Florida Keys Homestays (91 properties)

This florida keys vacation rental home is secluded & private, on a peninsula of land surrounded by sea on all sides. Tucked away in total privacy abutting over Grassy Key harbor, with clear interrupted sea views, it’s still just a short drive away from the City of Marathon. The Open Water Views give this home a tranquil and secluded setting. Explore the bayside waters surrounding the house by 4 kayaks. Enjoy the complete private seclusion of an island, with all the conveniences of being on the mainland. It's a place of pelicans, egrets and cormorants. With the occasional iguanas and racoons that live there. Many varities of fishes, sea turtles and manatees live in these waters. You can hear the dolphins squeak and whistle as they play at the Dolphin Research Center, which is across the water from the peninsularhouse. Above all its a great place to relax on the sandy beach, or in the heated spa and pool.

Magnificent sunsets and views from a isolated eco-friendly environment. Located on quiet Big Torch Key just 30 minutes from Key West. Ideal for deep sea and back country fishing, snorkel and scuba diving in the amazing looe Key Reef. Excellent choice for Kayakers, bicyclists, water and nature lovers - We have it all! See a great variety of beautiful birds at environmentally protected wildlife sanctuary.Just a short 30 minutes drive to the beautiful Key West equipped with all the amenities and entertainment.

This property rents from Saturday to Saturday. Experience the tranquil Gulf waters of the Florida Keys from the unique perspective of your own floating home - docked at your own private tropical island. Your houseboat will be permanently docked at our private Island (aka Charlie's Island). You receive free exclusive use of our private tropical island for camping, picnicking, kayaking, snorkeling adventures and so much more. We provide a boat for transportation to and from your island. This worry free site is truly a get away from it all. This exposed fossilized ancient reef is beautifully landscaped with trails wandering throughout. You can enjoy wandering the paths through the mangrove trees, fishing from the docks, or snorkeling in the crystal clear waters around the island. We provide a grill and picnic tables for your tropical picnic as well as a hammock for the perfect perch to enjoy the tropical breezes off the Gulf waters. This is ideal for people who are interested in a rustic, camp like adventure! The island is located in a beautiful, quiet, private cove. There are no homes along the shoreline of the cove. The island is surrounded my mangroves from the south-western edge of Curry Hammock State Park.Your Florida Keys houseboat and island vacation adventure includes a 2 bedroom / 2 bathroom Houseboat which sleeps 5-6 guests. Our houseboats come fully equipped, offering you a safe and comfortable home base for your Florida Keys activities - the perfect place to kick off your shoes, lay back and relax.We will take time to familiarize you with your houseboat. As always, we are available to answer any questions you may have!Included:~ 2 Bedroom / 2 Bathroom Houseboat~ Exclusive Private Island Usage~ Motor Boat~ Spectacular view of the Gulf of Mexico~ Gas Generator~ Private and Secure~ Air conditioning~ AM/FM RadioKitchen (Galley) includes propane stove and oven, stainless steel sink, refrigerator, microwave, toaster & coffee pot as well as kitchenware.Rates are subject to change.

This property rents from Saturday to Saturday. This vacation rental package is perfect for large groups or multiple families who wish to vacation together, without sacrificing the benefits of private home rentals. Comprised of three adjacent Gulf front homes, for a total of 8 bedrooms, 6 bathrooms, 2 private docks, kayaks, 2 swimming pools. Conveniently located in the heart of the Florida Keys, this Gulf front location is ideal for pursuing a variety of interests, or simply enjoying the laid back ambiance that true Keys life is about.Amenities - 4 Bedroom, 4 Bath:Sleeping QuartersMaster Bedroom - Queen Size Bed, Patio Doors, TV, Exceptional View2nd Bedroom - Queen Size Bed, Private Entrance, Private Bath, TV3rd Bedroom - Queen Size Bed4th Bedroom - Double BedCreature Comforts Air Conditioning, Ceiling Fans, Satellite TV, DVD Player, Stereo with CD Player, Wireless InternetKitchen Fully Equipped Kitchen, Dishwasher, Microwave, Blender, Coffee Pot, Plates, Utensils, Glass Ware, Pots, Pans, Etc.Bed & Bath Toweling, Complete Bedding, Bath, Hand and Dish TowelsOutdoor (Land) Swimming Pool, Gas Grill, Decks with Patio Furniture,Outdoor (Sea) 100 foot dock, Kayaks, Fishing Gear & Snorkel Gear may be available upon request.Misc. Washer & Dryer, Iron & Ironing Board, Hair Dryer, Paper Products & Toilet Tissue, Parking for 2 Cars & 1 Boat TrailerAmenities - 4 Bedroom, 2 Bath:Sleeping QuartersMaster Bedroom - Queen Size Bed, Patio Doors, TV, Exceptional View2nd Bedroom - Queen Size Bed3rd Bedroom - Double Bed4th Bedroom - 2 Double Beds, TV, Private Outside EntranceCreature Comforts Air Conditioning, Ceiling Fans, Satellite TV, DVD Player, Stereo with CD Player, Wireless InternetKitchen Fully Equipped Kitchen, Dishwasher, Microwave, Blender, Mixer, Spices, Coffee Pot, Plates, Utensils, Glass Ware, Pots, Pans, Etc.Bed & Bath Towels & Linens.Outdoor (Land) Swimming PoolRates are subject to change.

