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

Islamorada Vacation Rentals

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Our top choices for Islamorada vacation rentals

1. Breezy Palms Resort

Breezy Palms Resort
2.5 star property
Matecumbe
9.0 out of 10, Wonderful, (777 reviews)
"Such a great place to stay!!"
United States
Gavin
The price is CA $97
CA $181 total
includes taxes & fees
Nov 3 - Nov 4
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 CA $175
CA $393 total
includes taxes & fees
Nov 17 - Nov 18
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 CA $129
CA $448 total
includes taxes & fees
Nov 3 - Nov 4
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 CA $189
CA $489 total
includes taxes & fees
Oct 31 - Nov 1
Amazing Ocean view condo

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

Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
Tavernier
10.0 out of 10, Exceptional, (171 reviews)
"Perfect spot to stay in the keys! Great for fishing. The condo had everything you need to make your stay amazing. We will be back! Check in and out was a breeze, guards at gate were super friendly!"
United States
Pam K.
The price is CA $175
CA $506 total
includes taxes & fees
Nov 15 - Nov 16
Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ

6. 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 CA $249
CA $565 total
includes taxes & fees
Nov 2 - Nov 3
Ocean view condo with balcony/marina view

7. 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 CA $201
CA $576 total
includes taxes & fees
Oct 31 - Nov 1
Charming Home in Key Largo

8. Paradise Palms | 2 Balconies | Ocean Pointe 1206

Paradise Palms | 2 Balconies | Ocean Pointe 1206
Tavernier
9.8 out of 10, Exceptional, (8 reviews)
"Super clean and neat location!"
United States
Christopher R.
The price is CA $240
CA $657 total
includes taxes & fees
Nov 30 - Dec 1
Paradise Palms | 2 Balconies | Ocean Pointe 1206

9. Serene Oceanfront Keys Condo

Serene Oceanfront Keys Condo
Tavernier
9.8 out of 10, Exceptional, (44 reviews)
"Great stay, amazing pool and property, "
United States
Abbigail R.
The price is CA $220
CA $556 total
includes taxes & fees
Oct 31 - Nov 1
Serene Oceanfront Keys Condo

10. 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 CA $182
CA $515 total
includes taxes & fees
Nov 19 - Nov 20
Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ

11. Coastal Joy | Ocean View 2BR | Ocean Pointe 3412

Coastal Joy | Ocean View 2BR | Ocean Pointe 3412
Tavernier
9.4 out of 10, Exceptional, (3 reviews)
"Very clean. The view was amazing. Very comfortable beds. We are definitely coming back to this condo! "
United States
Jason U.
The price is CA $240
CA $656 total
includes taxes & fees
Oct 31 - Nov 1
Coastal Joy | Ocean View 2BR | Ocean Pointe 3412

12. 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 CA $264
CA $529 total
includes taxes & fees
Nov 29 - Nov 30
Dazzling Ocean View Suite w/heated pool, beach, marina, tennis/pickleball

13. 2BR Suite w/ Partial Ocean View & Beach Access

2BR Suite w/ Partial Ocean View & Beach Access
Key Largo
9.0 out of 10, Wonderful, (2 reviews)
"Great experience for our short stay in the upper Keys. Really nice and clean suite. Host was spot on. Large grounds with ample room."
United States
Richard E.
The price is CA $270
CA $341 total
includes taxes & fees
Nov 2 - Nov 3
2BR Suite w/ Partial Ocean View & Beach Access

14. 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 CA $224
CA $637 total
includes taxes & fees
Nov 15 - Nov 16
Aqua Vista | Ocean View 2BR | Ocean Pointe 3307

15. Starfish Seas | Ocean View | Ocean Pointe 1302

Starfish Seas | Ocean View | Ocean Pointe 1302
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 CA $264
CA $689 total
includes taxes & fees
Oct 31 - Nov 1
Starfish Seas | Ocean View | Ocean Pointe 1302

16. 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 CA $139
CA $416 total
includes taxes & fees
Nov 2 - Nov 3
Cozy 1-bedroom apartment with kitchen in peaceful Tavernier/Key largo

17. 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 CA $264
CA $688 total
includes taxes & fees
Nov 30 - Dec 1
Lazy Daze | Double King Suite | Ocean Pointe 2310

18. 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)
"Loved this condo. Had all the amenities we needed and was super clean and tidy. Will definitely be staying here again. "
United States
Rodney B.
The price is CA $240
CA $658 total
includes taxes & fees
Oct 31 - Nov 1
Blue Haven | Nature View 2BR | Ocean Pointe 1315

19. Sunrise Oasis | Top Floor | Ocean Pointe 2411

Sunrise Oasis | Top Floor | Ocean Pointe 2411
Tavernier
10.0 out of 10, Exceptional, (11 reviews)
"Such a beautiful condo! We loved our stay."
United States
Bethany B.
The price is CA $271
CA $698 total
includes taxes & fees
Nov 29 - Nov 30
Sunrise Oasis | Top Floor | Ocean Pointe 2411

20. Across from Pool | Sleeps 6 | Ocean Pointe 3212

Across from Pool | Sleeps 6 | Ocean Pointe 3212
Tavernier
9.8 out of 10, Exceptional, (160 reviews)
"Great place!"
United States
Anonymous traveller
The price is CA $278
CA $705 total
includes taxes & fees
Nov 1 - Nov 2
Across from Pool | Sleeps 6 | Ocean Pointe 3212
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 vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Islamorada vacation rental for you. At Expedia, you can take your pick from private vacation 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Islamorada vacation 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 vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Islamorada vacation rentals we have selected for you start as low as CA $181 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 vacation 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 vacation.

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 vacation rental in Islamorada?

Yes, we have vacation rentals in Islamorada close to MoradaWay Arts & Cultural District, or you can select a secluded option if you want 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 vacation home rentals that Islamorada has to offer?

Bungalow #4 - 2 Bed/1 Bath & Pool in Islamorada: This Islamorada vacation home rental offers an outdoor pool, a balcony, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave. Make the most of the 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 vacation rentals are there in Islamorada?

With 403 Expedia vacation rentals, you're sure 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 vacation rental in Islamorada like?

A vacation rental is a private property where you can stay for a couple of days or more in Islamorada. Vacation rentals provide amenities such as kitchens and laundry facilities so you'll have a home away from home. If you're concerned about cleanliness, a vacation rental can provide a sense of safety away from shared hotel elevators and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a traditional hotel, which makes a vacation rental a popular option for family trips or small group gatherings.