Location: Windsor At Westside, Kissimmee
Do Not Show Listings
2022 MAJORCA DR, KISSIMMEE, FL 34747
$399,9901 Day on yellowkey MLS ID: O6396215
Bed: 4 Bath: 3.5 Gar: 1 Liv Area Sq Ft: 2102 Built: 2015Monthly Fee: $665 Tax: $7,697 (2025)Community: Windsor At Westside Ph 1Townhouse
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$7,697
Elementary School: None
High School: None
Tax Year: 2025
Middle School: None
Remarks: Welcome to 2022 Majorca Drive, a highly desirable 4-bedroom, 3.5-bathroom townhome located in the Windsor at Westside Resort. Positioned in the preferred Phase 1 of the community, this home sits close to the clubhouse, resort-style lagoon pool, lazy river, bar & lounge, and a full range of premium amenities—an exceptional location that vacation guests consistently look for when booking their stay. Whether used as a personal getaway or an income-producing property, this townhome delivers the perfect combination of comfort, convenience, and resort-style living. Inside, the open-concept layout is ideal for entertaining, featuring a well-equipped kitchen with granite countertops, stainless steel appliances. A convenient outdoor half bathroom enhances the pool area—an extra feature that guests truly appreciate. Each bedroom is thoughtfully furnished to create a relaxing and welcoming atmosphere, making it ideal for vacation stays. Currently operating as a successful full-time short-term rental, the property is fully turnkey and ready to generate income immediately, or to be enjoyed as your own retreat near Orlando’s world-renowned attractions. Windsor at Westside is recognized as one of Central Florida’s premier resort communities. Residents and guests have access to a 10,000 sq. ft. clubhouse, a lagoon-style pool with lazy river and waterslide, fitness center, arcade, volleyball court, poolside Tu Casa bar & lounge, and 24-hour gated security. Ideally located just minutes from Walt Disney World, this property presents a rare opportunity to own one of the best-positioned townhomes in a highly desirable vacation community—offering strong rental potential, excellent guest appeal, and unmatched access to resort amenities. All information provided, including room measurements, is considered reliable but not guaranteed. Buyers and agents are advised to verify all details independently.
Listing is courtesy of: WRA BUSINESS & REAL ESTATE (407-512-1008)
Listing Agent: Alexandre Zapparoli (321-444-8701)
2108 MOROCCO WAY, KISSIMMEE, FL 34747
$614,9001 Day on yellowkey MLS ID: S5147141
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 1Single Family
Taxes:$10,059
Remarks: Welcome to 2108 Morocco, 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 6-bedroom 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. Currently projected to generate over $70,000 in revenue for 2026, with that number 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)
1788 LIMA AVE, KISSIMMEE, FL 34747
$580,0005 Days on yellowkey MLS ID: O6393893
Bed: 6 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 3142 Built: 2018Monthly Fee: $607 Tax: $10,221 (2025)Community: Windsor At Westside Ph 2ASingle Family
Taxes:$10,221
Elementary School: Westside K-8
High School: Celebration High
Middle School: West Side
Remarks: Epic 6-Bedroom Vacation Retreat in Windsor at Westside – Your Dream Getaway Awaits! Get ready to experience the ultimate Orlando escape! This jaw-dropping 6-bedroom, 5-bathroom luxury vacation home in the upscale Windsor at Westside Resort is your ticket to unforgettable memories with family and friends. Just minutes from world-famous theme parks like Disney, Universal Studios, SeaWorld, and Legoland, this home is all about location, comfort, and nonstop fun. Step inside and be wowed by a modern, stylish interior that’s spacious, fully furnished, and ready to impress. With room for everyone, from large families to big groups, this home is made for gathering—whether you're sharing a meal in the sleek, fully-equipped kitchen or kicking back in the open-concept living area after a day of adventure. But the real magic happens outside! Take a dip in your private pool and spa, dine alfresco under the covered lanai, or soak up the sun in total comfort. This outdoor oasis is perfect for lounging, entertaining, or just enjoying the Florida vibes. This home is steps away from the Windsor at Westside community, you’ll have exclusive access to top-tier resort amenities: A massive 10,000 sq. ft. clubhouse Zero-entry resort pool, lazy river, waterslide & kid's splash zone Free game room & high-energy play center Tu Casa Bar & Lounge with poolside cocktails and bites Whether you want to relax, recharge, or stay active, this resort has it all. This stunning home is turnkey and move-in ready, sold fully furnished—just bring your suitcase! It’s the perfect choice for a vacation home, short-term rental investment, or both. Prime location. Elite amenities. Endless fun. Don't let this rare opportunity slip away—schedule your private showing today and make this dream retreat yours! All information is believed to be accurate but should be independently verified by buyers and their agents.
