Islamorada Holiday Rentals

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Our top choices for Islamorada holiday rentals

Treasure Harbor

Treasure Harbor
3.0 star property
Islamorada
9.0 out of 10, Wonderful, (117)
"I am obsessed with tiny houses and this one floats! It was so relaxing to sit on the deck and enjoy the view. The bed was very comfy and the gentle motion of the water put me right to sleep. The staff are friendly and helpful. Islamorada is beautiful and fun to explore."
United States
Mary
Treasure Harbor

Breezy Palms Resort

Breezy Palms Resort
2.5 star property
Matecumbe
8.8 out of 10, Excellent, (584)
"we stayed in the beach front cottage kitchen was stocked room was clean and the views were great friendly staff "
United States
Terry
The price is AU$225
includes taxes & fees
17 Dec - 18 Dec
Breezy Palms Resort

Amazing Ocean view condo

Amazing Ocean view condo
Tavernier
9.6 out of 10, Exceptional, (42)
"Exceeded expectations, exceptionally clean, great for kids (they loved the pool), perfect for our Keys trip"
United States
Natalie M.
The price is AU$524
includes taxes & fees
14 Dec - 15 Dec
Amazing Ocean view condo

Florida Keys Getaway - Slps 4 - Ocean View

Florida Keys Getaway - Slps 4 - Ocean View
Tavernier
9.6 out of 10, Exceptional, (18)
"Room and location were great! Community pool was very nice and we used it a lot. Quick walk down to the marina. We would stay here again."
United States
Kyle W.
The price is AU$520
includes taxes & fees
13 Dec - 14 Dec
Florida Keys Getaway - Slps 4 - Ocean View

Aqua Vista Ocean Pointe 3307

Aqua Vista Ocean Pointe 3307
2.5 star property
Tavernier
10.0 out of 10, Exceptional, (1)
"Beautiful & perfect place for a getaway. Really enjoyed our stay. Highly recommend."
United States
Michelle
The price is AU$619
includes taxes & fees
14 Dec - 15 Dec
Aqua Vista Ocean Pointe 3307

Charming Home in Key Largo

Charming Home in Key Largo
Key Largo
9.8 out of 10, Exceptional, (27)
"It was clean and a very nice place to stay. Plenty of room and awesome amenities."
United States
Eric M.
The price is AU$725
includes taxes & fees
28 Dec - 29 Dec
Charming Home in Key Largo

Serenity In The Sun Condo Fabulous Ocean View

Serenity In The Sun Condo Fabulous Ocean View
Tavernier
10.0 out of 10, Exceptional, (107)
"Good clean condo, great pool and little private beach "
United Kingdom
Nicola W.
The price is AU$772
includes taxes & fees
5 Jan - 6 Jan 2026
Serenity In The Sun Condo Fabulous Ocean View

Island Bay Resort

Island Bay Resort
2.5 star property
Tavernier
10.0 out of 10, Exceptional, (140)
"Buutifull and cozy place "
United States
DILIA
The price is AU$430
includes taxes & fees
14 Dec - 15 Dec
Island Bay Resort

Reel Key Largo Escape Ocean Pointe 5209

Reel Key Largo Escape Ocean Pointe 5209
Tavernier
9.4 out of 10, Exceptional, (6)
"Great area"
United States
Yesenia
The price is AU$619
includes taxes & fees
14 Dec - 15 Dec
Reel Key Largo Escape Ocean Pointe 5209

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

Ocean View Gem Ocean Pointe 3406 2BA/2BR King/Queen
2.0 star property
Tavernier
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."
United States
Kevin W.
The price is AU$653
includes taxes & fees
14 Dec - 15 Dec
Ocean View Gem Ocean Pointe 3406 2BA/2BR King/Queen

Island Sanctuary Islamorada

Island Sanctuary Islamorada
Tavernier
9.8 out of 10, Exceptional, (12)
"It exceeded our expectations, and we are so glad we found this location!"
United States
Jenn H.
The price is AU$640
includes taxes & fees
14 Dec - 15 Dec
Island Sanctuary Islamorada

