Kissimmee Homes with Pool Amenities

Kissimmee Homes with Pool Amenities

Welcome to Kissimmee, Florida – a vibrant city that perfectly blends the magic of theme parks with the tranquility of serene lakes and lush landscapes. Nestled just minutes away from the world-renowned Walt Disney World Resort, Kissimmee offers an idyllic setting for both families and retirees alike. With its warm climate, friendly communities, and endless recreational opportunities, it’s no wonder that Kissimmee is a sought-after destination for homebuyers.

One of the most appealing features of homes in Kissimmee is the abundance of properties boasting pool amenities. Imagine stepping into your backyard oasis, where shimmering waters invite you to unwind after a long day. Whether you're hosting summer barbecues or enjoying peaceful evenings under the stars, a private pool can transform your home into a personal retreat. Many of these residences are designed with outdoor living in mind, featuring spacious patios, lush landscaping, and easy access to the pool area, making them perfect for entertaining friends and family.

Kissimmee is also home to a variety of housing options, from charming single-family homes to luxurious villas, many equipped with resort-style pools. This city caters to diverse lifestyles, ensuring that everyone can find their dream home with the perfect poolside escape.

With its rich culture, diverse dining options, and proximity to some of Florida's most beautiful natural attractions, Kissimmee is not just a place to live but a place to thrive. Explore the possibilities of owning a home with pool amenities in this enchanting city, and dive into the Florida lifestyle you've always dreamed of!

Newest Kissimmee Homes with Pool Amenities

7 Beds ⋅ 10 Baths ⋅ Reunion West Fairways 17 & 18 SubDv. ⋅ 34747 Zip Code

Exceptional luxury, privacy, and rental appeal await in Reunion Resort’s prestigious Bear’s Den Club. Set on a rare oversized homesite with no rear neighbors and a private park directly behind the property, this fully furnished seven-bedroom residence offers one of the most desirable settings in the community. Professionally designed for unforgettable guest experiences, the home features immersive custom-themed bedrooms, multiple king suites, two creative bunk rooms, a state-of-the-art home theater, a spacious loft with billiards, and a dedicated arcade. The open-concept living area flows seamlessly outdoors to a private pool and spa, covered dining area, and fully equipped summer kitchen—perfect for entertaining and enjoying the Florida sunshine. Located just minutes from Walt Disney World and Orlando’s premier attractions, Bear’s Den offers access to Reunion Resort’s world-class golf courses, dining, tennis, water park, fitness center, and concierge services. An active Reunion Club membership is available, providing immediate access to the resort’s extensive amenities. Whether you’re looking for a luxury vacation retreat or a standout investment property designed to accommodate large groups, this home delivers an exceptional combination of location, entertainment, privacy, and resort living. Be sure to view the video tour!

