Homes For Sale in Kissimmee 34747 - 886 homes

Remarks: This elegant and stunning, custom home was built in 2000 by the award-winning builder, ISSA Homes and recently fully renovated to a modern and luxurious standard. No detail was missed, and no expense spared in this one-of-a-kind home which was originally built for the builder himself. The interior of the estate includes spacious living areas, 6 bedrooms, as well as 6- and one-half baths, two with bidets. The second level West Wing, accessible via an intricately decorated elevator, is complete with a large master suite along with two bedrooms and two full baths. In the lower-level East Wing you will find a gourmet kitchen, living spaces, bedroom with full bath, and large laundry room. An in-law suite with separate entrance has two bedrooms, a full kitchen, bathroom, and laundry space. The storage is abundant in this spacious home. The 3rd floor has been converted to a full cinema room. The property has attached and detached double garage with room for four vehicles. Take a look from the many porches for a view of the beautifully landscaped estate, golf course, and sparkling pond and a one-of-a-kind oversized pool, spa, and waterfall. Enjoy drinks looking over the 13th hole or from the hidden garden under the oak tree. Enjoy outdoor living with a fully equipped outdoor kitchen, with Italian pizza wood burning oven.

Listing is courtesy of: GO FLORIDA REALTY, INC. (407-612-6139)

Listing Agent: Steven Trowsdale (407-520-6929)

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)

Remarks: Welcome to this beautifully updated beach-themed oasis, a fully renovated and furnished STR home located in the heart of Kissimmee. This property underwent a complete renovation in 2022, featuring a modernized kitchen with updated cabinetry, countertops, and appliances, along with new flooring and fresh interior paint throughout. Major capital improvements include a new roof (2022) and a recently resurfaced private pool (2025), offering peace of mind and long-term value. Designed for both comfort and functionality, each bedroom features its own dedicated full bathroom, providing privacy and convenience for guests—an setup for STR and multi-family use. The home also includes a converted garage game room equipped with ping pong, foosball, and arcade games, creating a fun and engaging entertainment space that enhances guest experience and rental appeal. The open-concept layout flows seamlessly to a screened-in lanai and private pool area, delivering the indoor-outdoor living experience for entertaining or relaxing after a day at nearby attractions. Located just minutes from Walt Disney World, shopping, dining, and major highways, this home is perfectly positioned for both strong STR income potential and long-term appreciation. The HOA provides exceptional value, including lawn service, irrigation maintenance, daily valet trash pickup, internet, basic cable, and a 24/7 manned guard gate for added security and convenience. Residents and guests enjoy access to a resort-style amenity package, including a large clubhouse, tropical community pool with water park slide and zero-entry access, open-air lounge, convenience store, fitness center, movie theater, billiards/game room, table tennis, lighted basketball and tennis courts, sand volleyball court, putting green, RV/boat parking area, and multiple playgrounds.

Listing is courtesy of: BEYCOME OF FLORIDA LLC (804-656-5007)

Listing Agent: Steven Koleno (804-656-5007)

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)

Remarks: Discover this fully furnished and recently renovated 3-bedroom, 2-bathroom second-floor condo in the gated resort community of Windsor Palms. The home features a beautifully updated kitchen with new cabinets and countertops, luxury vinyl flooring in the main living area, and a functional split floor plan with the primary suite separate from the additional bedrooms. Tasteful décor throughout makes this condo truly turnkey for personal use or short-term rental. Windsor Palms offers a full range of resort amenities, including a swimming pool, hot tub, splash pad, fitness center, movie theater, business center, convenience store, and courts for tennis, basketball, volleyball, and beach volleyball. Additional perks—such as table tennis, BBQ picnic areas, and scenic walking paths—provide endless ways to enjoy the Florida lifestyle. Ideally located just minutes from Disney World and close to major highways, this property ensures quick access to Orlando’s attractions, as well as nearby dining and shopping options. Don’t miss the chance to own a beautifully updated condo in one of the area’s most desirable resort communities. Schedule your showing today.

