Osceola Homes with Pool

Osceola Homes with Pool

Welcome to Osceola County, located in the sunny state of Florida! Known for its vibrant communities, stunning natural landscapes, and endless recreational opportunities, Osceola County is a fantastic place to call home.

If you're in the market for a home with a pool, Osceola County has plenty to offer. Imagine spending your weekends lounging by the pool, hosting barbecues with friends and family, or simply enjoying a refreshing dip after a long day. Homes with pools in Osceola County provide the perfect setting for a relaxed and luxurious lifestyle.

Whether you're looking for a cozy bungalow, a spacious family home, or a luxurious estate, Osceola County has a diverse range of properties with pools to suit every taste and budget. From modern amenities to stunning outdoor spaces, these homes are designed for both relaxation and entertainment.

With year-round sunshine and warm weather, having a pool at home is not just a luxury but a necessity in Osceola County. It's the perfect place to create lasting memories, unwind in your own private oasis, and make the most of the Florida lifestyle.

Don't miss out on the opportunity to own a home with a pool in beautiful Osceola County. Contact us today to find your dream home and start living the good life in this charming Florida community.

Newest Osceola Homes with Pool

$695,000
5 Beds ⋅ 6 Baths ⋅ Reunion West Ph 1 East SubDv. ⋅ 34747 Zip Code
Welcome to 7564 Marker Avenue, an outstanding turnkey investment and lifestyle opportunity in the highly desirable gated resort community of Encore at Reunion, just minutes from Walt Disney World and Orlando’s world-class attractions. This fully furnished, professionally themed 5-bedroom, 5.5-bath luxury home offers over 3,300 square feet of thoughtfully designed living space, blending comfort, style, and strong short-term rental potential. The open-concept main level features a spacious family room, dining area, and modern kitchen, with the primary suite conveniently located on the first floor for added privacy and functionality. Upstairs, guests will find additional themed bedrooms and a versatile bonus/game room, creating an immersive vacation experience that consistently appeals to short-term rental guests. The home is designed for maximum occupancy appeal while still offering a warm and inviting feel for personal use. Step outside to your private resort-style pool and spa, complete with outdoor lounging space ideal for relaxing or entertaining after a day at the parks. All furnishings are included, making this a true turnkey purchase opportunity ready for immediate enjoyment or rental income. Located within Encore at Reunion, residents and guests enjoy world-class amenities including a water park, clubhouse, fitness center, tennis courts, and 24-hour gated security. With its prime location, strong vacation rental demand, and resort-style features, this property represents an exceptional opportunity for both personal enjoyment and income-producing investment.

7564 Marker Avenue, Kissimmee
$1,375,000
6 Beds ⋅ 5 Baths ⋅ Waterside Vista SubDv. ⋅ 34771 Zip Code
Virtually Staged. Mediterranean Elegance Meets Waterfront Luxury in the Exclusive Gated Community of Waterside Vista. Experience an extraordinary blend of luxury, privacy, and convenience in this stunning Mediterranean-inspired estate, nestled within this exclusive private boating community of only 24 custom residences. Enjoy the benefit of lower St. Cloud taxes while being adjacent to Lake Nona, just minutes from world-class dining, shopping, and only 20 minutes from Orlando International Airport. Situated on a .64-acre waterfront homesite, this 5,193-square-foot estate offers 6 bedrooms, 5 bathrooms, and two versatile flex rooms ideal for a home office, gym, playroom, or additional guest space. Enjoy breathtaking canal views with direct access to Fells Cove, East Lake Tohopekaliga, and the Chain of Lakes. The deep-water canal offers the opportunity to build your own private dock and enjoy the ultimate Florida boating lifestyle. From the moment you arrive, the home's striking Mediterranean architecture commands attention. A dramatic two-story turreted entrance, reminiscent of a castle, welcomes you into a spectacular 24-foot foyer highlighted by an elegant Juliet balcony. The home's impressive curb appeal is further enhanced by an extended driveway that accommodates up to 11 vehicles and is complemented by a rare five-car split garage, perfect for car enthusiasts, boat owners, or multigenerational living. The garage also features both a Tesla charger and an EVBox charging station. The open-concept floor plan is designed for entertaining and everyday living, featuring a chef's kitchen with an oversized granite island, upgraded countertops, stainless steel appliances, gas cooktop, and separate butler's pantry. An oversized laundry room offers abundant cabinetry, while thoughtful accessibility features including a residential elevator and front entry ramp provide comfort and convenience. The first-floor owner's suite is a private retreat featuring a custom walk-in closet with built-in organizers. A second first-floor bedroom and full bath are ideal for guests or multigenerational living. Upstairs offers a spacious bonus room with wet bar, a dedicated theater room, and four oversized bedrooms, including one with its own Juliet balcony. Step onto the second-floor balcony and take in beautiful canal views. Outdoor living shines with a heated saltwater pool, recently replaced pool motor, and a brand-new screened enclosure. More than 84 solar panels help minimize electric costs, while a whole-home water treatment system enhances everyday comfort and efficiency. This exceptional home combines luxury waterfront living, private boating access, energy-efficient upgrades, accessibility features, abundant parking, and an unbeatable location next to Lake Nona. Contact the listing agent today to schedule your private tour or RSVP for the upcoming Open House.

