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, (148 reviews)
"Staff was great, rooms clean, views excellent"
United States
Diane
$286 nightly
The price is $322
Apr 14 - Apr 15
Total with taxes and fees
Treasure Harbor

Breezy Palms Resort

Breezy Palms Resort
2.5 star property
Matecumbe
8.8 out of 10, Excellent, (655 reviews)
"Clean room, good staff and convenience location for a visit."
United States
Judbelth
$176 nightly
The price is $198
Apr 12 - Apr 13
Total with taxes and fees
Breezy Palms Resort

Amazing Ocean view condo

Amazing Ocean view condo
Tavernier
9.6 out of 10, Exceptional, (46 reviews)
"Exceeded expectations, exceptionally clean, great for kids (they loved the pool), perfect for our Keys trip"
United States
Natalie M.
$344 nightly
The price is $382
May 11 - May 12
Total with taxes and fees
Amazing Ocean view condo

Island Sanctuary Islamorada

Island Sanctuary Islamorada
Tavernier
9.8 out of 10, Exceptional, (20 reviews)
"Kelly is the best host!!! Excellent views and comfort. It was magical for me and my wife. Thank you!"
United States
Aisel R.
$379 nightly
The price is $420
Apr 11 - Apr 12
Total with taxes and fees
Island Sanctuary Islamorada

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.
$387 nightly
The price is $420
May 4 - May 5
Total with taxes and fees
Paradise Palms 2 Bedroom Condo Ocean Pointe 1206

Reel Key Largo Escape Ocean Pointe 5209

Reel Key Largo Escape Ocean Pointe 5209
Tavernier
9.6 out of 10, Exceptional, (8 reviews)
"Great area"
United States
Yesenia
$393 nightly
The price is $426
Apr 14 - Apr 15
Total with taxes and fees
Reel Key Largo Escape Ocean Pointe 5209

Lazy Daze Double King Suite Ocean Pointe 2310

Lazy Daze Double King Suite Ocean Pointe 2310
Tavernier
9.8 out of 10, Exceptional, (30 reviews)
"Everything was exceptionally nice. Would definitely book again."
United States
Sharon
$404 nightly
The price is $438
Apr 13 - Apr 14
Total with taxes and fees
Lazy Daze Double King Suite Ocean Pointe 2310

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, (6 reviews)
"Clean, perfect place to stay for a couple nights. Being on the top floor was the best so we didn’t have to worry about people above us. "
United States
Natasha
$397 nightly
The price is $431
May 10 - May 11
Total with taxes and fees
Sunrise Oasis - Top Floor 2 BR 2 BA Condo 2411

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

Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
Tavernier
10.0 out of 10, Exceptional, (113 reviews)
"Fantastic place to stay! Very clean and great hosts. Will stay again. "
United States
Les
$437 nightly
The price is $485
Apr 26 - Apr 27
Total with taxes and fees
Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ

Island Bay Resort

Island Bay Resort
2.5 star property
Tavernier
10.0 out of 10, Exceptional, (156 reviews)
"Wonderful property and staff. Quite and beautiful!. "
United States
Ethan
$335 nightly
The price is $377
Apr 13 - Apr 14
Total with taxes and fees
Island Bay Resort

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.
$429 nightly
The price is $467
Apr 12 - Apr 13
Total with taxes and fees
Modern and Coastal Ocean Pointe 2307

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, (27 reviews)
"The place was clean, nicely decorated, and the kitchen was well equipped. No problems checking in. Pool was large and very nice."
United States
Dawn W.
$398 nightly
The price is $432
May 5 - May 6
Total with taxes and fees
Starfish Seas Ocean Pointe 1302 King/Queen 2BA 2BR

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.
$390 nightly
The price is $423
May 11 - May 12
Total with taxes and fees
Blue Haven Key Largo | Ocean Pointe 1315

Dazzling Ocean Pointe -OP-Main

Dazzling Ocean Pointe -OP-Main
Tavernier
9.0 out of 10, Wonderful, (93 reviews)
"Cleanliness, location, communication and the pool was just great! Thank you so very much!"
United States
Vicky W.
$286 nightly
The price is $319
Apr 29 - Apr 30
Total with taxes and fees
Dazzling Ocean Pointe -OP-Main

Ocean view condo with balcony/marina view

Ocean view condo with balcony/marina view
Tavernier
8.8 out of 10, Excellent, (42 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
$404 nightly
The price is $449
Apr 20 - Apr 21
Total with taxes and fees
Ocean view condo with balcony/marina view

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

Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
Tavernier
10.0 out of 10, Exceptional, (162 reviews)
"Amazing details definitely will be back !"
United States
Jamie P.
$401 nightly
The price is $445
May 1 - May 2
Total with taxes and fees
Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ

Boho Chic Ocean Pointe 3214

Boho Chic Ocean Pointe 3214
Tavernier
9.8 out of 10, Exceptional, (14 reviews)
"Wonderful unit; all amenities as listed, great location near the pool. Arrival/check in couldn’t be easier, and good communication with the property managers!We will stay here again!"
United States
Lorraine K.
$453 nightly
The price is $494
May 1 - May 2
Total with taxes and fees
Boho Chic Ocean Pointe 3214

OP-2 Ocean View w/heated pool beach marina

OP-2 Ocean View w/heated pool beach marina
Tavernier
8.4 out of 10, Very Good, (11 reviews)
"Great location, thoughtful set-up. "
United States
Michelle J.
$293 nightly
The price is $326
Apr 27 - Apr 28
Total with taxes and fees
OP-2 Ocean View w/heated pool beach marina

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.
$495 nightly
The price is $550
May 4 - May 5
Total with taxes and fees
Your Happy Place - gorgeous 2 bed/2 bath oceanfront suite with full kitchen

Key Largo Baha Penthouse Ocean Pointe 1416

Key Largo Baha Penthouse Ocean Pointe 1416
Tavernier
9.8 out of 10, Exceptional, (25 reviews)
"nice place !!"
United States
Jim H.
$445 nightly
The price is $484
Apr 23 - Apr 24
Total with taxes and fees
Key Largo Baha Penthouse Ocean Pointe 1416
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 $198 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 Private Oceanfront: Heated Pool, Paddleboards & Kayaks - 180 degree ocean views and May 2nd - 9th available Oceanfront - Heated Pool - Dock.

How many vacation rentals are there in Islamorada?

With 418 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.