
Family-friendly vacation rentals in Big Pine Key
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Big Pine Key
Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.
Vacation rentals for every style
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Popular amenities for Big Pine Key family-friendly rentals
Family-friendly home rentals with a hot tub

Paradise - Pool, Hot tub, Mini Golf, Dockage, Fish
Although the place wasn’t ready when we arrived, Ryan was a great communicator! He addressed every issue we had (which were NOT within his control) and responded in a timely manner. He offered a fair solution and allowed us to sit back, relax and enjoy paradise! I’d highly recommend and hope to be back sometime soon!

4BR 3B, Heated Pool & Spa, 60' Dock
Amazing house. Beautiful surroundings. Plenty of room for 3 families and kids. Everything we needed.

Sweet Retreat! 4 bedroom 2.5 Baths Sombrero Beach
Beautiful home that comfortably held our 6 person family of adults. Absolutely loved the pool, spa, and outdoor seating. Really nice kitchen and bathrooms. We used Marathon as home base and drove to Key Largo, Key West, etc. Always nice to return to the house and pool to relax!

Affordable Beachfront Luxury Condo Sleeps 6
Everything was perfect for our stay at Airbnb, the pool felt amazing, the views were stunning, and the Uber drivers were incredibly fast. Even the locals agree that this is the best place to stay in Key West, and I couldn't agree more - I'll definitely be back. Our host, Traci, was absolutely top-notch!

EYW Getaway
Edward's place was great! we really enjoyed the home like vibe. It had everything we needed during the stay. The sunset view from the balcony was beautiful.

Palm Breezes! Room for Everyone on the Ocean.
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!!

Plunge Pool Villa on Blue Water Lagoon
Loved this little place to get away for a relaxing weekend, very cozy and comfortable. Looking forward to coming back soon.

Casablanca Too ~Chicly updated home with hot tub
The home is lovely. Updated kitchen, comfortable bed, outdoor grill and private parking spot were all pluses! The communication with the host could not have been any better. I look forward to returning one day soon!
Family- and pet-friendly home rentals

Sunset Catch Gulf Front, Pool, Dock, Kayaks, Fish
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!

Waterfront luxury Villa (14) with sunset views and boat slip
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.

Manatee Quay-2 Canal waterfront,access BEACH club
Our stay at this home was absolutely perfect! The location couldn’t have been better—peaceful, relaxing, and right on the water. We spent so much time unwinding on the dock, soaking in the beautiful views and enjoying the gentle ocean breeze. The Marathon area was a fantastic place to explore, offering everything we needed for an unforgettable getaway. We loved being close to state parks for hiking and wildlife spotting, as well as having access to amazing restaurants serving fresh seafood. Bike rentals were nearby, making it easy to explore the area at a leisurely pace. If you’re looking for the perfect blend of relaxation and adventure, this is the place to be!

Cottage w/ Private Yard, Free Kayaks, Boats, Etc
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!

Fish Camp, Fun, Keysy Oasis, with Tiki, pool, dock
Fish Camp was spotless and the owners and property management were very communicative leading up to our trip and once we arrived. No major issues - and if we reached out they responded right away. Beach chairs would have been a great addition for our stay.

Pier Pressure~ Waterfront Pool Home, 100' Dock
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.

New Paradise On Sombrero Beach
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.

Bring Your Own RV! Our Lot Your RV B6 No Tents
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.
Family-friendly home rentals with a pool

Waterfront, dock, easy ocean access, heated pool!
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:))

Angler's Reef Oceanfront
My friend and I stayed at this lovely house in a well maintained community. The house is clean and very nice. The owner was very responsive. We had no issues during our week stay. The community pool was fantastic. We grilled a few nights and took advantage of the great restaurants within 10 minutes away. Highly recommend unit and location.

Villa Casa Cayo
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.

Your island home away from home!
Beautiful place. Nice neighborhood. Would stay again. 10/10 recommend.

Vida De Aqua - Water Life!
We had a wonderful stay for our annual family fishing trip. Lots of privacy with the corner lot which is a premium in Marathon. Great location and close to everything you need for your trip.

Kawama Suntastic @ Key Largo
My family and I had an absolutely wonderful stay. We enjoyed swimming and powder boarding in the lagoon, feeding the fish, fishing off the point, relaxing poolside, and enjoying our time in Key Largo. Check-in was super easy and the owner, Cindy, was an absolute delight. Very smooth and easy, five stars, highly recommend, especially for children or anyone looking for a relaxing time.

Beautiful open plan remodeled home in Key Colony
Wonderful welcoming beautiful place to stay! Close to excellent restaurants and several beaches. Has outstanding large screened in porch on the canal with comfortable seating. Access to club house with large sparkling pool and beach 2 min. drive. Excellent drinks. Highly recommend!!!

Keys Elegance. Pool, Hot Tub, Dock Summer Specials
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.
Quick stats about vacation rentals that are family-friendly in Big Pine Key
Total rentals
190 properties
Nightly prices starting at
$97 CAD before taxes and fees
Total number of reviews
2.9K reviews
Pet-friendly rentals
100 properties allow pets
Rentals with a pool
80 properties have a pool
Rentals with dedicated workspaces
80 properties have a dedicated workspace
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