Windsor Island Residence Homes with Pool

Windsor Island Residence Homes with Pool

Welcome to Windsor Island Residence, an enchanting community nestled in the heart of Davenport, Florida, in beautiful Polk County. This vibrant subdivision is a hidden gem that combines modern living with a touch of luxury, making it the perfect place to call home.

Windsor Island Residence boasts an array of stunning homes, each designed to cater to the diverse needs of families and individuals alike. One of the most appealing features of this community is the availability of homes with private pools. Imagine stepping out into your backyard oasis, where you can bask in the Florida sunshine, host summer barbecues, or enjoy a refreshing dip in your own pool. The homes here are thoughtfully designed with open floor plans, spacious living areas, and contemporary finishes, ensuring that comfort and style are never compromised.

Beyond the beautiful homes, Windsor Island Residence offers an array of community amenities that enhance the living experience. Residents can take advantage of lush green spaces, walking trails, and recreational facilities, making it an ideal environment for families and active lifestyles. The community is also conveniently located near major highways, shopping centers, and dining options, ensuring that everything you need is just a short drive away.

With its perfect blend of luxury, convenience, and community spirit, Windsor Island Residence is more than just a place to live—it's a lifestyle. Come discover your dream home in this delightful Davenport neighborhood and experience the joys of Florida living at its finest!

Newest Windsor Island Residence Homes with Pool

$720,000
8 Beds ⋅ 6 Baths ⋅ O6431292 MLS
Spacious 8-Bedroom Pool Home in the Sought-After Windsor Island Resort – Davenport, FL Welcome to your dream vacation home! This stunning 8-bedroom, 6-bathroom single-family residence is located in the highly desirable Windsor Island Resort—one of Davenport’s premier gated vacation communities just minutes from Disney. Step inside and be amazed by the modern décor, open-concept layout, and spacious living areas perfect for entertaining and relaxing. The fully equipped gourmet kitchen features sleek finishes, stainless steel appliances, and a large island overlooking the bright and airy dining and living spaces. This home offers the ultimate in flexibility and comfort with multiple themed bedrooms, dual primary suites, and plenty of room for large families or groups. Step outside to your private covered lanai and screened-in pool, where you can unwind or enjoy Florida’s sunshine all year round. Located just a short walk to the resort-style clubhouse, residents and guests enjoy access to Windsor Island’s incredible amenities, including a lazy river, water slides, splash pad, fitness center, mini golf, sports courts, and more. Whether you’re looking for a lucrative short-term rental investment or a family-friendly getaway, this home has it all. Don’t miss this opportunity to own a piece of paradise in Central Florida’s top resort community.

2123 Lelani Circle, Davenport
$489,000
5 Beds ⋅ 5 Baths ⋅ O6430639 MLS ⋅ 710 BLDG.
Turn-Key Short-Term Rental | Strong Occupancy Appeal South Facing Pool | Guard-Gated Resort Income-producing short-term rental — professionally designed & fully furnished, especially the theme rooms to attract tourists Turn-key operation — no setup required, ready to generate revenue immediately with many existing bookings can be transferred. Professional designer furniture set up with frozen and star war theme rooms. Pool heater was replaced in 2025.Highly desirable south-facing screened pool — maximizes sunlight & rental demand 5 bedrooms / 4.5 baths — ideal for large groups up to 14 persons, higher ADR & longer stays First-floor guest suite — appeals to multigenerational & accessibility-focused guests Upstairs loft adds entertainment space & booking flexibility Prime location near clubhouse & guarded gate — superior guest convenience vs interior units Close to the club house by walking 3 minutes. Located in a live guard-gated resort community with premium amenities: -Resort-style pools & lazy river with poolside bar -On-site restaurant -State-of-the-art fitness center -Mini golf, tennis, basketball & sand volleyball Strong appeal for Airbnb / Vrbo investors seeking consistent occupancy Ideal for investors targeting cash flow + long-term appreciation

