Windsor Island Homes for Sale in Davenport - 102 homes

Remarks: Welcome to 3818 Lana Ave, Davenport — an exceptional 5-bedroom, 4.5-bathroom home featuring a private screened-in pool, a game room, and professionally decorated themed bedrooms inspired by Mickey Mouse, Harry Potter, Star Wars, Frozen, and Avatar—perfect for unforgettable family moments or standout short-term rental appeal. Enjoy an open floor plan, modern kitchen, multiple en-suites, and stylish furnishings throughout. Located just minutes from Disney, golf courses, shopping, and dining, this home blends comfort, fun, and location in one turnkey package. Don’t miss out — schedule your showing today!

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

Listing Agent: Jonathan Pinto (407-408-7407)

Remarks: PRICE IMPROVEMENT! Seller has reduced the price by $46,000! Luxurious Ten-Bedroom Home at Windsor Island Resort, Minutes from Disney World! 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: Step into a world of enchantment and luxury at 2210 Lelani Circle! A fully furnished and turnkey 10-bedroom, 8-bathroom home that is meticulously decorated to deliver a timeless Florida vacation experience. Spanning approximately 4,399 sq ft of living space on a nearly 6,000 sq ft lot, this home embodies the perfect blend of comfort and whimsy. Upon entering, you're greeted by an open-concept design that flows seamlessly into a gourmet kitchen equipped with an oversized island, ideal for both cooking and socializing. The dining area accommodates over 15 guests under modern, sculptural lighting—setting a chic stage for unforgettable gatherings. Each of the ten bedrooms is richly themed to honor beloved Disney characters and stories—from enchanting princess suites to daring adventure rooms—creating a personalized and immersive experience for every guest. The excitement continues upstairs with a Jurassic Park-inspired game and TV room, while the converted garage is home to an awe-inspiring Star Wars-themed game room, elevating entertainment to an intergalactic level. Step outside to discover your private oasis: a gorgeous pool fringed by sun-washed decking, offering serene relaxation and exclusivity. The property is nestled within the resort-style Windsor at Westside community, where residents enjoy access to stellar amenities—including a beach-style community pool, lazy river, water slides, clubhouse with fitness center and game room, tennis courts, mini-golf, volleyball, cornhole, and more. Conveniently located within close proximity to world-renowned theme parks, this estate offers not only a magical getaway but also a lucrative investment opportunity—especially appealing for short-term rentals, thanks to its unique theming, turnkey condition, and high guest appeal. This home is an active short term rental with transferable bookings!

Listing is courtesy of: EXP REALTY LLC (888-883-8509)

Listing Agent: Manny Lopez (305-213-7451)

Remarks: ***Price Reduced***Welcome to this fully furnished 5-bedroom, 4-bath townhome located in the highly desirable Windsor Island Resort, a community zoned exclusively for short-term rental use. The open-concept floor plan features a spacious kitchen with ample cabinetry and counter space, flowing seamlessly into the dining and living areas—perfect for accommodating vacation guests. The thoughtfully designed layout offers multiple en-suite bedrooms and well-appointed bathrooms, providing comfort and privacy for larger groups. Step outside to enjoy your private screened pool and covered outdoor eating area, perfect for relaxing after a day at the parks or hosting poolside meals. Guests will also enjoy full access to Windsor Island’s resort-style amenities, including a clubhouse, resort pool with lazy river, fitness center, playground, and more. Conveniently located just minutes from Walt Disney World, major attractions, shopping, and dining, this property consistently appeals to vacationers year-round. This short-term rental–approved townhome offers strong income potential in one of Central Florida’s most in-demand resort communities. A must-see for investors seeking a low-maintenance, high-demand vacation rental. Schedule your private showing today.