Listing is courtesy of: FANNIE HILLMAN & ASSOCIATES (407-644-1234)
Listing Agent: Jeff Friedman (407-719-0135)
8851 GENEVE CT, KISSIMMEE, FL 34747
$410,00093 Days on yellowkey MLS ID: O6370265
5 Days Off yellowkey (back on 4/3/2026)
Bed: 5 Bath: 4.5 Liv Area Sq Ft: 2265 Built: 2018Monthly Fee: $580 Tax: $7,963 (2024)Community: WindsorTownhouse
Taxes:$7,963
Tax Year: 2024
Remarks: Under contract-accepting backup offers. Welcome to 8851 Geneve Ct in Kissimmee, a fully furnished, turn-key vacation home located in the highly sought-after Windsor at Westside Resort, one of Central Florida’s premier short-term rental communities near Walt Disney World Resort. This income-producing property offers the perfect blend of investment potential and resort-style living. Situated within a gated resort community, residents and guests enjoy world-class amenities including a lazy river, resort-style pool, clubhouse, fitness center, restaurant, playground, and multiple sports courts. The HOA provides exceptional value, covering basic internet and cable, landscaping for the common areas surrounding the unit, daily valet trash service, and full access to the resort’s amenities, including a kids splash pool area, lazy river, basketball and tennis courts, soccer field, volleyball courts, and an additional clubhouse located in Phase 3 of the resort. Security and guest access are well managed with 24/7 guard-gated entry across three guardhouses located throughout the community, additional guards during heavy check-in times, and overnight security rovers. Owners and guests also benefit from the MyQ gate access system, which provides proxy cards for owners and temporary access cards for guests for seamless entry. Ideally located just minutes from Disney and Orlando’s top attractions, with convenient access to U.S. Route 192, State Road 429, and Interstate 4, the home is surrounded by popular shopping, dining, and entertainment options that attract visitors year-round. Being sold completely furnished, this property is move-in ready*and ideal for buyers seeking a vacation home near Disney or a high-performing short-term rental property in Kissimmee’s thriving resort market.
Listing is courtesy of: KELLER WILLIAMS ADVANTAGE III (407-207-0825)
Listing Agent: Sofia Lovinsky (407-376-1845)
1979 MAJORCA DR, KISSIMMEE, FL 34747
$420,000318 Days on yellowkey MLS ID: O6311243
1 Days Off yellowkey (back on 2/5/2026)
Bed: 5 Bath: 4.5 Gar: 1 Liv Area Sq Ft: 2265 Built: 2016Monthly Fee: $516 Tax: $5,802 (2024)Community: Windsor At WestsideTownhouse
Taxes:$5,802
Remarks: This fully furnished 5-bedroom, 4.5-bath townhouse is located in the Windsor at Westside community. Features include a modern kitchen with granite countertops and stainless steel appliances, open concept living and dining areas, loft upstairs, and laundry room with cabinets. The property offers a heated, screened private pool, a one-car garage with alley access, and central air conditioning. Windsor at Westside amenities include clubhouse, lazy river, pools, sports courts, playground, arcade room, poolside bar and restaurant, and 24-hour security. HOA fees cover maintenance. Conveniently located near schools, shopping, and major highways.
