Windsor Island Residence Single Family Homes For Sale in Davenport - 56 homes

Remarks: Escape to luxury in this immaculate Windsor Island Resort home in Davenport, Florida. This 8-bedroom, 6-bathroom residence offers a full sun, south-facing pool, and an open, airy floor plan perfect for vacation living, multigenerational guests, or a lucrative rental opportunity. Interiors feature tasteful, whimsical decor with carpeted bedrooms and durable ceramic tile plus luxury vinyl plank throughout for easy maintenance. Entertainment highlights include a dedicated game room and a game loft. Outdoor living is highlighted by a covered lanai and sun-drenched pool, with easy-to-maintain landscaping. The community provides a fully guarded, gated resort-within-a-resort experience and access to resort-style amenities such as a clubhouse, fitness center, and water features. Ideal for large families or investors seeking strong occupancy potential with ample common spaces and modern, low-maintenance finishes. Key Features: 8 bedrooms, 6 bathrooms South-facing pool; sun-filled outdoor living Game Room and Game Loft Carpeted bedrooms; ceramic tile and luxury vinyl plank throughout Easy maintenance design Resort-style, guarded, gated Windsor Island amenities

Listing is courtesy of: THE JERRY BARKER GROUP LLC (407-756-7296)

Listing Agent: Alyssa Barker (407-756-7296)

Remarks: An Exciting 7 Bedroom Vacation Home in Windsor Island is looking for a new owner. Close to the Disney Parks! Beautifully furnished with high end furniture. 5 King Bedrooms all with super comfortable beds. All bedrooms have tv's and the two kids bedrooms are fun themed with bunk beds. Garage has been converted into an out of this world game room with Double Gaming Station, Real Slate Pool table and a $10,000 Racing Simulator. Loft has an additional movie theater with a 165 inch screen and projector ready for a family movie night. Every bedroom in the house has its own TV. 5 adult bedrooms all have king beds and 3 are en-suite. Two kids rooms have bunks beds and fun theming with Wreck It Ralph and Moana. Kitchen is fully equipped with everything you would need for a comfortable stay. This 3300 sq ft vacation home is one of the newest vacation homes in Orlando and located in the wonderful resort of Windsor Island. The resort features super modern and spacious Club house. The resort amenities include a large Community Pool with a Slide, Hot Tub, Fitness Center, Arcade Room, Pickle Ball Courts, Volley Ball Court, Mini Golf court, Bar and Restaurant, Security gates and more. Call and schedule your private tour today!

Listing is courtesy of: FLORIDA REALTY RESULTS LLC (407-498-3838)

Listing Agent: Stani Delcheva (407-405-6815)

Remarks: Opportunity in Windsor Island Resort! Welcome to this beautifully furnished 5 bedroom, 4 bathroom home in one of the most desirable vacation communities in Central Florida. This property stands out with its elegant design, including custom wood accent walls that add warmth and a unique touch throughout the home. The open layout offers plenty of space for gathering and relaxing. Enjoy a private screened pool and a fully equipped game room, perfect for entertaining guests. One bedroom features a themed design, while the others are tastefully furnished in a clean, modern style, creating a more refined and comfortable feel. This home is fully furnished and ready to use, making it ideal as a short-term rental or a private vacation home. The design appeals to a wide range of guests looking for both fun and comfort. Windsor Island Resort offers amazing amenities, including a clubhouse, lazy river, water slides, fitness center, mini golf, and more. All just minutes from Disney, shopping, dining, and major attractions. A great opportunity to own a property that offers style, comfort, and rental potential.

