Kissimmee Homes with Pool Community Features

Kissimmee Homes with Pool Community Features

Welcome to Kissimmee, Florida – a vibrant city where sunshine meets adventure! Nestled just minutes from the magical attractions of Orlando, Kissimmee offers a perfect blend of excitement and tranquility. With its charming downtown area, bustling with shops, restaurants, and cultural attractions, Kissimmee is a fantastic place to call home. Whether you’re drawn to its scenic parks, beautiful lakes, or the allure of nearby theme parks, Kissimmee has something for everyone.

One of the standout features of homes in this delightful city is the abundance of properties with refreshing pools. Imagine stepping out into your own backyard oasis, where you can soak up the Florida sun, host summer barbecues, or enjoy a peaceful evening swim under the stars. Many communities in Kissimmee are designed with resort-style amenities, offering not just individual pools but also access to community features such as clubhouses, fitness centers, and walking trails.

Living in a Kissimmee home with a pool means embracing the Florida lifestyle to the fullest. Spend your weekends lounging by the water, or take a short drive to explore the natural beauty of the nearby Everglades. With a variety of housing options available, from cozy single-family homes to luxurious villas, you’re sure to find the perfect property that meets your needs.

Come discover why Kissimmee is not just a place to live, but a place to thrive. Dive into your dream home today and make every day feel like a vacation!

Newest Kissimmee Homes with Pool Community Features

2287 Portrait Street, Kissimmee
$315,000
3 Beds ⋅ 3 Baths ⋅ S5159087 MLS ⋅ Na BLDG.
Why wait for new construction when you can move right into this turnkey masterpiece? Located in Westview—widely recognized as one of the most Well-established and rapidly appreciating communities in the Poinciana area—this stunning 3-bedroom, 2.5-bathroom townhome offers luxury, convenience, and absolute peace of mind. Impeccably maintained by its current owners, this home feels completely brand new, with the massive advantage that several structural components are still covered under the builder’s warranty. Walk through the front door and be greeted by a bright, open-concept layout featuring soaring ceilings and gorgeous luxury tile flooring. The kitchen looks straight out of a designer magazine, featuring pristine quartz countertops, premium stainless steel appliances, and high-end finishes that make the entire space feel organized, modern, and luxurious. Step outside to your private patio to enjoy your morning coffee in total tranquility. Upstairs is designed for ultimate comfort. It features a spacious primary suite, two additional bedrooms, two full baths, and a highly versatile loft space that perfectly serves as a home office or study area. Location is everything, and this property delivers unmatched connectivity. You are just minutes away from Poinciana Medical Center, excellent schools, shopping, and dining. Commuting is a breeze with seamless access to the Poinciana Parkway, I-4, and the world-class entertainment of ChampionsGate. Living in Westview means enjoying resort-style amenities right at your doorstep, including a sparkling community pool, cabanas, scenic walking trails, and a dog park. This home is priced to sell and will not last long in this high-demand neighborhood. Schedule your private showing today and make this dream home yours before someone else does!

2287 Portrait Street, Kissimmee
2209 Southbury Drive, Kissimmee
$400,690
4 Beds ⋅ 3 Baths ⋅ O6450051 MLS
Under Construction. Tohoqua is the kind of neighborhood you've been looking for, with an exciting amenity center and a location within proximity to major roadways, including US-192, the FL. Turnpike and within 30 minutes of Orlando International Airport, Orlando’s world class amusement parks, and Medical City. Enjoy the adjacent Twin Oaks Park Florida Trail, featuring trails along famous Lake Tohopekaliga and connectivity to regional trail networks. A planned Village Center at the entrance to Tohoqua will offer shops, restaurants, healthcare and medical offices, a farmers' market and much more. Community amenities include a clubhouse, resort-style pool, community parks, a dog park, fitness center, sports courts, a playground and more! State-of-the-art technology will ensure that your family and business are connected to the latest and best tech options. Introducing the Jasmine bungalow, a brand-new home that includes 4 spacious bedrooms, 3 full bathrooms, and a 2-car rear-load attached garage. The heart of the home is the open-concept kitchen, café, and gathering room, all bathed in natural light. This inviting space is perfect for both everyday living and entertaining. The kitchen boasts a large center island, a convenient storage pantry, and top-of-the-line Whirlpool stainless steel appliances—including a refrigerator. White cabinetry, decorative tile backsplash, and quartz countertops complete the sophisticated look. For added convenience, the first floor includes a bedroom and a full bathroom. Upstairs, you’ll find the private owner’s suite, two additional bedrooms, a third full bathroom, and the laundry room. The owner’s suite is a true retreat, featuring a walk-in closet and a luxurious en suite bathroom with a glass-enclosed shower, quartz-topped dual vanity, and linen closet. This new construction home perfectly blends luxury, convenience, and modern design, making it the ideal place to live and unwind.