1063 Jack Nicklaus Court, Kissimmee

4 Beds ⋅ 3 Baths ⋅ Preserve At Tapestry Ph 3 & 4 SubDv. ⋅ 34741 Zip Code

Welcome to 2815 Monticello Way—where comfortable living, entertaining space, and a convenient Kissimmee location come together! This 4-bedroom, 2.5-bath two-story home in the Preserve at Tapestry offers 2,328 square feet of living space, a two-car garage, and a large backyard designed for enjoying the outdoors. (*Listing includes some labeled virtually staged photographs.) Inside, the main level is made for gathering. The great room creates an easy flow between the spacious kitchen, large center island, dining area, and living room—giving everyone room to spread out while staying connected. Laminate flooring runs throughout the lower level, creating a clean and practical foundation for everyday living. Upstairs, the private primary suite offers a comfortable retreat with its own ensuite bath, while three additional bedrooms and a guest bath provide flexibility for family, guests, an office, or hobbies. Step outside and the living space continues! The large backyard features a screened porch, patio area, and garden space, creating multiple spots to relax, entertain, enjoy your morning coffee, or simply unwind at the end of the day. The generous yard also provides plenty of room to enjoy the outdoors and make the space your own. Recent updates include: Dishwasher — approximately 6 months old Range — approximately 1.5 years old Washing machine — approximately 1.5 years old Dryer — approximately 3 years old Life in Preserve at Tapestry includes access to community amenities such as a resort-style pool, clubhouse, playground, and trails, all included with the monthly HOA. Scenic ponds, tree-lined streets, and established landscaping contribute to the neighborhood's inviting setting. And then there’s the location! The Loop, shopping and dining along US-192 are just minutes away, while nearby Osceola Parkway provides convenient access toward Walt Disney World, Lake Nona, the Florida Turnpike, and SR 417. Orlando International Airport and Kissimmee Gateway Airport, Disney Springs, the major theme park corridor, Lake Tohopekaliga, and historic Downtown Kissimmee are also within easy reach. Come see 2815 Monticello Way and discover a home that offers space to gather, room to relax, and a Central Florida location that keeps you close to it all!

2518 Monticello Way, Kissimmee

4 Beds ⋅ 3 Baths ⋅ Westview 50s Gc SubDv. ⋅ 34758 Zip Code

Under Construction. This new single-story McCartney Next Gen® home features a private suite with its own entrance, living area, kitchenette, bedroom, bathroom and laundry, perfect for multigenerational households. The main home is host to an inviting open-concept layout with easy access to a covered patio for seamless indoor-outdoor living. Two secondary bedrooms are located off the foyer, and a lavish owner’s suite is tucked into a private rear corner, complete with a full bathroom and walk-in closet. Westview is a master-planned community in Poinciana, FL. This amenity-rich, pet-friendly community has something for residents of all ages to enjoy, including a swimming pool, dog park, clubhouse and sports fields. Lake Marion Creek Wildlife Management Area is nearby with hiking trails, as well as Poinciana for shopping, dining and entertainment options. The community is in close proximity to Highway 17 for easy commuting to Greater Orlando.

5595 Dennery Bay Road, Kissimmee

3 Beds ⋅ 3 Baths ⋅ Regal Oaks At Old Town SubDv. ⋅ 34746 Zip Code

Escape to one of the most desirable resort community with this beautifully maintained 3-bedroom, 2.5-bath townhome, and a private screened lanai with jacuzzi, creating the perfect setting to relax after a day of enjoying Central Florida's world-famous attractions. Step inside to discover a bright, open-concept floor plan designed for comfort and entertaining. The spacious kitchen flows seamlessly into the living and dining areas, while large windows invite natural light. Upstairs, the primary suite serves as a private retreat with balcony, featuring an en-suite bath with a generous walk-in shower. Whether you're seeking a vacation home, short-term rental investment, or full-time residence, this property offers the flexibility for the want of today's buyers. Located within the gated Regal Oaks Resort, owners and guests enjoy exceptional amenities including a resort-style pool with exciting water slides, clubhouse, restaurant, fitness center, tennis courts, and more. Imagine starting your mornings with peaceful setting and ending your evenings soaking in your private jacuzzi under the screened lanai. All of this just minutes from Disney, premier shopping, dining, and entertainment. Highlights: Tile roof... Private screened lanai with jacuzzi spa... Corner unit... 3 Bedrooms 2.5 Bathrooms... Open concept living and entertaining spaces... Inside laundry... Gated and guarded resort community with top-tier amenities... Ideal as a vacation home, investment property, or primary residence... Minutes from Disney, dining, shopping, and attractions. Don't miss your opportunity to own the community's best-valued townhome.

