Location: Windsor At Westside, Kissimmee
Do Not Show Listings
8869 RHODES ST, KISSIMMEE, FL 34747
$559,000161 Days on yellowkey MLS ID: O6369898
REDUCED by $51,000 (8.4%) on 04/26/2026
Bed: 6 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 3142 Built: 2016Monthly Fee: $552 Tax: $11,004 (2024)Community: Windsor At Westside Ph 1Spa: YesSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$11,004
Elementary School: Westside Elem
High School: Celebration High
Tax Year: 2024
Middle School: West Side
Remarks: Ideally positioned within the highly sought-after Windsor at Westside resort community, this exceptional FULLY FURNISHED pool home offers an outstanding opportunity as the perfect blend of personal enjoyment and investment potential, whether used as a vacation home, seasonal escape, or profitable rental property. Walking distance from the community’s clubhouse, which offers resort-style amenities, this home combines prime location, strong rental performance, and extensive recent upgrades. This property is operating as an Airbnb and producing impressive revenue numbers when rented, driven largely by its ideal location within the community, beautiful water views in front and back, and the thousands of dollars invested into updates and improvements. Rental projections continue to look strong in the area, creating immediate income potential with room for future growth. For added convenience, any future bookings may be transferable if the current management company is retained, allowing for a seamless transition and potential day-one revenue for the next owner. Unlike many vacation homes on the market, this property has been extensively upgraded to maximize guest appeal and long-term durability. Featuring over $40,000 in improvements, the home includes luxury vinyl flooring throughout all bedrooms and upstairs living spaces, with NO CARPET except the updated stairway, along with refreshed furnishings and décor, fresh interior paint, new appliances, smart televisions, Nest thermostats, Schlage smart locks, LED lighting, security cameras, new linens, flatware, and more. Professionally themed bedrooms and upgraded entertainment spaces further enhance the guest experience. Spanning over 3,100 square feet, this spacious 6-bedroom, 4.5-bathroom home was designed for comfort, functionality, and entertaining. The open-concept layout flows seamlessly between the kitchen, dining, and living areas before opening to the private screened lanai with heated pool and spa. The thoughtfully designed floor plan includes two primary suites, including a first-floor owner's suite featuring dual sinks, soaking tub, and separate walk-in shower. Upstairs, additional guest rooms, themed spaces, and an oversized loft create the perfect entertainment area complete with a large-screen television and additional refrigerator. Outdoor living is equally impressive with upgraded patio furnishings, privacy screens, a pool alarm system, and a remote-controlled pool heater. Residents and guests of Windsor at Westside enjoy a 10,000-square-foot clubhouse, resort-style pool and spa, lazy river, water slide, arcade, tiki bar and restaurant, fitness center, sports courts, playground, and more. HOA dues include landscaping maintenance, cable, internet, pest control, daily valet trash service, and man gated security, creating a low-maintenance ownership experience, making it truly turn-key. Conveniently located just 20 minutes from Walt Disney World, shopping, dining, golf, major highways, 30 minutes from Orlando International Airport, and Florida’s world-famous attractions, this property truly checks every box for both lifestyle and investment performance. The hard work has been done for you! Schedule your private showing today and be sure to explore the virtual tour and 3D walkthrough links for a complete look inside this incredible property.
Listing is courtesy of: THE REAL ESTATE COLLECTION LLC (407-656-7814)
Listing Agent: Lisa Mahjoub (321-217-9965)
8936 SYDNEY AVE, KISSIMMEE, FL 34747
$445,000143 Days on yellowkey MLS ID: O6374304
Bed: 5 Bath: 4.5 Liv Area Sq Ft: 2263 Built: 2019Monthly Fee: $673 Tax: $5,571 (2025)Community: Windsor At Westside Ph 3Spa: NoTownhouse
Taxes:$5,571
Elementary School: None
High School: None
Tax Year: 2025
Middle School: None
Remarks: Beautiful fully furnished vacation home located in the highly desirable Windsor at Westside Resort. This property offers an open floor plan, private screened pool and spa, and access to world-class community amenities including clubhouse, resort-style pool, fitness center, playground, and sports courts. Zoned for short-term rental, making it ideal for investors or as a second home. Conveniently located near major highways, shopping, dining, and Orlando’s top attractions. HOA includes cable, internet, lawn care, and resort amenities. Buyer to verify all information, including rental restrictions and HOA requirements.
