Kissimmee Homes with Private Pool type

Kissimmee Homes with Private Pool type

Welcome to Kissimmee, Florida – a vibrant city that seamlessly blends the magic of theme parks with the charm of small-town living. Nestled just a stone's throw away from the world-renowned attractions of Walt Disney World, Universal Studios, and SeaWorld, Kissimmee is the perfect destination for those seeking both adventure and relaxation. With its lush landscapes, beautiful lakes, and year-round sunshine, this city offers a lifestyle that is as inviting as it is exciting.

One of the standout features of Kissimmee is the abundance of homes equipped with private pools. Imagine coming home after a day of exploring the wonders of Central Florida, only to unwind in your own oasis. These homes provide the ultimate retreat, allowing you to soak up the sun, host memorable gatherings, or simply enjoy a peaceful evening under the stars. Whether you're looking for a cozy bungalow or a spacious villa, Kissimmee offers a diverse range of properties to suit every taste and budget.

The community is also rich in amenities, from shopping and dining to parks and recreational facilities. Families will appreciate the top-rated schools and family-friendly neighborhoods, while retirees will find a welcoming atmosphere that encourages a relaxed lifestyle. With its strategic location, Kissimmee serves as a gateway to all that Florida has to offer, making it an ideal place to call home.

Discover the charm of Kissimmee and explore the possibilities of owning a home with a private pool – where every day feels like a vacation!

Newest Kissimmee Homes with Private Pool type

$419,000
3 Beds ⋅ 3 Baths ⋅ Windsor Hills Ph 2 SubDv. ⋅ 34747 Zip Code
ONE OF THE CLOSEST TOWNHOMES TO THE CLUBHOUSE! Located directly across the street, this exceptional 3-bedroom, 3-bathroom townhome offers one of the most convenient locations within the highly sought-after Windsor Hills Resort. Guests can enjoy a quick and easy walk to the clubhouse and resort amenities—an especially desirable feature for vacation rental guests. Welcome to a beautifully furnished vacation home just minutes from Walt Disney World! From the moment you step inside, you'll find a home designed to create a memorable Disney vacation experience. The spacious living room features a fun Disney-inspired theme, while the Toy Story-themed bedroom is sure to be a favorite among younger guests. The first-floor primary suite adds even more character with an exciting Incredibles theme. The open-concept kitchen, dining, and living area creates a comfortable gathering space for families to relax and spend time together after a day at the parks. A first-floor bedroom with a private bathroom provides added convenience and accessibility, while the upstairs ensuite bedroom offers additional privacy for guests. Durable flooring throughout the home eliminates carpet maintenance, making it especially well suited for a short-term rental. Step outside to the private screened-in lanai and enjoy the south-facing heated private pool, an ideal spot to relax and soak up the Florida sunshine year-round. As a guest or owner at Windsor Hills Resort, you'll have access to an impressive collection of resort-style amenities, including a lagoon-style pool, water park, water slides, movie theater, fitness center, arcade/game room, sports courts, playgrounds, onsite convenience store, bar and grill, and more. And the location is hard to beat. You're just minutes from Walt Disney World, with convenient access to Universal Orlando, shopping, restaurants, and countless Central Florida attractions. Whether you're looking for a vacation home, second home, or short-term rental investment, this property combines one of the best locations within Windsor Hills, themed interiors, a private south-facing pool, and strong guest appeal. Don't miss the opportunity to own one of the closest townhomes to the Windsor Hills clubhouse! Schedule your private showing today.

2592 Maneshaw Lane, Kissimmee
$415,000
4 Beds ⋅ 2 Baths ⋅ Eagle Pointe Ph 2 SubDv. ⋅ 34746 Zip Code
Turnkey pool home near Orlando's world-famous theme parks! This 4-bedroom, 2-bath home offers a spacious open floor plan, high ceilings, a private pool, and a move-in-ready setup. Currently used as an income-producing Airbnb and rental property, it offers excellent flexibility for investors, vacation-home buyers, or those looking for a primary residence. Conveniently located near Disney, Universal, shopping, dining, and major attractions. Enjoy the added benefit of low HOA fees and no rental restrictions. A great opportunity to own a versatile Florida property--schedule your showing today!

