2 BR | 2 BA | Sleeps 4 | Quick View
Key Amenities
About this property
Tropically furnished, privately owned condominium at the Futura Yacht Club in the Village of Islamorada. Futura Yacht Club is a gated community located on the Gulf of Mexico and consisting of 70 units. Enjoy your morning coffee watching the boats go out. Relax with a amazing sunset and a glass ...
Property Type
Islamorada Condo
1 BR | 2 BA | Sleeps 4 | Quick View
Distance to beach: 5 miles to Anne's Beach
Key Amenities
About this property
The Osprey Nest (MM 82.3) is a private condo residence which is wonderfully maintained. It is the total upper floor of the building in the foreground. It is operated under FL DBPR license # MOT 5403060 and is inspected annually. This Non-Smoking home is professionally cleaned prior to your arrival. ...
Property Type
Islamorada Condo
3 BR | 2.5 BA | Sleeps 6 | Quick View
Key Amenities
About this property
Enjoy the sunrise over the Atlantic ocean or relaxing on a private, sunny lanai. Take a cruise around the many canals or out to Florida Bay to capture the sunset. A 30' boat slip is included with the rental. Beautifully furnished living spaces, large dining area, granite counter tops and stainless ...
Property Type
Islamorada Condo
We love Bay Harbour Condos! We've stayed in the community 3 times so far and this condo- WILL NOT DISAPPOINT. It's beautifully decorated and very spacious. Owners are sweet and communicate very well! We ...
2 BR | 2 BA | Sleeps 5 | Quick View
Key Amenities
About this property
Luxurious and large 2 bedroom 2 bath condo with balcony, large heated swimming pool, stainless steel appliances, flat screen televisions in every room in the beautiful Florida Keys.Huge ocean front dock with plenty of room for fishing! Wifi, deluxe cable, and restaurants within walking distance.2 ...
Property Type
Islamorada Condo
This home was perfect for our family of five. Spacious bedrooms, living area and bathrooms. We also had use of the storage unit for our fishing gear and coolers. The pier is breathtaking. Our thoughtful ...
2 BR | 2.5 BA | Sleeps 4 | Quick View
Key Amenities
About this property
Welcome to Anglers, a newly renovated luxurious escape for your vacation needs. Perfect for families, couples, or a friends getaway. Located in Anglers Reef, a gated community with heated swimming pool and two private beaches. Our availability calendar is always up to date and current.Our beautiful ...
Property Type
Islamorada House
1 BR | 1 BA | Sleeps 4 | Quick View
Key Amenities
About this property
#41 Windley Key RV Park84961 Old Overseas Highway Islamorada, Florida Keys 33036 1 bedroom + sleeping loft with boat dock. $2900 per month includes all utilities. We are limited by Condo Association rules to 4 rentals a year so there is not a lot of traffic in and out of the unit and it remains ...
Property Type
Islamorada Mobile Home
1 BR | 1 BA | Sleeps 2 | Quick View
Key Amenities
About this property
The Jetson's House apartment (Located on the prestigious White Marlin Beach - which is considered one of the nicest natural sand beaches in the Florida Keys) features great swimming, snorkeling, and spectacular sunsets right off the beach! Have fun exploring an artificial reef! What makes the beach ...
Property Type
Islamorada Apartment
Lower Matecumbe Key is beautiful and secluded. You need to be a boater with a boat or enjoy water sports, or just like the quiet. This unit is small, regular bed. There are plenty of items on the property ...
3 BR | 2 BA | Sleeps 6 | Quick View
Distance to beach: 0.5 miles to White Marlin Beach
Key Amenities
About this property
House, 3 Bedrooms, 2 Baths, Sleeps 6Villa Marlin , 122 Nautilus Drive, Islamorada, Florida Keys mile marker 74.5 bay side, White Marlin Beach located 75 miles south of Miami and 75 miles North of Key West. It has three bedrooms, two bath, private home totally renovated and remodeled, new furniture ...
Property Type
Islamorada House
My friends and I (total 6 adults) rented this beautiful home for a birthday celebration. The home is absolutely beautiful and in close proximity too many features within the Keys. The house has water craft ...
3 BR | 2 BA | Sleeps 6 | Quick View
Key Amenities
About this property
Great house! Great location!House On Canal… 40 foot concrete dock with fish cleaning stand, water, electricity and dock ladder. Bring your boat, great boat ramps. The house is a short distance to supermarkets, movie theaters, dive shops, and full service marinas with fuel, bait and tackle. ...