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

Listing Agent: Corey Smallman (407-744-2765)

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)

Remarks: Experience the ultimate vacation retreat and investment opportunity at 1576 Nassau Point Trail in the highly sought-after Solara Resort! This stunning 9-bedroom, 6.5-bath fully furnished pool home generated over $100,000 in rental income from Jan 2025–Jan 2026 and is completely turn-key and rental ready. Built in 2019, the home features an upgraded luxury furniture package, private movie theater, spacious game room loft, custom bar area, themed bedrooms, and expansive open-concept living spaces designed for unforgettable guest experiences. Step outside to your private screened-in oasis featuring a sparkling pool, spa, and extended sun deck — perfect for relaxing after a day at the parks. Located just minutes from Walt Disney World and Orlando’s top attractions, this property offers both luxury and convenience. Owners and guests enjoy access to Solara Resort’s incredible world-class amenities including the FlowRider® surf simulator, resort-style heated pool, splash pad, fitness center, sports courts, on-site dining, and 24/7 gated security. Whether you're looking for a high-performing short-term rental investment or a dream vacation home, this exceptional property checks every box!

Listing is courtesy of: HOLIDAY REALTY LLC (321-278-5486)

Listing Agent: Bryan Rogers (321-278-5486)

Remarks: Turnkey investment opportunity in a highly sought-after resort-style community just minutes from Disney World! This fully furnished home is a heavily booked short-term rental with strong income potential and future bookings in place. Designed to stand out, the property features themed rooms including a Frozen-inspired bedroom and a Star Wars-themed room with immersive LED lighting, creating a memorable guest experience that drives repeat bookings. The garage has been professionally converted into a game room, perfect for entertainment and maximizing rental appeal. Recent updates include new vinyl flooring in the loft, adding a fresh, modern touch to the living space. The open layout, spacious bedrooms, and private accommodations make this home ideal for large groups and vacationing families. Located just minutes from world-class attractions, dining, and shopping, this property offers both a fantastic personal getaway and a income-producing asset. Bookings, financials, and rental history available upon request!

Listing is courtesy of: SPECTRUM GLOBAL REALTY, INC (407-770-0067)

Listing Agent: Nisha Mehta (407-462-9297)

Remarks: AMAZING FULLY FURNSIHED VILLA AVAILABLE FOR SALE AT MARGARITAVILLE RESORT ORLANDO! This CORNER VILLA has 4 Bedrooms and 3 Baths, High-End Quartz Countertops, Upgraded "Wood" Tile Flooring and Appliances. Kitchen has Island with Seating, Large Counter Space and Windows with Lots of Natural Light. Master Bedroom Located Upstairs has En Suite Bathroom. Each of the Bedrooms has Ceiling Fans. Backyard has a Beautiful Paved Patio with Tropical Foliage! High Capacity Washer and Dryer. This is a Wonderful Community to Live in Full Time, Own a Second Home or Invest in a Vacation Rental Property! Includes Furniture, Blinds, Drapes, TVs, Artwork, Kitchen Necessities, Dishware, Linens, and so MUCH MORE! Unique First of its Kind Resort with Multiple Pools, Gym, On-Site Water Park, Sunset Walk Restaurants Bars, Live Music, Retail, Live Music and More! LOCATED MINUTES FROM DISNEY! It's A Great Lifestyle Choice For Those Who Want To Experience The Best Of Florida Living!

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

Listing Agent: Suzanne Docobo (954-304-4932)

Remarks: Priced to Sell! Motivated Seller! Stunning 6BD/4.5BA villa, professionally designed, truly a gem at this price! Fully furnished and ready to generate attractive short-term rental income. Enjoy a private pool, modern layout, and access to Solara Resort’s top-tier amenities, heated pool, surf simulator, gym, bar & grill, and more. HOA includes internet, landscaping, and full access to resort perks.

