Location: Windsor At Westside, Kissimmee
Do Not Show Listings
1861 NICE CT, KISSIMMEE, FL 34747
$577,000184 Days on yellowkey MLS ID: O6363676
REDUCED by $3,000 (0.5%) on 05/22/2026
Bed: 7 Bath: 5.5 Gar: 2 Liv Area Sq Ft: 3281 Built: 2018Monthly Fee: $563 Tax: $7,850 (2025)Community: Windsor At WestsideSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$7,850
Elementary School: None
High School: None
Tax Year: 2025
Middle School: None
Remarks: Short Sale. Price Reduction! Turnkey 7-Bedroom Vacation Home in Windsor at Westside – Active Short-Term Rental! Welcome to 1861 Nice Court, a beautifully furnished and actively producing 7-bedroom, 5-bathroom short-term rental located in the sought-after Windsor at Westside Resort. With 3,281 sq ft of living space, this stunning home is designed to impress guests and maximize occupancy—making it the perfect investment property or vacation retreat near the magic of Disney. Step inside to a bright, open-concept layout featuring a spacious living area, modern kitchen with stainless steel appliances, and generous dining space ideal for large families and groups. This home offers multiple ensuite bedrooms and themed guest rooms that delight visitors of all ages and keep bookings strong year-round. The private screened-in pool and patio provide the perfect place to unwind after a day at the parks, offering your guests the relaxation and resort-style experience they’re searching for. Located in the gated, 24-hour resort community of Windsor at Westside, owners and guests enjoy unmatched amenities including an 8,000+ sq ft clubhouse, fitness center, resort-style pool, waterslide, lazy river, volleyball court, tennis courts, and a full activity-filled play zone. The HOA covers lawn maintenance, internet, cable, daily valet trash service, and access to all resort amenities—making ownership truly hassle-free. Just minutes from Walt Disney World, Margaritaville, Sunset Walk, shopping, dining, and major attractions, this property offers strong rental history, excellent future booking potential, and a turnkey setup ready for its next owner. Whether you're looking to expand your STR portfolio or secure a high-performing vacation home, 1861 Nice Court is an exceptional opportunity in one of Central Florida’s premier resort communities.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Michael Steward (386-243-9585)
2402 DUBAI ST, KISSIMMEE, FL 34747
$460,000270 Days on yellowkey MLS ID: O6341750
Bed: 5 Bath: 4.5 Liv Area Sq Ft: 2263 Built: 2020Monthly Fee: $673 Tax: $7,189 (2024)Community: Windsor At Westside Ph 3Spa: NoTownhouse
Taxes:$7,189
Tax Year: 2024
Remarks: This is Windsor at Westside, your new home far from home! This beautiful townhouse features an amazing living room facing the desired pool you crave to see after a day of all the parks fun! INVESTMENT, this is the name of the game, this house has still books to come, which means money in your pocket. Upstairs, you will find 4 bedrooms with decorations ready to go.
Listing is courtesy of: FABIANO DIAS REALTY LLC (689-241-6853)
Listing Agent: Fabiano Dias (689-241-6853)
1987 MAJORCA DR, KISSIMMEE, FL 34747
$416,99918 Days on yellowkey MLS ID: O6397361
Bed: 4 Bath: 3.5 Gar: 1 Liv Area Sq Ft: 2263 Built: 2016Monthly Fee: $665 Tax: $7,682 (2025)Community: Windsor At Westside Ph 1Spa: NoTownhouse
Taxes:$7,682
Elementary School: Westside K-8
High School: Celebration High
Middle School: West Side
Remarks: INCOME-PRODUCING OPPORTUNITY in Windsor at Westside, one of Kissimmee’s most sought-after short-term rental communities near Orlando’s world-famous theme parks. Unlike many investment properties in the area, this FULLY FURNISHED and TURNKEY 4-bedroom, 3.5-bath townhome has been primarily owner-used and exceptionally maintained, offering investors and second-home buyers a rare combination of rental potential and pride of ownership. Designed for both guest appeal and long-term durability, the home features a highly functional layout with a private first-floor king suite and full bathroom, ideal for multigenerational stays and vacation guests seeking convenience and privacy. The open-concept living space showcases a modern kitchen with granite countertops, stainless steel appliances, and an oversized island that seamlessly connects to the spacious family room overlooking the private pool area. The covered lanai, complete with a convenient half bath, creates an ideal indoor-outdoor entertainment setting highly desirable in the vacation rental market. Upstairs, a versatile loft provides additional gathering space, complemented by three well-appointed bedrooms and two full bathrooms. This unit offers a one car garage, heated private pool with a pool bathroom and a florida room, and is located within a walking distance from a resort style club house. Whether you are seeking a proven income-producing asset, a second home with rental flexibility, or a well-maintained investment property in a high-demand tourism market, this residence offers exceptional value, location, and long-term potential.