Property Type
Islamorada House
3 BR | 3 BA | Sleeps 8 | Quick View
Key Amenities
About this property
*LOVE FISHING** Enjoy catching yellow tail, red snapper or grouper. Cast –offshore for sport fishing in the Gulf Stream for marlin, sailfish, black-fin tuna, mahi-mahi, and many more ocean treasures. BACKCOUNTRY—catch speckled trout or tarpon, bone or redfish.**LOVE SNORKELING OR DIVING**Living ...
Property Type
Islamorada Estate
3 BR | 3 BA | Sleeps 8 | Quick View
Key Amenities
About this property
Ocean Front, Lush Gardens, Private Beach, Deep-Water Dockage, Brand new Pool with Spa.This luxurious and newly renovated home is situated on the very desirable Lower Matecumbe Beach in Islamorada. This gated home offers supreme peace and privacy overlooking the Atlantic Ocean. Over 4,000 sq feet of ...
Property Type
Islamorada House
3 BR | 3 BA | Sleeps 12 | Quick View
Key Amenities
About this property
**AMAZING SPECIAL! 25% OFF RENT MARCH THROUGH AUGUST 2019!** MINIMUM STAY: 28 DAYS “Sunrise on Sunset” is the ULTIMATE BEACH FRONT HOME. There are BREATH TAKING OCEAN VIEWS from almost every room in this house! Play in the sand, walk into the ocean or sit under the covered ground level ...
Property Type
Islamorada House
2 BR | 2 BA | Sleeps 4 | Quick View
Key Amenities
About this property
Minimum Rental: 28 Days NEW ON THE RENTAL MARKET. PHOTO UPDATES COMING SOON. "Beacon Reef 522" offers magnificent 180 degree oceanfront views. Enjoy the sea breezes as your relax on your private balcony and gaze at the water. Whether staying one month or more you will be more than happy ...
Property Type
Islamorada Condo
2 BR | 2 BA | Sleeps 4 | Quick View
Key Amenities
About this property
Minimum Rental: 28 Days NEW ON THE RENTAL MARKET. "Beacon Reef 406" is an excellent choice for your vacation getaway, whether you're planning on staying a month or the entire season, this is a great unit. Beacon Reef is centrally located in the Heart of Islamorada making it convenient ...
Property Type
Islamorada Condo
4 BR | 4 BA | Sleeps 8 | Quick View
Key Amenities
About this property
Venetian Shores 4-Bed/4-Bath Luxury Pool Home with 100' Dock & Opt. ElevatorMINIMUM STAY: 29 DAYS Dreaming of a Florida Keys vacation where you can boat, fish, dive, snorkel, or stay home and swim in your own private heated pool? This is it. This home offers a professionally-designed living environment ...
Property Type
Islamorada House
2 BR | 2.5 BA | Sleeps 6 | Quick View
Key Amenities
About this property
“Ocean Breeze” – This Beautiful Condominium Features an Ocean view, Protected Boat Slip, Tennis, Gym, and much, much more.New to the Vacation Rental market, this 2 Bedroom condo at Bay Harbour has been outfitted to make a Statement. Easy access to the Gulf or Ocean makes this ...
Property Type
Islamorada Condo
2 BR | 1 BA | Sleeps 4 | Quick View
Distance to beach: 5 miles to Five Miles
Key Amenities
About this property
Private, secluded villa faces Florida Bay in view of the fabulous Everglades. Located in a lush tropical hammock in a quiet residential area (rare). The villa is approx. 50 feet from the water. The property contains a wading beach and a free marina with night lights, power and water.The villa itself ...
Property Type
Islamorada House
4 BR | 4 BA | Sleeps 8 | Quick View
Key Amenities
About this property
This beautiful 4 bedroom/ 4 bathroom home has a 60' dock directly behind the home . Canal leads out to Snake Creek and has immediate Ocean and Bay access. The home is located in one of the finest neighborhoods of the Florida Keys- Venetian Shores. Upstairs there are 2 bedrooms/ 2 baths and there is a ...
