Osceola Homes with Private Pool type

Osceola Homes with Private Pool type

Welcome to Osceola County, Florida – a vibrant and picturesque region that perfectly blends natural beauty with modern living. Nestled in the heart of Central Florida, Osceola County is renowned for its stunning landscapes, rich cultural heritage, and an abundance of recreational activities. From the enchanting wetlands of the Kissimmee River to the thrilling attractions of nearby Orlando, this county offers something for everyone.

Osceola is not just a destination; it’s a lifestyle. The county boasts a variety of charming neighborhoods, each with its unique character and appeal. For those seeking a slice of paradise right at home, consider the allure of homes with private pools. Imagine stepping into your backyard oasis, where you can unwind, entertain, or simply bask in the Florida sunshine. These homes provide the ultimate retreat, allowing you to enjoy leisurely afternoons by the poolside or host unforgettable gatherings with friends and family.

Whether you’re looking for a cozy villa or a spacious family home, Osceola County’s real estate market offers a diverse range of properties, many featuring luxurious private pools. With close proximity to world-famous attractions, top-rated schools, and a thriving community, living in Osceola means embracing a lifestyle that emphasizes both relaxation and adventure.

Don’t miss your chance to experience the best of Florida living. Explore the exquisite homes with private pools in Osceola County today, and discover your perfect sanctuary in this enchanting region!

Newest Osceola Homes with Private Pool type

$560,000
4 Beds ⋅ 3 Baths ⋅ Cove At Storey Lake 5 SubDv. ⋅ 34746 Zip Code
Turnkey Vacation Rental Opportunity in Storey Lake! Welcome to 4383 Scene Lane, Kissimmee—a beautifully furnished 4-bedroom, 3-bathroom townhome in the highly sought-after Storey Lake Resort Community, just minutes from Central Florida's world-famous attractions. Whether you're looking for a high-performing short-term rental or a fully furnished vacation home, this property is ready to impress from day one. Thoughtfully designed with vacation guests in mind, the current owners have professionally furnished and decorated the home to create an unforgettable experience. Everyone will love the Harry Potter-themed bedroom and Mickey Mouse-themed bedroom, while the tranquil beach-themed suite provides the perfect place to relax after a day at the parks. The home also features a spacious, fully equipped kitchen with stainless steel appliances, making it easy to prepare meals and entertain family and friends. Step outside to your own private oasis featuring a heated pool, perfect for unwinding after exploring nearby attractions. Sold fully furnished, this home is truly turnkey and ready to continue operating as a successful vacation rental. Located approximately 10 minutes from Walt Disney World® Resort and with convenient access to Universal Orlando Resort and SeaWorld Orlando, Storey Lake is one of Central Florida's premier resort communities. Residents and guests enjoy an exceptional array of resort-style amenities, including: Resort-style swimming pools with thrilling water slides and a lazy river Two clubhouse amenity centers, including one featuring a pirate-themed pool Tiki bar Fitness center Sports courts Mini golf Kayaking and water recreation Whether you're expanding your investment portfolio or searching for the perfect vacation retreat, this exceptional Storey Lake townhome offers the ideal combination of location, luxury, and income-producing potential. Schedule your private showing today and discover why this property is the perfect place to vacation, invest, and create lasting memories.