4632 Eagle Peak Drive, Kissimmee
$4,300,000
7 Beds ⋅ 9 Baths ⋅ Reunion West Village 3a SubDv. ⋅ 34747 Zip Code
Welcome to 1196 Castle Pines Court, an exceptional fully furnished 7-bedroom, 7-full-bath, 2-half-bath golf-front residence located within the exclusive gated Reunion Resort. Completely remodeled in 2025, this impressive home offers approximately 6,900 square feet of air-conditioned living space and 8,971 total square feet, combining sophisticated contemporary design with incredible spaces for entertaining. The newly redesigned kitchen showcases custom cabinetry, a walk-in pantry and a brand-new DACOR appliance package, opening seamlessly to the home’s expansive living areas. The main living room makes a dramatic statement with a large-format porcelain feature wall, custom millwork and electric fireplace. Throughout the home, the 2025 renovation continues with beautifully remodeled bathrooms featuring large-format porcelain tile, custom floating vanities with integrated sinks and sensor lighting, along with custom closets and elevated architectural finishes. A striking custom entryway features detailed millwork, large-format slabs and smoked-gray glass railing. Designed for entertaining on every level, the home features a dedicated Control4 theater with custom millwork and padded wall treatments, under-counter refrigerator and snack bar. A separate bonus room is ready for an arcade or gaming space, while the second-floor loft offers an additional sitting and TV area with billiard table. Outdoors, enjoy a private resort-style pool, expansive entertaining areas and a summer kitchen, all overlooking the 5th hole of Reunion’s Jack Nicklaus Signature Golf Course. The home is also equipped with a Culligan HANS whole-home reverse-osmosis system and is being offered fully furnished. Located within the gated Reunion Resort, residents and guests can enjoy an extensive collection of resort amenities, including championship golf, multiple dining options, tennis, miniature golf, water-park attractions and a lazy river. The home currently has an active Reunion membership. With its extensive 2025 renovation, designer finishes, entertainment spaces, golf-course setting and turnkey furnishings, 1196 Castle Pines Court offers a distinctive opportunity to experience the Reunion Resort lifestyle.

1196 Castle Pines Court, Kissimmee
$345,000
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
$439,999
4 Beds ⋅ 3 Baths ⋅ Blackstone Landing Ph 2 SubDv. ⋅ 34758 Zip Code
YOUR PRIVATE POOL RETREAT IN KISSIMMEE! Welcome to 2333 Walnut Canyon Drive, a spacious two-story home in the Blackstone Landing community featuring 4 bedrooms, 3 full bathrooms, 2,520 square feet of heated living space, and 3,164 square feet of total area. Designed for comfortable everyday living and memorable gatherings, this home features inviting living areas, a spacious kitchen with abundant cabinetry and counter space, and a versatile floor plan. The primary bedroom is conveniently located on the first floor, while three additional bedrooms upstairs provide flexibility for guests, a home office, or your evolving lifestyle needs. Step outside and discover your own private backyard retreat! Enjoy a swimming pool with an electric pool heater, an expansive paver patio, and a covered lanai ideal for relaxing, dining outdoors, or entertaining. The fenced backyard adds privacy and creates an inviting setting for enjoying Florida's sunshine. Adding to the home's appeal are fully paid-off solar panels, giving you the benefit of an owned solar energy system without a solar lease or panel loan payment. The roof and central A/C system have also been updated in recent years. Located in Blackstone Landing, this Kissimmee home provides convenient access to shopping, dining, and major Central Florida roadways. More space, your own heated pool, and the freedom to enjoy the Florida lifestyle right at home. Schedule your private showing today and discover what makes 2333 Walnut Canyon Drive special!

2333 Walnut Canyon Drive, Kissimmee
$339,000
4 Beds ⋅ 3 Baths ⋅ Paradise Palms Resort Ph 1 SubDv. ⋅ 34747 Zip Code
Welcome to the beautiful Paradise Palms Resort community, where comfort, convenience, and resort-style living come together in an exceptional Central Florida location. Located just minutes from Central Florida’s world-famous theme parks, including Walt Disney World, Universal Orlando, and SeaWorld, as well as shopping, dining, and entertainment. This beautifully maintained home offers an inviting atmosphere with pride of ownership throughout. The second floor and all bedrooms feature attractive vinyl flooring, providing a clean, modern look while offering easy maintenance and durability. The home is thoughtfully cared for and showcases a welcoming combination of comfort, functionality, and beauty. Residents and guests can enjoy an impressive selection of resort-style amenities, while the convenient Kissimmee location places you close to world-renowned theme parks, shopping, dining, and entertainment. Whether used as a vacation home, investment property, or personal retreat, this home offers an appealing opportunity to enjoy the Florida lifestyle in a desirable resort community.