Property Type
Islamorada House
2 BR | 2 BA | Sleeps 5 | Quick View
Distance to beach: 0.3 miles to Port Antigua Neighborhood Beach
Key Amenities
About this property
Minimum Rental: 28 Days"West Plaza Del Lago" promises to be a favorite. Beautifully remodeled roomy single family stilt home with vaulted ceilings and located in prestigious Port Antigua on a deep and wide canal. You will love the interior of this home as much as the exterior! As you enter ...
Property Type
Islamorada House
3 BR | 3 BA | Sleeps 6 | Quick View
Key Amenities
About this property
The MOSAIC HOUSE as it is named is located on one of Lower Matecumbe's (Islamorada) most popular streets and features a very unique floor plan. This home "lives" in the back of the house with glass walls overlooking a tropical paradise. There's an outdoor "play" area which includes ...
Property Type
Islamorada House
2 BR | 2 BA | Sleeps 6 | Quick View
Key Amenities
About this property
Minimum Rental: 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 offering you an opportunity ...
Property Type
Islamorada House
2 BR | 2 BA | Sleeps 4 | Quick View
Key Amenities
About this property
Minimum Rental: 28 Days"Beacon Reef 310" 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 yourself relaxing on your ...
Property Type
Islamorada Condo
2 BR | 2 BA | Sleeps 6 | Quick View
Key Amenities
About this property
Minimum Rental: 28 Days"The Palms #405" is 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 living ...
Property Type
Islamorada Condo
3 BR | 3.5 BA | Sleeps 8 | Quick View
Key Amenities
About this property
*******THIS PROPERTY IS NOT CURRENTLY AVAILABLE FOR RENT*******MINIMUM STAY: 28 DAYSFABULOUS BEACH HOUSE located directly on a mile long sandy beach. The original "Sea Grape" was destroyed by Hurricane Irma in September 2017. The decision was made to tear down and rebuild. The ...
Property Type
Islamorada House
4 BR | 3 BA | Sleeps 10 | Quick View
Key Amenities
About this property
This beautiful, four-bedroom, three-bath house is conveniently located in the heart of Islamorada, the fishing capital of the world. Situated in a beautiful upscale neighborhood of all waterfront homes, the house is equipped with all the comforts of home. It is extra clean and modernly furnished.Upstairs ...
Property Type
Islamorada House
4 BR | 4 BA | Sleeps 8 | Quick View
Distance to beach: 2 miles to Founders Park
Key Amenities
About this property
This tropical waterfront beauty has it all...heated pool, spa, dock, boat lift and custom elevator. It is beautifully appointed and fully equipped for your ultimate holiday rental. Located on a deep water canal, it has direct access to the Bay or Ocean. Enjoy unforgettable sunsets while relaxing on one ...
Property Type
Islamorada House
My wife and I have stayed at Irish Ayes the month of February the last three years. We love it there. This three story home has it all, pool, spa, boat dock even an elevator. The third floor master suite ...
2 BR | 2 BA | Sleeps 5 | Quick View
Key Amenities
About this property
Minimum Rental: 28 Days "The Palms #309" is an 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 kitchen ...
Property Type
Islamorada Condo
3 BR | 2.5 BA | Sleeps 6 | Quick View
Key Amenities
About this property
1st I want to thank all our past guests for their great reviews. Bay Harbour Starfish is a luxury condo overlooking a large boat basin with views of the Atlantic Ocean. Situated in Lower Matecumbe Key, Islamorada, the Sport Fishing Capital of the World. This very spacious 3 bedroom, 2 and half bath condo ...
Property Type
Islamorada Condo
4 BR | 2 BA | Sleeps 8 | Quick View
Key Amenities
About this property
4 Bedroom 2 bath home with private dock and private pool with direct open access to the ocean and convenient access to the bayside through Tavernier Creek. This is both family friendly and a fisherman's dream. Our home sleeps 8 (max) with every comfort you would want while on vacation in the keys...Large ...
Property Type
Islamorada House
3 BR | 2 BA | Sleeps 8 | Quick View
Key Amenities
About this property
Minimum Rental: 28 DaysHappy vacationing starts here! The owners call their special getaway “Bay Therapy” for many reasons. It is located in a great neighborhood in Key Largo. It is convenient to the mainland and is the gateway to the Keys. Since purchasing this home the owners have ...
Property Type
Islamorada House
2 BR | 2 BA | Sleeps 4 | Quick View
Key Amenities
About this property
Minimum Rental: 28 Days "The Palms #214" is a 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 panorama ...
