A beach with white lounge chairs, a covered pavilion, and palm trees.

Islamorada Vacation Rentals

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals
  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings
  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Islamorada vacation rentals

1. Breezy Palms Resort

Breezy Palms Resort
2.5 star property
Matecumbe
8.8 out of 10, Excellent, (737 reviews)
"Good location"
United States
Orlando
$130 nightly
The price is $146
Sep 6 - Sep 7
Total with taxes and fees
Breezy Palms Resort

2. Treasure Harbor

Treasure Harbor
3.0 star property
Islamorada
9.0 out of 10, Wonderful, (173 reviews)
"We loved sitting in the deck in the evening and again in the morning."
Canada
Molly
$274 nightly
The price is $308
Sep 2 - Sep 3
Total with taxes and fees
Treasure Harbor

3. Island Bay Resort

Island Bay Resort
2.5 star property
Tavernier
10.0 out of 10, Exceptional, (179 reviews)
"Very pleased with our stay"
United States
Vernon Micheal
$227 nightly
The price is $256
Sep 29 - Sep 30
Total with taxes and fees
Island Bay Resort

4. Anchorage Resort & Yacht Club

Anchorage Resort & Yacht Club
3.0 star property
Key Largo
8.8 out of 10, Excellent, (342 reviews)
"Great place "
United States
Jay
$210 nightly
The price is $236
Sep 2 - Sep 3
Total with taxes and fees
Anchorage Resort & Yacht Club

5. Yacht Haven Marina

Yacht Haven Marina
3.5 star property
Marathon
9.8 out of 10, Exceptional, (354 reviews)
"Fantastic place! It was super clean and looked just like the photos. We would stay here again!"
United States
Clara
$223 nightly
The price is $251
Sep 2 - Sep 3
Total with taxes and fees
Yacht Haven Marina

6. Skipjack Resort & Marina

Skipjack Resort & Marina
3.0 star property
Marathon
8.6 out of 10, Excellent, (1,289 reviews)
"Great spot"
Canada
Justin
$163 nightly
The price is $184
Sep 16 - Sep 17
Total with taxes and fees
Skipjack Resort & Marina

7. Tropical Cottages

Tropical Cottages
3.0 star property
Marathon
8.6 out of 10, Excellent, (998 reviews)
"A/c was amazing, clean and beautiful cabins."
Canada
Natasha
$95 nightly
The price is $107
Sep 2 - Sep 3
Total with taxes and fees
Tropical Cottages

8. Aqua Lodge Rentals At Coconut Cay

Aqua Lodge Rentals At Coconut Cay
3.5 star property
Marathon
9.6 out of 10, Exceptional, (232 reviews)
"Cleanness relaxing location, nice views, good air conditioning"
United States
Hakan
$228 nightly
The price is $256
Sep 2 - Sep 3
Total with taxes and fees
Aqua Lodge Rentals At Coconut Cay

9. Kings Kamp

Kings Kamp
2.5 star property
Key Largo
8.6 out of 10, Excellent, (41 reviews)
"It was very nice!!"
United States
Michelle
$195 nightly
The price is $220
Sep 2 - Sep 3
Total with taxes and fees
Kings Kamp

10. Premium Floating Bungalow by Stay Ombi

Premium Floating Bungalow by Stay Ombi
3.5 star property
Key Largo
9.6 out of 10, Exceptional, (4 reviews)
"Great experience ! Will do it again"
United States
Deivys
$914 nightly
The price is $1,029
Sep 7 - Sep 8
Total with taxes and fees
Premium Floating Bungalow by Stay Ombi
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

Top Islamorada Hotel Reviews

Find out more about Islamorada

Everything you need to know about Islamorada 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 Islamorada 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 Islamorada vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Islamorada vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Islamorada. 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 Islamorada 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 $146 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 Islamorada rentals

At Expedia, we put the best Islamorada 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 Islamorada 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 Islamorada 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 Islamorada. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

Frequently asked questions

Can I find a vacation rental in Islamorada?

Yes, we have vacation rentals in Islamorada close to MoradaWay Arts & Cultural District, or you can select a secluded option if you want a relaxing stay. Visitors to Islamorada like the scenic seaside and entertainment choices this destination is known for. While you're here, grab a bite or have a drink at the seafood restaurants.

What are some of the best vacation home rentals that Islamorada has to offer?

7 Bedroom with Dockage, Pool, Firepit, Paddle Boards & Kayaks : This Islamorada vacation home rental is located by the ocean and has an outdoor pool, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 7 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Some other homes for rent in Islamorada include Private Beachfront Paradise and Bungalow #4 - 2 Bed/1 Bath & Pool in Islamorada.

How many vacation rentals are there in Islamorada?

With 403 Expedia vacation rentals, you're sure to find just the right place for your Islamorada stay.

What can I see and do in Islamorada?

Islamorada County Park and Founders Park are a couple of scenic spots to enjoy the outdoors, whereas History of Diving Museum is one of the cultural attractions. Other places in town to visit include Bud n' Mary's Dive Center and Robbie’s of Islamorada.

What’s a vacation rental in Islamorada like?

A vacation rental is a private property where you can stay for a couple of days or more in Islamorada. Vacation rentals provide amenities such as kitchens and laundry facilities so you'll have a home away from home. If you're concerned about cleanliness, a vacation rental can provide a sense of safety away from shared hotel elevators and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a traditional hotel, which makes a vacation rental a popular option for family trips or small group gatherings.