Home Vacation Home Rentals By Owner In Summerland Key, FL

Showing 100 Of 116 Vacation Rentals
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Exceptional(1)

$493.85

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Private Vacation Home

Starlight Serenity - Hideaway with Stunning Views

Summerland Key, Florida, United States

Summary:brbrEscape to paradise at this serene 1-bedroom, 1-bath home in beautiful Sugarloaf Key sleeping up to four guests. Enjoy breathtaking views from the expansive wrap-around balcony, perfect for sunrise coffee or sunset cocktails. The spacious outdoor area is ideal for dining, lounging, and soaking in the tropical ambiance.brbr Whether you're relaxing indoors or savoring the outdoors, this home offers the perfect blend of comfort and tranquility.brbrbrbrBook your next getaway for 3 nights or more!brbrbrbrThe Space:brbrWelcome to your perfect getaway! This charming home features a spacious open-concept floor plan designed for relaxation and connection. The main living space includes two twin sleeper sofas, while the bedroom features a queen bed - making it ideal for families or groups of friends.brbrbrbrNatural light pours into the airy interior, complementing the seamless flow between the living, dining, and kitchen areas. Whether you’re enjoying quiet moments or gathering for meals, this inviting space offers the comfort and convenience you need for a memorable stay.brbrbrbrBedroom 1: Queen Bed brbrExtra sleeping: two twin sofa beds in living roombrbrbrbrGuest Access:brbrOur contactless check-in procedure makes check-in easy. Guests will receive a personalized access code prior to arrival.brbrbrbrHow to access: Stair access onlybrbrbrbrThe Neighborhood:brbrStarlight Serenity is located on Sugarloaf Key, just 19 miles from Key West. This private oasis is conveniently situated right off US-1.brbrbrbrCheck out our favorite must-do activities and eateries, all within 5 minutes of your front door:brbrbrbrLooking for a day away Visit Sugarloaf Lodge, where you can take a boat to the South of Seven Restaurant & Marina.brbrBook a day on the water! Enjoy local fishing, eco tours, kayaking, paddleboarding, snorkeling, and more.brbrSeeking adventure Experience the trip of a lifetime at Sky Dive Key West.brbrSavor local flavors. Dine at local favorites like Square Grouper and My New Joint.brbrCoffee lover Vacation isn’t complete without a great brew. Check out Morning Joint and Baby’s Coffee for your morning fix!brbrbrbrGetting Around:brbrParking Information: Private parking is available in front of the home.brbrbrbrThis home is conveniently located, offering easy access to everything Sugarloaf Key and the surrounding Keys have to offer but still maintaining peacefulness surrounded in nature. A car is recommended for exploring the area, with ample parking available at the property.brbrbrbrEnjoy a short drive to nearby beaches, marinas, and local attractions. Key West, with its vibrant nightlife, unique shops, and historic sites, is just a 25-minute drive away. For those looking to explore by bike or foot, the scenic Overseas Highway provides stunning views and plenty of spots to stop and take in the beauty of the Keys.brbrbrbrOther Things to Note:brbrPrivate Washer/Dryer: Conveniently located in the home.brbrParking Information: Private parking is available in front of the home.brbrPet-Friendly Home: Dogs under 25 lbs are welcome! $15 per night, per pet, Maximum of 2 petsbrbrThis property is a 3-night minimum stay.
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Bath 1

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Sleep 4

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Exceptional(1)

$655.26

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Private Vacation Home

Oceanfront Gated Corner lot Amazing Sunsets. 90” BoatDock & 12 person Swim Spa!