Listing is courtesy of: THE FLORIDA LOUNGE REALTY LLC (786-241-7619)
Listing Agent: Glauco Pochine (407-600-8766)
1995 MAJORCA DR, KISSIMMEE, FL 34747
$419,000233 Days on yellowkey MLS ID: O6335963
Bed: 5 Bath: 4.5 Gar: 1 Liv Area Sq Ft: 2263 Built: 2016Monthly Fee: $531 Tax: $8,075 (2024)Community: Windsor At Westside Ph 1Townhouse
Taxes:$8,075
Remarks: Fully Furnished Turnkey Vacation Rental! This 5-bedroom, 4.5-bathroom vacation retreat is built for both relaxation and revenue—comfortably accommodating up to 16 guests and ready for immediate enjoyment or income potential! Ideally located just minutes from major theme parks, this property blends modern luxury with fun-filled amenities. On the main floor, you'll find a private king bedroom and full bathroom—perfect for multi-generational stays. The open-concept heart of the home features a stylish kitchen with granite countertops, stainless steel appliances, and a large island, flowing seamlessly into a bright, airy living room with views of the private heated pool. Step outside to a covered lanai and convenient outdoor half bath—ideal for entertaining. Upstairs, a spacious loft adds bonus living space, alongside four additional bedrooms and three full bathrooms. Two themed rooms—Frozen and Star Wars—feature custom murals and LED lighting, offering a magical experience for younger guests. Recent upgrades include fresh interior paint, a Nest thermostat, digital door locks, new lighting, plush carpeting, and high-end washer/dryer units. The detached garage provides flexible space for parking, storage, or a future game room or theater conversion. The HOA covers cable, internet, trash, lawn care, and access to resort-style amenities including a clubhouse, arcade,
Listing is courtesy of: KELLER WILLIAMS CLASSIC (407-292-5400)
Listing Agent: Scott Cohara (407-398-9554)
8849 RHODES ST, KISSIMMEE, FL 34747
$660,000262 Days on yellowkey MLS ID: O6327522
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 1Single Family
Taxes:$11,592
Remarks: 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 Agent: Sherry Wang (484-744-4586)
8912 BENGAL CT, KISSIMMEE, FL 34747
$679,90060 Days on yellowkey MLS ID: O6379285
3 Days Off yellowkey (back on 2/23/2026)
Bed: 10 Bath: 6.0 Gar: 2 Liv Area Sq Ft: 4391 Built: 2019Monthly Fee: $698 Tax: $12,169 (2025)Community: Windsor At Westside Ph 2BSingle Family
Taxes:$12,169
Remarks: Step into luxury resort-style living in this turn-key, fully furnished 10-bedroom, 6-bath pool home located in the highly sought-after Windsor at Westside community. Approved for short-term rentals, this property is a proven income-producer and an incredible vacation retreat all in one. Designed for comfort and fun, the home features a private pool with spa, an in-home movie theater, a game room upstairs, and two themed bedrooms created especially for Disney lovers. Every detail is set up for guests to arrive and start enjoying immediately. Windsor at Westside offers 24-hour guard-gated security and world-class amenities including a clubhouse, resort-style community pool, lazy river, splash zone, fitness center, arcade room, tennis courts, basketball courts, and volleyball courts. Lawn care, cable and internet are included, and the community is pet friendly. Whether you’re looking for a high-performing vacation rental or a spacious luxury getaway near the theme parks, this home checks every box. Call today before it's gone!
Listing is courtesy of: TAL BUSIDAN PA (407-227-3001)
Listing Agent: Tal Busidan (407-227-3001)
8811 GENEVE CT, KISSIMMEE, FL 34747
$410,0003 Days on yellowkey MLS ID: S5146973
Bed: 5 Bath: 4.5 Liv Area Sq Ft: 2263 Built: 2018Monthly Fee: $579 Tax: $6,358 (2025)Community: Windsor At Westside Ph 2BTownhouse
Taxes:$6,358
Remarks: Welcome to Windsor at Westside, one of Central Florida’s most desirable short-term vacation communities! Ideally located just minutes from world-famous theme parks, shopping, dining, and entertainment, this stunning 5-bedroom, 4 full bath and 1 half bath home offers the perfect blend of luxury and convenience. Fully furnished and move-in ready, this property is ideal as an income-producing vacation rental or a beautiful second home getaway. Enjoy your own private pool, perfect for relaxing after a day of fun in the sun. The community offers exceptional resort-style amenities, including a lazy river, water playground, cabanas, outdoor fireplace, shaded playground, fitness center, arcade, multi-purpose courts, sand volleyball, Tu Casa Bar & Lounge, event spaces, and a lush sports field. Don’t miss this incredible opportunity to own in a prime location just a short distance from Disney World parks—where comfort, entertainment, and investment potential come together!