Listing is courtesy of: MCO REALTY GROUP LLC (407-747-3822)

Listing Agent: Erika Neutzling (407-701-7948)

Remarks: Discover an outstanding opportunity in Windsor Island Resort, one of the most desirable vacation home communities near Disney! This beautifully furnished 8-bedroom, 6-bath residence offers an expansive open floor plan designed for both relaxation and entertaining. Step into a grand two-story foyer with a striking staircase leading upstairs. The chef-inspired kitchen features stone countertops and stainless steel appliances, seamlessly opening to the spacious living and dining areas, which flow directly to the outdoor living space. Outside, enjoy your own private retreat with a large screened-in heated pool, spa, and generous lanai—perfect for alfresco dining and lounging. The first floor includes the primary suite and an additional guest suite for convenience. Upstairs, you’ll find two private suites, two Jack-and-Jill bedrooms, a versatile loft, and a dedicated game room for endless fun. The garage has also been converted into another fantastic game space, making this home an ideal vacation destination. Residents and guests of Windsor Island Resort enjoy world-class amenities, including an 8,000-square-foot clubhouse, resort-style pool with lazy river, water slides, poolside cabanas, a fitness center, restaurant and bar, playground, and sports courts. Whether you’re searching for a luxury getaway or a high-performing investment property, this Windsor Island home offers the perfect combination of comfort, style, and location. Don’t miss this incredible opportunity!

Listing is courtesy of: RATIO REAL ESTATE, LLC (407-674-0460)

Listing Agent: Veronica Li (407-674-0460)

Remarks: LIVE VIRTUAL TOUR! Fully furnished pool home located in a desirable short-term rental resort community in the Kissimmee/Davenport area, offering an established history of guest use and rental activity. This property functions as a proven income-producing vacation rental asset within one of Central Florida’s most active tourism corridors. Featuring a private pool and spacious interior layout designed for group stays, this home provides flexible accommodations suitable for short-term rental, second-home use, or hybrid personal/investment use. Located within close proximity to major attractions, dining, shopping, and theme parks, the community continues to attract consistent visitor demand. Ideal for experienced STR investors seeking a stabilized asset in a high-supply but high-demand tourism market. Windsor Island Resort offers WORLD-CLASS AMENITIES, including a RESORT-STYLE CLUBHOUSE, ZERO-ENTRY POOL, LAZY RIVER, DUAL WATER SLIDES, WATER PARK, MINI-GOLF, CABANAS, FITNESS CENTER, SPORTS COURTS, A GAME ROOM, CAFÉ, ICE CREAM SHOP, AND MORE. Don’t miss the chance to own your dream vacation or investment home—schedule your private showing today!

Listing is courtesy of: REAL BROKER, LLC (855-450-0442)

Listing Agent: Liz Wilson (863-557-6135)

Remarks: PRICE IMPROVEMENT! Seller has reduced the price by $46,000! Luxurious Ten-Bedroom Home at Windsor Island Resort, Minutes from Disney World! This stunning, fully furnished, professionally themed vacation home generated over $100,000 in gross rental income last year, with more than $87,000 in future bookings already secured (June 2026–June 2027). These reservations can seamlessly transfer to the new owner if they continue with the current management company. A detailed rental income report is available upon request. This grand, fully furnished home built in 2023 offers exceptional rental income potential and is located at Windsor Island Resort, less than 10 miles from the Magic Kingdom. With 10 bedrooms, 8 bathrooms, and ample space to host guests, this home features an open kitchen, a private pool, spa, and a luxury-covered lanai. The two-car garage has been converted into a game room with insulation and AC/heater installed, providing additional entertainment space for guests. The home comfortably sleeps up to 22 guests, with each room professionally and thoughtfully themed-designed for guests of all ages. Enjoy a spacious living area, large kitchen, and dining space for the whole family. The pool screen has privacy film installed, providing guests with added privacy. Windsor Island Resort offers incredible amenities, including a 24-hour manned gated community, clubhouse with fitness center, splash pad, sports courts, full-service concierge & activities director, dual water slides, and a resort-style pool with lazy river & spa. Zoned for short-term rentals, the HOA includes lawn maintenance, landscaping, irrigation water, cable TV and 400MB unlimited high-speed internet. Experience the ultimate vacation home and schedule a showing today!

Listing is courtesy of: RATIO REAL ESTATE, LLC (407-674-0460)

Listing Agent: Veronica Li (407-674-0460)

Remarks: Welcome to 3811 Lana Ave in the highly sought-after Windsor Island Resort! This beautifully furnished home is turnkey and offers incredible potential as a short-term rental or vacation getaway. Featuring a bright, open layout perfect for entertaining, this property is designed for both comfort and style. Step outside and enjoy everything Windsor Island has to offer, including a resort-style pool, lazy river, and on-site bar & grill—creating an unbeatable guest experience. Ideally located near Central Florida’s top attractions, shopping, and dining, this home is the perfect blend of lifestyle and investment opportunity.

