Islamorada Holiday Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

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

Our top choices for Islamorada holiday rentals

Treasure Harbor

Treasure Harbor
3.0 star property
Islamorada
9.0 out of 10, Wonderful, (127 reviews)
"Very peaceful and comfortable stay! Dallas and Hannah were amazing hosts! Thank you so much !"
United States
Nick
Treasure Harbor

Breezy Palms Resort

Breezy Palms Resort
2.5 star property
Matecumbe
8.8 out of 10, Excellent, (615 reviews)
"Friendly staff, beautiful peaceful beach, great room with a big comfy bed and all that you might need. "
United States
Alexander
The price is AU$346
includes taxes & fees
1 Feb - 2 Feb
Breezy Palms Resort

Amazing Ocean view condo

Amazing Ocean view condo
Tavernier
9.6 out of 10, Exceptional, (43 reviews)
"Exceeded expectations, exceptionally clean, great for kids (they loved the pool), perfect for our Keys trip"
United States
Natalie M.
The price is AU$558
includes taxes & fees
4 Feb - 5 Feb
Amazing Ocean view condo

Blue Haven Key Largo | Ocean Pointe 1315

Blue Haven Key Largo | Ocean Pointe 1315
Tavernier
9.6 out of 10, Exceptional, (15 reviews)
"Loved this condo. Had all the amenities we needed and was super clean and tidy. Will definitely be staying here again. "
United States
Rodney B.
The price is AU$598
includes taxes & fees
3 Feb - 4 Feb
Blue Haven Key Largo | Ocean Pointe 1315

Island Sanctuary Islamorada

Island Sanctuary Islamorada
Tavernier
9.8 out of 10, Exceptional, (14 reviews)
"It exceeded our expectations, and we are so glad we found this location!"
United States
Jenn H.
The price is AU$594
includes taxes & fees
11 Feb - 12 Feb
Island Sanctuary Islamorada

Florida Keys Getaway - Slps 4 - Ocean View

Florida Keys Getaway - Slps 4 - Ocean View
Tavernier
9.6 out of 10, Exceptional, (20 reviews)
"Everything was just as described in the condo listing. We enjoyed the pool and hot tub. Wonderful location to explore the Keys. "
United States
Michele G.
The price is AU$606
includes taxes & fees
25 Feb - 26 Feb
Florida Keys Getaway - Slps 4 - Ocean View

Keys Bohemian 2 BR 2 BA at Ocean Pointe 1312

Keys Bohemian 2 BR 2 BA at Ocean Pointe 1312
Tavernier
The price is AU$684
includes taxes & fees
2 Feb - 3 Feb
Keys Bohemian 2 BR 2 BA at Ocean Pointe 1312

Sunrise Oasis - Top Floor 2 BR 2 BA Condo 2411

Sunrise Oasis - Top Floor 2 BR 2 BA Condo 2411
Tavernier
10.0 out of 10, Exceptional, (5 reviews)
"Great location and clean"
United States
Matthew H.
The price is AU$649
includes taxes & fees
2 Feb - 3 Feb
Sunrise Oasis - Top Floor 2 BR 2 BA Condo 2411

Paradise Palms 2 Bedroom Condo Ocean Pointe 1206

Paradise Palms 2 Bedroom Condo Ocean Pointe 1206
Tavernier
9.6 out of 10, Exceptional, (5 reviews)
"Thanks for your great hospitality."
United States
richard
The price is AU$630
includes taxes & fees
3 Feb - 4 Feb
Paradise Palms 2 Bedroom Condo Ocean Pointe 1206

Serenity In The Sun Condo Fabulous Ocean View

Serenity In The Sun Condo Fabulous Ocean View
Tavernier
10.0 out of 10, Exceptional, (108 reviews)
"Fantastic place to stay! Very clean and great hosts. Will stay again. "
United States
Les
The price is AU$680
includes taxes & fees
31 Jan - 1 Feb
Serenity In The Sun Condo Fabulous Ocean View

Private 1-bedroom apartment in peaceful Tavernier with kitchen, key Largo

Private 1-bedroom apartment in peaceful Tavernier with kitchen, key Largo
Tavernier
10.0 out of 10, Exceptional, (2 reviews)
"Host was very helpful and place was very nice and very clean. Would definitely recommend. "
United States
Amy E.
The price is AU$538
includes taxes & fees
30 Jan - 31 Jan
Private 1-bedroom apartment in peaceful Tavernier with kitchen, key Largo

Lazy Daze Double King Suite Ocean Pointe 2310

Lazy Daze Double King Suite Ocean Pointe 2310
Tavernier
9.8 out of 10, Exceptional, (26 reviews)
"Everything was exceptionally nice. Would definitely book again."
United States
Sharon
The price is AU$746
includes taxes & fees
4 Feb - 5 Feb
Lazy Daze Double King Suite Ocean Pointe 2310

Aqua Vista Ocean Pointe 3307

Aqua Vista Ocean Pointe 3307
Tavernier
10.0 out of 10, Exceptional, (1 review)
"Beautiful & perfect place for a getaway. Really enjoyed our stay. Highly recommend."
United States
Michelle
The price is AU$639
includes taxes & fees
1 Feb - 2 Feb
Aqua Vista Ocean Pointe 3307

