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, (153 reviews)
"Amazing stay!"
United States
Amanda
The price is ¥24,089
¥49,373 total
includes taxes & fees
May 28 - May 29
Treasure Harbor

Breezy Palms Resort

Breezy Palms Resort
2.5 star property
Matecumbe
8.8 out of 10, Excellent, (676 reviews)
"Easy parking and great clean kitchen"
United States
JoAnn
The price is ¥19,865
¥24,881 total
includes taxes & fees
May 26 - May 27
Breezy Palms Resort

Island Bay Resort

Island Bay Resort
2.5 star property
Tavernier
10.0 out of 10, Exceptional, (168 reviews)
"Very nice small resort."
United States
Dan
The price is ¥45,518
¥51,207 total
includes taxes & fees
Jun 7 - Jun 8
Island Bay Resort

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 ¥29,934
¥69,312 total
includes taxes & fees
May 18 - May 19
Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ

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 ¥91,474
¥111,639 total
includes taxes & fees
May 20 - May 21
The Islands of Islamorada

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

Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
Tavernier
10.0 out of 10, Exceptional, (166 reviews)
"Very nice place. Clean and easy to contact the host."
United States
Bonnie H.
The price is ¥29,367
¥68,596 total
includes taxes & fees
May 18 - May 19
Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ

Charming Home in Key Largo

Charming Home in Key Largo
Key Largo
9.8 out of 10, Exceptional, (37 reviews)
"Comfortable and well thought out space."
United States
Jessica E.
The price is ¥22,807
¥64,857 total
includes taxes & fees
May 25 - May 26
Charming Home in Key Largo

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, (96 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 ¥29,934
¥51,437 total
includes taxes & fees
May 17 - May 18
Dazzling Ocean View Suite w/heated pool, beach, marina, tennis/pickleball

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, (8 reviews)
"Great location and clean"
United States
Matthew H.
The price is ¥26,925
¥70,047 total
includes taxes & fees
Jun 4 - Jun 5
Sunrise Oasis - Top Floor 2 BR 2 BA Condo 2411

3212 Across from Pool * King & Queen/Twin Bunk Bed

3212 Across from Pool * King & Queen/Twin Bunk Bed
Tavernier
9.8 out of 10, Exceptional, (157 reviews)
"Really enjoyed the location and the unit. "
United States
Teresa L.
3212 Across from Pool * King & Queen/Twin Bunk Bed

Ocean view condo with balcony/marina view

Ocean view condo with balcony/marina view
Tavernier
8.8 out of 10, Excellent, (44 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 ¥32,072
¥67,996 total
includes taxes & fees
May 18 - May 19
Ocean view condo with balcony/marina view

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, (241 reviews)
"Great place to stay"
United States
Llonda B.
The price is ¥39,685
¥78,576 total
includes taxes & fees
Jun 13 - Jun 14
Two Panoramic Ocean Views from the Living room and Master Bedroom in this Condo

Florida Keys Getaway - Slps 4 - Ocean View

Florida Keys Getaway - Slps 4 - Ocean View
Tavernier
9.8 out of 10, Exceptional, (30 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 ¥22,138
¥59,590 total
includes taxes & fees
May 30 - May 31
Florida Keys Getaway - Slps 4 - Ocean View

Serene Oceanfront Keys Condo

Serene Oceanfront Keys Condo
Tavernier
10.0 out of 10, Exceptional, (37 reviews)
"We enjoyed our stay. It was very convenient to where we needed to be. The apartment was well stocked and had a nice view. The beds were very comfortable as well and the host was very responsive! Would recommend staying here if you’re in the area. "
United States
Mark F.
The price is ¥32,502
¥69,257 total
includes taxes & fees
May 17 - May 18
Serene Oceanfront Keys Condo

Island Sanctuary Islamorada

Island Sanctuary Islamorada
Tavernier
9.6 out of 10, Exceptional, (24 reviews)
"What a neat experience, wonderful boat, waking up on the water was beautiful! Kelly was cery responsive to anything we needed!"
United States
Leanne W.
The price is ¥42,145
¥67,534 total
includes taxes & fees
May 19 - May 20
Island Sanctuary Islamorada

Key Largo 2BR w/ Partial Ocean Views & Pool

Key Largo 2BR w/ Partial Ocean Views & Pool
Tavernier
The price is ¥28,338
¥62,340 total
includes taxes & fees
May 18 - May 19
Key Largo 2BR w/ Partial Ocean Views & Pool

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, (17 reviews)
"Perfect Stay."
United States
suhaela s.
The price is ¥28,366
¥71,746 total
includes taxes & fees
May 27 - May 28
Your Happy Place - gorgeous 2 bed/2 bath oceanfront suite with full kitchen

4 Flr |2 Mastr |Oceanview |Jacuzzi |Beach |Marina

4 Flr |2 Mastr |Oceanview |Jacuzzi |Beach |Marina
Tavernier
9.8 out of 10, Exceptional, (47 reviews)
"There was no staff but the apartment was spotless and very well appointed with amenities like coffee, etc. Everything was clean, neat and new feeling. The beds were very comfortable and the apartment was spacious and welcoming with great views."
United States
Sandra
The price is ¥30,092
¥69,964 total
includes taxes & fees
May 27 - May 28
4 Flr |2 Mastr |Oceanview |Jacuzzi |Beach |Marina

Lazy Daze Double King Suite Ocean Pointe 2310

Lazy Daze Double King Suite Ocean Pointe 2310
Tavernier
9.8 out of 10, Exceptional, (31 reviews)
"Everything was exceptionally nice. Would definitely book again."
United States
Sharon
The price is ¥25,182
¥69,102 total
includes taxes & fees
May 17 - May 18
Lazy Daze Double King Suite Ocean Pointe 2310

Aqua Vista Ocean Pointe 3307

Aqua Vista Ocean Pointe 3307
Tavernier
10.0 out of 10, Exceptional, (3 reviews)
"Beautiful & perfect place for a getaway. Really enjoyed our stay. Highly recommend."
United States
Michelle
The price is ¥39,120
¥85,532 total
includes taxes & fees
Jun 12 - Jun 13
Aqua Vista Ocean Pointe 3307
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

Search for holiday rentals in Islamorada on Expedia! You can easily find your home rentals, villas, holiday apartments in Islamorada using one of the methods below:

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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?

Next available - August 2026 - Oceanfront - Heated Pool - Dock: This Islamorada vacation home rental is located on the beach and has an outdoor pool, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a rooftop terrace, a private yard, and a selection of games so you can immerse yourself in your vacation. Some other homes for rent in Islamorada include Bungalow #4 - 2 Bed/1 Bath & Pool in Islamorada and Anglers Reef Islamorada home with ocean views, private marina, beach & pool.

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?

Everglades National Park and Islamorada County 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 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.