A beach with white lounge chairs, a covered pavilion, and palm trees.

Islamorada Holiday Rentals

  • 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

1. Breezy Palms Resort

Breezy Palms Resort
2.5 star property
Matecumbe
8.8 out of 10, Excellent, (746 reviews)
"Great resorts - will return again. Highly recommend"
United States
Lourdes
The price is AU$152
includes taxes & fees
15 Sept - 16 Sept
Breezy Palms Resort

2. Treasure Harbor

Treasure Harbor
3.0 star property
Islamorada
9.0 out of 10, Wonderful, (176 reviews)
"We loved sitting in the deck in the evening and again in the morning."
Canada
Molly
The price is AU$378
includes taxes & fees
1 Oct - 2 Oct
Treasure Harbor

3. Island Bay Resort

Island Bay Resort
2.5 star property
Tavernier
10.0 out of 10, Exceptional, (180 reviews)
"Amazing vacation spot!!"
United States
Katie Lyn
The price is AU$315
includes taxes & fees
29 Sept - 30 Sept
Island Bay Resort

4. Florida Keys Getaway - Slps 4 - Ocean View

Florida Keys Getaway - Slps 4 - Ocean View
Tavernier
9.8 out of 10, Exceptional, (38 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$434
includes taxes & fees
4 Oct - 5 Oct
Florida Keys Getaway - Slps 4 - Ocean View

5. Two Spectacular Ocean Views from the Living Room and Master Bedroom of the Condo

Two Spectacular Ocean Views from the Living Room and Master Bedroom of the Condo
Tavernier
9.6 out of 10, Exceptional, (233 reviews)
"Our stay was excellent. The home was immaculate and had everything we needed. We would definitely stay here again."
United States
Chris
Two Spectacular Ocean Views from the Living Room and Master Bedroom of the Condo

6. 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$532
includes taxes & fees
15 Sept - 16 Sept
Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ

7. Paradise Palms 2 Bedroom Condo Ocean Pointe 1206

Paradise Palms 2 Bedroom Condo Ocean Pointe 1206
Tavernier
9.8 out of 10, Exceptional, (7 reviews)
"Super clean and neat location!"
United States
Christopher R.
The price is AU$588
includes taxes & fees
15 Sept - 16 Sept
Paradise Palms 2 Bedroom Condo Ocean Pointe 1206

8. 4 Flr |2 Mastr |Oceanview |Jacuzzi |Beach |Marina

4 Flr |2 Mastr |Oceanview |Jacuzzi |Beach |Marina
Tavernier
9.8 out of 10, Exceptional, (48 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$765
includes taxes & fees
15 Sept - 16 Sept
4 Flr |2 Mastr |Oceanview |Jacuzzi |Beach |Marina

9. Lazy Daze Double King Suite Ocean Pointe 2310

Lazy Daze Double King Suite Ocean Pointe 2310
Tavernier
9.8 out of 10, Exceptional, (36 reviews)
"Loved the beach and pool."
United States
Haley P.
The price is AU$615
includes taxes & fees
15 Sept - 16 Sept
Lazy Daze Double King Suite Ocean Pointe 2310

10. 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, (30 reviews)
"The space was family friendly and worked well for our stay. The pool area was very clean and the Island Grill on site was great for snacks and drinks while we swam."
United States
Miranda J.
The price is AU$615
includes taxes & fees
19 Sept - 20 Sept
Starfish Seas Ocean Pointe 1302 King/Queen 2BA 2BR

11. Reel Key Largo Escape Ocean Pointe 5209

Reel Key Largo Escape Ocean Pointe 5209
Tavernier
9.6 out of 10, Exceptional, (10 reviews)
"We had a great time and the property was the center-point of our stay. Thanks for making it easy!"
United States
Ty L.
The price is AU$578
includes taxes & fees
19 Sept - 20 Sept
Reel Key Largo Escape Ocean Pointe 5209