2209 Southbury Drive, Kissimmee
2628 Clear Night Avenue, Kissimmee
$361,400
3 Beds ⋅ 3 Baths ⋅ O6449959 MLS
Under Construction. Tohoqua is the kind of neighborhood you've been looking for, with an exciting amenity center and a location within proximity to major roadways, including US-192, the FL. Turnpike and within 30 minutes of Orlando International Airport, Orlando’s world class amusement parks, and Medical City. Enjoy the adjacent Twin Oaks Park Florida Trail, featuring trails along famous Lake Tohopekaliga and connectivity to regional trail networks. A planned Village Center at the entrance to Tohoqua will offer shops, restaurants, healthcare and medical offices, a farmers' market and much more. Community amenities include a clubhouse, resort-style pool, community parks, a dog park, fitness center, sports courts, a playground and more! State-of-the-art technology will ensure that your family and business are connected to the latest and best tech options. Introducing the Camden bungalow, a brand-new home that includes 3 spacious bedrooms, 2 full bathrooms, a powder room, and a 2-car rear-load attached garage. The heart of the home is the open-concept kitchen, café, and gathering room, all bathed in natural light. This inviting space is perfect for both everyday living and entertaining. The kitchen boasts a large center island, a convenient storage pantry, and top-of-the-line Whirlpool stainless steel appliances—including a refrigerator. Sarsaparilla cabinetry and quartz countertops complete the sophisticated look. For added convenience, the first floor includes a powder room. Upstairs, you’ll find the private owner’s suite, two additional bedrooms, a second full bathroom, and the laundry room. The owner’s suite is a true retreat, featuring a walk-in closet and a luxurious en suite bathroom with a frameless glass-enclosed shower, quartz-topped dual vanity, and linen closet. Throughout the first floor living spaces, enjoy the beauty of Wood-Look Luxury Vinyl Plank flooring, while tile enhances the laundry room and bathrooms. Plush, stain-resistant Shaw carpet covers the stairs and bedrooms, adding comfort and style. This new construction home perfectly blends luxury, convenience, and modern design, making it the ideal place to live and unwind.

