Islamorada Vacation Rentals

The Islamorada Village of Islands is situated between the saltwater wilderness of Everglades National Park in one direction and North America’s only coral barrier reef and the deep blue waters of the Florida Straits in the other. Owner Direct Vacation Rental has accommodations ranging from villas, to apartment rentals and condo rentals to satisfy all of your lodging needs.

Various vacation rental accommodations of either villa rentals or apartment rentals are located on one of the six islands that make up Islamorada. Stay in accommodation vacation rentals on the island of Plantation Key, Windley Key, Upper Matecumbe Key, and Lower Matecumbe Key. Accommodation of an apartment rental or villa rental can also be found on the offshore islands of Indian Key and Lignumvitae Key. Whichever island you choose you can be assured your accommodations will be first class.

The Islamorada area might be the only place on earth where it is possible to leave either your apartment rentals or villa rentals to catch a sailfish in the morning, and then venture into the backcountry in pursuit of bonefish, permit, tarpon, snook and redfish in just inches of water in the afternoon. With a fleet of highly skilled professional recreational fishing captains, Islamorada’s reputation as The Sport Fishing Capital of the World is well deserved.

Of course from vacation rentals there is much more to experience here in Islamorada then fishing. At Long Key State Park meander along lush, tropical nature trails. AtWindley Key Fossil Reef Geological State Park view an old quarry dug by the late Henry Flager’s railroad workers. At Lignumvitae Key Botanical State Park glimpse into Florida’s unique Island history dating back to the early 1800’s.

A trip to Islamorada would not be complete without sampling some of the local island cuisine headlined by succulent fresh seafood served everywhere from island tiki bars and dockside fish houses to gourmet beachfront cafes and secluded island bistros. All of which are located close to a number of villa rentals that are available. Shoppers will also be able to step out from their vacation rentals to enjoy many area boutiques and galleries filled with one-of-kind gifts, apparel and art.

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  • Islamorada Luxury Condo with 50' Private Boat Slip

    Islamorada Luxury Condo

    Islamorada: Bay Harbour: Condo in a gated community
    • 2 BDR
    • 3 BA
    • Sleeps 6
    • #209708
    avg $239 USD/night Paypal
    Escape to Islamorada in the Florida Keys and enjoy the breathtaking gulf and ocean views from your top floor balcony in this decorator furnished, two bedroom luxurious condo. This unit located in the complex of Bay Harbour offers a private 50' boat slip, heated swimming pool, hot tub, club house, fitness center, tennis courts, gas barbeque grills, tennis equipment, beach chairs and coolers. This spectacular condo offers two master bedrooms with private full bathrooms, additional half bath and full size washer and dryer. Additionally, each bedroom and the living room has flat screen televisions with cable tv. A dvd player is included in the living room. There is free wifi and telephone included for your use. The kitchen has stainless steel appliances, granite countertops and everything you need to prepare and serve a gourmet meal. The large balcony overlooking the water offers plenty of seating. Enjoy a meal or coffee while you take in the expansive views or enjoy the sunrise. Additionally, you will have a direct view of your boat parked in a private boat slip just steps away. Located at mile marker 75, this boater’s paradise is just minutes from fishing in the gulf or ocean, diving or snorkeling beautiful reefs, jet skiing, parasailing, kiteboarding or kayaking. Call to book your vacation of a lifetime.
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  • A Key Largo Escape