Listing is courtesy of: NOBSKA REAL ESTATE LLC (689-276-1593)
Listing Agent: Laura Teixeira, Pa (941-962-2413)
2428 DUBAI ST, KISSIMMEE, FL 34747
$440,000651 Days on yellowkey MLS ID: O6233761
Bed: 5 Bath: 4.5 Liv Area Sq Ft: 2263 Built: 2020Monthly Fee: $605 Tax: $7,376 (2023)Community: Windsor At Westside Ph 3Townhouse
Taxes:$7,376
Tax Year: 2023
Remarks: Nestled Townhouse in Windsor at Westside, one of Kissimmee's premier short-term rental communities, this FULLY FURNISHED townhouse is your oasis of luxury and relaxation. With five spacious bedrooms and four and a half bathrooms, this stunning retreat offers the perfect blend of comfort and sophistication. As you step inside, you're greeted by an open floor plan that seamlessly integrates the living, dining, and kitchen areas. The kitchen boasts elegant granite countertops and sleek stainless steel appliances, creating a modern yet inviting atmosphere. The spacious loft upstairs provides an additional living area, perfect for relaxing, entertaining, or even setting up a home office. One of the highlights of this townhouse is the private pool, easily accessible through pool-facing telescopic sliding glass doors. Imagine unwinding by the poolside or retreating to the screened-in lanai for a serene evening under the stars. Staying in Windsor at Westside means enjoying world-class amenities. The HOA grants you access to an impressive 8,000 sq ft clubhouse, featuring a lazy river, sports courts, an arcade game room, and more. Dive into the zero-entry pool or treat yourself to a refreshing spa experience. Family will adore the playground and water slide, while adults can relax with a cocktail at the pool bar or dine at the full-service restaurant. To make your stay even more effortless, the HOA covers cable, high-speed internet, exterior maintenance, trash pick-up, pest control, and lawn care. Every detail has been thoughtfully curated to ensure your experience is nothing short of extraordinary. This townhouse isn't just a home; it's a lifestyle. Don’t miss out on the opportunity to own your own piece of paradise. Schedule a showing today and take the first step toward making this dream retreat yours.
Listing is courtesy of: SERHANT (786-296-8626)
Listing Agent: Gladys Bezerra (407-701-4034)
8801 RHODES ST, KISSIMMEE, FL 34747
$610,000448 Days on yellowkey MLS ID: O6289038
Bed: 8 Bath: 6.0 Gar: 2 Liv Area Sq Ft: 4041 Built: 2016Monthly Fee: $584 Tax: $12,143 (2024)Community: Windsor At Westside Ph 1Single Family
Taxes:$12,143
Remarks: Back on the market due to the buyer’s financing falling through. Welcome to this beautiful vacation home located in the highly sought-after Windsor at Westside community. This stunning property has an open floor plan and features 8 spacious bedrooms and 6 bathrooms, offering ample space for families or groups. The home is perfectly situated with easy access to Disney World® theme parks via the nearby toll road 429, making it an ideal choice for those visiting the magical parks. Additionally, there are a variety of dining and shopping options just a short drive away. The Windsor at Westside community itself is a resort-style retreat, with an array of amenities that will enhance your vacation experience. The incredible 10,000 sq. ft. clubhouse is the perfect spot to relax and unwind, while the community’s lake and pier have serene views and outdoor activities. For ultimate relaxation and fun, enjoy the zero-entry resort-style pool, complete with a thrilling waterslide, lazy river, and a water playground. This home is not just a place to stay; it’s a destination in itself, offering both luxury and convenience. Don’t miss the opportunity to make this dream vacation home yours!
