The Windward House

The Windward House

  • A modern living room with a large L-shaped sofa, colorful cushions, coffee tables, and a brick fireplace. Large windows offer a view of an outdoor pool area.
    A modern living room with a large L-shaped sofa, colorful cushions, coffee tables, and a brick fireplace. Large windows offer a view of an outdoor pool area.
  • A modern indoor patio with skylights, white walls, lounge chairs, and a small garden area with plants. The space is adjacent to a pool visible through large sliding glass doors.
    A modern indoor patio with skylights, white walls, lounge chairs, and a small garden area with plants. The space is adjacent to a pool visible through large sliding glass doors.
  • Bright modern kitchen and dining area featuring a wooden ceiling with exposed beams, large windows, and sliding glass doors leading to an outdoor pool.
    Bright modern kitchen and dining area featuring a wooden ceiling with exposed beams, large windows, and sliding glass doors leading to an outdoor pool.
  • A modern kitchen with a terrazzo island, wooden stools, white cabinetry, built-in appliances, open shelving, and large windows. A row of wooden lockers is visible on the right.
    A modern kitchen with a terrazzo island, wooden stools, white cabinetry, built-in appliances, open shelving, and large windows. A row of wooden lockers is visible on the right.
  • A modern bedroom with a striped bedspread, a bedside table with a lamp, a chair, a ceiling fan, and sliding glass doors. The room also features an attached bathroom with tiled walls.
    A modern bedroom with a striped bedspread, a bedside table with a lamp, a chair, a ceiling fan, and sliding glass doors. The room also features an attached bathroom with tiled walls.
  • A minimalist bedroom with a bed, a ceiling fan, a wall-mounted TV, and a sliding glass door leading to an outdoor area with greenery. Two bedside tables with lamps are on either side of the bed.
    A minimalist bedroom with a bed, a ceiling fan, a wall-mounted TV, and a sliding glass door leading to an outdoor area with greenery. Two bedside tables with lamps are on either side of the bed.
  • A modern bedroom with two single beds, wooden headboards, a large window, a ceiling fan, a wall-mounted TV, and a small table. The room has a clean, minimalist design with potted plants visible outside.
    A modern bedroom with two single beds, wooden headboards, a large window, a ceiling fan, a wall-mounted TV, and a small table. The room has a clean, minimalist design with potted plants visible outside.
  • A narrow, modern home office with a built-in wooden desk, shelves, a black chair, and framed artwork on the wall.
    A narrow, modern home office with a built-in wooden desk, shelves, a black chair, and framed artwork on the wall.
  • A patio with four white lounge chairs beside a screened pool, overlooking a waterway surrounded by trees and greenery under a clear blue sky.
    A patio with four white lounge chairs beside a screened pool, overlooking a waterway surrounded by trees and greenery under a clear blue sky.
  • Aerial view of a waterfront neighborhood with multiple houses, some featuring enclosed swimming pools, docks, and manicured lawns next to a canal bordered by trees.
    Aerial view of a waterfront neighborhood with multiple houses, some featuring enclosed swimming pools, docks, and manicured lawns next to a canal bordered by trees.
  • Spacious modern living room with a large sectional sofa, coffee tables, and a fireplace. Open kitchen is visible in the background. Natural light fills the room through large windows.
    Spacious modern living room with a large sectional sofa, coffee tables, and a fireplace. Open kitchen is visible in the background. Natural light fills the room through large windows.
  • A modern living room with a large sectional sofa, coffee table, fireplace, art on the wall, and a glass door leading to an outdoor pool area with patio furniture.
    A modern living room with a large sectional sofa, coffee table, fireplace, art on the wall, and a glass door leading to an outdoor pool area with patio furniture.
  • A modern living room with a large L-shaped sofa adorned with pink and yellow cushions, a mid-century lounge chair, two white coffee tables, and sliding glass doors opening to a patio.
    A modern living room with a large L-shaped sofa adorned with pink and yellow cushions, a mid-century lounge chair, two white coffee tables, and sliding glass doors opening to a patio.
  • Modern living room with a sectional sofa, bright cushions, a coffee table, a fireplace, contemporary art, and a ceiling fan. Walls are white with large windows and recessed lighting.