    A Key Largo Escape

    Key Largo: Villa
    • 9 BDR
    • 12 BA
    • Sleeps 30
    • #229913
    avg $4,500 USD/night Credit Card Pet Friendly
    This property is an amazing combination of natural beauty and stunning ambiance. From the tropical setting in one of Florida's most sought after destinations in the Key Largo Area, with private beach and dock, this is where the world ends and magic begins. Where else can you find a gated compound that sleeps 30 guests, within One main Estate and 6 Cabanas. The pristine beauty that lay just behind those magic gates takes you to a special place. Purchased 4 years ago by a private investor this compound was turned into a Sanctuary. Each Cabana is inclusive of it's own Master Suite and Guest sleeping arrangements on a one of a kind hidden Murphy Bed. Each Cabana sleeps 4 guests comfortably even while sharing. The rooms are modern and sleek with hidden treasures throughout, from the Bali Statues that line the property to the natural stone and elemental charm. These Cabanas are meant to soothe the mind. Each One Featuring a King Master and Guest Murphy Queen, One Beautiful full and one Half Bath. Great for families, friends or corporate gatherings. The Cabanas sleep 24 guests in total. The Estate House on property is a 3 bedroom and 5,000 Sq. Foot meeting area for the Sanctuary. It has a wonderful large living and dining area, 3 beautiful Bedrooms featuring 2 Master King Bedrooms and one 3rd Guest Suite with a Full and Twin Bed. This house sleeps 7 guests comfortably and has sleeping roll away beds for overflow. The bathrooms are magnificent and feature glass enclosures and free standing tubs, lovely granite and rain-showers, truly a place to escape the norm of the world around us. The Sanctuary is located just one hour south of Miami on the Gulf of Mexico side of Key Largo Island. The walled and gated estate ensures complete privacy and boasts a Sunset Pier, one of the only private piers in the Florida Keys. Apart from a wild flock of ibis or a passing dolphin, you and your guests can be the sole occupants of the entire sanctuary. It is life completely on your own terms with only the sun and the moon to advise you. Largo is an eco-friendly retreat, fully dedicated to sustainability and protecting the environment. The mission of the Family is to act as a guardian to this natural paradise, so that it will last for generations to come, and create a legacy to be enjoyed by their discerning guests. The Lagoon Pool is the focal point of our aquatic activities. Native coral boulders mold the shape of the pool, creating a free form that flows from our distinctive “walk-in” edge. The freshwater pool offers the pleasure of underwater therapeutic massaging jets while being conditioned by ultraviolet light for optimal cleanliness. Our Private Beach, with it’s calf-deep white sands imported from Florida’s West Coast, will lead you out to our Coral Lagoon. The 15 foot deep lagoon offers some of the best paddle boarding and kayaking in the Keys, and is adjacent to the Largo Sunset Pier. This unique gathering place rises from a foundation of natural coral to offer magnificent unobstructed sunset views in any season. The pier comes with generous appointments of power and audio to amp your party into the night. 3% Service Charge Pets allowed in one bungalow only Complimentary Morning Reception -- Coffee, Banana Bread, Croissants and Fruit (Served between 8:30AM and 10:00AM)
  • On the Ocean in Key West

    On the Ocean in Key West

    Key West: 1800 Atlantic: Condo
    • 2 BDR
    • 2 BA
    • Sleeps 5
    • #69125
    avg $288 USD/night Credit Card
    1350sq. ft. of fabulous living space located in a ocean front condo on the 2nd floor. Garden and partial ocean view from a 38ft private balcony accessible from the living and both bedrooms will make your vacation a memorable one and keep you coming back year after year. The property is decorated and managed / maintained by me personally assuring you of a memorable vacation in a property that is way above the average investor owned rentals offered by management companies. The average temperature is 77.8 degrees, making Key West the warmest city (average temperature) in the United States. It has never been below 41 or above 98 degrees.
  • Paradise in Marathon in the Beautiful Florida Keys !

    Paradise in Marathon in

    Marathon: House
    • 3 BDR
    • 2 BA
    • Sleeps 8
    • #203104
    avg $243 USD/night Paypal
    Diving, swimming and fishing all minutes from your private dock & garden patio, in the heart of the beautiful Florida Keys, 45 minutes to Key West & 15 minutes to one of the worlds few living reefs. This large private home has all the needs and comforts of home and then some, just bring your tooth brush. From the 42" DLP HD T. V, to walks on the world famous 7 Mile Bridge, no need for clocks here...You are in Paradise. Less than 10 miles to 3 State Parks an 1 mile to town Large Master bedroom with King Bed & Private Bath and tumbled marble double vanity. Sun Room with water view and Large Patio Set for your relaxation with lighted dock for night fishing. Fish from your private 50' Dock or Take a Dive at Sombrero Reef. Less than 15 min away.
  • Moon Bay Yacht and Tennis Club

    Moon Bay Yacht and Tennis

    Key Largo: Moon Bay Yacht and Tennis Club: Condo in a complex
    • 2 BDR
    • 2 BA
    • Sleeps 4
    • #13373
    avg $179 USD/night Credit Card
    This beautiful condo is on the fourth floor. There is an elevator in the building. Being on the fourth floor makes for a spectacular view from the screened in porch, living room, dining room, and master bedroom. Ceiling fans. Moon Bay has everything you need for a great vacation. There are free tennis courts, pool, saunas, a private boat slip,basketball hoop, and a dock for fishing and swimming to mention just a few of the amenities. There is a recreation room with ping pong and a water front grill. Wireless Internet.
  • 1726 Sq Ftwireless