Listing is courtesy of: EMPIRE NETWORK REALTY (407-440-3798)
Listing Agent: Paula Maestrini (407-728-2666)
2108 MOROCCO WAY, KISSIMMEE, FL 34747
$589,90070 Days on yellowkey MLS ID: S5147141
0 Days Off yellowkey (back on 5/22/2026)
REDUCED by $5,000 (0.8%) on 05/15/2026
Bed: 6 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 3142 Built: 2017Monthly Fee: $563 Tax: $10,059 (2025)Community: Windsor At Westside Ph 1Spa: YesSingle Family
Taxes:$10,059
Remarks: Under contract-accepting backup offers. Ideally located in the main section of the highly sought-after Windsor at Westside, just a short distance from the community’s premier entertainment complex and resort amenities. This exceptional pool home presents an outstanding opportunity as a luxury vacation rental, personal retreat, or high-performing investment property. If you are looking for a completely turnkey property, this is the home for you. In only its first year as an active Airbnb this home is already producing strong revenue numbers primarily due to its location and the tens of thousands spent on recent updates. This IS that extremely turnkey home you’ve been looking for. Projections look fantastic and are expected to continue increasing, this property offers immediate and growing income potential. Even better, all future bookings are transferable if the current management company is retained, allowing for a seamless transition and day-one revenue. Inside, the home showcases tens of thousands of dollars in upgrades and custom theming, designed to maximize guest appeal and long-term durability. Featuring all tile and luxury vinyl plank flooring throughout with absolutely no carpet, this home combines style with easy maintenance. The spacious open-concept floor plan flows beautifully from the main living and dining areas to the private screened lanai with pool and spa, creating the ideal space for entertaining and relaxation. The kitchen is fully upgraded with stainless steel appliances, granite countertops, and a large island with seating, while the first-floor primary suite offers privacy and convenience. Upstairs, a generous media and entertainment space provides the perfect setting for movie nights, gaming, and guest enjoyment. Additional bedrooms include a second primary suite, beautifully appointed guest rooms, and professionally themed bunk rooms that elevate the vacation rental experience. Residents and guests enjoy access to one of Central Florida’s premier resort communities, featuring a 5,000-square-foot clubhouse, resort-style pool, lazy river, water slide, fitness center, tennis, basketball, volleyball, soccer field, kids play area, arcade, on-site restaurant, tiki bar, and shop. The HOA covers landscaping, internet, cable, and daily trash service, making ownership easy and hassle-free. Conveniently located near Walt Disney World, shopping, dining, golf, major highways, and Orlando’s top attractions, this property checks every box for both lifestyle and investment performance. Schedule your private showing today and secure one of the strongest opportunities currently available in Windsor at Westside.
Listing is courtesy of: AVANTI WAY REALTY LLC (305-229-1146)
Listing Agent: Jim Mcquade (407-906-6508)
2402 DUBAI ST, KISSIMMEE, FL 34747
$460,000280 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
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
$416,99928 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
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)
8801 RHODES ST, KISSIMMEE, FL 34747
$610,000458 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
$499,000287 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
$655,00091 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)
2100 ROME DR, KISSIMMEE, FL 34747
$720,000190 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
$559,00099 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)
1614 LIMA AVE, KISSIMMEE, FL 34747
$639,900393 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
$589,00029 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
$444,000436 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
$679,900107 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)
1909 MAJORCA DR, KISSIMMEE, FL 34747
$445,00031 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.
2058 ROME DR, KISSIMMEE, FL 34747
$435,000107 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)
1869 NICE CT, KISSIMMEE, FL 34747
$455,000115 Days on yellowkey MLS ID: O6383451
REDUCED by $4,000 (0.9%) on 05/09/2026
Bed: 5 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 2492 Built: 2019Monthly Fee: $697 Tax: $8,805 (2025)Community: Windsor At Westside Ph 2ASingle Family
Taxes:$8,805
Remarks: Welcome to tastefully designed 5/bed 4/bath home with private pool facing conservation area in the prestige Community Windsor at Westside, zoned for short term vacation rental. The open floor plan seamlessly connects the living, dining, and kitchen areas, perfect for everyday living and entertaining. There is a master bedroom on the first floor and upstairs you’ll find another spacious master bedroom and additional bedrooms for privacy and comfort. Residents can enjoy world-class resort amenities, including an 8,000 sq. ft. clubhouse, heated pool, lazy river, spa, volleyball and basketball courts, and on-site restaurant and bar. The home is just minutes from Disney Parks and other Orlando attractions.