Property Type
Islamorada Condo
3 BR | 2 BA | Sleeps 10 | Quick View
Key Amenities
About this property
Minimum Rental: 28 Days"Gulfview Getaway" is a FABULOUS BEACH FRONT HOME! This is what you've been dreaming of - your very own single family home with a private sandy beach in the Keys. This home is new to the rental market. It is located in a highly desirable area of Islamorada on ...
Property Type
Islamorada House
2 BR | 2 BA | Sleeps 6 | Quick View
Key Amenities
About this property
Minimum Rental: 7 DaysLittle Bay's Lower Duplex 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 month. Each unit sleeps up ...
Property Type
Islamorada House
1 BR | 1.5 BA | Sleeps 3 | Quick View
Key Amenities
About this property
Minimum Rental: 7 Days"Sunshine Place" is setup perfectly for 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 two people ...
Property Type
Islamorada House
My boyfriend and I stayed at The Sunshine Place to celebrate both of our November birthdays. I have been visiting the keys for many years and this is the best place I have found. The property was very ...
4 BR | 3 BA | Sleeps 10 | Quick View
Key Amenities
About this property
This gorgeous, newly constructed, Islamorada home has 4-bedroom, 3+ bath and is located in the quiet neighborhood of Venetian Shores MM86. It provides immediate access to both the Atlantic Ocean and Florida Bay via Snake Creek.The deep-water dockage is ideal for the avid boater or fishing enthusiast. ...
Property Type
Islamorada House
Four couples vacationed very comfortably in this Venetian Shores home. Kitchen is well planned, fully applianced, and spacious enough to allow all eight of us to enjoy meals together. Large patio with ...
2 BR | 2 BA | Sleeps 4 | Quick View
Key Amenities
About this property
Minimum Rental: 28 Days"Beacon Reef 222" is an 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 Islamorada. ...
Property Type
Islamorada Condo
3 BR | 3 BA | Sleeps 8 | Quick View
Key Amenities
About this property
Minimum Rental: 28 Days "Blue Water Retreat" is all about the location, location, location! This home has it all - ocean side Lower Matecumbe location, remodeled in 2009. Relax by the cocktail pool or sunbathe in the private roof top sunning area. There are blue water ocean views from ...
Property Type
Islamorada House
2 BR | 2 BA | Sleeps 4 | Quick View
Key Amenities
About this property
Minimum Rental: 28 Days"The Palms #407" is a charming 2 bedroom, 2 bath condo with updated kitchen and baths. Walk out onto your balcony and enjoy the sea breezes and ever changing ocean views. The comfortable furnishings and convenient floor plan provide an inviting place to call home. ...
Property Type
Islamorada Condo
1 BR | 1 BA | Sleeps 2 | Quick View
Distance to beach: 12 miles to Founders Park
Key Amenities
About this property
Secluded Waterfront Studio with Tiki hut, dock, King bed, 1 Bath, Sleeps 2.Please contact us for all of our rates for different length of stays! For shorter stays, make you have a minimum of 28 days entered in your contact form! We do not use the rate feature or the calendar feature on this listing. ...
Property Type
Islamorada Studio
Nice quiet little getaway. Enjoyed staying there. Has pretty much everything you need . Would rent there again.
2 BR | 2 BA | Sleeps 6 | Quick View
Key Amenities
About this property
Minimum Rental: 28 Days"The Palms #301" is an 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 sure ...
Property Type
Islamorada Condo
This unit had the most beautiful views. Sunrise from master bedroom and sunset from other bedroom. Units are centrally located on island which is an easy taxi ride or golf cart ride in either direction.
3 BR | 2 BA | Sleeps 6 | Quick View
Key Amenities
About this property
Escape to paradise in the fabulous Florida Keys at Futura Yacht Club. This rental property is a private gated community with a 65 slip deep water marina. This tropical waterfront community offers world class fishing and diving, 2 lighted tennis courts, heated pool, private beach, and dockage for your ...
Property Type
Islamorada Condo
My family and I had a great time in the Florida Keys this year. I have family that moved there in the last year or so and we wanted to visit. It was amazing!! We really had a great time and I was so happy ...