Listing is courtesy of: INTOP REALTY LLC (407-233-5453)
Listing Agent: Hanna Zhang (407-601-8668)
2462 DUBAI ST, KISSIMMEE, FL 34747
$499,000277 Days on yellowkey MLS ID: FC312189
Bed: 5 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 2492 Built: 2019Monthly Fee: $722 Tax: $8,214 (2024)Community: Windsor At Westside Ph 3ASpa: NoSingle Family
Taxes:$8,214
Remarks: Welcome to your dream vacation and stunning fully furnished 5 bedroom, 4 bathroom pool home located on a corner lot in the highly sought after Windsor at Westside Resort. Perfectly designed for indoor/outdoor entertaining and is excellent income producing short-term rental or a fantastic personal retreat. Designed with lots of space in mind this two story layout and open floor plan is the perfect getaway. The home sleeps up to 14 comfortably and features large living areas with plenty of space for relaxing. The first floor master bedroom offers privacy and space, the kitchen has granite countertops and stainless steel appliances with a nice island opening to the dining room and living space. Enjoy the gated resort style amenities with the zero entry point pool, water slide, lazy river, and water playground. It boasts a clubhouse, a lake with a pier, fitness center, volleyball courts, sundry shop and video arcade. This is an ideal location as it offers easy access to Disney World attractions and many other theme parks in the area. Welcoming any and all offers.
Listing is courtesy of: BEACHES WITHIN REACHES REALTY (386-864-3154)
Listing Agent: Abby Baker (386-864-3154)
1844 GOBI DR, KISSIMMEE, FL 34747
$655,00081 Days on yellowkey MLS ID: O6389603
Bed: 6 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 3142 Built: 2018Monthly Fee: $606 Tax: $10,121 (2025)Community: Windsor At Westside Ph 2ASpa: YesSingle Family
Taxes:$10,121
Remarks: Priced to sell! This fully furnished 6 bedroom, 4.5 bathroom vacation home is already operating and generating short term rental income, featuring three themed bedrooms, a loft with a large projector screen for movie nights, and a private outdoor retreat with a pool and spacious patio for entertaining with no rear neighbors, creating the perfect setup to attract bookings and memorable guest experiences. Inside, the home offers a spacious open concept layout that connects the living room, dining area, and kitchen, creating an ideal gathering space for families and large groups. The kitchen is fully equipped with stainless steel appliances, granite countertops, a tiled backsplash, and espresso cabinetry, making it both stylish and functional for extended stays. Ceramic tile flooring throughout the main living areas on the first floor provides durability and easy maintenance, ideal for vacation rental use. The first floor features a primary bedroom with direct access to the pool area and a private en suite bathroom complete with a soaking tub and walk in shower. The garage has been converted into a game room with a pool table and foosball table, providing an additional entertainment space that guests love. Upstairs you will find an additional en suite bedroom, four more beautifully furnished bedrooms, and two additional bathrooms. The loft area creates the perfect gathering space and is highlighted by a large projector screen, making it ideal for movie nights, game days, or relaxing after a day at the parks. Step outside to enjoy the covered patio and private pool area, perfect for entertaining or unwinding in the Florida sunshine. With no rear neighbors, the backyard offers added privacy rarely found in vacation homes. Located just minutes from Central Florida’s world famous attractions, shopping, and dining, owners and guests also enjoy access to resort style amenities including a clubhouse, fitness center, resort pool with lazy river, bar, and game room, all within the highly desirable Windsor at Westside Resort. Book your private showing today.
Listing is courtesy of: REAL BROKER, LLC (407-922-8986)
Listing Agent: Brian Hamaoui (407-760-0975)
1885 GOBI DR, KISSIMMEE, FL 34747
$765,000105 Days on yellowkey MLS ID: O6383464
REDUCED by $5,000 (0.6%) on 05/19/2026
Bed: 8 Bath: 6.0 Gar: 2 Liv Area Sq Ft: 4041 Built: 2016Monthly Fee: $607 Tax: $11,612 (2025)Community: Windsor/Westside, Windsor At WestsideSpa: YesSingle Family
Taxes:$11,612
Remarks: Welcome to the Epic Universe House! Experience a truly immersive vacation lifestyle in this stunning 8-bedroom, 6-bathroom pool home located in the gated community of Windsor at Westside. Fully themed, recently renovated, and professionally designed, this turn-key residence pays tribute to the highly anticipated Epic Universe, featuring an arcade, a Nintendo World gaming room, and immersive themed bedrooms including Harry Potter, How to Train Your Dragon, Legend of Zelda, and more! Spanning over 4,000 sq ft, this spacious retreat perfectly blends modern elegance with family entertainment. The open-concept first floor features ceramic tile flooring, a chef’s kitchen with granite countertops, and an oversized island designed for large gatherings. Step outside to your private outdoor oasis—a screened-in lanai with a sparkling pool and spa overlooking a serene water view. Recent Upgrades: This home is being sold AS-IS and Fully Furnished, featuring high-end furniture and professional decor. It is a proven, high-performing vacation rental with a history of top-tier reviews making it the perfect addition to any investment portfolio. World Class Resort Amenties: Living in Windsor at Westside provides 24/7 gated security and access to a 10,000 sq ft clubhouse including: Resort-Style Pool & Interactive Splash Park, Winding Lazy River & Water Slide, State-of-the-Art Fitness Center, Tu Casa Bar & Lounge / Poolside Tiki Bar, Arcade Game Room, Multi-purpose Sports Courts, & Sand Volleyball, Sundry Shop & Playground Unbeatable Location: Located just minutes from Walt Disney World, Universal Orlando Resort, and the newly opened Epic Universe park, you are at the heart of Central Florida’s top attractions, world-class dining, and premium shopping. Don't miss the chance to own a piece of the magic! Schedule your private showing today and step into a world of epic possibilities.