5229 Waterside Vista Lane, St Cloud
$389,900
3 Beds ⋅ 2 Baths ⋅ East Lake Preserve Ph 3 SubDv. ⋅ 34744 Zip Code
Welcome to this beautifully designed 3-bedroom, 2-bath home plus a versatile bonus room featuring a walk-in closet; ideal as a home office, playroom, guest room, or 4th bedroom. Enjoy indoor and outdoor living with a welcoming front porch and a covered screened lanai overlooking the fenced backyard. The open concept layout offers a spacious living area, ideal for everyday living and entertaining. The kitchen features granite countertops, a large island, espresso 42-inch cabinetry with crown molding, stainless steel appliances, undermount sink, and ample storage. The private owner's suite includes a walk-in closet and an en-suite bath with dual granite vanities and glass enclosed shower. Two additional bedrooms, a second full bathroom, and a generously sized utility room complete the home. Additional highlights include in-wall pest control, dual-pane windows, and barrier roof sheathing for energy efficiency. Community amenities include a pool, playground, dog park, and internet service included in the HOA dues. Ideally located with easy access to SR-417, this home is just 5 miles from Boxi Park and Lake Nona Medical City, 7 miles from Orlando International Airport, and short distance to shopping, dining, and top-rated schools. Experience the perfect combination of modern comfort, community amenities, and great location.

2732 E Lake Pointe Drive, Kissimmee
$325,000
3 Beds ⋅ 3 Baths ⋅ Storey Lake Tr K SubDv. ⋅ 34746 Zip Code
Virtually Staged. Welcome Home to 2935 Theme St! Move-in ready, this 3-bedroom, 2.5-bath townhome offers 1,859 sq ft of open-concept living in the heart of Central Florida. From the moment you arrive, the home's charming coastal-craftsman exterior — with paver driveway and manicured landscaping — sets the tone for what's inside... Step through the front door into a spacious great room that flows seamlessly into the kitchen and dining area, all finished with tile flooring throughout the main level. The kitchen features espresso cabinetry, stainless steel appliances, a subway tile backsplash, and a center island with pendant lighting. Upstairs, the primary suite offers a peaceful retreat with a tray ceiling, walk-in closet, and en-suite bath, while two additional bedrooms provide flexible space for family, guests, or a home office. A convenient half bath downstairs and in-unit laundry add everyday functionality. Outside, enjoy a private patio and an insulated 2-car garage that stays cool year-round. HOA includes access to a community pool, dog park, cable, and WiFi. Located just minutes from Orlando's world-famous attractions, shopping, dining, and major highways, this townhome combines comfort, style, and unbeatable convenience. Don't miss this one and schedule your private showing today!

2935 Theme Street, Kissimmee
$144,900
1 Beds ⋅ 1 Baths ⋅ Gables At Lakeside Condo SubDv. ⋅ 34741 Zip Code
Discover a fantastic lake-view opportunity at The Gables at Lakeside in the heart of Kissimmee! Located on the second floor, this condominium offers beautiful water views, a feature not available with every unit in the community. The HVAC system was replaced in 2025, providing a valuable recent update. Currently vacant and ready for a quick closing, the property was previously leased for $1,575 per month, offering flexibility for an owner-occupant or investor. Community amenities include a swimming pool and tennis courts. Enjoy comfortable condominium living with a scenic lake view and convenient access to all that Kissimmee has to offer.