Listing is courtesy of: LUXURY ORLANDO REAL ESTATE (407-705-7634)

Listing Agent: Carl Johnson (407-705-7634)

Remarks: ONE-OF-A-KIND TOWNHOME WITH LUXURY DESIGN! Experience the pinnacle of opulence and comfort in this remarkable 5-bedroom, 4.5-bathroom vacation haven situated within an exclusive gated community in Orlando. This residence, a harmonious blend of style and functionality, offers a captivating escape for guests in the enchanting city. Nestled in a highly coveted neighborhood, the property not only provides convenience but also serenity. Set within a meticulously planned community, it ensures effortless access to Orlando's attractions while granting a peaceful retreat. Enter this carefully curated home, where each room in this 2023-built gem is intricately themed and impeccably designed, earning its place as one of the most aesthetically pleasing properties in the entire community. When not venturing into the wonders of Orlando, revel in ultimate relaxation within your private sanctuary. The residence boasts a complete leisure area, inviting you to unwind in unparalleled style. Whether lounging by the pool, engaging in friendly games in the opulent game room, or simply savoring the beauty of the landscaped surroundings, this vacation home guarantees an experience of unmatched luxury. Secure your private tour now and immerse yourself in the enchanting ambiance of this exquisitely adorned retreat.

Listing is courtesy of: ONLI REALTY GROUP LLC (352-278-8544)

Listing Agent: Annelise Pinto (407-413-6321)

Remarks: PREMIUM TURNKEY INVESTMENT- 100% RENTAL READY IN WINDSOR ISLAND! Avoid the massive upfront setup costs and months of delivery delays. This spectacular 5 BEDROOM, 5 DEDICATED ENSUITE BATHROOM resort luxury home is being sold fully furnished and professionally decorated. Half Bathroom leads out to Lanai. Engineered perfectly investor short-term rentals, the open layout leads directly to a private pool oasis. Located in Central Florida's top-tier resort community featuring a world class lazy river, clubhouse, and amenities. This pristine property is a true plug -and- play business asset. Seller requires a clean, and fast closing. Sold As-Is. Contact Listing agent today for booking history and secure this turnkey asset before the peak rental season!

Listing is courtesy of: CHAMPION HOMES (863-420-0007)

Listing Agent: Tammy Moore (352-636-2684)

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: MOTIVATED SELLER! Experience resort-style living in this beautifully maintained, fully furnished 5-bedroom, 4.5-bath Windsor Island townhome, lightly used exclusively as a personal vacation retreat and never subjected to the heavy wear of short-term rental turnover. With spacious en-suite bedrooms, a versatile loft area, and room for everyone to relax comfortably, this home is perfectly designed for both personal enjoyment and entertaining guests. Inside, you’ll find a bright open-concept floorplan featuring tile flooring throughout the main living areas, a spacious kitchen with granite countertops, stainless steel appliances, and a large center island ideal for gathering. The living and dining spaces flow seamlessly together and open through sliding glass doors to your private screened lanai and plunge pool, creating the perfect indoor-outdoor Florida lifestyle. The thoughtfully designed layout also includes an upstairs laundry room, generous storage, and plenty of parking for owners and guests alike. Located within the highly sought-after gated Windsor Island Resort community, residents and guests enjoy access to exceptional resort amenities including a zero-entry pool, lazy river, dual water slides, splash pad, poolside bar, fitness center, arcade, mini golf, playground, and an impressive clubhouse. Ideally situated near world-famous theme parks, championship golf courses, shopping, dining, major highways, and Orlando International Airport, this property offers an outstanding opportunity as a vacation home, investment property, or full-time Florida retreat.

Listing is courtesy of: REDFIN CORPORATION (407-708-9747)

Listing Agent: Alejandra Nicholson Pa (786-660-0340)

Remarks: 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.

Listing is courtesy of: HOMIQ REALTY LLC (407-577-0952)

Listing Agent: Erwin Isokaitis Junior (407-577-0952)

