Islamorada Holiday Rentals

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Holiday Rentals in Islamorada

Treasure Harbor
3.0 star property
8.8 out of 10, Excellent, (108)
"If you are looking for a laid back vibe with no hassle here is the place. Friendly staff. Aqualodge was cute and comfortable. Easily rented a boat for the day...found great snorkeling and beautiful views. "
The price is AU$387
includes taxes & fees
20 Oct - 21 Oct
Treasure Harbor
Breezy Palms Resort
2.5 star property
8.8 out of 10, Excellent, (545)
"Spacious rooms and location was great for what we needed. "
The price is AU$188
includes taxes & fees
22 Oct - 23 Oct
Breezy Palms Resort
Charming Home in Key Largo
9.8 out of 10, Exceptional, (25)
"Great location. Very clean very nice, stay there again"
The price is AU$541
includes taxes & fees
17 Oct - 18 Oct
Charming Home in Key Largo
Serenity In The Sun Condo Fabulous Ocean View
10.0 out of 10, Exceptional, (106)
"Very comfortable and clean. So attractive and was furnished with all the little extras! Owner was very helpful with suggestions for dining and activities. "
The price is AU$620
includes taxes & fees
2 Nov - 3 Nov
Serenity In The Sun Condo Fabulous Ocean View
Aqua Vista Ocean Pointe 3307
2.5 star property
10.0 out of 10, Exceptional, (1)
"Beautiful & perfect place for a getaway. Really enjoyed our stay. Highly recommend."
The price is AU$671
includes taxes & fees
19 Oct - 20 Oct
Aqua Vista Ocean Pointe 3307
Coastal comfort in Ocean Pointe Suites.
10.0 out of 10, Exceptional, (33)
"Very clean, lots of things to do for the kids on property - large pool and hot tub, tennis and pickle ball courts, and a small beach. "
The price is AU$849
includes taxes & fees
20 Oct - 21 Oct
Coastal comfort in Ocean Pointe Suites.
Sea View Farm Style Ocean front Condo Views
10.0 out of 10, Exceptional, (151)
"We had a great stay at this property. Everything was very clean and I loved the decor!"
The price is AU$603
includes taxes & fees
2 Nov - 3 Nov
Sea View Farm Style Ocean front Condo Views
1BR w/ Pool, Beach, Near Marine & Bird Sanctuaries
2.0 star property
The price is AU$364
includes taxes & fees
28 Oct - 29 Oct
1BR w/ Pool, Beach, Near Marine & Bird Sanctuaries
Island Bay Resort
2.5 star property
10.0 out of 10, Exceptional, (132)
"Clean, friendly, has its own beach"
The price is AU$417
includes taxes & fees
27 Oct - 28 Oct
Island Bay Resort
Boho Style Florida Keys Condo Ocean Views
9.8 out of 10, Exceptional, (43)
"Unit was extremely clean, nicely furnished, easy to access and owners were very responsive. The property including pool area and small beach were lovely and very well maintained."
The price is AU$627
includes taxes & fees
19 Oct - 20 Oct
Boho Style Florida Keys Condo Ocean Views
Florida Keys Luxury Houseboat, Unique living on the Water WiFi
9.8 out of 10, Exceptional, (209)
"Excellent and very relaxing"
The price is AU$641
includes taxes & fees
31 Oct - 1 Nov
Florida Keys Luxury Houseboat, Unique living on the Water WiFi
Ocean View Gem Ocean Pointe 3406 2BA/2BR King/Queen
2.0 star property
10.0 out of 10, Exceptional, (3)
"Great place! Condo was clean l and was as described. Property and pool area was fun and very clean."
The price is AU$666
includes taxes & fees
21 Oct - 22 Oct
Ocean View Gem Ocean Pointe 3406 2BA/2BR King/Queen
Sunrise Sanctuary - Top Floor Ocean Pointe 2415
9.6 out of 10, Exceptional, (11)
"Nice place and would definitely recomend."
The price is AU$647
includes taxes & fees
19 Oct - 20 Oct
Sunrise Sanctuary - Top Floor Ocean Pointe 2415
Reel Large END Unit in Ocean Pointe Suites - Newly Renovated!
9.4 out of 10, Exceptional, (17)
"We love our family vacations there."
The price is AU$898
includes taxes & fees
17 Oct - 18 Oct
Reel Large END Unit in Ocean Pointe Suites - Newly Renovated!
Island Sanctuary Islamorada
9.8 out of 10, Exceptional, (11)
"It exceeded our expectations, and we are so glad we found this location!"
The price is AU$652
includes taxes & fees
17 Oct - 18 Oct
Island Sanctuary Islamorada
Toes in the Sand - 2 Bedroom Condo Sleeps 4
10.0 out of 10, Exceptional, (27)
"A great first stop on our trip to the Keys! Instructions were great and the condo was very nice."
The price is AU$586
includes taxes & fees
27 Oct - 28 Oct
Toes in the Sand - 2 Bedroom Condo Sleeps 4
Paradise Palms 2 Bedroom Condo Ocean Pointe 1206
9.6 out of 10, Exceptional, (5)
"Thanks for your great hospitality."
The price is AU$651
includes taxes & fees
19 Oct - 20 Oct
Paradise Palms 2 Bedroom Condo Ocean Pointe 1206
Boho Chic Ocean Pointe 3214
10.0 out of 10, Exceptional, (12)
"It was clean, well organized and communication was great. Had a good time."
The price is AU$671
includes taxes & fees
19 Oct - 20 Oct
Boho Chic Ocean Pointe 3214
Blue Haven Key Largo | Ocean Pointe 1315
9.6 out of 10, Exceptional, (14)
"Loved this condo. Had all the amenities we needed and was super clean and tidy. Will definitely be staying here again. "
The price is AU$666
includes taxes & fees
27 Oct - 28 Oct
Blue Haven Key Largo | Ocean Pointe 1315
2. Waterfront Retreat w/ Ocean Access, Key Largo!
10.0 out of 10, Exceptional, (14)
"My second time staying there and I will stay there in the near future! Love this place!"
The price is AU$487
includes taxes & fees
19 Oct - 20 Oct
2. Waterfront Retreat w/ Ocean Access, Key Largo!
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 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$188 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?

BeachFront Paradise/By The Glam Homes: This highly rated holiday home rental in Islamorada offers a balcony, a garden and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a microwave, so that you can cook with friends or family. Make the most of Access to hot tub in this rental home to help you unwind. Some other homes for rent in Islamorada include Iconic Ted Williams Estate. Bayfront, Heated Infinity Pool & Hot Tub, Dockage. and Next availability from May 18th, 2024 - The Last Resort, Islamorada - MM76.7.

How many holiday rentals are there in Islamorada?

With 487 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 Islamorada County 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 Bud n' Mary's Dive Center and Fiesta Key.

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.