Listing is courtesy of: TOPSKY REALTY INC (407-476-6189)
Listing Agent: Eileen Li (407-765-2589)
8824 BENGAL CT, KISSIMMEE, FL 34747
$670,900238 Days on yellowkey MLS ID: O6353390
Bed: 8 Bath: 6.0 Gar: 2 Liv Area Sq Ft: 4041 Built: 2019Monthly Fee: $550 Tax: $12,811 (2024)Community: Windsor At Westside Ph 2B-1Spa: YesSingle Family
Taxes:$12,811
Remarks: Short Sale. Make your dream a reality. Enjoy this Luxury, conveniently located, Central Florida lifestyle Home. Property can be, and currently is, used as a short-term vacation rental.
Listing is courtesy of: VMY REALTY INC (407-412-4164)
Listing Agent: Eugene Vilkovskiy (407-412-4164)
8869 BENGAL CT, KISSIMMEE, FL 34747
$489,00038 Days on yellowkey MLS ID: O6404732
Bed: 5 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 2492 Built: 2019Monthly Fee: $607 Tax: $9,465 (2025)Community: Windsor At WestsideSpa: YesSingle Family
Taxes:$9,465
Remarks: CORNER LOT! Why wait for a new home to be built, when you can buy this fully furnished, turn-key VACATION HOME in the sought-after gated community of Windsor at Westside! Excellent Income Producing SHORT-TERM RENTAL Home. ONLY 10 MINS from Disney Gate! Fully furnished and professionally decorated two-story home with a private pool. This 5 bed/4 bath Winstone model features a spacious great room and kitchen with granite Island, allowing for ample seating and space to entertain. The sliding doors lead to your own private oasis with a covered, screened lanai with pool. One Guest Bedroom/Bath downstairs. Enjoy the myriad benefits of a resort-style community and have a blast! You'll have access to a fantastic clubhouse, a heated pool and spa, wireless internet on the pool deck, a lazy river, a state-of-the-art fitness center, a playground, a game room, and much more - all designed for families to relish for hours! The HOA takes care of landscaping maintenance, provides internet and cable services, and offers daily valet garbage disposal for your convenience. Located just a short distance from Highway 192, this charming short-term rental community provides easy access to major highways like I-4 and US-27. Plus, it's just a stone's throw away from theme parks, attractions, shopping malls, outlets, local restaurants, and grocery stores. Don't miss out on this fantastic opportunity to own a piece of the vacation rental market in the heart of Kissimmee!
Listing is courtesy of: RATIO REAL ESTATE, LLC (407-674-0460)
Listing Agent: Veronica Li (407-674-0460)
8877 BENGAL CT, KISSIMMEE, FL 34747
$565,00039 Days on yellowkey MLS ID: O6402816
Bed: 5 Bath: 5.5 Gar: 2 Liv Area Sq Ft: 2622 Built: 2019Monthly Fee: $607 Tax: $9,316 (2025)Community: Windsor At Westside Ph 2BSpa: NoSingle Family
Taxes:$9,316
Remarks: Spacious 5-bedroom, 5.5-bathroom pool home located just 8 miles from Walt Disney World. This open-concept property features a modern kitchen equipped with stainless steel appliances, granite countertops, and a large island overlooking the dining and living areas. The floor plan includes a convenient primary suite on the main level. Upstairs, you will find additional well-appointed en-suite bedrooms, including themed rooms and a master suite. The exterior offers a private, fully screened-in patio with swimming pool. Significant features include high-speed Wi-Fi capability, a dedicated laundry room with full-sized washer and dryer, and keyless entry for seamless access. Situated in a luxury community with easy access to I-4, 192, and local dining, shopping, and grocery stores including Publix and Walmart. Excellent opportunity for a second home, or short-term rental investment. Sold fully furnished and move-in ready.
Listing is courtesy of: CELEBRITY GLOBAL REALTY LLC (407-530-9264)
Listing Agent: Alessandra Dale (407-729-6936)
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