1229 Bermuda Lakes Lane Unit 206, Kissimmee
$889,999
7 Beds ⋅ 6 Baths ⋅ Split Oak Estates Ph 2 SubDv. ⋅ 34771 Zip Code
Wow!! 5,486 square feet under air! This is a true 7 bedroom 5/1/2 bathroom home with a full size loft and game room! This home is still under the builder warranty and is fully equipped with all the appliances, water filtration system and tons of storage space. There are 2 master suites. All the bedrooms have a private walk-in closet and 3 bedrooms have an onsuite bathroom. There are too many upgrades to list with a kitchen equipped for entertaining with a waterfall island, quartz countertops and stainless steel appliances. The showpiece of this beautiful home is the large backyard paver patio with a full size outdoor kitchen. The extended paver patio is 50x25! All this in the growing Sunbridge area but without expensive HOA fees and no CDD fee.

2764 Matera Drive, St Cloud
$439,900
4 Beds ⋅ 2 Baths ⋅ Wyndham Palms Ph 3 SubDv. ⋅ 34747 Zip Code
Do you visit Orlando so much that it simply makes more sense to own a vacation home there?  Do you often stay at hotels and Airbnbs and wish you had more of a "home" feel to enjoy your stay?  If you answered yes to any of these.....then 2220 Wyndham Palms Way in Kissimmee could be your next home away from home!  Securely located in a 24-hour guard-gated community, this fully furnished home has just undergone a very successful renovation and is now ready for its new owners.  Once across the threshold you can instantly appreciate the sellers have done for you; starting with a 100% updated kitchen that includes new quartz countertops, new cabinetry, new hardware, floating shelves and updated appliances, making this an entertainer's dream.  New laminate flooring leads you from the entryway and throughout the entire home, leaving not one stitch of carpet to walk on or worry about cleaning.  A two-way split floor plan creates additional privacy, with the primary bedroom located on the right side of the home, tastefully updated with custom woodwork and sconces that flank the brand new bedroom set.  Your hotel-like en-suite bathroom does not fall short in any way; and has matching quartz and cabinetry as the kitchen and secondary bathroom.  Three other generously sized bedrooms are on the opposite side of the home, each with its own brand new bedroom set and serviced by its own, very well-updated bathroom.  A thoroughly outfitted game room includes a billiards table, games for your guests, as well as its own private TV.  If you're ready to enjoy the Florida sun, this stunning back patio and pool area will not disappoint!  Tea lights set the backdrop for movie night by the pool, where you can create endless memories with your friends and family, and have guests leaving 5 stars after their stay.  > BRAND NEW FURNITURE | 100% UPDATED KITCHEN & BATHROOMS | LAMINATE FLOORING THROUGHOUT | 2018 ROOF | 2021 HVAC | 2024 POOL PUMP | 2020 POOL HEATER | 2022 WATER HEATER | < UP TO 70% OCCUPANCY & POTENTIAL NOI OF $35,000+.  Don't you deserve to own a piece of the Florida sunshine in 2026?

2220 Wyndham Palms Way, Kissimmee
$649,000
5 Beds ⋅ 4 Baths ⋅ Bellalago SubDv. ⋅ 34746 Zip Code
Virtually Staged. Stunning LAKEFRONT estate on an oversized .44-acre premium lot in the resort-style, guard-gated community of Bellalago. Nestled directly along the shores of Lake Tohopekaliga on the scenic Kissimmee Chain of Lakes. This home has "WOW" factor and offers exceptional waterfront living and access to one of Central Florida’s most iconic lake systems. This beautifully maintained home offers a multi-generational floor plan featuring 5-bedrooms, 4-bathrooms as well as a dedicated office and offers high end upgrades throughout. The first-floor features 4 bedrooms, 3 bathrooms, and an office, while the spacious upstairs bonus room serves as a 5th bedroom with an en-suite full bath. Gorgeous wood flooring, a fully fenced backyard, and an expansive screened patio with a summer kitchen and jacuzzi. This home is perfect for entertaining. The sellers have replaced all bedroom carpeting, installed engineered wood on the stairs, and refreshed the handrails with new spindles for a refined look. The kitchen impresses with newly upgraded granite countertops, a stylish backsplash, and added cabinetry including a 9'6"×24" white shaker cabinet. Lighting has been modernized with new pendants and a chandelier, complemented by a new sink and spray faucet. Additional updates include fresh interior paint, a charming barn door in the laundry room, premium wood pantry shelving, and custom closet organizers, including a redesigned primary closet with wood shelving and rods for enhanced storage. Bellalago offers a true resort-style experience along the scenic shores of Lake Toho, known for its world-class bass fishing. Community amenities include multiple pools, fitness center, lakeside clubhouses, on-site dining, tennis and basketball courts, walking trails, and a private boat ramp with direct lake access. Families enjoy the water park and zero-entry pool, while residents appreciate 24-hour security. CABLE AND INTERNET ARE INCLUDED! This home is a must see!

