Key Largo Vacation Rentals

Key Largo is a gorgeous island in the upper Florida Keys archipelago. Accommodation in Key Largo is highly esteemed, as the condo rentals, vacation rental homes, and vacation rentals are all breathtaking. Key Largo is considered the Diving Capital of the World, and a hotspot for scuba divers and water-sport enthusiasts alike. With the Everglades so close, Key Largo is also a great place for kayakers and ecotourists as well. Accommodation and lodging near the beaches is recommended, especially if it is a condo rental or a vacation rental, although, alternative accommodations are also available.

Key Largo offers much in the form of entertainment. Dolphin Plus offers children seven and older a chance to learn and interact with dolphins. The Key Largo Scuba Shack is considered one of Key Largo’s best scuba diver shops, allowing you to dive in one of the best diving spots in the world, with free guides on your trips. While diving, do not miss Spiegel Grove, the remains of a ship that had sunk and was uplifted by Hurricane Dennis. There is also the Marine Lab Undersea Laboratory, which offers a variety of underwater and educational activities for the family. There is also the opportunity to go parasailing on the gorgeous waters near the Gulf of Mexico. Key Largo is also one of the only places to find a living coral barrier reef, which makes scuba diving here that much more unique. When booking accommodations in Key Largo, it is recommended to book in advance. And, remember, with Owner Directs Last Minute Deals, you may find vacation rentals or other accommodations at a significantly discounted price!

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3 Vacation Rentals

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  • 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
    $128 to $228 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.
  • This 2br/2ba with Canal

    This 2br/2ba with Canal

    Key Largo: Vacation Rental
    • 2 BDR
    • 2 BA
    • Sleeps 7
    • #238387
    $185 to $198 USD/night Credit Card
    This 2BR/2BA with canal access has a private dock for boats up to 35’. Savor a cocktail in the shade of the backyard tiki hut, and soak in the hot tub while watching a movie on one of two flat screen TVs. Bonus bedroom in the finished garage.. Make the most of the Key Largo sunshine in the home’s outdoor oasis. You’ll feel cool and comfortable on the warmest summer days with a misting system that provides invigorating refreshment and controls mosquitos. Relax with friends under the shaded tiki hut or unwind with a soak in the hot tub. Mixologists, try your hand at new cocktails in the beach-themed outdoor bar. With two flat screen TVs, you can watch films from the hot tub or the bar. A private dock with access to the Gulf accommodates boats up to 35’. A high-tech boat lift with remote control makes raising, lowering, and storing your boat a breeze. ABOUT THE HOUSE The second-floor living room, kitchen, and dining area are bright and comfortable. The living room has a leather sectional with seating for four, a perfect spot to put your feet up and catch a movie on the 51” TV. Just outside your door, a private outdoor oasis awaits. Beach-lovers will adore the tiki hut, with a sitting area, hot tub, and two flat screen TVs. Barbecue on the propane grill and dine at the outdoor dining table, then cap your evening with a refreshing cocktail prepared at the outdoor bar. Or make meals in the well-equipped kitchen to enjoy at the dining area for four. After dinner, step out onto the balcony to enjoy views of beautiful Key Largo. The second-floor master bedroom is a welcoming retreat with a queen bed, walk-in closet, and 41” TV. A bathroom with walk-in shower is conveniently located adjacent. On the first floor, the guest bedroom sleeps three with a twin-over-full bunk bed. An en-suite bathroom and 31” TV make this a private hideaway perfect for kids. For larger groups, a bonus bedroom in the finished garage sleeps an extra three guests on a twin inflatable mattress and full-size Murphy bed. Amenities include a washer/dryer in the garage. There is ample driveway parking for four cars. For fishing enthusiasts, a freezer in the garage keeps your catch fresh. THE LOCATION This Key Largo home is perfect for sailors, equipped with a dock for boats up to 35’ and a remote-controlled boat lift. The open waters of the Gulf of Mexico are a short sail away. View underwater sights while snorkeling at John Pennekamp Coral Reef State Park, less than a 10-minute drive from your door. Paddle or kayak through the Everglades for a true Key Largo experience.
  • This 4br/3ba Key Largo