716 Gardenia Lane, Davenport
$799,000
10 Beds ⋅ 9 Baths ⋅ O6428920 MLS
Where Central Florida vacations become the stories families retell for years. Tucked behind the gates of Windsor Island Resort, this 10-bedroom, 8.5-bath retreat (4,399 SqFt, built 2021) was made for the arrival — that moment when ten doors open onto ten different worlds and the whole group scatters, laughing, before anyone has unpacked a single bag. Professionally themed bedrooms turn bedtime into the best part of the day. The private game room keeps the energy alive long after the parks have closed. And when the evening finally slows down, the screened pool and spa glow quietly under the Florida sky — private, warm, unhurried, entirely yours. Inside, light moves freely across an open-concept main level where kitchen, living and dining spaces flow as one and slide open to the pool deck. Fully furnished and professionally decorated throughout, with a 2-car garage and every detail already in place. Beyond your door, Windsor Island Resort delivers the rest: a signature clubhouse, resort pool, fitness center, playground and on-site dining. Minutes from US-27 in Davenport and a short drive from Central Florida's world-famous attractions. Offered fully furnished and As-Is, income-ready with no minimum stay. Windsor Island is a short-term-rental resort community, and the home is designated for vacation-rental and owner vacation use rather than permanent residency. Buyer and buyer's agent to verify all measurements, figures, HOA rules and use restrictions. Schedule your private showing today.

2280 Lelani Circle, Davenport
$625,000
7 Beds ⋅ 6 Baths ⋅ S5153316 MLS
1876 Summer Drive at Windsor Island Resort is the turnkey, fully furnished vacation home investors and second-home buyers have been waiting for. Designed for both fun and function, this spacious property offers an open-concept layout, private screened pool, multiple ensuite-style bedroom options, themed rooms, and an entertainment-packed upstairs loft with theater seating, games, and air hockey. It has everything today’s guests are looking for in a memorable Central Florida stay. From the moment you step inside, you’re welcomed by a bright and spacious open-concept floor plan where the kitchen, dining area, and living room come together seamlessly, each with beautiful views of the private screened pool. The first-floor primary suite offers comfort and convenience, featuring an ensuite bathroom and direct pool access. The main level also includes a half bath and laundry room for added functionality. Upstairs, the fun continues with a spacious family room and game loft designed for entertainment. Whether enjoying movie night in theater-style seating, playing video games, challenging friends to chess or checkers, or enjoying a game of air hockey, this home is built for memory-making. The upstairs bedrooms are thoughtfully arranged in three separate sections, offering privacy and flexibility for owners and guests. At the front of the home, two bedrooms each feature their own private bathrooms. In the middle there is two additional bedrooms are positioned near the charming themed rooms, Princess and Captain America, adding a fun and memorable touch for younger guests. Toward the rear, two more bedrooms share a full bathroom, creating a layout that comfortably accommodates larger groups. With close proximity to Disney, Universal, SeaWorld, Orlando International Airport, and the resort-style amenities of Windsor Island, this beautifully furnished property is ready to deliver as a primary residence, second home, or short-term rental investment.

1876 Summer Drive, Davenport
$429,000
5 Beds ⋅ 5 Baths ⋅ S5152558 MLS ⋅ 267 BLDG.
Price Adjustment - Welcome to resort-style living at Windsor Island Resort! This beautifully furnished 5-bedroom, 4.5-bath townhome, built in 2021, offers 2,293 sq ft of thoughtfully designed space behind a guard-gated entrance. The first floor features a bedroom and full bath for guests, while upstairs you'll find a primary suite with a walk-in closet, a second primary suite, two additional themed bedrooms that are well-decorated to attract short-term rental guests, and a versatile loft. All appliances are stainless steel. Step out to your own private screened pool, or enjoy the community's resort-style amenities. This is a pet-free house, although pets are allowed in the community. Windsor Island Resort is known for outstanding amenities, including an 8,000 sq. ft. clubhouse, resort-style pool and spa, lazy river, poolside cabanas, fitness center, on-site restaurant and bar, playgrounds, sports courts, arcade, and lounge areas for guests of all ages. The community's prime location provides convenient access to US 192, I-4, shopping, dining, golf, supermarkets, and Central Florida's major attractions. Whether purchased as a personal vacation retreat or income-producing short-term rental investment, this beautifully upgraded home offers a compelling opportunity in one of the Disney area's most desirable resort communities, just a short drive away. With a fully furnished turnkey setup, immersive themed spaces, standout entertainment areas, and a guest-focused design throughout, 267 Jetty Way is ready for its next owner to enjoy from day one.

