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, (153 reviews)
"Amazing stay!"
United States
Amanda
The price is NZ$593
includes taxes & fees
6 June - 7 June
Treasure Harbor

Breezy Palms Resort

Breezy Palms Resort
2.5 star property
Matecumbe
8.8 out of 10, Excellent, (675 reviews)
"Easy parking and great clean kitchen"
United States
JoAnn
The price is NZ$329
includes taxes & fees
27 May - 28 May
Breezy Palms Resort

Island Bay Resort

Island Bay Resort
2.5 star property
Tavernier
10.0 out of 10, Exceptional, (168 reviews)
"Very nice small resort."
United States
Dan
The price is NZ$543
includes taxes & fees
8 June - 9 June
Island Bay Resort

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 NZ$739
includes taxes & fees
10 June - 11 June
Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ

The Islands of Islamorada

The Islands of Islamorada
4.0 star property
Matecumbe
9.6 out of 10, Exceptional, (75 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 NZ$1,193
includes taxes & fees
20 May - 21 May
The Islands of Islamorada

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

Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
Tavernier
10.0 out of 10, Exceptional, (166 reviews)
"Very nice place. Clean and easy to contact the host."
United States
Bonnie H.
The price is NZ$730
includes taxes & fees
18 May - 19 May
Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ

Charming Home in Key Largo

Charming Home in Key Largo
Key Largo
9.8 out of 10, Exceptional, (37 reviews)
"Comfortable and well thought out space."
United States
Jessica E.
The price is NZ$678
includes taxes & fees
26 May - 27 May
Charming Home in Key Largo

Dazzling Ocean View Suite w/heated pool, beach, marina, tennis/pickleball

Dazzling Ocean View Suite w/heated pool, beach, marina, tennis/pickleball
Tavernier
9.0 out of 10, Wonderful, (95 reviews)
"Right in the heart of Key Largo but just off the beaten path. Clean, comfortable and cozy. The property has a beach, pool and restaurant which was convenient after a long day of travel."
United States
jodi
The price is NZ$540
includes taxes & fees
17 May - 18 May
Dazzling Ocean View Suite w/heated pool, beach, marina, tennis/pickleball

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, (8 reviews)
"Great location and clean"
United States
Matthew H.
The price is NZ$794
includes taxes & fees
3 June - 4 June
Sunrise Oasis - Top Floor 2 BR 2 BA Condo 2411

3212 Across from Pool * King & Queen/Twin Bunk Bed

3212 Across from Pool * King & Queen/Twin Bunk Bed
Tavernier
9.8 out of 10, Exceptional, (157 reviews)
"Really enjoyed the location and the unit. "
United States
Teresa L.
The price is NZ$888
includes taxes & fees
16 May - 17 May
3212 Across from Pool * King & Queen/Twin Bunk Bed

Ocean view condo with balcony/marina view

Ocean view condo with balcony/marina view
Tavernier
8.8 out of 10, Excellent, (44 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 NZ$723
includes taxes & fees
18 May - 19 May
Ocean view condo with balcony/marina view

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, (241 reviews)
"Great place to stay"
United States
Llonda B.
The price is NZ$886
includes taxes & fees
30 May - 31 May
Two Panoramic Ocean Views from the Living room and Master Bedroom in this Condo

Florida Keys Getaway - Slps 4 - Ocean View

Florida Keys Getaway - Slps 4 - Ocean View
Tavernier
9.8 out of 10, Exceptional, (30 reviews)
"A comfortable little condo, conveniently located for exploring the Keys. There’s a nice pool and small beach area with a bar/restaurant that are well maintained."
United States
Stephen
The price is NZ$630
includes taxes & fees
30 May - 31 May
Florida Keys Getaway - Slps 4 - Ocean View

Serene Oceanfront Keys Condo

Serene Oceanfront Keys Condo
Tavernier
10.0 out of 10, Exceptional, (37 reviews)
"We enjoyed our stay. It was very convenient to where we needed to be. The apartment was well stocked and had a nice view. The beds were very comfortable as well and the host was very responsive! Would recommend staying here if you’re in the area. "
United States
Mark F.
The price is NZ$759
includes taxes & fees
17 May - 18 May
Serene Oceanfront Keys Condo

Island Sanctuary Islamorada

Island Sanctuary Islamorada
Tavernier
9.6 out of 10, Exceptional, (24 reviews)
"What a neat experience, wonderful boat, waking up on the water was beautiful! Kelly was cery responsive to anything we needed!"
United States
Leanne W.
The price is NZ$708
includes taxes & fees
18 May - 19 May
Island Sanctuary Islamorada

Key Largo 2BR w/ Partial Ocean Views & Pool

Key Largo 2BR w/ Partial Ocean Views & Pool
Tavernier
The price is NZ$663
includes taxes & fees
18 May - 19 May
Key Largo 2BR w/ Partial Ocean Views & Pool

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, (17 reviews)
"Perfect Stay."
United States
suhaela s.
The price is NZ$765
includes taxes & fees
25 May - 26 May
Your Happy Place - gorgeous 2 bed/2 bath oceanfront suite with full kitchen

4 Flr |2 Mastr |Oceanview |Jacuzzi |Beach |Marina

4 Flr |2 Mastr |Oceanview |Jacuzzi |Beach |Marina
Tavernier
9.8 out of 10, Exceptional, (47 reviews)
"There was no staff but the apartment was spotless and very well appointed with amenities like coffee, etc. Everything was clean, neat and new feeling. The beds were very comfortable and the apartment was spacious and welcoming with great views."
United States
Sandra
The price is NZ$742
includes taxes & fees
26 May - 27 May
4 Flr |2 Mastr |Oceanview |Jacuzzi |Beach |Marina

Lazy Daze Double King Suite Ocean Pointe 2310

Lazy Daze Double King Suite Ocean Pointe 2310
Tavernier
9.8 out of 10, Exceptional, (31 reviews)
"Everything was exceptionally nice. Would definitely book again."
United States
Sharon
The price is NZ$720
includes taxes & fees
17 May - 18 May
Lazy Daze Double King Suite Ocean Pointe 2310

Aqua Vista Ocean Pointe 3307

Aqua Vista Ocean Pointe 3307
Tavernier
10.0 out of 10, Exceptional, (3 reviews)
"Beautiful & perfect place for a getaway. Really enjoyed our stay. Highly recommend."
United States
Michelle
The price is NZ$896
includes taxes & fees
12 June - 13 June
Aqua Vista Ocean Pointe 3307
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$329 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?

Next availability from May 18th, 2024 - The Last Resort, Islamorada - MM76.7: 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. It offers a rooftop terrace, a private garden and a selection of games so that you can immerse yourself in your holiday. Some other homes for rent in Islamorada include Bungalow #4 - 2 Bed/1 Bath & Pool in Islamorada and Anglers Reef Islamorada home with ocean views, private marina, beach & pool.

How many holiday rentals are there in Islamorada?

With 403 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 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.