    This 4br/3ba Key Largo

    Key Largo: Vacation Rental
    • 4 BDR
    • 3 BA
    • Sleeps 6
    • #242718
    $353 to $584 USD/night Credit Card
    This 4BR/3BA Key Largo home is a water lover’s paradise with boat slip, kayaks, and a stand-up paddleboard. Go for a dip in your private pool and hot tub, whip up a recipe in the outdoor kitchen, and gather around the backyard fire pit. Sleeps 6.. Welcome to Manatee Manor. Find paradise at this newly remodeled 2,100 square foot 4BR/3BA vacation home, set on the canal in Key Largo. With spacious interiors, an expansive backyard, and indoor/outdoor kitchen and dining areas, there’s plenty of room for six people. Spend your days poolside with a cool drink in hand. Enjoy indulgent soaks in your private hot tub, or make use of the kayaks and standup paddleboard provided. Bring along your boat and tie off at the private dock for craft up to 37’ in length. This exceptional home offers 120’ of water frontage. Watch for glimpses of marine life from your dockside palapa, or go exploring in Everglades National Park and the coral barrier reef. ABOUT THE HOME Inside, the gourmet kitchen boasts granite countertops, well-stocked cabinetry, and a full suite of stainless steel appliances. Grab a seat at the breakfast bar for four, or dine together at a sleek wood table. Mix a cocktail at the granite bar with wine fridge and ice maker, and get comfortable in the living area, furnished with a plush sectional and matching sofa and a 55” flat screen TV. Outdoors, spend quiet mornings on the canal with the kayaks or standup paddleboard provided for you. Or launch your own boat from the private dock. Prefer to lounge on land. Soak up the sun from a chaise recliner, then cool off with a dip in the custom in-ground swimming pool with spa and waterfall. When you’ve worked up an appetite, prepare a family recipe in the full outdoor kitchen, complete with a fridge, sink, stove, and gas grill. Dine at the patio table for six, then toast marshmallows at the fire pit and have s’mores for dessert. At night, drift to sleep in your king-size master bedroom with 50” flat screen TV and a charming window seat. Your en-suite master bath features a dual vanity, walk-in shower, and a walk-in closet. The second king-size bedroom offers handsome wood furnishings, its own 40” flat screen TV, and two closets. The third bedroom offers two full-size beds. Watch your own 32” TV, and unpack your bags in two generous closets. The fourth bedroom has a king-size bed. Check your emails in the private workspace, watch shows on the 37” wall-mounted flat screen TV, and enjoy direct access to the pool area and patio. The adjoining guest bathroom has a walk-in shower. Just off the main entrance of the home is the third full bathroom with tub/shower combination. Guest amenities include complimentary Wi-Fi, Nintendo Wii, and a washer/dryer. Parking is available for up to four cars in the driveway. All leases require a minimum 31-day term. THE LOCATION Known as the Diving Capital of the World, Key Largo is home to exotic marine life, crystal clear waters, and beautiful white-sand beaches, Key Largo offers no shortage of ways to spend time outdoors. Bring along your boat to experience firsthand North America's only coral reef. Explore Everglades National Park to spot manatees, alligators, and birds. Hop in the kayaks we’ve set aside for you, and paddle along the canal. Or take to the waters by standup paddleboard and keep an eye out for fish swimming near the surface. Taste local seafood at Lazy Lobster, a 6-minute walk from your door. And afterward, indulge your sweet tooth with a fresh cone from Mr. C's Homemade Ice Cream (7 minutes on foot). Drive straight to your rental and access the home with your unique lock code. When you book, we will send you our mobile app with directions and home instructions. We’re available 24 hours a day with live help. Each reservation includes applicable taxes, cleaning fee, and Property Damage Protection policy.
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  • On the Ocean in Key West

    On the Ocean in Key West

    Key West: 1800 Atlantic: Condo
    • 2 BDR
    • 2 BA
    • Sleeps 5
    • #69125
    $245 to $405 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.
  • Executive Bay 2 / 1.5 - Great Location. Great Unit!