Listing is courtesy of: MAGNUS REALTY GROUP LLC (407-286-6042)
Listing Agent: Manuel Minier (407-340-0966)
2440 TANGIER DR, KISSIMMEE, FL 34747
$525,00065 Days on yellowkey MLS ID: O6378202
0 Days Off yellowkey (back on 3/3/2026)
Bed: 5 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 2492 Built: 2019Monthly Fee: $587 Tax: $7,877 (2024)Community: Windsor At WestsideSingle Family
Taxes:$7,877
Remarks: Under contract-accepting backup offers. Located within the highly sought-after Windsor at Westside gated resort community, this fully furnished home offers flexibility as a primary residence, vacation getaway, or income-producing short-term rental. The property is already set up for Airbnb use and is being sold turnkey, allowing for immediate occupancy or continued rental operations. The home offers five bedrooms and four bathrooms, along with a game room and an open, airy floor plan designed for both comfort and functionality. The layout easily accommodates large groups, with multiple spaces to gather or unwind throughout the home. A private first-floor suite provides a quiet retreat, while the kitchen features modern finishes including granite counters and stainless steel appliances. Outdoors, a private pool to create the perfect place to relax at any time of day. Owners and guests enjoy access to a wide range of resort amenities, including a full-service clubhouse, lake and pier, expansive zero-entry pool, water slide, lazy river, splash area, fitness center, sports courts, arcade, and on-site convenience shop. Conveniently positioned near Disney and major attractions, this home combines location, lifestyle, and investment potential in one exceptional opportunity.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Caitlin Dos Santos (407-267-7196)
8900 PRAGUE WAY, KISSIMMEE, FL 34747
$590,000254 Days on yellowkey MLS ID: O6329265
Bed: 7 Bath: 5.5 Liv Area Sq Ft: 3314 Built: 2019Monthly Fee: $587 Tax: $9,677 (2024)Community: Windsor At Westside Ph 3Single Family
Taxes:$9,677
Remarks: Welcome to this stunning 7-bedroom, 5-bathroom pool home situated on a spacious corner lot in the highly sought-after Windsor at Westside Resort. Ideal for large families, multi-generational living, or short-term rental investment, this beautifully maintained home combines comfort, style, and resort-style amenities in a gated community just minutes from Disney and major attractions. The main floor features two generously sized bedrooms, including a primary suite with direct access to the private pool. Upstairs, you'll find five additional themed bedrooms—Harry Potter, Frozen, and Star Wars—plus a large loft that has been transformed into a movie room, perfect for family entertainment. Step outside to enjoy your own screened-in private pool and spa, complete with a child safety fence, offering the ideal setting for relaxation and fun. Residents and guests enjoy full access to world-class amenities, including a lazy river, splash pad, resort-style pools, tennis courts, fitness center, arcade, on-site restaurant, and a clubhouse—all secured with 24-hour gated entry. Conveniently located off US Hwy 192 and Toll Road 429, Windsor at Westside offers quick access to shopping, dining, and the “secret” west entrance to Disney via Western Way. Whether you're searching for a vacation retreat, or a high-performing investment property, this home is move-in ready and offers exceptional value in one of Central Florida’s premier resort communities. Don’t miss your opportunity to own a piece of the magic!