Listing is courtesy of: PABLA PROPERTIES (407-967-2757)
Listing Agent: Sunny Pabla (407-967-2757)
2100 ROME DR, KISSIMMEE, FL 34747
$720,000180 Days on yellowkey MLS ID: O6365123
Bed: 7 Bath: 5.5 Gar: 2 Liv Area Sq Ft: 3314 Built: 2015Monthly Fee: $665 Tax: $9,833 (2025)Community: Windsor At Westside Ph 1 Pb 23 Pg 112-118 Lot 100Spa: YesSingle Family
Taxes:$9,833
Remarks: Welcome to this exceptional 7-bedroom, 5-bathroom vacation home located in the highly desirable Windsor at Westside Resort. This fully furnished property is turn-key and revenue-ready, offering a spacious and well-designed floor plan ideal for large families and short-term rental guests. The home features an open-concept main living area, a generous upstairs loft, a 2-car garage, and a private screened-in pool with heated spa for year-round enjoyment. The kitchen offers stainless steel appliances, stone countertops, and a large island with seating, flowing seamlessly into the dining and living spaces. With ample bedrooms—including multiple suites—and thoughtfully designed themed rooms, this residence provides comfort and functionality for owners and guests alike. Located within one of Orlando’s top short-term rental communities, Windsor at Westside offers outstanding resort amenities such as a full-service clubhouse, resort-style pool with lazy river, fitness center, tennis and basketball courts, sand volleyball, arcade, restaurant, and 24-hour gated security. Just minutes from Disney and Central Florida’s world-class attractions, this property is an excellent opportunity for investors or buyers seeking a high-performing vacation retreat.
Listing is courtesy of: MS LAND & BUILDING LLC (407-512-1213)
Listing Agent: Rubens Aranha (407-308-9094)
8906 ZURICH LN, KISSIMMEE, FL 34747
$559,00089 Days on yellowkey MLS ID: O6387866
2 Days Off yellowkey (back on 5/18/2026)
Bed: 6 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 3142 Built: 2019Monthly Fee: $577 Tax: $8,739 (2025)Community: Windsor At Westside Ph 3ASingle Family
Taxes:$8,739
Remarks: Beautiful vacation home, fully furnished, ready to start your rental business. Kissimmee's most desirable resort communities. Near Disney parks, major roads, restaurants and shops. Clubhouse with resort-style pool, lazy river, gym, bar, sports courts & more. Property is actively used as a short-term rental. Future bookings may convey with the sale. Buyer must honor all existing reservations currently in place after closing. All bookings and rental agreements will be transferred to the new owner.