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: 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: Don’t miss your chance to own this stunning fully furnished vacation townhome in the highly sought-after Windsor Island Resort, ideally located just minutes from Orlando’s world-famous theme parks. Built in 2022, this turn-key 5-bedroom, 4.5-bath short-term rental offers an open-concept layout with a bright, airy great room overlooking the private pool, a seamless flow between the family room, dining area, and kitchen, and a beautifully appointed chef’s space featuring a large granite island, extended breakfast bar seating, stainless steel appliances, and stylish cabinetry. Sliding doors lead to the screened lanai and sparkling pool, perfect for outdoor gatherings, while a convenient half bath opens directly to the pool area. Upstairs, a spacious loft provides additional room for relaxation or family fun, and four well-sized bedrooms ensure comfort for everyone. As part of this premier resort-style gated community, you’ll enjoy world-class amenities including a lazy river, spa, dual waterslides, kids’ splash pad, resort-style pool, the Blue Marlin Grille on-site restaurant and bar, fitness center, basketball court, miniature golf, rental cabanas, and a fire pit. Whether you’re seeking a high-performing vacation rental or a move-in-ready residence, this home delivers the ultimate resort-style living just minutes from Disney and Central Florida’s top attractions—schedule your tour today.

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)

Remarks: Discover the epitome of luxury in Windsor Island Resort, one of the premier vacation home communities near Disney! This fully furnished residence offers 8 spacious bedrooms and 6 elegant bathrooms, with a sprawling open floor plan that caters to both relaxation and entertaining. The home's outdoor area is a private haven, featuring a screened-in heated pool and spa, along with a large lanai perfect relaxing or entertaining. Upon entering, you'll be greeted by a grand 2-story foyer and a beautiful staircase leading to the upper level. The fantastic kitchen boasts 42' cabinets, stainless steel appliances, and a lovely breakfast bar, and it flows seamlessly into the gathering room and dining area, opening through sliding doors to the outdoor living space. Indoor-outdoor living is effortless, whether for family gatherings or serene moments of tranquility. The first-floor layout is thoughtfully designed with the primary suite and an additional guest suite for ultimate convenience. The second floor offers a retreat-like ambiance with two private suites, two sets of Jack-and-Jill bathrooms, a spacious loft, and a versatile loft that can be used as a lounge, theater room or games room. The garage has also been converted into a fabulous game room for extra entertainment. This home showcases themed bedrooms, designed to ignite the imagination, and a dedicated game room to captivate guests of all ages. Windsor Island Resort enhances the experience with top-tier community amenities, including an 8,000-square-foot clubhouse, lazy river, heated pool, cabanas, sports courts, and more. Ideally located just minutes from Disney and major attractions, this property is perfect as a vacation rental investment or a dream getaway. Don’t miss this extraordinary opportunity to own a piece of paradise! Windsor Island Resort is a premier gated vacation community near Disney, offering unparalleled amenities and an unbeatable location. Residents can enjoy an 8,000-square-foot clubhouse, a heated pool with a relaxing lazy river, poolside cabanas, a fitness center, a restaurant and bar, a playground, mini golf, and courts for volleyball, tennis, and basketball. Additional perks include an arcade room and a cozy lounge area with TVs. The community provides convenient access to US 192 and I-4, placing Disney and other attractions just minutes away. The property also comes with transferable future bookings, and the seller is offering either the current furniture or a furniture upgrade tailored to the buyer's preferences. Windsor Island Resort is the perfect blend of luxury, comfort, and prime location!

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

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

Remarks: Check out this spacious townhome featuring 5 bedrooms and 4 bathrooms! Lightly used as a vacation home and short-term rental, it’s been kept in outstanding condition and feels barely lived in. Best of all, it’s completely turnkey — professionally themed, fully furnished, and ready for immediate use or rental income.The property has strong short-term rental appeal, and future bookings and revenue may even transfer with the sale. It’s also conveniently located just a short walk from the community’s main entertainment and amenity center, where owners and guests can enjoy tennis courts, pickleball, a water park, restaurant, playground, and park areas.The community offers 24/7 gated security with live guards and roaming patrols, giving residents and visitors extra peace of mind. Plus, the location is hard to beat — just minutes from Universal Orlando, Epic Universe, Walt Disney World, major shopping, top golf courses, Reunion Resort, ChampionsGate Town Center, and even a short drive to some of Florida’s best beaches. Priced competitively with excellent rental potential and strong investment upside, this is a fantastic opportunity for both investors and buyers looking for a vacation lifestyle property. The seller is motivated and open to considering all offers.

