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, (129 reviews)
"Very peaceful and comfortable stay! Dallas and Hannah were amazing hosts! Thank you so much !"
United States
Nick
Treasure Harbor

Charming Home in Key Largo

Charming Home in Key Largo
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 NZ$826
includes taxes & fees
23 Feb - 24 Feb
Charming Home in Key Largo

Breezy Palms Resort

Breezy Palms Resort
2.5 star property
Matecumbe
8.8 out of 10, Excellent, (618 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 NZ$468
includes taxes & fees
25 Feb - 26 Feb
Breezy Palms Resort

Island Sanctuary Islamorada

Island Sanctuary Islamorada
Tavernier
9.8 out of 10, Exceptional, (15 reviews)
"An amazing place to switch gears. Great host. Win/win."
United States
Alex Z.
The price is NZ$689
includes taxes & fees
15 Feb - 16 Feb
Island Sanctuary Islamorada

Serenity In The Sun Condo Fabulous Ocean View

Serenity In The Sun Condo Fabulous Ocean View
Tavernier
10.0 out of 10, Exceptional, (108 reviews)
"Fantastic place to stay! Very clean and great hosts. Will stay again. "
United States
Les
The price is NZ$907
includes taxes & fees
10 Mar - 11 Mar
Serenity In The Sun Condo Fabulous Ocean View

Amazing Ocean view condo

Amazing Ocean view condo
Tavernier
9.6 out of 10, Exceptional, (44 reviews)
"Exceeded expectations, exceptionally clean, great for kids (they loved the pool), perfect for our Keys trip"
United States
Natalie M.
The price is NZ$744
includes taxes & fees
1 Mar - 2 Mar
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, (20 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.
The price is NZ$754
includes taxes & fees
25 Feb - 26 Feb
Florida Keys Getaway - Slps 4 - Ocean View

Paradise Palms 2 Bedroom Condo Ocean Pointe 1206

Paradise Palms 2 Bedroom Condo Ocean Pointe 1206
Tavernier
9.8 out of 10, Exceptional, (6 reviews)
"Thanks for your great hospitality."
United States
richard
The price is NZ$770
includes taxes & fees
4 Mar - 5 Mar
Paradise Palms 2 Bedroom Condo Ocean Pointe 1206

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, (152 reviews)
"Great stay lovely home "
United States
Yezenia
The price is NZ$841
includes taxes & fees
4 Mar - 5 Mar
3212 Across from Pool * King & Queen/Twin Bunk Bed

Reel Key Largo Escape Ocean Pointe 5209

Reel Key Largo Escape Ocean Pointe 5209
Tavernier
9.4 out of 10, Exceptional, (6 reviews)
"Great area"
United States
Yesenia
The price is NZ$916
includes taxes & fees
25 Feb - 26 Feb
Reel Key Largo Escape Ocean Pointe 5209

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 NZ$801
includes taxes & fees
4 Mar - 5 Mar
Blue Haven Key Largo | Ocean Pointe 1315

Lazy Daze Double King Suite Ocean Pointe 2310

Lazy Daze Double King Suite Ocean Pointe 2310
Tavernier
9.8 out of 10, Exceptional, (26 reviews)
"Everything was exceptionally nice. Would definitely book again."
United States
Sharon
The price is NZ$932
includes taxes & fees
11 Mar - 12 Mar
Lazy Daze Double King Suite Ocean Pointe 2310

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, (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 NZ$849
includes taxes & fees
3 Mar - 4 Mar
Starfish Seas Ocean Pointe 1302 King/Queen 2BA 2BR

Boho Style Florida Keys Condo Ocean Views

Boho Style Florida Keys Condo Ocean Views
Tavernier
9.8 out of 10, Exceptional, (44 reviews)
"Would stay there again."
Canada
jamie g.
The price is NZ$911
includes taxes & fees
9 Mar - 10 Mar
Boho Style Florida Keys Condo Ocean Views

Serene Oceanfront Keys Condo

Serene Oceanfront Keys Condo
Tavernier
10.0 out of 10, Exceptional, (24 reviews)
"Great stay, amazing pool and property, "
United States
Abbigail R.
The price is NZ$972
includes taxes & fees
5 Mar - 6 Mar
Serene Oceanfront Keys Condo

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, (12 reviews)
"Perfect Stay."
United States
suhaela s.
The price is NZ$1,049
includes taxes & fees
10 Mar - 11 Mar
Your Happy Place - gorgeous 2 bed/2 bath oceanfront suite with full kitchen

Reel Large END Unit in Ocean Pointe Suites - Newly Renovated!

Reel Large END Unit in Ocean Pointe Suites - Newly Renovated!
Tavernier
9.4 out of 10, Exceptional, (17 reviews)
"We love our family vacations there."
United States
Francis M.
The price is NZ$1,186
includes taxes & fees
24 Feb - 25 Feb
Reel Large END Unit in Ocean Pointe Suites - Newly Renovated!

Sunrise Sanctuary - Top Floor Ocean Pointe 2415

Sunrise Sanctuary - Top Floor Ocean Pointe 2415
Tavernier
9.6 out of 10, Exceptional, (12 reviews)
"Clean and great location "
United States
Michael P.
The price is NZ$826
includes taxes & fees
9 Mar - 10 Mar
Sunrise Sanctuary - Top Floor Ocean Pointe 2415

Keys Bohemian 2 BR 2 BA at Ocean Pointe 1312

Keys Bohemian 2 BR 2 BA at Ocean Pointe 1312
Tavernier
10.0 out of 10, Exceptional, (1 review)
The price is NZ$842
includes taxes & fees
4 Mar - 5 Mar
Keys Bohemian 2 BR 2 BA at Ocean Pointe 1312

Ocean View Overlooking Marina Ocean Pointe 5305

Ocean View Overlooking Marina Ocean Pointe 5305
Tavernier
10.0 out of 10, Exceptional, (24 reviews)
"This was a wonderful place to stay in the Florida Keys. The location was beautiful. We watched sunrise each morning from the balcony. The unit faced the ocean. We would certainly stay here again."
United States
Donald
The price is NZ$957
includes taxes & fees
7 Mar - 8 Mar
Ocean View Overlooking Marina Ocean Pointe 5305
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$468 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 #3 - 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 Private Oceanfront: Heated Pool, Paddleboards & Kayaks - 180 degree ocean views and Single Family Home In Angler's Reef Gated Community, Beaches,Marina,Heated Pool.

How many holiday rentals are there in Islamorada?

With 463 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 Islamorada County Park, or simply take in cultural attractions like History of Diving Museum and MoradaWay Arts & Cultural District. 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.