2715 Coupe Street, Kissimmee

5 Beds ⋅ 3 Baths ⋅ Kindred SubDv. ⋅ 34744 Zip Code

Under Construction. Kindred presents the Hayden. This amazing all concrete block construction single-family home features 5 bedrooms and 3 bathrooms optimizing living space with an open concept layout. The kitchen overlooks the dining area and great room, while having a view to the covered lanai outside. Ample windows and a set of sliding glass doors allow lighting into the living area. The well-appointed kitchen features an island with bar seating, beautiful quartz countertops and stainless-steel appliances, making entertaining a breeze. The first floor also features a flex room that provides an area for work or play, a bedroom, and full bathroom. As we head up to the second floor, we are greeted with bedroom one that features an en suite bathroom as well as three additional bedrooms that surround a second living area, a full bathroom, and a laundry area. Like all homes in Kindred, the Hayden includes Smart home technology package which allows you to control your home with your smart device while near or away. *Photos are of similar model but not that of exact house. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built. Home and community information including pricing, included features, terms, availability and amenities are subject to change and prior sale at any time without notice or obligation. Please note that no representations or warranties are made regarding school districts or school assignments; you should conduct your own investigation regarding current and future schools and school boundaries.*

1872 Southbury Drive, Kissimmee

3 Beds ⋅ 3 Baths ⋅ Paradise Cay SubDv. ⋅ 34746 Zip Code

Beautiful and spacious 3 bedroom, 3 bathroom townhouse in the GATED COMMUNITY of PARADISE CAY. This LARGER UNIT boasts 1,362 square feet under A/C and features an OPEN FLOOR PLAN with a recently UPGRADED kitchen including GRANITE COUNTERTOPS and FRESHLY PAINTED CABINETS. With 2 BEDROOMS and 2 FULL bathrooms upstairs, and a MASTER BEDROOM WITH FULL BATH ON THE FIRST FLOOR, this home is perfect for families. ALL APPLIANCES ARE NEW OR HAVE BEEN PURCHASED SINCE MARCH 2023 including the dryer, washer, refrigerator, garbage disposal, water heater, and AC/heating unit except for the stove and dishwasher, which were already new when the current owners purchased the home. All bedroom windows have blinds and curtains, while the living room window and patio have blinds. Located within WALKING DISTANCE to US 192, residents will enjoy easy access to restaurants, grocery stores, and other convenient stores. Paradise Cay is a Mediterranean-style community just 4 miles from the Disney main gate, offering a pool, cabana, and playground area for residents to enjoy making this home a great investment opportunity or a comfortable primary residence.

5315 Paradise Cay Circle, Kissimmee

4 Beds ⋅ 2 Baths ⋅ Kindred Ph 2a SubDv. ⋅ 34744 Zip Code

Kindred presents the Cali. This all concrete block constructed, one-story layout optimizes living space with an open concept kitchen overlooking the living area, dining room, and outdoor lanai. Entertaining is a breeze, as this popular single-family home features a spacious kitchen island, dining area and a spacious pantry for extra storage. This community has stainless steel appliances, making cooking a piece of cake. Bedroom one, located in the back of the home for privacy, has an en suite bathroom with a double vanity, spacious shower/tub space as well as a spacious walk-in closet. Towards the front of the home two additional bedrooms share a second full bathroom. Across the hall you will find a fourth bedroom. This home features a space to fit all your needs. Like all homes in Kindred, the Cali includes Smart home technology package which allows you to control your home with your smart device while near or away. *Photos are of similar model but not that of exact house. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built. Home and community information including pricing, included features, terms, availability and amenities are subject to change and prior sale at any time without notice or obligation. Please note that no representations or warranties are made regarding school districts or school assignments; you should conduct your own investigation regarding current and future schools and school boundaries.*