2628 Clear Night Avenue, Kissimmee
5475 Gingham Drive, Kissimmee
$459,240
4 Beds ⋅ 3 Baths ⋅ W7890331 MLS
Pre-Construction. To be built. A Community Designed for Every Stage of Life. Westview features an intimate collection of 119 single-family homesites, creating a welcoming neighborhood feel with modern, thoughtfully designed floorplans. Whether you’re starting a new chapter or expanding your lifestyle, these homes are built to adapt to your needs. Personalization is at the heart of the experience, you’ll have the freedom to select your ideal homesite, design features, and finishes, allowing you to truly create a home that reflects your style and vision. Amenities That Inspire an Active, Social Lifestyle. At the center of the community is a vibrant social hub designed to bring neighbors together. The Hub clubhouse anchors the experience, offering: A fully equipped fitness center with a free weight room, an exciting rock-climbing wall, a multipurpose gymnasium with basketball court, a movement studio and locker facilities, and a welcoming gathering space with kitchenette and café. Step outside and enjoy an impressive collection of amenities designed for both recreation and relaxation: Pickleball, tennis, basketball, and volleyball courts, a lap pool, a resort-style pool with play features, and a dedicated kids pool, Open fields for baseball and soccer, a tot lot for younger residents, and a separate dog parks for small and large pets. Every detail is designed to support an active, connected, and wellness-focused lifestyle for residents of all ages. Welcome to the Serena, where convenience meets comfort across two thoughtfully designed stories. This clever home puts the owner’s suite right where you want it – on the main level – while keeping three additional bedrooms tucked away upstairs. The heart of the home shines with 9’4 ceilings and an open layout that makes the kitchen, dining, and family areas feel like one gorgeous space. Speaking of the kitchen, it boasts a 10’6” island that’s ready for everything from breakfast rushes to holiday cookie baking. Upgrades like a wall oven and beverage center can turn this space into your culinary dream. Upstairs holds a special surprise – a bedroom that can become a second owner’s suite – hello, multi-generational living! The adaptable loft space is ready for whatever your family throws at it – from movie marathons to homework sessions. With walk-in closets in every bedroom and smart storage solutions throughout, the Serena keeps clutter at bay. Best of all, the wall of windows and sliding glass doors leading to your patio (or optional lanai) bring the outdoors in, making every day feel a bit more like vacation. All Ryan Homes now include WIFI-enabled garage opener and Ecobee thermostat. **Closing cost assistance is available with use of Builder’s affiliated lender**. DISCLAIMER: Prices, financing, promotion, and offers subject to change without notice. Offer valid on new sales only. See Community Sales and Marketing Representative for details. Promotions cannot be combined with any other offer. Actual home may differ from photos. Schools: Elem: Koa Elementary School; Middle: Discovery Intermediate School; HS: New Dimensions High School.

5475 Gingham Drive, Kissimmee
4790 Goodmans Bay Drive, Kissimmee
$349,990
3 Beds ⋅ 3 Baths ⋅ W7890330 MLS
Pre-Construction. To be built. A Community Designed for Every Stage of Life. Westview features an intimate collection of 119 single-family homesites, creating a welcoming neighborhood feel with modern, thoughtfully designed floorplans. Whether you’re starting a new chapter or expanding your lifestyle, these homes are built to adapt to your needs. Personalization is at the heart of the experience, you’ll have the freedom to select your ideal homesite, design features, and finishes, allowing you to truly create a home that reflects your style and vision. Amenities That Inspire an Active, Social Lifestyle. At the center of the community is a vibrant social hub designed to bring neighbors together. The Hub clubhouse anchors the experience, offering: A fully equipped fitness center with a free weight room, an exciting rock-climbing wall, a multipurpose gymnasium with basketball court, a movement studio and locker facilities, and a welcoming gathering space with kitchenette and café. Step outside and enjoy an impressive collection of amenities designed for both recreation and relaxation: Pickleball, tennis, basketball, and volleyball courts, a lap pool, a resort-style pool with play features, and a dedicated kids pool, Open fields for baseball and soccer, a tot lot for younger residents, and a separate dog parks for small and large pets. Every detail is designed to support an active, connected, and wellness-focused lifestyle for residents of all ages. Introducing the Bonita – the standout performer in the 30’ FL product collection. This intelligently designed 1,866 sq. ft. two-story home delivers exceptional value through thoughtful space utilization. The main level features an open-concept layout where strategically positioned windows create a light-filled environment that transitions seamlessly from kitchen to dining to great room. Upstairs, find a well-appointed owner’s suite with two walk-in closets and a private bath, complemented by two secondary bedrooms and a versatile loft space that can convert to a fourth bedroom as needed. Available with two distinguished elevation options and optional stone accents, the Bonita presents an impressive exterior presence. With its integrated indoor-outdoor living spaces and adaptable floor plan, this home provides the perfect foundation for growing families seeking quality construction and enduring value. All Ryan Homes now include WIFI-enabled garage opener and Ecobee thermostat. **Closing cost assistance is available with use of Builder’s affiliated lender**. DISCLAIMER: Prices, financing, promotion, and offers subject to change without notice. Offer valid on new sales only. See Community Sales and Marketing Representative for details. Promotions cannot be combined with any other offer. Actual home may differ from photos. Schools: Elem: Koa Elementary School; Middle: Discovery Intermediate School; HS: New Dimensions High School.