    Modern living room with a sectional sofa, bright cushions, a coffee table, a fireplace, contemporary art, and a ceiling fan. Walls are white with large windows and recessed lighting.
  • Modern dining area with a wooden table and colorful chairs, adjacent to a living room. Large glass doors reveal an outdoor patio with a pool. The space features a high ceiling with exposed beams.
    Modern dining area with a wooden table and colorful chairs, adjacent to a living room. Large glass doors reveal an outdoor patio with a pool. The space features a high ceiling with exposed beams.
  • Modern, open-concept living and dining area with white walls, large windows, a light wood dining table, a seating area with a TV, and framed artwork on the walls.
    Modern, open-concept living and dining area with white walls, large windows, a light wood dining table, a seating area with a TV, and framed artwork on the walls.
  • A modern, open-concept kitchen and dining area with white cabinets, wooden accents, pendant lighting, large windows, an island with bar stools, and a dining table with white chairs.
    A modern, open-concept kitchen and dining area with white cabinets, wooden accents, pendant lighting, large windows, an island with bar stools, and a dining table with white chairs.
  • Modern kitchen with white cabinets, a large island with a terrazzo countertop, stainless steel appliances, and wooden ceiling beams. A sliding glass door leads to an enclosed porch area.
    Modern kitchen with white cabinets, a large island with a terrazzo countertop, stainless steel appliances, and wooden ceiling beams. A sliding glass door leads to an enclosed porch area.
  • A modern kitchen with a center island, white cabinets, and a wooden ceiling. Large glass doors lead to a pool outside. The space is well-lit with natural light from the windows.
    A modern kitchen with a center island, white cabinets, and a wooden ceiling. Large glass doors lead to a pool outside. The space is well-lit with natural light from the windows.
  • Modern kitchen with a terrazzo island, three wooden stools, stainless steel appliances, white cabinets, open shelving, and wooden ceiling accents.
    Modern kitchen with a terrazzo island, three wooden stools, stainless steel appliances, white cabinets, open shelving, and wooden ceiling accents.
  • A modern kitchen with a terrazzo countertop island, exposed wooden ceiling beams, and large sliding glass doors leading to a patio with a pool and outdoor seating.
    A modern kitchen with a terrazzo countertop island, exposed wooden ceiling beams, and large sliding glass doors leading to a patio with a pool and outdoor seating.
  • Modern kitchen featuring a built-in oven and stainless-steel refrigerator. A glass door opens to a patio with pool and greenery visible outside.
    Modern kitchen featuring a built-in oven and stainless-steel refrigerator. A glass door opens to a patio with pool and greenery visible outside.
  • A modern kitchen with a gas stove, white countertops, and shelves holding dishes and glasses. A sink with a faucet is to the right of the stove, and a window above the sink lets in natural light.
    A modern kitchen with a gas stove, white countertops, and shelves holding dishes and glasses. A sink with a faucet is to the right of the stove, and a window above the sink lets in natural light.
  • Modern kitchen with orange tiled backsplash, white countertops, and built-in appliances. A laundry area with stacked washer and dryer is visible in the foreground, and an open living space is seen beyond.
    Modern kitchen with orange tiled backsplash, white countertops, and built-in appliances. A laundry area with stacked washer and dryer is visible in the foreground, and an open living space is seen beyond.
  • A modern laundry room with a stacked washer and dryer on the left, white cabinets, a countertop with a coffee machine, and an orange backsplash. A doorway leads to another room.
    A modern laundry room with a stacked washer and dryer on the left, white cabinets, a countertop with a coffee machine, and an orange backsplash. A doorway leads to another room.
  • A modern bedroom with a striped bed, a ceiling fan, windows with blinds, and a view of a pool outside. A uniquely shaped mirror hangs on the wall opposite the bed.
    A modern bedroom with a striped bed, a ceiling fan, windows with blinds, and a view of a pool outside. A uniquely shaped mirror hangs on the wall opposite the bed.
  • A modern bedroom features a bed with green and white striped bedding, a wooden dresser with art above it, small windows, and a ceiling fan. The room has white walls and a terrazzo floor.
    A modern bedroom features a bed with green and white striped bedding, a wooden dresser with art above it, small windows, and a ceiling fan. The room has white walls and a terrazzo floor.