1511 Gateway Lane, Kissimmee
$259,500
3 Beds ⋅ 3 Baths ⋅ Ashley Park At Harmony SubDv. ⋅ 34773 Zip Code
Amazing 3-bedroom and 2 ½ bath townhome, which includes a large 2-car garage. Stainless Steel Appliances, fresh paint around the house. This unit has an amazing front view of the golf course. Harmony has A-rated K-12 schools in walking distance, this home offers spacious living with both a formal living room and family room. and a closet pantry. Water and Recreation Buck Lake and Cat Lake: Access to community-owned boats, canoes, and kayaks via a free reservation system. Lakeshore Park: Features a splash pad, basketball, sand volleyball, and shuffleboard courts. community Swimming Pool and clubhouse. Sports and Nature Harmony Golf Preserve: An 18-hole championship golf course designed by Johnny Miller with the Champions Grill restaurant. Trails: Over 12 miles of paved and shaded walking, hiking, and bicycle paths. Other Outdoor Spaces: Dog parks, community gardens for growing vegetables, Town Center and Daily Services. Harmony Town Square: A central gathering space featuring an amphitheater, green spaces, shops, and professional services. Schools: On-site schools covering kindergarten through high school (Harmony Community School, Harmony Middle School, and Harmony High school). local coffee shop, pizza place, and Mexican restaurant, important nearby areas such as Orlando International Airport, Medical City in Lake Nona, 35 miles to the Beaches, Great location. Buyer to verify all measurements. so much to enjoy

7108 Five Oaks Drive, Harmony
$559,999
4 Beds ⋅ 3 Baths ⋅ Split Oak Estates SubDv. ⋅ 34771 Zip Code
Virtually Staged. This is the kind of home that makes an immediate impression; nearly 2,900 square feet of beautifully connected, single-story living with the space, style, and flexibility to truly settle in. Located in Split Oak Estates, this 4-bedroom, 2.5-bath home opens into an expansive great room where tray ceilings, recessed lighting, and wide-open sightlines create a bright, airy setting for both quiet evenings and memorable gatherings. At the center of it all is a showpiece kitchen designed to bring everyone together, featuring an oversized quartz island with generous seating, crisp white cabinetry, stainless steel appliances, double wall ovens, a statement vent hood, tile backsplash, and a walk-in pantry with exceptional storage. Two sets of oversized sliding glass doors blur the line between indoors and out, leading to a nearly 35-foot-long screened lanai. This impressive outdoor retreat offers plenty of room for dining and lounging, plus a built-in serving counter with a sink, storage cabinetry, an included undercounter wine refrigerator, and a dedicated adjacent space for a future grill. Beyond the screen enclosure, the fully fenced backyard is ready for play, pets, gardening, or simply enjoying the Florida sunshine. The oversized primary suite feels like a private escape with its tray ceiling, spacious bath, dual-sink granite vanity, walk-in shower, and an exceptionally large walk-in closet. Three additional bedrooms are thoughtfully separated for privacy, including a front bedroom with a closet that is perfectly positioned to serve as a quiet home office, study, or guest room. Tile flooring extends through the main living spaces and primary suite, while the secondary bedrooms offer soft carpeting. An interior laundry room with an included washer and dryer, attached garage, paver driveway, and polished low-maintenance landscaping add everyday convenience and curb appeal. Split Oak Estates rounds out the lifestyle with a community pool, playground, walking paths, and scenic ponds, all from a convenient St. Cloud location near the Lake Nona corridor, shopping, dining, and major roadways. Spacious without feeling overwhelming, polished without sacrificing comfort, and designed for the way people truly live—2754 Matera Drive is ready to feel like home.