    1726 Sq Ftwireless

    Marathon: Vacation Rental
    • 2 BDR
    • 2 BA
    • Sleeps 6
    • #226399
    Credit Card
    1726 sq ft Great view of the water. Beautiful two bedroom, two bath home in Marathon has a fantastic Gulf view and quick, easy access to open water. Very spacious, concrete dock, sundeck on top of home makes for spectacular sunrise and sunset scenes. Master bedroom has king bed with sitting area and full bath. Second bedroom has a queen size bed. Living area has a sleeper sofa. Spectacular views from living area and master bedroom. 7 night minimum stay
  • Bright Spacious Home on

    Bright Spacious Home on

    Key Colony Beach: Vacation Rental
    • 3 BDR
    • 2 BA
    • Sleeps 8
    • #226398
    Credit Card
    Bright, spacious home on canal with quick ocean access. Cabana Club privileges round out the Key Colony Beach experience.. This 2100 sq ft bright and spacious property is located just 3 houses back from the canal entrance to Shelter Bay, which provides quick access to the Ocean or Gulf. It also includes membership to the Cabana Club, which is oceanfront with a beach, heated pool, activities restaurant and bar. Key Colony Beach has walking and bike paths throughout the City, with golf, tennis, restaurants and charter boats nearby.
  • 1976 Sq Feet

    1976 Sq Feet

    Marathon: Vacation Rental
    • 4 BDR
    • 3 BA
    • Sleeps 10
    • #226397
    Credit Card
    1976 sq feet. Pool, hot tub. Wireless Comcast. Name is Marathon1 may need 305 in front Spectacular oceanview Single family home 4 Bedroom/3 bath high speed wireless internet central air conditioning washer/dryer dishwasher 150ft. Picture yourself on a tropical island, half-asleep in a poolside lounge chair of your own private home, with sun-kissed skies and the sparkling blue Atlantic Ocean nearby. Feel your body succumb to the tropcial breeze as it gently cascades over you, draining your stresses away. It is not a dream. It is life in Marathon, heart of the Florida Keys. In a recent review of tourist destinations around the world, Marathon was cited by the New York Times as one of the "Top 10 Hot Destinations for 2010! " Villa Tropical Dreams IS a tropical delight, full of ice cream colors and charm. This central air conditioning four bedroom deluxe home is completely private, there are no shared facilities, and it is only a five minute ride to the beautifully groomed Sombrero Beach. The master bedroom has its own en-suite bathroom with his and her sinks along with a king sized bed. It is equipped with a ceiling fan and cable television. The living area opens to the expansive porch overlooking the ocean with a grill to enhance your entertainment and cooking styles and the open floorplan leads an easy path to the fully equipped kitchen. Entertain and relax on the huge open covered deck, adjoining the large family room with glass on three sides. Sunbathe on the open deck, swim in the private pool, and relax in the hot tub. Sidewalk on tidal pool extends into the Atlantic for fishing or viewing. Drink your morning coffee to brilliant sunrises and cook fresh fish on the outdoor grill as the sun sets. World famous sport fishing - with 150 feet of concrete dock on deep-water canal. Oversized lot has plenty of room for parking, and bring your boat trailer. Some of the best scuba diving in the country is just off Sombrero Reef. SEVEN NIGHT MINIMUM STAY REQUIRED.
  • Wirelesscomcast for