Listing is courtesy of: LA ROSA REALTY LLC (321-939-3748)

Listing Agent: Juan Delgado (407-744-4469)

Remarks: Fully furnished 6-bedroom, 4.5-bath vacation home located in the highly sought-after Windsor Island Resort. This spacious property features an open-concept floor plan, private screened-in pool and spa, themed bedrooms, game room, and modern kitchen with stainless steel appliances. The owner also invested in several builder upgrades including enhanced interior finishes and upgraded outdoor spa features, adding additional value and appeal to the home. Ideal as a short-term rental investment or vacation home. Windsor Island Resort offers world-class amenities including clubhouse, resort-style pool, lazy river, fitness center, sports courts, and more. Conveniently located near Disney, shopping, dining, and major attractions.

Listing is courtesy of: LINART REALTY, LLC (954-866-8936)

Listing Agent: Manzurul Haque (863-280-9814)

Remarks: MAJOR PRICE IMPROVEMENT AND BLOCKED FOR SHOWINGS! JUNE 7-18 & 22-30! BRING YOUR BUYERS!! Welcome to your dream vacation home in the highly sought-after Windsor Island Resort! This stunning turn-key 6-bedroom, 5-bathroom residence offers an unparalleled blend of luxury, entertainment, and investment potential—making it one of the best options on the market today. Designed with over $100,000 in premium design features and furnishings, this property is a lucrative short-term rental opportunity, ready to generate immediate income. Step inside and be amazed by the captivating media room, perfect for family movie nights, and game room style loft great for entertaining. The open floor plan flows effortlessly into a kitchen, complete with stainless steel appliances, and modern finishes. The primary suite is a private retreat with a spacious walk-in closet, while the five additional bedrooms—many with exciting Disney themes—create a magical experience for families and guests alike. Step outside to your own private oasis—a fully screened-in heated pool, offering plenty of space for relaxation and outdoor dining. Whether you’re hosting BBQs or soaking up the Florida sun, this backyard is built for enjoyment. Located in one of Orlando’s premier gated resort communities, Windsor Island offers resort-style amenities that set it apart from the competition, including a huge resort-style pool with a lazy river and water slides, a separate splash pool, a hot tub, volleyball and basketball courts, BBQ and picnic areas, and a state-of-the-art clubhouse with arcades, a bar and lounge, and more. Perfectly situated just minutes from Disney and a short drive to Universal Studios, shopping, dining, and entertainment, this home is the ultimate blend of vacation and investment. Don’t miss this incredible opportunity—contact us today to schedule a showing while it's temporarily vacant!

Listing is courtesy of: WATSON REALTY CORP. (407-589-1600)

Listing Agent: Renee Anthony (407-603-5935)

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: Welcome to an exceptional income-producing home located in the highly sought-after, guard-gated Windsor Island Resort in Davenport, Florida. This fully furnished 7-bedroom, 5.5-bathroom vacation pool home delivers an outstanding combination of luxury, comfort, and prime proximity to Orlando’s world-famous attractions. Ideal as an investment property or a personal getaway, this residence stands out for its thoughtful design and turn-key convenience. Step inside to a bright and spacious open floor plan perfect for hosting and accommodating large groups. The first-floor primary suite offers added privacy and convenient access for owners or guests. The home’s gathering spaces flow seamlessly into the modern kitchen, showcasing sleek cabinetry, stone countertops, stainless steel appliances, and a large island overlooking the living and dining areas. Upstairs features multiple ensuite bedrooms, themed guest rooms, and a generous loft that provides flexible space for entertainment, relaxation, or additional sleeping options. The layout is designed to comfortably support multi-family stays and vacation groups looking for ample room. Outdoors, the private screen-enclosed heated pool and covered lanai create the ideal setting for enjoying the Florida lifestyle year-round. Situated on a desirable corner lot, the property offers extra privacy and additional outdoor space, increasing both guest satisfaction and rental desirability. Located just minutes from Disney, Margaritaville, dining, shopping, golf courses, and major highways, this home is perfectly positioned to benefit from strong short-term rental demand. Whether you are expanding your portfolio or seeking a turn-key vacation retreat, this property represents a standout opportunity in one of Central Florida’s premier resort communities.

Listing is courtesy of: MARKET CONNECT REALTY LLC (407-250-4708)

Listing Agent: Maria Goris (407-916-6648)