4790 Goodmans Bay Drive, Kissimmee
2121 Avian Loop, Kissimmee
$456,900
4 Beds ⋅ 3 Baths ⋅ O6445376 MLS
Welcome to this impeccable 4-bedroom, 2.5-bath home in the 24-hour guard-gated Tapestry community! Built in 2020, this 2,176 sq ft residence makes an immediate impression with designer pendant lighting throughout: a statement fixture over the dining table, elegant pendants in the living area, and dramatic bedroom pendants cascading down to the nightstands. The open floor plan flows into a kitchen with granite countertops, stainless steel appliances and a large island with bar seating. The primary suite features tray ceilings, a walk-in closet and a spa-style bath with separate tub and shower and a double-sink vanity. Luxury vinyl flooring in all bedrooms, ceramic tile in main living areas, plus a covered screened lanai and utility sink for added convenience. Ceiling fans and all light fixtures convey. Resort-style amenities include the community pool, fitness center, clubhouse and playground, minutes from shopping, dining and everyday conveniences, with easy access to major highways. Sellers are offering closing cost concessions with acceptable terms.

2121 Avian Loop, Kissimmee
5444 Gingham Drive, Kissimmee
$364,990
4 Beds ⋅ 2 Baths ⋅ W7890328 MLS
Pre-Construction. To be built. A Community Designed for Every Stage of Life. Westview features an intimate collection of 119 single-family homesites, creating a welcoming neighborhood feel with modern, thoughtfully designed floorplans. Whether you’re starting a new chapter or expanding your lifestyle, these homes are built to adapt to your needs. Personalization is at the heart of the experience, you’ll have the freedom to select your ideal homesite, design features, and finishes, allowing you to truly create a home that reflects your style and vision. Amenities That Inspire an Active, Social Lifestyle. At the center of the community is a vibrant social hub designed to bring neighbors together. The Hub clubhouse anchors the experience, offering: A fully equipped fitness center with a free weight room, an exciting rock-climbing wall, a multipurpose gymnasium with basketball court, a movement studio and locker facilities, and a welcoming gathering space with kitchenette and café. Step outside and enjoy an impressive collection of amenities designed for both recreation and relaxation: Pickleball, tennis, basketball, and volleyball courts, a lap pool, a resort-style pool with play features, and a dedicated kids pool, Open fields for baseball and soccer, a tot lot for younger residents, and a separate dog parks for small and large pets. Every detail is designed to support an active, connected, and wellness-focused lifestyle for residents of all ages. Perfectly proportioned for Florida living, The Brooks delivers the ideal blend of space and versatility. Enter through a welcoming front porch to discover airy 9’ ceilings that flow through the main living areas. This showstopping kitchen features an expansive 8’9” island that seamlessly connects to the dining and great room – all brightened by a dramatic wall of rear windows. The owner’s suite is a true retreat, featuring a spa-like bathroom with dual vanities and generous storage including a walk-in closet. Choose from four bedrooms or transform one into a private study. The spacious lanai extends your living space outdoors, capturing that sought-after Florida lifestyle. Available in two eye-catching elevations with optional stone accents and decorative siding. Thoughtfully designed with extra windows and smart storage throughout, The Brooks proves that the perfect home is all about balance. All Ryan Homes now include WIFI-enabled garage opener and Ecobee thermostat. **Closing cost assistance is available with use of Builder’s affiliated lender**. DISCLAIMER: Prices, financing, promotion, and offers subject to change without notice. Offer valid on new sales only. See Community Sales and Marketing Representative for details. Promotions cannot be combined with any other offer. Actual home may differ from photos. Schools: Elem: Koa Elementary School; Middle: Discovery Intermediate School; HS: New Dimensions High School.

