Fitness-friendly holiday rentals in Sunset Key

We had an amazing time at Peggy and Jim's condo! Great location on the southern side of Key West not far from the airport. Walking distance to some amazing breakfast spots and Cuban-inspired coffee shops. Also just a short Uber ride to Duvall street and pretty much any major attraction you would want to see in Key West. The condo was perfect for a family of four with a great pool and ocean views and beaches within walking distance. The host was excellent at communicating before and during the trip. Would definitely stay here again. A+!

We loved our stay at Judy’s. I have special needs and this place was perfect. I highly recommend staying here.

Nice cozy spot while visiting Key West.

The Condo was spacious, beautiful, well furnished, very clean and the location was perfect. Henry was great to work with. We rented a golf cart and traveled almost everywhere in Key West by golf cart.

My boyfriend & I have been coming to Skipjack for his birthday for the last two years & we absolutely love it ! It has become a little tradition. We love the space and the dock in the back! During our stay we saw a manatee, a Manta Ray, & lots of Tarpon in that canal. Absolutely beautiful. The location couldn’t be better as it’s right in marathon, where you are close to Sombrero Beach, Publix, lots of delicious restaurants with great ambience, etc! We look forward to our next stay at SkipJack!! :)

Chris's spot in Marathon exceeded all expectations - the view from the balcony looking out onto the ocean was breathtaking with beautiful sunsets every night. Great restaurants nearby including a tikibar behind the property. 10/10 stay and would absolutely recommend this spot to anyone looking for a place to stay in Marathon.

Great place to stay. Not too far from the main Key West attractions.

My fiancé and I recently stayed at beachside resort and we Connor say enough. The location is absolutely unbeatable — just steps away from the beach! Waking up to the sound of waves and enjoying coffee on the balcony with an ocean view was pure bliss. The rooms were spacious, beautifully decorated, and immaculately clean. Everything felt fresh and well-maintained, with thoughtful touches that made it feel like a home away from home. The amenities were top-notch. We loved lounging by the pool overlooking the sea, and the bar was the perfect place to unwind with a cocktail while watching the sunset. Highly highly recommend.

The experience was so memorable! Just the R&R our family needed!

Woooow, this place was nothing short of amazing!! The exact amount of space we needed because we knew we would be out and about most of the day!! Bed was very comfortable and ushered us right to sleep after our flight! Walking distance from literally everything we had on our list to do! We mingled with the locals, listened to live music during dinner, enjoyed the beach at sunset, and learned a little bit about the Bahamian history! This place is literally 2or 3 blocks from the southern most point and the best Cuban coffee at a local restaurant/food truck! 10/10 would definitely recommend!! Already planning our next visit!!

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.

Perfect spot. Place, view, location were great.

Exceptional stay. Anchor Drop was a top Airbnb property in our book.,Would definitely look to return to both Key West and the property. Host was responsive, explicit, and helpful. Space was as described and very well appointed, clean, and comfortable. First time to Key West and was very satisfied with our accommodations, location, and area. Thank you!

This beautiful condo was so much more wonderful than the pictures portrayed! It is the most amazing location and setting with a stunning courtyard garden, ocean views and its own little beach. I felt like I stepped into Paradise! The complex was quiet, respectful and beautifully maintained. The location on the island could not be beat with a short walk to Smathers Beach and Higgs Beach. This was our first time in Key West and it was pure magic! Thank you!

We had a great stay here! Everything was clean and had no problem with anything at all. We would definitely stay here again.

Great place, clean, nice location, and complimentary snacks and water on the fridge, which was a pleasant surprise. The location is well-maintained and strategically situated, providing an overall positive experience.

Tammy was wonderfur, loved how attentive. The house was beautiful and close to so many great restaurants and things to do. Next door was the marina rented the boat, had a great breakfast at the French bakery down the street we could walk too almost everything. Loved it!!

The stay experience exceeded our expectations. The only recommendation would be to have a listing of recommended restaurants, beaches, boat rental places, etc to go see in both Marathon and key west. We visited key west and found out afterwards where we should have gone.

I loved the stay at this house. Would definitely come again.

Such a wonderful location! We were looking for a location that offered quietness, safety, views, and we found it here at KCB! Canal view across the street. Mile to mile in a half walk to Sunset Park, 5 min walk to The Glunz Beach Resort. We all loved that the rental came with access to the beach resort!m- perfect for our two teenage daughters. Beautiful white sand and blue water. The rental was very nice, and felt like home away from home. Also really like that KCB has law enforcement, and they were always present. We would definitely stay at this location again if we’re to visit KCB again. Thank you for sharing your beautiful home.

Nice place was just what we need for stay.

We had a really great stay here - 2 families of 5 and there was room for everyone to sleep. There’s a pullout sofa in a smaller office room that one 14 year old slept on. There’s house is super clean and the hosts were very helpful even after hours when we asked them to help put cold groceries away at 10 pm due to our flight be delayed!! It was so appreciated to salvage all the money we spent on them. Thank you!! The backyard is very private and has tons of beautiful trees and plants and our 6 kids loved the pool after our days on the boat. We had a boat and it was a little tricky to park at the dock bc a little tight at the end of the canal but it was fine even at low tide. We’d stay here again for sure especially based on the great customer service by the management company (although house is listed for sale so might not be available).

The house was exactly how it was described online. Everything was well marked. Lots of stuff to do at the home. Very spacious and well maintained. There were only 7 of us, so lots of extra space. The pool is on the perfect side so your not blasted with the late afternoon sun. However, there is a huge umbrella in case it is needed. Kitchen is fully stocked so nothing was needed. There is a BBQ grill as well as a flat top which is nice for outside cooking. The only thing I would recommend is to bring your own pillow if your a particular pillow person (we love our feather pillows), house pillows were not feather ones. If you rent here and have a boat definitely go to the Sombrero Lighthouse to snorkel. Never saw so many fish in one place. The Conch Cafe and Coast to Coast pizza are both great food restaurants and walkable from the home. Publix is so close it was a daily visit. Truly enjoyed the week stay!!!!!

Thank you soo much for hosting us Irene! We truly appreciate you having us. We had an amazing Key West! You were a wonderful host. I’d definitely recommend anyone book here!