8978 California Palm Road, Kissimmee
$699,999
5 Beds ⋅ 5 Baths ⋅ Sonoma Resort At Tapestry Ph 1 SubDv. ⋅ 34741 Zip Code
Welcome to this beautifully furnished 5-bedroom, 5-bathroom single-family home in the gated Sonoma Resort at Tapestry. Offering 3,067 square feet of living space, this turnkey resort-style property is ideal as a primary residence, vacation home, or investment property, with short-term rentals permitted subject to current HOA and governmental requirements. The spacious two-story floor plan features an open-concept living area, well-appointed kitchen with island, multiple en-suite bedrooms, and two bedrooms conveniently located on the main level. Entertainment is a highlight, with a private home theater featuring two rows of reclining seats and a themed game room currently set up in the garage with a pool table and air hockey. Enjoy Florida living year-round with a private screened-in heated pool and in-ground spa, covered outdoor living area, and pool views. The home is being offered fully furnished, including furniture, décor, appliances, theater seating, and game-room equipment shown in the MLS photos. Sonoma Resort at Tapestry offers resort-style amenities including a clubhouse, fitness center, community pool, sidewalks, trails, and gated security. Conveniently located near Walt Disney World, Central Florida attractions, shopping, dining, and major highways. Buyer and Buyer’s Agent to verify all room sizes, HOA fees, rental restrictions, pet restrictions, furnishings, community rules, and other property information.

3870 Oakville Avenue, Kissimmee
$465,000
4 Beds ⋅ 3 Baths ⋅ Storey Lake Ph 1b-2a SubDv. ⋅ 34746 Zip Code
Welcome to this beautifully 4-bedroom, 3-bathroom townhome located in the highly desirable Storey Lake Resort! This stunning property is being offered fully furnished and ready to enjoy. The spacious floor plan features one bedroom conveniently located on the first floor, while upstairs you’ll find a beautiful primary suite plus two bedrooms. Step outside to your own private screened-in pool, the perfect place to relax and enjoy the Florida lifestyle after a day at the parks. Located in one of the Orlando area’s most popular vacation communities, Storey Lake offers incredible resort-style amenities including a water park, lazy river, resort pools, fitness center, mini golf, sports courts, Tiki Bar, and much more. With excellent location just minutes from Walt Disney World and Orlando’s world-famous attractions, this home is an outstanding opportunity as a vacation rental, investment property, or personal getaway. Turnkey, furnished, and ready for its next owner!

3197 Pequod Place, Kissimmee
$5,350,000
8 Beds ⋅ 11 Baths ⋅ Reunion West Vlgs North SubDv. ⋅ 34747 Zip Code
Ideally located within the award-winning REUNION RESORT and sitting on a DOUBLE CORNER LOT, this beautifully presented FULLY FURNISHED 8-bedroom, 9 full / 2 half bathroom CUSTOM BUILT home showcases panoramic GOLF AND WATER VIEWS of the 16th hole of Traditions golf course. PROFESSIONALLY DESIGNED AND DECORATED with high end finishes and stunning built-in features abound, this luxurious TURNKEY ESTATE HOME has a meticulously thought thru’ floor plan and is perfect for entertaining on a large scale with its gourmet open plan kitchen, formal dining room (with seating for 12), home theater/media room, multiple lounge seating areas and fun arcade room. There is also a flex room with dedicated private balcony which can function as an office or a gym. The impressive foyer with DOUBLE HEIGHT entryway and sweeping double staircase adorned with an elaborate chandelier lighting fixture is simply breathtaking! There are TWO PRIMARY SUITES (one on each floor), 5 further spacious bedrooms as well as a bedroom consisting of two-double bunks, all are ensuite and have an abundance of closet and storage space. With a SUNNY SOUTH FACING ASPECT, the resort style outdoor area features a stunning INFINITY EDGE POOL WITH CASCADING FOUNTAIN, heated in-pool spa, WATERSLIDE and in-pool loungers all enhanced by an expansive PATIO/SUNDECK area with open as well as covered LANAI seating areas. Enjoy Florida outdoor living and lifestyle at its finest cooking on the grill in the OUTDOOR KITCHEN watching the early morning sunrise or evening setting sunset creating memories to last a lifetime. This residence can accommodate and provides ample parking space on its turnaround private driveway in addition to a functioning car garage which is a rare commodity within the community. With the added benefit of VERSATILITY OF USAGE, this stunning property is an ideal primary residence, second and/or vacation home and/or short term/long term rental and/or investment property! An ACTIVE TRANSFERRABLE MEMBERSHIP grants access to the many amenities of the Reunion Resort with its three world class golf courses (designed by Arnold Palmer, Tom Watson and Jack Nicklaus), a golf academy, Clubhouse at The Bear’s Den, six onsite restaurants, twelve community swimming pools, a multimillion-dollar water park with lazy river, six Har-True tennis courts, pickleball, bocce ball, volleyball, crazy golf, fitness center, a playground, and full-service salon and spa. Reunion has a variety of on-site dining options and is only a couple of miles away from Walt Disney World Resort, Seaworld and Universal Studios. 3D tour available. DON’T MISS OUT on this opportunity and schedule your private showing today!