1511 Beechmont Drive, Kissimmee

3 Beds ⋅ 2 Baths ⋅ Kindred Ph 3b 3c & 3d SubDv. ⋅ 34744 Zip Code

Kindred presents the Allex. This all concrete block constructed, one-story layout optimizes living space with an open concept. As you go down the hallway and enter a spacious kitchen featuring stainless steel appliances with ample counter space and a walk-in pantry for extra storage. The living room is complete with a view to the covered lanai outside. Bedroom one, located at the back of the home for privacy, has an en suite bathroom that features a double vanity sink with a walk-in closet. Two additional guest bedrooms and one bath are tucked away down the hall from the dining room. The laundry room is located at the front of home near the two-car garage. Like all homes in Kindred, the Allex includes Smart home technology package which allows you to control your home with your smart device while near or away. *Photos are of similar model but not that of exact house. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built. Home and community information including pricing, included features, terms, availability and amenities are subject to change and prior sale at any time without notice or obligation. Please note that no representations or warranties are made regarding school districts or school assignments; you should conduct your own investigation regarding current and future schools and school boundaries.*

1921 Howard Mesa Drive, Kissimmee

4 Beds ⋅ 5 Baths ⋅ Magic Village Resort 2 SubDv. ⋅ 34747 Zip Code

4-Suite Villa at Magic Village Views The Ultimate Disney-Adjacent Investment & Vacation Oasis Step into elevated resort living with this fully furnished villa located inside the gated community of Magic Village Views. Situated less than 2 miles from Disney’s Animal Kingdom and close to Orlando’s top dining and entertainment districts, this residence offers an exceptional blend of modern sophistication, effortless comfort, and turnkey rental potential. The Home Designed with a clean, contemporary aesthetic, this spacious 4-bedroom, 4.5-bathroom "Columbia" floor plan is built for high-end relaxation and entertaining. Bright interior spaces and premium finishes set the tone throughout. 4 Private En-Suites: Each bedroom serves as its own quiet retreat, featuring a private, spa-inspired bathroom for ultimate guest convenience. Open-Concept Living: Soaring floor-to-ceiling windows flood the main living area with natural light, seamlessly connecting the indoor lounge to the outdoor patio. Gourmet Kitchen: Fully equipped with stainless steel appliances, sleek cabinetry, quartz counter space, and a breakfast bar for casual dining. Covered Patio: A private outdoor patio space perfect for morning coffee, lounging in the Florida sun, or unwinding after a day at the parks. Resort Amenities Owners and guests enjoy access to "The Magic Way" service—a full-service resort ecosystem with top-tier amenities: On-Site Dining: Enjoy elevated fusion cuisine right in the community at Japa Sushi. Resort-Style Pool: Large heated swimming pool, hot tub, and expansive sun deck open year-round. Active Recreation: Fully equipped fitness center, tennis court, and beach volleyball court. Concierge & Guest Services: Front desk service, park ticket assistance, and an activity room. Peace of Mind: 24-hour manned security gate and professional on-site property management. The Opportunity Ideal as a private retreat or a revenue-generating vacation property, this villa combines a prime Orlando location with high-demand resort features. Elevate your portfolio with a turnkey asset in one of the region's top destination communities. Schedule your private showing today and step into the Orlando resort lifestyle!

7521 Brooklyn Drive, Kissimmee

4 Beds ⋅ 5 Baths ⋅ Magic Village Resort 2 SubDv. ⋅ 34747 Zip Code

Spacious & Elegant 4-Suite Villa at Magic Village Views Luxury Resort Living Under 2 Miles from Disney Discover the perfect blend of high-end resort living and proven short-term rental performance with this fully furnished residence in the prestigious, gated Magic Village Views community. Located at 7544 Brooklyn Dr, this villa is positioned just minutes from Disney’s Animal Kingdom and Orlando’s premier entertainment corridors. The Residence Featuring the sought-after Columbia floor plan, this impeccably maintained property is designed for effortless hosting and maximum guest comfort: 4 Private En-Suites: Flexible multi-suite layout featuring 1 full suite on the main level and 3 full suites upstairs, plus an additional main-floor half bath for guests. Covered Summer Kitchen: Outdoor patio with a built-in BBQ station, ideal for outdoor dining. Modern Design & Upgrades: Open-concept living room with floor-to-ceiling windows, a fully equipped gourmet kitchen with stainless steel appliances, premium furnishings, and complete starter-to-finish amenities. Guest Capacity: Generously accommodates up to 10 guests. World-Class Resort Amenities On-Site Dining: Acclaimed Japa Sushi restaurant located right inside the community. Recreation & Wellness: Heated resort-style pool, hot tub, fitness center, tennis court, and beach volleyball court. Concierge & Guest Services: 24-hour manned security gate, front desk assistance, kids' playroom, and on-site property management. The Opportunity Whether configured as a personal vacation getaway or an income-generating vacation rental, this property delivers a turnkey solution in one of Central Florida's highest-demand tourism corridors. Contact today to schedule a private walkthrough or to request rental history details!

