Holiday Rentals in Islamorada

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Our top choices for Islamorada holiday rentals

Houseboat in Islamorada

Treasure Harbor
3.0 star property
9.0 out of 10, Wonderful, (123 reviews)
"Great spot! Will be back someday hopefully. "
Canada
Diane
Treasure Harbor

Aparthotel in Matecumbe

Breezy Palms Resort
2.5 star property
8.8 out of 10, Excellent, (606 reviews)
"Property was nice and easy to navigate, ocean view room was extra nice to have!"
United States
Lisa
The price is €189
includes taxes & fees
14 Jan - 15 Jan
Breezy Palms Resort

Villa in Matecumbe

The Islands of Islamorada
4.0 star property
9.8 out of 10, Exceptional, (70 reviews)
"Amazing stay, can’t wait to stay there again!"
United States
Anonymous traveller
The price is €636
includes taxes & fees
19 Jan - 20 Jan
The Islands of Islamorada
9.8 out of 10, Exceptional, (43 reviews)
"Would stay there again."
Canada
jamie g.
The price is €428
includes taxes & fees
28 Jan - 29 Jan
Boho Style Florida Keys Condo Ocean Views

Houseboat in Tavernier

Island Sanctuary Islamorada
9.8 out of 10, Exceptional, (13 reviews)
"It exceeded our expectations, and we are so glad we found this location!"
United States
Jenn H.
Island Sanctuary Islamorada
2.5 star property
10.0 out of 10, Exceptional, (1 review)
"Beautiful & perfect place for a getaway. Really enjoyed our stay. Highly recommend."
United States
Michelle
The price is €420
includes taxes & fees
1 Feb - 2 Feb
Aqua Vista Ocean Pointe 3307
9.8 out of 10, Exceptional, (210 reviews)
"Absolutely wonderful property in every way!"
United States
Christopher K.
The price is €444
includes taxes & fees
16 Jan - 17 Jan
Fla Keys Luxury Houseboat, Prime Location-Steps to Fun, Food & Water Adventures
10.0 out of 10, Exceptional, (33 reviews)
"Very clean, lots of things to do for the kids on property - large pool and hot tub, tennis and pickle ball courts, and a small beach. "
United States
Robert F.
The price is €587
includes taxes & fees
13 Jan - 14 Jan
Coastal comfort in Ocean Pointe Suites.
2.0 star property
10.0 out of 10, Exceptional, (46 reviews)
"Good location. Lagoon and pool right outside door. "
United States
Debra C.
The price is €517
includes taxes & fees
13 Jan - 14 Jan
NEW ! Lagoon-front townhouse with Marina! Day Dreams Key Largo.
10.0 out of 10, Exceptional, (1 review)
"The property was just as pictured on the site! We loved the view from the balconies (yes, two!!!). The host was superior in supplying our basic needs upon arrival. More importantly, she was extremely responsive to our questions during our stay (usually responding within a few minutes--even on Christmas day!!). The property is conveniently located in the keys so it's not too far to Miami or Key West. We absolutely loved our stay! If we come back to the Keys, we will definitely stay here again!!!"
United States
Mark W.
Top Floor w Amazing Ocean Views!! Resort Style Pool, Beach, Marina, & Cafe!
10.0 out of 10, Exceptional, (2 reviews)
"Beautifully high-end decorated & furnished like brand new! Very clean and appointed with everything one could want for a perfect stay. First floor convenience (building elevated on piers) but no water view Would definitely return! "
United States
Peter A. Z.
Island Time at Ocean Pointe Luxe 2 King Spa BR/BA, 2 Balcony
2.0 star property
10.0 out of 10, Exceptional, (1 review)
"A good place to relax."
United States
gildas m.
2BR Condo w/ Ocean Views, Private Beach & Pool
10.0 out of 10, Exceptional, (157 reviews)
"The property was excellent."
United States
June M.
The price is €391
includes taxes & fees
19 Jan - 20 Jan
Sea View Farm Style Ocean front Condo Views
2.0 star property
10.0 out of 10, Exceptional, (3 reviews)
"Great place! Condo was clean l and was as described. Property and pool area was fun and very clean."
United States
Kevin W.
Ocean View Gem Ocean Pointe 3406 2BA/2BR King/Queen
10.0 out of 10, Exceptional, (4 reviews)
"The condo was very clean, comfortable and had everything we needed. We appreciated the close location to the pool. "
United States
Erica T.
The price is €418
includes taxes & fees
2 Feb - 3 Feb
Sunrise Oasis - Top Floor 2 BR 2 BA Condo 2411
10.0 out of 10, Exceptional, (1 review)
"The amenities and location were nice for being close to Key Largo. There is a small park that faces the Atlantic side which is a 1 minute walk from the apartment. "
United States
Kathleen A.
The price is €510
includes taxes & fees
14 Jan - 15 Jan
Private 3-bedroom brand new apartment in Tavernier, Key Largo
10.0 out of 10, Exceptional, (108 reviews)
"Fantastic place to stay! Very clean and great hosts. Will stay again. "
United States
Les
Serenity In The Sun Condo Fabulous Ocean View
9.8 out of 10, Exceptional, (170 reviews)
"Everything was clean and in good condition. The owner responded right away to any questions. Golf Cart is a plus! "
United States
Anonymous traveller
The price is €1,009
includes taxes & fees
29 Jan - 30 Jan
NEW! CASA PALMA OCEANSIDE -GOLF CART, 2 KING SUITES, POOL, BEACH, PICKLE, KAYAKS

Apartment in Tavernier

Boho Chic Ocean Pointe 3214
10.0 out of 10, Exceptional, (12 reviews)
"It was clean, well organized and communication was great. Had a good time."
United States
Shirl
The price is €421
includes taxes & fees
27 Jan - 28 Jan
Boho Chic Ocean Pointe 3214
Spectacular Ocean-Marina Views - 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.
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Top Islamorada Hotel Reviews

Find out more about Islamorada

Everything you need to know about Islamorada holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Islamorada holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Islamorada holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Islamorada holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Islamorada holiday rentals we have selected for you start as low as €189 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Islamorada rentals

At Expedia, we put the best Islamorada holiday 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 holiday.

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 holiday rental in Islamorada?

Yes, there are holiday rentals close to the most popular sights in Islamorada, or you can select a more secluded option if you're looking for 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 holiday rentals that Islamorada has to offer?

Bungalow #4 - 2 Bed/1 Bath & Pool in Islamorada: This highly rated holiday home rental in Islamorada offers an outdoor pool, a BBQ 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 Oceanfront 4-BR w/ private 31' Boat Slip Included, Pool & Beach, gourmet kitchen and Bungalow #3 - 2 Bed/1 Bath & Pool in Islamorada.

How many holiday rentals are there in Islamorada?

With 486 Expedia holiday rentals, you're guaranteed to find just the right place for your Islamorada stay.

What can I see and do in Islamorada?

Enjoy the outdoors at Everglades National Park and Founders Park, or simply take in cultural attractions like History of Diving Museum and MoradaWay Arts & Cultural District. Other places in town to visit include Florida Keys Brewing Co. and Bud n' Mary's Dive Center.

What’s a holiday rental in Islamorada like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Islamorada. Holiday rentals feature extras like laundry facilities and kitchens so your stay will be comfortable. If you're concerned about a sanitised environment, holiday rentals can offer a sense of privacy away from shared hotel lifts and bustling concierge desks while still allowing you the experience of travel. You'll also get more space in a holiday rental than in a hotel, which makes a holiday rental a great option for family trips.