Listing is courtesy of: TALENT REALTY SOLUTIONS (407-910-2020)
Listing Agent: Andreza Machado (407-988-6639)
8849 RHODES ST, KISSIMMEE, FL 34747
$660,000321 Days on yellowkey MLS ID: O6327522
3 Days Off yellowkey (back on 5/18/2026)
Bed: 8 Bath: 6.0 Gar: 2 Liv Area Sq Ft: 4041 Built: 2015Monthly Fee: $563 Tax: $11,592 (2024)Community: Windsor At Westside Ph 1Spa: YesSingle Family
Taxes:$11,592
Remarks: Under contract-accepting backup offers. A phenomenal vacation rental investment opportunity with great income potential! Discover this prime lot in the vibrant Windsor at Westside, perfectly nestled across from the clubhouse with stunning lake view. This impeccably maintained vacation home is fully furnished with upgraded furniture, including three lavish primary suites and fun themed bedrooms, perfect for large vacation groups. The home boasts newly upgraded luxury vinyl flooring in all bedrooms (NO carpet), sleek granite counter tops in the kitchen and bathrooms, premium stainless steel appliances, and stylish tiles. Dive into relaxation with a private screened pool, paver deck, and covered lanai, backing to a natural pond and conservation area. Energy-smart features like two high-efficiency AC units, LOW-E dual-pane windows, and modern appliances keep it eco-friendly and cost-effective. This guard-gated community dazzles with a 10,000-square-foot resort-style clubhouse with arcade game room, a sparkling heated pool and spa, a meandering lazy river, a thrilling mini water park, a cutting-edge fitness center, a lively tiki bar, and all sorts of sports fields. Landscaping, internet, cable, and daily valet garbage collection are included in the HOA fee. Just minutes from Walt Disney World, premier golf courses, vibrant shopping, the airport, and major attractions, this is your chance to own a slice of paradise for investment or 2nd home! Schedule your exclusive private tour today!
Listing is courtesy of: KELLER WILLIAMS CLASSIC (407-292-5400)
Listing Agent: Sherry Wang (484-744-4586)
1614 LIMA AVE, KISSIMMEE, FL 34747
$639,900383 Days on yellowkey MLS ID: S5126817
Bed: 8 Bath: 6.0 Gar: 2 Liv Area Sq Ft: 4041 Built: 2019Monthly Fee: $564 Tax: $12,328 (2024)Community: Windsor At Westside Ph 2BSpa: YesSingle Family
Taxes:$12,328
Remarks: Spacious 8-bedroom, 6-bathroom single-family home located in the gated community Windsor at Westside Resort. This two-story home offers a functional layout with an open-concept living and dining area, as well as a well-appointed kitchen featuring granite countertops, stainless steel appliances, and a large island for additional workspace. The main floor includes two bedrooms—one of which is an en-suite with direct access to the pool area—along with an additional full bathroom for convenience.Upstairs, you’ll find a true standout feature: your very own cinema room, designed for movie nights and unforgettable moments. A spacious loft offers even more room to relax and enjoy, along with additional bedrooms including a second and a third en-suite and fun themed rooms. The exterior of the home includes a private pool and spa, covered lanai, and patio area with outdoor seating. The pool area provides ample space for relaxation and recreation. Fully furnished and turn key ready. The Windsor at Westside Resort is a Gated Community with a great Clubhouse for vacationers, and features amenities including a lazy river, splash pool, bar, gym, game room and more. This is a great vacation home, very close to other area attractions. Schedule your visit NOW. Stunning Home.
Listing is courtesy of: FLORIDA SPIRIT HOMES (407-396-4441)
Listing Agent: Gabriel Silva Andrada (321-666-0301)
1744 LIMA AVE, KISSIMMEE, FL 34747
$589,00019 Days on yellowkey MLS ID: O6407493
Bed: 7 Bath: 5.5 Gar: 2 Liv Area Sq Ft: 3314 Built: 2017Monthly Fee: $607 Tax: $10,366 (2025)Community: Windsor At Westside Ph 2ASingle Family
Taxes:$10,366
