Family-friendly holiday rentals in Islamorada

Perfect for our family of 5. Great outdoor area at the house for fishing and relaxing. The layout was great for us because of the separation from the master to the kitchen/living room…our baby could sleep and we didn’t have to worry about making noise and waking up the baby. KCB is in a great central location for exploring the Keys. We were also pleasantly surprised at the quality of restaurant’s nearby. The Cabana Club was crowded and has a small beach. Drinks there were good. I have nothing overly negative to say, other than that I wouldn’t look to stay in KCB or this property if you just want to hang at the pool and beach all day. But it was fine for a few easy afternoons between other activities in the area. We highly recommend and would stay again!

This booking was great for what we needed, thank you to the responsive hosts and pet friendly house that made our vacation that much better.

Our stay in Marathon couldn’t have gone any better! I traveled with my three 20-something sons and their wives/significant others. The layout of Gerardo’s home was perfect for our needs. We had plenty of room, places to enjoy together, and space where everyone could find some peace and quiet. The location was ideal. We were within an easy driving distance of all excursions and restaurants and could even walk to Island Fish Company, which was one of our favorites. Gerardo was extremely responsive. He checked in prior to our arrival and touched base a couple of times to make sure there was nothing we needed. An excellent home I recommend to others with no hesitation!!

Our group of six adults loved our stay at One Particular Harbor! The property was beautiful and spacious! The pictures couldn’t do it justice. Our hosts were very helpful and attentive! We would definitely stay there again.

10 out of 10 stay. Beautiful, serene property where we often felt we had the mangrove and key to ourselves. Several days were spent on a recurring rotation of kayaking, pool, hot tub, repeat. Perfect distance from Key West for adventuring there, but plenty on Cudjoe Key and Big Pine if you don't want to venture to the hustle and bustle. Sincerely hope to return!!

Place was very nice and accurately described

A Perfect Getaway! Our stay at this fabulous Airbnb was nothing short of amazing! The house was beautiful, clean, and offered breathtaking panoramic views of the open water. Waking up to the sunrise over the water was absolutely unforgettable. Brad, our host, was fantastic—super responsible, quick to respond, and incredibly easy to communicate with. He made the entire experience smooth and enjoyable from start to finish. The location was ideal for anyone who loves peace, nature, and especially fishing. We had plenty of opportunities to fish right from the property, which was a huge bonus. Highly recommend this place to anyone looking for a relaxing waterfront escape. We can't wait to come back!.

Our group of 8 stayed Feb 2025. The home is nicely decorated, clean, and Jose supplied a starter set of toiletries for the shower, hand soap, toilet paper, paper towels, dishwashing liquid, dishwasher pods, some coffee pods, and spices for cooking. They supplied large beach towels for the pool, a small cooler, and noodles. The oasis pool and hot tub were awesome. Don’t miss the second pool by the marina that is heated and a hot tub grotto which was perfect in the evenings. 2 pools, 2 hot tubs, you just can’t beat it! This townhome is located near many restaurants and fun places for activities. You enter the home from the first floor but second floor is the main living area with full kitchen, living room, and nice balcony. Two bedrooms are on the third floor so lots of stairs but worth the trip. First floor has a private king bedroom with a pull out couch in the living area and a small kitchen. Laundry room is in a storage area outside next to the front door. We loved our stay and Jose!

We booked this home last minute and now have our go-to vacation spot in Marathon! Alida is a friendly host with great communication. The home is very clean. Beds are very comfortable. Kitchen is well stocked with pots, pans, etc. The kayaks and paddle board made our vacation even more special! The steet is very quiet and peaceful. The setting in the back yard is very private, as is the long dock. We had a 23' rental boat for our stay. The view is amazing and the sunsets are a special treat each evening. I very much appreciated the ample, comfortable seating everywhere - inside and outside of the home. Thank you Alida. We made great family memories here!

Great place and location. Close to lots of restaurants. Pool was really nice! Kitchen was fully stocked and nice that they provide paper towels/toilet paper/dishwasher detergent/etc. to get you started. Had a nice bottle of champagne waiting for us upon arrival as well.

Very clean, smelled fresh as soon as we opened the door. Everything was bright and clean. Excellent for the two of us! The outside table and chairs were very nice. We did not get to use the Kayaks or the paddle boards because we were with family and there was a boat. I do recommend this place because it was so peaceful. The pool was refreshing and even snorkeling in the canal was a treat! I look forward to visiting again and staying longer. Thank you kindly! Laura Gosnell and David Carson, Vero Beach Fl

We really enjoyed our stay with Key Lime sailing club! We especially appreciated the easy access to water activities and created life long memories kayaking in the beautiful surroundings. The hosts are kind, helpful and made our stay more memorable!