12. Key Largo Baha Penthouse Ocean Pointe 1416

Key Largo Baha Penthouse Ocean Pointe 1416
Tavernier
9.8 out of 10, Exceptional, (27 reviews)
"Very nice penthouse and enjoyed our visit"
United States
Allen
The price is AU$586
includes taxes & fees
15 Sept - 16 Sept
Key Largo Baha Penthouse Ocean Pointe 1416

13. Ocean View 2BR/2BA Sleeps 6

Ocean View 2BR/2BA Sleeps 6
Tavernier
10.0 out of 10, Exceptional, (136 reviews)
"Very clean and comfortable, wonderful amenities, great view of the ocean, fantastic location and the hosts were so accessible and helpful. We thoroughly enjoyed our stay!"
United States
Deborah D.
The price is AU$601
includes taxes & fees
11 Oct - 12 Oct
Ocean View 2BR/2BA Sleeps 6

14. Boho Chic Ocean Pointe 3214 King & Queen

Boho Chic Ocean Pointe 3214 King & Queen
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$586
includes taxes & fees
19 Sept - 20 Sept
Boho Chic Ocean Pointe 3214 King & Queen

15. Charming Home in Key Largo

Charming Home in Key Largo
Key Largo
10.0 out of 10, Exceptional, (41 reviews)
"Very clean and nice location."
United States
Melinda V.
The price is AU$513
includes taxes & fees
15 Sept - 16 Sept
Charming Home in Key Largo

16. 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, (10 reviews)
"Such a beautiful condo! We loved our stay."
United States
Bethany B.
The price is AU$614
includes taxes & fees
28 Sept - 29 Sept
Sunrise Oasis - Top Floor 2 BR 2 BA Condo 2411

17. Sky Blue Escape Ocean Pointe 1314/2BA 2BR

Sky Blue Escape Ocean Pointe 1314/2BA 2BR
Tavernier
9.8 out of 10, Exceptional, (6 reviews)
"The place was exactly as advertised and the location was perfect! Our host was very informative and provided all the details for a seamless checkin."
United States
Bryan K.
The price is AU$599
includes taxes & fees
15 Sept - 16 Sept
Sky Blue Escape Ocean Pointe 1314/2BA 2BR

18. Ocean view condo with balcony/marina view

Ocean view condo with balcony/marina view
Tavernier
8.6 out of 10, Excellent, (46 reviews)
"Wonderful stay! Beautiful view from the balcony"
United States
Katy T.
The price is AU$579
includes taxes & fees
12 Oct - 13 Oct
Ocean view condo with balcony/marina view

19. Ocean Pointe - Pool, Hot Tub, View, Beach, Parking

Ocean Pointe - Pool, Hot Tub, View, Beach, Parking
Tavernier
10.0 out of 10, Exceptional, (3 reviews)
"Nelson was very responsive and a wonderful host. The unit was excellent! The best we have ever stayed in. We will most certainly be back "
United States
barbara m.
The price is AU$479
includes taxes & fees
16 Sept - 17 Sept
Ocean Pointe - Pool, Hot Tub, View, Beach, Parking

20. Ocean View Overlooking Marina Ocean Pointe 5305

Ocean View Overlooking Marina Ocean Pointe 5305
Tavernier
10.0 out of 10, Exceptional, (27 reviews)
"Great place to stay and if you are fishing this is the building closest to the fish cleaning station."
United States
Justin C.
The price is AU$607
includes taxes & fees
15 Sept - 16 Sept
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.
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, 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$152 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?

7 Bedroom with Dockage, Pool, Firepit, Paddle Boards & Kayaks : This highly rated holiday home rental in Islamorada is located by the ocean, and has an outdoor pool, a balcony and a BBQ to put you at ease in your new surroundings. It has 7 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 Single Family Home In Angler's Reef Gated Community, Beaches,Marina,Heated Pool.

How many holiday rentals are there in Islamorada?

With 402 Expedia holiday rentals, you're guaranteed to find just the right place for your Islamorada stay.

What can I see and do in Islamorada?

Islamorada County 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 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.