  • A minimalistic bedroom with a striped bedspread, a padded armchair, a wooden dresser, and a wall-mounted artwork. Large windows offer a view of greenery outside. The room features white walls and a ceiling fan.
    A minimalistic bedroom with a striped bedspread, a padded armchair, a wooden dresser, and a wall-mounted artwork. Large windows offer a view of greenery outside. The room features white walls and a ceiling fan.
  • A minimalist home office with a wooden desk, chair, floating shelves, and skateboard decor. An adjacent room with chairs and large windows is visible through the open door.
    A minimalist home office with a wooden desk, chair, floating shelves, and skateboard decor. An adjacent room with chairs and large windows is visible through the open door.
  • A modern bathroom with a double-sink vanity featuring circular sinks, a terrazzo countertop, a large mirror, and wall-mounted faucets. Lights are on both sides of the mirror, and a toilet is on the right.
    A modern bathroom with a double-sink vanity featuring circular sinks, a terrazzo countertop, a large mirror, and wall-mounted faucets. Lights are on both sides of the mirror, and a toilet is on the right.
  • A modern bathroom with double sinks, a large mirror, white tiled walls, a glass enclosed shower, and a black-and-white patterned rug on the floor.
    A modern bathroom with double sinks, a large mirror, white tiled walls, a glass enclosed shower, and a black-and-white patterned rug on the floor.
  • A modern bedroom with a wooden bed, a light grey quilt, a small nightstand with a lamp, a wall-mounted shelving unit, a desk with a chair, a ceiling fan, and a window with blinds.
    A modern bedroom with a wooden bed, a light grey quilt, a small nightstand with a lamp, a wall-mounted shelving unit, a desk with a chair, a ceiling fan, and a window with blinds.
  • A minimalist bedroom features a bed with light bedding, a wooden desk with a chair, wall-mounted shelves, a small wall-mounted table, a ceiling fan, and a landscape picture on the wall.
    A minimalist bedroom features a bed with light bedding, a wooden desk with a chair, wall-mounted shelves, a small wall-mounted table, a ceiling fan, and a landscape picture on the wall.
  • Modern bathroom with white subway tiles, a round mirror, a vessel sink on a terrazzo countertop, a wall-mounted faucet, a toilet, and a walk-in shower with a rain showerhead and black fixtures.
    Modern bathroom with white subway tiles, a round mirror, a vessel sink on a terrazzo countertop, a wall-mounted faucet, a toilet, and a walk-in shower with a rain showerhead and black fixtures.
  • A minimalist bedroom with white walls, two twin beds with wooden headboards, a nightstand with two lamps, a patterned rug, and three horizontal windows. A ceiling fan is centered above.
    A minimalist bedroom with white walls, two twin beds with wooden headboards, a nightstand with two lamps, a patterned rug, and three horizontal windows. A ceiling fan is centered above.
  • Modern bathroom with a pink ribbed sink on a countertop with a terrazzo surface, black wall-mounted faucets, a square mirror with rounded edges, and a metallic toilet paper holder on a white wall.
    Modern bathroom with a pink ribbed sink on a countertop with a terrazzo surface, black wall-mounted faucets, a square mirror with rounded edges, and a metallic toilet paper holder on a white wall.
  • Minimalist bathroom with a white toilet, a holder with a roll of toilet paper, and a framed picture of a person on a high platform on the wall. The walls are painted light gray.
    Minimalist bathroom with a white toilet, a holder with a roll of toilet paper, and a framed picture of a person on a high platform on the wall. The walls are painted light gray.
  • Screened-in patio with a ceiling fan, seating area, potted plants, and views of a swimming pool.
    Screened-in patio with a ceiling fan, seating area, potted plants, and views of a swimming pool.
  • A modern indoor courtyard with glass walls, a ceiling fan, black chairs around a table, and a small garden area with plants in the center.
    A modern indoor courtyard with glass walls, a ceiling fan, black chairs around a table, and a small garden area with plants in the center.
  • Spacious indoor patio with skylight, seating area, indoor plants, and view of an outdoor pool through large windows.
    Spacious indoor patio with skylight, seating area, indoor plants, and view of an outdoor pool through large windows.
  • A covered outdoor pool area with padded lounge chairs, clear glass sliding doors, and surrounded by trees and plants.
    A covered outdoor pool area with padded lounge chairs, clear glass sliding doors, and surrounded by trees and plants.
