Kissimmee Homes with Pool

Kissimmee Homes with Pool

Welcome to Kissimmee, a vibrant city located in Osceola County, Florida. Known for its proximity to world-famous theme parks like Walt Disney World, Universal Studios, and SeaWorld, Kissimmee offers a perfect blend of entertainment and relaxation.

Imagine coming home to your very own piece of paradise in Kissimmee - a beautiful house with a pool where you can unwind and soak up the Florida sunshine. Homes with pools in Kissimmee are not just a luxury but a way of life, offering residents a refreshing retreat right in their backyard.

Whether you're looking for a cozy single-family home or a spacious estate, Kissimmee has a diverse range of properties with pools to suit every lifestyle. From entertaining guests to enjoying a peaceful morning swim, owning a home with a pool in Kissimmee adds an element of luxury to your everyday life.

As you explore real estate options in Kissimmee, consider the added value and enjoyment that a pool can bring to your home. It's not just a feature; it's a lifestyle upgrade that enhances your property and creates unforgettable memories with family and friends.

Discover the allure of Kissimmee living and find your dream home with a pool in this enchanting city in the heart of Florida. Experience the best of both worlds - the excitement of theme parks and the tranquility of your own private oasis. Welcome home to Kissimmee, where every day feels like a vacation.

Newest Kissimmee Homes with Pool

4 Beds ⋅ 3 Baths ⋅ S5155807 MLS

Welcome to **4385 Twisted Twig Bnd**, a spacious **4-bedroom, 2.5-bath home located in the desirable Storey Creek community of Kissimmee**. Built in 2024 and offering approximately **2,357 square feet of living space**, this home combines comfort, functionality, abundant natural light, and one of its most attractive features: **no rear neighbors and peaceful views of a natural area**, creating added privacy and a relaxing setting. The main living area features an appealing **open-concept layout** that seamlessly connects the family room, dining area, and modern kitchen, creating an ideal space for everyday living and entertaining. The kitchen includes **quartz countertops, stainless steel appliances, shaker-style cabinetry, an undermount sink, LED lighting, and a large center island**. Upstairs, the spacious **owner’s suite** features a **private en-suite bathroom and a large walk-in closet**. Three additional bedrooms, a **versatile loft**, and a conveniently located laundry room provide flexible space for family, guests, a home office, or additional living areas. The property also features a **2-car garage plus a driveway with space for 2 additional vehicles**, adding convenience and functionality for everyday living. Storey Creek enhances the lifestyle with excellent community amenities including a **resort-style swimming pool, clubhouse, fitness center, playground, dog park, and basketball court**. Its convenient location provides easy access to **shopping, dining, schools, medical services, major roadways, and Central Florida’s renowned attractions**. **Schedule your private showing today and experience the spacious layout, natural light, added privacy with no rear neighbors, and the Storey Creek lifestyle that make this home stand out.**

4385 Twisted Twig Bend, Kissimmee

4 Beds ⋅ 3 Baths ⋅ O6434314 MLS ⋅ 8217 BLDG.

Welcome to 8217 Surf St, a beautifully furnished 4-bedroom, 3-full-bath corner townhome located in the highly sought-after Margaritaville Resort Orlando. This spacious two-story home offers an open-concept living and dining area filled with natural light, stylish wood-look tile flooring, and a modern kitchen featuring quartz countertops, stainless steel appliances, ample cabinetry, and everything needed for a fully equipped vacation rental. The flexible floor plan includes a queen bedroom and full bathroom downstairs, while upstairs features three additional bedrooms: a spacious king bedroom, a queen bedroom, and a bunk room with two twin beds. Offered completely turnkey, the property includes all appliances, furniture, TVs, décor, artwork, housewares, kitchen necessities, dishware, linens, and furnishings, allowing the next owner to begin enjoying or renting the property right away. Whether you're looking for an income-producing short-term rental, a second home, or your own Florida vacation retreat, this property offers incredible flexibility. Margaritaville Resort Orlando offers a true resort lifestyle with multiple pools, fitness amenities, Island H2O Water Park, and convenient access to the restaurants, shopping, entertainment, and live music at Sunset Walk. Best of all, you're just minutes from Walt Disney World and Orlando's world-famous attractions. With its desirable corner location, spacious 4-bedroom layout, and complete turnkey setup, 8217 Surf St is an exceptional opportunity to own in one of Central Florida's most unique vacation resort communities—where every day can feel like a vacation.

