Waterfront vacation rentals in Big Pine Key

Key Colony Beach is truly the gem of the Florida Keys. Staying at Cindy's apartment in the Continental was the perfect fit for my husband and I. The private beach was clean, easy to access, and just steps from the accommodation. The overall vibe here was quiet and peaceful, and the apartment had all the amenities we needed for a 5-day stay. Cindy's space is very clean and well-appointed. This location is perfect for morning walks around the immaculate and safe neighborhood, or short jaunts to Key Colony Inn or Havana Jack's for dinner/drinks. Honestly now, you're already here! What's your hurry? :)

We had a great time in Tavernier area. Tina’s place was the perfect setup and the amenities were wonderful. We would definitely stay here again. Thanks for sharing your beautiful condo.

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.

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!

The outdoor space is absolutely fabulous. The heated pool was enjoyed every day. The property is on the corner of two canals that had pretty clean water. We met several manatees who graced us with their presence often. Fishing was not great during the month so our fishermen were rather disappointed. The interior was very pleasant and cooking was easy. The entire third floor is the master sitting room, bathroom and bedroom. The only drawback for me personally is that the master bathroom is an "open concept " design which left me without a sense of privacy. Isa was extremely helpful and responded quickly with our questions. Thank you Isa!

The house is beautiful and well stocked. Javier provided ample information to facilitate a smooth check in process and to help my family plan for our stay. Would 100% recommend this listing to a friend!

Had an amazing stay at this house with my husband and 4 small kids. The house was spacious and clean, with lots of natural light at soon as the sun came up. The pool was so warm and had a large shallow area that was perfect for our 3 year old. Naomi was a wonderful communicator. It was so sad to have to leave.. Would definitely recommend staying here.

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.

We had an amazing week stay at this property. It was spotless with too of the line amenities. The street is very quiet with little to no traffic located at a dead end canal street. Bonus that we were able to dock our boat and it was pet friendly. The kitchen was fully stocked and we were very comfortable. We would definitely stay here again! This place is beautiful and exactly what we wanted for our week’s stay in Marathon.

Great Choice in Key Colony!! We were two couples and everyone enjoyed the stay - place was immaculate, eating outside looking at the canal, watching the birds/pelicans. We did have a manatee visit one day as well. Easy drive over to Sombrero beach and many very nice restaurants around. Having access to the Cabana club and the pool was an added benefit/interest. The place does have two bathrooms which I wasn't sure of when renting. Jorge was very nice.

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.

This great little place on Duck Key had so much to offer for being a home away from home. All the amenities to make it flexible for us to dine in some nights and go out others. The location was beautiful and peaceful. Our stay was during the unfortunate fires down highway 1 and she kept us up to date on the road situations so we knew if we were able to get down there. She checked in on us after arrival and offered early check in so we could get there while the roads were open. We can’t wait to go back and make it a family tradition!

Expect a nice, relaxing time. Beautiful scenery and lots to do in Marathon Key.

We loved everything about this place. It was super clean and fresh. The bedding was very comfortable and felt expensive. We drank coffee on the balcony every morning watching the ocean. The oceanfront pool area was clean and well taken care of. The unit was stocked and well labeled with all that we would need and more. The garage door opener for inside private parking was amazing. We watched the Tyson fight in the living room on the BIG tv! Had a great vacation. Thank you.

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

Place was just as described! Pictures were spot on. We really enjoyed the property and it felt like a resort. Pool was very nice, clean and we enjoyed the little bar and grill for some pina coladas poolside. The unit was very quiet, and had everything we needed. We appreciated they had plenty of towels and linens so that we had an extra set during the stay. Surrounding area was great easy to find anything we needed and lots of great restaurants!!! The pull out coach is a memory foam mattress vs a spring mattress which my kiddos really appreciated making it so much more comfortable! Beds in the rooms were also very comfortable with nice comfy covers! Would highly recommend and would stay again!

Michelle was great! Very responsive and understanding when we had to make a last minute trip change. Unit was clean, bright and had a nice view. It’s a nice location between Key Largo and Islamorada making it convenient to explore both. We didn’t use any of the resort’s amenities, but there was an influx of seaweed at the small beach. Just one downside of this time of years in the Keys. But the pool looked great!