5444 Gingham Drive, Kissimmee
4767 Tribute Trail, Kissimmee
$330,000
3 Beds ⋅ 3 Baths ⋅ O6449724 MLS ⋅ N/A BLDG.
Virtually Staged. Welcome to Reflections at Storey Lake! Discover comfortable, low-maintenance living in this spacious 3-bedroom, 2.5-bathroom townhome offering approximately 1,859 square feet in one of Kissimmee’s desirable gated communities. The thoughtfully designed two-story layout provides plenty of room for everyday living, entertaining, and relaxing, with a functional floor plan that combines comfort and convenience. Beyond the home, enjoy an impressive selection of resort-style amenities that make every day feel like a vacation! Storey Lake offers a clubhouse, resort-style swimming pools, lazy river, waterslides, splash pad, fitness center, playgrounds, dog park, sports courts, mini-golf, and on-site dining. Whether you’re spending the afternoon lounging by the pool, enjoying the water attractions, or taking advantage of the community’s recreational facilities, there’s something for everyone to enjoy. In addition, the HOA makes this home truly worry free as it includes a cable/internet/phone package, exterior maintenance, roof, lawn and landscaping! Ideally situated near major highways, shopping, restaurants and minutes to Walt Disney World, this location provides convenient access to everything the Orlando area has to offer. Whether you’re looking for a primary residence or a vacation home, this townhome delivers an exceptional combination of space, convenience, and resort-style amenities. Schedule your private showing today!

4767 Tribute Trail, Kissimmee
3000 Maingate Lane Unit 124, Kissimmee
$47,000
1 Beds ⋅ 1 Baths ⋅ O6449576 MLS
INVESTMENT OPPORTUNITY minutes from Disney! Fully furnished turn-key suite waiting for you! This luxury room is located in Galleria Palms Hotel in Kissimmee right off of US-192. Come enjoy the Florida lifestyle where you are conveniently located and have everything you need all in one space. The Galleria Palms has resort style amenities including a daily deluxe breakfast buffet, outdoor pool, complimentary high-speed Wi-Fi, theme park shuttle service and guest laundry services. Walk through the door of your first floor unit and embrace the natural light and modern updates. The room includes two queen beds, wet bar, mini fridge, coffee machine, microwave, mounted flat screen TV, a safe, ironing board and iron, updated flooring, trendy artwork and furnishings. The bathroom features a double sink vanity and bathtub. The unit must stay in hotel rental program. This professionally managed condo-hotel offers a rare income model where revenue is evenly distributed across all units, rather than being based solely on individual bookings. This creates a more consistent income stream for owners. It's a perfect combination of hassle free investment with full on-site management services so your investment is well cared for 24/7 plus you can come stay and enjoy it yourself or book it for your friends and family. Galleria Palms is located near major roads giving it easy access to shopping and all of Orlando's wonderful attractions!