Listing is courtesy of: RATIO REAL ESTATE, LLC (407-674-0460)
Listing Agent: Veronica Li (407-674-0460)
8916 SYDNEY AVE, KISSIMMEE, FL 34747
$479,000966 Days on yellowkey MLS ID: O6133760
Bed: 5 Bath: 4.5 Liv Area Sq Ft: 2265 Built: 2019Monthly Fee: $560 Tax: $6,111 (2022)Community: Windsor At WestsideTownhouse
Taxes:$6,111
Tax Year: 2022
Remarks: Welcome to this beautiful home located at the unique Windsor At Westside. This 5 bedrooms, 4 full bathrooms and 1 half bathroom features an open plan family room, kitchen and dining area with sliding patio doors in the first floor and also one bedroom. In the second floor you'll find the other bedrooms and a very nice loft area to gatter your guests, family and friends in a private and exclusive area of the home. Property also includes a private pool. This is the perfect home in the most popular resort community that features one of the most amazing Clubhouse Amenities in the area. Just minutes away from world-famous Disney World.
Listing is courtesy of: SELECTA REALTY LLC (407-777-7131)
Listing Agent: Paulo Goncalves Ferreira (407-818-0717)
2014 MAJORCA DR, KISSIMMEE, FL 34747
$429,0006 Days on yellowkey MLS ID: S5146548
Bed: 5 Bath: 4.5 Liv Area Sq Ft: 2263 Built: 2015Monthly Fee: $579 Tax: $7,931 (2025)Community: Windsor At WestsideTownhouse
Taxes:$7,931
Remarks: Welcome to this 5-bedroom, 4.5-bathroom townhome with private heated pool located in the highly desirable Windsor at Westside — a premier short-term rental community just minutes from major highways, shopping, dining, and Central Florida attractions. This property is a competitive option within the community, featuring a private heated pool and a garage that can be converted into a game room, both highly desirable features for short-term rental performance. The home offers a functional open-concept layout, connecting the living, dining, and kitchen areas. The kitchen includes stainless steel appliances, granite countertops, and ceramic flooring. 1 bedroom on the first floor 4 bedrooms upstairs Spacious loft area Owner’s suite with walk-in closet and private bath Second-floor laundry room Enjoy a private screened-in pool and courtyard, ideal for relaxation and guest use. Community amenities include a resort-style pool, lazy river, clubhouse, fitness center, sports courts, tiki bar, and spa. Zoned for short-term rental, making it suitable for investment and vacation use, or primary residence.
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Ciro Noccioli Monteiro Alves (321-442-9680)
8825 CORCOVADO DR, KISSIMMEE, FL 34747
$699,9006 Days on yellowkey MLS ID: S5146750
Bed: 8 Bath: 6.0 Liv Area Sq Ft: 4041 Built: 2018Monthly Fee: $563 Tax: $11,733 (2025)Community: Windsor At Westside Ph 2BSingle Family
Taxes:$11,733
Remarks: TURN-KEY INVESTMENT OPPORTUNITY! 8-BED LUXURY POOL HOME JUST MINUTES TO DISNEY! Welcome to your ultimate dream vacation home or high-performing short-term rental (Airbnb/VRBO) located in the highly sought-after Windsor community! Perfectly designed to accommodate large groups and multiple families to maximize your rental income. HOME FEATURES: Step inside to a modern, open-concept floor plan with high ceilings that seamlessly connects the fully-equipped chef's kitchen, dining area, and spacious family room. Head outside to your private, screened-in lanai where you will find a sparkling pool and a relaxing SPA—the absolute perfect backyard oasis to unwind after a long day at the theme parks. RESORT-STYLE AMENITIES: Located in a premier, secure gated community, you and your guests will have access to world-class resort amenities. Enjoy the massive luxury clubhouse, resort-style pool, lazy river, fitness center, playground, and more! It truly offers a 5-star resort lifestyle. UNBEATABLE LOCATION: Location is EVERYTHING! Situated in the prime 34747 zip code, you are just a short drive to Walt Disney World, world-class golf courses, and fantastic dining options on Hwy 192. Easy access to major highways and Orlando International Airport (MCO). Whether you are looking to expand your lucrative investment portfolio or seeking the perfect family getaway home, this property checks all the boxes. Properties of this size and in this prime location do not last long—act fast!
