Kissimmee Homes with Pool

Kissimmee Homes with Pool

Welcome to Kissimmee, Florida, a vibrant city nestled in the heart of Osceola County, where sunshine meets adventure! Known for its close proximity to world-renowned attractions like Walt Disney World and Universal Studios, Kissimmee offers a unique blend of excitement and tranquility, making it the perfect place to call home. With its picturesque landscapes, diverse community, and rich cultural heritage, Kissimmee is not just a destination; it's a lifestyle.

One of the standout features of homes in this charming city is the abundance of properties with private pools. Imagine stepping out of your back door into your own personal oasis, where you can soak up the sun, entertain friends, or simply unwind after a long day. Homes with pools in Kissimmee are designed for both relaxation and fun, providing the ideal setting for family gatherings or peaceful evenings under the stars.

The real estate market in Kissimmee offers a variety of options, from cozy single-family homes to luxurious estates, catering to a range of tastes and budgets. Whether you're seeking a vacation home, a permanent residence, or an investment property, you’ll find that Kissimmee's homes with pools are not just a luxury; they are a lifestyle choice that enhances your quality of life.

Explore the possibilities that await you in Kissimmee, where every day feels like a vacation, and your dream home with a pool is just around the corner. Embrace the warmth of Florida living and make your move to this enchanting city today!

Newest Kissimmee Homes with Pool

$259,000
2 Beds ⋅ 3 Baths ⋅ O6444024 MLS ⋅ 302 BLDG.
Welcome to 302 Cervantes Drive! This well-located 2-bedroom, 2.5-bath townhome offers approximately 1,120 square feet of comfortable living space in the Rio Hills Townhouses community. The functional two-story floor plan features the main living areas downstairs, a convenient half bath for guests, and both bedrooms upstairs for added privacy. The spacious kitchen offers plenty of storage, including a large pantry, and the home also features central A/C and an interior laundry with washer and dryer. Enjoy the convenience of community amenities, including a pool, while being ideally situated near shopping, dining, schools, major roadways, Orlando International Airport, and Central Florida attractions. A new roof was completed in 2026, adding even more value and peace of mind. Whether you’re looking for a primary residence or an investment opportunity, this Kissimmee townhome is ready for its next owner. Schedule your private showing today!

302 Cervantes Drive, Kissimmee
$290,000
3 Beds ⋅ 2 Baths ⋅ O6445302 MLS ⋅ N/A BLDG.
Virtually Staged. POND VIEWS, vaulted ceilings, and a FIRST-FLOOR PRIMARY SUITE—this townhome has the features buyers look for. Natural light fills the open living and dining area, which leads to a screened patio overlooking the water. The kitchen pairs granite countertops with two pantries and a handy pass-through for serving and entertaining. The primary suite offers a walk-in closet and private bath, while two bedrooms, a full bath, and laundry are upstairs. You’ll also find luxury vinyl flooring, granite in the baths, a screened front porch with a generous storage closet, and TWO ASSIGNED PARKING SPACES. A/C was replaced in 2022 and windows and doors in 2023. Close to Disney, Universal, SeaWorld, shopping, and dining, with convenient access to the Turnpike, SR 417, and Orlando International Airport.

72 Pine Island Circle, Kissimmee
$375,000
3 Beds ⋅ 2 Baths ⋅ O6445155 MLS
Welcome to your own slice of Florida paradise! This charming 3 bedroom, 2 bathroom pool home offers the perfect combination of comfort, convenience, and waterfront living. From the moment you arrive, you'll appreciate the inviting curb appeal, tropical landscaping, and bright interior. Inside, discover a spacious kitchen featuring granite countertops, stainless steel appliances, ample cabinetry, and tile flooring. The beautifully updated bathroom features dual vessel sinks, a contemporary vanity, and an impressive walk-in shower with glass enclosure and marble-look tile. The primary bedroom offers a relaxing retreat with warm wood-look flooring and a modern ceiling fan. Step outside to the true highlight of this property: your private screened-in pool overlooking peaceful water views! Complete with shade sails and plenty of room for lounging and entertaining, this backyard offers the perfect setting for morning coffee, weekend barbecues, or simply unwinding while enjoying the Florida sunshine. With no immediate rear neighbors across the water, the picturesque setting adds an extra touch of tranquility. Conveniently located just minutes from Florida's Turnpike, The Loop, shopping, restaurants, and everyday essentials, this home offers easy access to everything Central Florida has to offer. Whether you're purchasing your first home, downsizing, or looking for a Florida retreat, this property offers an opportunity to enjoy the poolside lifestyle you've been dreaming of. Your own private pool, beautiful water views, and a convenient Kissimmee location. Schedule your private showing today!

