Islamorada Vacation Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Islamorada vacation rentals

Island Bay Resort

Island Bay Resort
2.5 star property
Tavernier
10.0 out of 10, Exceptional, (171 reviews)
"Very nice small resort."
United States
Dan
The price is CA $377
CA $424 total
includes taxes & fees
Jun 16 - Jun 17
Island Bay Resort

Breezy Palms Resort

Breezy Palms Resort
2.5 star property
Matecumbe
8.8 out of 10, Excellent, (697 reviews)
"Cute lil resort with pool, beach, boat docks and boat rentals. Great location"
United States
Jill
The price is CA $165
CA $258 total
includes taxes & fees
Jul 1 - Jul 2
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 CA $178
CA $397 total
includes taxes & fees
Jun 28 - Jun 29
Treasure Harbor

The Islands of Islamorada

The Islands of Islamorada
4.0 star property
Matecumbe
9.6 out of 10, Exceptional, (76 reviews)
"What a wonderful venue for our last 2 nights in the Keys. This place is a hidden gem. The entire staff, especially Edith, the bartender, were fantastic."
United States
Michael
The price is CA $894
CA $1,083 total
includes taxes & fees
Jul 6 - Jul 7
The Islands of Islamorada

Caloosa Cove Resort by CoolVacay

Caloosa Cove Resort by CoolVacay
3.0 star property
Matecumbe
9.6 out of 10, Exceptional, (4 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 CA $235
CA $312 total
includes taxes & fees
Jun 17 - Jun 18
Caloosa Cove Resort by CoolVacay

Charming Home in Key Largo

Charming Home in Key Largo
Key Largo
9.8 out of 10, Exceptional, (37 reviews)
"The condo is extremely clean and has everything you need for your stay. "
United States
hillary w.
The price is CA $195
CA $567 total
includes taxes & fees
Jun 16 - Jun 17
Charming Home in Key Largo

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 CA $264
CA $619 total
includes taxes & fees
Jul 1 - Jul 2
Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ

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 CA $280
CA $639 total
includes taxes & fees
Jun 22 - Jun 23
Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ

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 CA $236
CA $351 total
includes taxes & fees
Jun 16 - Jun 17
Coastal Studio Getaway – Second Floor with Partial Water Views

Double the Views: Florida Keys 1BR with 2 Balconies & Pool Access

Double the Views: Florida Keys 1BR with 2 Balconies & Pool Access
Matecumbe
10.0 out of 10, Exceptional, (10 reviews)
"Old Florida vibe with modern, clean condos. Perfect location to visit the Keys. "
United States
Beckie F.
The price is CA $354
CA $500 total
includes taxes & fees
Jun 16 - Jun 17
Double the Views: Florida Keys 1BR with 2 Balconies & Pool Access

Amazing Ocean view condo

Amazing Ocean view condo
Tavernier
9.6 out of 10, Exceptional, (49 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 CA $205
CA $509 total
includes taxes & fees
Jun 16 - Jun 17
Amazing Ocean view condo

Florida Keys Getaway - Slps 4 - Ocean View

Florida Keys Getaway - Slps 4 - Ocean View
Tavernier
9.8 out of 10, Exceptional, (31 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 CA $113
CA $428 total
includes taxes & fees
Jun 16 - Jun 17
Florida Keys Getaway - Slps 4 - Ocean View

Ocean view condo with balcony/marina view

Ocean view condo with balcony/marina view
Tavernier
8.6 out of 10, Excellent, (45 reviews)
"Rooms were spacious and a short drive to most of the attractions we wanted to do. Rooms and bathrooms were gorgeous!"
United States
Cindy
The price is CA $285
CA $609 total
includes taxes & fees
Jun 16 - Jun 17
Ocean view condo with balcony/marina view

OP-2 Ocean View w/heated pool beach marina

OP-2 Ocean View w/heated pool beach marina
Tavernier
8.6 out of 10, Excellent, (12 reviews)
"Great location, thoughtful set-up. "
United States
Michelle J.
The price is CA $273
CA $471 total
includes taxes & fees
Jun 22 - Jun 23
OP-2 Ocean View w/heated pool beach marina

Key Largo Kawama villa K1, 3/3

Key Largo Kawama villa K1, 3/3
Key Largo
9.8 out of 10, Exceptional, (189 reviews)
"Great place, the lake outside was amazing. Would stay here again. "
United States
Spencer H.
The price is CA $514
CA $981 total
includes taxes & fees
Jun 17 - Jun 18
Key Largo Kawama villa K1, 3/3

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, (20 reviews)
"Perfect Stay."
United States
suhaela s.
The price is CA $278
CA $672 total
includes taxes & fees
Jul 2 - Jul 3
Your Happy Place - gorgeous 2 bed/2 bath oceanfront suite with full kitchen

Blue Haven Key Largo | Ocean Pointe 1315

Blue Haven Key Largo | Ocean Pointe 1315
Tavernier
9.8 out of 10, Exceptional, (16 reviews)
"The unit was clean. The bed was comfortable. Everything worked well."
United States
William G.
The price is CA $222
CA $610 total
includes taxes & fees
Jun 17 - Jun 18
Blue Haven Key Largo | Ocean Pointe 1315

Modern and Coastal Ocean Pointe 2307

Modern and Coastal Ocean Pointe 2307
Tavernier
10.0 out of 10, Exceptional, (133 reviews)
"We had a great stay at the Finch’s in Tavernier, FL. The condo was clean, comfortable, and in a great location for enjoying the Keys. Everything was as described, and the hosts were helpful and easy to communicate with. It was a relaxing spot for our trip, and we’d definitely stay here again."
United States
Parker O.
The price is CA $238
CA $631 total
includes taxes & fees
Jun 22 - Jun 23
Modern and Coastal Ocean Pointe 2307

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, (97 reviews)
"Right in the heart of Key Largo but just off the beaten path. Clean, comfortable and cozy. The property has a beach, pool and restaurant which was convenient after a long day of travel."
United States
jodi
The price is CA $315
CA $528 total
includes taxes & fees
Jul 6 - Jul 7
Dazzling Ocean View Suite w/heated pool, beach, marina, tennis/pickleball

Island Sanctuary Islamorada

Island Sanctuary Islamorada
Tavernier
9.6 out of 10, Exceptional, (24 reviews)
"Great spot on the water for a unique experience! Kelly was very accommodating. "
United States
Lauren H.
The price is CA $371
CA $595 total
includes taxes & fees
Jun 16 - Jun 17
Island Sanctuary Islamorada
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Islamorada Hotel Reviews

Find out more about Islamorada

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Islamorada. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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 barbecue grill, 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 Oceanfront: Heated Pool, Paddleboards & Kayaks - 180 degree ocean views and Private Beachfront Paradise.

How many vacation rentals are there in Islamorada?

With 406 Expedia vacation rentals, you're sure 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 Robbie’s of Islamorada and Anne's Beach.

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.