Holiday Rentals in Islamorada

  • 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

Aparthotel in Matecumbe

Breezy Palms Resort
2.5 star property
8.8 out of 10, Excellent, (624 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 €208
includes taxes & fees
25 Mar - 26 Mar
Breezy Palms Resort

Houseboat in Islamorada

Treasure Harbor
3.0 star property
9.0 out of 10, Wonderful, (135 reviews)
"Very peaceful and comfortable stay! Dallas and Hannah were amazing hosts! Thank you so much !"
United States
Nick
The price is €298
includes taxes & fees
1 Mar - 2 Mar
Treasure Harbor

Villa in Matecumbe

The Islands of Islamorada
4.0 star property
9.8 out of 10, Exceptional, (71 reviews)
"Beautiful accommodations and location, very clean, many activities available at resort"
United States
Janet
The price is €904
includes taxes & fees
3 Mar - 4 Mar
The Islands of Islamorada

Holiday Home in Key Largo

Charming Home in Key Largo
9.8 out of 10, Exceptional, (31 reviews)
"Great location. Very clean very nice, stay there again"
United States
Mark B.
The price is €382
includes taxes & fees
29 Mar - 30 Mar
Charming Home in Key Largo
10.0 out of 10, Exceptional, (111 reviews)
"Fantastic place to stay! Very clean and great hosts. Will stay again. "
United States
Les
The price is €473
includes taxes & fees
10 Mar - 11 Mar
Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
9.0 out of 10, Wonderful, (18 reviews)
"Apartment was bot cleaned properly prior to arrival. Otherwise very good location and cozy"
United States
Devin
The price is €489
includes taxes & fees
4 Mar - 5 Mar
Ocean View 2BR Pool, Private Beach
10.0 out of 10, Exceptional, (162 reviews)
"Very clean and quiet location. Beds were comfy and all necessities were provided. Would definately recommend!"
United States
Arielle F.
The price is €444
includes taxes & fees
23 Mar - 24 Mar
Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
9.8 out of 10, Exceptional, (152 reviews)
"Great stay lovely home "
United States
Yezenia
The price is €416
includes taxes & fees
4 Mar - 5 Mar
3212 Across from Pool * King & Queen/Twin Bunk Bed
9.8 out of 10, Exceptional, (46 reviews)
"Would stay there again."
Canada
jamie g.
The price is €477
includes taxes & fees
29 Mar - 30 Mar
4 Flr |2 Mastr |Oceanview |Jacuzzi |Beach |Marina
9.6 out of 10, Exceptional, (21 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.
Florida Keys Getaway - Slps 4 - Ocean View
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 €403
includes taxes & fees
3 Mar - 4 Mar
Starfish Seas Ocean Pointe 1302 King/Queen 2BA 2BR
10.0 out of 10, Exceptional, (12 reviews)
"Perfect Stay."
United States
suhaela s.
The price is €566
includes taxes & fees
26 Mar - 27 Mar
Your Happy Place - gorgeous 2 bed/2 bath oceanfront suite with full kitchen
8.8 out of 10, Excellent, (42 reviews)
"The condo was renovated, and very nicely decorated, very clean and cozy. We enjoyed our short stay. Community and pool were good too. "
United States
Lina
The price is €454
includes taxes & fees
9 Mar - 10 Mar
Ocean view condo with balcony/marina view
9.6 out of 10, Exceptional, (7 reviews)
"Great area"
United States
Yesenia
The price is €463
includes taxes & fees
23 Mar - 24 Mar
Reel Key Largo Escape Ocean Pointe 5209
Key Largo 2 BR Condo - Ocean Views, Pool, Beach
9.8 out of 10, Exceptional, (16 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 €435
includes taxes & fees
4 Mar - 5 Mar
Blue Haven Key Largo | Ocean Pointe 1315
10.0 out of 10, Exceptional, (8 reviews)
"Very clean and well maintained"
United States
Maria M.
Oceanfront 2BR/2BA Remodeled Condo King + Bunk Room Balcony Views
9.8 out of 10, Exceptional, (58 reviews)
"Great stay! "
United States
Theresa N.
The price is €428
includes taxes & fees
1 Mar - 2 Mar
Re-energize at our spacious condo! Get 10% off stays of 7+ days. Book now!

Holiday Home in Key Largo

Beautiful Kawama Townhouse
9.8 out of 10, Exceptional, (142 reviews)
"The host, house and amenities were perfect. all praises.."
United States
Pete S.
The price is €765
includes taxes & fees
2 Mar - 3 Mar
Beautiful Kawama Townhouse
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, apart-hotels, 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 €208 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 in Islamorada close to MoradaWay Arts & Cultural District, 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?

Private Oceanfront: Heated Pool, Paddleboards & Kayaks - 180 degree ocean views: This highly rated holiday home rental in Islamorada is located on the beach, and has an outdoor pool, a balcony and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Some other homes for rent in Islamorada include Bungalow #4 - 2 Bed/1 Bath & Pool in Islamorada and TikiBar with TV &Stereo, PrivateSpa, Heated Pool, Hammock,SUP’s, Kayaks,Bikes,FP.

How many holiday rentals are there in Islamorada?

With 424 Expedia holiday rentals, you're guaranteed to find just the right place for your Islamorada stay.

What can I see and do in Islamorada?

Everglades National Park and Islamorada County 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 Anne's Beach.

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.