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

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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, (748 reviews)
"Great resorts - will return again. Highly recommend"
United States
Lourdes
The price is £74
includes taxes & fees
30 Sept - 1 Oct
Breezy Palms Resort

2. Treasure Harbor

Treasure Harbor
3.0 star property
Islamorada
9.0 out of 10, Wonderful, (175 reviews)
"We loved sitting in the deck in the evening and again in the morning."
Canada
Molly
The price is £203
includes taxes & fees
1 Oct - 2 Oct
Treasure Harbor

3. Island Bay Resort

Island Bay Resort
2.5 star property
Tavernier
9.8 out of 10, Exceptional, (183 reviews)
"Amazing vacation spot!!"
United States
Katie Lyn
The price is £168
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)
"Great place to stay down on the keys."
United States
GJ W.
The price is £234
includes taxes & fees
23 Sept - 24 Sept
Florida Keys Getaway - Slps 4 - Ocean View

5. 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 £288
includes taxes & fees
21 Sept - 22 Sept
Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ

6. Aqua Vista Ocean Pointe 3307

Aqua Vista Ocean Pointe 3307
Tavernier
9.6 out of 10, Exceptional, (4 reviews)
"Beautiful & perfect place for a getaway. Really enjoyed our stay. Highly recommend."
United States
Michelle
The price is £307
includes taxes & fees
24 Sept - 25 Sept
Aqua Vista Ocean Pointe 3307

7. Amazing Ocean view condo

Amazing Ocean view condo
Tavernier
9.6 out of 10, Exceptional, (52 reviews)
"Excellent accommodations. Unit was even nicer than it looked in pictures, everything was clean and in working order. Enjoyed our stay very much and would definitely stay here again!"
United States
Jerad E.
The price is £256
includes taxes & fees
21 Sept - 22 Sept
Amazing Ocean view condo

8. Charming Home in Key Largo

Charming Home in Key Largo
Key Largo
10.0 out of 10, Exceptional, (41 reviews)
"Awesome house, convenient to everything we needed. Super clean and everything was pretty modern. I would definitely stay again and would definitely recommend this property"
United States
JOHN P.
The price is £305
includes taxes & fees
1 Oct - 2 Oct
Charming Home in Key Largo

9. Sunrise Sanctuary - Top Floor Ocean Pointe 2415

Sunrise Sanctuary - Top Floor Ocean Pointe 2415
Tavernier
9.8 out of 10, Exceptional, (18 reviews)
"Great stay"
United States
Blain R.
The price is £312
includes taxes & fees
21 Sept - 22 Sept
Sunrise Sanctuary - Top Floor Ocean Pointe 2415

10. 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 £317
includes taxes & fees
26 Sept - 27 Sept
Reel Key Largo Escape Ocean Pointe 5209

11. Flamingo Flats Ocean Pointe 5306 2BR/2BA

Flamingo Flats Ocean Pointe 5306 2BR/2BA
Tavernier
9.6 out of 10, Exceptional, (9 reviews)
"Great location and prompt support with all questions we had. "
United States
Jim I.
The price is £309
includes taxes & fees
21 Sept - 22 Sept
Flamingo Flats Ocean Pointe 5306 2BR/2BA

12. 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 £413
includes taxes & fees
21 Sept - 22 Sept
4 Flr |2 Mastr |Oceanview |Jacuzzi |Beach |Marina

13. 2BR - Ocean View, Pool & Near Founders Park

2BR - Ocean View, Pool & Near Founders Park
Tavernier
9.4 out of 10, Exceptional, (8 reviews)
"We don’t get the email about how to check in so that was a bit bumpy but everything else was wonderful! Great place to stay!!!"
United States
Kristie
2BR - Ocean View, Pool & Near Founders Park

14. Ocean View Gem Ocean Pointe 3406 2BA/2BR King/Queen

Ocean View Gem Ocean Pointe 3406 2BA/2BR King/Queen
Tavernier
9.6 out of 10, Exceptional, (10 reviews)
"An awesome place to stay, fish and relax!"
United States
robert d.
The price is £329
includes taxes & fees
25 Sept - 26 Sept
Ocean View Gem Ocean Pointe 3406 2BA/2BR King/Queen

15. Sunrise Penthouse 3316 Ocean Pointe 1BR 2BA

Sunrise Penthouse 3316 Ocean Pointe 1BR 2BA
Tavernier
10.0 out of 10, Exceptional, (2 reviews)
"We enjoyed our stay! The space had everything we needed and was very comfortable. It is spacious, has an excellent bed and updated finishes. The pool is a great spot to hang out with plenty of chairs. The management team was very helpful and responsive to all of our needs (even on the 4th holiday!). Would definitely stay again."
United States
Chris
Sunrise Penthouse 3316 Ocean Pointe 1BR 2BA

16. 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 £334
includes taxes & fees
21 Sept - 22 Sept
Lazy Daze Double King Suite Ocean Pointe 2310

17. Keys Bohemian 2 BR 2 BA at Ocean Pointe 1312

Keys Bohemian 2 BR 2 BA at Ocean Pointe 1312
Tavernier
8.8 out of 10, Excellent, (3 reviews)
"Very clean and new"
United States
Dave H.
The price is £332
includes taxes & fees
21 Sept - 22 Sept
Keys Bohemian 2 BR 2 BA at Ocean Pointe 1312

18. 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, (103 reviews)
"Great visit!"
United States
Leigh D. H.
The price is £259
includes taxes & fees
21 Sept - 22 Sept
Dazzling Ocean View Suite w/heated pool, beach, marina, tennis/pickleball

19. 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 £341
includes taxes & fees
21 Sept - 22 Sept
Ocean View 2BR/2BA Sleeps 6

20. 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 £318
includes taxes & fees
21 Sept - 22 Sept
Boho Chic Ocean Pointe 3214 King & Queen
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, apart-hotels, 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 £74 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. 

Explore a world of travel with Expedia

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 balcony and a BBQ to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave. Make the most of garden in this rental home to help you unwind. Some other homes for rent in Islamorada include 7 Bedroom with Dockage, Pool, Firepit, Paddle Boards & Kayaks and Single Family Home In Angler's Reef Gated Community, Beaches,Marina,Heated Pool.

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?

Founders 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.