3000 Maingate Lane Unit 124, Kissimmee
421 Novi Path, Kissimmee
$549,900
5 Beds ⋅ 5 Baths ⋅ O6447934 MLS
Virtually Staged. FULLY FURNISHED | PRIVATE POOL | SLEEPS 10 | GATED RESORT | NEAR DISNEY | NO CARPET | Welcome to an exceptional opportunity to own a fully furnished luxury vacation home in Encore Resort, one of the area’s premier gated resort communities. Beautifully designer-decorated and offered completely turnkey, this immaculate pool home is ideal as a vacation retreat, second home, primary residence, or income-producing investment. From the moment you arrive, this home delivers the perfect combination of comfort, style, and resort living. The spacious open-concept floor plan creates an inviting environment for entertaining and relaxing, while the thoughtfully furnished interiors provide a true move-in-ready experience. With accommodations for up to 10 guests, this property is perfectly positioned for family vacations, group getaways, and short- or long-term rental opportunities. Recent Renovations: Luxury Vinyl Floor, Interior Paint, Great Room Furniture. Enjoy your own private outdoor oasis featuring a sparkling private pool. The property’s location near the resort’s gated entrance offers added convenience while keeping you close to all the amenities Encore Resort has to offer. Encore Resort provides an outstanding vacation lifestyle with an impressive collection of amenities, including a water park with multiple slides, resort-style pool, splash zone, fitness center, sports courts, playgrounds, clubhouse, restaurant and bar, concierge services, and 24-hour gated security. The community is also golf-cart friendly, making it easy to enjoy the resort and its amenities. The property is currently serviced by on-site property management, offering the opportunity for continued professional management and, if desired, the potential transfer of future reservations and bookings to the new owner. Guests and owners have access to the resort’s full amenity package, making this an especially attractive turnkey vacation property. Inside, you'll find a comfortable and stylish living environment with modern finishes, designer furnishings, digital cable TV, high-speed internet, and generous gathering spaces. Whether hosting guests or enjoying a quiet evening at home, the layout provides plenty of room for everyone. For added convenience, HOA services include lawn care, irrigation, exterior maintenance, trash service, and private pool maintenance, allowing owners to enjoy a truly low-maintenance property. Located just minutes from Walt Disney World, Sunset Walk, restaurants, shopping, golf, and Orlando’s world-famous attractions, this home puts the best of Central Florida right at your doorstep. Fully furnished, beautifully appointed, resort-managed, and ready to enjoy—this is the turnkey Florida vacation home you've been waiting for.

421 Novi Path, Kissimmee
8985 Cuban Palm Rd. Road, Kissimmee
$445,000
5 Beds ⋅ 5 Baths ⋅ C7532007 MLS
Your Florida lifestyle begins here. This five-bedroom, five-bathroom pool home for sale in Paradise Palms Resort, Kissimmee, offers approximately 3,015 square feet of inviting living space in a gated community near Walt Disney World. From quiet mornings beside your private pool to afternoons exploring Central Florida’s attractions, this home gives you room to enjoy it all. Soaring ceilings and an open floor plan create a welcoming setting for everyday living and entertaining. Granite countertops and stainless steel appliances anchor the kitchen, while the connected dining and living areas keep conversations flowing. Two primary suites provide comfortable retreats, and five full bathrooms make hosting overnight guests more convenient. Upstairs, a versatile loft offers additional space for a media area, game room, or relaxing lounge. Outside, your private heated splash pool invites you to unwind after a busy day or enjoy a leisurely afternoon at home. The operational pool heater adds comfort for cooler Florida days, making this outdoor retreat even more inviting. Paradise Palms Resort extends the experience with a clubhouse, resort-style pool featuring waterfalls and slides, fitness center, movie theater, tennis courts, volleyball, and a playground. Nearby shopping, dining, entertainment, and Orlando-area attractions bring convenience and recreation within easy reach. Offered unfurnished, this Kissimmee home gives you the freedom to create a space that reflects your own style. Whether you’re searching for a primary residence or a Florida vacation home near Disney, discover the space, comfort, and resort amenities waiting for you at Paradise Palms. Schedule your private showing today.

8985 Cuban Palm Rd. Road, Kissimmee
Brookfield Drive, Kissimmee
$57,450
A4709381 MLS
A fantastic opportunity to build your dream home on this BEAUTIFUL oversized cul de sac lot in the sought after West side of Poinciana in Osceola County. There is a very established section of Poinciana with very few vacant lots. This is, by far, the largest lot in the neighborhood offering the opportunity to be close to everything you need while surrounding yourself with privacy. There are no rear neighbors either and ample green space at the rea of the lot giving the feel of an even much larger parcel. The Poinciana community has community pool, Club House, Recreation Center, football, soccer, tennis courts, racket ball courts, baseball, softball, fitness trails, parks, dog parks and lakes for fishing. Near shopping centers, restaurants, medical offices, and the new Hospital, Banks, bus lines, schools, Valencia College. Very close to Disney's parks and all the attractions. The KOA Elementary school is right down the street which is an added bonus.

Brookfield Drive, Kissimmee
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