8217 Surf Street, Kissimmee

3 Beds ⋅ 3 Baths ⋅ S5155515 MLS ⋅ Na BLDG.

Welcome to 2039 Cypress Bay Blvd, a well-maintained 3-bedroom, 2.5-bath townhome offering a comfortable living space in a convenient Kissimmee location. This home features an open and functional floor plan with tile and laminated flooring throughout the house. A screened rear porch—perfect for relaxing outdoors. Upstairs you'll find all three bedrooms, including the primary suite, along with two full bathrooms. Additional features include an attached 1-car garage and an oversized paver driveway providing plenty of additional parking. Conveniently located near shopping, dining, schools and major roadways, with easy access to the Florida Turnpike, Orlando International Airport, Lake Nona/Medical City and Central Florida's attractions. Whether you're looking for a primary residence or an investment property, this townhome offers an excellent combination of space, location and value.

2039 Cypress Bay Boulevard, Kissimmee

5 Beds ⋅ 6 Baths ⋅ O6434248 MLS

Welcome to your private resort retreat at Encore Club at Reunion! A stunning five-bedroom, five-and-a-half-bath residence built in 2020, offering 2,945 square feet of beautifully designed living space and an exceptional opportunity to own a turnkey vacation home in one of Central Florida’s most sought-after resort communities. From the moment you arrive, the elegant driveway and impressive curb appeal set the stage for the experience inside. The bright, open-concept floor plan was thoughtfully designed for comfort, style, and effortless entertaining. At the heart of the home, the gourmet kitchen seamlessly connects to the spacious living and dining areas and features beautiful California-style countertops, contemporary finishes, and an inviting layout ideal for entertaining family, friends, or vacation guests. Fully furnished and professionally decorated, this home is truly turnkey. Every detail has been carefully selected to create an upscale yet welcoming atmosphere while maximizing its appeal as a vacation rental. Each of the five generously sized bedrooms features a private en-suite bathroom, offering guests the comfort, privacy, and convenience expected from a luxury resort home. Step outside and discover your own private oasis. The sparkling private pool and spa create the perfect backdrop for relaxing under the Florida sun, enjoying an evening cocktail, or creating unforgettable vacation memories with family and friends. The spacious outdoor living area seamlessly extends the home's entertaining space and delivers the quintessential Florida resort lifestyle. And the resort experience doesn't stop at your doorstep. Located just steps from Encore's spectacular water park and clubhouse, residents and guests enjoy an impressive collection of resort-style amenities, including on-site restaurants, tennis courts, a state-of-the-art fitness center, basketball courts, playgrounds, and more—all within the security of a gated, professionally managed community. Whether you're looking for a luxury vacation home, a personal Florida getaway, or a high-performing short-term rental investment, this exceptional property offers the perfect combination of comfort, amenities, location, and investment potential. Ideally located just minutes from Walt Disney World, Universal Studios, championship golf, world-class shopping, and exceptional dining, this home places you at the center of Orlando's world-renowned vacation destination. Experience the best of resort living and investment opportunity at Encore Club at Reunion.

267 Southfield Street, Kissimmee

5 Beds ⋅ 5 Baths ⋅ O6434299 MLS ⋅ 8907 BLDG.

Turnkey 5-Bedroom Townhome – Short-Term Rental Approved! Welcome to this beautifully furnished 5-bedroom, 4.5-bathroom townhome, thoughtfully designed with fun Mickey Mouse and Harry Potter-themed bedroom, perfect for vacationers and investors alike. This move-in-ready property comfortably accommodates up to 12 guests and offers the ideal combination of space, comfort, and entertainment. The open-concept main living area features a modern kitchen with granite countertops, stainless steel appliances, ample cabinetry, and a spacious island perfect for gathering and entertaining. Step outside to your private screened-in pool and patio, an inviting space to relax and unwind after a day at the theme parks. Upstairs, a versatile loft provides additional room for entertainment, lounging, or family time. Guests can enjoy Windsor at Westside’s impressive resort-style amenities, including a clubhouse, resort pool, lazy river, water slide, fitness center, sports courts, game room, and playground—bringing the full vacation-resort experience right to the community.

