Islamorada Holiday Rentals

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Our top choices for Islamorada holiday rentals

Breezy Palms Resort

Breezy Palms Resort
2.5 star property
Matecumbe
8.8 out of 10, Excellent, (696 reviews)
"Cute lil resort with pool, beach, boat docks and boat rentals. Great location"
United States
Jill
The price is AU$262
includes taxes & fees
1 July - 2 July
Breezy Palms Resort

Treasure Harbor

Treasure Harbor
3.0 star property
Islamorada
9.0 out of 10, Wonderful, (158 reviews)
"Amazing stay!"
United States
Amanda
The price is AU$403
includes taxes & fees
23 June - 24 June
Treasure Harbor

Island Bay Resort

Island Bay Resort
2.5 star property
Tavernier
10.0 out of 10, Exceptional, (171 reviews)
"Very nice small resort."
United States
Dan
The price is AU$443
includes taxes & fees
16 June - 17 June
Island Bay Resort

Florida Keys Getaway - Slps 4 - Ocean View

Florida Keys Getaway - Slps 4 - Ocean View
Tavernier
9.8 out of 10, Exceptional, (31 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 AU$436
includes taxes & fees
16 June - 17 June
Florida Keys Getaway - Slps 4 - Ocean View

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

Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
Tavernier
10.0 out of 10, Exceptional, (115 reviews)
"Everything was wonderful! We enjoyed our stay very much. "
United States
Colleen D.
The price is AU$618
includes taxes & fees
29 June - 30 June
Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ

Amazing Ocean view condo

Amazing Ocean view condo
Tavernier
9.6 out of 10, Exceptional, (49 reviews)
"Unit was really nice. The only complaint was the pillows were the worst we have ever used anywhere. We did find a pillow in the closet that was a little less lumpy but very stained. The pool does get very crowded. The beach area is really cute but smelled pretty bad. Overall a great place!"
United States
joleen s.
The price is AU$515
includes taxes & fees
16 June - 17 June
Amazing Ocean view condo

Charming Home in Key Largo

Charming Home in Key Largo
Key Largo
9.8 out of 10, Exceptional, (37 reviews)
"The condo is extremely clean and has everything you need for your stay. "
United States
hillary w.
The price is AU$569
includes taxes & fees
16 June - 17 June
Charming Home in Key Largo

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.
Flamingo Flats Ocean Pointe 5306 2BR/2BA

Serene Oceanfront Keys Condo

Serene Oceanfront Keys Condo
Tavernier
10.0 out of 10, Exceptional, (39 reviews)
"Beautifully decorated room with wonderful amenities. We appreciated the full kitchen, comfy beds and early morning ocean views. Kids loved the pool! "
Canada
Alicia
The price is AU$645
includes taxes & fees
16 June - 17 June
Serene Oceanfront Keys Condo

OP-2 Ocean View w/heated pool beach marina

OP-2 Ocean View w/heated pool beach marina
Tavernier
8.6 out of 10, Excellent, (12 reviews)
"Great location, thoughtful set-up. "
United States
Michelle J.
The price is AU$471
includes taxes & fees
23 June - 24 June
OP-2 Ocean View w/heated pool beach marina

Private 2-bedroom apartment with kitchen in lovely Tavernier, Key Largo

Private 2-bedroom apartment with kitchen in lovely Tavernier, Key Largo
Tavernier
10.0 out of 10, Exceptional, (4 reviews)
"Everything was perfect!Apartment was roomy and clean.And communication with manager Yohan was excellent.We had a great time!BTW....... there's a Winn Dixie just south of the property on the right.No need to drive the miles north to Publix......like I did!"
United States
Michael P.
The price is AU$519
includes taxes & fees
23 June - 24 June
Private 2-bedroom apartment with kitchen in lovely Tavernier, Key Largo

Boho Chic Ocean Pointe 3214

Boho Chic Ocean Pointe 3214
Tavernier
9.8 out of 10, Exceptional, (15 reviews)
"The condo was nice and clean. The view from the balcony is very nice. The property is also nice with things to do but not too busy. The host was great and responsive. "
United States
Anthony F.
The price is AU$612
includes taxes & fees
16 June - 17 June
Boho Chic Ocean Pointe 3214

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

Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
Tavernier
10.0 out of 10, Exceptional, (168 reviews)
"Condo was beautiful would definitely stay here again."
United States
Dan M.
The price is AU$639
includes taxes & fees
29 June - 30 June
Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ

Family-Friendly 1BR w/ Partial Ocean View & Pool

Family-Friendly 1BR w/ Partial Ocean View & Pool
Tavernier
Family-Friendly 1BR w/ Partial Ocean View & Pool

OP-3 Ocean Pointe Suite

OP-3 Ocean Pointe Suite
Tavernier
7.4 out of 10, Good, (3 reviews)
"Water view was beautiful. Restaurant was convenient and food was great. Pool was beautiful and very nice. "
United States
Shael B.
The price is AU$479
includes taxes & fees
21 June - 22 June
OP-3 Ocean Pointe Suite

Aqua Vista Ocean Pointe 3307

Aqua Vista Ocean Pointe 3307
Tavernier
9.6 out of 10, Exceptional, (4 reviews)
"All staff gave off a good vibe - happy-wanting to help - friendly. Amenities were as shown on the website and we all had a good time"
United States
Diane D.
Aqua Vista Ocean Pointe 3307

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)
"We were two couples staying in this space with plenty of room. All the amenities on this property (pool, beach restaurant and bar)made this a terrific stay. "
United States
Donna B.
The price is AU$666
includes taxes & fees
6 July - 7 July
4 Flr |2 Mastr |Oceanview |Jacuzzi |Beach |Marina

Cozy 1-bedroom apartment with kitchen in peaceful Tavernier/Key largo

Cozy 1-bedroom apartment with kitchen in peaceful Tavernier/Key largo
Tavernier
10.0 out of 10, Exceptional, (4 reviews)
"Very clean with everything you could need for your time in the Florida keys! The host was very responsive and helpful. Perfect place for a weekend with our dog."
United States
Anonymous traveller
The price is AU$342
includes taxes & fees
22 June - 23 June
Cozy 1-bedroom apartment with kitchen in peaceful Tavernier/Key largo

Island Sanctuary Islamorada

Island Sanctuary Islamorada
Tavernier
9.6 out of 10, Exceptional, (24 reviews)
"Great spot on the water for a unique experience! Kelly was very accommodating. "
United States
Lauren H.
The price is AU$598
includes taxes & fees
16 June - 17 June
Island Sanctuary Islamorada

Modern and Coastal Ocean Pointe 2307

Modern and Coastal Ocean Pointe 2307
Tavernier
10.0 out of 10, Exceptional, (133 reviews)
"We had a great stay at the Finch’s in Tavernier, FL. The condo was clean, comfortable, and in a great location for enjoying the Keys. Everything was as described, and the hosts were helpful and easy to communicate with. It was a relaxing spot for our trip, and we’d definitely stay here again."
United States
Parker O.
Modern and Coastal Ocean Pointe 2307
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$262 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 Private Oceanfront: Heated Pool, Paddleboards & Kayaks - 180 degree ocean views and Private Beachfront Paradise.

How many holiday rentals are there in Islamorada?

With 406 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 Founders 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 Robbie’s of Islamorada 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.