This budget affordable, ocean side waterfront property, rents from Sunday to Sunday and is centrally located in the Florida Keys, features a host of amenities complete with vast views of the ocean. Conveniently located near Mile Marker 54 in Marathon Florida - also known as the Heart of the Keys - this private vacation rental is just a heart beat away from all the Keys has to offer. Contemporarily furnished, the home offers a nice open feeling with decorative tile throughout. Water enthusiasts can fish from the dock, swimming at one of the local beaches and much more. There is a huge deck for lounging under the sun, grilling out or just relaxing and taking it easy.Sorry there is no boat dockage space until after April 2013. Rates are subject to change.

The property rents from Saturday to Saturday. This beautifully landscaped property, centrally located in the Florida Keys, features a host of amenities complete with magnificent views of the Gulf of Mexico. Conveniently located on 121st Street, Gulf just past Mile Marker 54 in Marathon Florida - also known as the Heart of the Keys - this private vacation home is just a heart beat away from all the Keys has to offer.Contemporarily furnished in a comfortable Spanish style, the home offers a nice open feeling with decorative tile throughout. Water enthusiasts can choose between kayaking, snorkeling around the 100 foot private dock or lounging at the swimming pool. Families and large groups will love the large, open kitchen.This property is located adjacent to our 4 bedroom 2 bath location, which includes a private swimming pool. Rentals may be combined for an 8 bedroom, 6 bath rental - perfect for family reunions, large families, group vacations, weddings, and corporate retreats. Rates are subject to change.

This property rents from Sunday to Sunday. Welcome to your very own private tropical island only a few minutes from shore near Banana Bay Resort! Our 2 bedroom, 2 bath, private tropical island home is located in the tropical turquoise waters of the Gulf of Mexico off of Marathon in the Florida Keys. This beautifully furnished property features a host of amenities suitable for every taste, complete with panoramic views of the Gulf of Mexico extending from every room of this conch style island home.Exposed wooden beams adorn the living room's cathedral ceiling, complementing the home's wood and tile floors. French doors lead from the great room to a screened front porch and to a covered deck. Our fully equipped kitchen is complete with a breakfast bar. You can also make use of the outdoor gas grill. The master suite features a sunken Jacuzzi tub with 2 sided ocean view shower - the perfect way to end a day in paradise! All utilities (electricity and fresh water) are piped underwater from the mainland, supplying all the comforts of home in this secluded tropical paradise. Rental includes a small power boat intended for transportation between shore and island.Landscaped boardwalks surround the home for leisurely strolls around the island. This ancient fossilized exposed reef features native vegetation of silver buttonwood, black mangroves, sea grapes, and pitch apples which attract a vast variety of migrating and resident bird life. The crystal clear warm waters of this quintessential Keys location are occasioned by a variety of wild life including visiting dolphins, manatees, parrot and angel fish, roosting pelicans and great herons to name a few.Rates are subject to change.

