Islamorada Vacation Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Islamorada vacation rentals

Houseboat in Islamorada

Treasure Harbor
3.0 star property
9.0 out of 10, Wonderful, (144 reviews)
"Staff was great, rooms clean, views excellent"
United States
Diane
The price is CA $249
CA $474 total
includes taxes & fees
Mar 24 - Mar 25
Treasure Harbor

Aparthotel in Matecumbe

Breezy Palms Resort
2.5 star property
8.8 out of 10, Excellent, (637 reviews)
"We enjoyed our stay! This was a better experience than the more expensive house one I paid in Key West. "
United States
Wendy
The price is CA $242
CA $343 total
includes taxes & fees
Apr 8 - Apr 9
Breezy Palms Resort
9.8 out of 10, Exceptional, (235 reviews)
"Great place to stay"
United States
Llonda B.
The price is CA $432
CA $810 total
includes taxes & fees
Apr 7 - Apr 8
Two Panoramic Ocean Views from the Living room and Master Bedroom in this Condo
8.8 out of 10, Excellent, (42 reviews)
"The condo was renovated, and very nicely decorated, very clean and cozy. We enjoyed our short stay. Community and pool were good too. "
United States
Lina
The price is CA $324
CA $654 total
includes taxes & fees
Apr 13 - Apr 14
Ocean view condo with balcony/marina view

Vacation Home in Key Largo

Charming Home in Key Largo
9.8 out of 10, Exceptional, (33 reviews)
"Very nice place and definitely would stay there again! Very nice host and redponded on time."
United States
Amey P.
The price is CA $216
CA $587 total
includes taxes & fees
Mar 29 - Mar 30
Charming Home in Key Largo
9.8 out of 10, Exceptional, (26 reviews)
"Accommodation and location are excellent! Listing is accurate and the resort amenities are very enjoyable after a day out exploring the Keys (or just having at least one whole day at the resort, as we did). "
United States
Jenny G.
The price is CA $287
CA $690 total
includes taxes & fees
Mar 17 - Mar 18
Starfish Seas Ocean Pointe 1302 King/Queen 2BA 2BR

Villa in Matecumbe

The Islands of Islamorada
4.0 star property
9.8 out of 10, Exceptional, (72 reviews)
"Beautiful accommodations and location, very clean, many activities available at resort"
United States
Janet
The price is CA $959
CA $1,154 total
includes taxes & fees
Apr 13 - Apr 14
The Islands of Islamorada
9.4 out of 10, Exceptional, (62 reviews)
"Nice location with 5 min walk to ocean view. "
United States
Trevor P.
The price is CA $480
CA $1,044 total
includes taxes & fees
Apr 10 - Apr 11
LICENSED MANAGER - MODERN 2/2 COCONUT PALM VILLA - OCEANFRONT BEACH RESORT!

Vacation Home in Key Largo

Villa hermosa
The price is CA $567
CA $1,240 total
includes taxes & fees
Apr 6 - Apr 7
Villa hermosa
9.8 out of 10, Exceptional, (152 reviews)
"Great stay lovely home "
United States
Yezenia
The price is CA $270
CA $668 total
includes taxes & fees
Mar 23 - Mar 24
3212 Across from Pool * King & Queen/Twin Bunk Bed
6.0 out of 10, (1 review)
The price is CA $447
CA $801 total
includes taxes & fees
Apr 12 - Apr 13
Key Largo 2 BR Condo - Ocean Views, Pool, Beach

Apartment in Tavernier

Dazzling Ocean Pointe -OP-Main
9.0 out of 10, Wonderful, (91 reviews)
"Great place to stay. Fantastic property grounds. Amazing pool and spa area. Beach is mediocre at best but there are plenty of other beaches around to visit close by. All in all beautiful place to vibe. "
United States
Michael H.
The price is CA $275
CA $475 total
includes taxes & fees
Apr 12 - Apr 13
Dazzling Ocean Pointe -OP-Main
10.0 out of 10, Exceptional, (162 reviews)
"Very clean and quiet location. Beds were comfy and all necessities were provided. Would definately recommend!"
United States
Arielle F.
The price is CA $343
CA $714 total
includes taxes & fees
Apr 14 - Apr 15
Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
9.8 out of 10, Exceptional, (173 reviews)
"Loved this place and will stay again if we go back to the Keys. Gated community with golf cart to go to the pier with great community resources, grills and sitting areas. Favorite part was the lagoon in the middle of the community not far from the screened in back porch. Full of fish you can swim with and calm beach area that is clean and nice with shade when you need it. We didn’t want to leave this place. Highly recommend!!"
United States
Chandler G.
The price is CA $829
CA $1,529 total
includes taxes & fees
Mar 18 - Mar 19
NEW! CASA PALMA OCEANSIDE -GOLF CART, 2 KING SUITES, POOL, BEACH, PICKLE, KAYAKS
9.8 out of 10, Exceptional, (68 reviews)
"Great place!"
United States
Jessica S.
The price is CA $603
CA $1,374 total
includes taxes & fees
Mar 17 - Mar 18
Sunrise Escape - Ocean Front Villa - Sleeps 10
10.0 out of 10, Exceptional, (24 reviews)
"We had a great stay, the unit was centrally located and close to everything. The unit was clean, welcoming well equipped with everything we needed for our stay."
United States
Michelle S.
The price is CA $284
CA $687 total
includes taxes & fees
Apr 13 - Apr 14
Ocean View Overlooking Marina Ocean Pointe 5305
9.8 out of 10, Exceptional, (129 reviews)
"Close to main areas of Key Largo, nice and clean in a good area. Owner was very communicative"
United States
Martha B.
The price is CA $754
CA $1,370 total
includes taxes & fees
Mar 19 - Mar 20
Saltwater Lagoon-View Luxury in Key Largo Kayaks, Pools, Boat Slip, & More!
9.6 out of 10, Exceptional, (7 reviews)
"Great area"
United States
Yesenia
The price is CA $268
CA $665 total
includes taxes & fees
Mar 23 - Mar 24
Reel Key Largo Escape Ocean Pointe 5209

Apartment in Tavernier

Coastal Joy 3412 Ocean Pointe
The price is CA $296
CA $688 total
includes taxes & fees
Apr 13 - Apr 14
Coastal Joy 3412 Ocean Pointe
9.8 out of 10, Exceptional, (41 reviews)
"Great space and location! Highly recommend!"
United States
David W.
The price is CA $346
CA $940 total
includes taxes & fees
Mar 19 - Mar 20
Peekaboo View of Atlantic Ocean - Free Kayaks Pickleball
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.
Save an average of 15% on thousands of hotels when you're signed in

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 Oceanfront - Heated Pool - Dock.

How many vacation rentals are there in Islamorada?

With 419 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 Florida Keys Brewing Co. and Bud n' Mary's Dive Center.

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.