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
9.0 out of 10, Wonderful, (778 reviews)
"Such a great place to stay!!"
United States
Gavin
The price is £97
includes taxes & fees
10 Nov - 11 Nov
Breezy Palms Resort

2. Treasure Harbor

Treasure Harbor
3.0 star property
Islamorada
9.0 out of 10, Wonderful, (180 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 £194
includes taxes & fees
5 Nov - 6 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 £275
includes taxes & fees
16 Nov - 17 Nov
Florida Keys Getaway - Slps 4 - Ocean View

4. 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 £204
includes taxes & fees
11 Nov - 12 Nov
Cozy 1-bedroom apartment with kitchen in peaceful Tavernier/Key largo

5. 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 £245
includes taxes & fees
17 Nov - 18 Nov
Amazing Ocean view condo

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

Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
Tavernier
10.0 out of 10, Exceptional, (171 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 £276
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 £280
includes taxes & fees
19 Nov - 20 Nov
Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ

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 £388
includes taxes & fees
18 Nov - 19 Nov
4 Flr |2 Mastr |Oceanview |Jacuzzi |Beach |Marina

9. 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 £318
includes taxes & fees
18 Nov - 19 Nov
Flamingo Flats | Marina View | Ocean Pointe 5306

10. Aqua Vista | Ocean View 2BR | Ocean Pointe 3307

Aqua Vista | Ocean View 2BR | 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 £324
includes taxes & fees
12 Nov - 13 Nov
Aqua Vista | Ocean View 2BR | Ocean Pointe 3307

11. 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 £343
includes taxes & fees
17 Nov - 18 Nov
Lazy Daze | Double King Suite | Ocean Pointe 2310

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 £290
includes taxes & fees
17 Nov - 18 Nov
Charming Home in Key Largo

13. 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 £278
includes taxes & fees
14 Nov - 15 Nov
Ocean view condo with balcony/marina view

14. 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 £319
includes taxes & fees
9 Nov - 10 Nov
Your Happy Place - gorgeous 2 bed/2 bath oceanfront suite with full kitchen

15. 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 £329
includes taxes & fees
18 Nov - 19 Nov
Sunrise Sanctuary | Top Floor | Ocean Pointe 2415

16. 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 £350
includes taxes & fees
1 Dec - 2 Dec
2BR Condo w/ Ocean View, Pool & Tropical Setting

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 £266
includes taxes & fees
12 Nov - 13 Nov
Ocean Pointe Ocean View w/heated pool beach marina

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

Private 2-bedroom apartment with kitchen in lovely Tavernier, Key Largo
Tavernier
9.6 out of 10, Exceptional, (5 reviews)
"Host was very helpful and responsive! This was our first VRBO stay so we had more questions than seasoned guests, and he was very patient and helpful. Place was as advertised. Bed/pillows were very comfortable. AC was excellent. "
United States
Denise H.
The price is £288
includes taxes & fees
16 Nov - 17 Nov
Private 2-bedroom apartment with kitchen in lovely Tavernier, Key Largo

19. Tiki Time | Top Floor King | Ocean Pointe 1413

Tiki Time | Top Floor King | Ocean Pointe 1413
Tavernier
10.0 out of 10, Exceptional, (2 reviews)
"The host was excellent, they reached out often and very attentive. The condo is beautifully decorated and super clean. It is a small condo but perfect for a couple. It has numerous amenities and has lots of extras for your use. We would definitely stay here again!"
United States
Constance W.
The price is £297
includes taxes & fees
1 Dec - 2 Dec
Tiki Time | Top Floor King | Ocean Pointe 1413

20. Signature 1BR Partial Ocean View | Beach + Pool

Signature 1BR Partial Ocean View | Beach + Pool
Key Largo
10.0 out of 10, Exceptional, (1 review)
"Beautiful place, nice location"
United States
Michelle G.
The price is £163
includes taxes & fees
30 Nov - 1 Dec
Signature 1BR Partial Ocean View | Beach + Pool
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 £97 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 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.