This beautifully furnished vacation home rents from Saturday to Saturday and is centrally located in 'America's Caribbean' , the fabulous Florida Keys, and features a host of amenities suited for every taste! Our artistically landscaped waterfront home is located on a quite street in a pleasant neighborhood in Marathon close to restaurants and shopping.We provide a boat for transportation to and from your island. This worry free site is truly a get away from it all. This exposed fossilized ancient reef is beautifully landscaped with trails wandering throughout. You can enjoy wandering the paths through the mangrove trees, fishing from the dock, or snorkeling in the crystal clear waters around the island. We provide a grill and picnic table for your tropical picnic & to enjoy the tropical breezes off the Gulf waters. There are kayaks as well.The serene crystal clear warm waters of this Marathon Florida location are occasioned by a variety of wild life including visiting dolphins, sea turtles, manatees, parrot and angel fish, roosting pelicans, great herons to name a few - perfect for nature lovers and sport fishing enthusiasts. The property is fully furnished and decorated in open Mediterranean style, complete with Spanish tile throughout. The home itself is located on a quiet, dead-end street, near mile marker 52, and features no stairs for easy access. This rental includes a dock in your own back yard - on a waterway adjacent to the Gulf of Mexico, this is perfect location for a worry free vacation! Rates are subject to change.

This property rents from Saturday to Saturday. This vacation rental package is perfect for large groups or multiple families who wish to vacation together, without sacrificing the benefits of private home rentals. Comprised of three adjacent Gulf front homes, for a total of 12 bedrooms, 8 bathrooms, 3 private docks, 3 private swimming pools & Kayaks.Conveniently located in the heart of the Florida Keys, this Gulf front location is ideal for pursuing a variety of interests, or simply enjoying the laid back ambiance that true Keys life is about.Rates are subject to change.

This property rents from Saturday to Saturday or Sunday to Sunday. Rent your own private tropical island in the Florida Keys. Fanny Key is a private offshore island offering the ultimate island living experience, along with the ease and convenience of shore power and city water. Breathtaking gorgeous 360-degree open water views surround you. This prestigious island is 750 feet from the mainland. Our 4 bedroom, 2 1/2 bath, private tropical island home is located on 2 Acre's in the tropical turquoise waters of the Gulf of Mexico off of Marathon in the Florida Keys. This beautifully furnished property features a host of amenities suitable for every taste, complete with panoramic views of the Gulf of Mexico extending from every room, the rap around deck and even the roof deck. This tropical retreat comes with it's own private dockage on the mainland in Marathon, just minutes from the island. After you park your car, our ground's keeper will pick you up. Just hop in the 21' pontoon boat and drive out to the island. The island has 3 docks that all have water and electric. You will be the only guests in the only vacation home on the island. The island does come with a grounds keeper that keeps everything looking beautiful and the pool clean. He also run's 'Sunset Catamaran Trips' you may enjoy at a nice discount. This home has 3000 Square feet of living area and 5000 square feet overall. There are windows all around for amazing views. There is a champagne deck to watch the sunset from. You can also enjoy swimming in the private pool or just relaxing in the sun on the sun deck. Rates are subject to change

This property rents from Saturday to Saturday. This beautifully landscaped property, centrally located in the Florida Keys, features a host of amenities complete with magnificent views of the Gulf of Mexico. Conveniently located on 121st Street, Gulf just past Mile Marker 54 in Marathon Florida - also known as the Heart of the Keys - this private vacation home is just a heart beat away from all the Keys has to offer.Contemporarily furnished in a comfortable Spanish style, the home offers a nice open feeling with decorative tile throughout. Water enthusiasts can choose between kayaking, snorkeling around the 100 foot private dock or lounging at the swimming pool. Families and large groups will love the large, open kitchen.Rates are subject to change.

Gorgeous open water views await you at this fully furnished waterfront home that rents from Saturday to Saturday. Beautifully landscaped with a sandy backyard and a 9x19 ft private swimming pool, this choice Florida Keys location is centrally located in Marathon, 121st Street, Gulf is just past Mile Marker 54. A 100 foot private pier is complete with deep water docking for open water enthusiasts and serenity seeking vacationers or just lounge around at the swimming pool.This property is stylishly decorated with contemporary Spanish style furnishings and tile flooring throughout. Enjoy the exceptional views from the living and dining areas, or escape to the sandy yard & gulf shore through the master bedroom's patio doors. The fourth bedroom features a private entrance - ideal for group travel.Rates are subject to change.