    Wirelesscomcast for

    Marathon: Vacation Rental
    • 3 BDR
    • 2 BA
    • Sleeps 8
    • #226396
    Credit Card
    Wireless Comcast for TV 1575 Sq feet.. Escape to gorgeous Marathon, Florida Keys for a romantic getaway or a fun family retreat. For families with young children this Keys Vacation home is located just two blocks away from beautiful Sombrero Beach with a children`s playground, baseball diamond, volleyball net, picnic areas and roped swim area for all to enjoy. This fantastic single family home boasts open air decking while providing relaxation with a view. With table and four chairs seating to allow you to soak up plenty of sunshine while vacationing in the fabulous Florida Keys, or go down to the concrete dock area and lounge while watching an occasional visit by a manatee or a tarpon rolling by to say hello, it is sure to bring you plenty of flavorful memories. The light tropical decor of your rental is complete with glass sliding doors leading to a full deck overlooking the canal making it a combination both romantic and family-oriented. The engaging open floor plan with kitchen and dining table setup is perfect for entertaining whether cocktail party oriented or bringing the family together for a delightful mid-evening dinner at sunset. To complete this relaxing atmosphere, this home also features wireless DLS internet to accommodate your work needs while away. Docking - 40 foot concrete dock with additional space float dock to pull up your jet ski or small boat. The dock comes complete with a fish cleaning table to filet the catch of the day. Bedrooms: - Master bedroom with adjoining bath has a King size bed and a 39 inch flat screen tv. The 2nd bedroom features 25" TV with queen bed and 3rd bedroom has two twin beds and a 25" TV. The two guest bedrooms are conveniently separated by a guest bath. Bathrooms (2)- Large master bath has a walk in shower and a nice vanity. The other bath, with tub and shower head, is located in the hallway between the two guest bedrooms. Kitchen- A fully equipped kitchen that features lots of counter space and a breakfast bar that seats 4. There are lots of appliances for your convenience and enjoyment: side freezer refrigerator with ice maker; dishwasher; electric stove and microwave; coffee maker; blender; toaster and more. The Living room has a large leather couch for seating of approximately 9 and 42" television. The dining table is facing the water and seats eight with seating for four at the table level bar nearby. Parking- There is plenty of gravel parking to accomodate a boat trailer and 3 cars. Beach: - The house is approximately 3 blocksfrom beautiful Sombrero Beach. End canal location allows open wide canal water views and quick direct ocean access. City of Marathon SEVEN NIGHT MINIMUM STAY
  • Pool Heat extra3297 Sq

    Pool Heat extra3297 Sq

    Marathon: Vacation Rental
    • 4 BDR
    • 4 BA
    • Sleeps 10
    • #226395
    Credit Card
    Pool heat extra 3297 sq feet wireless password: 20ParkLane. Gorgeous, 4 bedroom, 4 full bath home, plus 1/2 bath, located on exclusive Tingler Island and near Sombrero Beach. This 3297 square feet tri- level floor plan provides space and privacy for visitors, while the softly lit pool area create a wonderful atmosphere for entertaining and relaxation. With over 1000 square feet of outdoor porches, you can enjoy relaxing on any of the balconies off every room or the hot tub overlooking the ocean on the third floor outdoors. If you need an even more breathtaking view, follow the spiral staircase to the fourth floor rooftop observation deck. The view is beyond spectacular. Then, take a casual stroll to the perfectly groomed Sombrero Beach, less than one mile away. This elegant home has plenty of parking for boat and jet ski trailers and a deep water canal that provides access to Sombrero Beach and the Atlantic Ocean in the blink of an eye. Both the gulf and ocean are accessible, with several boat ramps nearby. If you prefer a slower pace, take the kayak at the property and explore the mangroves and canals. The direct access to the ocean is perfect for fishing, diving, snorkeling and trips to the sandbar. It is also the best location for evening boat rides or visit one of our many restaurants where you can dock and dine. If you are renting over the 4th of July, THIS HOME IS IDEAL.. You don`t need to worry about beach parking, the fireworks look fantastic from the roof top deck, and your dock will give you the fastest access to the waters in front of the beach where many boats park for the day. Marathon is the ideal location for a Keys vacation. Located directly in the middle of the Florida Keys, nothing seems to be too far away. Spend an evening in Key West visiting the local haunts or watching the sunset at Mallory Square. Half way down, stop for a round of mini-golf at Boondocks, or go the opposite direction towards Key Largo and visit John Pennecamp State Park that is just 45 minutes away. 7 night minimum
  • 2600 Sq Ftpool Heat

    2600 Sq Ftpool Heat

    Marathon: Vacation Rental
    • 3 BDR
    • 4 BA
    • Sleeps 8
    • #226394
    Credit Card
    2600 Sq ft pool heat extra Wake up in your own sunrise paradise. Have coffee while sitting under your gazebo by the pool. This custom built, fully air conditioned, vacation home has all the amenities to make this the most memorable vacation you will ever experience. Very stylish, newly built, modern home of 2700 square feet, with 1000 of verandas, is located in the Coco Plum area with spectacular views overlooking the Atlantic Ocean. It is only a five minute ride to Coco Plum Beach. The three story home has been decorated with a light, spacious welcoming feel. It is equipped to ensure a perfect, relaxing and indulgent stay. There are three separate bedrooms and an additional room featuring TV and games which may be used as an additional (4th) bedroom for children or as a play room area. Prepare dinner in the very well equipped kitchen or eat at one of the area`s outstanding restaurants, many with dockage for your boating pleasure. 7 night minimum
  • 2700 Sq Feetpool Heat