2754 Matera Drive, St Cloud
$595,000
4 Beds ⋅ 5 Baths ⋅ Reunion Ph 02 Prcl 01 & 1a SubDv. ⋅ 34747 Zip Code
Virtually Staged. Exceptional 4-bedroom, 5-bathroom home on Arnold Palmer Championship Course (Hole 5) in gated Reunion Resort. This property features fresh interior paint, brand-new kitchen appliances, granite kitchen and bathroom surfaces, new washer/dryer in the primary residence, plantation shutters throughout, and 2-car garage. Open floor plan with soaring ceilings and natural light flows from the gourmet kitchen with granite countertops to spacious living areas perfect for entertaining, enhanced by a ceiling speaker system. Primary suite upstairs features spa-inspired ensuite with dual sinks, jetted soaking tub, and stand-up shower, large walk-in closet, plus private golf course balcony. Two additional bedrooms upstairs with another full bathroom accommodate family or guests. Separate fully-equipped in-law suite with one bedroom, full bathroom, kitchenette, and living room featuring private entrance—ideal for extended guests or rental income. Heated and cooled resort-style pool sits in fully fenced courtyard with vinyl fencing, covered patio for al fresco dining, and half pool bath. Reunion Resort community offers three championship golf courses, water park, lazy rivers, wave pools, luxury spa, tennis, and fitness centers. HOA covers lawn care, irrigation, pest control, high-speed internet, cable, pressure washing, and 24-hour gated security. Zoned for short-term rentals with excellent cash flow potential. Minutes from I-4, 429, and Central Florida attractions. Perfect as primary residence, vacation retreat, or investment property. Property does not include resort membership. Up to 1% towards buyer's closing costs if using Seller's preferred lender, terms and conditions apply.

7526 Excitement Drive, Reunion
$335,000
3 Beds ⋅ 3 Baths ⋅ Villas At Reunion Square Condo Ph 1 SubDv. ⋅ 34747 Zip Code
INVESTOR ALERT! TURNKEY! Welcome to 7602 Cabana Ct, located inside Reunion Resort in Florida. This ground-floor, three-bedroom, three-bathroom condo is sold fully furnished, fully equipped, and move-in ready for a new owner or vacation rental guests. The property features an ACTIVE GOLD MEMBERSHIP and comes with an established rental history along with future guest bookings already scheduled, giving you an active rental setup from day one. INTERIOR FEATURES: Fresh interior paint was completed throughout the home in June 2023. Custom plantation shutters are installed on every window, providing a clean look, light control, and easy care with no curtains to wash. The living area features power-reclining sofas purchased in Fall 2023, paired with newer furniture, modern decor, and clean linens throughout. KITCHEN AND DINING: The kitchen is well equipped with modern major appliances, all replaced recently including the refrigerator in June 2023, dishwasher in January 2024, stove in May 2024, and garbage disposal in July 2024. Generous cabinet space and a practical layout make daily cooking and guest hosting easy. BATHROOM UPGRADES: All three bathrooms feature functional, high-quality updates including updated plumbing fixtures and new toilets installed in June 2023, custom mold- and mildew-resistant master bathroom glass doors installed by Dixie Shower Doors in Fall 2023, and quiet LED exhaust fan and light combinations installed in the primary and main bathrooms. An extra matching fan and light kit is stored in the owner storage closet next to the front door, ready for the Jack-and-Jill bathroom when needed in the future. STORAGE AND UTILITIES: Storage is maximized throughout with custom closet builds in all three bedrooms. Outside, right next to the front entry door, you will find a dedicated locked storage closet featuring built-in shelving and interior lighting—ideal for owner lock-off supplies. MAJOR HOME SYSTEMS: The HVAC system was replaced in August 2021 and is currently covered under a service contract. An Ecobee smart thermostat is installed, allowing remote temperature settings from your phone app. The water heater was replaced in June 2023 and is currently under warranty and a service contract. SECURITY AND CONVENIENCE: A full Ring security system is installed and included. It features a battery backup power system, a front video doorbell, and a back porch security camera. The front doorbell camera clear view covers the entry and owner storage closet door for added security while away. THE RESORT LOCATION: Reunion Resort is known for world-class golf courses, a water park, swimming pools, on-site dining, and close distance to Central Florida attractions. Having the active Gold Membership on this property allows access to these resort amenities for owners and authorized guests. Whether you want a fully setup vacation rental asset, a personal getaway, or a turnkey full-time home in Reunion, this spacious 3/3 unit offers recent updates across every major system and low-maintenance living. Schedule your private showing today to tour 7602 Cabana Ct, Unit 101.

7602 Cabana Court Unit 101, Kissimmee
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