  • A long, rectangular outdoor pool enclosed by a screen structure, adjacent to a modern house with large windows and a covered patio area with seating.
    A long, rectangular outdoor pool enclosed by a screen structure, adjacent to a modern house with large windows and a covered patio area with seating.
  • A screened-in outdoor swimming pool area with a clear blue pool, surrounded by green foliage, and a residential neighborhood visible in the background under a bright, sunny sky.
    A screened-in outdoor swimming pool area with a clear blue pool, surrounded by green foliage, and a residential neighborhood visible in the background under a bright, sunny sky.
  • A rectangular swimming pool is enclosed by a white screened structure, surrounded by greenery with clear skies visible above. Chairs and a table are in the background.
    A rectangular swimming pool is enclosed by a white screened structure, surrounded by greenery with clear skies visible above. Chairs and a table are in the background.
  • Outdoor seating area with several white lounge chairs on a gravel patio, surrounded by greenery, with a view of a canal and a house with a white roof in the background.
    Outdoor seating area with several white lounge chairs on a gravel patio, surrounded by greenery, with a view of a canal and a house with a white roof in the background.
  • A scenic waterfront neighborhood featuring boats, docks, grassy lawns, trees, and houses under a clear blue sky.
    A scenic waterfront neighborhood featuring boats, docks, grassy lawns, trees, and houses under a clear blue sky.
  • Single-story white house with large windows, a gravel path, greenery in the foreground, and a screened patio area in a grassy yard.
    Single-story white house with large windows, a gravel path, greenery in the foreground, and a screened patio area in a grassy yard.
  • An empty boat lift sits on a waterfront, with a large house and trees visible across the water on a clear day.
    An empty boat lift sits on a waterfront, with a large house and trees visible across the water on a clear day.
  • Front view of a modern, single-story house with angular rooflines, a paved driveway, and surrounded by various trees and shrubs. The sky is clear and blue.
    Front view of a modern, single-story house with angular rooflines, a paved driveway, and surrounded by various trees and shrubs. The sky is clear and blue.
  • Covered outdoor area with a white ceiling and walls, tiled floor, and open passage leading to a garden. Features include a black door, glass door, and two wall-mounted lights.
    Covered outdoor area with a white ceiling and walls, tiled floor, and open passage leading to a garden. Features include a black door, glass door, and two wall-mounted lights.
  • Two bicycles, one black and one yellow, are mounted vertically on a white wall in a spacious, tiled room with no additional furnishings.
    Two bicycles, one black and one yellow, are mounted vertically on a white wall in a spacious, tiled room with no additional furnishings.
  • Covered patio area with white ceiling and brick flooring, featuring black-framed doors and windows. Two yellow bicycles are mounted vertically on the right wall, with greenery visible in the background.
    Covered patio area with white ceiling and brick flooring, featuring black-framed doors and windows. Two yellow bicycles are mounted vertically on the right wall, with greenery visible in the background.
  • Contemporary one-story house with a paved driveway, landscaped garden, and large front windows under a clear blue sky.
    Contemporary one-story house with a paved driveway, landscaped garden, and large front windows under a clear blue sky.
  • Aerial view of a suburban neighborhood featuring houses with green yards, a waterway, and abundant trees, with several homes situated along the canal.
    Aerial view of a suburban neighborhood featuring houses with green yards, a waterway, and abundant trees, with several homes situated along the canal.
  • Aerial view of a residential neighborhood with houses, trees, and a canal, with high-rise buildings in the background near the coastline.
    Aerial view of a residential neighborhood with houses, trees, and a canal, with high-rise buildings in the background near the coastline.
  • Aerial view of a residential neighborhood with houses, backyards, and pools situated along a narrow canal.
    Aerial view of a residential neighborhood with houses, backyards, and pools situated along a narrow canal.
  • Aerial view of a modern house with a grey roof, landscaped garden, and a screened-in swimming pool adjacent to a body of water.
    Aerial view of a modern house with a grey roof, landscaped garden, and a screened-in swimming pool adjacent to a body of water.