4383 Scene Lane, Kissimmee
$424,999
4 Beds ⋅ 4 Baths ⋅ Cumbrian Lakes Resort Ph 3 SubDv. ⋅ 34746 Zip Code
Virtually Staged. Short Sale. One or more photos have been virtually staged. Welcome to this beautiful home located in the exclusive gated community of Cumbrian Lakes, one of Kissimmee's most sought-after neighborhoods for short-term vacation rentals and investment properties. This spacious home features an open-concept floor plan, making it ideal as a primary residence, vacation home, or income-producing investment property. The heart of the home is the well-appointed kitchen, featuring stainless steel appliances, a large breakfast island, and seamless flow into the living room, dining area, and covered lanai—creating the perfect space for entertaining. Step outside to your private screened pool, where you can relax and enjoy Florida's year-round sunshine. High ceilings fill the home with abundant natural light, while the split-bedroom floor plan provides added privacy. The garage has been professionally converted into a climate-controlled living space with air conditioning and heating, adding approximately 440 square feet of additional living area—ideal for a game room, home office, fitness room, or flexible living space. The spacious primary suite offers direct access to the lanai and pool and features an en-suite bathroom with a garden tub, separate walk-in shower, and walk-in closet. Bedrooms two and three share a Jack-and-Jill bathroom, while the fourth bedroom is conveniently located near another full bathroom. An additional half bathroom and an outdoor poolside shower provide extra convenience for family and guests. The covered lanai includes a ceiling fan and lighting, making it the perfect place to enjoy outdoor living throughout the year. Lawn maintenance is included in the HOA fee, offering added convenience and low-maintenance ownership. Ideally located just minutes from Walt Disney World, Universal Orlando Resort, SeaWorld Orlando, shopping, dining, major highways, and the SunRail station, this property offers exceptional convenience and accessibility. Cumbrian Lakes is a highly desirable gated community that allows short-term rentals, making it an outstanding opportunity for investors seeking strong rental potential or buyers looking for a vacation home in the heart of Central Florida. Don't miss this exceptional opportunity to own a property in one of Kissimmee's premier vacation rental communities!

4806 Cumbrian Lakes Drive, Kissimmee
$770,000
8 Beds ⋅ 5 Baths ⋅ Storey Lake 2 50 Resort SubDv. ⋅ 34746 Zip Code
Turnkey and fully furnished, this impressive 8-bedroom, 5-bathroom vacation home is located in the highly desirable Storey Lake Resort—just minutes from Walt Disney World, Disney Springs, shopping, dining, and Orlando's top attractions. With over 4,300 square feet of thoughtfully designed living space, the home features an open-concept floor plan, two spacious primary suites, a large loft, and a private screened pool and spa, making it ideal for large groups and vacation guests. Whether you're expanding your portfolio or searching for a second home that generates income, this property offers outstanding short-term rental potential in one of Central Florida's premier resort communities. Owners and guests enjoy world-class amenities, including a lazy river, water slides, resort-style pools, fitness center, mini golf, sports courts, playgrounds, and a tiki bar. Don't miss this opportunity to own a high-demand vacation home in one of Orlando's most sought-after resort destinations.

4536 Target Boulevard, Kissimmee
$1,230,000
5 Beds ⋅ 5 Baths ⋅ Celebration North Village Unit 6 SubDv. ⋅ 34747 Zip Code
Rare Space. Endless Possibilities. One of Celebration's Best Values. Welcome to one of the most versatile homes available in Celebration—the town Disney built. 5 bedrooms, 4.5 bathrooms and 3,418 square feet, this exceptional residence combines generous living space, luxury features, income potential, primary first floor suite, pool, game room, sun deck, garage apt and 3 car garage. Inside, you'll discover hardwood flooring, custom moldings, abundant natural light. The heart of the home is an impressive Chef's Kitchen featuring: • Massive granite center island • Premium GE Monogram appliances • Coveted Sub-Zero refrigerator • Gas cooktop • Warming drawers • Generous custom storage • Open concept design ideal for entertaining family and friends. The spacious family room with a cozy gas fireplace flows seamlessly into the formal dining room, while a dedicated home office offers an ideal work-from-home space or optional additional bedroom. The first-floor owner's retreat is a rare find in Celebration, featuring dual closets, an ensuite bath, direct backyard access, and even a private stacked washer and dryer tucked inside the walk-in closet for ultimate convenience. Upstairs, two oversized bedrooms share an expansive Jack-and-Jill bathroom, while an additional laundry room adds everyday convenience. A detached pool suite with its own entrance, kitchenette, and full bathroom creates endless opportunities as • Guest suite • In-law quarters • Home gym • Art studio • Private office • Media room • Teen retreat. Above the attached 3-car garage, you'll discover a completely separate 1-bedroom apartment complete with • Private entrance • Full kitchen • Full bathroom • Washer & dryer • Expansive second-story deck. Whether used for visiting family, multigenerational living, a private executive office, or rental income, this apartment adds tremendous long-term value. Your own backyard retreat features a beautiful heated pool and spa surrounded by elegant brick pavers—perfect for relaxing after a day at the parks or entertaining guests year-round in Florida's sunshine. Buy with confidence knowing several important improvements have already been completed, including: • New Roof (2021) • Fresh interior paint • Routine HVAC maintenance • Water system maintenance. Located just steps from North Village Park, playgrounds, volleyball courts, athletic fields, and the community pool, you'll enjoy one of Celebration's most beloved neighborhoods. As a Celebration resident you'll also enjoy: Six community pools, Tennis & pickleball courts, Fitness centers, More than 20 miles of walking and biking trails, Beautiful parks and lakes, Year-round community events, charming downtown Celebration with restaurants, boutiques, coffee shops and entertainment. With quick access to I-4, SR-417, US-192, Walt Disney World, Orlando International Airport, and Central Florida's world-famous attractions, the location is as convenient as it is beautiful. Homes with this much flexibility are incredibly difficult to find in Celebration. Between the first-floor primary suite, detached pool suite, private apartment, three-car garage, heated pool and outstanding North Village location, this property checks boxes that very few homes can. Whether you're looking for multigenerational living, guest accommodations, rental income, or simply room to spread out, 205 N Village Street delivers exceptional value and endless possibilities in one of Florida's most iconic hometowns.