2 BR | 2 BA | Sleeps 6 | Quick View
Key Amenities
About this property
Minimum Rental: 28 DaysFlamingo Cottage is an adorable 3 bedroom stilt home nestled among tropical foliage. There are two bedrooms and one bath on the main living level of this home plus a private studio type apartment with a private bath on the ground level. This home has a cozy cottage like feeling ...
Property Type
Islamorada House
2 BR | 1.5 BA | Sleeps 4 | Quick View
Distance to beach: 0.5 miles to Anne Beach
Key Amenities
About this property
Island Conch Cottage A quaint ground level conch style cottage located at the end of a private street in a very quiet setting. Cottage and grounds have privacy fence and gate. The grounds are displayed as a sand beach setting. This property has 60’ of canal frontage located on an extra wide canal ...
Property Type
Islamorada House
This is the second time we stayed at this island conch Cottage, this is a beautiful home the neighborhood is very quiet and the locals are always friendly. We caught a variety of snapper just off the patio ...
5 BR | 4 BA | Sleeps 10 | Quick View
Key Amenities
About this property
Welcome to paradise! This home is a new listing. If you are looking for a large beautiful home with a pool in a peaceful setting and in an absolutely perfect location for your stay in Islamorada, you have found it! We are located in Venetian shores off Snake Creek with a boat slip for your use in the ...
Property Type
Islamorada House
3 BR | 2 BA | Sleeps 6 | Quick View
Distance to beach: 2000 feet to White Marlin
Key Amenities
About this property
Come visit Islamorada and enjoy a solar heated pool with Jacuzzi! You will also have access to a private homeowner's sandy beach! The sunsets are incredible! Come to paradise and relax in this Islamorada 3/2 with dockage. Bring your boat; you are just 20 minutes to the Atlantic and open Gulf. Everglades ...
Property Type
Islamorada House
2 BR | 2.5 BA | Sleeps 6 | Quick View
Key Amenities
About this property
2 Bed & 2.5 Bath Villa in Anglers Reef with Boat slip.Upscale gated community with resort living in the Florida Keys. Everything you need for your vacation is here: gorgeous private beach, heated resort style pool, private back yard patio with barbecue, front porch seating, upstairs balcony. Spacious ...
Property Type
Islamorada Villa
We loved our stay here. Location was great, home is nice and the property is very nice. This particular home backs to the busy highway so it can be a bit noisy especially when enjoying coffee on the back ...
1 BR | 2 BA | Sleeps 4 | Quick View
Distance to beach: 4 miles to Founders Park
Key Amenities
About this property
Bayside is a first floor apartment overlooking the water. Bayside is located on a small resort property nestled in a native hammock on Florida Bay. An easy 90 minute drive from Miami International Airport, this property is located in the heart of Islamorada, directly on Florida Bay. Bayside is fully air ...
Property Type
Islamorada Condo
1 BR | 1 BA | Sleeps 2 | Quick View
Key Amenities
About this property
The apartment is in house on the canal and across from the beach with beach access. It is situated on the ground floor of a two story keys house where you would be the only residents. All the amenities would be yours and you would have space, tranquility and privacy in the tropically planted landscape. ...
Property Type
Islamorada Apartment
2 BR | 2 BA | Sleeps 4 | Quick View
Distance to beach: 1 miles to Harry Harris
Key Amenities
About this property
Welcome to this 5th floor end unit condo in an art deco inspired building right on the Atlantic Ocean in a peaceful neighborhood. Enjoy full panoramic ocean views right from your own condo and balcony. Oceanfront clean heated pool and private covered parking space. Free high speed WiFi included. Sandy ...
Property Type
Islamorada Condo
My wife and I stayed here the first week in September, 2018 and wouldn't you know it, we got a tropical storm! It was just one rainy day however. This condo is on the 5th floor of a 7 story building, ...
3 BR | 3 BA | Sleeps 8 | Quick View
Distance to beach: 1 miles to founders park
Key Amenities
About this property
Located on the peaceful upper Keys, in Islamorada, licensed to rent weekly this home is situated in the quiet residential neighborhood of Venetian Shores MM 86. Immediate access to ocean and Bay side off of Snake Creek. Islamorada is just 75 miles from Miami and 86 miles from Key West. The average temperature ...
Property Type
Islamorada House
The house we rented was GREAT! It was on a canal- had a pool and was in a great location of Islamorada. It was clean when we arrived. The pool was clean as well. It has all the amenities anyone would need ...