Siesta Key, FL

3 Bedrooms 2 full, 1 half Baths 6 Guests 1696 sq. ft. Pets OK

Welcome to your slice of paradise on Siesta Key, where luxury meets comfort in this completely refurbished Mid-Century Modern vacation home just minutes from the stunning beaches. Nestled in a serene neighborhood, this dog-friendly retreat offers a seamless blend of style, functionality, and relaxation.

As you step inside, you're greeted by the timeless allure of terrazzo floors that flow gracefully throughout the open floor plan, enhancing the home's mid-century charm. The attention to detail and abundance of natural light create an inviting ambiance that sets the stage for a memorable stay.

The heart of the home is a harmonious fusion of form and function. In the living room, a cozy fireplace invites you to unwind on a plush sectional sofa, while a large SMART TV stands ready to entertain. The dining room, kitchen, and living area flow together effortlessly, adorned with iconic mid-century modern furniture and clean lines that exude style.

Slide open the ceiling-to-floor glass doors, and you'll step into your own private oasis. The outdoor living space beckons with modern furnishings, a heated pool glistening invitingly, and a courtyard adorned with sun loungers – the perfect spot to soak up the Florida sun. And with direct access to the deep-water canal leading to Sarasota Bay, aquatic adventures are just a stone's throw away.

Back inside, the gourmet kitchen awaits the culinary enthusiast. A large island with stools invites casual dining and conversation, while stainless steel appliances stand ready to bring your culinary creations to life. A kitchen nook boasts a wine cooler, coffee station, and full-size washer and dryer, ensuring convenience at every turn.

Retreat to the primary bedroom through the adjacent office, where a king-size bed adorned with plush linens promises a restful night's sleep. Enjoy direct access to the pool area for a refreshing morning swim or a midnight dip under the stars. The ensuite bathroom boasts a spacious glass walk-in shower and a vanity with two sinks, providing a spa-like experience.

Guests will find their own slice of paradise in the well-appointed bedrooms. A queen-sized bed graces one room, complete with a SMART TV for entertainment. In the second guest bedroom, two twin beds offer flexible sleeping arrangements, also accompanied by a SMART TV. The guest bathroom features a sleek glass walk-in shower, while a convenient half bath is located just down the hall.

Throughout the home, contemporary design elements harmonize with the natural surroundings, creating a seamless transition between indoor and outdoor living spaces. Whether you're seeking relaxation, adventure, or simply a stylish sanctuary to call your own, this Mid-Century Modern haven on Siesta Key promises an unforgettable escape.

