Waterfront vacation rentals in Big Pine Key

Had a great stay here. Very nice and great location in the keys.

Rhonda's place is terrific! Lovely location with full water views. Pool was excellent. The home was very comfortable, clean and convenient to restaurants and stores. Would definitely rent again.

Beautiful place with a well stocked unit…close enough to all the places we wanted to visit, yet far enough away for a quiet, relaxing day. We loved the area and our stay here. Thank you, Chris.

Perfect spot for a long weekend beach getaway! This was our first time visiting the Florida Keys, and we loved being right on the water with a small beach area to ourselves. The space was ideal for our group of friends, and the location was great—close to local bars and restaurants, some within walking distance or just a short drive away.

Condo was exactly as pictured. Beautiful resort and everyone very friendly onsite. Great location and close to lots to do. Cannot wait to book again.

An easy and relaxing family trip to the Florida Keys. Central location and a well appointed comfortable apartment. We will definitely return!

We arrived early on the day of check-in, and because previous guests has left early, we were able to check in first thing in the morning! Henry happened to be in Key West, working around his property, so he very kindly gave us a full tour of the apartment, the parking area, the grounds, pool, and beach. The apartment is whimsically decorated with pastel colors to fit the Key West vibe, and has lots of cute details. Amazingly, all the small appliances, dishes, glasses, and tableware are in the pink/rose colored family. Literally every appliance is pink (Cuisenart, coffee maker, toaster, Keurig, blender, tableware, and more). It gave the place a unified cozy feel. The living room is spacious, with lots of couch room for a family to watch TV together. The kitchen is eat-in, and the bathrooms and bedrooms are super nice. We felt very at-home in Henry's place, and appreciate the details he provides about checking in, keys, garage parking, etc. We had a great time.

The location, condo, grounds, access to restaurants and proximity to our fishing destination made this stay enjoyable. At the top of our list for our next trip.

We loved our stay at Jeffery's house. It is spacious and very comfortable. My husband appreciated the proximity to the pickleball courts - we could see them from our bedroom windows- and my son enjoyed fishing off the dock. The upper suite was wonderful for privacy and quiet when the older kids stayed up later than the adults. Jeffery was super helpful and responsive. We would love to stay here again!

We all loved the house. Plenty of space, the outdoor patios were a daily hangout, the views were great, what's not to love. The maintenance of the house itself was excellent and it didn't feel like a "rental". Well decorated, not worn down, a bathroom for everyone, it was great. We rented a golf cart to get back and forth from town which was very easy and barely a ten minute drive. We did have a small issue with the pool while there, which apparently is very unusual. It is Key West so it took a few days to get the parts needed. However, Javier was always easy to reach and while he did eventually fix it it was his 'out of the box' thinking and communication on everything that was superbly professional. I understand he manages several properties and we would gladly stay at any of them. With an AirBNB, if something goes wrong and you're far from home all you have to rely on is the owner/manager and you are in excellent hands with Javier. A++ on customer service

We had a wonderful family vacation at Naomi’s place. The place was perfect for our family of 4. There was so much to do to keep our active family busy. The house was well stocked with everything you may need for meals. Host was very responsive and helpful throughout our stay. We rented a boat and the dock was perfect for storing. We are looking forward to staying here again on our next visit to the keys!

Our first stay at this property was truly unforgettable, and we can't wait to return! Francisco is an outstanding host, always quick to respond and attentive to every detail. The house exceeded our expectations—it was spotless, fully equipped, and conveniently located near stores and restaurants. The outdoor area was a peaceful and inviting space, thoughtfully designed with a refrigerator, sink, hot tub, gas fire pit, and ceiling fans to keep you comfortable. The soft lighting added a warm and welcoming ambiance, perfect for evening gatherings or simply relaxing under the stars. We especially loved the canal, which was incredibly easy to navigate and provided quick access to the ocean—a paradise for fishing enthusiasts! We even caught fish right in the canal, but the absolute highlight was spotting manatees from the dock. If you're looking for the perfect getaway, look no further. Book your stay with Francisco—you won’t regret it

We didn't know anything about Key Colony so based our reservation strictly on reviews and price. Well worth every penny that was spent. What a wonderful tropical getaway! Can't wait to visit the Keys again with my 4 children and husband. If you're looking for a great place to spread out and enjoy family this should be your rental.

The hosts were so accommodating and friendly. The space was newly remodeled with excellent quality and style of workmanship. It was also immaculately clean and incredibly well stocked. Our family of five (three young adult boys) was always comfortable. The hosts thought of everything you could want on vacation. They worked with us to make sure we had a place to dock and use our wave runners, there was outdoor dining and grilling space, complete with a filtered ice machine and an outdoor chest fridge for any fishing, a beautiful spot overlooking the canal, a pergola over the sitting area to provide extra shade, and the house itself was gorgeous and well appointed with plenty of space. We’d love to visit again!

Jorge was an excellent host! The home is beautiful, right on the canal. It is very well stocked with thoughtful amenities. We particularly appreciated the paddle board/kayaks, beach chairs/umbrella, and well-supplier kitchen. We would recommend his home to anyone visiting the keys!

Place was great, location, clean and ocean views awesome all around. Fishing was good out back caught a nurse shark, snappers and other small fish. Kayaks were excellent to get out front for mangrove and snook fishing. Definitely recommend !

Carrie's place was absolutely beautiful! it was so clean, the beds were insanely comfortable, and there were tons of linens and towels for everyone. We very comfortably fit 8 people into the home with no problems. The view from the balcony is absolutely amazing and we were all blown away. Carrie was extremely responsive and friendly. We were here for our wedding and had our wedding party stay here so it was extra magical. The pool and hot tub is super close, elevator to help with our bags, and the resort itself is gorgeous. 10/10 would stay again. We loved it so so much! Don't miss out.

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.

Nice, clean and quiet place. pool was nice. Nice view off the balcony is of the mangroves. Beach area is nice but pretty rocky once you get into the water.

The unit is just like the photos and was very comfortable! John was helpful and helped make for an enjoyable stay! Would happily stay here again

We had a fantastic stay at this condo in Tavernier! The location was ideal—close to everything we wanted to see and do in the Keys. The unit was clean, comfortable, and well-stocked, with a beautiful view of the ocean that made every morning feel like a dream. The host was extremely responsive and made everything easy from check-in to check-out. Highly recommend this place—we’d love to come back!

Beautiful views, well appointed condo, great amenities and location is very convenient.

Great little place for our family of 4! Very clean and the location was perfect for us. Would definitely stay again!

We loved our stay at Nicole’s place. It was well stocked, super clean, and the decore was lovely. This is second time at Ocean Pointe. We enjoyed being in building 5 and the larger corner unit.