Windward Bay Penthouse Escape

Windward Bay Penthouse Escape

  • Sarasota Bay sets the scene at Windward Bay Penthouse Escape. Stretch out in the light-filled living room, with beautiful blue water beyond the sunroom windows and a peaceful Longboat Key afternoon ahead.
    Sarasota Bay sets the scene at Windward Bay Penthouse Escape. Stretch out in the light-filled living room, with beautiful blue water beyond the sunroom windows and a peaceful Longboat Key afternoon ahead.
  • Room to linger, dine, and enjoy being together. Soft coastal tones, inviting lounge seating, and dining for four give this Longboat Key penthouse the relaxed elegance of a waterfront home.
    Room to linger, dine, and enjoy being together. Soft coastal tones, inviting lounge seating, and dining for four give this Longboat Key penthouse the relaxed elegance of a waterfront home.
  • Bayfront living with plenty to enjoy. Spend your Windward Bay days between two heated community pools, tennis, pickleball, and the Gulf beach across the road—or unwind with a workout and sauna before returning to your penthouse retreat.
    Bayfront living with plenty to enjoy. Spend your Windward Bay days between two heated community pools, tennis, pickleball, and the Gulf beach across the road—or unwind with a workout and sauna before returning to your penthouse retreat.
  • A comfortable dining space for four, framed by neutral upholstery and warm wood finishes. Its position beside the kitchen keeps the main living area open and connected.
    A comfortable dining space for four, framed by neutral upholstery and warm wood finishes. Its position beside the kitchen keeps the main living area open and connected.
  • An espresso before the beach. Fresh seafood for dinner. Granite counters, stainless steel appliances, and a thoughtfully stocked kitchen let you enjoy island living at your own pace, with a dishwasher to handle the cleanup.
    An espresso before the beach. Fresh seafood for dinner. Granite counters, stainless steel appliances, and a thoughtfully stocked kitchen let you enjoy island living at your own pace, with a dishwasher to handle the cleanup.
  • A restful king bedroom in navy, white, and soft coastal neutrals. Doors open to the enclosed sunroom, connecting this comfortable retreat with the penthouse’s signature waterfront setting.
    A restful king bedroom in navy, white, and soft coastal neutrals. Doors open to the enclosed sunroom, connecting this comfortable retreat with the penthouse’s signature waterfront setting.
  • A welcoming queen bedroom with crisp blue-and-white bedding and warm wood furnishings. Access to the enclosed sunroom brings the waterfront atmosphere into this inviting second bedroom.
    A welcoming queen bedroom with crisp blue-and-white bedding and warm wood furnishings. Access to the enclosed sunroom brings the waterfront atmosphere into this inviting second bedroom.
  • Coffee tastes better with a view like this. Settle into a recliner as Sarasota Bay and the mangrove shoreline fill the windows—your private sunroom for slow mornings and wonderfully lazy afternoons.
    Coffee tastes better with a view like this. Settle into a recliner as Sarasota Bay and the mangrove shoreline fill the windows—your private sunroom for slow mornings and wonderfully lazy afternoons.
  • Pools, courts, and a beautiful bayfront setting—all part of life at Windward Bay. This aerial shows the community’s recreation areas and its location along Gulf of Mexico Drive on Longboat Key.
    Pools, courts, and a beautiful bayfront setting—all part of life at Windward Bay. This aerial shows the community’s recreation areas and its location along Gulf of Mexico Drive on Longboat Key.
  • Come home to soft seating, sunlit interiors, and water views that stay with you throughout the living space. From an afternoon with a good book to a quiet evening together, this penthouse makes staying in feel like part of the vacation.
    Come home to soft seating, sunlit interiors, and water views that stay with you throughout the living space. From an afternoon with a good book to a quiet evening together, this penthouse makes staying in feel like part of the vacation.
  • A spacious living area with a large television, inviting seating, and an adjoining dining space. Cream upholstery and soft neutral finishes keep the room bright, comfortable, and easy to enjoy.
    A spacious living area with a large television, inviting seating, and an adjoining dining space. Cream upholstery and soft neutral finishes keep the room bright, comfortable, and easy to enjoy.
  • The enclosed sunroom adds a separate waterfront sitting area to the penthouse. Two recliners face a long wall of windows overlooking Sarasota Bay and the mangrove shoreline.
    The enclosed sunroom adds a separate waterfront sitting area to the penthouse. Two recliners face a long wall of windows overlooking Sarasota Bay and the mangrove shoreline.
