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
The price is CA $232
CA $456 total
includes taxes & fees
Apr 25 - Apr 26
Treasure Harbor

Breezy Palms Resort

Breezy Palms Resort
2.5 star property
Matecumbe
8.8 out of 10, Excellent, (652 reviews)
"Clean room, good staff and convenience location for a visit."
United States
Judbelth
The price is CA $194
CA $290 total
includes taxes & fees
Apr 21 - Apr 22
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.
The price is CA $229
CA $531 total
includes taxes & fees
May 5 - May 6
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.
The price is CA $368
CA $586 total
includes taxes & fees
Apr 11 - Apr 12
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.
The price is CA $212
CA $594 total
includes taxes & fees
Apr 15 - Apr 16
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
The price is CA $201
CA $579 total
includes taxes & fees
Apr 15 - Apr 16
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
The price is CA $231
CA $620 total
includes taxes & fees
Apr 14 - Apr 15
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
The price is CA $217
CA $601 total
includes taxes & fees
May 10 - May 11
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
The price is CA $312
CA $676 total
includes taxes & fees
Apr 29 - Apr 30
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
The price is CA $455
CA $512 total
includes taxes & fees
Apr 13 - Apr 14
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.
The price is CA $258
CA $655 total
includes taxes & fees
Apr 13 - Apr 14
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.
The price is CA $217
CA $595 total
includes taxes & fees
May 5 - May 6
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.
The price is CA $212
CA $587 total
includes taxes & fees
May 5 - May 6
Blue Haven Key Largo | Ocean Pointe 1315

Dazzling Ocean Pointe -OP-Main

Dazzling Ocean Pointe -OP-Main
Tavernier
9.0 out of 10, Wonderful, (92 reviews)
"Cleanliness, location, communication and the pool was just great! Thank you so very much!"
United States
Vicky W.
The price is CA $262
CA $455 total
includes taxes & fees
Apr 29 - Apr 30
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
The price is CA $299
CA $625 total
includes taxes & fees
Apr 20 - Apr 21
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.
The price is CA $270
CA $624 total
includes taxes & fees
May 1 - May 2
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.
The price is CA $225
CA $611 total
includes taxes & fees
Apr 28 - Apr 29
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.
The price is CA $262
CA $455 total
includes taxes & fees
Apr 29 - Apr 30
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.
The price is CA $364
CA $770 total
includes taxes & fees
May 5 - May 6
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, (24 reviews)
"nice place !!"
United States
Jim H.
The price is CA $285
CA $691 total
includes taxes & fees
Apr 23 - Apr 24
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

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 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.