Listing is courtesy of: MULTI CHOICE REALTY LLC (352-404-6542)
Listing Agent: Mingke Li (352-973-2303)
1861 NICE CT, KISSIMMEE, FL 34747
$580,000125 Days on yellowkey MLS ID: O6363676
Bed: 7 Bath: 5.5 Liv Area Sq Ft: 3281 Built: 2018Monthly Fee: $563 Tax: $7,850 (2025)Community: Windsor At WestsideSingle Family
Taxes:$7,850
Remarks: Short Sale. LOWEST PRICED 7 BEDROOM! 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 Agent: Michael Steward (386-243-9585)
8824 BENGAL CT, KISSIMMEE, FL 34747
$670,900169 Days on yellowkey MLS ID: O6353390
1 Days Off yellowkey (back on 3/28/2026)
Bed: 8 Bath: 6.0 Liv Area Sq Ft: 4041 Built: 2019Monthly Fee: $550 Tax: $12,811 (2024)Community: Windsor At Westside Ph 2B-1Single Family
Taxes:$12,811
Remarks: 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)
8931 ZURICH LN, KISSIMMEE, FL 34747
$549,0008 Days on yellowkey MLS ID: O6393822
Bed: 5 Bath: 4.0 Liv Area Sq Ft: 2492 Built: 2020Monthly Fee: $721 Tax: $7,587 (2025)Community: Windsor At Westside Ph 3ASingle Family
Taxes:$7,587
Remarks: A fantastic choice to be your Vacation Rental Property in the Windsor at Westside, located in Kissimmee Florida! 5 Bedrooms - 4 Bathrooms and your own Private Pool. Welcoming you inside is an amazing open floor concept that combines your living, dining and kitchen areas into one space. Also downstairs you will have an ensuite for your convenience. Upstairs you will find the loft, master bedroom ensuite with a large closet, one more ensuite and two more themed bedrooms and one bathroom. Also the laundry room is conveniently located upstairs. Granite countertops, light color cabinets, stainless steel kitchen appliances, themed bedrooms and much more. This home features a heated, private pool, a covered Lanai and pool deck area. The Windsor at Westside is a resort community and features a large Community pool, Lazy river, splash pool, gym, restaurant and much more. This is a great vacation home, very close to other area attractions.
Listing is courtesy of: TOPSKY REALTY INC (407-476-6189)
Listing Agent: Zhiming Xu (407-984-0087)
1603 LIMA AVE, KISSIMMEE, FL 34747
$699,00035 Days on yellowkey MLS ID: O6384770
Bed: 9 Bath: 6.0 Liv Area Sq Ft: 4391 Built: 2019Monthly Fee: $570 Tax: $12,172 (2025)Community: Windsor At Westside Ph 2BSingle Family
Taxes:$12,172
Elementary School: Westside Elem
Remarks: Located in the highly sought-after community of Windsor at Westside, 1603 Lima Avenue presents an exceptional FULLY FURNISHED short-term rental opportunity in one of Central Florida’s premier resort-style neighborhoods. Built in 2019 and offering over 4,300 square feet of thoughtfully designed living space, this 9-bedroom, 6-bathroom home comfortably accommodates 20 + GUESTS and has been meticulously upgraded with intricate, high-end theming that elevates the guest experience and drives strong rental performance. The property has a proven booking history with future reservations already in place that can convey to the new owner, making this a true turnkey investment. From the moment you enter, the home showcases a stylish and cohesive design that blends luxury with fun, immersive spaces. Each bedroom features its own unique theme, creating a memorable stay for guests of all ages. The expansive 675-square-foot upstairs loft functions as an additional entertainment hub, complemented by a private movie theater room that transforms nights in into a cinematic experience. The garage has been professionally converted into a fully outfitted game room. Outdoors, a private screened pool allows guests to relax and unwind after a day at the parks, offering the perfect balance of adventure and retreat. Located within the gated resort community of Windsor at Westside, residents and guests enjoy access to an exceptional collection of resort-style amenities designed to elevate the ownership and vacation experience. The community features a grand clubhouse, state-of-the-art fitness center, expansive resort pool with private cabanas, a lazy river, splash water park, and shaded lounge areas. Outdoor recreation includes tennis courts, pickle ball courts, basketball court, beach volleyball, soccer and multi-purpose fields, playgrounds, walking paths, and picnic areas. With 24-hour guard-gated security, beautifully maintained common areas, and a prime location just minutes from Central Florida’s world-renowned attractions, shopping, and dining, Windsor at Westside offers both lifestyle appeal and strong short-term rental desirability. The HOA includes lawn maintenance and daily trash valet service, helping to streamline operations and protect the overall community aesthetic. Offered fully furnished and professionally managed, this property is positioned for seamless ownership transition. Whether you are looking to expand your short-term rental portfolio or secure a luxury vacation home that generates income while you’re away, 1603 Lima Avenue delivers scale, style, and strong performance potential in one of the area’s most prominent resort communities.