    Executive Bay 2 / 1.5

    Islamorada: Executive Bay Club: Townhouse in a gated community
    • 2 BDR
    • 2 BA
    • Sleeps 4
    • #234599
    $164 to $171 USD/night Paypal Star Rating
    Come to Paradise and Enjoy it with Comfort. Located on Mile Marker 87 in Islamorada ( Fishing Capital of the World ), part of the Wonderful Florida Keys. Executive Bay Club is a Private Gated Community with 24 Hr Security, Heated Pool and Club House, Tennis Courts, Private Beach, Fishing off your own Dock and incredible sunsets. Our Two Story Unit is nicely decorated and furnished, Granite Kitchen counter tops, stainless steel appliances , complete with everything you need. Large Living Room and Dining Room with large flat panel LCD TV , and Outside Patio with a relaxing atmosphere. Master Bedroom (Queen Size Bed) plus a Loft, Second Bedroom Has 2 Twin Size Beds, Full Bathroom upstairs, Half Bathroom on the first floor. This unit is in a great location, across the pool, clubhouse and steps to the beach and fishing pier.
  • 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
    $243 to $343 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.
  • Newly remodeled home in

    Newly remodeled home in

    Marathon: Vacation Rental
    • 3 BDR
    • 3 BA
    • Sleeps 6
    • #242078
    $549 to $799 USD/night Credit Card
    Newly remodeled home in The Florida Keys with 3 bedrooms and 3.5 bathrooms. Located within a private yacht club with boat slips available for rent as well a centrally located clubhouse and pool area complete with top-notch amenities.. Marlin Bay Yacht Club is a newly remodeled private community located within Marathon, Florida in the heart of The Florida Keys. As you drive through the elegant gates of the property you are welcomed by an exquisitely decorated 2-story clubhouse. As you enter the clubhouse you are greeted by our accommodating concierge team who is more than eager to assist you in planning a trip of a lifetime. The clubhouse features numerous amenities for you to enjoy during your stay, including a full-service bar, a state-of-the-art fitness center, a yoga studio, sauna, steam room, billiards, shuffleboard, multiple big screen TVs, and beautifully appointed lounges for you to relax and spend time with your family and friends. As you walk through the clubhouse and step outside you are immediately taken back by the incredible views that The Keys have to offer. Here you will find a lovely lagoon style pool, a relaxing whirlpool, modern lounge furniture to enjoy the warmth, and a full-service tiki bar. Beyond this remarkable resort-like atmosphere we also feature a private 99-slip marina complete with an experienced dockmaster to prepare you and your vessel for an amazing sea excursion. Even if you do not plan to boat during your time with us, the clubhouse, the pool area and the dramatic 3-story residences are certainly designed to please all guests and provide you with luxury accommodations. Our 3-bedroom homes are fully furnished, professionally decorated, and feature an open floorplan. As you enter the ground floor from your 2-car garage you will find a lovely master bedroom complete with its own full bathroom and private patio. As you ascend onto the second floor you will find a state-of the-art gourmet kitchen which seamlessly flows into modern dining and living areas. On this level you will also find another private deck overlooking the beautifully landscaped pool area and a conveniently placed half bathroom. Last but not least, as you arrive on the third floor you will discover an additional master bedroom complete with its own full bathroom, wet bar, and private balcony. The third bedroom is also located on this level with 2 twin beds and a private bathroom as well. If the multiple levels concern you, there is no need to worry as our homes include elevators so you can easily access each floor.
  • Perched on the Largest

    Perched on the Largest

    Marathon: Vacation Rental
    • 4 BDR
    • 3 BA
    • Sleeps 10
    • #240137
    $320 to $632 USD/night Credit Card
    Perched on the largest deep water canal in the Florida Keys, this fresh 4BR/3BA home offers a large boat dock, a glittering pool, and both a fish cleaning station and a dedicated freezer. Newly updated with ceramic tile floors and mermaid décor. Sleeps 8.. Relish in emerald canal views at this lovely 4BR/3BA Key Colony Beach home, complete with a spacious waterside deck and sparkling private pool. New wood-grain ceramic tiles line every room, with fun mermaid accents greeting you at every turn. Bring your boat along or rent one nearby to make use of your large, private dock. Anglers will appreciate the fish cleaning station and dedicated freezer. ABOUT THE HOUSE New ceramic tile lines the floors of your freshly updated home, with playful mermaid décor lighting up each room. The open-concept living room boasts a massive sectional couch and a recliner for movie nights and TV marathons on the 55” flat screen TV. White appliances and cabinetry gleam in the kitchen, where expansive granite counters make meal prep a breeze. Find all the gadgetry and cookware you could dream of to fix simple beach picnics or elaborate dinners. Six can sit down to breakfast at the sweeping breakfast bar, with room for eight in the elegant formal dining area. Step out to the patio to find outdoor dining, sun loungers, and a full outdoor living room set. Slip into the pool for a relaxing swim among emerald canal views. Make use of the barbeque grill, along with your large private dock and a dedicated fish cleaning station. There’s also a standalone freezer for storing your catch inside. The king-size master bedroom offers a 42” TV and a pristine en-suite bath with a double-sink vanity and a tiled walk-in shower. The second and third bedrooms both have cozy queen-size beds and a shared en-suite bath with a walk-in shower, and the fourth has two twin-size beds. Another full guest bath is equipped with a tub/shower combination. Extras at the house include driveway parking with room enough for a small RV, a washer/dryer, and complimentary Wi-Fi. THE LOCATION Your Florida Keys home has it all — a private dock on the canal and South Beach's sand, sun, and surf within half-mile from your door. Rent a rig at Miami Five Star in 7 blocks, and dine on everything from pizza to tacos Mediterranean steps away.
  • All Photos, Amenities, Calendar,

