Family-friendly holiday rentals in Stock Island

The place was very peaceful. The courtyard was like a bird sanctuary with doves singing in the morning. It was safe and secure and very lush landscaping!!

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!

Plenty of room for all the family and their families. We enjoyed all the backyard amenities with pool, kyacks, boat dockage and fish cleaning station. There was sufficient seating for everyone and a great area to hangout. The only things we struggled with was TVs didn’t work properly in some of the rooms, no washcloths or kitchen towels available. With that being said, we will definitely consider renting Ryan’s place again in the future!

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!!

We were next to the airport but didn't hear the planes. It was far away from Key West tourist attractions and restaurants. It was nice to come back to our place for peace and quiet. It was nicely decorated and felt like a beach get-away.

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!!

Our stay was great. We had detailed instructions, the unit itself was decorated nicely, and the amenities within the building were great (pool and spa). Also the private beach area and walkability to food, snacks, restaurants was great!

Very nice place to stay without breaking the bank. Lyft and Uber are always available to get you to where you want to go or rent a golf cart. Very responsive host, we will definitely be back.

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.

The townhouse was in a beautiful location and was very clean. The kitchen was supplied with spices and some basic needs until you went grocery shopping. We had a very nice time and could sit on the back porch and look at the awesome view every minute of the day! There was a lovely pool on the property and anything we wanted to do was conveniently located to the property. We would love to 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!

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.

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.

Perfect getaway for a couple, very quaint cottages. Bonus is the taco food truck on property as well as the covered bar area. Would definitely stay again!

The Grouper house was fabulous. I stayed there with my wife and kids for a week. Everything about this place was top notch. From booking to check in and check out. Her staff is nothing short of superb. Sean makes sure every need or question is answered promptly. The best place I have ever stayed. Highly recommend.

I stayed at the Truman Annex last year for the boat races and loved the location. I decided to rent from Wally this year due to his condo was more open and also had a 2nd bath! He was very responsive when I texted him, the house was very clean and everything was perfect, I highly recommend!

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.

This house was a perfect spot for my partner and I and Cooper our pup. swam in the pool, sat in jacuzzi, paddle boarded ,kayaked, road the bikes, ect. we brought our boat down but unfortunately had a few issues with it so wasn't able to go out fishing as much as we'd liked. but there was plenty to do at and around this beautiful place. would definitely come back in the future:))

Fabulous vacation in Key West with family. Location was convenient, quiet, and beautiful. Although only a block from Duval, the space was far from chaotic. Beautiful pool and surrounding area. The house could not have been more clean, and instructions were extremely easy to follow. Would recommend this space to all!

This home was just what my family needed for our vacation! We all loved relaxing in the outdoor living room surrounded by greenery. We also enjoyed swimming in the pool and kayaking through the canals and Boot Key. We made most of our meals due to dietary restrictions, and the kitchen here was adequate. The location in Marathon is excellent! It was just a 5-minute walk to Sombrero Beach, so we never had to worry about parking. We could easily drive to all the activities we wanted to do in the area, too.

Exceeded our expectations!!! Naomi was amazing and so helpful. I wish we had more time to spend at her beautiful property.

Our stay was amazing. The staff that runs the condo very friendly always cleaning all the common areas. Peter kept the beach areas clean every morning. Very quiet we rented kayaks and paddle that out to the sandbar every day. It was beautiful.

We were extremely pleased with this amazing home. It was beautiful, soundproof, so clean and had extra towels, pool Towels, everything we needed but didn’t want to pack and take with us. We highly recommend Pineapple, and we will see you next April. So thrilled to have found an amazing host!! Thank you so much. Also, anytime we had a question, or we couldn’t figure something out, Chris the caretaker was there in MINUTES. Thank you again for helping us have a memorable vacation!!