Islamorada Vacation Rentals

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Our top choices for Islamorada vacation rentals

Treasure Harbor

Treasure Harbor
3.0 star property
Islamorada
9.0 out of 10, Wonderful, (152 reviews)
"Amazing stay!"
United States
Amanda
The price is CA $170
CA $382 total
includes taxes & fees
May 5 - May 6
Treasure Harbor

The Islands of Islamorada

The Islands of Islamorada
4.0 star property
Matecumbe
9.6 out of 10, Exceptional, (75 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 $815
CA $992 total
includes taxes & fees
May 11 - May 12
The Islands of Islamorada

Breezy Palms Resort

Breezy Palms Resort
2.5 star property
Matecumbe
8.8 out of 10, Excellent, (666 reviews)
"Clean room, good staff and convenience location for a visit."
United States
Judbelth
The price is CA $164
CA $256 total
includes taxes & fees
May 7 - May 8
Breezy Palms Resort

Two Panoramic Ocean Views from the Living room and Master Bedroom in this Condo

Two Panoramic Ocean Views from the Living room and Master Bedroom in this Condo
Tavernier
9.8 out of 10, Exceptional, (239 reviews)
"Great place to stay"
United States
Llonda B.
The price is CA $244
CA $568 total
includes taxes & fees
May 5 - May 6
Two Panoramic Ocean Views from the Living room and Master Bedroom in this Condo

Modern and Coastal Ocean Pointe 2307

Modern and Coastal Ocean Pointe 2307
Tavernier
10.0 out of 10, Exceptional, (130 reviews)
"Very nice property. Hosts were great. "
United States
Tad L.
The price is CA $253
CA $636 total
includes taxes & fees
May 10 - May 11
Modern and Coastal Ocean Pointe 2307

Island Sanctuary Islamorada

Island Sanctuary Islamorada
Tavernier
9.8 out of 10, Exceptional, (22 reviews)
"Kelly is the best host!!! Excellent views and comfort. It was magical for me and my wife. Thank you!"
United States
Aisel R.
The price is CA $361
CA $578 total
includes taxes & fees
May 5 - May 6
Island Sanctuary Islamorada

Ocean view condo with balcony/marina view

Ocean view condo with balcony/marina view
Tavernier
8.8 out of 10, Excellent, (43 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 $275
CA $587 total
includes taxes & fees
May 3 - May 4
Ocean view condo with balcony/marina view

Dazzling Ocean Pointe -OP-Main

Dazzling Ocean Pointe -OP-Main
Tavernier
9.0 out of 10, Wonderful, (94 reviews)
"Cleanliness, location, communication and the pool was just great! Thank you so very much!"
United States
Vicky W.
The price is CA $257
CA $447 total
includes taxes & fees
May 5 - May 6
Dazzling Ocean Pointe -OP-Main

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

Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
Tavernier
10.0 out of 10, Exceptional, (114 reviews)
"Fantastic place to stay! Very clean and great hosts. Will stay again. "
United States
Les
The price is CA $272
CA $621 total
includes taxes & fees
May 20 - May 21
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, (165 reviews)
"Everything was as described and we truly enjoyed our stay. We traveled with small children and the home was fit for them. It’s a true vacation place. I highly recommend staying! "
United States
keli p.
The price is CA $265
CA $612 total
includes taxes & fees
May 12 - May 13
Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ

Beautiful Kawama Townhouse

Beautiful Kawama Townhouse
Key Largo
9.8 out of 10, Exceptional, (147 reviews)
"The host, house and amenities were perfect. all praises.."
United States
Pete S.
The price is CA $412
CA $872 total
includes taxes & fees
May 3 - May 4
Beautiful Kawama Townhouse

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, (16 reviews)
"Perfect Stay."
United States
suhaela s.
The price is CA $194
CA $556 total
includes taxes & fees
May 5 - May 6
Your Happy Place - gorgeous 2 bed/2 bath oceanfront suite with full kitchen