Remarks: Experience the ultimate Orlando getaway in this beautifully appointed 7-bedroom, 5.5-bath vacation home located in the highly desirable Windsor at Westside Resort, just minutes from Walt Disney World and Central Florida’s top attractions. Designed for comfort, relaxation, and entertaining, this spacious villa is ideal for large families, vacation groups, or short-term rental investment opportunities. The home features an inviting open-concept layout with generous living spaces on both levels, providing plenty of room for everyone to gather and unwind. The upstairs loft offers an additional entertainment area complete with a large TV, comfortable seating, and ample space for movie nights or game days. Step outside to your private west-facing screened lanai where you can enjoy sunny Florida afternoons by the sparkling pool and spa, lounge poolside, or relax under the covered patio while taking in peaceful views. The equipped kitchen includes a breakfast bar, abundant cabinetry, and things needed for meal preparation. Bedroom accommodations include: First-floor primary suite with king bed and private ensuite bath Additional half bath on the main floor Second-floor king suite with ensuite bath Second-floor queen suite with ensuite bath One queen bedroom Two bedrooms with twin beds One bunk room featuring a twin-over-full bunk bed Shared full bathrooms conveniently located between secondary bedrooms All bedrooms include TVs and generous storage space Residents and guests of Windsor at Westside enjoy access to outstanding resort-style amenities, including a lazy river, water slide, resort pool, tiki bar, clubhouse, fitness center, arcade, sports courts, and hot tubs. Conveniently located near Disney World, Universal Studios, SeaWorld, championship golf courses, shopping outlets, dining, and entertainment. Measurements are approximate and should be independently verified. Some furniture has been updated
Listing is courtesy of: CORNERSTONE INTERNATIONAL PROPERTY GROUP LLC (407-334-7497)
Listing Agent: Helen Lei (407-371-1225)
2427 DUBAI ST, KISSIMMEE, FL 34747
$444,000426 Days on yellowkey MLS ID: S5123971
Bed: 5 Bath: 4.5 Liv Area Sq Ft: 2265 Built: 2020Monthly Fee: $591 Tax: $7,228 (2024)Community: Windsor At WestsideTownhouse
Taxes:$7,228
Remarks: Dive headfirst into paradise at 2427 Dubai Street, Windsor At Westside! Forget ordinary – this is your resort, a dazzling, delivering a 6.9% Cap rate to the current owner is this fully furnished 5-bedroom, 4.5-bathroom end unit townhome where luxury meets pure, unadulterated fun. Imagine: sun-kissed mornings by your private, screened-in pool, the cool water shimmering like a sapphire. But hold on, the adventure's just beginning! Picture this: lazy river drifts, piña coladas at the tiki bar, adrenaline-pumping workouts in the cutting-edge gym, and legendary sports court showdowns. This isn't just a home; it's a launchpad to Orlando's magic, where theme park thrills, culinary explosions, and retail therapy await, just minutes away! Sensational financials available on request!
Listing is courtesy of: TEAM DONOVAN (407-705-2616)
Listing Agent: James Donovan (407-705-2616)
1876 NICE CT, KISSIMMEE, FL 34747
$679,90097 Days on yellowkey MLS ID: O6385119
0 Days Off yellowkey (back on 5/14/2026)
REDUCED by $19,100 (2.7%) on 04/15/2026
Bed: 8 Bath: 6.0 Gar: 2 Liv Area Sq Ft: 4041 Built: 2017Monthly Fee: $607 Tax: $11,676 (2025)Community: Windsor At Westside Ph 2ASpa: YesSingle Family
Taxes:$11,676
Remarks: Under contract-accepting backup offers. Welcome to the ultimate Florida resort lifestyle! Positioned in the premier gated vacation community of Windsor at Westside Resort- this 8-bedroom, 6-bath lakeview home offers thoughtfully designed living space. This fully furnished, rental-ready home presents an outstanding opportunity for both savvy investors and families seeking a high-performing vacation property just minutes from Walt Disney World, dining, and premier shopping. Inside, the expansive open-concept design creates a seamless flow between the kitchen, dining, and main living areas — ideal for entertaining large groups. The oversized upstairs loft provides an additional gathering space perfect for movie nights, gaming, or relaxing after long days at the parks. Constructed in 2017, this residence embodies the Florida resort lifestyle. Step outside to your private heated pool and spa, perfectly positioned to capture sweeping lake views — one of the most sought-after settings within the community. Whether hosting guests or enjoying a quiet sunset, the outdoor space delivers both privacy and a true vacation atmosphere. Ownership includes access to Windsor at Westside’s impressive resort amenities, including a grand clubhouse, resort-style pool with lazy river and waterslide, tiki bar, fitness center, arcade, and more — enhancing both guest experience and rental appeal.Whether expanding your investment portfolio or securing a luxury vacation home, this property offers both lifestyle and income potential in one of Central Florida’s top-performing short-term rental communities. Sold fully furnished and rental-ready with future bookings conveying if you keep the rental company. Call for your showing today!