Summerland Key, Florida, United States

Vista de Sirenas translates to ‘Mermaid Views’ is a piece of paradise with an unobstructed sunset view over open water year round! 3,200 sq ft living space on oversized fenced corner lot at the very end of a private road offering picture perfect sunsets! Boasting 323' of water frontage, this property includes 175' of open water and 148' of canal frontage featuring a 90' concrete dock, and a private kayak launch. brbrThe main level of the home features a wrap-a-round deck, a spacious living area, including a large master bedroom and bathroom, 2nd bedroom, half bathroom and a large kitchen area. The third level has a private bedroom, bathroom and balcony accessible by a spiral staircase. On the opposite side of the home is a private mother-in-law/teen suite with an open floor plan that includes a large living area, 2 Story tongue & groove West Indies Great room with wet bar and it's own kitchen with views for days!brbrWe have a 12 person Calspa Swim Spa with Vertical massage plus benches for up to 12 people, 55 jets, surround sound and open year round along with outdoor couches, pool table, lounge chairs and grill to complete the outdoor living! The entire property is pricacy fenced & Gated!brbrWe have plenty of toys including Kayaks, Fishing Rods, Paddle Boards, Bike cruisers, a pool table and plenty of inside games also. Boat Dockage is super with room for up to 42 ft boat plus a floating Jet Ski Dock that holds 2 Skis! We have boat rentals available also! Plenty of parking for all the guests! Easy access with super fishing spots and reefs! brbrOnly 20 mins to Key West with plenty of shopping, Nightlife and super restaurants. Check out our Instagram page for reviews! @vistadesirenasbrbrThe best of all is the wide open water & gorgeous sunset views! We searched for the right property for three years for our family to enjoy. We hope you love it just as much as we do!
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Bath 3

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Sleep 10

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$273.21

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Private Vacation Home

Summerland Canal-Front Escape w/ Plunge Pool, Dock, Tiki Bar, WiFi & Laundry

Summerland Key, Florida, United States

Boasting a canal-front location, this two-bedroom home is a dream retreat on Summerland Key. Tie up a boat of up to 24 feet at the private dock. Cruise the canal with ease, travel mere minutes to prime fishing and diving locations, and come home to take a dip in the backyard plunge pool and sip tropical drinks in the festive tiki lounge.br brKick back in the sunny living area after a fun-filled day, where a large sectional sofa provides comfortable seating and the 32-inch Smart TV offers streaming capability. Home chefs will appreciate the modern kitchen, newly appointed with a full suite of stainless steel appliances and granite countertops. When it's time to eat, you can share home-cooked meals around the table for four in the dining area.br brThe wrap-around balcony offers space to bask in the sun or relax in the shade. Unwind on the covered back patio, take a refreshing dip in the private plunge pool, make use of the gas grill for an afternoon cookout, and enjoy a tropical retreat to the covered tiki bar. Additional amenities include free WiFi, a washer/dryer, and driveway parking.br brFrom fishing equipment to boat rentals, retailers along Overseas Highway provide all the gear you'll need for aquatic adventures. You'll also find several local eateries in the area, conveniently located about a mile from home. For a beautiful beach day, travel 13 miles to Bahia Honda State Park.brbrThings to KnowbrFull kitchenbrAccess to this stilted home is via a flight of external stairsbrThere is a 28-night minimum staybrThis canal-front home is located across the street from the Summerland Key Cove Airport. While the private airport receives little traffic, passing airplanes may occasionally be heard.br brThis property is managed by Seven Keys Vacations by Casago.
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Bath 1