Private 2-bedroom apartment with kitchen in lovely Tavernier, Key Largo

Private 2-bedroom apartment with kitchen in lovely Tavernier, Key Largo
2.0 star property
Tavernier
The price is AU$484
includes taxes & fees
15 Dec - 16 Dec
Private 2-bedroom apartment with kitchen in lovely Tavernier, Key Largo

Modern and Coastal Ocean Pointe 2307

Modern and Coastal Ocean Pointe 2307
Tavernier
10.0 out of 10, Exceptional, (122)
"We loved the condo. The immenities were very nice. Very clear about what was provided. The cafe and pool were fantastic! The pool was crystal clear! Thank you for a lovely stay!!"
United States
Emily T.
The price is AU$641
includes taxes & fees
14 Dec - 15 Dec
Modern and Coastal Ocean Pointe 2307

Flamingo Flats Ocean Pointe 5306 2BR/2BA

Flamingo Flats Ocean Pointe 5306 2BR/2BA
Tavernier
9.6 out of 10, Exceptional, (7)
"Great location and prompt support with all questions we had. "
United States
Jim I.
The price is AU$635
includes taxes & fees
17 Dec - 18 Dec
Flamingo Flats Ocean Pointe 5306 2BR/2BA

1BR w/ Partial Ocean View, Pool & Beach

1BR w/ Partial Ocean View, Pool & Beach
2.0 star property
Tavernier
10.0 out of 10, Exceptional, (3)
"Loved the property and its central location. Fairly quiet and secluded. Incredible views and the complex has everything you need for a nice relaxing vacation. With the prices they offer, I can’t recommend it enough!"
United States
Andrew W.
The price is AU$533
includes taxes & fees
14 Dec - 15 Dec
1BR w/ Partial Ocean View, Pool & Beach

Blue Haven Key Largo | Ocean Pointe 1315

Blue Haven Key Largo | Ocean Pointe 1315
Tavernier
9.6 out of 10, Exceptional, (15)
"This condo was everything we needed. Lots of space, bug comfy beds, hreat shower and the pool at the complex was great in the late afternoon after a day exploring the upper keys. There were works going on at the conplex when we were there which took the edge off things as 9am drilling on Monday morning wasnt welcome but I only knocked 1 star off - otherwise wouldnt hesitate to recommend!"
United Kingdom
Philippa
The price is AU$637
includes taxes & fees
15 Dec - 16 Dec
Blue Haven Key Largo | Ocean Pointe 1315

Fla Keys Luxury Houseboat, Prime Location-Steps to Fun, Food & Water Adventures

Fla Keys Luxury Houseboat, Prime Location-Steps to Fun, Food & Water Adventures
Tavernier
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 AU$666
includes taxes & fees
14 Dec - 15 Dec
Fla Keys Luxury Houseboat, Prime Location-Steps to Fun, Food & Water Adventures

Sea View Farm Style Ocean front Condo Views

Sea View Farm Style Ocean front Condo Views
Tavernier
10.0 out of 10, Exceptional, (154)
"The property was excellent."
United States
June M.
The price is AU$673
includes taxes & fees
17 Dec - 18 Dec
Sea View Farm Style Ocean front Condo Views

Boho Chic Ocean Pointe 3214

Boho Chic Ocean Pointe 3214
Tavernier
10.0 out of 10, Exceptional, (12)
"It was clean, well organized and communication was great. Had a good time."
United States
Shirl
The price is AU$658
includes taxes & fees
17 Dec - 18 Dec
Boho Chic Ocean Pointe 3214

Lazy Daze Double King Suite Ocean Pointe 2310

Lazy Daze Double King Suite Ocean Pointe 2310
Tavernier
9.8 out of 10, Exceptional, (26)
"Everything was exceptionally nice. Would definitely book again."
United States
Sharon
The price is AU$653
includes taxes & fees
14 Dec - 15 Dec
Lazy Daze Double King Suite Ocean Pointe 2310
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$225 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?

Bungalow #4 - 2 Bed/1 Bath & Pool in Islamorada: This highly rated holiday home rental in Islamorada offers an outdoor pool, a BBQ and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave. Some other homes for rent in Islamorada include Next availability from May 18th, 2024 - The Last Resort, Islamorada - MM76.7 and Bungalow #3 - 2 Bed/1 Bath & Pool in Islamorada.

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 Everglades National Park and Founders Park, 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.