    All Photos, Amenities

    Marathon: Vacation Rental
    • 3 BDR
    • 2 BA
    • Sleeps 8
    • #241323
    $204 to $530 USD/night Credit Card
    All photos, amenities, calendar, and rates are 100% accurate. We will notify you proactively when early check-in / late check-outs are possible and you'll receive the comforts of home with a starter supply of shampoo, soaps, paper products and hotel-quality towels and linens. And we make it easy to stay with us. Drive straight to your rental and access the rental with a unique lock code that we give only to you. When you book, we will send you our mobile app with directions, lock code, and instructions. We’re available 24 hours a day with live help. All vacation rentals follow local and state tax rules. Each reservation includes applicable taxes, a cleaning fee, and a Property Damage Protection policy.
  • All Photos, Amenities, Calendar,

    All Photos, Amenities

    Marathon: Vacation Rental
    • 3 BDR
    • 2 BA
    • Sleeps 6
    • #241322
    $226 to $598 USD/night Credit Card
    All photos, amenities, calendar, and rates are 100% accurate. We will notify you proactively when early check-in / late check-outs are possible and you'll receive the comforts of home with a starter supply of shampoo, soaps, paper products and hotel-quality towels and linens. And we make it easy to stay with us. Drive straight to your rental and access the rental with a unique lock code that we give only to you. When you book, we will send you our mobile app with directions, lock code, and instructions. We’re available 24 hours a day with live help. All vacation rentals follow local and state tax rules. Each reservation includes applicable taxes, a cleaning fee, and a Property Damage Protection policy.
  • Newly remodeled home in

    Newly remodeled home in

    Marathon: Vacation Rental
    • 3 BDR
    • 3 BA
    • Sleeps 6
    • #242079
    $549 to $799 USD/night Credit Card
    Newly remodeled home in The Florida Keys with 3 bedrooms and 3.5 bathrooms. Located within a private yacht club with boat slips available for rent as well a centrally located clubhouse and pool area complete with top-notch amenities.. Marlin Bay Yacht Club is a newly remodeled private community located within Marathon, Florida in the heart of The Florida Keys. As you drive through the elegant gates of the property you are welcomed by an exquisitely decorated 2-story clubhouse. As you enter the clubhouse you are greeted by our accommodating concierge team who is more than eager to assist you in planning a trip of a lifetime. The clubhouse features numerous amenities for you to enjoy during your stay, including a full-service bar, a state-of-the-art fitness center, a yoga studio, sauna, steam room, billiards, shuffleboard, multiple big screen TVs, and beautifully appointed lounges for you to relax and spend time with your family and friends. As you walk through the clubhouse and step outside you are immediately taken back by the incredible views that The Keys have to offer. Here you will find a lovely lagoon style pool, a relaxing whirlpool, modern lounge furniture to enjoy the warmth, and a full-service tiki bar. Beyond this remarkable resort-like atmosphere we also feature a private 99-slip marina complete with an experienced dockmaster to prepare you and your vessel for an amazing sea excursion. Even if you do not plan to boat during your time with us, the clubhouse, the pool area and the dramatic 3-story residences are certainly designed to please all guests and provide you with luxury accommodations. Our 3-bedroom homes are fully furnished, professionally decorated, and feature an open floorplan. As you enter the ground floor from your 2-car garage you will find a lovely master bedroom complete with its own full bathroom and private patio. As you ascend onto the second floor you will find a state-of the-art gourmet kitchen which seamlessly flows into modern dining and living areas. On this level you will also find another private deck overlooking the beautifully landscaped pool area and a conveniently placed half bathroom. Last but not least, as you arrive on the third floor you will discover an additional master bedroom complete with its own full bathroom, wet bar, and private balcony. The third bedroom is also located on this level with 2 twin beds and a private bathroom as well. If the multiple levels concern you, there is no need to worry as our homes include elevators so you can easily access each floor.
  • We Guarantee all Listing