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Sleep 5

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$269.2

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Private Vacation Home

Water Lovers Paradise

Summerland Key, Florida, United States

brThis newly renovated vacation home on a canal in Cudjoe Key is a stunning retreat that offers the perfect blend of comfort, relaxation and adventure. brbrThe living room is furnished with plush sofas and chairs, a large flat-screen TV, making it the perfect spot to unwind after a long day of boating or exploring Key West. The kitchen is fully equipped with new stainless steel appliances, quartz countertops, with French doors that open to a screened in deck overlooking the water if you prefer to dine al fresco. brbrThe home has four spacious bedrooms, two with their own private en-suite bathroom. The bedrooms are tastefully decorated and feature comfortable beds, high-quality linens, and plenty of storage space.brbrOne of the best features of this vacation home is its outdoor living space. The home is in a quiet residential neighborhood and sits right on the water, and there is a deck that overlooks the canal and Cudjoe Bay. The deck is furnished with comfortable outdoor furniture, making it the perfect spot to enjoy your morning coffee or watch the sunset.brbrThere is also a private sixty foot concrete dock with a fish cleaning table that can accommodate boats, making it easy to explore the surrounding waters with easy access to either to gulf or the ocean. Other amenities include a chest freezer for bait, a full size washer and dryer, high-speed internet, two bicycles and two paddle boards. Key West, Bahia Honda state park, Looe key marine sanctuary, Cudjoe gardens marina, bait shops, several restaurants and grocery stores are all close by. Square grouper, a top rated restaurant and lounge is walkable. brbrOverall, this newly renovated vacation home on the water in Cudjoe Key is the perfect place to escape from the hustle and bustle of everyday life and enjoy a vacation of a lifetime. brbr**MINIMUM 28 NIGHT RENTAL** *TENANT IS RESPONSIBLE FOR UTILITIES (WATER AND ELECTRICITY) DURING THEIR STAY.
Bed 4

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Bath 2

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Exceptional(5)

$544.25

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Private Vacation Home

The Blue Pearl: Spacious Open Water Retreat, Stunning Sunsets, Boat Bar, Room for Everyone & Fido!

Summerland Key, Florida, United States

County zoning requires a minimum rental period of 28 nights, and no exceptions can be made. Please review additional policies below. brbr brbrWelcome to 'The Blue Pearl' – the ultimate destination for large families or multiple families seeking an expansive and accommodating retreat! brbr brbrWith two distinct living areas, this spacious haven offers ample room to gather together or find your own space for relaxation. Step onto the sand and revel in the 125 feet of oceanfront that's all yours. Watch the breathtaking sunsets paint the sky with vibrant hues. As the day transitions to evening, gather around the Boat Bar, where tales are shared and favorite cocktails savored. While 'The Blue Pearl' offers a wealth of activities, if you're itching to explore the Keys, Key West is just 25 minutes away, and Marathon is a short 40-minute drive. Your ideal vacation awaits at 'The Blue Pearl.' Secure your reservation now and embark on a journey of relaxation, adventure, and the splendor of the Florida Keys! brbr brbrSLEEPS MAXIMUM OF 12 GUESTS: brbr brbrBedroom 1 (2nd Floor): King Bed, En-Suite Bathroom, Smart TV (no cable/satellite TV) brbr brbrBedroom 2 (2nd Floor): Queen Bed, Smart TV (no cable/satellite TV) brbr brbrBedroom 3 (1st Floor): Queen Bed brbr brbrBedroom 4 (1st Floor): Queen Bed & Twin Bed, Smart TV (no cable/satellite TV) brbr brbr2nd Floor Loft: Three Twin Beds brbr brbr2nd Floor Living Room: Sectional Sofa, Two Chairs, 75 Smart TV (no cable/satellite TV) brbr brbr1st Floor Living Room: Sofa, 65 and 55 Smart TV's (no cable/satellite TV) brbr brbrTwo Kitchens: Nicely equipped (all things necessary to prepare and serve a meal) brbr brbrAMENITIES: brbr brbr- 65' of Private Dockage brbr brbr- Private Boat Ramp to launch up to a 22' boat brbr brbr- Fish Cleaning Station brbr brbr- Outdoor Seating brbr brbr- Tournament Size Pool Table brbr brbr- Parking for a maximum of 4 vehicles, including boat trailers. Recreational Vehicles may not be parked on the property. brbr brbr- Linen's and towels provided brbr brbrIMPORTANT POLICIES FOR YOUR STAY: brbr brbrAge & Occupancy: The booking tenant must be 25 years or older and must occupy the property for the entire duration of the stay. This property is exclusively available as a vacation rental and not for worker housing. brbr brbrPeak Season Monthly Bookings: All bookings from December through March must be for the entire month, starting at the beginning and ending at the end of the month. Consecutive months may be booked if they follow this requirement. Bookings that do not adhere to this policy are subject to cancellation. If you are interested in alternative dates, please contact us for approval before booking. brbr brbrPet Policy: Up to two friendly and well-behaved dogs 50 LBS or less will be considered with a $10/night pet fee. To help maintain a safe and welcoming environment for all, we require every guest to submit pet or assistance animal information through BetterPet Passport. Guests will simply submit household pet information, request an accommodation for an assistance animal, or confirm they are not bringing a pet/animal. It's free, and only requires creating an account if you're bringing a pet or animal. After booking, you'll receive a link to complete the process. brbr brbrSmoking Policy: Smoking is strictly prohibited to maintain a smoke-free environment. brbr brbrMid-Stay Cleaning: For stays of 28 nights or more, we reserve the right to require a mid-stay cleaning to maintain the quality of the property. For longer stays, a mid-stay cleaning will be required every 28 nights thereafter. The cost will be collected separately, and the number of cleanings depends on the length of your stay. brbr brbrBoating & Dockage Advisory: Due to bridges and varying water depths, it is your responsibility to ensure that your boat can safely navigate local waters, access the canal, and fit the listed dockage before booking. While we are happy to provide general information based on our knowledge of the area, guests must exercise extreme caution when boating and ensure all activities comply with local regulations. brbr brbrLocal Wildlife & Pest Control: The Florida Keys are home to various insects (mosquitoes, no-see-ums, termites), reptiles, chickens, Key deer, and other wildlife. While routine pest control is in place, complete elimination is not possible. Guests should take precautions, such as using insect repellent and keeping doors closed, to minimize exposure. brbr brbrConstruction & Renovation Notice: Due to ongoing growth in the Florida Keys, renovations, construction, and road repairs may occur without prior notice. While we strive to provide a peaceful stay, iTrip Key West is not liable for any inconveniences caused by nearby construction. brbr brbrPhoto Disclaimer: All images are for illustrative purposes only. Individual features such as bed sizes, bedding, décor, appliances, colors, and amenities may vary, as these are privately owned homes and updates occur regularly. Lighting conditions and screen settings may also affect how colors appear. Please refer to the written description and reach out with any specific questions or concerns. All furnishings and décor are subject to change at any time.
Bed 4

