Kissimmee Homes with Pool Amenities

Kissimmee Homes with Pool Amenities

Welcome to Kissimmee, Florida—a vibrant city brimming with charm and excitement! Nestled just south of the world-renowned Orlando, Kissimmee offers a perfect blend of suburban tranquility and urban convenience. With its warm climate, picturesque landscapes, and proximity to iconic attractions like Walt Disney World and Universal Studios, Kissimmee is an ideal destination for families, retirees, and anyone looking to embrace the Sunshine State lifestyle.

One of the standout features of Kissimmee's real estate market is the abundance of homes with pool amenities. Imagine stepping into your backyard oasis, where you can relax and soak up the Florida sun or host unforgettable gatherings with friends and family. Whether you prefer a cozy, intimate pool or a sprawling resort-style retreat, Kissimmee has a diverse range of properties to suit every taste and budget.

The homes in this area often boast modern designs, spacious layouts, and lush landscaping, providing the perfect backdrop for your everyday life. With many properties located in family-friendly neighborhoods and gated communities, you’ll enjoy a sense of security and community while being just moments away from shopping, dining, and recreational activities.

Kissimmee’s rich cultural heritage, combined with its recreational offerings—like the nearby Lake Tohopekaliga for fishing and boating—ensures that there’s always something to do. So, whether you’re diving into your sparkling pool or exploring the local attractions, Kissimmee is a place where you can truly live your best life. Embrace the Florida lifestyle and discover your dream home with pool amenities in the heart of Kissimmee today!

Newest Kissimmee Homes with Pool Amenities

$210,000
3 Beds ⋅ 2 Baths ⋅ Chelsea Square 5b SubDv. ⋅ 34741 Zip Code
WELCOME HOME! LOW HOA! Seller offering $10,000 to Buyer for closing costs or renovations. This beautifully positioned 3-bedroom, 2-full-bath end-unit townhome in Chelsea Square is READY NOW and offers an excellent opportunity for a first-time home buyer, buyer looking for an affordable starter home, or investor seeking an income-producing rental property. Located toward the back of the community, this home offers a desirable open floor plan with the secondary bedrooms toward the front and the spacious primary suite privately situated in the rear. Tile flooring flows throughout the main living areas, laundry room, and bathrooms, while the primary bedroom and one secondary bedroom feature carpet. Bedroom 3 offers upgraded flooring. The kitchen is equipped with stainless steel appliances and granite countertops, making it both functional and inviting. Step outside to the screened-in back porch and private backyard, creating a comfortable space to enjoy your morning coffee, entertain guests, or unwind after a long day. Ample open parking is available for residents and guests. Chelsea Square also features a community pool for residents to enjoy. Conveniently located near shopping, restaurants, everyday conveniences, and major roadways, this home offers easy access to the surrounding area. Whether you're looking to stop renting and start building equity, purchase your first home, or add a rental property to your investment portfolio, this Chelsea Square townhome is an opportunity worth exploring.

3227 Chesswood Avenue, Kissimmee
$169,000
2 Beds ⋅ 2 Baths ⋅ Images Condo SubDv. ⋅ 34746 Zip Code
Make yourself at home in this inviting first-floor condo in the Images Condominium community, where a bright, open layout and a screened patio overlooking green space create a welcoming setting for everyday living. This move-in-ready, 2-bedroom, 2-bath residence features a spacious living and dining area with sliding glass doors that bring in natural light and extend the living space outdoors—perfect for enjoying your morning coffee or unwinding in the evening. The kitchen opens to the main living area through a breakfast bar, keeping you connected while preparing meals or entertaining. White cabinetry, a brand-new microwave, and an in-unit washer and dryer add style and convenience, while wood-look and tile flooring, a walk-in closet, and a split-bedroom layout complete the interior. Mature trees and landscaped grounds surround a community filled with ways to relax and stay active. Spend an afternoon by the pool, enjoy the spa, or take advantage of the fitness center, tennis and basketball courts, and sand volleyball court. A clubhouse, playground, picnic areas with barbecue grills, and controlled access add to the appeal. With shopping, dining, outlet malls, and Walt Disney World nearby, plus convenient access to I-4 and SR-417, this condo puts everyday essentials and favorite Central Florida destinations within easy reach. Come see it for yourself—schedule your private showing today!