    We Guarantee all Listing

    Marathon: Vacation Rental
    • 2 BDR
    • 2 BA
    • Sleeps 10
    • #243237
    $229 to $420 USD/night Credit Card
    We guarantee all listing information is accurate and up to date. From the moment you book, you’ll be provided timely and helpful communications regarding your trip. Upon arrival, easily access your home with a keyless secure door code; no need for an in-person key exchange. Your rental will be professionally cleaned and ready for you to enjoy. You can expect all comforts of a fine hotel, including shampoo, soaps, paper products, towels, and linens. Your home will include a HomeDroid tablet (electronic guest directory) providing specific home details, local suggestions, Wi-Fi access, TV instructions, and more. If you need anything at all before, during, or after your stay, our 24/7 local team is always ready to help!
  • Across the Bay from

    Across the Bay from

    Islamorada: Vacation Rental
    • 3 BDR
    • 2 BA
    • Sleeps 8
    • #241141
    $390 to $782 USD/night Credit Card
    Across the bay from the Everglades National Park, this 3BR/2BA waterfront home features a private beach, dock, kayak, and paddleboards. You’ll also love being near John Pennekamp Underwater State Park for premier diving. Sleeps 8.. Situated on the beautiful Florida Bay, this 3BR/2BA Islamorada home offers an idyllic waterfront haven with its own private beach, dock, kayak, paddleboards, and sprawling backyard with a volleyball net. Spend leisurely afternoons fishing off the dock before cooking up your catch on the grill. Enjoy your meal at the six-person patio table, then relax in one of two sun loungers. Or enjoy spectacular sunsets from the waterside hammock. Conveniently located, this home sits across the bay from the entrance to Everglades National Park. Nestled between Snake and Tavernier Creek, you’ll also be close to premier snorkeling and diving at Pennekamp Underwater State Park -- just 15 miles away. ABOUT THE HOUSE This home features a welcoming open floor plan with cool, tiled flooring and an abundance of natural light. After a day of fishing or diving, kick back in the main living area with a couch, love seat, and oversized chair. Enjoy your favorite shows on the 65” flat screen HDTV. Find more space to unwind in the adjacent sunroom, furnished with a couch, love seat, and two inviting armchairs. Play a board game or a round of cards at the four-person glass top table. It’s easy to whip up meals in the spacious kitchen, equipped with high-end appliances. A three-person kitchen bar offers a casual spot to chat while the chef preps dinner. In the dining area, there’s room for six to enjoy meals amid spectacular sunset views across the bay. With sleeping space for up to eight, this house features three bedrooms, each equipped with an AIR CONDITIONING unit to ensure a good night’s sleep. The master bedroom includes a stately king-size bed and a large closet. Across the hall, another king bed awaits in the second bedroom, which also has a large closet and a convenient office nook. Guests in these rooms share a bathroom with a walk-in shower. In the third bedroom, you’ll find two twin-over-full bunk beds and a Jack-and-Jill bathroom (shared with the sunroom) with a walk-in shower. Outside, the tropical backyard provides a direct view of the Florida Bay as well as its own private beach. This outdoor retreat has it all: a full-size sand volleyball court, outdoor dining, a charcoal grill, a fire pit, and a private dock with outdoor seating. Additional guest amenities include complimentary Wi-Fi, cable TV, a washer/dryer, and parking for four cars in the driveway. All leases require a minimum 31-day term. THE LOCATION Within a 30-minute drive, John Pennekamp Coral Reef State Park offers some of the best diving in the U.S. Along with superb snorkeling, sailing, and glass-bottom boat tours. Spend the day exploring the park’s 70 nautical square miles of Atlantic Ocean waters, or head across the bay to enter the Everglades National Park for wildlife sightings and thrilling swamp tours. For more outdoor adventures, swim with dolphins at Theater of the Sea (an 8-minute drive), and hit the hiking trails in Windley Key Fossil Reef Geological State Park (6 minutes). When dining out, head to Marker 88 for a laid-back beachfront grill specializing in seafood and cocktails. Or go for craft beers and hamburgers at MEAT Eatery & Tap Room. Both are within a 7-minute walk.
  • 14 Night Minimum Stay

