MINIMUM STAY: 28 DAYS Villa Riolo is an updated single family stilt home and perfect for your next holiday in Islamorada! It comfortably sleeps 6 in two bedrooms. This home has been meticulously cared for over the years and for the first time the owners are offe …see more
13 Aug 2014
Was a very clean house with all the amenities. I would stay again. Easy access to the Ocean for fishing and plenty of dock for your boat.… More
Minimum Rental: 1 Month Charming vacation home located in the beautiful neighborhood of Port Antigua. You will love this home! There is a wonderful open concept floor plan with 3 nicely proportioned bedrooms. Sliding doors open from the dining area into the sunr …see more
Minimum Rental: 1 Month Everything in this unit is exquisite - furnishings, linens, updated kitchen, appliances, and bathrooms. Great views of Florida Bay and our fabulous Keys sunsets. This complex is conveniently located just steps from a full service marina and …see more
15 Apr 2014
"Paradise on the ocean"
We rented Palm 417 for the month of March 2014. The condo has been very nicely updated and although not direct ocean front view; it does have partial view of the ocean side and a good view of the bay … More
Minimum Rental: 1 Month You will love jewel of a home! Located in Lower Matecumbe, this charming canal front home offers a swimming pool, dockage, direct access to the ocean, covered fish cleaning station, a screened lanai, inviting décor and comfortable accommoda …see more
24 Aug 2013
"Our Lobster Trip to the Keys"
My family and I stayed at the Matecumbe Jewel in the month of august for Lobster season. The home shows even better than the photos, was clean, well furnished and kept. We could not have asked for be… More
Minimum Rental: 1 Month Location, location, location! This home has it all - ocean side Lower Matecumbe location, totally remodeled in 2009. Relax by the cocktail pool or sunbathe in the private roof top sunning area. There are blue water ocean views from almost e …see more
15 Jul 2013
"Blue Water = Everything that you want"
This place delivers.
You never really know what you are going to get from looking at a website and photos. I just stayed there July/2013 and this place is great, everything is new and clean. Most of … More
Minimum Rental: 1 Month Oceanfront - Beach - Protected Dock and located in the Fishing Capital of the World - Islamorada. Realize your dreams - a beach home located on a swimmable beach and a place to dock your boat. This home is indeed a rare find in The Florid …see more
23 Jan 2013
"My Paradise from architect's perspective"
My wife and I spend a month at My Paradise and, as an architect, there are certain aspects that bear mention. First, if the weather is mild, you can open the wall of folding glass doors and unite the … More
Minimum Rental: 7 Nights (Saturday to Saturday) BROCKHAUS ON THE GULF is an end unit townhouse on the water's edge with water views on 3 sides! The main living area faces the Florida Bay, one side faces the inlet leading to the marina basin and the back faces the mari …see more
2 Apr 2014
"Absolutely Beautiful and convenient for boaters!"
Our family stayed here for a week in late March. We had plenty of room and everything we needed was available. This is a gorgeous condo overlooking the Florida Bay. You get to see an awesome sunset ev… More
24 Mar 2014
My family of 5 stayed here for 8 days during early March. Hands down... this is a show up and start relaxing type of rental. The only, and I mean only, thing that was missing from this place was a co… More
1 Jun 2014
"Fabulous location in the Florida Keys."
Having stayed in other properties at Futura Yacht Club over the years, I can honestly say that this was by far the nicest. The kitchen had been recently renovated with new white goods, and the whole p… More
Minimum Rental: 7 Nights Lower Duplex - This is one of three rental units on this fabulous property. The Little Bay property is a one acre lush tropical setting in a gated compound located directly on Florida Bay. The units are available for rent by the week, or …see more
30 Jul 2013
"Little Bay Fabulous Stay"
We had the pleasure of staying at Little Bay early July...2 couples, 1 pup and our boat. It was fabulous! The view, location, property was exactly what we hoped for. Private but close to restaurant… More
3 Jun 2013
My family and I spent Memorial Day Weekend at this gorgeous property and it was like paradise! Not only was it beautiful inside and out it had a sophisticated charm and inviting ora from the moment y… More
Thank you very much for your kind words. It was a pleasure meeting you and your lovely family. We are delighted that everything exceeded your expectations. We look forward to your return!
Andi, Ashely, Kathy & Dick
Keys Holiday Rentals
21 Aug 2013
Our family rented both the upper and lower duplexes and had a wonderful time. The management people were super friendly and had tons of information and ideas/recommendations for anything you could n… More
Minimum Rental: 7 Nights Cottage - This is one of three rental units on this property. The cottage is a ground level dwelling separate from two duplex units. It offers a unique floor plan with the main living area in the center of the house with kitchen, dining are …see more
28 May 2013
"A place where memories are made....."
The pictures really don't do this place justice, there are so many comforts that it feels more like a home. It is in a great location and since it is gated, it was safe enough for my 9 year old twins … More
Minimum Rental: 7 Nights Upper Duplex - This is one of three rental units on this fabulous property. The Little Bay property is a one acre lush tropical setting in a gated compound located directly on Florida Bay. This is one of 3 separate units for rent by the we …see more
13 Jan 2015
"Classic Islamorada - Amazing Property"
Little Bay was a perfect property for us! The setting is idyllic and classic keys - Huge backyard on the Bay with excellent dock area, hammocks and view of the bay. Covered porch was the full width … More
2 Jul 2013
"I just love it here"
We have rented the upper duplex of Little Bay in April for the last few years. it is a beautiful property in a perfect setting. The grounds are kept immaculately and the area by the water is so nice… More
5 Nov 2012
"Iguanas, sunshine and the sea in your backyard......."