5283 Images Circle Unit 104, Kissimmee
$299,900
3 Beds ⋅ 3 Baths ⋅ Tapestry Ph 4 SubDv. ⋅ 34741 Zip Code
Welcome to 2491 Fassona Drive, a beautifully updated townhome in the gated Tapestry community offering modern upgrades, a functional layout, and resort-style amenities. This 3-bedroom, 2.5-bath home features 1,528 square feet of living space and a 2-car garage. The first floor offers tile flooring throughout the living and dining areas, along with an updated kitchen featuring new 2025 cabinetry, granite countertops, and a walk-in pantry. A convenient half bath completes the first floor. Upstairs, new 2025 luxury vinyl plank flooring runs along the stairs and upstairs hallway, while all three bedrooms feature carpet. The spacious primary suite includes a walk-in closet, private bath with dual sinks, a separate shower and toilet closet, plus access to a large private balcony. Two additional bedrooms, a full bathroom with tub, and an upstairs laundry closet complete the second floor. Tapestry offers resort-style amenities including a community pool, splash pad, playground, fitness center, clubhouse, BBQ patio, screened lounge, multi-purpose room, and outdoor gathering spaces. Scenic water features throughout the community add to the neighborhood setting. Conveniently located near shopping, dining, major roadways, Orlando International Airport, and Central Florida’s world-famous theme parks, this home puts everyday conveniences and Central Florida’s major attractions within easy reach.

2491 Fassona Drive, Kissimmee
$250,000
3 Beds ⋅ 3 Baths ⋅ Emerald Island Resort Replat SubDv. ⋅ 34747 Zip Code
**Fully furnished and ready for its next owner!** This inviting 3-bedroom, 2.5-bathroom townhome is located in the highly desirable Emerald Island Resort, just minutes from Walt Disney World. The property is currently operating as a short-term rental, and future bookings may convey with the sale if the new owner chooses to continue with the current property management company. With a comfortable layout and everything needed for immediate enjoyment, this townhome is ideally suited as a vacation home, investment property, or personal getaway. Emerald Island is a gated, resort-style community offering two heated pools and spas, a clubhouse, fitness center, sauna, tennis and pickleball courts, mini golf, playgrounds, a nature trail, and more. A great opportunity to own a furnished townhome in one of Central Florida’s established vacation rental communities.

2782 Sun Key Place, Kissimmee
$260,000
2 Beds ⋅ 3 Baths ⋅ Encantada Ph 2 SubDv. ⋅ 34747 Zip Code
Great investment opportunity in the highly desirable Encantada Resort! This fully furnished, turnkey property offers a prime location in Kissimmee and is perfect for those looking to enjoy a vacation home, generate rental income, or use the property as a primary residence. This beautiful townhome features 2 bedrooms, 2.5 bathrooms, and 1,161 square feet of living space. The screened-in rear patio includes a private hot tub and peaceful views of the surrounding natural area. Enjoy a carpet-free home, with tile flooring throughout the first floor and laminate flooring on the stairs and second floor. The property is fully furnished and ready to enjoy from day one. Encantada Resort is a 24-hour gated community with excellent resort-style amenities, including heated pools, hot tubs, clubhouse, fitness center, playground, walking trails, and a poolside restaurant and bar. Ideally located just minutes from Walt Disney World, shopping, dining, golf, and major highways, providing easy access to everything Central Florida. A fantastic turnkey opportunity to enjoy, live in, or generate rental income from a property in one of Kissimmee’s most sought-after vacation destinations.

3063 White Orchid Road, Kissimmee
$133,000
1 Beds ⋅ 1 Baths ⋅ Villas Del Sol At Kiss Condo SubDv. ⋅ 34741 Zip Code
Beautiful freshly painted and well-maintained 1-bedroom, 1-bath condo, the unit is located in the gated, resort-style community of Villa del Sol, with controlled access through the Envera system. The unit is in the second floor with direct access to parking. The bedrooms has spacious walk-in closets. The community buildings have recently been updated with a modern exterior color palette and is very well maintained. Amenities include a clubhouse, fitness center, two swimming pools, on-site laundry facilities, car wash area, BBQ/picnic areas, playground, tennis courts and much more. Excellent opportunity for primary residence or investment. Located near to the Loop Mall with very close access to the Osceola Parkway, 192, 4-17, I-4, Restaurants, parks and attractions. Short rental allowed

2207 Antigua Place Unit 727, Kissimmee
$425,000
3 Beds ⋅ 2 Baths ⋅ Kindred Ph 3a SubDv. ⋅ 34744 Zip Code
Welcome to this stunning fully upgraded D.R. Horton Allex model, ideally positioned in a picturesque lakefront setting with an extended covered and screened lanai, within the highly desirable Kindred community. Built in 2023, this stylish three-bedroom, two-bathroom home offers modern design, an open split-bedroom floor plan and beautiful water views. The impressive kitchen is the heart of the home, featuring a gorgeous oversized quartz countertop and island with comfortable seating for four, a modern, large, farmhouse-style sink, touchless faucet, stainless steel appliances, abundant cabinetry and a spacious walk-in pantry. Gorgeous chandeliers and updated farmhouse-inspired lighting add warmth, elegance and character throughout the home. The private primary suite features an upgraded ensuite bathroom and a newly installed walk-in closet, giving the suite two walk-in closets and exceptional storage. Both bathrooms have been tastefully upgraded, while two additional bedrooms and the guest bathroom are conveniently positioned away form the master for ultimate privacy. A must see, must have turn key home, beautifully crafted exterior designed for peace, tranquility and luxurious living.