Listing is courtesy of: MAINFRAME REAL ESTATE (407-513-4257)
Listing Agent: Katie Bray (407-779-6677)
8909 BENGAL CT, KISSIMMEE, FL 34747
$629,00042 Days on yellowkey MLS ID: S5148316
1 Days Off yellowkey (back on 4/27/2026)
Bed: 8 Bath: 6.0 Gar: 2 Liv Area Sq Ft: 4041 Built: 2019Monthly Fee: $607 Tax: $11,657 (2025)Community: Windsor At Westside Ph 2BSingle Family
Taxes:$11,657
Remarks: Best priced fully furnished turnkey investment in Windsor at Westside Resort, one of the most sought after short term rental communities near Disney. This spacious 8 bedroom, 6 bathroom vacation home offers strong rental income potential and immediate operation. Features include open concept living area, two owner’s suites on first and second floors, dedicated game room, entertainment loft and private screened pool with spa, ideal for guest satisfaction and high occupancy. Resort amenities include clubhouse, lazy river, heated pool, fitness center, sports courts, restaurant and bar. Prime location near Disney parks, golf, shopping and dining.
Listing is courtesy of: BEKK HOMES LLC (407-342-8012)
Listing Agent: Carlos Selmo (407-342-8012)
1909 MAJORCA DR, KISSIMMEE, FL 34747
$445,00021 Days on yellowkey MLS ID: S5149758
Bed: 5 Bath: 4.5 Gar: 1 Liv Area Sq Ft: 2263 Built: 2016Monthly Fee: $580 Tax: $7,423 (2025)Community: Windsor At WestsideTownhouse
Taxes:$7,423
Remarks: Discover the pinnacle of Florida living in this stunning, fully furnished 5-bedroom, 4.5-bathroom townhome, nestled within the highly sought-after Windsor at Westside resort community. Turnkey and professionally designed, this property is thoughtfully appointed to host large groups in style and comfort—an exceptional opportunity for investors seeking a high-performing short-term rental, or for buyers searching for the ultimate vacation retreat. A standout feature you won't find in most resort homes? Your own private garage—a rare and valuable bonus that offers added convenience, secure storage, and an extra layer of everyday practicality that sets this property apart from the competition. For out-of-state owners and short-term rental investors, this home delivers true peace of mind: a whole-home leak defense system actively monitors for water issues and helps prevent costly damage when you're miles away, while a brand-new washer and dryer mean one less major appliance to worry about replacing down the road. Even better, the home is just steps from the clubhouse, resort pool, and full lineup of community amenities—putting the very best of Windsor at Westside right at your doorstep. And when you're ready for quieter moments, step outside to your own private, screened-in pool—a tranquil escape where you can unwind in complete privacy after a day of adventure. As an owner at Windsor at Westside, you and your guests enjoy access to a world-class amenity collection, including a resort-style main pool with children's splash pad, relaxing hot tub, lazy river, fully equipped fitness center, arcade, kids' activity room, and basketball and volleyball courts. Ideally situated just minutes from Walt Disney World, Universal Studios, and SeaWorld, the home also places you near premier dining, championship golf, and upscale shopping at The Florida Mall and nearby outlet centers. Don't miss your chance to own a slice of paradise in one of Central Florida's most prestigious gated communities—where magical memories and smart investment go hand in hand.
2438 TANGER DR, KISSIMMEE, FL 34747
$588,000248 Days on yellowkey MLS ID: O6347903
Bed: 7 Bath: 5.5 Gar: 2 Liv Area Sq Ft: 3314 Built: 2019Monthly Fee: $587 Tax: $9,467 (2024)Community: Windsor At Westside Ph 3Single Family
Taxes:$9,467
Remarks: Don’t miss this amazing opportunity to buy this beautifully 7 bedroom 5 1/2 bathroom FULL FURNISHED POOL HOME in the most desirable resort, fully screened HEATED POOL & SPA, makes it perfect for indoor/outdoor entertaining. Windsor at Westside is gated resort community , one of the favorite desired resort style communities around Orlando and Kissimmee. This community has it all, clubhouse, lake & pier, zero-entry resortstyle pool complete with a waterslide, lazy river, and Kid's water playground, fitness center, volleyball courts, a sundry shop, and a video arcade. This is an ideal location it offers easy access to Disney World® attractions and many others theme parks in the areas. This home sleep up to 14 comfortably and features an open concept floor plan with a large living area. With plenty space spread out for entertaining and relax throughout entire house. The first floor Master Bedroom offers privacy and space, the kitchen has granite countertops and stainless steel appliances. Heated pool and spa to enjoy it at any time of the day. Don't miss this great opportunity
Listing is courtesy of: DOUBLE PINES REALTY, LLC (954-756-1835)
Listing Agent: Richard Lee (954-756-1835)
8956 ZURICH LN, KISSIMMEE, FL 34747
$575,00024 Days on yellowkey MLS ID: O6406521
Bed: 7 Bath: 5.5 Gar: 2 Liv Area Sq Ft: 3314 Built: 2019Monthly Fee: $577 Tax: $9,051 (2025)Community: Windsor At Westside Ph 3ASingle Family
Taxes:$9,051
Remarks: Location, location!!!!This fully furnished, turn-key 7-bedroom, 5.5-bathroom home offers 3,314 sq ft at Windsor at Westside a Gated Community. Enjoy an open-concept kitchen with stainless steel appliances and large island, a first-floor primary suite, and a spacious upstairs loft with 6 Bedrooms and 4 bathrooms Step outside to your private pool with brick pavers, covered patio, and screened lanai This beautiful 7-Bedroom 5.5-Bathroom comes fully furnished to make is turnkey for vacation investment property or simply as second home. Windsor at Westside a Gated Community. Located about 10-15 minutes from Disney World. Owners and guests enjoy unmatched amenities including an 8,000+ sq ft clubhouse, fitness center, resort-style pool, waterslide, lazy river, volleyball court, tennis courts, and a full activity-filled play zone. The HOA covers lawn maintenance, internet, cable, daily valet trash service, and access to all resort amenities Come and see it for yourself!