Casa Largo

Casa Largo
Key Largo
9.0 out of 10, Wonderful, (129 reviews)
"Very nice updated home in a nice community with views to the lagoon. Would definitely stay here again!"
United States
Priscilla G.
The price is AU$834
includes taxes & fees
2 Feb - 3 Feb
Casa Largo

Charming Home in Key Largo

Charming Home in Key Largo
Key Largo
9.8 out of 10, Exceptional, (30 reviews)
"Great location. Very clean very nice, stay there again"
United States
Mark B.
The price is AU$712
includes taxes & fees
12 Feb - 13 Feb
Charming Home in Key Largo

Sea View Farm Style Ocean front Condo Views

Sea View Farm Style Ocean front Condo Views
Tavernier
10.0 out of 10, Exceptional, (158 reviews)
"The property was excellent."
United States
June M.
The price is AU$728
includes taxes & fees
1 Feb - 2 Feb
Sea View Farm Style Ocean front Condo Views

Starfish Seas Ocean Pointe 1302 King/Queen 2BA 2BR

Starfish Seas Ocean Pointe 1302 King/Queen 2BA 2BR
Tavernier
9.8 out of 10, Exceptional, (26 reviews)
"Accommodation and location are excellent! Listing is accurate and the resort amenities are very enjoyable after a day out exploring the Keys (or just having at least one whole day at the resort, as we did). "
United States
Jenny G.
The price is AU$693
includes taxes & fees
8 Feb - 9 Feb
Starfish Seas Ocean Pointe 1302 King/Queen 2BA 2BR

Boho Style Florida Keys Condo Ocean Views

Boho Style Florida Keys Condo Ocean Views
Tavernier
9.8 out of 10, Exceptional, (44 reviews)
"Would stay there again."
Canada
jamie g.
The price is AU$762
includes taxes & fees
2 Feb - 3 Feb
Boho Style Florida Keys Condo Ocean Views

Top Floor w Amazing Ocean Views!! Resort Style Pool, Beach, Marina, & Cafe!

Top Floor w Amazing Ocean Views!! Resort Style Pool, Beach, Marina, & Cafe!
Tavernier
10.0 out of 10, Exceptional, (2 reviews)
"The property was just as pictured on the site! We loved the view from the balconies (yes, two!!!). The host was superior in supplying our basic needs upon arrival. More importantly, she was extremely responsive to our questions during our stay (usually responding within a few minutes--even on Christmas day!!). The property is conveniently located in the keys so it's not too far to Miami or Key West. We absolutely loved our stay! If we come back to the Keys, we will definitely stay here again!!!"
United States
Mark W.
The price is AU$578
includes taxes & fees
3 Feb - 4 Feb
Top Floor w Amazing Ocean Views!! Resort Style Pool, Beach, Marina, & Cafe!

Ocean View Gem Ocean Pointe 3406 2BA/2BR King/Queen

Ocean View Gem Ocean Pointe 3406 2BA/2BR King/Queen
Tavernier
10.0 out of 10, Exceptional, (3 reviews)
"Great place! Condo was clean l and was as described. Property and pool area was fun and very clean."
United States
Kevin W.
The price is AU$731
includes taxes & fees
2 Feb - 3 Feb
Ocean View Gem Ocean Pointe 3406 2BA/2BR King/Queen
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 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 Islamorada 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 Islamorada holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Islamorada holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Islamorada 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 Islamorada holiday rentals we have selected for you start as low as AU$346 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Islamorada rentals

At Expedia, we put the best Islamorada 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 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 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 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. 

Frequently asked questions

Can I find a holiday rental in Islamorada?

Yes, there are holiday rentals close to the most popular sights in Islamorada, or you can select a more secluded option if you're looking for 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 holiday rentals that Islamorada has to offer?

CHARMING WATERFRONT OCEANSIDE CANAL HOME-LARGE PROTECTED DOCKAGE-WiFi-SMART TVs.: This highly rated holiday home rental in Islamorada is located by the ocean, and has a balcony, a garden and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games. Some other homes for rent in Islamorada include Bungalow #3 - 2 Bed/1 Bath & Pool in Islamorada and Next availability from May 18th, 2024 - The Last Resort, Islamorada - MM76.7.

How many holiday rentals are there in Islamorada?

With 480 Expedia holiday rentals, you're guaranteed to find just the right place for your Islamorada stay.

What can I see and do in Islamorada?

Enjoy the outdoors at Everglades National Park and Anne's Beach, or simply take in cultural attractions like History of Diving Museum and MoradaWay Arts & Cultural District. Other places in town to visit include Florida Keys Brewing Co. and Bud n' Mary's Dive Center.

What’s a holiday rental in Islamorada like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Islamorada. Holiday rentals feature extras like laundry facilities and kitchens so your stay will be comfortable. If you're concerned about a sanitised environment, holiday rentals can offer a sense of privacy away from shared hotel lifts and bustling concierge desks while still allowing you the experience of travel. You'll also get more space in a holiday rental than in a hotel, which makes a holiday rental a great option for family trips.