    14 Night Minimum Stay

    Key Colony Beach: Vacation Rental
    • 2 BDR
    • 2 BA
    • Sleeps 4
    • #226391
    $171 to $200 USD/night 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.
  • Situated in an Exclusive

    Situated in an Exclusive

    Key West: Vacation Rental
    • 3 BDR
    • 3 BA
    • Sleeps 6
    • #242177
    $243 to $543 USD/night Credit Card
    Situated in an exclusive gated enclave, this brand-new 3BR/3.5BA offers a private elevator, patio, five balconies, and community pool access. Located in the heart of Key West, the Old Town district boasts great shopping, dining, and entertainment. Sleeps 6. PROPERTY OVERVIEW Situated in the exclusive gated enclave of Old Town Villas at Key West, this stunning brand-new 3BR/3.5BA townhome offers a private elevator, patio, five balconies, and community pool access. Relax in one of two living rooms with large HD TVs, or simply watch the sun set from the private terrace in your bedroom. Located in the heart of Key West, the Old Town district boasts epic shopping, dining, and entertainment. LIVING AREAS This luxurious townhome is designed to blend classic Key West style with modern upscale comforts. The inviting open-concept downstairs living room has ample seating, a 55” HD TV, and balcony access, while the upstairs family room offers a 55” HD TV, a wet bar with a wine fridge, and a large balcony with a table seating for five. An upstairs study is a great place to read or check emails. Step out onto the rooftop balcony to enjoy the marina views. KITCHEN & DINING The chef in your group will appreciate the gourmet kitchen with high-end stainless steel appliances, expansive granite counters, a double sink, glass-top range, and bar seating for four. When it’s time to eat, gather around the dining table with seating for six. BEDROOMS & BATHS Find quiet privacy in the master bedroom with a stately king bed, a spacious walk-in closet, a private balcony, and a 48” HD TV. Refresh in the en-suite bathroom with a double vanity, a jetted soaking tub, and a walk-in shower with a rainfall showerhead. The junior master bedroom boasts a king bed, walk-in closet, private balcony, 32” HD TV, and an en-suite bathroom with a walk-in shower. The third bedroom provides two twin beds, a 42” HD TV, two closets, and an en-suite bathroom with a walk-in shower. A half bathroom is located on the top floor off the second living room. OUTDOOR AREAS Kick back on the ground floor patio, enjoy some personal time on one of two private balconies, or watch the sun set from the rooftop terrace. Spend sun-drenched afternoons at shared year-round (unheated) pool, then gather your party for an al fresco meal on the top story balcony with a table and chairs for five. EXTRA AMENITIES & DETAILS Perks include complimentary Wi-Fi, a private in-home elevator, and a washer/dryer. On-site parking is limited to one car in the garage; additional paid parking is available nearby. All leases require a minimum 31-day term. THE LOCATION When dining out, visit local favorite Michael’s Restaurant for American dishes and fondue offered in a sophisticated atmosphere with a garden patio and outdoor bar. Or check out Caroline’s Cafe for po' boys and conch fritters in a circa-1838 house with outdoor seating. Take a five-minute walk to the Key West Aquarium which features a touch tank for hands-on experiences, plus free guided tours. Upon arrival, easily access your vacation home with a keyless secure door code; no need for an in-person key exchange. Your rental will be professionally cleaned and ready for you to enjoy. You can expect all comforts of a fine hotel, including shampoo, soaps, paper products, towels, and linens. Your home will include a HomeDroid tablet (electronic guest directory) providing specific home details, local suggestions, Wi-Fi access, TV instructions, and more. If you need anything at all before, during, or after your stay, our 24/7 local team is always ready to help!
  • Soak in Water Views