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Bath 3

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Sleep 12

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Exceptional(9)

$663.75

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Private Vacation Home

Mariners Cove - The Kraken House

Summerland Key, Florida, United States

Mariner's Cove is a private island oasis. Featuring 5 large guest rooms, 3 full bathrooms and 2 1/2 bathrooms, Gourmet Chef's kitchen, formal dining room, breakfast nook, living area, private theater with 70 HD flat screen, oversized washer/dryer, ample outdoor seating, pool chase loungers & umbrellas, hammocks, outdoor gazebo/ wet bar with full outdoor kitchen and entertainment area, over .5 acres of lush tropical landscaping, outdoor fire pit, private boat dock on canal and lots of room to entertain. brbrThis home is essentially your own private resort and offers boaters quick access to the Gulf or Atlantic in just minutes from the private dock. brbrLocated just 30 minutes from Historic Key West or 30 minutes from Marathon you are close enough to the excitement of Duval Street but far enough away for a tranquil evening on the back porch watching the stars. Great home for multiple families, private functions, corporate retreats or just a perfect place to relax.brbrRoom Specifics: brThe Downstairs master bedroom features a full power adjustable King size canopy bed so you can tilt it up to watch TV or lay it down flat to sleep. The master bathroom has huge walk-in closets and a walk-in shower. Relax in the soaking tub or get to work at the Tommy Bahama desk in the attached office.brbrUpstairs has 4 bedrooms and 2 full baths. There are two rooms with King size fully power adjustable beds. These rooms are joined by a full bath. There is a bunk bedroom great for kids and both bunk beds are full size beds (upper & lower). And lastly a large room with two queen beds with on-suite bathroom, walk in closet and 55 smart TV. brbrFor special requests and questions please reach out to us as we are always available to assist with your Florida Keys destination needs. brbrNOTE: Security Cameras on site: brLocations: brFront Deck Pointing Toward DrivewaybrBulkhead: Pointing Toward Dock brUnder Deck: Pointing Toward Kayaks & EquipmentbrOn Pool Equipment brThere are two others one on back deck and one on tiki bar and are disconnected and covered during guest stays.
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Bath 3