Listing is courtesy of: EPIQUE REALTY, INC. (888-893-3537)
Listing Agent: Khadija Webber (407-592-2166)
2058 ROME DR, KISSIMMEE, FL 34747
$435,00097 Days on yellowkey MLS ID: O6385195
REDUCED by $15,000 (3.3%) on 05/09/2026
Bed: 5 Bath: 4.5 Gar: 1 Liv Area Sq Ft: 2263 Built: 2015Monthly Fee: $580 Tax: $7,931 (2025)Community: Windsor At Westside Ph 1Spa: NoTownhouse
Taxes:$7,931
Remarks: Seller may consider buyer concessions if made in an offer ~ Welcome to opportunity in the GUARD GATED ~ RESORT COMMUNITY of Windsor at Westside – a FULLY FURNISHED ~ TURN KEY 5-bedroom, 4.5-bath PRIVATE POOL townhome that books well as a short-term rental and is ready to generate income from day one! Thoughtfully designed and tastefully decorated, this home feels light, bright, fresh, and truly move-in ready. TILE FLOORS flow throughout the main living areas, complemented by crown molding that elevates the OPEN CONCEPT living and dining spaces. The modern kitchen is both functional and stylish, featuring STAINLESS STEEL APPLIANCES, a tiled backsplash, ample cabinet and counter space, recessed lighting, pantry storage, and a large ISLAND with bar seating under pendant lighting – perfectly positioned to overlook the living and dining areas, making staying connected and entertaining effortless. A built-in drop zone at the foyer adds convenience for guests arriving and departing, while the covered front entry enhances curb appeal. The flexible floor plan includes a MAIN FLOOR BEDROOM & FULL BATH – ideal for multi-generational stays or guests who prefer first-floor accommodations. Upstairs, you will find the generous PRIMARY SUITE, a secondary en-suite bedroom with its own private bath, and additional well-appointed bedrooms and bathrooms designed with comfort and functionality in mind. Step outside to your COVERED PAVER LANAI and PRIVATE SCREENED POOL – a must-have for today’s vacation rental guests – complete with a convenient poolside half bath. Whether guests are soaking up the Florida sunshine poolside or floating the lazy river at the clubhouse, this property delivers the FULL RESORT EXPERIENCE. In addition to your private pool, Windsor at Westside offers a stunning community pool, clubhouse, fitness center, restaurant, game room, and one of the area’s most sought-after lazy rivers – amenities that consistently attract repeat bookings. The 1-car garage adds storage and owner convenience, while the LOW MAINTENANCE townhome lifestyle makes this an easy choice for investors or vacation home/second-home buyers alike. Located just minutes from world-famous theme parks, championship golf courses, premier shopping and dining, and with easy access to US-27 and 192, Windsor at Westside remains one of Kissimmee’s sought-after short-term rental communities. If you have been searching for a well-performing, fully furnished, income-producing vacation home in a true resort-style community – this is the one! Call today for more information and schedule a tour!
Listing is courtesy of: WEMERT GROUP REALTY LLC (407-743-8356)
Listing Agent: Jenny Wemert (407-809-1193)
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