Islamorada Vacation Rentals

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Our top choices for Islamorada vacation rentals

Island Bay Resort

Island Bay Resort
2.5 star property
Tavernier
10.0 out of 10, Exceptional, (165 reviews)
"Very nice small resort."
United States
Dan
$293 nightly
The price is $329
Jun 3 - Jun 4
Total with taxes and fees
Island Bay Resort

Treasure Harbor

Treasure Harbor
3.0 star property
Islamorada
9.0 out of 10, Wonderful, (153 reviews)
"Amazing stay!"
United States
Amanda
$264 nightly
The price is $297
May 7 - May 8
Total with taxes and fees
Treasure Harbor

Breezy Palms Resort

Breezy Palms Resort
2.5 star property
Matecumbe
8.8 out of 10, Excellent, (671 reviews)
"Place was nicer inside than out. Great location."
United States
Marcos
$128 nightly
The price is $143
May 13 - May 14
Total with taxes and fees
Breezy Palms Resort

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
$627 nightly
The price is $705
May 11 - May 12
Total with taxes and fees
The Islands of Islamorada

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, (240 reviews)
"Great place to stay"
United States
Llonda B.
$372 nightly
The price is $413
May 7 - May 8
Total with taxes and fees
Two Panoramic Ocean Views from the Living room and Master Bedroom in this Condo

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
$387 nightly
The price is $429
May 7 - May 8
Total with taxes and fees
Ocean view condo with balcony/marina view

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.
$405 nightly
The price is $450
May 25 - May 26
Total with taxes and fees
Your Happy Place - gorgeous 2 bed/2 bath oceanfront suite with full kitchen

Dazzling Ocean Pointe -OP-Main

Dazzling Ocean Pointe -OP-Main
Tavernier
9.0 out of 10, Wonderful, (95 reviews)
"Cleanliness, location, communication and the pool was just great! Thank you so very much!"
United States
Vicky W.
$294 nightly
The price is $327
May 11 - May 12
Total with taxes and fees
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, (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.
$401 nightly
The price is $445
May 7 - May 8
Total with taxes and fees
Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ

Paradise Palms 2 Bedroom Condo Ocean Pointe 1206

Paradise Palms 2 Bedroom Condo Ocean Pointe 1206
Tavernier
9.8 out of 10, Exceptional, (6 reviews)
"Super clean and neat location!"
United States
Christopher R.
$393 nightly
The price is $426
May 17 - May 18
Total with taxes and fees
Paradise Palms 2 Bedroom Condo Ocean Pointe 1206

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, (29 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
$400 nightly
The price is $434
May 13 - May 14
Total with taxes and fees
Starfish Seas Ocean Pointe 1302 King/Queen 2BA 2BR

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.
$429 nightly
The price is $467
May 10 - May 11
Total with taxes and fees
3212 Across from Pool * King & Queen/Twin Bunk Bed

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.
$396 nightly
The price is $429
May 20 - May 21
Total with taxes and fees
Blue Haven Key Largo | Ocean Pointe 1315

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.
$395 nightly
The price is $429
May 10 - May 11
Total with taxes and fees
Sunrise Oasis - Top Floor 2 BR 2 BA Condo 2411

2BR Condo w/ Ocean View, Pool & Tropical Setting

2BR Condo w/ Ocean View, Pool & Tropical Setting
Tavernier
9.6 out of 10, Exceptional, (4 reviews)
" centrally located for keys travel"
United States
Gary
$404 nightly
The price is $449
May 7 - May 8
Total with taxes and fees
2BR Condo w/ Ocean View, Pool & Tropical Setting

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
$398 nightly
The price is $432
May 14 - May 15
Total with taxes and fees
Aqua Vista Ocean Pointe 3307

Oceanside Kawama Villa R5

Oceanside Kawama Villa R5
Key Largo
9.2 out of 10, Wonderful, (180 reviews)
"Very very nice villa in a superb location… Abcolutely loved the property!"
United States
Ricardo G.
$560 nightly
The price is $620
May 7 - May 8
Total with taxes and fees
Oceanside Kawama Villa R5

Charming Home in Key Largo

Charming Home in Key Largo
Key Largo
9.8 out of 10, Exceptional, (37 reviews)
"We really enjoyed staying at this property"
United States
Deb P.
$368 nightly
The price is $409
May 11 - May 12
Total with taxes and fees
Charming Home in Key Largo

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.
$409 nightly
The price is $443
May 12 - May 13
Total with taxes and fees
Sea View and Sunrise Ocean Pointe 2412 2BA/2BR

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
$409 nightly
The price is $454
May 17 - May 18
Total with taxes and fees
Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
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, condos, resorts, cabins, villas, motels. 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 low season months. For more hustle and bustle, you may prefer to visit Islamorada in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $143 per night. Rates vary depending on your travel dates, location, and amenities so make a search and 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.

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 Oceanside Getaway: Beautiful Home with Boat Slip, Pool & Beach - Gated community.

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 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 Fiesta Key.

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.