1827 Southfork Drive, Kissimmee
$234,000
2 Beds ⋅ 2 Baths ⋅ Solivita Ph 03b SubDv. ⋅ 34759 Zip Code
**See the FULL LENGTH VIDEO on Tour Link 1.** Welcome to Your Slice of Paradise! Imagine waking up every morning to tranquil pond views glistening in the Florida sunshine —your move-in-ready dream home in the award winning, 55+ gated community of Solivita awaits! This impeccably refreshed residence shines with luxurious carpeting throughout, offering that fresh, just-built feel without the wait. Step inside to soaring volume ceilings and a bright, open-concept floor plan that effortlessly blends living, dining, and entertaining spaces — perfect for hosting friends or enjoying quiet evenings at home. The heart-of-the-home kitchen delights with a breakfast bar, 2 water purifiers, cozy nook for casual meals, large pantry closet, and an abundance of cabinetry and counter space — everything you need to whip up culinary magic. Kitchen and laundry both have new LED light fixtures. Retreat to the spacious primary suite featuring serene water views, a huge walk-in closet, and a private en-suite bath with an oversized walk-in shower. An interior laundry room (conveniently tucked in the garage) adds everyday ease. Enjoy peaceful pond-front scenery from your back door — the ideal spot for morning coffee or sunset relaxation — all on a low-maintenance lot that gives you room to breathe without the work. No projects, no waiting — just unpack, settle in, and start living the vibrant Solivita lifestyle you’ve been dreaming of (golf carts welcome, resort-style pools, 200+ clubs, fitness centers, and more!). 1 and 1/2 car garage with epoxy garage floor (will fit one car and a golf cart). HWH 2023. Roof 2020 is to wind remittance standard with 35 year shingles. HVAC 2018 Furniture is available separately for a truly turnkey experience. Schedule your private tour today and make this Florida beauty yours before someone else does! ***Solivita is an active adult 55+ community located in Kissimmee, Florida. Approximately 50 minutes from Disney World & the Orlando International Airport. Solivita has a total of 5470 homes. About 10,000 – 11,000 residents live in Solivita during the winter while around 7,500 live in Solivita during the summer. Enjoy your active years in this piece of paradise. Solivita amenities include: a manicured SOFTBALL Diamond & Field - 36 holes of CHAMPIONSHIP GOLF that can be played by joining the Stonegate Golf Club or paying as you go – 2 STATE of the Art AMENITY centers with updated exercise equipment, yoga studio and meeting rooms – 3 restaurants -14 HEATED POOLS – 17 PICKLEBALL courts – 9 TENNIS courts -BOCCE BALL courts – Corn Hole – Tot Lot PLAYGROUND – COMMUNITY GARDEN – over 250 resident clubs. The HOA: - maintains the LANDSCAPING & IRRIGATION systems in the common areas as well as at individual homesites – maintains the roads throughout the community – provides SECURITY with gate guards and mobile patrols including the Polk County Sheriff – allows AUTOMATED GATE ACCESS for residents via license plate readers – provides residents with Fiber Optic Internet & TV service. ***Poinciana Lakes Plaza directly across from the Solivita Main Gate. It features Sprouts Grocery, TJ Maxx,Ulta, Outback, First Watch, 5 Guys, Jersey Mikes, Panda Express, Petco, Urgent Care, Dentist & More!

601 Grand Canal Dr, Kissimmee
$259,990
4 Beds ⋅ 3 Baths ⋅ Venetian Bay Village Condo Ph 3 SubDv. ⋅ 34741 Zip Code
Buy as your Vacation Home or live in this beautiful 2 story, 4 Bedroom, 3 Bathroom, located in the resort Style community of Venetian Bay Village in Kissimmee. This townhouse can serves as a primary residence, a long -term or short- term rental investment. It features a Master Suite located on the first floor and a second Master Suite upstairs. Beautiful bright open floor plan uniting the kitchen, dining area and living room. Not Carpet, Ceramic Title and Laminate floors. This unique resort style community features a huge Pool with Jacuzzi & 3 smaller pools. Playground and picnic areas, complete fitness center and basketball, tennis court and much more. The HOA fee includes Roofing, Exterior Painting, Landscaping, Lawn Services and outside Pets Control. Located close to the theme Parks, lots of Shopping, Restaurants and much more.

