Smoking-friendly holiday rentals in Key West

Our unforgettable stay at this oceanside Airbnb resort on Big Pine Key was nothing short of extraordinary!! Even before the moment we arrived, the staff’s warmth and dedication made us feel like family. Every detail, from the included bicycles and complimentary kayaks to the Key Deer roaming freely near the resort’s lush grounds made it so captivating. With breathtaking—pristine beaches, stunning ocean views, and beautifully designed accommodations that blend luxury with coastal charm. The Staff truly went above and beyond to accommodate our needs. Due to unforeseen errors prior to arriving, I had some hurtles to overcome which they did and amazing job assisting with. Their attentiveness and genuine care elevated our experience to another level. The resort’s amenities, including the magnificent facilities with stunning architecture and private beach access were impeccable, and the serene atmosphere made it impossible to leave. Five stars aren't enough for this slice of paradise!

My family and I enjoyed Jennifer's place. We spent most of our time fishing on the canal in the back yard and traveling to local beaches and little towns. Jennifer's place has plenty of room, closet space, drawer space (which I love), comfortable beds and several extra blankets if needed. I had several questions and Jennifer immediately responded to all of them. I would recommend this rental for even large families as we had 8 people and were all very comfortable. Thank you for letting us enjoy your home!

Our stay was fantastic, great location and view. The house is set up perfectly if you have several people staying.

hard to find a house like this in marathon. excellent value for the most exclusive area. very comfortable and with everything you need to spend unforgettable days with your family

We had 6 people and we’re not crammed at all!

We stayed at Tree Top Paradise for 3 nights during a quick trip to the keys, and this home was perfect for our family of 5. My wife and I were in the master bedroom, my old daughter and her boyfriend were in the 2nd bedroom, and my younger daughter used the pull out couch in the living room. We all had plenty of room, which was good, since the weather didn't cooperate during our stay (washout one day with driving rain until mid evening). Even during the rain, we were able to hang out on the covered screened in porch, which was nice. The unit was furnished well, having everything needed. Was clean enough that my wife didn't feel the need to reclean the place like she will do at a lot of other places we rent, so that was good. Only minor issue was a plugged shower drain, but was able to unplug it with a plunger, so didn't need a maintenance call. Also has bikes (bit older) and some beach equipment on site. Overall, it was great, and we'd definitely rent again.

Great location on a deep water canal. Bathrooms and bedrooms were super clean. Linens very soft and clean, comfy pillows and mattress. I really loved the upstairs porch. Beautiful spot to have your morning coffee. Lots of restaurants within 10 min drive. Michael was super helpful and kind. Would totally stay again!

The house is definitely dated and had a bit of a musty smell when we walked in. However, you cannot beat the view. The pool area was beautiful and the water all around it just made it perfect. There were a few things that didn't work and the internet was spotty, but that only really matter at night when we wanted to relax. It is a top contender (once we know how many bedrooms we need) for our trip next year!

Stayed with the Family for Christmas Location of house is convenient and easy to access. The outdoor area is great for relaxing evening. Saw a family of Manatees swimming in the canal. Despite a few small issues during our stay, in which the Host was quick to communicate. We had a great time

Great stay, would highly recommend, home was clean and quiet. Can’t wait to come back to duck key so I can book again.

Property was exactly as described. Beach, pool and outdoor areas are beautiful and well maintained. Never overcrowded. Apartment was clean, well maintained and as described. Resort staff are pleasant and always helpful. Kara is an awesome host and is extremely knowledgeable and helpful. We had a fabulous vacation and would definitely stay here again.

This location is the jewel of the Keys. Private, safe and with an incredible view of the ocean and sunrise. I’ve stayed many times in the area and this is absolutely the best. Owner is extremely helpful and available for any questions. Condo has a well stocked kitchen for cooking with great restaurants nearby. Big, fluffy oversized towels are provided. Being on the second floor near the stairs made that the easiest route in and out. Great group of people we met at the pool, many returning every year for extended stays. Just a wonderful place and hoping to return again next year. Thank you so much, Jeanette!

Had a great time! Needed a place to stay for a week in the same complex as family, and this one came up. No mess, no fuss!

This condo is lovely. It looked like the pictures. Our family of 4 found the location very walkable. We loved the proximity to Smather's beach and we walked to dinner in the Duval Street area and to drop-in yoga. The condo was clean and comfortable. We enjoyed the wide balcony. The grounds were well-maintained and the pool area very nice. For those that might not want to walk everywhere, we found Uber to be reliable and quick.