Keys Holiday Rentals

Islamorada and the Florida Keys are home to North America's only living coral barrier reef. The warm clear waters surrounding the Keys are a mecca for watersports. There is truly something for everyone; sport fishermen, SCUBA divers, snorkelers, and those looking to enjoy active watersports, eco-tourism, or just a more leisurely pace of life near the water. Our team at Keys Holiday Rentals is eager to assist you whether you are visiting us for the first time or simply your next time!

Keys Holiday Rentals represents a wide variety of properties throughout the upper Keys, all uniquely furnished and decorated. Let us assist you with planning a couple’s getaway, a family vacation, or a group trip where you need multiple properties for family, friends, or colleagues. Our experienced team of vacation rental professionals is here to make your Florida Keys holiday a success!

What Our Guests Say

Heaven on the Bay

Our stay at A410 was absolutely perfect! We ventured out a few times but staying on Moon Bay property was what we enjoyed most. A one week stay was not enough, next visit will definitely be for longer.

DEBRA 4-16-2022
Conch Bar South

This was our first visit to the Keys so what we knew before coming to the area was learned through internet searches and friends. The website for Conch Bar South is nicely done, but certainly can’t convey what it is like to actually set foot on this property. Everything is amazing. The setting of the house with the incredible views of the bay, especially the sunrises and sunsets (not a one was missed during our month - long stay) provided daily inspiration. The spacious home was absolutely beautiful with ocean - themed art, tasteful furniture, well - stocked kitchen, and excellent amenities. The home, the yard, the pool, and the dock were clean and well maintained. The guide book provided by Keys Holiday Rental contained very helpful informatio n about the property and things to do in the surrounding area. There is so much to do in the Keys and we certainly took advantage of many opportunities. That said, there were many days we just wanted to be at Conch Bar South and enjoy everything the home h ad to offer.

Rob and Janet C. 1 - 8 - 2022
Villa Riolo

This is our second stay at this property and both times it exceeded our expectations. The house is well equipped and the location is fabulous. Great near - by spots by car or boat. Additionally the Keys Ho liday Rental team was amazing and took care of every detail!

Maria M. 7 - 30 - 20
Palm Harbor

Excellent winter of '18 in Tavenier. House was great, having our boat at the dock was fantastic. House was the perfect location for great boating on the ocean and bay sides - kayaking was good too. The house was spacious and well equipped and the pool was nice. We had a great time, we will be back next winter!

Bill F. 5 - 8 - 2018
Beacon Reef 310

Can't say enough great things about our stay at Beacon Reef 310!! From the moment you walk into the condo we knew we loved it, The whole place had that bright tropical feel about it.. The view from the deck was amazing, what a picture to wake up to every morning.The owners Tommy and Becky have thought of everything. the compl ex is amazing with everything you need right there. We didn't won't to leave. We would recommend this condo to anyone.. Can't wait to return.

Becky S. 10 - 11 - 2018
The Palm s 314

"Wow, what a beautiful view" This condo was clean, nicely furnished and had a view to die for. We really appreciated the washer and dryer in the unit, which most did not have. Also, being on the end we had "the window" in the master bedroom and in the dayt ime the view would take your breath. As for the complex, everyone was very friendly and we made some very good friends. The pool was heated and the hot tub was always warm and enjoyable. We have already made plans to go back next year. If you have the chan ce to rent a unit there, GO, you will not be sorry.

Cindy F. 2/13/2015