Listing is courtesy of: GLOBAL FLORIDA REALTY (407-380-3030)

Listing Agent: Michael Bouchard (407-443-1284)

Remarks: Beatiful 7 bedrooms 5.5 baths fully equipped and ready for you and your family to have fun and make income , at the biggest clubhouse in the community windsor island resort . You will fall in love with the rooms decorations and garage theme Avatar . Call us now and make your appointment.

Listing is courtesy of: GARCIA REALTY GROUP (407-920-3616)

Listing Agent: Elaine Garcia (407-920-3616)

Remarks: Modern Elegance Meets Resort Living at Windsor Island Welcome to the ultimate blend of style, space, and resort-style living—perfectly situated in the sought-after Windsor Island Resort community. Look No Further! Soon To Be Yours, This Stunning High-Occupancy-Performing Florida Vacation Investment Getaway Home offers unmatched value and versatility. Step inside and discover spacious luxury with 6 bedrooms and 4.5 bathrooms, thoughtfully designed to provide both comfort and privacy. The open-concept layout seamlessly connects the living, dining, and kitchen areas, making it ideal for entertaining and gathering. The gourmet kitchen is a showstopper, featuring granite countertops, stainless steel appliances, and an oversized island—perfect for cooking and conversation The main-floor master suite is a tranquil retreat, complete with a spacious en-suite bathroom and ample closet space. Upstairs, additional bedrooms and flexible living areas ensure plenty of room for guests or family. Step outside to your private oasis, where a covered lanai and sparkling pool invite you to unwind and enjoy the Florida sunshine. Whether you're relaxing poolside or dining alfresco, the outdoor living space offers the perfect setting for creating lasting memories. As part of Windsor Island Resort, you’ll enjoy access to world-class amenities, including: A state-of-the-art clubhouse with a game room Lazy river, waterslides, and splash park Fitness center, mini-golf, beach volleyball & basketball courts Fire pit with views of Disney fireworks Outdoor bar and dining area with multiple TVs Hammock garden and relaxing lounge spaces Location is everything. Walt Disney World, top-rated golf courses, luxury and value shopping, fine or family dining, and superior entertainment options. You're a short drive from Incredible New Universal Epic Universe, Universal Studios, Islands of Adventure, Universal's Volcano Bay, SeaWorld, and Orlando International Airport. Wait, there is so much more to explore Florida’s stunning coasts—from Cocoa Beach and the Kennedy Space Center to the incredibly soft, bright sands of Clearwater and St. Pete Beaches. This home offers more than just a place to stay—it delivers a lifestyle of comfort, fun, and an investment opportunity that pays for itself while you are not enjoying its beauty yourself. Don’t miss your chance to own a piece of paradise in one of Central Florida’s most desirable resort communities. Schedule your private showing today! Seller is Motivated, Make Your Move To Escape The Frigid Winter Weather Now!

Listing is courtesy of: REAL BROKER, LLC (407-279-0038)

Listing Agent: Tony Pandzic (321-431-9575)

Remarks: Welcome to this beautifully maintained 7-bedroom, 5.5-bathroom home located in the highly sought-after Windsor Island Resort, where short-term rentals are permitted. Overlooking a tranquil open view, this fully furnished, turnkey property offers exceptional income potential as both a luxury vacation retreat and a high-performing investment. The open-concept living area features elegant tile flooring and sliding glass doors that lead to your private pool and spa—perfect for enjoying Florida’s sunshine year-round. The chef’s kitchen is equipped with stainless steel appliances, granite countertops, and abundant cabinetry, ideal for entertaining large groups. Each bedroom is professionally themed, creating a fun and memorable experience for guests. The home offers two master suites—one on each level—providing comfort and privacy for families and groups. Upstairs, the spacious loft is designed as a game room, adding an additional entertainment space. Windsor Island Resort offers world-class amenities including an 8,000-square-foot clubhouse with concierge services, fitness center, arcade, sundry shop, and on-site restaurant and bar. Outdoor amenities feature a heated zero-entry pool, lazy river, dual waterslides, splash pad, mini golf, fire pit with Disney fireworks views, and private cabanas. Ideally located with quick access to I-4, Orlando, Tampa, MCO Airport, and Florida’s famous beaches. Zoned for short-term rental and completely turnkey, this is an investor-ready opportunity with strong performance history.