269 Coralwood Court, Kissimmee
$650,000
4 Beds ⋅ 3 Baths ⋅ O6442242 MLS
Welcome to 1559 Skyline Dr, Kissimmee, located in the desirable Harbour Oaks community! This spacious 4-bedroom, 3-bath pool home sits on approximately 0.34 acres and offers an impressive combination of indoor comfort, outdoor living, and valuable upgrades. Major improvements include a roof replaced in 2021, pool resurfaced in 2021, PAID-OFF solar panels, and a pool enclosure re-screened in 2025. The pool also features a hybrid heater with a dedicated solar panel, while a solar-powered attic fan provides an additional energy-conscious feature. Inside, you'll find an updated kitchen and bathrooms, generous living and dining areas, and a versatile floor plan ideal for everyday living and entertaining. Additional features include motorized window treatments and a central vacuum system. Step outside and enjoy Florida living with a screened pool and spa, spacious covered lanai, and fully fenced backyard surrounded by mature landscaping. The generous lot provides plenty of additional outdoor space and even includes a chicken coop. Location adds even more appeal. Harbour Oaks is conveniently situated near the growing NeoCity development, with easy access to shopping, dining, and major Central Florida roadways, and is approximately 30 minutes from Orlando International Airport (MCO). With approximately 0.34 acres, a pool and spa, paid-off solar panels, 2021 roof, updated kitchen and bathrooms, and numerous improvements, this home offers an exceptional combination of space, comfort, and functionality. Schedule your private showing today and discover everything 1559 Skyline Dr has to offer!

1559 Skyline Drive, Kissimmee
$305,000
3 Beds ⋅ 2 Baths ⋅ G5118255 MLS ⋅ 1178 BLDG.
Affordable, Updated & Move-In Ready! Welcome to this charming 3-bedroom, 2-bath townhome in the desirable gated Jade East community! This home offers an excellent opportunity for a first-time buyer, second home, or investor looking for an affordable property with strong potential. Enjoy an open and comfortable layout, all vinyl flooring, updated appliances, HVAC replaced in 2019, and roof replaced in 2018. The spacious primary suite offers added privacy, while the additional bedrooms provide flexibility for guests, family, or a home office. Conveniently located near shopping, supermarket right across the subdivision, school less than 5 minutes, dining, major highways, and Florida’s Turnpike. Low-maintenance living at an affordable price — a great opportunity you won’t want to miss!

1178 Jade East Lane, Kissimmee
$375,000
3 Beds ⋅ 2 Baths ⋅ S5157562 MLS
Welcome to this beautiful home located in the desirable Kissimmee area! This inviting property offers a comfortable and functional layout with spacious living areas perfect for everyday living and entertaining. Enjoy a bright, open atmosphere with plenty of natural light throughout. The home provides comfortable bedrooms, ample storage, and a well-designed floor plan. Conveniently located near shopping, dining, schools, major roadways, and Central Florida attractions. Enjoy easy access to Orlando, Lake Nona, and surrounding communities. Don’t miss the opportunity to make this wonderful property your new home—schedule your private showing today!

