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Our top choices for Islamorada holiday rentals

Breezy Palms Resort

Breezy Palms Resort
2.5 star property
Matecumbe
8.8 out of 10, Excellent, (699 reviews)
"Enjoyed this place."
United States
Christopher
The price is £141
includes taxes & fees
1 Jul - 2 Jul
Breezy Palms Resort

Treasure Harbor

Treasure Harbor
3.0 star property
Islamorada
9.0 out of 10, Wonderful, (158 reviews)
"Amazing stay!"
United States
Amanda
The price is £242
includes taxes & fees
1 Jul - 2 Jul
Treasure Harbor

Caloosa Cove Resort by CoolVacay

Caloosa Cove Resort by CoolVacay
3.0 star property
Matecumbe
9.6 out of 10, Exceptional, (5 reviews)
"Easy check in if you come After business hours. Kayaks and sport equipment available. Has a small beach which is unique to the Keys. Pool pretty much vacant at all times. Great views. Highly recommend."
United States
Dana
The price is £164
includes taxes & fees
23 Jun - 24 Jun
Caloosa Cove Resort by CoolVacay

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 £330
includes taxes & fees
22 Jun - 23 Jun
Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ

Florida Keys Getaway - Slps 4 - Ocean View

Florida Keys Getaway - Slps 4 - Ocean View
Tavernier
9.8 out of 10, Exceptional, (32 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 £249
includes taxes & fees
7 Jul - 8 Jul
Florida Keys Getaway - Slps 4 - Ocean View

Charming Home in Key Largo

Charming Home in Key Largo
Key Largo
9.8 out of 10, Exceptional, (38 reviews)
"The condo is extremely clean and has everything you need for your stay. "
United States
hillary w.
The price is £310
includes taxes & fees
22 Jun - 23 Jun
Charming Home in Key Largo

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

Cozy 1-bedroom apartment with kitchen in peaceful Tavernier/Key largo
Tavernier
10.0 out of 10, Exceptional, (4 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 £181
includes taxes & fees
22 Jun - 23 Jun
Cozy 1-bedroom apartment with kitchen in peaceful Tavernier/Key largo

Amazing Ocean view condo

Amazing Ocean view condo
Tavernier
9.6 out of 10, Exceptional, (50 reviews)
"Unit was really nice. The only complaint was the pillows were the worst we have ever used anywhere. We did find a pillow in the closet that was a little less lumpy but very stained. The pool does get very crowded. The beach area is really cute but smelled pretty bad. Overall a great place!"
United States
joleen s.
The price is £285
includes taxes & fees
1 Jul - 2 Jul
Amazing Ocean view condo

Island Bay Resort

Island Bay Resort
2.5 star property
Tavernier
10.0 out of 10, Exceptional, (172 reviews)
"Very nice small resort."
United States
Dan
The price is £249
includes taxes & fees
8 Jul - 9 Jul
Island Bay Resort

Sunrise Escape - Ocean Front Villa - Sleeps 10

Sunrise Escape - Ocean Front Villa - Sleeps 10
Key Largo
9.8 out of 10, Exceptional, (71 reviews)
"Host was very responsive, location safe and wuiet."
United States
Tracey C.
The price is £564
includes taxes & fees
23 Jun - 24 Jun
Sunrise Escape - Ocean Front Villa - Sleeps 10

Flip-Flops & Sunshine: Islamorada Studio Escape

Flip-Flops & Sunshine: Islamorada Studio Escape
Matecumbe
10.0 out of 10, Exceptional, (6 reviews)
"Very nice clean place. Pool amazing with great views of ocean"
United States
Dawn S.
The price is £192
includes taxes & fees
25 Jun - 26 Jun
Flip-Flops & Sunshine: Islamorada Studio Escape

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

Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
Tavernier
10.0 out of 10, Exceptional, (168 reviews)
"Condo was beautiful would definitely stay here again."
United States
Dan M.
The price is £322
includes taxes & fees
22 Jun - 23 Jun
Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ

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 £279
includes taxes & fees
22 Jun - 23 Jun
Private 2-bedroom apartment with kitchen in lovely Tavernier, Key Largo

Coastal Studio Getaway – Second Floor with Partial Water Views

Coastal Studio Getaway – Second Floor with Partial Water Views
Matecumbe
9.6 out of 10, Exceptional, (7 reviews)
"laid back and comfortable. "
United States
Joe M.
The price is £192
includes taxes & fees
22 Jun - 23 Jun
Coastal Studio Getaway – Second Floor with Partial Water Views

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
10.0 out of 10, Exceptional, (21 reviews)
"Cute place! Plenty of room for our family with beautiful view from the balcony. The pool and beach were perfect. We’d stay again! "
United States
Erin G.
The price is £356
includes taxes & fees
21 Jul - 22 Jul
Your Happy Place - gorgeous 2 bed/2 bath oceanfront suite with full kitchen

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 with a wonderful view. It has everything you need in the kitchen. We would definitely stay there again. "
United States
Edwina S.
The price is £366
includes taxes & fees
21 Jun - 22 Jun
Ocean View Overlooking Marina Ocean Pointe 5305

Captains Quarters Ocean Pointe 4405

Captains Quarters Ocean Pointe 4405
Tavernier
10.0 out of 10, Exceptional, (14 reviews)
"We had a very pleasant weekend away with all the comforts of home, yet even better with the amazing view! Great communication with the host with quick pleasant responses. The property is conveniently located and easy to get around. "
United States
Debbie W.
The price is £368
includes taxes & fees
21 Jun - 22 Jun
Captains Quarters Ocean Pointe 4405

Serene Oceanfront Keys Condo

Serene Oceanfront Keys Condo
Tavernier
10.0 out of 10, Exceptional, (39 reviews)
"Beautifully decorated room with wonderful amenities. We appreciated the full kitchen, comfy beds and early morning ocean views. Kids loved the pool! "
Canada
Alicia
The price is £342
includes taxes & fees
23 Jun - 24 Jun
Serene Oceanfront Keys Condo

Modern and Coastal Ocean Pointe 2307

Modern and Coastal Ocean Pointe 2307
Tavernier
10.0 out of 10, Exceptional, (133 reviews)
"There’s plenty to do for families of all ages at Ocean Pointe, and the condo was an extremely comfortable place to do it from. The hosts made us feel welcome, and we appreciated their care. "
United States
Sherry G.
The price is £348
includes taxes & fees
1 Jul - 2 Jul
Modern and Coastal Ocean Pointe 2307

Cozy Waterfront Apartment in Key Largo!

Cozy Waterfront Apartment in Key Largo!
Key Largo
9.8 out of 10, Exceptional, (12 reviews)
"We loved our stay at the waterfront cabanas! The location is 10/10 with an awesome waterfront bar/restaurant and coffee truck within walking distance. We truly felt like keys locals staying here - highly recommend! "
United States
Brittany M.
The price is £259
includes taxes & fees
22 Jun - 23 Jun
Cozy Waterfront Apartment in Key Largo!
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 £141 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 BBQ and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave. Some other homes for rent in Islamorada include Private Beachfront Paradise and Private Oceanfront: Heated Pool, Paddleboards & Kayaks - 180 degree ocean views.

How many holiday rentals are there in Islamorada?

With 415 Expedia holiday rentals, you're guaranteed to find just the right place for your Islamorada stay.

What can I see and do in Islamorada?

Everglades National 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.