205 N Village Street, Celebration
$450,000
4 Beds ⋅ 3 Baths ⋅ Storey Lake Ph 2 SubDv. ⋅ 34746 Zip Code
Turnkey and income-producing, this recently renovated 4-bedroom, 3-bathroom townhome is located in Storey Lake Resort, one of Central Florida’s most desirable short-term rental communities. Offered fully furnished and professionally decorated, the home features a bright open-concept layout, an updated living area, granite countertops, stainless-steel appliances, and two private suites. Step outside to your screened-in private pool and covered lanai, the perfect place to relax after a day at the parks. Currently operating as a vacation rental, this property is ready for its next owner to enjoy and generate income from day one. Storey Lake offers resort pools, lazy rivers, waterslides, clubhouses, fitness centers, mini-golf, tiki bars, playgrounds, and sports courts—all just minutes from Walt Disney World, shopping, dining, and entertainment. An exceptional opportunity for a vacation retreat or investment property near Disney. Schedule your showing today!

3080 Juliet Drive, Kissimmee
$525,000
5 Beds ⋅ 4 Baths ⋅ Windsor At Westside SubDv. ⋅ 34747 Zip Code
Located within the highly sought-after Windsor at Westside gated resort community, this fully furnished home offers flexibility as a primary residence, vacation getaway, or income-producing short-term rental. The property is already set up for Airbnb use and is being sold turnkey, allowing for immediate occupancy or continued rental operations. The home offers five bedrooms and four bathrooms, along with a game room and an open, airy floor plan designed for both comfort and functionality. The layout easily accommodates large groups, with multiple spaces to gather or unwind throughout the home. A private first-floor suite provides a quiet retreat, while the kitchen features modern finishes including granite counters and stainless steel appliances. Outdoors, a private pool to create the perfect place to relax at any time of day. Owners and guests enjoy access to a wide range of resort amenities, including a full-service clubhouse, lake and pier, expansive zero-entry pool, water slide, lazy river, splash area, fitness center, sports courts, arcade, and on-site convenience shop. Conveniently positioned near Disney and major attractions, this home combines location, lifestyle, and investment potential in one exceptional opportunity.

2440 Tangier Drive, Kissimmee
$299,000
2 Beds ⋅ 2 Baths ⋅ Indian Ridge Villas Ph 1 SubDv. ⋅ 34747 Zip Code
Beautifully Updated Home Minutes from Disney – Ideal Primary Residence, Vacation Home, or Investment Opportunity!Welcome to this beautifully 2-bedroom, 2-bathroom home located in the desirable Kissimmee area, just minutes from Walt Disney World. This move-in-ready property offers a perfect blend of comfort, functionality, and investment potential.The home features an updated knockdown ceiling texture throughout, replacing the original finish for a fresh, modern look. The spacious living areas flow seamlessly into the kitchen and comfortable bedrooms.Enjoy Florida living in your private backyard featuring a refreshing swimming pool with a recently replaced pool pump, perfect for relaxing or entertaining. The fully fenced yard provides added privacy and security.Additional recent improvements include a newer air conditioning system, offering energy efficiency and peace of mind. The garage has been professionally converted into a versatile bonus room complete with its own mini-split air conditioning unit and upgraded electrical panel, making it ideal for a home office, game room, fitness area, guest space, or hobby room.Conveniently located just minutes from Disney, this property presents an outstanding opportunity for investors seeking short-term rental income (subject to local regulations and community restrictions). Easy access to SR 429, I-4, shopping, dining, entertainment, and Central Florida's world-famous attractions makes this an exceptional location for both residents and visitors alike.Don't miss the opportunity to own this beautifully updated home in one of Central Florida's most sought-after locations!

