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

5 Beds ⋅ 5 Baths ⋅ O6434446 MLS

Whether you're looking for an income-producing vacation rental or a personal retreat, this 5-bedroom, 5-bath home in the highly desirable gated community of Windsor Hills is an excellent opportunity. The kitchen is positioned at the front of the home and overlooks the formal dining area, creating a welcoming space for family meals and entertaining. The living room is located at the rear of the home and opens to the screened-in pool deck, offering a relaxing space to enjoy the Florida sunshine. Two bedrooms are conveniently located on the first floor, along with two of the bathrooms, while the remaining bedrooms and bathrooms are upstairs, providing comfort and privacy for guests. The garage has been converted into a fun games room with pool and foosball tables, adding extra appeal for renters. Windsor Hills is one of the closest resorts to Disney and features outstanding amenities, including a resort-style pool with water slides, clubhouse, fitness center, and sports courts. Ideal for short-term rental investment, second home, or full-time residence.

7795 Basnett Circle, Kissimmee

2 Beds ⋅ 2 Baths ⋅ O6434424 MLS ⋅ 7 BLDG.

Welcome to Windsor Hills, one of Central Florida’s premier resort communities, located approximately two miles from Walt Disney World. This beautifully updated, fully furnished 2-bedroom, 2-bathroom condo offers turnkey convenience for use as a vacation retreat, short-term rental, or combination of both. Situated on the fourth and top floor of an elevator-served building, the condo is just one block from the clubhouse and water park—close enough for an easy walk while offering a peaceful setting. The bright, open-concept interior features a desirable split-bedroom floor plan, providing privacy for owners and guests. The remodeled kitchen includes quartz countertops, stainless steel appliances, generous workspace, and ample cabinetry. The private primary suite features an en-suite bathroom and walk-in closet. The Mickey Mouse-themed second bedroom offers flexible accommodations with a twin-over-queen bunk bed, twin trundle, foosball table, and custom Disney-inspired mural. The living room includes two leather sofas, one with a pullout bed. Both bathrooms have been fully remodeled with quartz countertops, newer soft-close vanities, custom wood backsplashes, and updated mirrors. Extensive improvements completed in 2022 and 2023 include new flooring and interior paint throughout, remodeled kitchen and bathrooms, stainless steel appliances, updated furniture, ceiling fans, lighting, and themed bedroom décor. Additional updates include a water heater replaced in 2022, and a Samsung washer and dryer installed in January 2026. A private balcony provides the perfect setting for morning coffee or relaxing after a day at the parks. Windsor Hills offers an exceptional collection of resort-style amenities, including a water park with three-story slides, an interactive splash zone, lagoon-style zero-entry pool, hot tub, tiki bar, fitness center, playground, 32-seat movie theater, putting green, arcade, convenience store, cybercafé, and tennis, basketball, and volleyball courts. The community also features 24-hour guard-gated security, convenient parking, oversized-vehicle access, and designated RV parking. Zoned for short-term rentals and offered fully furnished, this condo is ready for personal enjoyment or rental use after closing. Windsor Hills provides convenient access to Walt Disney World, Universal Orlando Resort, SeaWorld, area airports, US-192, I-4, and SR-429. Don’t miss this opportunity to own a top-floor condo in one of Central Florida’s most recognized vacation communities. Schedule your private showing today!