    Soak in Water Views

    Marathon: Vacation Rental
    • 3 BDR
    • 3 BA
    • Sleeps 8
    • #238859
    $215 to $358 USD/night Credit Card
    Soak in water views on the sun-kissed rooftop terrace of this 3BR/3BA home. Enjoy a master suite oasis with luxurious jetted tub and private deck. Keep your boat at your fingertips with plenty of dock space for rent nearby. Sleeps 8.. Mariners will find this 3BR/3BA home the perfect retreat after a day on the water. Dock your boat nearby at one of the many spots available for rent, and then stroll back to the house to rest and recharge. You’ll feel on top of the world as you gaze over the clear waters of Florida Bay from the comfort of your 700-square-foot rooftop terrace, furnished with plenty of comfortable chairs, sofas, and recliners. End your day in the tranquil master suite. After a glass of wine or a nightcap on your private balcony, enjoy a soak in the jetted tub or a movie on the flat screen TV. ABOUT THE HOUSE For the ultimate movie night, gather your group in the spacious living area on the second floor and play your favorite films on the 55” flat screen TV. A sofa and love seat offer seating for five. Discerning chefs will appreciate the kitchen’s stainless steel GE appliances and dishwasher. Enjoy meals at the dining table for six or on the balcony with views of the neighborhood. Unwind in the first-floor master suite with a queen bed, walk-in closet, and 40” TV. The en-suite bath will be your oasis; rinse off in the walk-in shower or soak in the jetted tub. The private deck with a bistro set is perfect for enjoying coffee or a romantic cocktail for two. The second bedroom, located on the first floor, includes two twin beds, a 26” flat screen, and an en-suite bath. On the second level, the versatile third bedroom contains a queen bed and a queen-size futon to use as seating or sleeping accommodations for two. On the second-floor balcony, you’ll find a spiral staircase leading to your expansive private roof terrace. Lounge on recliners and soak in the sun, or gather your group in the shaded seating area to enjoy games, conversation, and panoramic bay views. Plan a barbecue on the shaded patio beneath the house, equipped with a gas grill and a dining area for eight. Two parking spaces are available, and you’ll find a washer/dryer on the first floor. THE LOCATION Take advantage of well-kept shared amenities. Lounge by the pool and enjoy sweeping bay views while you swim, or head down to the docks, where boat owners can rent bayside space to store their vessel. Idyllic Sunset Park Beach is just a 5-minute drive from your door. Florida Keys Aquarium Encounters, less than a half mile away, is perfect for a family-friendly afternoon of snorkeling and discovering marine life.
  • Located in Old Town

    Located in Old Town

    Key West: Vacation Rental
    • 1 BDR
    • 1 BA
    • Sleeps 3
    • #238465
    $88 to $146 USD/night Credit Card
    Located in Old Town, this restored 1920s conch house apartment is classic Key West. Near Duval Street, beaches, and the historic seaport. Just a short walk to dining and shopping. Enjoy access to a heated pool. Sleeps 3.. Enjoy a classic Key West vacation at this charming 1BR apartment in a restored 1920's conch house. This prime Old Town location is just a short walk from Duval Street, the historic seaport, beaches, dining, and one-of-a-kind shops. Guests enjoy use of the heated pool. ABOUT THE APARTMENT This light-filled, open-concept apartment has vaulted ceilings and inviting relaxation spaces. Enjoy a movie in the comfy living room, with a queen-size sleeper sofa and 37” flat screen TV. Cook your meals in the well-equipped kitchen, with a convenient island with seating for two. The bright dining space accommodates four. Take a dip in the shared heated pool, or sit out on a private porch and enjoy the cool shade provided by the surrounding palm trees. A bubbling fountain in the front yard welcomes you to the property. The bedroom has a plush queen-size bed and a full bath. Amenities include a washer/dryer. And there is open street parking available for one vehicle. THE LOCATION A plethora of local attractions are nearby. Southernmost Point and the Ernest Hemingway museum are both an 8-minute drive from the house, while famed Duval Street is less than a mile away. There are plenty of walkable restaurants, shops, and attractions on Fleming Street, so you never have to go far to have a great time.
  • Kick off your Sandals

