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, (119)
"Great spot! Will be back someday hopefully. "
Canada
Diane
Treasure Harbor

Breezy Palms Resort

Breezy Palms Resort
2.5 star property
Matecumbe
8.8 out of 10, Excellent, (600)
"Property was nice and easy to navigate, ocean view room was extra nice to have!"
United States
Lisa
The price is NZ$385
includes taxes & fees
8 Jan - 9 Jan 2026
Breezy Palms Resort

The Islands of Islamorada

The Islands of Islamorada
4.0 star property
Matecumbe
9.8 out of 10, Exceptional, (70)
"Great for family vacation with kids. love it"
United States
Dixania
The price is NZ$1,268
includes taxes & fees
14 Jan - 15 Jan 2026
The Islands of Islamorada

Island Bay Resort

Island Bay Resort
2.5 star property
Tavernier
10.0 out of 10, Exceptional, (141)
"Very quiet and the outdoor spaces are very nice. Staff was very friendly also."
United States
Jacob
The price is NZ$792
includes taxes & fees
1 Jan - 2 Jan 2026
Island Bay Resort

Island Sanctuary Islamorada

Island Sanctuary Islamorada
Tavernier
9.8 out of 10, Exceptional, (13)
"It exceeded our expectations, and we are so glad we found this location!"
United States
Jenn H.
The price is NZ$693
includes taxes & fees
7 Jan - 8 Jan 2026
Island Sanctuary Islamorada

Boho Style Florida Keys Condo Ocean Views

Boho Style Florida Keys Condo Ocean Views
Tavernier
9.8 out of 10, Exceptional, (43)
"Would stay there again."
Canada
jamie g.
The price is NZ$840
includes taxes & fees
28 Jan - 29 Jan 2026
Boho Style Florida Keys Condo Ocean Views

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.
Amazing Ocean view condo

Serenity In The Sun Condo Fabulous Ocean View

Serenity In The Sun Condo Fabulous Ocean View
Tavernier
10.0 out of 10, Exceptional, (108)
"Fantastic place to stay! Very clean and great hosts. Will stay again. "
United States
Les
The price is NZ$795
includes taxes & fees
5 Jan - 6 Jan 2026
Serenity In The Sun Condo Fabulous 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 NZ$835
includes taxes & fees
4 Jan - 5 Jan 2026
Aqua Vista Ocean Pointe 3307

Charming Home in Key Largo

Charming Home in Key Largo
Key Largo
9.8 out of 10, Exceptional, (29)
"It was clean and a very nice place to stay. Plenty of room and awesome amenities."
United States
Eric M.
The price is NZ$781
includes taxes & fees
4 Jan - 5 Jan 2026
Charming Home in Key Largo

Modern and Coastal 3212 is Across from Pool

Modern and Coastal 3212 is Across from Pool
Tavernier
9.8 out of 10, Exceptional, (150)
"Great stay lovely home "
United States
Yezenia
The price is NZ$796
includes taxes & fees
12 Jan - 13 Jan 2026
Modern and Coastal 3212 is Across from Pool

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 NZ$863
includes taxes & fees
11 Jan - 12 Jan 2026
Fla Keys Luxury Houseboat, Prime Location-Steps to Fun, Food & Water Adventures

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 NZ$888
includes taxes & fees
21 Jan - 22 Jan 2026
Ocean View Gem Ocean Pointe 3406 2BA/2BR King/Queen

Island Time at Ocean Pointe Luxe 2 King Spa BR/BA, 2 Balcony

Island Time at Ocean Pointe Luxe 2 King Spa BR/BA, 2 Balcony
2.0 star property
Blue Waters
10.0 out of 10, Exceptional, (2)
"Beautifully high-end decorated & furnished like brand new! Very clean and appointed with everything one could want for a perfect stay. First floor convenience (building elevated on piers) but no water view Would definitely return! "
United States
Peter A. Z.
The price is NZ$792
includes taxes & fees
13 Jan - 14 Jan 2026
Island Time at Ocean Pointe Luxe 2 King Spa BR/BA, 2 Balcony

NEW ! Lagoon-front townhouse with Marina in Key Largo

NEW ! Lagoon-front townhouse with Marina in Key Largo
2.0 star property
Key Largo
10.0 out of 10, Exceptional, (46)
"Good location. Lagoon and pool right outside door. "
United States
Debra C.
The price is NZ$1,017
includes taxes & fees
12 Jan - 13 Jan 2026
NEW ! Lagoon-front townhouse with Marina 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, (155)
"The property was excellent."
United States
June M.
The price is NZ$768
includes taxes & fees
5 Jan - 6 Jan 2026
Sea View Farm Style Ocean front Condo Views

Ocean Pointe Condo ~ Beach, Pool, Hot Tub & Tennis

Ocean Pointe Condo ~ Beach, Pool, Hot Tub & Tennis
2.0 star property
Key Largo
The price is NZ$771
includes taxes & fees
7 Jan - 8 Jan 2026
Ocean Pointe Condo ~ Beach, Pool, Hot Tub & Tennis

1BR w/ Pool, Beach, Near Marine & Bird Sanctuaries

1BR w/ Pool, Beach, Near Marine & Bird Sanctuaries
2.0 star property
Tavernier
The price is NZ$697
includes taxes & fees
6 Jan - 7 Jan 2026
1BR w/ Pool, Beach, Near Marine & Bird Sanctuaries

Sunrise Sanctuary - Top Floor Ocean Pointe 2415

Sunrise Sanctuary - Top Floor Ocean Pointe 2415
Tavernier
9.6 out of 10, Exceptional, (11)
"Clean and great location "
United States
Michael P.
The price is NZ$776
includes taxes & fees
13 Jan - 14 Jan 2026
Sunrise Sanctuary - Top Floor Ocean Pointe 2415

Captains Quarters Ocean Pointe 4405

Captains Quarters Ocean Pointe 4405
Tavernier
10.0 out of 10, Exceptional, (13)
"We had a very pleasant weekend away with all the comforts of home, yet even better with the amazing view! Great communication with the host with quick pleasant responses. The property is conveniently located and easy to get around. "
United States
Debbie W.
The price is NZ$792
includes taxes & fees
12 Jan - 13 Jan 2026
Captains Quarters Ocean Pointe 4405
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 favorite 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 depends 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 NZ$385 per night. Entering your travel dates in the search wizard you might find 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 483 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.