Islamorada Holiday Rentals

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Our top choices for Islamorada holiday rentals

1. Breezy Palms Resort

Breezy Palms Resort
2.5 star property
Matecumbe
9.0 out of 10, Wonderful, (785 reviews)
"Such a great place to stay!!"
United States
Gavin
The price is NZ$279
includes taxes & fees
15 Nov - 16 Nov
Breezy Palms Resort

2. Treasure Harbor

Treasure Harbor
3.0 star property
Islamorada
9.0 out of 10, Wonderful, (184 reviews)
"Had a very enjoyable stay at Hemingway House. The place was spotless! All staff were very friendly and helpful. Would highly recommend staying here!"
United States
Diane
The price is NZ$499
includes taxes & fees
16 Nov - 17 Nov
Treasure Harbor

3. Florida Keys Getaway - Slps 4 - Ocean View

Florida Keys Getaway - Slps 4 - Ocean View
Tavernier
9.8 out of 10, Exceptional, (43 reviews)
"great stay and value! glad we went with this place for our trip, everyone loved it! beautiful, clean and the pool was great too!"
Canada
Nick
The price is NZ$605
includes taxes & fees
16 Nov - 17 Nov
Florida Keys Getaway - Slps 4 - Ocean View

4. Amazing Ocean view condo

Amazing Ocean view condo
Tavernier
9.6 out of 10, Exceptional, (53 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 NZ$588
includes taxes & fees
14 Nov - 15 Nov
Amazing Ocean view condo

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

Cozy 1-bedroom apartment with kitchen in peaceful Tavernier/Key largo
Tavernier
9.8 out of 10, Exceptional, (6 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 NZ$504
includes taxes & fees
15 Nov - 16 Nov
Cozy 1-bedroom apartment with kitchen in peaceful Tavernier/Key largo

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

Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
Tavernier
10.0 out of 10, Exceptional, (172 reviews)
"Beautifully appointed, clean and comfortable. This place is worth it! We had a great stay. Location is also excellent. Would definitely stay here again. "
United States
Erica C.
The price is NZ$634
includes taxes & fees
15 Nov - 16 Nov
Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ

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

Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
Tavernier
10.0 out of 10, Exceptional, (116 reviews)
"Fantastic place to stay! Very clean and great hosts. Will stay again. "
United States
Les
The price is NZ$637
includes taxes & fees
19 Nov - 20 Nov
Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ

8. Heavenly Hideaway | Ocean View | Ocean Pointe 3306

Heavenly Hideaway | Ocean View | Ocean Pointe 3306
Tavernier
10.0 out of 10, Exceptional, (4 reviews)
"Second time staying in this condo. Great view, clean, and really like the interior design. Looking forward to visiting again next year."
United States
Doug M.
The price is NZ$848
includes taxes & fees
17 Nov - 18 Nov
Heavenly Hideaway | Ocean View | Ocean Pointe 3306

9. Cozy studio apartment in tranquil Tavernier with AC and kitchen.

Cozy studio apartment in tranquil Tavernier with AC and kitchen.
Tavernier
The price is NZ$623
includes taxes & fees
16 Nov - 17 Nov
Cozy studio apartment in tranquil Tavernier with AC and kitchen.

10. Flamingo Flats | Marina View | Ocean Pointe 5306

Flamingo Flats | Marina View | Ocean Pointe 5306
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 NZ$759
includes taxes & fees
14 Nov - 15 Nov
Flamingo Flats | Marina View | Ocean Pointe 5306

11. 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 NZ$678
includes taxes & fees
14 Nov - 15 Nov
Ocean view condo with balcony/marina view

12. 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 NZ$626
includes taxes & fees
15 Nov - 16 Nov
Charming Home in Key Largo

13. 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 NZ$912
includes taxes & fees
18 Nov - 19 Nov
4 Flr |2 Mastr |Oceanview |Jacuzzi |Beach |Marina

14. Sunrise Sanctuary | Top Floor | Ocean Pointe 2415

Sunrise Sanctuary | Top Floor | Ocean Pointe 2415
Tavernier
9.8 out of 10, Exceptional, (20 reviews)
"Great stay"
United States
Blain R.
The price is NZ$772
includes taxes & fees
16 Nov - 17 Nov
Sunrise Sanctuary | Top Floor | Ocean Pointe 2415

15. 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)
"My host is amazing and the property was incredible. Highly recommended."
United States
Jean V.
The price is NZ$839
includes taxes & fees
13 Dec - 14 Dec
Lazy Daze | Double King Suite | Ocean Pointe 2310

16. 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 NZ$643
includes taxes & fees
15 Nov - 16 Nov
Dazzling Ocean View Suite w/heated pool, beach, marina, tennis/pickleball

17. Ocean Pointe Ocean View w/heated pool beach marina

Ocean Pointe Ocean View w/heated pool beach marina
Tavernier
8.6 out of 10, Excellent, (13 reviews)
"Great location and host is great with communication!"
United States
Mary Katherine B.
The price is NZ$621
includes taxes & fees
6 Dec - 7 Dec
Ocean Pointe Ocean View w/heated pool beach marina

18. 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
9.8 out of 10, Exceptional, (25 reviews)
"The property was in a great location, close to several beach bars and restaurants, the condo was so cute and the host was accessible throughout the entire process before and after our stay."
United States
Alicia
The price is NZ$787
includes taxes & fees
16 Nov - 17 Nov
Your Happy Place - gorgeous 2 bed/2 bath oceanfront suite with full kitchen

19. 2BR Condo w/ Ocean View, Pool & Tropical Setting

2BR Condo w/ Ocean View, Pool & Tropical Setting
Tavernier
9.6 out of 10, Exceptional, (4 reviews)
" centrally located for keys travel"
United States
Gary
The price is NZ$828
includes taxes & fees
30 Nov - 1 Dec
2BR Condo w/ Ocean View, Pool & Tropical Setting

20. Blue Haven | Nature View 2BR | Ocean Pointe 1315

Blue Haven | Nature View 2BR | Ocean Pointe 1315
Tavernier
9.8 out of 10, Exceptional, (17 reviews)
"Wonderful place and area 10/10"
United States
Ryan H.
The price is NZ$781
includes taxes & fees
15 Nov - 16 Nov
Blue Haven | Nature View 2BR | Ocean Pointe 1315
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.

Find holiday rentals that suit your style

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$279 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?

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 Bungalow #3 - 2 Bed/1 Bath & Pool in Islamorada.

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?

Anne's Beach and Fiesta Key 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.

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