Osceola County Homes with Pool

Osceola County 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 County Homes with Pool

2615 Chatham Circle, Kissimmee
$455,000
3 Beds ⋅ 2 Baths ⋅ Chatham Park At Sausalito Ph 2 SubDv. ⋅ 34746 Zip Code
Welcome to your turnkey, exceptional investment opportunity or move-in-ready dream home! This beautifully updated residence—sold "AS-IS" for a seamless transaction—perfectly blends resort-style comfort with ultimate convenience. No Carpet, FULLY FURNISHED with modern furniture and currently operating as a short-term rental, this property allows you to step right in and generate immediate revenue from day one, with no additional setup required. Every major mechanical and structural component has been recently upgraded to ensure years of worry-free ownership, including a new Carrier HVAC system (2020), a premium RainSoft water softener and filtration system (2021) that protects both you and the home's equipment, a new shingle roof (2023), a new A. O. Smith ProLine water heater (2024), and a Lorex smart security camera system (2024) providing full exterior coverage. The interior showcases recent upgrades, including a fully remodeled guest bathroom and living area (2025), alongside elegant new quartz kitchen countertops (2026). Step outside into your private backyard featuring a pristine swimming pool ideal for year-round relaxation. The outdoor area was enhanced in 2024 with premium herringbone-pattern pavers, offering a sleek, modern look and an ultra-low-maintenance alternative to a traditional lawn. Situated in a quiet, highly desirable community just minutes from Walt Disney World Resort, major Orlando attractions, world-class dining, premier shopping, and the airport, this location is unbeatable. Residents and guests also enjoy fantastic HOA amenities, including a community pool, park, playground, and basketball courts. Whether you are looking to expand your rental portfolio or find your personal piece of paradise, this property delivers the quintessential Florida lifestyle. Schedule your viewing today!

2615 Chatham Circle, Kissimmee
Kissimmee
$229,000
4 Beds ⋅ 3 Baths ⋅ Dimora Park Condo SubDv. ⋅ 34741 Zip Code
GREAT LOCATION, INCREDIBLE VALUE! 4 BEDROOMS IN A GATED COMMUNITY...! Welcome to this beautiful, modern townhouse in the desirable Dimora Park community, conveniently located in the heart of Kissimmee! Offering 4 spacious bedrooms and 2.5 bathrooms, this home combines comfort, functionality, and an excellent location. Step inside to discover a bright, open-concept kitchen-family room, perfect for everyday living and entertaining. The modern kitchen features quartz countertops, stainless steel appliances, and plenty of cabinet space. The primary bedroom is conveniently located on the FIRST FLOOR, featuring a private bathroom with dual sinks, a relaxing soaking tub, and a separate shower. The main level also includes a guest half-bathroom, a spacious laundry room, and access to a private outdoor patio. Upstairs, you'll find three additional bedrooms and a full bathroom, providing plenty of space and privacy for everyone. Enjoy the benefits of living in a gated community with a refreshing swimming pool and cabana. LOCATION, LOCATION, LOCATION! Just a 5-minute walk to Publix and conveniently located near The Loop shopping center, restaurants, schools, and everyday essentials. Easy access to John Young Parkway, Osceola Parkway, Orlando International Airport, and Central Florida's world-famous attractions, including Walt Disney World. PRICED TO SELL...! Whether you're looking for your primary residence or an investment opportunity, this property offers exceptional potential in a convenient Kissimmee location. Easy to show! Schedule your private tour today and discover everything this home has!

Kissimmee
3101 Yellow Lantana Lane, Kissimmee
$356,000
3 Beds ⋅ 3 Baths ⋅ Encantada Ph 1 SubDv. ⋅ 34747 Zip Code
Close to Disney World, Margaritaville, other Theme Parks, Highway 192 restaurant row. Lakefront Pool Townhome that is so pretty .Gated Community & Priced to Sell! Experience the perfect blend of luxury, convenience, and investment potential with this stunning lakefront townhome in the highly sought-after Encantada Resort, just minutes from world-famous theme parks, championship golf, premier shopping, and dining. Zoned for short-term rentals, this meticulously maintained 3-bedroom, 2.5-bathroom home offers 1,295 sq. ft. of beautifully updated living space with breathtaking water views. Inside, you’ll find quartz countertops, fresh interior paint, and a flawless open-concept layout, designed for comfort and style. Step outside to your private screened-in splash pool, perfect for relaxing after a day of adventure. Additional features include an exterior storage closet for added convenience. Encantada’s resort-style amenities include a clubhouse, state-of-the-art fitness center, resort pool, playground, limited bar menu, meeting room and a community fishing pier overlooking the serene lake. Whether you’re looking for a vacation rental, second home, or primary residence, this property is a rare find in one of Central Florida’s best locations. HOA includes access to the clubhouse and amenities, exterior and ground maintenance, internet and cable! Lots of bookings fo income is secured. More photos coming soon.

