Windsor Island Residence Homes with Pool Community Features

Windsor Island Residence Homes with Pool Community Features

Welcome to Windsor Island Residence, an enchanting subdivision nestled in the heart of Davenport, Florida. This vibrant community is perfectly situated in Polk County, just a stone's throw away from the bustling attractions of Orlando, making it an ideal haven for both residents and vacationers alike.

Windsor Island Residence is designed with family-friendly living in mind, offering a delightful array of homes that cater to diverse lifestyles. Each property is thoughtfully crafted, showcasing modern designs, spacious layouts, and premium finishes. The highlight of this community is undoubtedly its stunning homes with private pools, where you can soak up the Florida sun in the comfort of your own backyard. Imagine lazy afternoons spent lounging by the poolside or hosting unforgettable gatherings with family and friends amidst the lush tropical landscape.

Beyond the beautiful homes, Windsor Island Residence boasts an impressive selection of community features that elevate your living experience. Residents can enjoy access to a state-of-the-art clubhouse, complete with recreational facilities, fitness centers, and social spaces designed for gatherings and events. The community is also adorned with walking trails, playgrounds, and picnic areas, encouraging an active and engaging lifestyle for all ages.

With its prime location, luxurious amenities, and a welcoming atmosphere, Windsor Island Residence is more than just a place to live; it's a lifestyle choice. Whether you’re looking for a permanent residence or a vacation retreat, this community offers the perfect blend of relaxation and adventure. Discover your dream home today and embrace the vibrant Florida lifestyle at Windsor Island Residence!

Newest Windsor Island Residence Homes with Pool Community Features

$459,000
5 Beds ⋅ 5 Baths ⋅ Windsor Island Residence SubDv. ⋅ 33897 Zip Code
Welcome to this beautifully furnished 5-bedroom, 4.5-bath townhome in the highly desirable Windsor Island Resort. This two-story home features stylish furnishings, comfortable living areas, and a private screened-in splash pool with covered patio, perfect for relaxing or entertaining. One of the home’s prime advantages is its location directly across from the clubhouse and resort amenities, offering guests quick and convenient access to all the fun. Windsor Island Resort features a gated entrance, clubhouse, fitness center, resort-style pool with lazy river, splash pad, playground, mini golf, on-site restaurant and bar. Conveniently located near Central Florida’s world-class attractions, shopping, and dining, this turnkey property is ideal as a vacation home, primary residence, or income-producing rental. All information available to the Seller and Listing Agent has been provided in the listing and disclosures. If information is not included, it is not available to us. Buyers and their agents are responsible for verifying all information that is important to their purchase, including but not limited to HOA rules and regulations, leasing restrictions, fees, room dimensions, square footage, lot size, taxes, and any other property details. All measurements and listing information are approximate and should be independently verified by the Buyer and Buyer's Agent.

936 Paradise Drive, Davenport
$849,900
10 Beds ⋅ 8 Baths ⋅ Windsor Island Residence SubDv. ⋅ 33897 Zip Code
For buyers seeking a short-term rental investment designed around the guest experience, 2127 Lelani Circle is a fully furnished, turnkey property in the amenity-rich Windsor Island Resort, offering 4,399 sq. ft. with 10 bedrooms and 8 bathrooms. Custom painting, cinematic character theming and atmospheric LED lighting effects throughout give the interior its own identity, while a south-facing heated pool and spa extend the vacation experience outdoors. The open blue-and-white living space introduces the home's blend of luxury and distinctive design, with a leather sectional and coordinated seating arranged around a custom textured media wall feature with LED backlighting. The kitchen pairs modern cabinetry, stainless steel appliances and granite countertops with an oversized island seating 4 and nearby dining for 8. Two bedrooms are located on the main level for added convenience and flexibility. The signature Mickey suite is hand-painted throughout in a Mickey-inspired palette, complemented by vintage-style Mickey and Minnie artwork and a private en suite that also serves as the pool bath. Several upstairs bedrooms create their own immersive settings through hand-painted walls and ceilings, oversized murals, framed artwork and integrated LED lighting effects. Spider-Man, Minions, Frozen and Avengers designs surround guests with color and character, joined by a galaxy room in painted starfields and a wizarding room with portraits set into the ceiling. The oversized Mario-themed game loft continues the experience with bold color-blocked walls, illuminated gaming art, sectional seating, a wall-mounted television, ping-pong and foosball tables, while the 2-car garage remains available for parking and storage. Beyond the sliding doors, an extended paver deck surrounds the south-facing heated pool and spa, while the covered lanai provides shade for outdoor seating and alfresco dining. Then there is Windsor Island itself—ALOHA! The Hawaiian-inspired Aloha Clubhouse anchors a water-park-style complex featuring a zero-entry resort pool, lazy river, dual waterslides, splash zone, hot tub, private cabanas and the Blue Marlin Grille. A fitness center, arcade, miniature golf, playground, sports court, firepit and organized activities complete the amenity offering. All of this is just a few miles from Walt Disney World, with convenient access to shopping, dining and Central Florida's major roadways. All information provided, including room sizes, is deemed reliable but not guaranteed and should be independently verified by the buyer or buyer's agent.