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Sleep 10

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Exceptional(32)

$302.59

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Private Vacation Home

Canal Front (Deep Water) Tropical Villa

Summerland Key, Florida, United States

Custom designed Tropical Keys Home located on one of the nicest flow through deep water canals leading to the ocean in Summerland Key! Privacy 6' Walls surround the Villa to allow sunbathing delights!brbrThe Custom Canal Front Dock has Fenders, Cleats, and water spigots for all your boat needs. The Dock also has a swim platform and ladder to make all your water accessibility needs easy.brbrOpen floor plan that flows to the outside porch allows for tropical breezes and spacious entertainment. Plenty of parking area in front of house allows for storage of RV's, Boats, Cars and Planes if so desired.brbrSpacious kitchen to include all stainless appliances and large seating for 6 or more at the granite island bar! You can flow from the island bar to the open living room with wrap around leather sofa to view your favorite movies on the 50 Flat Panel TV.brbrMaster Bedroom has large California Walk-In Closet and King Bed with views of Outside porch and large Jacuzzi. Guest Bedroom has two spacious queen beds, 42 Flat Panel TV, and California Closets. Living Room has large pull out full sectional sleeper leather sofa.brbrThe Master and Guest Showers are a hedonistic experience with Rainfall Showers and 8 surrounding water sprays to immerse you in water pleasure.brbrThe Screened in Tropical private porch overlooks the Deep Water canal with great views of the ocean while the overhead porch fans cool you in the 8 person Hot Spring Jacuzzi. Enjoy the state of the art Jacuzzi with enough massaging jets to keep you smiling for some time. There is seating for 6-8 with comfortable Sofas, chairs and coffe table for tropical style conversations. Large sliding Porch doors open the house and master bedroom to the outside for great access to Jacuzzi and Screened in Porch.brbrThe House overlooks a beautiful private airstrip that allows for private aircraft and owners to fly in and access their tropical homes.brbrAnd speaking of world class entertainment! The State of the art Audio-visual system with surround sound fills the house and porch with the music of your choice. Flat Panel Plasma TV's in each room allow for majestic visual experiences. brbrAll the Audio and visual entertainment is controlled by a easy to use LCD remote. The house was designed with a unique lighting system that allows you to create endless moods of lighting for your pleasure. Have fun directing the lights! brbrThe house is Internet Ready with high speed wireless access for your laptop computer needs. Printer and copier also available if needed. brbrbrbrKeywords: House
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Bath 2

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Sleep 8

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Exceptional(54)

$1321.88

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Private Vacation Home

Oceanfront Home-Pool, Dock-Available Daily, Weekly or Monthly.