3101 Yellow Lantana Lane, Kissimmee
2687 Manesty Lane, Kissimmee
$649,900
5 Beds ⋅ 5 Baths ⋅ Windsor Hills Ph 3 SubDv. ⋅ 34747 Zip Code
Your Own Private Resort Retreat in the Windsor Hills Community, Just Minutes from Walt Disney World! Discover this spacious 5 Bedroom, 5 Bath Vacation Home offering comfort, entertainment and investment potential. Currently operating as a Short-Term Rental, this beautifully furnished property welcomes you with soaring ceilings, an inviting Living Room, Formal Dining Area, Fully Equipped Kitchen with Breakfast Nook and plenty of space for gathering and entertaining. Step outside to your own private tropical escape featuring a Screen-Enclosed Pool and Spa, Expansive Brick Paver Deck and Covered Patio, perfect for relaxing after a day at the parks. One of the home's standout features is the impressive Garage Conversion into a Private Home Theater and Game Room, complete with a 110" Screen, 4K Projector, Polk Soundbar, Dedicated Mini-Split A/C, Theater Seating, Arcade Gaming and Foosball Table, creating an exceptional entertainment experience! Thoughtful improvements include Remodeled Bedrooms, Updated Twin Beds, New Dishwasher and Pool Pump (2021), Pool Heater and Refrigerator (2022), Hot Water Heater and New Pool Furniture (2025). Located within this Gated Resort, owners and guests enjoy exceptional amenities including a Resort-Style Pool, Water Slides, Clubhouse, Fitness Center, Movie Theater, Game Room, Playgrounds, Sports Courts and More! With its Prime Location near Disney World, Shopping, Dining and Orlando's World-Class Attractions, this property presents an exciting opportunity for a Personal Vacation Retreat or Income-Producing Short-Term Rental Investment. Experience the Best of Florida Resort Living! Schedule Your Showing Today!

2687 Manesty Lane, Kissimmee
2394 Caravelle Cir, Kissimmee
$274,000
4 Beds ⋅ 3 Baths ⋅ Coral Cay Resort SubDv. ⋅ 34746 Zip Code
PRICED TO SELL — TURNKEY & FULLY FURNISHED IN CORAL CAY RESORT! Welcome to 2394 Caravelle Cir, a 4-bedroom, 3-bathroom townhome being sold WITH ALL FURNITURE INCLUDED — just bring your suitcase! Featuring a BRAND-NEW ROOF, an open living and dining area, a spacious kitchen, and a private screened lanai made for morning coffee and evening relaxation. The bedrooms are generously sized, including fun themed rooms the kids will love. Live the resort life every day: clubhouse, sparkling community pool, playgrounds and lush tropical landscaping — all just minutes from Disney, shopping, dining and the major highways. Perfect as a vacation home, investment property or full-time residence. Priced to move in Coral Cay — schedule your showing today before it's gone!

2394 Caravelle Cir, Kissimmee
456 Southfield Street, Kissimmee
$720,000
5 Beds ⋅ 5 Baths ⋅ Reunion West Ph 4 SubDv. ⋅ 34747 Zip Code
Stunning Fully Furnished 5-Bedroom Pool Home in Encore at Reunion Resort – Minutes from Disney! Welcome to this beautifully designed, FULLY FURNISHED 5-bedroom, 4-full-bathroom home with an additional half bathroom conveniently located by the pool. Featuring modern, stylish décor and elegant finishes throughout, this property is move-in ready and perfect as a primary residence, vacation retreat, or income-producing investment. The spacious open-concept floor plan seamlessly connects the living, dining, and kitchen areas, creating an inviting space for entertaining and family gatherings. A dedicated movie theater room adds the perfect touch of entertainment and luxury. Step outside to your private heated pool and spa, surrounded by a spacious backyard with NO REAR NEIGHBORS, providing enhanced privacy and a peaceful setting to relax, entertain, and enjoy the Florida sunshine. The home also features a garage for added convenience. Located in the highly desirable Encore at Reunion Resort, residents and guests can enjoy exceptional resort-style amenities, including a water park, on-site restaurant and bar, fitness center, tennis courts, soccer fields, and sand volleyball courts. Just minutes from Walt Disney World, Orlando's world-famous attractions, shopping destinations, and a wide variety of dining options. Whether you're looking for a beautiful place to call home, a vacation getaway for family and friends, or an investment property with rental income potential, this home offers the perfect combination of luxury, comfort, location, privacy, and resort-style living!