Listing is courtesy of: RATIO REAL ESTATE, LLC (407-674-0460)

Listing Agent: Veronica Li (407-674-0460)

Remarks: **This home comes with a lender credit provided by seller's preferred lender, pending qualification.** Welcome to 1697 Kona Lane in Windsor Island Resort, a fully furnished 7 bedroom, 5 bathroom pool home located in one of the Davenport/Orlando area’s sought-after resort-style communities. Built in 2021, this spacious residence offers over 3,200 square feet of well-designed living space with an open-concept layout, stylish finishes, and a private screened pool and in-ground spa for year-round enjoyment. Inside, the home features a bright and functional floor plan with a large kitchen with stone counters, solid-surface finishes, stainless steel appliances, and generous gathering space ideal for everyday living, entertaining, or hosting guests. Multiple bedroom suites provide flexibility and comfort, while the home’s fully furnished setup offers a convenient move-in-ready opportunity. Located in Windsor Island Resort, residents and guests enjoy access to resort-style amenities including a clubhouse, fitness center, playground, and community pool, all within a gated setting designed for convenience and recreation. The community’s location places you near Central Florida’s major attractions, dining, shopping, golf, and entertainment, with easy access to Disney, Orlando area theme parks, and key travel routes. Whether you are searching for a spacious Florida getaway, a second home, or a property in a popular short-term-rental area, this home offers size, location, amenities, and turnkey convenience in the heart of it all.

Listing is courtesy of: LPT REALTY, LLC (877-366-2213)

Listing Agent: Johanna Chandler (352-217-1527)

Remarks: Experience elevated resort living at 3633 Lily Lane, a fully furnished 10-bedroom, 8-bath luxury vacation residence in the sought-after guard-gated Windsor Island Resort. Built in 2022 and thoughtfully designed for high guest appeal, this expansive 4,399 sqft home offers elegant open living spaces, beautifully appointed themed bedrooms, a converted climate-controlled game room, and a private screened pool and spa for effortless indoor-outdoor entertaining. Windsor Island delivers a true destination lifestyle with premier amenities including a clubhouse, fitness center, resort-style pool, lazy river, splash pad, arcade, sports courts, mini golf, playground, and on-site tavern and grill. Ideally located near Disney, shopping, dining, and major Central Florida attractions, this turnkey property is a standout opportunity for a refined second home, income-producing short-term rental, or unforgettable family retreat.

Listing is courtesy of: INTEREALTY SERVICE (626-328-8535)

Listing Agent: Emma Yue (626-328-8535)

Remarks: Discover an incredible opportunity to own a like-new 5-bedroom vacation home in the highly sought-after Windsor Island Resort! This fully furnished, turn-key property is ready for rentals right now—no need to wait months for new construction! This stunning home boasts 5 bedrooms, 5.5 bathrooms, and over 2,500 sq. ft. of living space. Enjoy an open floor plan with beautiful views of the heated private pool. The spacious loft area provides extra entertainment space, while the gourmet kitchen features an oversized island, granite countertops, and stainless steel appliances. Windsor Island Resort is one of the top vacation destinations in the Disney area, offering world-class amenities. This home is the perfect investment for vacation rentals or personal use. Don’t miss this chance—schedule a showing today!