Flamingo Flats Ocean Pointe 5306 2BR/2BA

Flamingo Flats Ocean Pointe 5306 2BR/2BA
Tavernier
9.6 out of 10, Exceptional, (8 reviews)
"Great location and prompt support with all questions we had. "
United States
Jim I.
The price is CA $227
CA $608 total
includes taxes & fees
May 5 - May 6
Flamingo Flats Ocean Pointe 5306 2BR/2BA

Casa Largo

Casa Largo
Key Largo
9.2 out of 10, Wonderful, (133 reviews)
"The unit was clean and beautiful. The entire complex was very nice, too. We had everything needed to enjoy our stay."
United States
Rhonda D.
The price is CA $322
CA $733 total
includes taxes & fees
May 3 - May 4
Casa Largo

Sunrise Oasis - Top Floor 2 BR 2 BA Condo 2411

Sunrise Oasis - Top Floor 2 BR 2 BA Condo 2411
Tavernier
10.0 out of 10, Exceptional, (7 reviews)
"Great location and clean"
United States
Matthew H.
The price is CA $219
CA $600 total
includes taxes & fees
May 27 - May 28
Sunrise Oasis - Top Floor 2 BR 2 BA Condo 2411

Sea View and Sunrise Ocean Pointe 2412 2BA/2BR

Sea View and Sunrise Ocean Pointe 2412 2BA/2BR
Tavernier
9.6 out of 10, Exceptional, (89 reviews)
"Good location"
United States
Dimitri O.
The price is CA $227
CA $603 total
includes taxes & fees
May 3 - May 4
Sea View and Sunrise Ocean Pointe 2412 2BA/2BR

Nauti Hideaway Ocean Pointe 2314

Nauti Hideaway Ocean Pointe 2314
Tavernier
10.0 out of 10, Exceptional, (2 reviews)
"Great communication. Very clean. We loved view from the room. We would definitely stay here again!"
United States
Cynthia L.
The price is CA $247
CA $635 total
includes taxes & fees
May 25 - May 26
Nauti Hideaway Ocean Pointe 2314

Blue Haven Key Largo | Ocean Pointe 1315

Blue Haven Key Largo | Ocean Pointe 1315
Tavernier
9.8 out of 10, Exceptional, (16 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 $208
CA $583 total
includes taxes & fees
May 5 - May 6
Blue Haven Key Largo | Ocean Pointe 1315

Starfish Seas Ocean Pointe 1302 King/Queen 2BA 2BR

Starfish Seas Ocean Pointe 1302 King/Queen 2BA 2BR
Tavernier
9.8 out of 10, Exceptional, (28 reviews)
"Beautiful condo with nice decor. We enjoyed the pool and was nice having a restaurant on site. I would definitely stay there again "
United States
Cathy
The price is CA $213
CA $589 total
includes taxes & fees
May 5 - May 6
Starfish Seas Ocean Pointe 1302 King/Queen 2BA 2BR

NEW ! Lagoon-front townhouse with Marina! Day Dreams Key Largo.

NEW ! Lagoon-front townhouse with Marina! Day Dreams Key Largo.
Key Largo
10.0 out of 10, Exceptional, (53 reviews)
"Had a great stay. Being so close to the lagoon we were able to launch the kayaks for our kids multiple times a day no problem. We saw tarpon, lobster, parrot fish and tons of other sea life right out the front door. And the pool was just as close. Also being on this side of the property it is a quick walk to the beach to watch the sunset. The unit seemed as if we were the first ones staying there after it had been renovated. Grew up in south Florida and had stopped coming back to visit but we...
United States
Jonathan D.
The price is CA $440
CA $902 total
includes taxes & fees
May 12 - May 13
NEW ! Lagoon-front townhouse with Marina! Day Dreams 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

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.

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 Next available - August 2026 - Oceanfront - Heated Pool - Dock and Islamorada Anglers Reef! “Sandbar Bungalow Villa" AMAZING! Middle row location! .

How many vacation rentals are there in Islamorada?

With 410 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 Anne's Beach 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.