2421 Ruddenstone Way, Kissimmee
$449,000
4 Beds ⋅ 3 Baths ⋅ O6443939 MLS
**This house comes with a REDUCED RATE through the seller's preferred lender. This is a lender-paid rate buydown that reduces the buyer's interest rate and monthly payment.** Welcome to this BEAUTIFULLY MAINTAINED 2020-BUILT, 4-BEDROOM, 2.5-BATHROOM HOME in the desirable East Lake Preserve community of Kissimmee. Thoughtfully designed with a spacious TWO-STORY FLOOR PLAN, multiple living areas, and an abundance of natural light, this home offers the perfect combination of comfort, functionality, and Florida living. Step inside to a welcoming entryway highlighted by VOLUME CEILINGS and strategically placed upper-level windows that fill the foyer with natural light. CERAMIC TILE FLOORING extends throughout the first floor, creating a clean, cohesive feel and an easy-to-maintain living space. The well-appointed kitchen is the heart of the home, featuring GRANITE COUNTERTOPS, STAINLESS STEEL APPLIANCES, STYLISH BACKSPLASH, GENEROUS CABINETRY, A LARGE PANTRY, and an oversized island with ample seating. The kitchen flows seamlessly into the casual dining area and additional living space, creating an inviting setting for everyday living and entertaining. A separate FORMAL DINING ROOM, FIRST-FLOOR BEDROOM, AND HALF BATH add valuable versatility. Upstairs, a semi-wraparound staircase leads to a SPACIOUS LOFT, providing even more flexibility for a media room, game room, home gym, study area, or comfortable lounge. The PRIMARY SUITE offers a peaceful retreat with a LARGE WALK-IN CLOSET and private ensuite bathroom featuring DUAL VANITIES and an oversized WALK-IN SHOWER. Two additional bedrooms provide plenty of space for family and guests, while the second full bathroom features a tub/shower combination. A linen closet and UPSTAIRS LAUNDRY ROOM add everyday convenience. Step outside to enjoy the Florida lifestyle from the COVERED, SCREENED-IN PATIO, an ideal space for morning coffee, outdoor dining, relaxing, or entertaining guests. The GENEROUS BACKYARD offers plenty of room to create your own outdoor oasis, whether you envision adding a private pool, outdoor kitchen, playground, garden, or simply keeping the open green space for pets and recreation. The attached TWO-CAR GARAGE features durable EPOXY FLOORING, adding both style and functionality. Beyond the home itself, enjoy the lifestyle offered by East Lake Preserve, a welcoming residential community designed around everyday comfort and outdoor enjoyment. Residents have access to a COMMUNITY POOL, PLAYGROUND, SIDEWALKS, AND NEIGHBORHOOD GREEN SPACES. Nestled in a prime location, East Lake Preserve provides convenient access to SR-417 and major Central Florida roadways, Lake Nona, Medical City, Orlando International Airport, shopping, dining, entertainment, and other Central Florida attractions. Schedule your private showing!

2631 E Lake Pointe Drive, Kissimmee
$380,000
3 Beds ⋅ 3 Baths ⋅ S5158243 MLS
Welcome to this beautifully maintained 3-bedroom, 2.5-bath home ideally situated on a desirable corner lot. Offering an excellent combination of comfort, privacy, and outdoor living, this property is perfect for a family or investor. The home features stainless steel appliances, tile flooring throughout, and a convenient inside laundry room. Step outside to your private retreat featuring a screened-in-ground pool, fully fenced yard, and a massive outdoor space with pavers throughout. Great location and tremendous potential—this is an opportunity you won’t want to miss!

100 Windy Dune Court, Kissimmee
$395,000
3 Beds ⋅ 2 Baths ⋅ S5158179 MLS
This 3 bedroom, 2 bath pool home in the Lakeshore neighborhood, located approximately one block from Lake Tohopekaliga and within 0.3 miles of Broadway Ave. in Downtown Kissimmee. The home features a split-bedroom floor plan, new vinyl flooring in the main living areas, fresh neutral paint, and large windows providing abundant natural light. The kitchen includes custom cabinetry, stainless steel appliances, and a built-in desk area. The kitchen, dining, and living areas provide an open layout with views of the in-ground pool and backyard. The primary bedroom also overlooks the pool and the backyard. The property includes a detached garage and metal storage shed for additional storage. The backyard overlooks a pond leading toward Kissimmee Lakefront Park and with Florida-native landscaping. Kissimmee Lakefront Park offers playgrounds, a splash pad, fishing, boating, and walking paths. Downtown Kissimmee is nearby with restaurants, events, a farmers market, and SunRail access.