    2700 Sq Feetpool Heat

    Marathon: Vacation Rental
    • 3 BDR
    • 4 BA
    • Sleeps 8
    • #226393
    Credit Card
    2700 sq feet pool heat extra Wake up in your own sunrise paradise. Have coffee while sitting under your gazebo by the pool. This custom built, fully air conditioned, vacation home has all the amenities to make this the most memorable vacation you will ever experience. Very stylish, newly built, modern home of 2700 square feet, with 1000 of verandas, is located in the Coco Plum area with spectacular views overlooking the Atlantic Ocean. It is only a five minute ride to Coco Plum Beach. The three story home has been decorated with a light, spacious welcoming feel. It is equipped to ensure a perfect, relaxing and indulgent stay. There are three separate bedrooms and an additional room featuring TV and games which may be used as an additional (4th) bedroom for children or as a play room area. Prepare dinner in the very well equipped kitchen or eat at one of the area`s outstanding restaurants, many with dockage for your boating pleasure. 7 night minimum
  • 2600 Sq Ftwireless Code

    2600 Sq Ftwireless Code

    Marathon: Vacation Rental
    • 3 BDR
    • 4 BA
    • Sleeps 8
    • #226392
    Credit Card
    2600 sq ft pool heat. Wake up in your own sunrise paradise. Have coffee while sitting under your gazebo by the pool. This custom built, fully air conditioned, vacation home has all the amenities to make this the most memorable vacation you will ever experience. Very stylish, newly built, modern home of 2700 square feet, with 1000 of verandas, is located in the Coco Plum area with spectacular views overlooking the Atlantic Ocean. It is only a five minute ride to Coco Plum Beach. This three story home has been decorated with a light, spacious welcoming feel. It is equipped to ensure a perfect, relaxing and indulgent stay. There are three separate bedrooms and an additional room featuring TV and games which may be used as an additional (4th) bedroom for children or as a play room area. Prepare dinner in the very well equipped kitchen or eat at one of the area`s outstanding restaurants, many with dockage for your boating pleasure. 7 night minimum
  • 14 Night Minimum Stay

    14 Night Minimum Stay

    Key Colony Beach: Vacation Rental
    • 2 BDR
    • 2 BA
    • Sleeps 4
    • #226391
    Credit Card
    14 NIGHT MINIMUM STAY. 14 NIGHT MINIMUM STAY Each unit is fully furnished and has two bedrooms, two bathrooms, dining area, full kitchen, washer/dryer, central heat/airconditioning and a private patio or balcony. This unit has a great corner view of the ocean. The kitchen is equipped with stove, refrigerator, dishwasher, utensils, cookware, glass selection and dishes.Linens and towels are also supplied. Cable TV is provided in each unit and on-site Internet wireless access is available at no additional charge. All of the condos are decorated according to the taste of the individual owners 14 night minimum stay per condominium association rules. 14 NIGHT MINIMUM STAY.
  • Lovely Home

    Lovely Home

    Marathon: Vacation Rental
    • 5 BDR
    • 4 BA
    • Sleeps 12
    • #226389
    Credit Card
    Lovely home on beautiful Coco Plum Beach with 100' of deep water dockage. This 5 bedroom, 4 bath home features high ceilings, all tile floors, granite and stainless kitchen and large screened porch overlooking the waterway. The master bedroom has a king tempurpedic bed and master bath wtih separate jacuzzi tub and shower. Two queen bedrooms also have the tempurpedic matresses, a trudle bed that makes into two twins is the 4th bedroom and the 5th has a double and a twin bunk. Occupancy for up to 12 people with plenty of room for all. Outside enjoy the pool and patio with plenty of seating and gas grill. Walk out to the 100' dock with 50 amp electric service if needed, fish cleaning talble and swim platform. There is a bait freezer and plenty of room to store your fishing and diving gear. A short walk down the bike path takes you to City-owned Coco Plum Beach. 7 night minimum stay

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