Listing is courtesy of: SINGULAR REALTY LLC (407-999-6899)

Listing Agent: Juliana Martins (786-546-6195)

Remarks: Welcome to an extraordinary opportunity in the highly sought-after Solara Resort in Kissimmee, Florida. This impeccably appointed 5-bedroom, 4.5-bath townhome is a true statement of luxury, offering an exceptional furniture and professionally decorated by an interior decorator curated for both elegance and comfort. Whether as a private retreat or investment property, this townhome delivers an elevated vacation experience. From the moment you step inside, you are greeted by a open-concept layout featuring a designer kitchen with modern finishes, an elegant dining space, and a beautifully styled living room that flows seamlessly for effortless entertaining. Every detail has been thoughtfully selected — from statement lighting to premium finishings — creating a warm yet refined ambiance. The primary ensuite is conveniently located on the main floor, providing privacy and convenience. A stylish half bath with direct access to the private pool area enhances functionality for guests enjoying the outdoor oasis. The covered patio and private pool create the perfect setting for relaxation after a day at the parks. Upstairs, a spacious loft offers a secondary lounge or entertainment space. The upper level features two additional ensuite bedrooms and two more exquisitely themed bedrooms that share a full bath. Each themed room has been professionally designed to captivate all guests, making this home especially desirable for short-term rentals. A dedicated laundry closet completes the second floor for added convenience. Smart Thermostat, Private Pool and much more. Located just moments from the Solara resort clubhouse, residents and guests enjoy access to world-class amenities including a resort-style pool, fitness center, sports courts, dining options, and entertainment areas.

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

Listing Agent: Ana Daviglus (407-463-3311)

Remarks: Welcome to a truly unparalleled luxury estate, nestled on 5 acres of serene privacy. This custom-built masterpiece, completed in 2009, boasts an impressive 11,138 square feet of meticulously designed living space, where every detail has been thoughtfully curated for the discerning homeowner. As you enter through the private gate, you are greeted by a stunning family room featuring a handcrafted stone gas fireplace and soaring ceilings that create an inviting atmosphere. The elegant curving marble staircase, adorned with a magnificent Swarovski crystal chandelier, sets the tone for the opulence that awaits. This estate offers 5 spacious bedrooms, each with large walk-in closets and en-suite bathrooms, ensuring comfort and privacy for family and guests alike. The main living areas are enhanced by exquisite woodwork, including a gorgeous dining room and a living room that seamlessly connects to the outdoor oasis through sliding glass doors that open at the corner, perfect for entertaining. Indulge in the ultimate entertainment experience in the media room, complete with luxurious seating and a stunning chandelier commissioned from Tiffany's in New York. The primary suite is a true retreat, featuring a cozy sitting area and an expansive closet. Additional highlights include a gym with a steam room, an office/study/library, and an upstairs game room that overlooks a spacious covered balcony. The outdoor amenities are equally impressive, featuring a large pool with a spa, ample undercover seating, an outdoor kitchen, and tennis courts, all surrounded by lush landscaping and majestic oak trees. The estate also includes a wine cellar, a wet bar with custom woodwork, and coffered ceilings adorned with unique prints. With a 4-car side garage and an attention to detail that is truly one of a kind, this estate is unlike anything you have ever seen. Experience luxury living at its finest—schedule your private tour today and discover the extraordinary lifestyle that awaits you.

Listing is courtesy of: THE AGENCY FL (407-335-4119)

Listing Agent: Brian Hyser (407-951-2472)

Remarks: Exceptional opportunity to own a fully furnished, income-producing 1-bedroom, 1-bathroom condo located on the 4th floor of Building 1, the main building at Embassy Suites by Hilton Orlando Sunset Walk—home to the front desk check-in and fitness center, offering unmatched convenience for guests and owners. This turnkey unit features a private balcony and is designed for both personal use and strong rental performance. Positioned within a professionally managed hotel program, this property delivers a true hands-off investment experience, ideal for investors seeking passive income in one of Central Florida’s most in-demand vacation destinations. Residents and guests enjoy access to premium resort-style amenities, including a spectacular Beach Club with resort pool, on-site bar and grill, 24/7 fitness center, and full-service hospitality. Located just minutes from Walt Disney World, Margaritaville, top-rated dining, shopping, and entertainment, this property sits in a high-traffic tourist corridor with year-round demand. Perfect for investors or vacation home buyers looking for location, convenience, and income potential. Don’t miss this opportunity—schedule your private showing today.