Listing is courtesy of: FLORIDA CONNEXION PROPERTIES (407-574-2636)

Listing Agent: Priscila Triska (321-354-5459)

Remarks: Experience the pinnacle of luxury vacation home ownership at Windsor Island Resort with this spectacular 10-bedroom, 8-bathroom retreat offering nearly 4,400 square feet of impeccably designed living space. Purposefully crafted to deliver an unforgettable guest experience while maximizing rental performance, this extraordinary residence seamlessly blends upscale resort living with exceptional investment potential. From the moment you enter, you'll be captivated by expansive open-concept living areas, designer-inspired finishes, multiple themed guest suites, and sophisticated gathering spaces designed for large families, executive retreats, reunions, and luxury group travel. The gourmet kitchen serves as the heart of the home, flowing effortlessly into spacious dining and entertainment areas that create the perfect setting for memorable vacations. Step outside to your own private tropical oasis featuring a screened resort-style pool and spa, where guests can unwind in complete comfort after enjoying Central Florida's world-renowned attractions. Every detail has been thoughtfully designed to elevate the vacation experience and encourage repeat bookings year after year. Located within the prestigious Windsor Island Resort, owners and guests enjoy access to an impressive collection of world-class amenities including a grand clubhouse, state-of-the-art fitness center, resort-style pool complex, water attractions, sports courts, and recreational amenities that continue to make this one of Central Florida's premier vacation destinations. Ideally situated just minutes from Walt Disney World, Universal Orlando Resort, championship golf courses, luxury shopping, fine dining, and Orlando's entertainment corridor, this turnkey property offers the rare combination of luxury lifestyle, prime location, and income-producing potential. Whether expanding your investment portfolio, securing a second home, or acquiring a premier vacation retreat, this exceptional residence represents a unique opportunity to own a trophy asset in one of the nation's most desirable short-term rental markets. Welcome to a destination where luxury, leisure, and investment excellence come together. Welcome to Windsor Island Resort.

Listing is courtesy of: REAL BROKER, LLC (855-450-0442)

Listing Agent: Ryan Rogers (407-492-0674)

Remarks: PRICE REDUCED – SELLER MOTIVATED!!! Best-priced 10-bedroom home in Windsor Island Resort — fully furnished and turnkey! Discover the charm of this exquisite home perfect for large families or hosting guests. The newly updated kitchen features modern amenities, while the cozy living room provides a welcoming space for relaxation. Enjoy the expansive layout, abundant natural light, and a refreshing pool. This property provides a unique opportunity to create your ideal home. Don’t miss out on making this beautiful house your own! Windsor Island is a perfect Resort for your family and guest. Call me today!

Listing is courtesy of: MS LAND & BUILDING LLC (407-512-1213)

Listing Agent: Vivian Branco (305-469-0729)

Remarks: This is the one investors wait for — a proven, high-occupancy vacation home in Windsor Island Resort with professionally themed rooms, a sun-drenched south-facing pool, and a price that makes the decision easy. The 6-bedroom, 4.5-bath Hideaway floor plan at 4450 Kaipo Road has earned its reputation as a guest favorite, and now it's available at a price that opens the door wide for the next owner. Inside, 3,117 sq. ft. of bright, open living space does exactly what a great vacation home should — it pulls people together. A sleek contemporary kitchen with large island seating, a spacious gathering room, and a dedicated dining area flow seamlessly together on the main floor, while the first-floor owner's suite offers a private retreat away from the energy of the main living areas. The upstairs is built for unforgettable group stays. A Mickey Mouse room, a Frozen-inspired suite, and a Harry Potter-styled bedroom — all professionally themed — are the kind of spaces guests search for specifically, book for, and rave about afterward. The expansive loft adds a second living and entertainment hub complete with pool table and oversized sectional, giving every guest their own corner of the house to claim. Outside, the south-facing heated pool and spa deliver all-day Florida sunshine onto a lanai built for long, lazy afternoons and evenings that drift well past sunset. This is the kind of outdoor setup guests actively seek. And then there's Windsor Island Resort itself — the Hawaiian-inspired community that continues to set the bar for vacation living near Disney. Tropical waterpark-style pool, lazy river, splash zone, water slides, outdoor dining, fitness facilities, sports courts, firepit lounge, and a signature clubhouse that delivers island energy from the moment you arrive. Walt Disney World is just minutes away. Aloha! Proven occupancy. Iconic themed rooms. South-facing pool. Windsor Island Resort. And a price that reflects a genuine opportunity — not a compromise. Be sure to check out the lifestyle video included with this listing. All information, including room dimensions, is deemed reliable but not guaranteed. Buyers and buyers agents are encouraged to verify all details independently.