We found Little Bay after our previously planned accomodation had been damaged in a fire so Andi & Katy at Keys Holiday Rentals literally saved us from camping on the beach! The apartment couldn't ha… More
Minimum Rental: 1 Month Sensational oceanfront views are yours from both the master bedroom and the balcony of this beautifully appointed condo. Watch the fishing charter boats as they come and go from Bud and Mary's Marina. You'll be able to see cruise ships as …see more
13 Feb 2015
"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 mas… More
Minimum Rental: 7 Nights You can have it all – privacy and convenience. The owners of this wonderful property called Sunshine Place are willing to share a portion of their piece of Paradise with you. The ground level living area of this home is perfect for one or …see more
13 Mar 2015
"Perfect place for a couple to vacation."
If your looking for the whole package in one this is the place. View, comfortable, privacy and location. Best place I've stayed in the keys, hands down!… More
1 Mar 2014
"a jewel worth the search"
Dog friendly, spacious location for relaxing or as a base for exploring the upper/middle keys. The property is shoehorned between two resorts, but surprising quiet and even secluded, in a way. Plent… More
8 Jul 2013
My wife and I just returned from a weeklong stay at this property. I have to say this is far and away the nicest 1 bedroom rental and as far as I'm concerned a hidden jewel in Islamorada. It is the bo… More
Minimum Rental: 1 Month This is a very special unit in a premier condominium complex located directly on the Atlantic Ocean and in the heart of Islamorada. This unit provides spectacular ocean views. It is one of the few units that offer spiral stairs to the groun …see more
Minimum Rental: 1 Month Gorgeous 2 bedroom, 2 bath condo. This is a gated complex located directly on the Atlantic Ocean. This unit has unobstructed views of the ocean from the master suite and the balcony. Wake up every morning, open the curtains and view a panor …see more
Description….. MINIMUM STAY: Minimum Rental: 1 Month 5th Floor unit at one of Islamorada's favorite condo complexes. This unit was recently sold and the new owners are beginning to update some of the décor. You'll love the fantastic panoramic ocean view …see more
Minimum Rental: 1 Month Beacon Reef is one of the most desirable condominium complexes in the Upper Keys. Located in Islamorada it is convenient to everything - restaurants, fishing, diving, snorkeling, swim with the dolphin programs and much more. Picture yours …see more
Minimum Rental: 1 Month This exceptional condo has been impeccably maintained and is located in one of the finest condo complexes in Islamorada. It features an updated kitchen, remodeled baths and is comfortably furnished. This unit is ready for your arrival. Be …see more
MINIMUM RENTAL: 28 NIGHTS (ONE MONTH) You'll love watching the fabulous sunsets over the tranquil waters in this semi-private lagoon setting. This is a three story single family home and offers two balconies overlooking the water and dock area. There's room to dock one …see more
Minimum Rental: 1 Month Extraordinary ocean front condo with panoramic views of the Atlantic Ocean. Relax on your own balcony or use the spiral stairs to access the sandy beach below. This condo is located in one of the most prestigious condo complexes in Islamo …see more
Minimum Rental: 1 Month Comfortably furnished and ready for you. Conveniently located just steps from a full service marina and 2 highly acclaimed restaurants. Watch the sun rise over the ocean as fishing boats leave on their daily charters, or watch the spectacul …see more
Minimum Rental: 1 Month Pure pleasure will be yours in this beautifully remodeled and immaculate condo. You'll love the uncluttered and modern décor along with the recent renovations. Enjoy the picturesque views of Alligator Reef and the Atlantic Ocean from t …see more
Minimum Rental: 1 Month New on the rental market. This is your opportunity to secure your winter getaway at a luxurious oceanfront condo in one of Islamorada's most prestigious condominium communities. Ocean front dockage is available for boats up to 28' in length (s …see more
MINIMUM STAY 29 DAYS. BEAUTIFUL CANAL FRONT STILT HOME WITH HEATED POOL - For the guest who expects perfection this is it. This home was completely remodeled in 2013. There is 936 square feet of living area on the main level with 2 bedrooms, a full bath and an ope …see more
MINIMUM STAY: 29 DAYS Enjoy unobstructed and panoramic views of the Atlantic Ocean from your own private balcony! This 3 bedroom/2 bath condo unit features direct ocean views from the living room, balcony and two of the three bedrooms. Tropical furnishings creat …see more
Minimum Rental: 1 Month A Diamond! Be among the first to rent this gorgeous two bedroom condo. It has been completely renovated from floor to ceiling. The floors have been replaced with tile and the old popcorn ceilings are gone. You'll adore the comfortable livi …see more
MINIMUM STAY: ONE MONTH. Exceptional 5th floor (top floor) 2 bedroom 2 bath condo at Beacon Reef. Ocean views from the open air balcony. You'll be so glad you have chosen to spend your holiday here. The kitchen was remodeled in 2013 - granite counters, stainless …see more
MINIMUM STAY: 29 DAYS Exceptional condo with panoramic views of the Atlantic Ocean. This condo is in one of the most popular condo complexes in Islamorada - The Palms of Islamorada. Comfortably furnished and ready for your arrival this unit offers an updated kitche …see more