Osceola Homes with Pool

Osceola Homes with Pool

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, diverse wildlife, and an array of recreational opportunities. From the enchanting shores of Lake Tohopekaliga to the lush expanses of the Kissimmee Prairie Preserve, this county is a haven for nature enthusiasts and adventure seekers alike.

Osceola County is not just about breathtaking scenery; it also boasts a rich cultural tapestry, with charming towns like Kissimmee and St. Cloud offering delightful shopping, dining, and entertainment options. Whether you’re exploring the historic downtown areas or enjoying the vibrant local festivals, there’s always something happening in this dynamic community.

For those seeking the ultimate Florida lifestyle, homes with pools in Osceola County are a perfect choice. Imagine basking in the warm sunshine, lounging by your private pool, and hosting unforgettable summer barbecues. These homes offer a sanctuary of relaxation and fun, providing the ideal backdrop for family gatherings or serene evenings under the stars. With a variety of styles and sizes to choose from, you’re sure to find the perfect pool home that fits your needs and desires.

Living in Osceola County means embracing a lifestyle filled with outdoor activities, friendly neighborhoods, and a strong sense of community. Whether you’re a first-time homebuyer or looking to invest in a vacation rental, Osceola County’s homes with pools are waiting to welcome you into the sunshine. Discover your dream home today and experience the magic of living in this enchanting Florida paradise!

Newest Osceola Homes with Pool

4 Beds ⋅ 4 Baths ⋅ Cumbrian Lakes Resort Ph 3 SubDv.

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

4 Beds ⋅ 3 Baths ⋅ The Meadow At Crossprairie SubDv.

Under Construction. Brand new, energy-efficient home available by Sep 2026! Entertain guests in a Lotus with an open kitchen that overlooks the dining and great room. The first-floor flex space can be best used to fit your family's needs. The upstairs primary suite features an oversized walk-in closet. The Meadow at Crossprairie is a community of new single-family homes for sale in St. Cloud, FL. This offers easy access to the Turnpike, major employment centers, & great schools. Each of our homes is built with innovative, energy-efficient features designed to help you enjoy more savings, better health, real comfort and peace of mind.

4524 Eagle Perch Court, St Cloud (Narcoossee Road)

1 Beds ⋅ 1 Baths ⋅ Villas Del Sol At Kissimmee Condo SubDv.

Beautiful freshly painted and well-maintained 1-bedroom, 1-bath condo with a bonus room, the unit is located in the gated, resort-style community of Villa del Sol, with controlled access through the Envera system. The unit is in the first floor with direct access to parking. This unit has been fully renovated with laminate flooring throughout the entire unit. The bedrooms has spacious walk-in closets. The community buildings have recently been updated with a modern exterior color palette and is very well maintained. Amenities include a clubhouse, fitness center, two swimming pools, on-site laundry facilities, car wash area, BBQ/picnic areas, playground, tennis courts and much more. Excellent opportunity for primary residence or investment. Located near to the Loop Mall with very close access to the Osceola Parkway, 192, 4-17, I-4, Restaurants, parks and attractions. Unit is VACANT. Move-in ready.

2208 Antigua Place Unit 914, Kissimmee

3 Beds ⋅ 3 Baths ⋅ Compass Bay Unit 1 SubDv.

Newly furnished and equipped 3 bedroom, 3 bath townhome in Compass Bay, with a 3-year-old A/C. Three full baths is unusual for this price point and a real advantage for both long-term and short-term rental demand. Compass Bay is one of the more versatile communities in the area — live in it full time, lease it long term, or run it as a short-term rental. The gated community has mature landscaping and a pool close to the unit, and the resident mix is a healthy blend of full-time owners and short-term guests, so it doesn't feel like a transient complex. The unit is currently operating as an Airbnb. All furnishings — over $15,000 worth, purchased new — convey with the sale. Proximity to the parks adds steady rental pull for owners who want to keep it as an income property. Whether the goal is a primary residence, a long-term rental, or a vacation rental with furnishings already in place, this one is ready to go from day one.

3087 Seaview Castle Drive, Kissimmee

3 Beds ⋅ 3 Baths ⋅ Heritage Key Villas Ph 1 & 2 SubDv.

Check out this modern open floor concept townhouse. You will be welcome by a freshly painted interior featuring 3 bedrooms and 2.5 baths. This layout is ideal for family and friends to gather. The kitchen features an island (with granite counter top), pantry, and plenty of cabinet space. The living area has a sliding door that leads to a screened patio with no rear neighbors. All bedrooms are located on the second lever, adding additional privacy to the family. The master bedroom features an en-suite bath, and built-in closet. Another full bathroom is located on the second floor for your convenience. You will love the gated community of Heritage Key. There are plenty of amenities including a clubhouse, pool table, beach volleyball, playground, pool & spa to name a few. This convenient location offers easy access to 192, shopping, and dining. You will be only minutes to the fast growing area or NeoCity, Silver Spurs Arena, and FL Turnpike. Carpets are 2 years old and have just been steamed clean; faucets in bathrooms sinks have just been replaced. See it today!

