Holiday Homes in Sugarloaf Key

Change your mind

Book hotels with free cancellation

Treat yourself

Be picky

Search almost a million properties worldwide

Check prices for these dates

Next weekend

In two weeks

In one month

In two months

Featured Holiday Homes in Sugarloaf Key

"We absolutely loved our stay at the Delaney house. The pool and outdoor area were lovely and private, the location was excellent and walking distance from fun Key West spots but quiet and cozy, and the beds were all incredibly comfortable! Would definitely recommend this place to everyone!"

"This was a great location and easy place to stay. We were able to walk to many locations in Old Town. The new updates are a nice addition to this location. Fresh paint, refrigerator, A/C and the patio is a great place to relax. "

"Really like the home and everything was perfect."

"Great location and overall experience. "

"Very nice place to stay. Quick and efficient communication with host! Seemless check in and check out process. "

includes taxes & fees

18 Aug - 19 Aug

"The location was excellent—just a short walk to Duval Street. The property was spacious enough to comfortably accommodate our family of five, and having three bathrooms was a big plus."

"Perfect place to stay. Great location. "

includes taxes & fees

13 Aug - 14 Aug

"Clean, home included everything you could need. Best of all, communication was clear, friendly, professional and a binder was left with activities, restaurants, etc. Parking spot was clear and easy. Beautiful stay"

"Wonderful stay!"

"This property is perfectly located near Duval street and within walking distance to the marina. A perfect location for those wanting to shop and enjoy the amenities the marina has to offer. We can’t wait to go back. "

"Had a great time, easy check in and great location!"

"Property was adequate but could use a few updates. The location was great. Easy to get to Key West near good local restaurants and beaches. Would stay again. "

includes taxes & fees

16 Aug - 17 Aug

"The units were perfect and the customer service was amazing. "

includes taxes & fees

31 Aug - 1 Sept

"We had a great time and loved the property "

"It was a great location in the back, not on the main road. Very quiet, great view, and good place for kids if you are traveling with kids. Used golf carts and was able to get everywhere in 5-10 mins. Overall great vacation and awesome location to stay. "

"Great place. well located. Will be returning."

"We had a great time in Key West. The location of this property was great, allowing us to walk pretty much everywhere we wanted to go. The unit was clean and provided all the basics we needed. Will definitely consider staying here again."

includes taxes & fees

31 Aug - 1 Sept