8907 Sydney Avenue, Kissimmee

4 Beds ⋅ 3 Baths ⋅ O6434257 MLS

'PIRATES IN PARROTDISE' Cottage at Margaritaville Resort Orlando! Spacious Model 1384-C with 3 Bedrooms, 3 Bathrooms and an ADDITIONAL BONUS BEDROOM, BACK PATIO RETRACTABLE AWNING and a HOT TUB! Premium Location Near the Pedestrian Bridge! Spacious Living Room has a HUGE 75-INCH TV. IMMACULATE CONDITION ~ WELL MAINTAINED HOME. This home has NEVER been an STR and has been used as a SECOND HOME and LONG-TERM RENTAL most recently. First Floor Bedroom has En-Suite Bathroom and French Doors Leading to Spacious Backyard Patio with a Gorgeous GRASSY Backyard and TIKI HUTS. Second Floor has Primary En-Suite Bedroom with Front Balcony Access. Bonus Room has been Converted to a Bunk Room. The Kitchen features Upgraded Appliances, and Quartz Countertops. This Home also features Tile Flooring, Ceiling Fans Throughout, Washer and Dryer, Landscaping has Beautiful Foliage! All Furniture, Linens, Housewares and Decor INCLUDED IN LIST PRICE! Includes HIGH END ETHAN ALLEN FURNISHINGS, 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 and More! This is a Wonderful Community to Live in Full Time, Own a Second Home or Invest in a Vacation Rental Property! LOCATED MINUTES FROM DISNEY PARKS! Come Enjoy the Margaritaville Lifestyle in Paradise!

8036 Surf Street, Kissimmee

4 Beds ⋅ 4 Baths ⋅ O6434147 MLS

Beautiful MAIN VILLAGE home overlooking PRESERVE, POND and GOLF COURSE! This exquisite floor plan features 4 bedrooms and 3.5 baths plus office/ den (potential guest bedroom first floor)! Spacious foyer upon entry, and lots of windows, beautiful plantation shutters, and crown molding throughout. Features include hardwood flooring, charming wood burning fireplace, and detailed custom shelving. The Den/Office features a newly installed California Closets shelving unit. Light and bright Kitchen featuring recently updated quartz countertops and a beautifully coordinating backsplash. Enjoy the breakfast nook area with serene views of pond and golf course. Kitchen opens to family room, providing plenty of space to gather family and friends. Spacious bedrooms upstairs include 4 bedrooms and 3 bathrooms. The primary bedroom features a walk- in closet. New Water Heater 2025, AC 2020, Roof 2017 You'll love the long driveway and very Private lot! 2 CAR GARAGE w/storage and new epoxy flooring. This home is located on a beautiful tree lined street in fantastic conservation setting in Celebration's Main Village. The large backyard offers plenty of room for a pool! Walk to schools, downtown shops, restaurants, library and Golf Course. Hurry, this home won't last. You can't beat this location!

915 Jasmine Street, Kissimmee

3 Beds ⋅ 2 Baths ⋅ O6433300 MLS ⋅ 2952 BLDG.

Welcome to Lucaya Village! This charming 3-bedroom, 2-bathroom home offers approximately 1,300 sq. ft. of living space in a gated community ideally located in the heart of Kissimmee. The functional two-story floor plan features a bedroom and full bathroom on the first floor, providing added convenience and flexibility, while two additional bedrooms and a second bathroom are located upstairs. Enjoy the comfort of central air conditioning and a well-equipped kitchen featuring a refrigerator, range, microwave, and dishwasher. The community offers a swimming pool and additional amenities, while the HOA includes services such as cable TV, internet, exterior maintenance, pest control, and 24-hour guard service. Conveniently located near US-192 with easy access to shopping, dining, entertainment, and Central Florida's world-famous attractions. Whether you're looking for a primary residence or an investment property, this home offers an excellent opportunity in one of Kissimmee's most convenient locations. Schedule your private showing today!

2952 Lucayan Harbour Circle Unit 103, Kissimmee

2 Beds ⋅ 3 Baths ⋅ O6434097 MLS ⋅ 2702 BLDG.

Enjoy resort style Florida living in this fully furnished 2 bedroom, 2 bathroom lakefront townhome, just minutes from Disney World and Central Florida’s top attractions. The open floor plan offers a comfortable living room, dining area, and kitchen with no carpet throughout. The primary bedroom features a private balcony overlooking the beautiful pond and fountain. Step outside to the screened-in, enclosed patio with a hot tub perfect for relaxing and enjoying the Florida weather. The community offers fantastic resort style amenities including a restaurant, clubhouse, pool, gym and water slide, making this an ideal vacation home or investment property. With its lakefront setting, prime location, full furnishings and potential rental income, this townhome offers the perfect combination of comfort, convenience and Florida resort living. Call now for your private tour.

2702 Corvette Lane, Kissimmee

5 Beds ⋅ 6 Baths ⋅ S5155754 MLS

Welcome to 8896 Bengal Court, an exceptional opportunity to own a residence in one of Central Florida’s most sought-after destinations. Positioned in the desirable Kissimmee area, this property offers an appealing combination of lifestyle, location, and long-term investment potential. The property presents an attractive opportunity for discerning buyers seeking a Florida residence, second home, or investment property. Its convenient location provides easy access to Orlando’s world-class theme parks, entertainment, dining, shopping, and major transportation corridors, placing an impressive array of Central Florida attractions within reach. For investors, the property’s Kissimmee location offers the potential to benefit from the area’s strong tourism presence and continued demand for residential and vacation-oriented properties. For homeowners, it provides the opportunity to enjoy the sought-after Central Florida lifestyle while remaining close to everything the region has to offer. 8896 Bengal Court represents more than a home—it is an opportunity to establish a presence in one of Florida’s most dynamic real estate markets. Properties offering this combination of location, versatility, and investment appeal deserve a closer look. With its desirable location and versatile appeal, this property is ready for its next owner. Schedule your private showing today and discover all that 8896 Bengal Court has to offer!

