Islamorada Holiday Rentals

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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, (144 reviews)
"Staff was great, rooms clean, views excellent"
United States
Diane
The price is AU$494
includes taxes & fees
23 Mar - 24 Mar
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 AU$366
includes taxes & fees
24 Mar - 25 Mar
Breezy Palms Resort
9.8 out of 10, Exceptional, (235 reviews)
"Great place to stay"
United States
Llonda B.
The price is AU$827
includes taxes & fees
7 Apr - 8 Apr
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 AU$671
includes taxes & fees
13 Apr - 14 Apr
Ocean view condo with balcony/marina view

Holiday Home in Key Largo

Charming Home in Key Largo
9.8 out of 10, Exceptional, (33 reviews)
"Clean, updated, had everything we could have asked for. "
United States
Debra D.
The price is AU$604
includes taxes & fees
29 Mar - 30 Mar
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 AU$788
includes taxes & fees
27 Mar - 28 Mar
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 AU$1,205
includes taxes & fees
13 Apr - 14 Apr
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 AU$1,073
includes taxes & fees
10 Apr - 11 Apr
LICENSED MANAGER - MODERN 2/2 COCONUT PALM VILLA - OCEANFRONT BEACH RESORT!

Holiday Home in Key Largo

Villa hermosa
The price is AU$1,264
includes taxes & fees
6 Apr - 7 Apr
Villa hermosa
9.8 out of 10, Exceptional, (152 reviews)
"Great stay lovely home "
United States
Yezenia
The price is AU$685
includes taxes & fees
23 Mar - 24 Mar
3212 Across from Pool * King & Queen/Twin Bunk Bed
The price is AU$818
includes taxes & fees
12 Apr - 13 Apr
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 AU$489
includes taxes & fees
12 Apr - 13 Apr
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 AU$729
includes taxes & fees
14 Apr - 15 Apr
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 AU$1,567
includes taxes & fees
18 Mar - 19 Mar
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 AU$1,404
includes taxes & fees
17 Mar - 18 Mar
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 AU$701
includes taxes & fees
13 Apr - 14 Apr
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 AU$1,426
includes taxes & fees
19 Mar - 20 Mar
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 AU$682
includes taxes & fees
23 Mar - 24 Mar
Reel Key Largo Escape Ocean Pointe 5209

Apartment in Tavernier

Coastal Joy 3412 Ocean Pointe
The price is AU$726
includes taxes & fees
13 Apr - 14 Apr
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 AU$992
includes taxes & fees
19 Mar - 20 Mar
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.
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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, 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 favourite 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 depend 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 AU$366 per night. Entering your travel dates in the search wizard might find you 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 in Islamorada close to MoradaWay Arts & Cultural District, 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 Private Oceanfront: Heated Pool, Paddleboards & Kayaks - 180 degree ocean views and Next availability from May 18th, 2024 - The Last Resort, Islamorada - MM76.7.

How many holiday rentals are there in Islamorada?

With 419 Expedia holiday rentals, you're guaranteed 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 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.