2817 Almaton Loop Unit 402, Kissimmee

10 Beds ⋅ 10 Baths ⋅ O6433659 MLS

Discover an exceptional SHORT-TERM RENTAL INVESTMENT OPPORTUNITY in the highly sought-after Encore Resort at Reunion. This beautifully appointed 10-bedroom, 10-bathroom TURNKEY vacation home is thoughtfully designed to accommodate large groups, multi-generational families, reunions, and Orlando vacationers, comfortably SLEEPING 20+ GUESTS. The spacious, open-concept floor plan is ideal for the vacation rental market, offering plenty of room for guests to gather while still enjoying their own private spaces. The gourmet kitchen is designed with large groups in mind and features dual refrigerators, two dishwashers, generous prep space, and sleek luxury vinyl flooring throughout the main living areas. Sliding glass doors create a seamless transition from the living and dining areas to the outdoor retreat, featuring a covered lanai, heated pool, and spa. With NO REAR NEIGHBORS and peaceful views of a greenbelt/conservation area, the backyard offers the privacy and setting vacation guests are looking for, whether enjoying a morning by the pool or relaxing after a day at Orlando's world-famous attractions. The home's impressive bedroom configuration adds to its rental appeal. Nine of the 10 bedrooms feature en-suite bathrooms, including two primary suites, one upstairs and one downstairs. A main-level accessible suite with a private accessible bathroom provides additional flexibility for guests. Upstairs, a spacious loft with a foosball table and an additional great room create even more entertainment and gathering space. Located within Encore Resort at Reunion, owners and guests can enjoy access to an impressive collection of resort-style amenities, including a spectacular clubhouse, award-winning restaurant, water park, full-service spa, playgrounds, state-of-the-art fitness center, and basketball, volleyball, and tennis courts. The community also offers gated entrances with 24-hour security and convenient resort services. A concierge desk is available at the clubhouse to assist guests with theme park tickets, dining, airline check-ins, resort-provided park shuttles, and more. Ideally positioned near Walt Disney World and Central Florida's premier attractions, as well as golf, shopping, dining, and entertainment, this property offers the combination vacation rental investors are looking for: size, guest-friendly amenities, privacy, resort appeal, and a prime Orlando-area location. Whether adding to an existing short-term rental portfolio or entering the Orlando vacation rental market, this Encore Resort property offers a compelling opportunity in one of Central Florida's most popular vacation destinations. Schedule your private tour today!

7519 Marker Avenue, Kissimmee

11 Beds ⋅ 10 Baths ⋅ O6433708 MLS

Welcome to an exceptional TURNKEY SHORT-TERM RENTAL INVESTMENT OPPORTUNITY in Encore Resort at Reunion, just minutes from Orlando’s world-famous theme parks. This fully furnished 11-bedroom, 10-bathroom vacation home is designed with large groups and vacationers in mind, comfortably SLEEPING 20–24 GUESTS and offering an impressive combination of space, entertainment, and resort-style amenities. The spacious open-concept floor plan features a gourmet kitchen equipped with two refrigerators and two dishwashers, along with generous dining and living areas ideal for accommodating large groups. Three bedrooms are conveniently located on the main level, including a bedroom with an accessible en-suite bathroom. Upstairs are eight additional bedrooms, including four custom-themed bunk rooms inspired by Marvel, Ghostbusters, Spiderman, and Pirates of the Caribbean, creating memorable spaces for younger guests. One of the home’s standout features is the converted Star Wars-themed game room, complete with a life-size R2-D2, air hockey, Aliens Extermination, Expert Shot Basketball, and two NASCAR virtual racing arcade games. Additional gathering spaces and laundry rooms on both levels add convenience for larger groups and extended stays. Sliding glass doors from the living area open to a covered patio, private heated pool and spa, and mature landscaping that provides additional privacy. It’s an inviting outdoor retreat where guests can relax and recharge after a day at the parks. Located within Encore Resort at Reunion, owners and guests can enjoy access to an impressive collection of resort amenities, including a clubhouse, restaurant, water park, full-service spa, playgrounds, fitness center, and basketball, volleyball, and tennis courts. The gated community also offers security, concierge services, and resort-provided transportation to area theme parks. With its 11-bedroom layout, themed bedrooms, incredible game room, private pool and spa, and prime location near Walt Disney World and Central Florida attractions, this property is ideally suited for the Orlando vacation rental market. Whether adding to an existing portfolio or looking for a turnkey short-term rental investment, this Encore Resort home offers the space, features, and guest experience to stand out. Schedule your private tour today!

7643 Wilmington Loop, Kissimmee

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

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