Escape the bustling crowds of Florida by renting this spacious vacation rental in Islamorada for your vacation in Florida. A two bedroom two bath private house in a tranquil residential locality of Venetian Shores, this ocean view vacation rental in Islamorada, Florida is just steps away from the beach. Equipped with modern facilities like wireless high-speed internet, a desktop computer, TV in all rooms, DVD, Stereo, and a fully equipped kitchen, plus we have added a wime cooler in the kitchen, this vacation rental promises to make your holiday more enjoyable. With this rental, you have a kidney shaped swimming pool, all to yourself. So you can have fun in the pool all day, without having to abide by the timings of a community pool. The house overlooks a canal full of colorful fish like the Angel Sargeant Majors and Parrot fish. A private boat dock on the canal completes the setting for a relaxing holiday. The other features of this house are vaulted ceilings, a tiki bar near the pool which has four tall inviting chairs for you to relax in as you chill out with a drink from its small fridge, a queen size poster bed in the second room, and twin beds in the third bedroom and much more. A king-size bed and a living room are just some of the many things that grace the pool level Master suite. Located between the clear waters of the Florida Bay and the Gulf of Mexico, Islamorada is just 80 miles away from Key West and 75 miles from Miami. Three to five miles offshore is a coral reef which attracts an amazing variety of aquatic life. This vacation rental is located in the quiet, northern end of Islamorada, Florida. Vacation Rental License No VR-001

Rearing high against the sky and overlooking vast blue ocean, this colorful Key Largo Florida vacation rental offers breathtaking vistas of ocean-dominated landscape. This home is a pleasing hideaway for families and group of friends. Our big and spacious three storied 4 bedroom home rental Key Largo is wonderfully furnished and comes with a king-size bed, two queen-size beds, two twin beds, a twin trundle bed and a bunk bed to accommodate 12 vacationers comfortably. From the balcony of master bedroom, you can cherish filtered bay views. The three bathrooms are well fitted with showers and other basic amenities for your convenience. The capacious living room of this Key Largo vacation rental home features designer furnishings and entertainment facilities such as big screen TV, flat screen TV, cable TV, DVD and VCR. We also provide video games especially for children. The huge patio with full island kitchen, a barbecue and seating area, where you can relax and party together, overlooks the canal. Located just 45 minutes from Miami on a Canal which leads to the open bay waters of Largo Sound, our Key Largo oceanfront home offers you an opportunity to take pleasure in numerous water sports such as sailing, jet skiing, water skiing and parasailing. Visiting amusement parks such as Disneyworld – FL, Epcot Center, SeaWorld, Universal Studios and Busch Gardens with your family would be a memorable experience.

The Key Largo Lighthouse and Marina. It's what you’ve been looking for. For less than you spend on yet another hotel, your family can live on this very private 2 acre estate - directly on the Atlantic Ocean. You can sleep in this historic working lighthouse. Dock your mega-yacht in your own private marina. Bond with your family, have a barbecue together, catch a fish or catch some rays. All in the privacy of your own estate. And for your special event, you will turn Key largo Lighthouse & Marina into your party heaven. Exotic, yes. But You don’t need to break the bank traveling to some distant, hard to get to location. Your family will be living in the fabulous and famous Key Largo Florida, the diving and fishing capital of the world. Only 60 miles from Miami International Airport. And while this estate is very private, all modern necessities are nearby. Let’s start our tour out here by the “Oceanfront Esplanade”. People spend more time here than anywhere else. The sunrises are awesome. It is a huge area, about 10,000 square feet It is so immense it absolutely swallows large parties. People say it feels more like you are standing on a cruise ship than standing on land because it is almost surrounded by water. In the middle of the Esplanade is the Gazebo. It houses a complete bar with water and electricity. Sunbathing, barbecues and watching the boats sail by is the daily norm out here.Directly behind the Esplanade is the Mariana. Many people spend the entire day here fishing or swimming. There is excellent snorkeling right here against our sea walls and normally a lot of lobster hide under them. You are welcome to dock your boat or jet skis, or kayaks here. We can handle yachts up to 120 feet.This is the 8 foot wide gangway that connects the Esplanade with the other main entertaining area, the terrace. It is large enough to seat about100 guests. It is close to the main house and the kitchen so sometimes it is used for serving meals for large parties. It is completely covered by Palm trees. If there happens to be a lot of wind on the Oceanfront Esplanade, this is a more protected option for lunch or dinner.we join the main house. And on the other side of the main house is the entrance to the annex. The annex with three bedrooms, is connected to the main house but has a private entrance so the group staying here has a lot of privacy. Finally the lighthouse with its two bedrooms. I hope you get a chance to read the entire history of the lighthouse above. It is marked on all nautical charts and guides boats entering the canal every night. The best part of Key Largo Lighthouse and Marina are the accommodations. You will immediately realize you have privacy. Only an private estate can provide this type of seclusion. The accommodations are split in three separate very private areas, each with their own entrances: the main house, the annex, and the lighthouse for a total of 12 - 14 guests in 7 bedrooms. The Main Home features 2 king size suites with private bathrooms. The spacious modern kitchen is typically a focal point at meal times. There is ample and very comfortable living and dining areas. Adjoining the main home yet thru a separate entrance you’ll find the Annex. It is a very quiet area away from the party because the entrance is on the back of the house/ The Annex has two king size bedrooms, and one full size bedroom, plus one fold out sofa in an inviting living/TV area. Key Largo Lighthouse and Marina - the home of the “Wedding Without the Rush”. You have days to prepare for the wedding and days to unwind. Then, for the big event, how can it be any simpler. Your ceremony and reception are right here, where you and your guests are living. You create your own wedding. Imagine. If you decide you want help, there are wedding planners, caterers, photographers, all with experience on this property. You get to choose exactly what you want your w