4010 Santa Maria Drive Unit 102, Kissimmee
$699,000
5 Beds ⋅ 6 Baths ⋅ Reunion West Ph 4 SubDv. ⋅ 34747 Zip Code
Welcome to your Florida retreat! Located inside of Reunion West luxury community, right across from the waterpark, Encore Club, and tennis courts. The Encore Resort is a gated community offering a waterpark, a resort-style pool, restaurants, a kid's playroom, tennis courts, basketball courts, sand volleyball courts, a soccer field, fitness center, mini market and 24 hr. concierge service! A shuttle bus service is also available with transportation to nearby Walt Disney Resort, Disney Springs, Universal Studios, and shopping malls! This spacious 5-bedroom, 5.5 bath home offers nearly 3,000 square feet of beautifully designed living space with plenty of room to gather, relax, and entertain. Step inside to a bright, open layout that flows effortlessly into the kitchen and main living areas, then head outdoors to enjoy your own private pool, spa and covered patio-perfect for soaking up the Florida sunshine or unwinding after a day of fun. Generously sized bedrooms and abundant bathroom space make the home especially well-suited for hosting family and guests. With attractive curb appeal, a paver driveway, attached garage, and a location in the heart of the Kissimmee area, this home offers the space, and lifestyle buyers are looking for. Whether you're searching for a primary residence, Florida getaway, or investment opportunity, this one deserves a closer look. HOA includes landscaping maintenance, irrigation, pest control, pool care (optional), trash collection, cable TV, and high-speed internet! Schedule your private showing today!

289 Auburn Avenue, Kissimmee
$575,000
4 Beds ⋅ 4 Baths ⋅ Bellalago Ph 4p SubDv. ⋅ 34746 Zip Code
Step into luxury with this fully remodeled Mediterranean-style home offering 4 bedrooms, 3.5 baths, and 3,591 square feet of beautifully designed living space. No expense was spared in the transformation, blending timeless architecture with a sleek, modern aesthetic. The home has been thoughtfully reimagined with an open floor plan that creates a seamless flow between living, dining, and entertaining spaces. At the heart of the home is a stunning kitchen, featuring a massive island with quartz countertops, custom cabinetry, and high-end finishes that balance sophistication with function. Every detail reflects quality and style, from the light-filled interiors to the carefully curated materials that give the home its clean, contemporary look. With generous living areas, spacious bedrooms, and spa-inspired bathrooms, this property offers the perfect combination of comfort and elegance. This one-of-a-kind residence is a true showpiece—ready to welcome its next owner to live and entertain in style.

3814 Golden Feather Way, Kissimmee
$499,000
3 Beds ⋅ 2 Baths ⋅ Solivita Ph 02d SubDv. ⋅ 34759 Zip Code
Virtually Staged. Stunning water views set the stage for this beautifully maintained Rhapsody model in Solivita, where spacious interiors, elegant finishes, and exceptional outdoor living come together. Conservation views across the front provide a peaceful welcome, while the expansive water backdrop creates a striking setting for everyday life. Double leaded-glass doors open to an airy, open interior accented by beautiful crown molding and luxury vinyl plank flooring throughout the living areas. With three bedrooms, separate living and dining rooms, and a Florida room, the home offers generous space to gather, entertain, and unwind—all with no carpet. The kitchen blends style and functionality with a center island, cooktop, double ovens, glass-front cabinetry, and a breakfast bar. The primary suite enjoys tranquil water views and features a large walk-in closet and an en-suite bath with an oversized walk-in shower, soaking tub, and dual vanities. Sliding glass doors extend the living room onto the covered, screened lanai, creating an inviting connection between indoor and outdoor living. The Florida room captures additional water views and features a custom built-in cabinet with mirrored shelving. The extended screened lanai is the home’s signature retreat. Overlooking the water, this expansive outdoor space features a gazebo extension and an established koi pond with a walk-over bridge—a distinctive setting for morning coffee, relaxed evenings, and memorable gatherings. Thoughtful conveniences include custom laundry room cabinetry, a utility sink, and a two-car garage with extra storage and pull-down access to a floored attic. Additional features include an in-wall pest control system, water softener, and central vacuum system. Updates include HVAC (2023), water heater (2020), and roof (2016). Solivita is an award winning 55+ community featuring over 4200 acres of wetlands, parks and lakes, 150,000 sq ft of state of the art amenities and work out facilities, 14 heated swimming pools, 2 heated spas, 2 dog parks, tennis courts, pickleball courts, shuffleboard, bocce ball, billiards room, art gallery, community garden, 3 restaurants and 2 championship 18-hole golf courses. The large ball room hosts almost nightly events and the more than 200 clubs will ensure that you can find something fun to do! Join the travel club, the pizza club, the Disney club or do nothing at all while you sit peacefully in one of the many quiet park settings. Voted one of the top 6 communities in America, Solivita is close to the theme parks and all the wonderful adventures that Central Florida has to offer. Solivita is a little piece of paradise. Call us today!

801 Glendora Road, Kissimmee
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