456 Southfield Street, Kissimmee
9239 Westside Hills Drive, Davenport
$360,000
3 Beds ⋅ 2 Baths ⋅ Bellaviva Ph 2 SubDv. ⋅ 33896 Zip Code
Built in 2024, this beautiful single-story home in the desirable community offers modern finishes, a spacious layout, and a convenient location just minutes from Disney. Featuring an open-concept floor plan, the home is filled with natural light and showcases stylish wood-look plank flooring and high ceilings throughout the main living area. The kitchen is designed for both everyday living and entertaining, featuring a large center island, 36-inch upper cabinets, elegant Silestone countertops, a premium Moen faucet, a deep sink, and stainless steel appliances. The home offers three generously sized bedrooms and two full bathrooms. Two secondary bedrooms are located toward the front of the home and share a full bathroom, while the private primary suite is tucked away at the rear, offering a spacious walk-in closet and an ensuite bathroom with dual vanities and a beautifully tiled walk-in shower. Additional features include an indoor laundry room with direct access to the two-car garage and a covered rear patio, perfect for relaxing or enjoying outdoor dining. BellaVIVA offers a convenient lifestyle with community amenities including a resort-style swimming pool, green spaces, and scenic walking trails. Located just minutes from Walt Disney World, shopping, dining, entertainment, and nearby schools, this home offers an excellent combination of comfort, modern living, and location. Schedule your private showing today!

9239 Westside Hills Drive, Davenport
3001 Greystone Loop Unit 102, Kissimmee
$219,000
3 Beds ⋅ 2 Baths ⋅ Flora Ridge Condo Ph 4 Bldg 8 SubDv. ⋅ 34741 Zip Code
Virtually Staged. Enjoy the convenience of FIRST-FLOOR CONDO LIVING in the GUARD GATED Florida Ridge community of Kissimmee! Whether you are looking for a primary residence or a home away from home near Central Florida's world-famous attractions, this condo offers a great combination of comfort, location, and LOW MAINTENANCE LIVING. A covered front entry welcomes you inside to OPEN LIVING & DINING SPACES with TILE FLOORING THROUGHOUT, making everyday living and entertaining easy. The SPLIT BEDROOM FLOOR PLAN provides added privacy, while the PRIMARY SUITE offers its own space to unwind. Step outside to the SCREENED LANAI for a little fresh air, and enjoy the convenience of IN-UNIT LAUNDRY in the laundry off the kitchen. Located just a short distance from the COMMUNITY POOL, residents have access to amenities including a fitness center, gated access with a guard, and the community pool overlooks a peaceful pond. The location puts you close to The Loop shopping and dining district, with plenty of retail, restaurants, and entertainment options nearby. Easy access to Osceola Parkway and John Young Parkway makes getting around Kissimmee and the greater Orlando area simple, while Walt Disney World, theme parks, and other popular attractions are just a short drive away. With its desirable first-floor location, community amenities, and convenient access to everything Central Florida has to offer, this Florida Ridge condo is ready to welcome you home!

3001 Greystone Loop Unit 102, Kissimmee
3891 Oakville Avenue, Kissimmee
$689,900
5 Beds ⋅ 5 Baths ⋅ Sonoma Resort At Tapestry Ph 1 SubDv. ⋅ 34741 Zip Code
Turnkey, Water-View, Investment Home at Sonoma Resort. Don’t miss this rare opportunity to own a fully furnished 5-bedroom, 5-bathroom home on an extra-large corner lot with serene water views in the highly sought-after gated community of Sonoma Resort at Tapestry.This single-level residence with an open floor plan is already operating successfully as a short-term rental and is ready for immediate income. With lots of space, a private screened-in pool, and an expansive deck with extended lanai, it’s perfectly designed for entertaining and maximizing rental potential. Inside you’ll find a bright open layout with tile flooring throughout, a large kitchen island, white cabinetry, stainless steel appliances, and stylish backsplash. Outside, the private pool and deck overlook peaceful water views—creating the ideal Florida lifestyle you are looking for. Enjoy resort-style amenities including a modern clubhouse, fitness center, and aquatic complex, all within a secure gated community with 24/7 guard service. Located about 8 miles from Disney and minutes from major attractions, restaurants, shopping and the MCO airport. Whether you’re seeking a second home residence or a proven income-producing property, this home delivers. Act now—homes like this with water views, private pool, and existing rental management don’t last long.