Listing is courtesy of: EMPIRE NETWORK REALTY (407-440-3798)

Listing Agent: Fabian Querales Perez (407-486-9655)

Remarks: Discover this exceptional, fully furnished 8-bedroom, 7-bathroom luxury home located in the highly sought-after Encore Resort at Reunion—a premier vacation home community just minutes from Walt Disney World. This spacious residence features an open-concept living, dining, and kitchen area with granite countertops and solid wood cabinetry throughout, creating an inviting space for large gatherings. The thoughtfully designed layout includes two bedrooms on the first floor, one with an en-suite bath, while the second level offers an additional living area and six more bedrooms, including two primary suites, two bedrooms connected by a Jack & Jill bath, and the remainder with private en-suites. Entertainment is at the forefront with a fully converted game room in the garage featuring table tennis, shuffleboard, mini basketball, a card table, and a TV. Step outside to your private oasis complete with a heated pool and spa, covered patio dining area, grill, and lounge seating—perfect for enjoying the Florida sunshine. As part of Encore Resort, guests and owners enjoy access to a 10-acre private water park with thrilling slides, a lazy river, and splash zones, along with on-site dining, fitness facilities, sports courts, arcade, and daily activities, making this property a true resort-style experience. Whether you're seeking a turnkey investment or a luxurious vacation retreat, this home delivers the ideal blend of comfort, entertainment, and location.

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

Listing Agent: Frank Baloun (407-488-4969)

Remarks: Indulge in Luxury Living at Encore Reunion! Welcome to this stunning 2-story home, located in the exclusive, sought-after community of Encore at Reunion. Renowned for its private waterpark and world-class amenities, Encore is the ideal place for relaxation and adventure. Nestled on THE LARGEST LOT in the community, this Grand Pool home offers the perfect balance of comfort and excitement. Boasting 8 spacious bedrooms and 7 full bathrooms, this expansive fully furnished residence provides ample space for family, guests, or business use. The state-of-the-art kitchen features top-tier appliances, while the generously sized living areas and cozy bedrooms ensure guests experience ultimate comfort. On the first floor, two beautifully designed rooms serve as either guest accommodations or private offices. The second floor features a large loft area that leads to five additional rooms, in addition to its luxurious primary bedroom suite that offers a serene retreat. Every corner of this home has been thoughtfully designed for both style and comfort. Recently updated, the home showcases a fresh, clean look with a new coat of paint that brightens the interior. Plush new carpeting throughout the bedrooms adds warmth and coziness, while ceiling fans improve airflow and enhance the modern aesthetic. The oversized, fully fenced lot boasts a private pool and ample yard space, ideal for a wide range of outdoor activities or enjoyable family game time. The garage has been upgraded with durable epoxy flooring and an AC unit, making it perfect for storage or as a versatile workspace. The new HVAC system ensures efficient climate control for year-round comfort. Beyond its luxurious features, this property also represents an exceptional investment opportunity. Located within an approved short-term rental community, this fully furnished home is perfectly positioned to succeed in the short-term rental market. Whether you're looking to generate income or provide guests with an unforgettable stay, this home is an ideal choice. Guests will love the convenient access to local cafes, restaurants, shopping, and entertainment, including parks and theaters. Encore at Reunion offers premier facilities and top-notch security, providing peace of mind for both residents and renters alike. With outstanding potential for strong returns on investment, this property is ready to start earning immediately. Don’t miss out on this incredible opportunity!

Listing is courtesy of: LA ROSA REALTY KISSIMMEE (407-930-3530)

Listing Agent: Christina Laidley (954-579-3742)