  • Sarasota Bay fills the sunroom windows, with mangroves and open water stretching across the view. A peaceful waterfront backdrop that gives this penthouse its unmistakable sense of place.
    Sarasota Bay fills the sunroom windows, with mangroves and open water stretching across the view. A peaceful waterfront backdrop that gives this penthouse its unmistakable sense of place.
  • A second place to relax, connected to the main living room and both bedrooms. Comfortable recliners and coastal details make the enclosed sunroom feel like a natural extension of the home.
    A second place to relax, connected to the main living room and both bedrooms. Comfortable recliners and coastal details make the enclosed sunroom feel like a natural extension of the home.
  • The kitchen opens toward the dining and living areas, giving the home a comfortable, connected layout. Granite counters and warm wood cabinetry complement the relaxed coastal interiors.
    The kitchen opens toward the dining and living areas, giving the home a comfortable, connected layout. Granite counters and warm wood cabinetry complement the relaxed coastal interiors.
  • Coastal dining with all the comforts of home. The table seats four beside the kitchen, bringing an easy, welcoming feel to meals at your Longboat Key retreat.
    Coastal dining with all the comforts of home. The table seats four beside the kitchen, bringing an easy, welcoming feel to meals at your Longboat Key retreat.
  • Espresso, drip coffee, and a kitchen equipped for more than breakfast. Stainless steel cooking appliances and generous granite counters make this a practical, welcoming space for an extended stay.
    Espresso, drip coffee, and a kitchen equipped for more than breakfast. Stainless steel cooking appliances and generous granite counters make this a practical, welcoming space for an extended stay.
  • Stainless steel appliances, ample cabinetry, and granite countertops give the kitchen a polished, home-like feel. A full-size refrigerator provides the space that a longer island stay deserves.
    Stainless steel appliances, ample cabinetry, and granite countertops give the kitchen a polished, home-like feel. A full-size refrigerator provides the space that a longer island stay deserves.
  • A well-equipped kitchen with a full-size range, microwave, and plenty of counter space. Warm cabinetry and granite finishes bring the same comfortable style found throughout the penthouse.
    A well-equipped kitchen with a full-size range, microwave, and plenty of counter space. Warm cabinetry and granite finishes bring the same comfortable style found throughout the penthouse.
  • An open pass-through connects the kitchen with the living space beyond. Granite counters and a dishwasher add convenience without closing the kitchen off from the rest of the home.
    An open pass-through connects the kitchen with the living space beyond. Granite counters and a dishwasher add convenience without closing the kitchen off from the rest of the home.
  • The primary bedroom pairs a king bed with its own television and access to the enclosed sunroom. Blue-and-white bedding and coastal furnishings create a comfortable retreat beside the bay.
    The primary bedroom pairs a king bed with its own television and access to the enclosed sunroom. Blue-and-white bedding and coastal furnishings create a comfortable retreat beside the bay.
  • A king-size bed anchors the primary suite, with white furnishings and deep blue accents lending a calm coastal feel. The adjoining bathroom and walk-in closet complete the space.
    A king-size bed anchors the primary suite, with white furnishings and deep blue accents lending a calm coastal feel. The adjoining bathroom and walk-in closet complete the space.
  • A spacious walk-in closet gives an extended stay room to settle in. Hanging space, shelving, and drawers keep clothing and personal belongings neatly organized.
    A spacious walk-in closet gives an extended stay room to settle in. Hanging space, shelving, and drawers keep clothing and personal belongings neatly organized.
  • The primary bathroom features a generous double vanity, granite countertop, and warm wood cabinetry. Two sinks and ample storage add comfort to the private suite.
    The primary bathroom features a generous double vanity, granite countertop, and warm wood cabinetry. Two sinks and ample storage add comfort to the private suite.
  • A glass-enclosed shower and warm tile finishes complete the primary bathroom. Its connection to the king bedroom keeps the suite comfortable and self-contained.
    A glass-enclosed shower and warm tile finishes complete the primary bathroom. Its connection to the king bedroom keeps the suite comfortable and self-contained.
  • Blue-and-white bedding and a warm wood headboard give the queen bedroom a classic coastal look. A comfortable second retreat with the same relaxed feel as the rest of the home.