Welcome to your very own private tropical island only a few minutes from shore! Our 2 bedroom, 2 bath, private island home is located in the tropical turquoise waters of the Gulf of Mexico off of Marathon in the Florida Keys. This beautifully furnished property features a host of amenities suitable for every taste, complete with panoramic views of the Gulf of Mexico extending from every room of this conch style island home.Exposed wooden beams adorn the living room's cathedral ceiling, complementing the home's wood and tile floors. French doors lead from the great room to a screened front porch and to a covered deck. Our fully equipped kitchen is complete with a breakfast bar. You can also make use of the outdoor gas grill. The master suite features a sunken Jacuzzi tub with 2 sided ocean view shower - the perfect way to end a day in paradise! All utilities (electricity and fresh water) are piped underwater from the mainland, supplying all the comforts of home in this secluded tropical paradise. Rental includes a power boat. Landscaped boardwalks surround the home for leisurely strolls around the island. This ancient fossilized exposed reef features native vegetation of silver buttonwood, black mangroves, sea grapes, and pitch apples which attract a vast variety of migrating and resident bird life. The crystal clear warm waters of this quintessential Keys location are occasioned by a variety of wild life including visiting dolphins, manatees, parrot and angel fish, roosting pelicans and great herons to name a few. We also have many other homes that we rent including up to 12 bedroom 8 bath accomodations.Rent My LCC is licensed by the city of Marathon to do vacation rentals. We follow all city and state regulations for our properties. The PLR number for Pretty Joe Rock- PLR2010-00128

Experience the tranquil Gulf waters of the Florida Keys from the unique perspective of your own floating home - docked at your own private tropical island. Your houseboat will be permanently docked at our private Island (aka Charlie's Island). You receive free exclusive use of our private tropical island for camping, picnicking, kayaking, snorkeling adventures and so much more. We provide a boat for transportation to and from your island. This worry free site is truly a get away from it all. This exposed fossilized ancient reef is beautifully landscaped with trails wandering throughout. You can enjoy wandering the paths through the mangrove trees, fishing from the docks, or snorkeling in the crystal clear waters around the island. We provide a grill and picnic tables for your tropical picnic as well as a hammock for the perfect perch to enjoy the tropical breezes off the Gulf waters. This is ideal for people who are interested in a rustic, camp like adventure! The island is located in a beautiful, quiet, private cove. There are no homes along the shoreline of the cove. The island is surrounded by mangroves from the south-western edge of Curry Hammock State Park.Your Florida Keys houseboat and island vacation adventure includes a 2 bedroom / 2 bathroom Houseboat which sleeps 5-6 guests. Our houseboats come fully equipped, offering you a safe and comfortable home base for your Florida Keys activities including free use of kayaks for your stay - the perfect place to kick off your shoes, lay back and relax. We also have a variety of other homes we offer that feature up to 12 Bedrooms and 8 Baths. We even have private island homes.