Listing is courtesy of: FATHOM REALTY FL LLC (888-455-6040)

Listing Agent: Susan Benante, Llc (407-259-6211)

Remarks: 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.

Listing is courtesy of: MS LAND & BUILDING LLC (407-512-1213)

Listing Agent: Natalia Romanelli Mourao (407-405-4534)

Remarks: Fully furnished 10-bedroom, 8-bathroom luxury resort home located in the highly sought-after Windsor Island Resort. Designed for both exceptional rental performance and unforgettable vacations, this expansive home features a converted garage game room, plus a massive upstairs loft complete with a private theater and pool table—perfect for entertaining guests of all ages. The home boasts beautifully designed themed bedrooms, a heated private pool and spa, and a fully screened lanai for year-round enjoyment. Situated in a guard-gated community, Windsor Island Resort offers premier amenities and peace of mind. The monthly assessment covers comprehensive community operations, including professional on-site management, operation of the Aloha Clubhouse and resort amenities, landscaping and irrigation, valet trash and litter pickup, bulk cable and internet, 24-hour manned front gate, and roving patrol services. An exceptional opportunity to own a turn-key vacation rental or second home in one of Central Florida’s most popular resort communities.

Listing is courtesy of: UNIONE REALTY INC (407-808-9080)

Listing Agent: Kyle Li (407-808-9080)

Remarks: Welcome to your dream vacation home just minutes from Disney, this exceptionally furnished 7-bedroom, 5.5-bathroom pool home offers the perfect blend of luxury, comfort, and privacy. This beautifully updated residence features bright open-concept living and dining areas with modern flooring, a spacious kitchen with contemporary appliances and a large island, and the convenience of dual primary suites, one on the main floor and one upstairs, making it ideal for multi-generational living or guest flexibility. A cozy upstairs loft provides an additional living space perfect for movies, gaming, or relaxation, while the remaining bedrooms are generously sized and thoughtfully designed for comfort. The garage has been converted to a games room so you and your guests can enjoy hours of entertainment and fun. Step outside to your private oasis with a sparkling pool and spa, enhanced by the tranquility of no rear neighbors and a covered patio perfect for lounging or entertaining. Located in Windsor Island Resort, just minutes from Disney, this community is packed with world-class amenities: a zero-entry resort pool, lazy river, water slide, splash pad, clubhouse with concierge and arcade, fitness center, mini golf, playground, firepit with Disney fireworks views, and the Blue Marlin Grille restaurant. Zoned for short-term rentals that are in high demand year-round, this property offers both lifestyle and income potential as this home is an outstanding investment or personal vacation retreat offering exceptional convenience and year-round appeal.

Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)

Listing Agent: Ping Ma (863-332-0298)

Remarks: This professionally designed, fully furnished 7-bedroom, 5.5-bath vacation retreat offering over 3,200 square feet of upgraded living space in one of Central Florida’s most sought-after resort communities. This turnkey property blends upscale finishes with functional design, ideal for investors and vacationers alike. Step inside to discover a spacious open-concept layout perfect for large groups. The gourmet kitchen features rich espresso cabinetry, granite countertops, stainless steel appliances, and a generous center island with seating that's ideal for casual dining and entertaining. The main-level primary suite offers direct pool access and a spa-inspired en suite bath with dual sinks, a garden tub, and walk-in shower. Upstairs, a sprawling loft has been transformed into a private game and movie room, surrounded by six additional bedrooms and four full baths, providing ample space for guests and family. Outside, enjoy your own private oasis with a heated pool and spa, covered lanai, and plenty of seating for sun-soaked relaxation or evening gatherings. Located in Windsor Island Resort, just minutes from Disney, this community is packed with world-class amenities: a zero-entry resort pool, lazy river, water slide, splash pad, clubhouse with concierge and arcade, fitness center, mini golf, playground, firepit with Disney fireworks views, and the Blue Marlin Grille restaurant. With short-term rentals allowed and high demand year-round, this property offers both lifestyle and income potential.

Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)

Listing Agent: Ping Ma (863-332-0298)