971 Golden Bear Drive, Reunion
$429,900
4 Beds ⋅ 3 Baths ⋅ Brighton Lakes Ph 2 Prcl J SubDv. ⋅ 34746 Zip Code
Welcome to 2911 Sweetspire Circle, a beautifully refreshed 4-bedroom, 3-bath pool home offering the perfect combination of comfortable Florida living and a peaceful pond view. The home has been freshly painted inside and out, creating a clean, updated appearance from the moment you arrive. New carpeting adds to the move-in-ready feel, while the spacious four-bedroom, three-bath layout provides plenty of room for family, guests, a home office, or flexible living space. Step outside to your private swimming pool and enjoy one of the home's best features—the tranquil pond view. The outdoor area provides an inviting setting for morning coffee, relaxing by the pool, entertaining friends, or enjoying Florida evenings overlooking the water. Conveniently located in Kissimmee, this home combines a desirable Central Florida location with the features buyers continue to look for: four bedrooms, three full baths, a private pool, water views, fresh interior and exterior paint, and new carpet. Move-in ready, freshly updated, and ready to enjoy—schedule your showing today.

2911 Sweetspire Circle, Kissimmee
$489,000
4 Beds ⋅ 3 Baths ⋅ Oaks 2 The SubDv. ⋅ 34746 Zip Code
Welcome home to your private oasis! Step inside to impressive 12 ft. ceilings and large windows spreading natural light throughout the home. The spacious 4-bedroom 3 bath split plan also boasts a private office/den all on one level. The interior features classic finishes making it move-in ready while allowing you to update to your personal taste over time. A beautiful formal dining room is perfect for entertaining, and the rear of the home has a spacious screened lanai overlooking the pool and the greenspace beyond. Perfect for more casual get togethers. Truly a peaceful retreat!

1954 Willow Wood Drive, Kissimmee
$995,000
5 Beds ⋅ 6 Baths ⋅ Reunion West Village 3a SubDv. ⋅ 34747 Zip Code
SPECIAL LOT WITH A HIGHLY SOUGHT AFTER VIEW. RARE REUNION RESORT MEMBERSHIP AVAILABLE. RENTAL WINNER! HOME NEEDS NOTHING-TURN KEY! This featured property at 989 Desert Mountain Court in the highly desirable Fairway Ridge Community is located on a Cul-De-Sac and has spectacular views of the 1st hole of the World-Famous Nicklaus Golf Course Hole #1. The home has un-interrupted large golf course vistas that can be seen from the outdoor pool deck or the large second floor balcony. Once inside the home you will feel a sense of calm and welcome. The large open floor plan boasts a complete 1st floor bedroom, along with a private bath. The garage has been converted to maximize space and create more indoor entertainment zones. With a huge TV, arcade gaming, theater chairs, bar area and themed décor this garage has it all. Not to mention it even has a dedicated air conditioner to keep you and your guests cool! Deeper into the home you will find a ½ bath and laundry area. The large open living space is outlined by a generous sized kitchen, bar stool seating, a separate dining table and a picturesque view of the pool area and outdoor kitchen that is accessed by an oversized sliding glass door. The living room is comfortable, relaxing and is well appointed by updated furniture and electronics. You won't need a thing in this home! Once outside you are now living in the Florida Dream. A generous sized pool deck with great seating for guests and two umbrellas, is just the right place to snap a selfie! The second floor of the home is where you will find the loft area, additional gaming, and the remaining bedrooms. The home has an en-suite, a TOY-STORY themed bunk bedroom, a third well-appointed bedroom and a large master suite with accompanying master bath. The master suite has a large walk-in closet, along with separate vanities, and an oversized balcony that is great for a cup of coffee, or an evening glass of wine. Now my favorite part- the NEW LIST! ENTIRE INTERIOR NEW PAINT, ALL GROUT CLEANED AND SEALED, NEW CARPET, NEW PLANTATION SHUTTERS ON ALL WINDOWS, NEW FURNITURE IN COMMON AREAS, NEW OUTDOOR FURNITURE, NEW GAS COOK TOP, NEW BBQ GRILL, NEW DISHWASHER, NEW POOL HEATER 2025, NEW OUTDOOR LIGHTING. BIG RENTAL AND MEMORY MAKING POTENTIAL. Reunion Resort has everything you want in a community including 3 signature golf courses, world class dining, waterparks, lazy river, water slides, firework viewing areas, tree lined streets, dog park, playground, driving range, golf simulator, member events, in-resort shuttle service, and event space. Live the resort lifestyle like a VIP. NO OTHER RESORT IN THE AREA HAS THIS!!!! Minutes to Disney and close to Beaches, Universal, Legoland and Sea World. Schedule a tour today. 80 million visitors are estimated to visit Orlando in 2026. Current reservations for 2026 are available to convey to new owner when choosing to maintain relationship with current property manager. Schedule today!

989 Desert Mountain Court, Kissimmee
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