A $250 pet fee, per pet is required. No dogs in the pool at any time. A fee of $12 per day is charged for running the pool heater. If you wish to use the pool heater during your stay, kindly contact us to have it turned on. Thank you!

The Beauty of Siesta Key
Siesta Key is a barrier island positioned between the Gulf of Mexico and intracoastal waterway. The powdery white sandy beaches are world renown and stretch over 8 miles along the southwest coast of Florida. Siesta Key is a water-lovers paradise offering crystal clear turquoise water, sailing, fishing, swimming and so much more. Play in the gentle waves and shallow waters, gather unique seashells, or build a sandcastle with your kids or grandkids.

The Siesta Key Village offers a wide selection of shops, cafes, and live music for both its residents and guests. From local oyster bars to waterside dining, Siesta Key has something for every palate.

***Please note, a $250 pet fee is required. *** No dogs allowed in the pool at any time. Thank you!

Rooms

Primary Bedroom

1 King

Guest Bedroom

1 Queen

Guest Bedroom

2 Twin

Amenities

Location & Attractions

  • Car - Not Necessary
  • Family Themed
  • Marina
  • Museums
  • Ocean Nearby
  • Bay
  • Beach Access
  • Health Beauty Spa
  • Romantic Themed
  • View - Water
  • Waterfront
  • Zoo

Bathroom

  • Body Soap
  • Conditioner
  • Hair Dryer
  • Hot Water
  • Shampoo
  • Shower Gel

Bedroom & Laundry

  • Bed Linens
  • Essentials
  • Extra Pillows & Blankets
  • Hangers
  • Iron & Ironing Board
  • Towels
  • Dryer - Private
  • Washer - Private

Cleanliness & Safety

  • Carbon Monoxide Detector
  • Deadbolt Lock
  • Disinfectant Used While Cleaning
  • Fire Extinguisher
  • Linens High Temp Wash (140 degrees)
  • Outdoor Lighting
  • Self Check-In & Check-Out
  • Smoke Detector
  • First Aid Kit

Entertainment

  • TV
  • Smart TV

Internet & Office

  • Laptop Friendly Workspace
  • Wifi
  • Wifi - Free
  • Desk
  • Desk Chair
  • Ethernet Connection
  • Office

Kitchen & Dining

  • Coffee
  • Coffee Maker
  • Cooking Basics
  • Dishes & Silverware
  • Freezer
  • Kitchen
  • Microwave
  • Oven
  • Refrigerator
  • Stove
  • Toaster
  • Dining Area or Room
  • Dining table
  • Dishwasher
  • Kitchen Island

Other Building, Complex Or Neighborhood Amenities

  • Hospital
  • Gym/Fitness Room - Community

Other Property Amenities

  • Air Conditioning
  • Heating
  • Private Entrance
  • Living Room
  • Pets - Allowed
  • Single Level Home

Parking & Facilities

  • Parking - Free
  • Parking - Private

Services

  • Concierge - Available

Sports, Leisure & Adventure

  • Antiquing
  • Bird Watching
  • Boating
  • Cycling
  • Diving
  • Fishing
  • Fishing - Bay
  • Fishing - Deep Sea
  • Fishing - Fly
  • Fishing - Freshwater
  • Fishing - Pier
  • Fishing - Surf
  • Golf
  • Horseback Riding
  • Jet Skiing
  • Outlet Shopping
  • Parasailing
  • Sailing
  • Shopping
  • Snorkeling
  • Swimming
  • Water Skiing
  • Wildlife Viewing
  • Eco Tourism
  • Wind Surfing

Outdoor

  • BBQ Grill Area
  • BBQ Grill - Private
  • Beach Essentials
  • Fenced Yard
  • Garden or Backyard
  • Kayak or Canoe
  • Patio or Balcony
  • Veranda

Pool & Spa

  • Pool
  • Pool - Private
See All Amenities +

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Availability

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Location

from 265.00 / night

Number of Guests

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