Vacation rentals in Big Pine Key

Love the food truck on the property, nice area

This place was great, much better then we expected as there weren't really many photos to reference off of. Joni is very great at responding to you, she even let us check in early. We were pleasantly surprised with the property, not just the home but the actual land because it sits on a good acre+. Plenty of room to walk around and explore and just watch the wildlife. inside the home was absolutely beautiful, well kept and clean. TV worked great as we got ready to head down to KW, bathrooms were clean and well stocked. Rooms were nice and the loft was a nice touch, my wife and I slept in that bed and it was comfy. we came with 2 other couples and they said their rooms were great as well. The walk out patio was amazing to watch the sunrise/sunset and had even a large connect 4 set out there. there was a washer/dryer on site and a large deep freezer just in case you need those. we weren't there much, just to get ready and to sleep but it sleep 6 people well. The home is about 19 miles from downtown Key West and felt close enough that we had brunch down there and were able to come back and showerand clean up all within an hr or 2. it is off the main US 1 so taking the turn into the property is kinda hidden but very cool to go thru, road is bumpy so ride slow as it's gravel/rock road. we will definitely stay again in the future

We spent a week here and loved it, it was the perfect size for me and my husband to celebrate our anniversary. It was clean and spotless. We loved to sit out by the water and watch the wildlife, jet skis and wind surfers. It's so peaceful around there. There are also lots of great restaurants near by. We hope to come back again sometime.

Beautiful place, centrally located, and very peaceful. Great for anyone wanting a relaxing stay by the pool in the daytime and looking to enjoy the restaurants and bars after sunset.

Fantastic stay for the price. Very peaceful place and the staff on property were very kind. The house itself was great. Robin gave us some great recommendations for things to try around the area.

Welp, I’m here actually writing a review. This place was seriously such a cute little spot, kinda hippie but all the way key’s vibes. Coming from a local I’d take a spot like this over a resort majority of the time. The people are friendly and they love animals too which is a super plus. We got to see manatees everyday right up at our house boat, kids loved it. If you’re traveling with multiple families this is freaking perfect. Such a vibe, we definitely will be coming back and most likely make it an annual thing. If you’re nervous about a house boat just book it and thank me later. Also their mini splits keep them rooms ice cold. Freaking love that too

We will definitely be back. Great location to many attractions. Robin was a great host. Very responsive.

Everything and everybody far exceeded any expectations. We have already started planning our next stay. This was easily one of the best experiences I have ever had with any rental service.

Beautifully decorated bungalow with everything you need for a relaxing holiday. We stayed with our two boys who loved the pool next door and the fire pit in the back garden. Great base for exploring Islamorada. Recommend watching the sunset and enjoying some great food at Papa Joes. Lovely responsive host

Wish we could’ve stayed longer. It was a perfect home!

We had such a wonderful getaway at the cottage. The house is so charming and filled with character, something we thoroughly enjoy on our vacations. The location afforded us close proximity to shops and restaurants while also giving us a good home base to explore all the keys have to offer. We started each morning with coffee on the dock while enjoying the surrounding beauty. A manatee family were frequent visitors and even played with us while we were kayaking, a core memory experience, for sure. Jackie is a proactive and responsive host, and she was a joy to communicate with. We highly recommend her and her beautiful property. 🌴☀️

We had a family gathering. My wife and I and our older daughter and husband in one house with our younger daughter, husband and two sons in the adjacent house. Absolutely perfect. Loved the pool in the shared back garden. Would love to stay here again and again. Thank you

Great host and a wonderful place to stay at! Will definitely be back!

What a fantastically beautiful place. right on the canals leading to the sea with spectacular views. Great hosts who were super responsive. Highly recommended

Place was exactly like described, super quaint and had a great homey cottage feel. Neighbors were all super friendly as well. We really enjoyed being able to sit outside on the canal and enjoy our breakfast/dinner as well as playing any games. Would highly recommend this place, not far from key west a matter of 35-45 min depending on traffic

from the time we made our reservation until after we checked out Jenny was great. super attentive. She gave us some local recommendations for Easter brunch and had an early check in available. she had everything we needed to come and enjoy our stay without worry.

Great space with everything you need. Patio is a perfect place to relax. The house is well stocked. Plenty of room for a group. Access to hotel pools/restaurant with transportation into town if you need it. Great host communication. All you could want!

Great experience, great host and accommodations. Hot tub wasn't working while we were there, but repair was delayed over the holiday week which was out of the hosts' control. Very communicative and responsive.

Eric’s place was lovely, well maintained, nicely appointed, and immaculate. The 3 of us enjoyed the balcony overlooking the pool. Even though the apartment is near the airport we only heard planes twice in the 4 days we were there. There is a convenient little grocery store on the site and excellent BBQ from a food truck near the pool. Eric responded to our questions promptly. Comfy beds, everything worked and we enjoyed our stay. Would stay here again.

Very nice condo. Very clean unit. Would stay again. Only inconvenience was no bathroom on the main level. But 2 bathrooms on the upper level. Great value for the price.

This place is a gem! The condo was very spacious and it was supplied with everything we needed, no need to buy any extras like other places we have stayed at- Thank you for that! The pool was fantastic! Walking distance to beautiful Smathers Beach. We did not get to do any water activities due to the wind but we had fun exploring around town. Will definitely be returning!

We had a great stay at Chris’s place in Key West! The property was exactly what we needed for a relaxing getaway. Chris is an excellent communicator—his instructions were clear, detailed, and made everything super easy from check-in to check-out. We felt well taken care of and really appreciated the smooth experience. I’d definitely recommend this place to anyone planning a trip to Key West!

Went for a quick fishing trip. Great location. Enjoyed it so much

Great location!We had a fantastic stay,we didn’t want to leave! Beautiful home,clean and comfortable,we had everything we need.We enjoyed the pool daily,the complex nice and friendly community. Jonelle was responded quickly with any questions I had and provided great recommendations on restaurant and activities! Islamorada has always been a special place to us!Would definitely stay again!Thank you!