Family-friendly vacation rentals in Big Pine Key

The Cigar House is great - we enjoyed the easy walkable access to all the amenities in the neighborhood, including bars, restaurants and the Zach Taylor park. The location is really the key here. The grounds are beautiful and the pool/hot tub were nice features. Would definitely stay again.

This was our first time in Key West. We wanted to stay a little tucked away from the downtown bustle. The complex is beautiful with great amenities. And it’s close enough to shopping, restaurants and bars! We definitely plan on booking the same place in the future!!

We had a great time. Pool and spa was great. Caught fish of the dock great spot for the boat and easy access to the ocean!

Great space in the condo, love the pool and amenities area. All simple and easy. The parking was great. Felt really safe. Wonderful to be able to walk toSmathers Beach.

Excellent condo, with everything we needed for our stay. Recommended, beautiful sunset.

We had a great time at this resort during spring break. The listing is as described with helpful suggestions for activities and restaurants. There was always music playing at the pool, contributing to a festive atmosphere. The rooms were clean and well stocked. Largo was a communicative and helpful host.

This place was a great get away. Perfect location between key west and marathon. Very quiet and private. Plenty of space

My daughters and I came from 3 different locales to spend a few days together at Henry's condo. We were very comfortable. The condo is stocked with kitchen utensils, beach towels and chairs, tvs, and a sound system. It was a bit chilly for the pool, but we enjoyed the community's hot tub and landscaped community area. Smathers Beach is a short walk away. Higgs Beach is also walkable and has plenty of parking. I wanted to try the snorkeling trail at Higgs, but it was a bit chilly for me. Still, February in Key West was a welcome relief from the 20 degree weather and snow I left behind! There was a lot of paperwork for an Airbnb ahead of arrival, but everything went great. Henry was always available, responsive, and helpful. We had a terrific reunion and enjoyed Key West.

Highly recommend this location and townhome. Everything was really clean and the kitchen was well stocked. Our children really enjoyed the huge pool and the area attractions. Our favorite spots to send time were Sombrero Beach and Sandspur Beach at Bahia Honda State Park. We rented a boat for a few days and went out to the Sombrero Reef and the sandbar. So much fun! We are definitely coming back to stay at this home again.

We rented Ryan’s home during the week of our wedding in Key West — much more reasonably priced than KW, and only about an hour away. Home is clean, modern, well appointed. Heated pool and hot tub were a big hit with our family, especially kids (worth the extra charge). The pool was dirty when we arrived so when Ryan saw pics he deemed it unacceptable and sent a cleaner out to address it right away — he had a delicious key lime pie delivered for the inconvenience, which was a sweet gesture. It was good to have 2 wings to separate the bedrooms (main plus queen both with private baths on one end). We had 10 people in the home (including 4 kids) and had ample space. Helpful to have chairs and cooler for beach (umbrella didn’t hold up to windy day) — Sombrero beach while crowded was nice. Lighting outside to enjoy outdoors at night could be better, but awning to shade the chairs from sun during day is a great feature. Bring a Bluetooth speaker for music. We’d come back! Thanks, Ryan!

We had an amazing time at this property. The location was couldn't get any better. We brought our boat and property was perfect for that. We are already starting to plan for next year!

We had a lovely stay at your home. The outdoor area was fabulous. We really enjoyed the pool, ladder ball and dock. We were even visited by manatees. We will be back!

We had a great time, and the place was perfect for what we were looking for. The dock had room for my 25' center console and my two sons-in-laws smaller inshore boat and flats boat. Plus being able to keep the trailers on property was huge for us. As far as the house, it was very nice inside and the layout worked out nice for the 8 of us. The pool was perfect and was positioned in such a way which allowed direct sunlight through the whole day for most of the pool and had some shade on one side for those who wanted to get out of the sun for a while (at least during this time of year). It had two paddle boards and two kayaks which we used every day. The kitchen had everything we need.

This place had everything we needed for a relaxing family vacation prior to the crazy Holiday season. we only had 6 people but it would easily accommodate more. Monica was responsive to any questions or concerns. The location was perfect. Easy access to sombrero Beach and Marathon amenities: bars, restaurants, and activities. we were able to experience a turtle release on Sombrero Beach from The Turtle Hospital. Highly recommend renting from Monica again and on Marathon Beach.

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.

Great spot in the resort property . Courtyard outback was tranquil… One young buck who was cleaning his boat on Sat had his music waaaay to loud but once he finished it was quiet again. Bed comfortable, kitchen well stocked. We stayed 2 days on our way down to Key West to enjoy Marathon and Turtle hospital. It was nice also that she allowed less than 3 day rentals :)

Our family of 5 loved our time in Islamorada. The community was beautiful and quiet. It was definitely mostly retired couples but everyone was friendly with our young kids. The condo was bigger than the pictures made it seem- we had more than enough space. Everything was clean and we had everything we needed.

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:))

We had a fantastic stay here during our week in Islamorada. The house was incredibly clean, uncluttered, and had a nice feel. The road noise was pretty much constant, which we were prepared for ahead of time based on other reviews. But noise makers were provided and helped a bit. There were full sized soaps in the kitchen/bathrooms. There were plenty of cleaning supplies in the kitchen including garbage bags, Clorox wipes, and dishwasher detergent. Beach/pool towels were also provided. All of these amenities make it easier when traveling by air. The property had paddle boards and kayaks for use on a first come first serve basis. All 5 of us, my hubby, our three girls ages 13, 19, and 21 had a fantastic time paddling around nearby. Watching the sunset was particularly lovely on the water. There were some fantastic restaurants nearby that were walkable and within a 5-10 minute drive. If we were to come back to the area, we would definitely consider staying here again. Thank you!!

We came for our second stay at Judy’s lovely house. It’s very clean and very comfortable and in a great location. The tiki hut has very comfortable chairs and is a great place to unwind with a drink in the evening. Highly recommended!!

Beautiful view and clean home. Watch gorgeous sunrises right from the screened in porch or out on the dock. Great local restaurants close. We highly recommend The No Name Pub (amazing pizza, and make sure you bring a dollar for their wall). The Bent Prop was another favorite and was only about half a mile away. Breakfast recommendation is to go to Key West to Blue Heaven (try the banana bread)!

Rolando was an excellent host! We thoroughly enjoyed our time at his place. The location was exactly what we were looking for as it was central in the keys and close to everything. We did run into a problem while there, but Rolando was extremely responsive and helpful and had the issue solved literally the very next day. All in all, it was an excellent place to stay.

Beautiful place, exactly as pictured, for our family of six. We LOVED the pool and spa! The porch space was well used with lovely furniture overlooking the pool. Great location for restaurants and activities. The landscaping and grounds are beautifully maintained. Very peaceful and private during our stay.

This house was absolutely amazing! Our family had the best week here. The outside area was so nice and lots of room. We all enjoyed the pool. I loved to sit on the swing every morning and evening. The house was perfect, had everything we needed for our family of 6. It was walking distance to the cabana club that we very much enjoyed also. Lots of food options within a 15 min drive. We would absolutely love to come back and stay.