267 Jetty Way, Davenport
$569,000
5 Beds ⋅ 5 Baths ⋅ O6420344 MLS ⋅ 996 BLDG.
Fully furnished Themed short term rental. LED lighting inside and out. Game room in the house! Open layout with modern kitchen and private pool. Windsor Island Resort has amazing amenities: mini-golf, a resort style pool, waterslides, lazy river, and bar and restaurant. This home will impress any guests!

996 Paradise Drive, Davenport
$585,000
5 Beds ⋅ 5 Baths ⋅ O6419919 MLS ⋅ Jetty BLDG.
Stylish former model home with private pool in the highly desirable Windsor Island Resort community! Located directly across from the clubhouse and resort amenities, this fully furnished end-unit home offers an excellent location, abundant natural light, and a bright, open floor plan. The kitchen features a breakfast bar, granite countertops, stainless steel appliances, and ample white cabinetry. Enjoy your own private screened pool, perfect for relaxing or entertaining. Windsor Island Resort offers outstanding amenities, including a clubhouse, fitness center, resort-style pool, waterslide, lazy river, volleyball and tennis courts, play zone, mini golf, and full-service bar. Conveniently located just minutes from Disney World, area attractions, restaurants, and shopping. Great opportunity for vacation use, short-term rental, or investment. Booking history and calendar available in MLS attachments.

108 Jetty Way, Davenport
$689,000
7 Beds ⋅ 6 Baths ⋅ O6412823 MLS
Exceptional corner-lot vacation home located just steps from the clubhouse in the highly sought-after Windsor Island Resort. This beautifully maintained and fully furnished property offers a spacious open-concept layout, modern finishes, and ample space for guests. Enjoy the convenience of being just steps from to the resort's amenities, including a lazy river, water slides, clubhouse, fitness center, arcade, sports courts, and more. The private screened pool area provides the perfect setting for relaxation and entertainment. The property is owner-managed and is currently utilized as a short-term vacation rental. Existing future reservations may be available for transfer, subject to booking platform policies and applicable requirements. Ideally located near Walt Disney World, shopping, dining, and major highways, this fully furnished property offers an excellent opportunity to own a vacation home in one of Central Florida's most popular resort communities.

1837 Summer Drive, Davenport
$520,000
5 Beds ⋅ 5 Baths ⋅ O6410922 MLS ⋅ Na BLDG.
Welcome to your piece of Paradise on 806 Paradise Drive! This fully furnished 5-bedroom, 4.5-bathroom vacation home is located in the highly desirable Windsor Island Resort and sits on one of the best lots in the community. This premium corner lot offers extra privacy with no neighbor on one side and no direct rear neighbor, while also being conveniently located near the clubhouse and close to the security gate. The home features an open-concept layout, modern kitchen with granite countertops, stainless steel appliances, spacious living and dining areas, and sliding doors leading to a covered lanai and screened-in heated pool. A convenient pool bath is accessible from the lanai. Upstairs offers a generous primary suite, additional bedrooms, and a versatile loft area perfect for a game room or family lounge. All furniture, appliances, and décor are included, making this a true turn-key opportunity. Windsor Island Resort offers resort-style amenities including a clubhouse, pool, lazy river, water slides, splash zone, playground, fitness center, and more. Just minutes from Disney, shopping, dining, and Central Florida attractions. Perfect as a vacation home or investment property! Schedule your showing.