2080 Heritage Key Boulevard, Kissimmee

8 Beds ⋅ 5 Baths ⋅ Storey Lake 2 50 Resort SubDv.

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

5 Beds ⋅ 4 Baths ⋅ Marbella Ph 1 SubDv.

Welcome to this exceptional 5-bedroom, 3.5-bathroom home located in the desirable Marbella community of Kissimmee. Built in 2020 and situated on a premium corner lot, this beautifully upgraded residence offers over 2,600 square feet of thoughtfully designed living space, blending modern style, functionality, and energy efficiency. From the moment you arrive, you'll appreciate the home's attractive curb appeal, highlighted by a paved driveway, a modern front door, and upgraded soffit lighting that enhances the exterior day and night. Inside, the open-concept floor plan is designed for today's lifestyle, featuring updated flooring throughout with no carpeting, creating a clean, contemporary feel. The heart of the home is the stunning remodeled kitchen, complete with upgraded cabinetry, a custom display cabinet, designer backsplash, a large center island with seating, and abundant prep and storage space. Flowing seamlessly into the spacious living and dining areas, this layout is ideal for everyday living and entertaining. A stylish dry bar adds the perfect touch for hosting guests or creating your own coffee or beverage station. Upstairs, a spacious loft provides the flexibility to serve as a media room, game room, home office, or additional living area. The thoughtfully designed floor plan includes five generously sized bedrooms and 3.5 bathrooms, including a beautifully remodeled guest bathroom featuring floor-to-ceiling tile finishes. This home is loaded with premium upgrades designed for comfort, convenience, and efficiency, including a solar energy system to help reduce utility costs, a whole-house salt-based water filtration system, and an under-sink reverse osmosis system that provides alkaline drinking water. Smart home features include Nest thermostats and a security camera system, offering modern convenience and peace of mind. Step outside to enjoy the expansive, fully fenced backyard, providing plenty of space for outdoor entertaining, pets, play, or even the future pool you've always envisioned. Ideally located with easy access to FL-417, this home offers exceptional convenience to everyday essentials and Central Florida's top destinations. Enjoy being just minutes from shopping, supermarkets, restaurants, the Lake Nona Medical City district, Nona Adventure Park, and Orlando International Airport, making commuting, travel, and entertainment incredibly convenient. Combining stylish upgrades, energy-efficient features, spacious living areas, and a prime location, this move-in-ready Marbella home is an outstanding opportunity you won't want to miss. Schedule your private showing today!

2824 Noble Crow Drive, Kissimmee

2 Beds ⋅ 2 Baths ⋅ Northwest Lakeside Groves Ph 2 SubDv.

Welcome to 2286 Datura Loop, St. Cloud, FL—a beautifully maintained home offering the perfect combination of comfort, style, and convenience. This inviting residence features a thoughtfully designed floor plan with bright, open living spaces that are ideal for both everyday living and entertaining. The spacious kitchen provides ample cabinet and counter space while overlooking the main living and dining areas, creating a seamless flow throughout the home. The primary suite offers a private retreat with an en-suite bath and generous closet space, while the additional bedrooms provide flexibility for family, guests, or a home office. Step outside to enjoy the backyard, offering plenty of room for relaxing, gardening, or outdoor gatherings. Conveniently located near shopping, dining, schools, parks, and major roadways, this home also provides easy access to Lake Nona, Orlando International Airport, Medical City, and Central Florida's world-famous attractions.

2286 Datura Loop, St Cloud (Narcoossee Road)

4 Beds ⋅ 3 Baths ⋅ Storey Lake Ph 2 SubDv.

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

5 Beds ⋅ 4 Baths ⋅ Windsor At Westside SubDv.

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

3 Beds ⋅ 3 Baths ⋅ Oakwater Condo Ph 7-10 SubDv.

ONLY MINUTES FROM WALT DISNEY WORLD! Freshly painted and featuring brand-new carpet, this spacious 3-bedroom, 2.5-bath, two-story condo offers 1,808 square feet of comfortable living space and a private one-car garage. The main level features generous living and dining areas, a convenient powder room, and a well-appointed kitchen with all appliances included, a breakfast bar, closet pantry, and cozy breakfast nook. The adjoining family room opens to a screened lanai overlooking beautifully maintained greenery an inviting setting to relax and unwind. Upstairs, double doors welcome you into the spacious primary suite with a private bath and glass-enclosed shower. Two additional bedrooms share a second full bathroom. Located within the gated, resort-style Oakwater community, residents and guests enjoy exceptional amenities, including a lagoon-style pool, spa, clubhouse, fitness center, game room, playground, splash pad, tennis and basketball courts, sand volleyball, and walking trails. Conveniently located near shopping, dining, major roadways, and Central Florida’s world-famous attractions. With the flexibility to serve as a primary residence, vacation retreat, or short- or long-term rental investment, this property offers an outstanding opportunity in a highly desirable location. Schedule your private showing today!

7509 Pellham Way, Kissimmee

3 Beds ⋅ 2 Baths ⋅ Remington Prcl G Ph 2 SubDv.

Golf-course investment opportunity in Remington. This well-positioned three-bedroom, two-bath single-family home offers approximately 1,816 square feet of living area, a new roof installed in 2026, direct golf-course views and a covered rear lanai. The property is currently leased at $1,925 per month through February 28, 2027 and is being offered subject to the existing lease. Remington community amenities include golf, recreation facilities, pool, tennis courts and walking trails, subject to HOA confirmation. Conveniently located near Florida’s Turnpike, shopping, schools and dining. Seller will consider up to $5,000 toward buyer closing costs with an acceptable offer, subject to contract terms and lender approval. Property is being sold as-is with the buyer’s right to inspect.

119 Southampton Drive, Kissimmee

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