    Kick off your Sandals

    Islamorada: Vacation Rental
    • 2 BDR
    • 2 BA
    • Sleeps 4
    • #238432
    $193 to $345 USD/night Credit Card Pet Friendly
    Kick off your sandals and get into full vacation mode—this 2BR/2BA Islamorada house is the ideal home base for your relaxing getaway. Enjoy a quiet private beach. Walk to restaurants and bars. Sleeps 6.. Straight from the pages of a travel magazine, this 2BR/2BA Islamorada house commands a prime location overlooking the jewel-toned waters and white sands. Inside, bright sunshine comes in through multiple sliding glass doors, bathing the open spaces in natural light. Start and end your day out on the screened balcony. When it’s time for a night out, you’re just a short walk from great restaurants and bars. The heart of Islamorada is just 8 miles away. The area is also known for outstanding snorkeling and scuba diving. ABOUT THE HOUSE Take in the panoramic views from the screened balcony that spans the front of the house. Curl up with a book on the patio couch, and dine al fresco at the four-person table, enjoying warm breezes and the sound of the waves. Tasteful beach decor and neutral colors create an inviting ambiance in the living room. Settle into the couch to watch the 39” flat screen TV, or just kick back and enjoy beautiful ocean views through the sliding glass doors. Pack lunches for the beach and make inspired dinners in the well-equipped kitchen. Sit down to meals around the dining table for four. Two bedrooms sleep six comfortably. Slumber in the master bedroom’s king bed, and enjoy plenty of storage in the walk-in closet and several dressers. Take in the water views through the sliding glass doors. An en-suite bathroom offers a tub/shower combination. Guests will love the views from the second bedroom, featuring two full beds, a large closet, and sliding glass doors out to the balcony. The en-suite bathroom has a tub and shower combination. There’s parking underneath the home for one car with additional two spots in the driveway. Other amenities include an outdoor shower and a laundry room with washer/dryer. THE LOCATION Known as the “Village of Islands,” Islamorada (8 miles away) is brimming with natural beauty and lots to see and do. Get up close and personal with dolphins at the Theater of the Sea, browse the exhibits at the History of Diving Museum, and explore the Windley Key Fossil Reef Geological State Park. The area offers exceptional scuba diving and snorkeling, which you can do on your own or hire a professional guide for a tour. The Caloosa Cove Resort is a 15-minute walk away and has a full-service marina and island store. Treat yourself to dinner out at one of the nearby restaurants. Local favorites include Habanos, which offers oceanfront dining, and the Safari Lounge for an after-dinner nightcap.
  • Located around the Corner

    Located around the Corner

    Key West: Vacation Rental
    • 3 BDR
    • 3 BA
    • Sleeps 6
    • #239593
    $293 to $720 USD/night Credit Card
    Located around the corner from Key West’s bustling Petronia Street and Restaurant Row, this 3BR/3BA home boasts a chef’s kitchen with upscale appliances and granite countertops, as well as a private heated pool and tropical deck. Sleeps 6.. Affectionately known as the Captain’s Quarters, this two-story custom-built 3BR/3BA is located on a quiet lane in Bahama Village. This lovely neighborhood exudes a charming old Key West vibe. Step out to your backyard for a dip in the private pool, set amid lush landscaping, and enjoy meals at the outdoor dining table for four. Located three blocks from Duval Street, and just around the corner from lively Petronia Street and Restaurant Row, you’ll find everything from Caribbean eats to crepes to kosher fare, mere steps from your door. You’re also near an array of eclectic independently-run boutiques. ABOUT THE HOUSE Step through the sliding glass doors off the living room to swim in the crystal-clear heated pool with a unique waterfall feature. Linger over al fresco meals among lush tropical gardens. The open-concept living area seats five between a plush sofa and chair; enjoy a 46” flat screen Apple TV and Sonos theater system. The chef’s kitchen makes cooking a pleasure with its granite countertops and stainless-steel appliances that include an oven with warming drawer, and a Thermador four-burner stove with griddle and grill. Enjoy coffee at the kitchen island with seating for three, or dine at the four-person table. When it’s time to turn if for the night, you’ll find a bedroom with two twin beds and a 37” flat screen TV just off of the entryway. A bathroom with a walk-in glass shower sits adjacent. Upstairs, the second bedroom features a queen bed, 37” flat screen TV, walk-in closet, and bathroom with walk-in shower. Down the hall, the master bedroom has a queen-size bed, 42” flat screen TV, walk-in closet, and a luxurious en-suite bathroom with double-sink vanity, large jetted tub, and a separate shower with dual showerheads. Two double doors off the master bedroom lead to a balcony. Guest amenities include complimentary Wi-Fi, Apple TV, a washer/dryer set, and parking for two cars. All leases require a minimum 31-day term. THE LOCATION Situated on a quiet lane in Bahama Village, your rental home is around the corner from many of Key West’s favored restaurants and shops. Traveling with kids. You’re a short drive from the Key West Aquarium and the Mel Fisher Maritime Museum. Have literature lovers in your midst. The Ernest Hemingway Home and Museum is blocks away. And the beach is a 5-minute drive.

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