7732 Water Oak Ct, Kissimmee
$380,000
4 Beds ⋅ 3 Baths ⋅ Stoneybrook South Ph I-1 & J-1 SubDv. ⋅ 33896 Zip Code
If you're looking for peaceful living in a resort-like community, look no further than the Retreat at Champions Gate. This beautiful 4-bedroom, 3-bath home is move-in ready and allows for short-term rentals. The freshly updated interior boasts a gorgeous open-concept layout and bright interior. Upon entering, you'll notice 10' ceilings. A large open kitchen is the heart of your home with quartz countertops and stainless steel appliances, a peninsula, and a vented range with both 42-inch and floor-to-ceiling cabinetry. Featuring a ground-floor private suite facing north. You will enjoy dual sinks with a vanity and a large walk-in shower. The additional 3 bedrooms are nicely sized and well located upstairs, offering plenty of space for family or guests. Make your way out back where you will love spending time relaxing in the screen-enclosed pool. Only minutes from Disney and Universal Resorts and Disney City Walk. The HOA includes cable, high-speed internet, a resort-style pool and splash pad, mini-golf, arcade, ice cream shop, restaurant and bar, fitness center, playgrounds, and a dog park. This is a Fannie Mae Homepath property.

1592 Moon Valley Drive, Davenport
$525,000
5 Beds ⋅ 5 Baths ⋅ Paradise Palms Resort Ph 4 SubDv. ⋅ 34747 Zip Code
**Exceptional 5-Bedroom Resort-Style Home in Prime Kissimmee Location!!!!This beautifully upgraded home at 2908 Banana Palm Dr puts you minutes from world-famous theme parks, shopping, restaurants, major roads, and the airport. Welcome to the perfect blend of comfort and convenience in one of Florida's most sought-after vacation destinations. Step inside this spacious 2-story home featuring over 3,000 square feet of thoughtfully designed living space. The grand entry showcases custom tile work and elegant shadow box molding that flows through the living room and dining area. Soaring vaulted ceilings and high ceilings throughout create an open, airy feel you'll love. The completely renovated kitchen is a chef's dream with brand new cabinets and porcelain countertops installed May 2025. Premium Forno appliances include a double wall oven, 36-inch French door electric range with convection, oversized 40-inch refrigerator, and a convenient microwave drawer built into the cabinetry. All five bedrooms offer comfortable retreats, with the primary bath featuring a modern bidet toilet. New LVP flooring runs throughout the entire home, while bedrooms feature cozy carpet. Recent upgrades include a new HVAC system (July 2025), hot water heater (April 2025), pool filter (November 2025), and washer/dryer (April 2025). Relax in your private screened pool and spa with privacy screens, backing up to a peaceful nature preserve. The resort-style community amenities are incredible: clubhouse, fitness center, Tiki bar, pool, two hot tubs, splash park, waterslide, movie theater, sauna, and sports courts. With over $100,000 in upgrades, this move-in ready home is approved for short-term rentals, making it perfect for personal use or investment income. Don't miss this incredible opportunity!

2908 Banana Palm Drive, Kissimmee
$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 luxury, privacy, and convenience in this stunning Mediterranean-inspired estate nestled within the exclusive gated enclave of a private boating community of only 24 custom residences. This one-of-a-kind property features a residential elevator, breathtaking canal views, direct access to the Chain of Lakes, a heated saltwater pool, a rare five-car split garage, and an extended driveway accommodating up to 11 vehicles, perfect for your boats, cars, RVs, and all your recreational toys. 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 with an elegant Juliet balcony. The home's impressive curb appeal is further enhanced by an extended driveway that comfortably accommodates 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 living 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 will convey with the home to 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. RSVP for the upcoming viewing event.

5229 Waterside Vista Lane, 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
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