock 3 bed 2bath private pool

10.0 out of 10, Exceptional, (32)
"We had a wonderful time watching marine life from the sea wall. Manatees cruised by daily!Part of the outdoor area is covered so if you need to get out of the sun it is perfect.The host communication was above and beyond too."
Fishing and Family Fun paradise Oceanfront 60'ft dock 3 bed 2bath private pool
Spacious Waterfront Home on a Direct Ocean Access Canal with a Chilled Pool
Property grounds

Spacious Waterfront Home on a Direct Ocean Access Canal with a Chilled Pool

9.4 out of 10, Exceptional, (72)
"Property was great for our group. 2 miles to grocery stores. Pool was great! Used the bikes and had a great time here. "
Spacious Waterfront Home on a Direct Ocean Access Canal with a Chilled Pool
Waterfront home with dock, pool table & private pool - walk to Sombrero Beach
A heated pool

Waterfront home with dock, pool table & private pool - walk to Sombrero Beach

8.8 out of 10, Excellent, (29)
"So enjoyed our stay here with a couple friends. Place has everything you need, is immaculate, fantastic view, and so close to either the beach in one direction and grocery stores in the other. Also located in a very nice residential neighborhood. Plan on returning! Thanks for the lovely stay!! "
Waterfront home with dock, pool table & private pool - walk to Sombrero Beach
One of the Best Private Beaches in US! Great Location fun activities-Fast Wifi!
Private beach, sun loungers, beach towels

One of the Best Private Beaches in US! Great Location fun activities-Fast Wifi!

10.0 out of 10, Exceptional, (201)
"The property was very clean and tidy. We thoroughly enjoyed our stay. The neighborhood was very quiet yet conveniently located near restaurants and other attractions. Highly recommend."
One of the Best Private Beaches in US! Great Location fun activities-Fast Wifi!
Water Front Condo in Duck Key. FREE WIFI! Overlooking the Gulf of Mexico.
Smart TV, fireplace

Water Front Condo in Duck Key. FREE WIFI! Overlooking the Gulf of Mexico.

9.6 out of 10, Exceptional, (57)
"Lovely location; lovely setting."
Water Front Condo in Duck Key. FREE WIFI! Overlooking the Gulf of Mexico.
Bungalow #4 - 2 Bed/1 Bath & Pool in Islamorada
Outdoor pool, a heated pool

Bungalow #4 - 2 Bed/1 Bath & Pool in Islamorada

9.6 out of 10, Exceptional, (31)
"Nice property . Well kept. Good management "
Bungalow #4 - 2 Bed/1 Bath & Pool in Islamorada
🌊 Private Oasis With Pool Spa Dock and Ocean right in your backyard 🌊 allow pets
Beach towels

🌊 Private Oasis With Pool Spa Dock and Ocean right in your backyard 🌊 allow pets

9.2 out of 10, Wonderful, (45)
"Great sunsets; quiet street; fantastic marine life. Frank was very responsive. The property is not brand new but delivered on what we needed: pool, great dock for fishing and keeping boat during day. Booked again for next year. "
🌊 Private Oasis With Pool Spa Dock and Ocean right in your backyard 🌊 allow pets
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Long Key Hotel Reviews

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

10/10 Excellent
"We were only there a couple of days but we had a great time! It's typical Key West layed back vibe!"
Karen 2-night trip
Posted 9 hours ago
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

Find out more about Long Key

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!

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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?

Piece of Paradise located at Hawks Cay in Duck Key: This vacation home rental near Long Key has air-conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a stovetop, and a microwave.

How many vacation rentals are there in Long Key?

Choose from 41 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.