Remarks: Just minutes from Walt Disney World, this beautifully maintained 4-bedroom, 3-bathroom vacation home is located in the highly sought-after Emerald Island Resort and enjoys a private setting backing to a peaceful wooded conservation area in the heart of the community. Fully furnished and truly turnkey, the home features an open-concept layout designed for comfort, entertaining, and strong rental appeal. The garage has been professionally converted into a fully air-conditioned games room—an amenity guests consistently love and one that enhances occupancy and revenue performance. This property is an established and successful vacation rental with a strong booking history, and future reservations can transfer to the new owner if desired—offering immediate income from day one. Major capital improvements provide added peace of mind, including a new roof (2023), new pool heater, and new A/C system. Step outside to your private pool and covered lanai overlooking tranquil wooded surroundings with no rear neighbors—an ideal setting for guests to unwind after a day at the parks. Whether you are seeking a high-performing investment property or a personal Florida retreat with income potential, this home offers the flexibility to do both. Emerald Island Resort offers resort-style amenities including a gated entrance, clubhouse, community pool, fitness center, tiki bar, tennis and volleyball courts, and playground. With its unbeatable proximity to Disney, central resort location, strong rental performance, and recent upgrades, this property delivers the ultimate Central Florida vacation lifestyle and investment opportunity.

Listing is courtesy of: RE/MAX HERITAGE (863-424-2309)

Listing Agent: Steven Silcock (407-574-0218)

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)

Remarks: Beautiful fully furnished 3 beds - 2 bath home featuring a spacious open layout with NO CARPET throughout for a clean and modern feel. This well-maintained property offers comfortable living spaces, a fully equipped kitchen, stylish furnishings, and plenty of natural light. The primary suite includes a private bathroom and ample closet space. Conveniently located near shopping, dining, entertainment, and major highways, this move-in-ready home is perfect for those seeking comfort, convenience, and a turnkey living experience.

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

Listing Agent: Marianna Estrella De Castro (407-622-2122)

Remarks: SELLER MOTIVATED! Seller may contribute toward 6 months of HOA fees or buyer rate buy-down. Welcome to this 3-bedroom, 2-bathroom condo townhouse. Boasting the largest floor plan available, this spacious two story unit offers over 1,800 square feet of open-concept living space designed for comfort and functionality. Enjoy a bright and airy layout with soaring ceilings, a large living and dining area, and a private screened balcony, perfect for morning coffee or relaxing. The kitchen features ample cabinet space and a breakfast bar. The generous primary suite includes a walk-in closet and en-suite bathroom with dual sink. Two additional bedrooms provide plenty of space for family or guests. Oakwater is a resort-style, short-term rental approved community just minutes from Walt Disney World, shopping, and restaurants. Amenities include a sparkling community pool, clubhouse, fitness center, splash pad, tennis courts, and a game room, making it ideal for vacation rentals, a second home, or full-time Florida living. Schedule your private showing today!

Listing is courtesy of: THE FIRM RE (407-227-3345)

Listing Agent: Maria Zapata Sevilla (954-675-2458)

Remarks: Presenting the builder’s showcase home, featuring the very best of the Four Seasons at Orlando 55+ community. This former model is perched along hole #17 (par 3) of the Mystic Dunes Golf Course and stands supreme for its long list of upgrades and has been barely lived in. This Dominica model features 3 bedrooms (or 2 bedrooms plus den), custom-built wine bar, spectacular chef’s kitchen with giant island, gas cooktop, GE Profile oven and Advantium oven/microwave, glass tile backsplash, and custom cabinetry. The owner’s suite offers a sanctuary of its own with bright windows, porch entry door, tray ceiling, double vanities, and walk in glass-framed shower with multiple-headed jets. Collapsing sliding glass doors open to reveal a brick paver patio with gazebo, gas fire pit, fully fenced yard, and an unobstructed view of the golf course. Plumbing is already in place to create a summer kitchen of your dreams. This home is one of the few available homes featuring longer lasting and highly upgraded luxury tile roofing vs shingles. Plus, a three-car tandem parking garage, with a just-completed and beautiful concrete flooring coating. Four Seasons is a 55+ resort-style community offering 24-hour guarded gated access, a 13,000 square foot clubhouse, two in-ground pools, hot tub, and fitness center, plus tennis, pickleball, and bocce ball courts. Enjoy the carefree lifestyle as all exterior landscaping is included in the HOA fees. Located just minutes from Walt Disney World® and all of Central Florida’s famed attractions. (Note: Exterior & community aerial photos show damage from the recent hard freeze in the area; green and lush landscaping will return very soon!)

Listing is courtesy of: STOCKWORTH REALTY GROUP (407-909-5900)

Listing Agent: Rob Rahter (407-497-4526)