Islamorada featuring a beach and tropical scenes

Search Vacation Homes in Islamorada

Upfront pricing

Our total price for your stay includes taxes and fees

Treat yourself

Save 10% or more on over 100,000 hotels worldwide with Member Prices

Learn about One Key

Be picky

Search almost a million properties worldwide

Check prices for these dates

Next weekend

In two weeks

In one month

In two months

Vacation Homes in Islamorada

"Everything just great except need better vaccum"

"We had such a nice time at the Windley Cottage. The owners effectively communicated information about the home and check in before the stay, making arrival very easy. The home was very clean and had everything that we needed. The Anglers Reef area was nice and quiet. We enjoyed walks to the docks, kayaking, and swimming in the pool. We absolutely loved Islamorada and hope to visit again!"

"Clean , beautiful location and pools . "

"We used this as accommodation to explore the keys for 6days and it did not disappoint. Very accurate description of the house. Nice, clean and tidy. Thank you"

"Great location. Beautiful, comfortable accommodations. Would absolutely return. "

"Amazing spot in the Keys. Stayed there the weekend for a wedding in Tavernier and was close to everything we needed. Would definitely stay here again when I come back. "

$373 nightly

Aug 13 - Aug 14

Total includes taxes and fees

"This property was amazing basically brand new definitely recommend "

"We have stayed in one of this Hosts properties for 5 years in a row. Always clean, always great communication and we always have a great time. We highly recommend."

"beautiful and quite neighborhood. "

"The porperty had everything we needed for a great family spring break. The kids especially enjoyed trips to the jetty on the golf cart!"

"This condo and the club is awesome. The pool is wonderful. We loved everything about or stay would come back! "

"We stayed at this property for our spring break trip and thoroughly enjoyed our stay. The home was clean, comfortable, and well-equipped with everything we needed. The location was great—close to local attractions yet peaceful enough for a relaxing getaway. The host was responsive and accommodating, making the entire experience seamless. We would definitely stay here again!"

"This is the best location we have stayed at in Islamorada. The community was safe and quiet, plenty to do right on site with swimming, private beach, kayaks and paddleboards, fishing off dock. We saw manatees most days in the marina. The house is exactly as listed, the owners were quick to respond and fix any issues we had. Would definitely rent again! "

"The unit was set up perfect for my family as well as my brother-in-law‘s for a family wedding in Key Largo. The pools were beautiful. The property was well maintained and we had a wonderful time. "

"Was a nice property and pleasant enough for our stay."

$1,159 nightly

Aug 10 - Aug 11

Total includes taxes and fees

"Beautiful,clean, great location"

"Such a great little property in a awesome community! A from the host he was such a nice person and communicating was superior would definitely rent again! "

"We loved our stay! Plenty of room for all of us, amazing view, beautiful sunsets, and live music every night."

"Nice property . Well kept. Good management "

Save an average of 15% on thousands of hotels when you're signed in

Top Islamorada Hotel Reviews

Chesapeake Beach Resort

10/10 Excellent

"Great resort with lots to do on-site, pool/kayak/paddle boards/chess/checkers. Morning omelette was delicious & breakfast with the iguanas was fun! Great spot if you’re traveling through or on a fishing trip."