3891 Oakville Avenue, Kissimmee
1012 Tapestry Lane, Celebration
$2,999,000
6 Beds ⋅ 6 Baths ⋅ Celebration Area 5 SubDv. ⋅ 34747 Zip Code
There are beautiful homes, and then there are homes that are truly extraordinary. Welcome to 1012 Tapestry Lane, a modern Mediterranean estate in Celebration's coveted Artisan Park, reimagined from the studs up with over $1.2 million in renovations. Created by its owners as their own home, every wall, ceiling and floor was redone and every finish chosen without compromise. Set on approximately one-third of an acre with conservation views front and back, the home is approached by a private drive beneath an elegant porte-cochère to a six-car garage and an expansive motor court with additional parking. Inside, marble flows throughout the main level, up a staircase edged in frameless glass and brushed-gold hardware, and out to the lanai and pool deck. Six 8-foot Andersen doors, modern plantation shutters and four designer fireplaces set the tone, including a statement marble fireplace crowned by a circular gold convex mirror. Sculptural glass-and-brass lighting and Restoration Hardware gold mirrors glow like modern jewelry, with Lutron smart lighting, dimming and under-cabinet lighting all controlled from your phone. The kitchen is a culinary showpiece: a hand-built ILVE range and hood from Venice, Italy, Café Platinum Glass appliances with four ovens including a Speed Cook Advantium, Starmark cabinetry with illuminated glass uppers, quartz counters and backsplash, an island with oversized farmhouse sink, and a coffee bar with a prep sink. The powder room features an Italian Murano glass floating vanity, gold vessel sink and Murano crystal mirror. The first-floor owner's suite features a handcrafted fireplace wall concealing Laurameroni-inspired wardrobe storage with gold inlay detailing, plus two walk-in closets. The spa bath boasts a 10-foot glass wet room with dual showers, body jets and Newport Brass fixtures, and Victoria + Albert volcanic limestone sinks and freestanding tub beneath a John Richard chandelier. A first-floor office with walk-in closet and en-suite marble bath works equally well as a bedroom. Upstairs, two separate wings offer an en-suite bedroom, a second bedroom with hall bath and a turret room, plus a spacious bonus suite above the garage with its own staircase, bath and closet. All full baths are renovated with glass walk-in showers. Indoors meet outdoors on the over 600 sq ft covered lanai, with soaring ceilings, a three-sided fireplace and an outdoor kitchen overlooking a resurfaced, retiled heated pool and spa, surrounded by lush, private conservation. Residents enjoy the private Artisan Park clubhouse with resort-style pool, fitness center and on-site restaurant and bar, all within Celebration's charming downtown and trails. 1012 Tapestry Lane offers extraordinary space, craftsmanship and privacy, and a lifestyle that is distinctly Celebration. A home of this caliber, with this level of renovation, conservation surroundings and garage capacity, is a rare find, and one that deserves to be experienced in person.

1012 Tapestry Lane, Celebration
5562 Ronin Drive, St Cloud
$432,990
3 Beds ⋅ 3 Baths ⋅ Springhead Lakes 40s SubDv. ⋅ 34771 Zip Code
Under Construction. Welcome to the Aurora II! Upon entry into this stately two-story design is a den well-suited for at-home work. Down the foyer is a convenient open-concept layout which seamlessly melds the sun-drenched Great Room, modern kitchen and dining room together. A rear lanai provides relaxing outdoor space. Ideally situated on the top floor are all three bedrooms, including the tranquil owner’s suite with an adjoining bathroom and walk-in closet. Every home comes with Lennar’s Everything’s Included® promise, which includes all appliances as well as quartz countertops, and more in the price of your home. Springhead Lakes in Bridgewalk is one of the most anticipated new communities. At Bridgewalk, families can take advantage of the glorious resort-style swimming pool, extravagant clubhouse with a state-of-the-art fitness center, playground, basketball & volleyball courts along with close proximity to Lake Ajay! What are you waiting for? Call and make an appt today.

5562 Ronin Drive, St Cloud
7866 Spectrum Drive, Kissimmee
$350,000
3 Beds ⋅ 3 Baths ⋅ Spectrum At Reunion Ph 2 SubDv. ⋅ 34747 Zip Code
Welcome to Spectrum at Reunion! Built in 2024, this 3-bedroom, 2.5-bath townhome offers 1,708 square feet of living space with a contemporary two-story layout. The open-concept main level features tile flooring, high ceilings, and a spacious living and dining area that flows into the kitchen, complete with a center island, white shaker-style cabinetry, and stainless steel appliances. Sliding glass doors lead to a rear patio, providing additional space to enjoy the outdoors. Upstairs, the primary suite features a walk-in closet and private bathroom with dual sinks and a walk-in shower, while two additional bedrooms provide flexibility for guests or a home office. Additional highlights include an attached one-car garage, under-stair storage, and driveway parking. Located within the gated Spectrum at Reunion community, residents enjoy access to amenities including swimming pools, a fitness center, tennis courts, playgrounds, and recreational facilities. Conveniently situated near Interstate 4 and major roadways, the property provides access to shopping, dining, entertainment, and Central Florida's popular attractions. Whether you're looking for a primary residence, vacation getaway, or investment opportunity, this townhome offers a modern layout and access to resort-style amenities. Schedule your showing and explore the possibilities!

7866 Spectrum Drive, Kissimmee
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