The visual drama of romantic sunsets and mesmerizing panoramic ocean vistas unfolds and adds to your delight as you begin your holiday at East Sister Rock Island, a Marathon, Florida vacation rental. Privately owned, 1/4 mile off the shore in Florida Keys, this beautiful island is built on a coral reef 3 bedroom rental home can comfortably accommodate up to eight. The plush bedrooms include a king-size bed, queen-size bed, one double bed. The bathrooms are well appointed as per modern standards. A fully equipped kitchen is also there to cater to your culinary desires and there is a gas barbeque grill to gather over sizzling cookouts while enjoying the endless views and the spectacular sunsets.For your entertainment, this Marathon vacation rental home features flat screen TVs along with satellite, DVD and CD/Stereo players to catch up with your favorite movies, shows and music. There is a pool table as well for couple of games of 8 or 9 balls. You can also revel in the private pool of our Marathon vacation home. You can simply relax and enjoy the secluded tropical charm of the island and don’t miss out on the sun climbing out of the ocean in the morning and sink to the most spectacular sunset. Your beloved pets are more than welcome at this pet friendly Marathon rental home.The Island is surrounded by a coral reef and thereby makes it an ideal base to indulge in fishing, snorkeling, diving, swimming, etc. Between the island and the mainland you will come across pods of permit and bonefish. World renowned tarpon fishing at the Seven Mile Bridge is only a five minute boat ride to the west. To the south lies the Gulf where the deep sea anglers can battle sailfish, dolphin, marlin and Wahoo. Swimming with the dolphins is just 45 minutes away and there is a dolphin museum nearby.

This beautifully furnished vacation home is centrally located in 'America's Caribbean' and includes free use of your very own private island and free use of kayaks, and features a host of amenities suited for every taste! Our artistically landscaped waterfront home is located on a quite street in a pleasant neighborhood in Marathon close to restaurants and shopping. We provide a boat for transportation to and from your island. This worry free site is truly a get away from it all. This exposed fossilized ancient reef is beautifully landscaped with trails wandering throughout. You can enjoy wandering the paths through the mangrove trees, fishing from the dock, or snorkeling in the crystal clear waters around the island. We provide a grill and picnic table for your tropical picnic & to enjoy the tropical breezes off the Gulf waters. There are kayaks as well.The serene crystal clear warm waters of this Marathon Florida location are occasioned by a variety of wild life including visiting dolphins, sea turtles, manatees, parrot and angel fish, roosting pelicans, great herons to name a few - perfect for nature lovers and sport fishing enthusiasts. The property is fully furnished and decorated in open Mediterranean style, complete with Spanish tile throughout. The home itself is located on a quiet, dead-end street, near mile marker 52, and features no stairs for easy access. This rental includes a dock in your own back yard - on a waterway adjacent to the Gulf of Mexico, this is perfect location for a worry free vacation! We also offer many other homes, houseboats and motor boats for rent. We have accomodations for up to 30 people, up to 12 bedrooms.

This beautifully furnished vacation home is centrally located in 'America's Caribbean' , the fabulous Florida Keys, and features a host of amenities suited for every taste! Our artistically landscaped waterfront home is located on a quite street in a pleasant neighborhood in Marathon close to restaurants and shopping. The serene crystal clear warm waters of this Marathon Florida location are occasioned by a variety of wild life including visiting dolphins, sea turtles, manatees, parrot and angel fish, roosting pelicans, great herons to name a few - perfect for nature lovers and sport fishing enthusiasts. The property is fully furnished and decorated in open Mediterranean style, complete with Spanish tile throughout. The home itself is located on a quiet, dead-end street, near mile marker 52, and features no stairs for easy access. This rental includes a free powerboat which docks in your own back yard - on a waterway adjacent to the Gulf of Mexico, this is perfect location for a worry free vacation! Rent My LCC is licensed by the city of Marathon to do vacation rentals. We follow all city and state regulations for our properties. The PLR numbers (Property License and Registration Numbers) for all of our properties are listed below:Pretty Joe Rock- PLR2010-00128, 6th Avenue/ Dolphin Jump Key- PLR2010-00397, Sandy Shore Place- PLR2012-00387, Gulf View Place- PLR2012-00386, Ocean View Villa- PLR2012-00385