Summerland Key, Florida, United States

Large oceanfront home with breathtaking open water views! Seaclusion is a unique 3,400 square foot custom built home set on over an acre of tropical landscaping with a sparkling newly resurfaced heated pool on beautiful Summerland Key in the Lower Florida Keys. This house is permitted for daily, weekly or monthly rental. (Daily and weekly rental permits are rare in the Florida Keys!) br brEnjoy watching sunrise views over the open water of the Florida Keys. Our Non-Smoking home, Seaclusion, is comfortable and beautifully furnished for your stay. This three bedroom, two bath, uniquely designed home offers elegant living spaces including a palatial living area with carpet and tiled floors, a kitchen with new appliances, and an open staircase leading to the master suite. brbrRelax and enjoy the luxury, space, comfort, and beauty of Seaclusion's wide open living space where you'll find vacationing is easy. The master bedroom is located on the third floor. This spacious master suite features a king size bed, wet bar, and lavish his and her bath with jacuzzi tub.brbrMake yourself at home, Seaclusion gives you a whole new relaxed perspective on life. This picture-perfect home-away-from-home is open and airy. You'll enjoy the ocean breezes while dining and sipping frozen Pina Coladas at the kitchen bar or in the dining area while viewing the sparkling blue waters of the Atlantic Ocean. You'll also find a queen sleep sofa in the living area along with a full entertainment center for your family and friends. There are also two bedrooms with queen beds and a full bath on the second floor.brbrThe sliding doors lead to a screened in porch and outside shower. Follow the steps that lead to the 200 foot dock for swimming and boating. Highlights of this 3,400 square foot home include the master suite's private screened balcony and open sunbathing, the screened porch on the ground floor and a sparkling in-ground pool - a sea of tranquility right here on earth. brbrActivities: Our home is centrally located at Mile Marker 25 and is within minutes to Florida Keys style recreation, restaurants, shopping, and night life. Bahia Honda State Park with its world-famous beach is only 12 minutes away, Looe Key Reef and Marine Sanctuary is only 15 minutes away. We're located just 20 miles north of Key West where you'll love the great many eateries and shops. It's only a ten minute boat shuttle to take you to the exclusive Little Palm Island. Every water activity is at your back door just minutes from exceptional deep sea and flats fishing. Enjoy the very best the Florida Keys has to offer.br brIndulge yourself. Relax the body, lift the spirit, and invigorate the soul. It isn't hard to fall in love with a Florida Keys sunrise in this oceanfront estate. Seaclusion is a place where each day is better than the one before.br brMust be 25 years or older to rent this property.brKeywords: House
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Exceptional(124)

$532.5

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Private Vacation Home

Kelly's Kabin - Adorable Private Summerland Key Cottage

Summerland Key, Florida, United States

Kelly's Kabin is a recently renovated property freshly painted in tropical blues. It's a private home without neighbors. There is ample parking for multiple vehicles and your boat. The property is fully licensed for nightly, weekly, or monthly rentals.brSummerland Key is located at mile marker 24, which allows you to enjoy short drives north to Big Pine Key, Bahia Honda National Park, and Marathon Key. The major attractions of Key West are only 35 minutes to the south. Public transportation is conveniently accessible immediately adjacent to the cottage. No need to drive or find parking! Looe Key, with its phenomenal snorkeling and diving, is accessible through a variety of local charters. Kayaks, paddleboards and bicycles can be rented nearby. Fishing options include back country fishing, ocean fishing or bridge fishing. A lovely bike path is located at the back of the property. This property is close to favorite local restaurants as well as a small gourmet grocery. Food delivery is also available.brThe private lighted back patio overlooks a mangrove area, which leads to the Gulf of Mexico. The outdoor area includes a patio table, fire pit, charcoal grill, and fish cleaning station. You can observe native birds and often the endangered Key Deer from the patio.brInside the cottage, the main bedroom has a new king size bed. The pull-out couch has a comfortable gel foam mattress, and the front area has a comfortable single day bed.brThe full kitchen is equipped with new appliances, ample counter space and a breakfast bar.brThe bathroom has a bathtub and shower equipped with shampoo, conditioner, soap, clean towels, iron and a first aid kit. All linens, as well as beach towels and a beach umbrella are provided.brThe living area has a smart TV. The house is equipped with free Wi-Fi and a landline for emergencies.brWe hope you'll come relax in this welcoming tropical oasis and make new Low Key friends while here in paradise!brWe live locally and are available to assist to make your rental experience relaxing and enjoyable.
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Bath 1

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