    Blue-and-white bedding and a warm wood headboard give the queen bedroom a classic coastal look. A comfortable second retreat with the same relaxed feel as the rest of the home.
  • The queen bedroom opens to the enclosed sunroom, with Sarasota Bay visible beyond. This connection to the waterfront is a lovely feature shared by both bedrooms.
    The queen bedroom opens to the enclosed sunroom, with Sarasota Bay visible beyond. This connection to the waterfront is a lovely feature shared by both bedrooms.
  • Navy cabinetry, a granite vanity, and a striped shower curtain bring coastal character to the second bathroom. A tub-and-shower combination rounds out this bright, welcoming space.
    Navy cabinetry, a granite vanity, and a striped shower curtain bring coastal character to the second bathroom. A tub-and-shower combination rounds out this bright, welcoming space.
  • Open bay water and a green mangrove shoreline, framed by the penthouse windows. This is the quiet, distinctly Longboat Key setting that makes an extended waterfront stay so appealing.
    Open bay water and a green mangrove shoreline, framed by the penthouse windows. This is the quiet, distinctly Longboat Key setting that makes an extended waterfront stay so appealing.
  • A different perspective on Longboat Key, with palms, green lawns, and neighboring homes beyond the building. The surrounding island neighborhood adds to Windward Bay’s residential feel.
    A different perspective on Longboat Key, with palms, green lawns, and neighboring homes beyond the building. The surrounding island neighborhood adds to Windward Bay’s residential feel.
  • The best of both shorelines: a bayfront community with Gulf beach access across the road. Windward Bay’s pools and courts sit within landscaped grounds, with Longboat Key’s Gulf shoreline beyond.
    The best of both shorelines: a bayfront community with Gulf beach access across the road. Windward Bay’s pools and courts sit within landscaped grounds, with Longboat Key’s Gulf shoreline beyond.
  • Windward Bay’s waterfront setting comes into focus from above: Sarasota Bay behind the building, with palms and landscaped grounds below. A beautiful location for an extended Longboat Key stay.
    Windward Bay’s waterfront setting comes into focus from above: Sarasota Bay behind the building, with palms and landscaped grounds below. A beautiful location for an extended Longboat Key stay.
  • Palm-lined grounds and covered parking frame the building’s exterior. Windward Bay combines a relaxed coastal setting with the everyday convenience of a residential condominium community.
    Palm-lined grounds and covered parking frame the building’s exterior. Windward Bay combines a relaxed coastal setting with the everyday convenience of a residential condominium community.
  • A waterfront-side view of the building, with broad windows facing the bay and green grounds below. The penthouse’s enclosed sunroom makes the most of this appealing orientation.
    A waterfront-side view of the building, with broad windows facing the bay and green grounds below. The penthouse’s enclosed sunroom makes the most of this appealing orientation.
  • Sarasota Bay stretches behind Windward Bay’s waterfront buildings, with palms and landscaped grounds along the shore. The setting brings open water and coastal greenery together in one inviting view.
    Sarasota Bay stretches behind Windward Bay’s waterfront buildings, with palms and landscaped grounds along the shore. The setting brings open water and coastal greenery together in one inviting view.
  • The building’s landscaped exterior and ground-level covered parking offer a welcoming arrival. Designated covered parking is included with your penthouse stay.
    The building’s landscaped exterior and ground-level covered parking offer a welcoming arrival. Designated covered parking is included with your penthouse stay.
  • Private in-unit laundry adds everyday convenience to an extended island stay. The stacked washer and dryer are neatly tucked into their own closet.
    Private in-unit laundry adds everyday convenience to an extended island stay. The stacked washer and dryer are neatly tucked into their own closet.
  • Covered parking beneath the building adds convenience to everyday arrivals and departures. Green lawns and landscaped grounds lie just beyond the carport.
    Covered parking beneath the building adds convenience to everyday arrivals and departures. Green lawns and landscaped grounds lie just beyond the carport.
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    F1142EA0-BCCE-4661-9E48-A5A9FA75AC0C
  • A covered exterior walkway leads to the condominium entrances. This final view shows the building’s approach and entry setting before you step inside your Windward Bay retreat.
    A covered exterior walkway leads to the condominium entrances. This final view shows the building’s approach and entry setting before you step inside your Windward Bay retreat.