Listing is courtesy of: EXP REALTY LLC (407-392-1800)
Listing Agent: Corinne Defilippis (941-807-7961)
9013 RHODES ST, KISSIMMEE, FL 34747
$651,90043 Days on yellowkey MLS ID: O6381275
Bed: 6 Bath: 4.5 Liv Area Sq Ft: 3142 Built: 2018Community: Windsor At Westside Ph 1Single Family
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Remarks: Located in the exclusive gated community of Windsor at Westside, this beautiful two-story residence, sold fully furnished, is the perfect combination of comfort, sophistication, and excellent investment potential. With 6 bedrooms, 4 full bathrooms, and 1 powder room, the house features a modern open-concept layout, providing spacious, integrated, and well-lit environments. Upon entering, a charming veranda with a garden welcomes you and creates a cozy atmosphere. Inside, you'll find a spacious living room with ceiling fans, integrated with the dining room and kitchen, forming an ideal environment for both everyday life and entertaining guests. Sliding glass doors lead to the outdoor area, where the private pool and covered veranda are located—the perfect space for leisure and relaxation. The kitchen is fully equipped with appliances, wooden cabinets, and a breakfast bar, combining practicality and elegance. The master suite is located on the first floor, offering privacy, a large bathroom, and a walk-in closet. On the second floor are the other five bedrooms—all with closets and carpeting—as well as a spacious loft that can be used as a TV room, game room, or additional living space. The condominium offers a complete resort-style structure, with a clubhouse, swimming pool, gym, volleyball courts, playground, game room, and security, providing leisure and convenience for the whole family. The location is privileged: just 15 minutes from Walt Disney World, close to golf courses, outlets, restaurants, supermarkets, and with easy access to the region's main highways. It is also about 30 minutes from Orlando International Airport, facilitating travel for domestic and international trips. Whether for living or investing in vacation rentals, this is a unique opportunity in one of Florida's most desirable areas.
Listing Agent: Rosania Taylor (407-580-6137)
8888 BENGAL CT, KISSIMMEE, FL 34747
$629,900171 Days on yellowkey MLS ID: O6351668
2 Days Off yellowkey (back on 3/26/2026)
Bed: 8 Bath: 6.0 Liv Area Sq Ft: 4041 Built: 2019Community: Windsor At Westside Ph 2BSingle Family
Remarks: Under contract-accepting backup offers. Experience resort living at its finest in this exceptional 8-bedroom, 5.5-bathroom home located in the highly sought-after Windsor at Westside community. Situated on a premium conservation lot, this fully furnished residence is ideal as a luxury vacation retreat or a short-term rental investment. The spacious open-concept layout features expansive living and dining areas, a gourmet kitchen with granite countertops and stainless steel appliances, and two master suites—one conveniently located on each floor. Step outside to enjoy the Florida lifestyle with your private screened-in pool and spa, offering serene tree-lined conservation views. Inside, guests will love the two themed bedrooms inspired by Star Wars and Disney Princesses, while the remaining rooms are tastefully decorated with quality furnishings and stylish accents to appeal to a wide range of guests. Residents and guests have access to world-class resort amenities, including a 10,000 sq. ft. clubhouse, resort-style pool with lazy river and splash pad, fitness center, arcade, sports courts, playground, and more. The HOA covers cable, internet, lawn care, and valet trash service for ultimate convenience. Perfectly located just minutes from Disney, shopping, dining, and major highways, this turn-key property is move-in or rental ready—a rare opportunity you don’t want to miss!
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