806 Paradise Drive, Davenport
$659,000
6 Beds ⋅ 5 Baths ⋅ O6409306 MLS
Immaculately maintained and fully turnkey, this pristine 6-bedroom vacation pool home in the highly sought-after Windsor Island Resort shows like a model and is completely guest-ready from day one. Why spend thousands updating furniture, décor, and themed spaces when it’s already been done for you? This beautifully updated property features stylish new furnishings, custom décor, immersive Star Wars, Marvel, and Disney-inspired rooms, and an incredible upgraded game room designed to create unforgettable guest experiences. The spacious open-concept layout is perfect for entertaining, while the private screened pool and spa offer the ideal place to relax after a day at the parks. Guests will also enjoy Windsor Island Resort’s incredible amenities, including water slides, lazy river, volleyball, basketball, tiki bar, game room, and mini golf. Completely furnished, exceptionally well-kept, and rental-ready, this one-of-a-kind home offers strong short-term rental appeal and is the perfect luxury vacation retreat or income-producing investment near Orlando’s top attractions.

1191 Aloha Boulevard, Davenport
$660,000
7 Beds ⋅ 6 Baths ⋅ O6406813 MLS
Stunning two-story home, fully furnished and thoughtfully designed to offer comfort, sophistication, and excellent investment potential. A charming front porch and landscaped entry create a warm and elegant first impression. Perfect for short-term rentals, this property is located in a high-demand vacation rental area, making it an excellent opportunity for investors or those seeking a vacation home. The home features 7 spacious bedrooms, 5 full bathrooms, and 1 half bath, providing plenty of space to accommodate family and guests comfortably. The kitchen is fully equipped with all essential appliances and is move-in ready. Sliding glass doors seamlessly connect the indoor and outdoor living spaces, leading to a private screened pool, covered lanai, and an ideal area for entertaining and barbecues. To enhance the resort-style experience, the home also includes a heated spa, perfect for relaxing year-round. The laundry room is fully equipped and ready for use. The spacious living and dining areas create a comfortable and inviting atmosphere, perfect for gathering and entertaining. Located in the exclusive Windsor Island Resort, residents and guests enjoy access to outstanding amenities, including a resort-style pool, clubhouse, game room, beach volleyball court, water park, lazy river, fitness center, and more. Conveniently located near major attractions such as Walt Disney World Resort, Universal Orlando Resort, ChampionsGate, shopping, restaurants, supermarkets, and with easy access to US-27 and I-4, making travel throughout Central Florida simple and convenient. This is an incredible opportunity for anyone looking for a luxury vacation home or an income-producing investment property in a prime location. Contact us today to schedule a private showing.

1671 Kona Lane, Davenport
$459,000
5 Beds ⋅ 5 Baths ⋅ O6404784 MLS ⋅ . BLDG.
Welcome to your perfect Florida escape — a beautifully maintained 5-bedroom, 4.5-bath townhome nestled within the sought-after Windsor Island Resort, just steps from the community’s coveted clubhouse. Whether you’re searching for a vacation retreat or income-producing investment property, this home checks every box. Thoughtfully cared for and move-in ready, this spacious townhome offers generous living spaces designed for both relaxation and entertaining. The open-concept main floor flows effortlessly to your private west-facing splash pool — the ideal spot to unwind each evening as the Florida sun sets after a magical day at Walt Disney World, Universal Studios, or any of the area’s world-class attractions, all just minutes away. Five well-appointed bedrooms provide ample room for family and guests, while four and a half baths ensure everyone’s morning routine runs smoothly. The prime location within the resort means the award-winning clubhouse — complete with a water park, restaurant, fitness center, and more — is literally right outside your door. Highlights: • 5 bedrooms / 4.5 bathrooms • Private west-facing splash pool — perfect for golden-hour relaxation • Steps to the Windsor Island Resort Clubhouse & water park amenities • Minutes to Walt Disney World, Universal Studios & area theme parks • Well-maintained and vacation-rental ready • Ideal as a vacation home or investment property Don’t miss this opportunity to own a piece of one of Central Florida’s most desirable resort communities. Schedule your private showing today!

616 Jasmine Lane, Davenport
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