Longboat Key, Florida

2 Bedrooms 2 full Baths 4 Guests 1312 sq. ft.

Overlooking Sarasota Bay, Windward Bay Penthouse Escape offers a welcoming home for an extended island stay, complete with beach access, heated pools, and tennis and pickleball courts.

This fourth-floor penthouse on Longboat Key has two bedrooms, two bathrooms, and comfortable accommodations for four. Sarasota Bay and the mangrove shoreline provide the backdrop, while deeded beach access across Gulf of Mexico Drive leads to the island’s Gulf shore. Inside, soft blues, cream, and warm neutrals give the home a relaxed coastal feel.

Bayfront living
Large windows line the enclosed sunroom, bringing in natural light and views of the water. Two comfortable recliners face the bay, making this an especially inviting part of the home. It’s a separate sitting area with the scenery in full view and the comfort of being indoors.

The adjoining living room has a cream sofa, two armchairs, and a television. The dining area and kitchen connect directly to it, creating a welcoming space for meals and time together. With both the living room and sunroom, there’s room for conversation as well as a quiet afternoon overlooking the bay.

Comforts for an extended stay
The primary bedroom features a king bed, a television, and a walk-in closet. The guest bedroom has a queen bed, and the condo has two bathrooms.

Granite countertops, wood cabinetry, and stainless steel appliances give the kitchen a warm, classic look. It’s well equipped for meals at home, with cookware, bakeware, and a dishwasher. The coffee station offers both a drip coffee maker and a Nespresso machine with a separate milk frother. The dining table seats four.

Private laundry and designated covered parking add everyday convenience, making the condo well suited to several weeks on the island.

Windward Bay amenities
The community’s waterfront grounds and recreation facilities are a big part of the appeal. Shared amenities include:

• Two heated swimming pools
• Tennis and pickleball courts
• A fitness center and saunas
• Bayfront walking paths
• Community barbecue grills
• Deeded Gulf beach access across Gulf of Mexico Drive

The bayfront paths offer a scenic setting close to home, while the pools, courts, and fitness facilities bring variety to a longer visit. Gulf beach access across the road complements the condo’s bayfront location, with two distinctly different shorelines nearby.

At home on Longboat Key
Windward Bay Penthouse Escape brings together a beautiful waterfront setting and the comfort of a furnished home. The enclosed sunroom gives it a memorable place to relax, while the kitchen, private laundry, and walk-in closet make settling in easy.

For an extended Longboat Key stay, this penthouse offers an appealing combination: Sarasota Bay views at home, Gulf beach access nearby, and a community with plenty to enjoy throughout the season.

Rooms

Primary Bedroom

1 King

Guest Bedroom

1 Queen

Amenities

Location & Attractions

  • Car - Recommended
  • Family Themed
  • Marina
  • Museums
  • Ocean Nearby
  • Zoo
  • Bay
  • Beach Access
  • Health Beauty Spa
  • Laundromat Nearby
  • View - Water
  • Waterfront

Bedroom & Laundry

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

Cleanliness & Safety

  • Common Surfaces Disinfected
  • Deadbolt Lock
  • Disinfectant Used While Cleaning
  • Fire Extinguisher
  • Outdoor Lighting
  • Linens High Temp Wash (140 degrees)
  • Self Check-In & Check-Out
  • Smoke Detector

Sports, Leisure & Adventure

  • Eco Tourism
  • 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
  • Wildlife Viewing

Bathroom

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

Entertainment

  • TV
  • Smart TV

Internet & Office

  • Ethernet Connection
  • Laptop Friendly Workspace
  • Wifi
  • Wifi - Free
  • Wifi - Speed 500mbps

Kitchen & Dining

  • Baking Sheet
  • BBQ Grill Utensils
  • Coffee
  • Coffee Maker
  • Cooking Basics
  • Dining Area or Room
  • Dining table
  • Dishes & Silverware
  • Freezer
  • Kitchen
  • Microwave
  • Oven
  • Refrigerator
  • Stove
  • Toaster
  • Blender
  • Dishwasher
  • Wine Glasses

Other Building, Complex Or Neighborhood Amenities

  • Hospital
  • Boat Slip or Dock - Community
  • Gym/Fitness Room - Community
  • Tennis Court - Community

Other Property Amenities

  • Air Conditioning
  • Ceiling Fan
  • Heating
  • Private Entrance
  • Exercise Equipment
  • Gym/Fitness Room - Private
  • Living Room
  • Pets - Not Allowed
  • Portable Fans
  • Tennis Court - Private

Parking & Facilities

  • Parking - Free
  • Elevator
  • Parking - On Site Free
  • Parking - Private

Services

  • Concierge - Available

Accessibility

  • Path to Entrance Lit at Night

Outdoor

  • BBQ Grill Area
  • BBQ Grill - Community
  • BBQ Grill - Gas
  • Beach Essentials
  • Outdoor Dining
  • Sun Loungers

Pool & Spa

  • Pool
  • Pool - Community
  • Pool - Fenced
  • Pool - Heated
  • Sauna - Community
See All Amenities +

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Availability

Select your travel dates to view a detailed quote.

Next available stay: Oct 20 – Nov 17 (28 nights)
Total before taxes$5,240.58
+ est. $640.51 taxes, added at checkout
Prices updated daily · select dates for an exact quote

Location

From $187/night incl. fees
next avail Oct 20 – Nov 17 · 28-night min
Number of Guests

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