Older home with a few issues, nothing major. Maikel was great and always responded to calls and texts. It was overall a great stay and we would come back!!

The house was well equipped with all of the essentials. We had 8 adults and plenty of room. We did have to wash towels a few times, and buy more laundry soap, but the washer and dryer were conveniently located on the main level. The pool was smaller than what the pictures showed, but it perfectly suited our needs. All members of our party viewed the listing before we booked it and none of us realized it was a twin home. However, there is tons of privacy and the only times we noticed we had neighbors was when the shared dock was used. We had to buy a cooler (for poolside and the beach) and beach chairs. There were some pool floaters left behind, from previous guests that we used. The interior of the home is beautiful, with high ceilings and comfortable furniture. This is in a great location - close to grocery stores, restaurants and Sombrero beach! Monica was great to work with!

Pure paradise! This private corner-lot home on the water gave us everything we dreamed of for our Keys getaway. Our boys fished from dawn to dusk while we kicked back, relaxed, and enjoyed the incredible peace, quiet, and space—it truly felt like our home away from home. The location is unbeatable: a quiet, friendly neighborhood that’s close to everything but feels like a private retreat. Inside was spotless, comfortable, and thoughtfully equipped—perfect for cooking, bathing, sleeping, and recharging after long days outdoors. The window A/Cs in the bedrooms were loud but kept things ice cold, and the kitchen ants are just part of life in the Keys. The bait freezer in the garage was perfect for our week of fishing. We loved having use of the 1-car garage—super convenient for tossing in all our beach and fishing gear at the end of the day. There were plenty of towels, extra sheets, and everything we could possibly need in the kitchen and bathrooms. We can’t wait to come back! 5 stars!

The RV lot was well landscaped making the space feel tropical. Access to bath and laundry facility were just a few steps from the lot.

This is our second time staying at Ron and Irma's place and we'll continue to go back! The condo is spacious, clean, modern and in a convenient location. Ron and Irma made sure to include absolutely everything you may need during your stay– down to the pots and pans. My family and I love staying here, and we highly recommend it.

Our stay was great for a family of 5. Vaulted ceilings, CLEAN bathrooms, nice tile, fixtures, plush towels and bath rugs, lots of pool towels, large couch, huge dining table, immaculate stocked kitchen, ice and water dispensers in fridge, short walk to a heated pool, deep canal steps away (under construction) and next to a full service marina. Parking easy, check in seamless. Great for kids lots of space to spread out, multiple porches, quiet, central location. Brian was easy to work with. Could improve: Master bath barn door (not shown in listing) did not open/close easily. The toilet is awkwardly close to the bed (you can reach the bed from the toilet). Also, if you can get the barn door shut, the gaps btwn the door are so big it doesn’t offer any privacy. We used the other 2 toilets in the house instead of the one in the master. A regular door there would be a big improvement. Beds were average, sheets were low quality, window blinds, pots and pans have seen better days.

Easy to find, easy to contact and reach glenn, and he was very helpful, would definitely stay here again.

Jose was an amazing host! His son was super helpful with local recommendations, also. Very easy and quick to reply. The condo was super clean (I'm very picky) and had everything that we needed to be comfortable and "at home." They even had a book on what to do in the Florida Keys- we did many activities listed in the book. The condo location was close to everything we did- snorkeling, deep sea fishing, restaurants etc. The lagoon was SO AWESOME! The fish would swim around the kids! The parrot fish were beautiful. The kids had so much fun! We also watched the iguanas climbing the trees. One would sleep on the top of the palm tree outside of our 5th floor balcony! The view of the sunsets are phenomenal. We would absolutely stay here again!

Very nice house. Very clean. Only downside is the noise from the road behind the house. You don’t pay any attention to it until you try and sleep. The place is very beautiful. Swimming pool was very nice. We used the kayaks and bikes. It was a quiet community. What we were looking for and it was gated. We would definitely stay there in the future.

Great condo in a perfect location to access the best of Key Largo. The condo is in a nice complex, with a great pool, mini beach, and dock area. The unit was well stocked with beach & bath towels, all kitchen appliances, washer dryer with detergent & dryer sheets, spare cooler, charcoal & lighter fluid for the grill. The bedrooms were super comfy. I highly recommend staying here!

great location for exploring all of the different keys. beautiful quiet neighborhood. cabana beach club was a great perk. 5 minute walk, weloved the pool and the lunch menu. Havana Jack's was delicious and easy to walk to. The out side of this place was much nicer than it looks in the pictures. the inside was simple and clean. having 1 bathroom was a bit challenging with a family of 4 but I knew that going in. overall my favorite part was sitting outside and looking at the water and feeling the incredible breeze

Dean’s condo was exactly as pictured. The complex was beautiful and very well maintained. We loved having a few restaurants to walk to as well. Can’t wait to come back.