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, (152 reviews)
"Amazing stay!"
United States
Amanda
The price is AU$395
includes taxes & fees
5 May - 6 May
Treasure Harbor

The Islands of Islamorada

The Islands of Islamorada
4.0 star property
Matecumbe
9.8 out of 10, Exceptional, (74 reviews)
"What a wonderful venue for our last 2 nights in the Keys. This place is a hidden gem. The entire staff, especially Edith, the bartender, were fantastic."
United States
Michael
The price is AU$1,014
includes taxes & fees
11 May - 12 May
The Islands of Islamorada

Breezy Palms Resort

Breezy Palms Resort
2.5 star property
Matecumbe
8.8 out of 10, Excellent, (666 reviews)
"Clean room, good staff and convenience location for a visit."
United States
Judbelth
The price is AU$195
includes taxes & fees
13 May - 14 May
Breezy Palms Resort

Two Panoramic Ocean Views from the Living room and Master Bedroom in this Condo

Two Panoramic Ocean Views from the Living room and Master Bedroom in this Condo
Tavernier
9.8 out of 10, Exceptional, (239 reviews)
"Great place to stay"
United States
Llonda B.
The price is AU$582
includes taxes & fees
5 May - 6 May
Two Panoramic Ocean Views from the Living room and Master Bedroom in this Condo

Modern and Coastal Ocean Pointe 2307

Modern and Coastal Ocean Pointe 2307
Tavernier
10.0 out of 10, Exceptional, (130 reviews)
"Very nice property. Hosts were great. "
United States
Tad L.
The price is AU$654
includes taxes & fees
20 May - 21 May
Modern and Coastal Ocean Pointe 2307

Island Sanctuary Islamorada

Island Sanctuary Islamorada
Tavernier
9.8 out of 10, Exceptional, (22 reviews)
"Kelly is the best host!!! Excellent views and comfort. It was magical for me and my wife. Thank you!"
United States
Aisel R.
The price is AU$592
includes taxes & fees
5 May - 6 May
Island Sanctuary Islamorada

Ocean view condo with balcony/marina view

Ocean view condo with balcony/marina view
Tavernier
8.8 out of 10, Excellent, (43 reviews)
"Rooms were spacious and a short drive to most of the attractions we wanted to do. Rooms and bathrooms were gorgeous!"
United States
Cindy
The price is AU$598
includes taxes & fees
3 May - 4 May
Ocean view condo with balcony/marina view

Dazzling Ocean Pointe -OP-Main

Dazzling Ocean Pointe -OP-Main
Tavernier
9.0 out of 10, Wonderful, (94 reviews)
"Cleanliness, location, communication and the pool was just great! Thank you so very much!"
United States
Vicky W.
The price is AU$462
includes taxes & fees
4 May - 5 May
Dazzling Ocean Pointe -OP-Main

Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ

Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
Tavernier
10.0 out of 10, Exceptional, (114 reviews)
"Fantastic place to stay! Very clean and great hosts. Will stay again. "
United States
Les
The price is AU$632
includes taxes & fees
17 May - 18 May
Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ

Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ

Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
Tavernier
10.0 out of 10, Exceptional, (165 reviews)
"Everything was as described and we truly enjoyed our stay. We traveled with small children and the home was fit for them. It’s a true vacation place. I highly recommend staying! "
United States
keli p.
The price is AU$626
includes taxes & fees
7 May - 8 May
Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ

Beautiful Kawama Townhouse

Beautiful Kawama Townhouse
Key Largo
9.8 out of 10, Exceptional, (147 reviews)
"The host, house and amenities were perfect. all praises.."
United States
Pete S.
The price is AU$898
includes taxes & fees
3 May - 4 May
Beautiful Kawama Townhouse

Your Happy Place - gorgeous 2 bed/2 bath oceanfront suite with full kitchen

Your Happy Place - gorgeous 2 bed/2 bath oceanfront suite with full kitchen
Tavernier
10.0 out of 10, Exceptional, (16 reviews)
"Perfect Stay."
United States
suhaela s.
The price is AU$569
includes taxes & fees
4 May - 5 May
Your Happy Place - gorgeous 2 bed/2 bath oceanfront suite with full kitchen

Flamingo Flats Ocean Pointe 5306 2BR/2BA

Flamingo Flats Ocean Pointe 5306 2BR/2BA
Tavernier
9.6 out of 10, Exceptional, (8 reviews)
"Great location and prompt support with all questions we had. "
United States
Jim I.
The price is AU$619
includes taxes & fees
17 May - 18 May
Flamingo Flats Ocean Pointe 5306 2BR/2BA

Casa Largo

Casa Largo
Key Largo
9.2 out of 10, Wonderful, (133 reviews)
"The unit was clean and beautiful. The entire complex was very nice, too. We had everything needed to enjoy our stay."
United States
Rhonda D.
The price is AU$757
includes taxes & fees
3 May - 4 May
Casa Largo

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, (7 reviews)
"Great location and clean"
United States
Matthew H.
The price is AU$608
includes taxes & fees
27 May - 28 May
Sunrise Oasis - Top Floor 2 BR 2 BA Condo 2411

Sea View and Sunrise Ocean Pointe 2412 2BA/2BR

Sea View and Sunrise Ocean Pointe 2412 2BA/2BR
Tavernier
9.6 out of 10, Exceptional, (89 reviews)
"Good location"
United States
Dimitri O.
The price is AU$617
includes taxes & fees
12 May - 13 May
Sea View and Sunrise Ocean Pointe 2412 2BA/2BR

Nauti Hideaway Ocean Pointe 2314

Nauti Hideaway Ocean Pointe 2314
Tavernier
10.0 out of 10, Exceptional, (2 reviews)
"Great communication. Very clean. We loved view from the room. We would definitely stay here again!"
United States
Cynthia L.
The price is AU$659
includes taxes & fees
25 May - 26 May
Nauti Hideaway Ocean Pointe 2314

Blue Haven Key Largo | Ocean Pointe 1315

Blue Haven Key Largo | Ocean Pointe 1315
Tavernier
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 AU$593
includes taxes & fees
20 May - 21 May
Blue Haven Key Largo | Ocean Pointe 1315

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, (28 reviews)
"Beautiful condo with nice decor. We enjoyed the pool and was nice having a restaurant on site. I would definitely stay there again "
United States
Cathy
The price is AU$601
includes taxes & fees
14 May - 15 May
Starfish Seas Ocean Pointe 1302 King/Queen 2BA 2BR

NEW ! Lagoon-front townhouse with Marina! Day Dreams Key Largo.

NEW ! Lagoon-front townhouse with Marina! Day Dreams Key Largo.
Key Largo
10.0 out of 10, Exceptional, (53 reviews)
"Had a great stay. Being so close to the lagoon we were able to launch the kayaks for our kids multiple times a day no problem. We saw tarpon, lobster, parrot fish and tons of other sea life right out the front door. And the pool was just as close. Also being on this side of the property it is a quick walk to the beach to watch the sunset. The unit seemed as if we were the first ones staying there after it had been renovated. Grew up in south Florida and had stopped coming back to visit but we...
United States
Jonathan D.
The price is AU$922
includes taxes & fees
11 May - 12 May
NEW ! Lagoon-front townhouse with Marina! Day Dreams 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$195 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 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?

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 Islamorada Anglers Reef! “Sandbar Bungalow Villa" AMAZING! Middle row location! .

How many holiday rentals are there in Islamorada?

With 410 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 Anne's Beach 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 Robbie’s of Islamorada.

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.