2127 Lelani Circle, Davenport
$565,000
6 Beds ⋅ 5 Baths ⋅ Windsor Island Residence SubDv. ⋅ 33897 Zip Code
Welcome to this spectacular 6-bedroom vacation home in the highly sought-after Windsor Island Resort, offering privacy with no rear neighbors, beautiful open views, and exceptional resort-style living. Fully furnished and ready to enjoy, this home features a heated private pool, spacious loft, and an open-concept floor plan designed for both entertaining and relaxing. The kitchen is the heart of the home, featuring an oversized island, granite countertops, stainless steel appliances, and plenty of space for gathering with family and friends. The open living and dining areas offer beautiful views of the pool and the open space behind the property, creating a bright and inviting atmosphere.Adding to the home's unique appeal, two bedrooms feature beautifully hand-painted Disney theme park murals, creating magical themed retreats that are sure to delight guests of all ages. With generous living spaces, multiple bedrooms, a loft, and a private pool, this home is perfectly suited for memorable family vacations and entertaining.Windsor Island Resort has earned its reputation as one of the premier vacation destinations in the Disney tourist area, and it's easy to see why. The resort features an impressive 8,000-square-foot clubhouse with a lounge, concierge services, sundry shop, fitness center, arcade/game room, Blue Marlin Grille Bar & Restaurant, playground, mini-golf course, and a firepit area with views of Disney fireworks.Outdoor amenities are equally impressive, including a heated beach-style zero-entry resort pool, lazy river, water slide, splash pad, poolside cabanas, and abundant sun loungers.Whether you're looking for a vacation retreat or a beautifully furnished property in one of Central Florida's most desirable resort communities, this home delivers the space, amenities, privacy, and unforgettable resort experience that owners and guests are looking for.

1230 Aloha Boulevard, Davenport
$399,000
5 Beds ⋅ 5 Baths ⋅ Windsor Island Residence SubDv. ⋅ 33897 Zip Code
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, 237 Jetty Way is ready for its next owner to enjoy from day one.

237 Jetty Way, Davenport
$720,000
8 Beds ⋅ 6 Baths ⋅ Windsor Island Residence SubDv. ⋅ 33897 Zip Code
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 ⋅ Windsor Island Residence SubDv. ⋅ 33897 Zip Code
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
$625,000
7 Beds ⋅ 6 Baths ⋅ Windsor Island Residence SubDv. ⋅ 33897 Zip Code
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
$409,000
5 Beds ⋅ 5 Baths ⋅ Windsor Island Residence SubDv. ⋅ 33897 Zip Code
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 ⋅ Windsor Island Residence SubDv. ⋅ 33897 Zip Code
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
$509,999
5 Beds ⋅ 5 Baths ⋅ Windsor Island Residence SubDv. ⋅ 33897 Zip Code
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
$649,000
6 Beds ⋅ 5 Baths ⋅ Windsor Island Residence SubDv. ⋅ 33897 Zip Code
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
$459,000
5 Beds ⋅ 5 Baths ⋅ Windsor Island Residence SubDv. ⋅ 33897 Zip Code
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
Start Your Search