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Holiday houses in Islamorada

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Popular amenities for Islamorada holiday rentals

Other great holiday rentals in Islamorada

Top Guest favourite
Home in Marathon
5 out of 5 average rating, 18 reviews

Waterfront with Boat Lift/Kayaks and Hot Tub

JohnRating, 5 stars2 weeks ago
The place was amazing!! plenty of room for our family of 5. All of the fishing equipment was awesome!! From the rods and tackle, to the deep freezer with bait, the extras made the whole trip more enjoyable. Loved the house. It was perfect!!! Will definately be back in the future!! 10 out of 10 would recommend!!
Superhost
Apartment in Islamorada
5 out of 5 average rating, 3 reviews

Ocean View Duplex Penthouse | Pool | Vista Two

AnneRating, 5 stars3 months ago
Beautiful, very clean property with a fantastic location. Excellent proximity to snorkeling, restaurants and other local attractions. Short stroll to excellent walking path that takes you along route 1 with amazing morning views of the beautiful water. Great views all around, in fact. Plenty of soft, plush towels and similarly luxurious bed linens. We had a wonderful family vacation staying at this property.
Top Guest favourite
Apartment in Islamorada
4.93 out of 5 average rating, 29 reviews

The HMH House

KimberlyRating, 5 stars4 weeks ago
I had a lovely stay with my college daughter in the Keys. The place was just what we wanted. The decor was so beautiful and the grounds/pool area were so pretty. We were so sad to leave. Will definitely return. Heather Marie was amazing and such a wonderfully generous human. I can’t recommend this property enough.
Guest favourite
Apartment in Tavernier
5 out of 5 average rating, 49 reviews

When Paradise is Key: Tropical Oceanfront Condo

JoelRating, 5 stars4 days ago
We had a wonderful time staying at Michael’s place. It was exactly as described, clean, modern, and very comfortable. The attention to detail in the decor made it feel like a true home away from home. The location was perfect, close to everything we needed, yet quiet enough for a relaxing stay. Michael was a fantastic host: communicative, helpful, and respectful of our privacy. We especially appreciated the well-stocked kitchen, fast Wi-Fi, and cozy balcony area for morning coffee. We would absolutely stay here again and highly recommend it to anyone looking for a hassle-free and enjoyable stay. Thanks again, Michael!
Guest favourite
Apartment in Islamorada
4.9 out of 5 average rating, 10 reviews

Bungalows King Bed

CourtneyRating, 5 stars3 weeks ago
I loved it so much I booked another stay in October. Great location. Great staff. Quiet and peaceful. Walking distance to great restaurants. enough kitchen space to eat in. I was very happy with my stay.
Superhost
Apartment in Tavernier
4.9 out of 5 average rating, 78 reviews

Ocean Pointe 2309 with Ocean Views

EricaRating, 5 stars1 day ago
This condo was exceptionally clean and well-maintained. It had all the amenities we needed for a comfortable stay during our trip to the Keys. The location—about two hours from Key West—was ideal for a convenient day trip. I highly recommend her property to anyone visiting the area.
Top Guest favourite
Condo in Tavernier
5 out of 5 average rating, 54 reviews

Tequila Sunrise

AaronRating, 5 stars5 days ago
Exactly what we were looking for. Clean, cozy and great location with an amazing view of the ocean and sunset. Pool area with hot tub was clean and a nice bonus, as well as the small beach and pier. Highly recommend and would definitely book again
Cottage in Islamorada
4.79 out of 5 average rating, 156 reviews

1 BD PRIVATE HOUSEBOAT/ COTTAGE TARPON

T LRating, 5 stars4 months ago
Toni was very nice. She went out of her way to make sure we were satisfied with everything. The bed was comfortable and we got a great night's sleep there on the water. Watching the fish jump and pelicans dive as we sat on the front deck was very relaxing.

Quick stats about holiday rentals in Islamorada

  • Total rentals

    880 properties

  • Nightly prices starting at

    $67 NZD before taxes and fees

  • Total number of reviews

    7.6K reviews

  • Family-friendly rentals

    610 properties are a good fit for families

  • Pet-friendly rentals

    420 properties allow pets

  • Rentals with a pool

    610 properties have a pool

Destinations to explore

  1. Airbnb
  2. United States
  3. Florida
  4. Monroe County
  5. Islamorada