406 E Drury Avenue, Kissimmee
$540,000
4 Beds ⋅ 2 Baths ⋅ S5157135 MLS
LAKE VIEWS & OPEN-CONCEPT LIVING! Welcome to this beautiful 4-bedroom, 2-bathroom home in the desirable St. Cloud at the Seasons at Big Sky community in Kissimmee. This inviting home features a bright, open-concept layout with a spacious kitchen, an oversized island with plenty of seating, abundant cabinetry, modern pendant lighting, and a seamless connection to the dining and living areas. Large sliding glass doors bring in plenty of natural light and showcase the beautiful lake views, creating a relaxing setting for everyday living and entertaining. Enjoy the lifestyle Seasons at Big Sky has with resort-style amenities, including a community pool, playground, sports courts, walking trails, and beautifully maintained open spaces. Conveniently located near US-192, major highways, shopping, dining, and Central Florida's world-famous attractions. Come experience the comfort, views, and convenience this home offers!

2949 Gavin Sky Drive, Kissimmee
$649,990
5 Beds ⋅ 3 Baths ⋅ O6442906 MLS
Welcome to 2841 Autumn Breeze Way, located in the highly sought after neighborhood of North Pointe. This stunning 5BR/3BA single-story residence boasts exceptional curb appeal, framed by lush, well-groomed landscaping leading into the entry. NEW AC 2026 w/ 10-YEAR Warranty Transferable. Offering 2,940 sq ft of open-concept living, the home features an entertaining-style kitchen designed for gathering, a flexible 5th bedroom/office, and a spacious 3-car garage. Modern convenience is integrated throughout with smart home features, including smart lighting, smart smoke detectors, smart garage access, an electronic front door lock, and a Ring doorbell. Enjoy Florida weather in the expansive pool area—offering ample space for family and entertaining while you cool down overlooking the serene conservation backdrop with total privacy and no rear neighbors. This home has been well cared for by the current owners and is move-in ready. Conveniently located near SR-417 & Boggy Creek Road, you have quick access to Lake Nona, Medical City, Orlando’s International Airport & Downtown Orlando, with shopping, dining & everyday conveniences just minutes away. Also situated along East Lake Toho & adjacent to Austin Tindall Sports Complex, North Point offers easy access to recreation & outdoor activities. Boggy Creek Rd expansion is almost completed. This is an incredible opportunity where luxury living and serenity meet you right at the front door. Come tour this beautiful home for yourself—schedule your private showing today before it’s gone!

2841 Autumn Breeze Way, Kissimmee
$347,900
2 Beds ⋅ 2 Baths ⋅ S5157977 MLS
This beautifully maintained home offers a bright, open-concept layout with tile flooring throughout the main living areas and plenty of natural light. The kitchen features white cabinetry, beautiful countertops, a decorative backsplash, modern appliances, a pantry, and a large center island overlooking the dining and living areas. Step outside to a private fenced backyard with an extended paver patio and covered lanai, perfect for relaxing or entertaining. Additional highlights include a two-car garage, paver driveway, attractive landscaping, and a spacious laundry room with additional cabinetry and storage. Enjoy the exceptional Tohoqua lifestyle with a resort-style pool, clubhouse, sports courts, walking trails, green spaces, and scenic ponds. Conveniently located in Kissimmee with easy access to Florida’s Turnpike, shopping, dining, and the growing surrounding area, this home combines modern comfort with an amenity-rich Florida lifestyle.

2706 Summer Retreat Lane, Kissimmee
Start Your Search