8896 Bengal Court, Kissimmee

4 Beds ⋅ 5 Baths ⋅ S5155632 MLS

This exquisite Custom Venetian Estate Pool model is ideally located near the Palms Resort Amenities Center on an extra-large conservation lot, offering an exceptional combination of privacy, space, and luxury. From the moment you arrive, the home makes a stunning impression with a gated courtyard, custom stone planters, screened entryway, and elegant double leaded-glass doors. Inside, the welcoming great room features beautiful overhead beams, a custom bookcase designed for a 75-inch TV, which is included, and expansive views of the pool, lanai, and peaceful conservation area. The open-concept design creates an ideal setting for both entertaining and everyday living. The chef’s kitchen is designed to impress, featuring a large eat-at bar, Quartz countertops, solid-wood cabinetry, cooktop, double ovens, and an abundance of counter and storage space. The adjoining breakfast nook overlooks the pool and conservation area, providing a serene setting to enjoy your morning coffee. The spacious primary suite offers private conservation views and a luxurious spa-inspired bathroom with dual vanities, split double walk-in closets, a soaking tub, and a large walk-in shower. Bedroom 2 features a Murphy bed and private en-suite bath, while Bedroom 3 also includes an en-suite bath. The separate guest cottage in=law suite provides exceptional privacy for visitors and features its own full bathroom and walk-in shower. Additional interior highlights include a spacious den/study with double-door entry and a formal dining room accented by a dramatic double tray ceiling. Step outside to the oversized covered lanai and experience your own private resort-style retreat. The custom pool and spa are surrounded by an extended screened enclosure, lush landscaping, and tranquil conservation views, creating the perfect environment for relaxing or entertaining. The spacious 3-car garage provides ample room for vehicles, golf carts, and additional storage. Notable upgrades include a brand-new roof installed in July 2025, new Casita HVAC, 2024 water heater, 2026 Pool Deck painted, 2025 pool motor, water softener, hurricane shutters, whole-house generator, crown molding, Plantation shutters, lightning rods, and roll-up shade screens on the lanai. This exceptional Venetian Estate Pool home offers the rare combination of luxury, privacy, functionality, and resort-style outdoor living. Beautifully maintained and move-in ready, it is an extraordinary opportunity for those seeking an elevated lifestyle in Solivita. The HOA provides exceptional value by covering landscaping maintenance, irrigation, cable TV, and high-speed Internet, allowing you to enjoy a low-maintenance lifestyle in this desirable community. Solivita is a premier 55+ community, offering residents an exceptional lifestyle with state-of-the-art amenities. Enjoy a fully 2 equipped fitness centers, dance and aerobics studios, and an impressive array of recreational options including 14 heated swimming pools, two heated spas, tennis courts, pickleball courts, shuffleboard, bocce ball, billiards, and an art gallery. The community also features three on-site restaurants and two championship 18-hole golf courses. With a full calendar of activities and events, there’s always something new to explore and enjoy. This home is conveniently located near a hospital and medical office complex, and shopping center.

141 Lemon Grove Drive, Kissimmee

4 Beds ⋅ 3 Baths ⋅ TB8539232 MLS

Welcome to your private oasis in the highly desirable golf community of The Oaks! This beautifully upgraded 4-bedroom, 3-bath home features a spacious open floor plan plus a versatile bonus room that can easily serve as a 5th bedroom, home office, or guest suite. Designed for both everyday living and entertaining, the home features remodeled bathrooms, granite countertops, California Closets, crown molding, electric curtains, upgraded lighting, water softener and purification systems, and premium indoor/outdoor surround sound. Step outside to your own resort-style retreat featuring a screened and fenced heated saltwater pool and spa, cedarwood ceilings, shaded entertaining areas, mature landscaping, and plenty of backyard space. A circular driveway provides ample parking and adds to the home’s impressive curb appeal. The Oaks features an exceptional lifestyle with golf, access to Lake Toho, boating, fishing, tennis and basketball courts, playgrounds, and nature trails. Conveniently located near shopping, dining, schools, medical facilities, airports, theme parks, and all that Central Florida has to enjoy. A move-in-ready home where comfort, entertainment, and Florida living come together beautifully.

3034 Boating Boulevard, Kissimmee

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