7544 Brooklyn Drive, Kissimmee

4 Beds ⋅ 3 Baths ⋅ Summer Flowers Twnhms SubDv. ⋅ 34746 Zip Code

Very close to Disney, on popular tourist corridor Highway 192 or Irlo Bronson Highway that lines up all restaurants, retail, gas stations, convenient stores, and Walmart Supercenter next to it, this beautiful unit (sold also as part of a 4-unit package if desired) can be used for short-term /long-term rental investment. This super-spacious corner-unit townhome boasts 1750 sft. in the most-sought-after Summer Flowers community! Built in 2022, this 4-bedroom, 2.5-bath property, with attached-garage and driveway, offers exceptional privacy with no rear neighbors (backing up up to Conservation) and tranquil, poolside views just off a quiet cul-de-sac. The first-floor features durable ceramic tile luxe vinyl plank flooring, an open-concept kitchen with stainless steel appliances, and a versatile flex room/bonus room ideal for a home office or den. Upstairs, are four spacious bedrooms, including a generous 13' x 14.5' primary suite with an en-suite bath and walk-in closet. Situated in a low-HOA gated community with a pool and sidewalks, this turn-key property is excellent for short-term rentals (1-7 day minimum lease) or long-term leases with a strong, low-vacancy rate or enjoy lifestyle-living homestead.

4444 Summer Flowers Place, Kissimmee

4 Beds ⋅ 3 Baths ⋅ Paradise Palms Resort Ph 2 SubDv. ⋅ 34747 Zip Code

Your ideal vacation retreat is right here in this fully furnished, tastefully designed 4-bedroom, 3-bath residence located inside the desired gated community of Paradise Palms. Paradise Palms provides a secure living environment with a 24-hour manned security gate for peace of mind. Perfectly positioned with a backyard view of the community pond and currently one of the closest units to the clubhouse with its impressive selection of resort-style amenities. The thoughtful floor plan includes an open-concept living area on the main level, along with a convenient first-floor bedroom suite. The remaining bedrooms and bathrooms are located upstairs for added privacy. The living room, dining room, and kitchen are freshly painted. The kitchen showcases granite countertops, a generous breakfast bar, and stainless steel appliances. The spacious living area is the perfect place to unwind after a day of fun, and the dining area offers access to the private pool deck. The upstairs master suite includes its own ensuite bathroom, and every bathroom features granite vanities. Outside, your covered private screened in lanai and heated pool are perfect for lounging and dining whether you prefer shade or sunshine. And when you want to enjoy the community, you’ll love the exceptional Clubhouse is just a short walk away, which features a resort-style pool and spa complete with sloped beach-entry, waterfall features, a splash area, a waterslide, cabanas, and an outdoor café. Additional amenities include tennis courts, basketball, beach volleyball, a fitness center, sauna, playground, and even a convenience store. Whether you’re searching for a personal getaway or a high-performing income-producing rental the location is unbeatable, just 2 miles from a grocery plaza and approximately 7 miles from the Disney parks. Discover why this home and the Paradise Palms community stand out as one of the best opportunities in the area! This property is active in a short-term rental program—contact the listing agent to confirm showing times.

3027 Beach Palm Avenue Unit 3027, Kissimmee

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