Osceola County Homes with Pool Community Features

Osceola County Homes with Pool Community Features

Osceola County, located in Florida, offers a wonderful mix of suburban living and natural beauty. With a Homes with Pool Community Features designation, residents can enjoy the luxury of having a pool right at their doorstep. This feature not only adds value to the property but also provides a perfect setting for relaxation and entertainment.

Osceola County boasts a diverse real estate market, with properties ranging from cozy single-family homes to spacious estates. The Homes with Pool Community Features option is particularly appealing for those seeking a resort-style living experience without leaving the comfort of their neighborhood.

Living in a community with pool amenities allows residents to stay active, socialize with neighbors, and create lasting memories with family and friends. Whether you're looking for a primary residence or a vacation home, Osceola County's Homes with Pool Community Features provide an attractive option for those who value both comfort and convenience in their living environment.

Newest Osceola County Homes with Pool Community Features

4511 Monado Drive, Kissimmee
$569,990
5 Beds ⋅ 6 Baths ⋅ Bellavida Ph 2a SubDv. ⋅ 34746 Zip Code
PRIVATE POOL, FIVE ENSUITE BEDROOMS, AND A RESORT LOCATION NEAR CENTRAL FLORIDA’S TOP ATTRACTIONS! Welcome to 4511 Monado Drive in guard-gated Bella Vida Resort, where spacious living and vacation-home potential come together. Built in 2015, this 5-bedroom, 5-bathroom home offers approximately 3,042 square feet of living space, a two-car garage, and an inviting layout suited to entertaining and accommodating guests. The open-concept living and dining areas create a comfortable gathering space, while the kitchen features granite countertops, ample cabinetry, and room to prepare meals between outings. Each bedroom features an ensuite bathroom, providing privacy and convenience—a valuable feature for vacationing groups sharing a home. A spacious game room offers the opportunity to create an entertainment area that enhances the vacation experience. Step outside to the PRIVATE SCREENED-IN POOL IN THE BACK OF THE HOME! This inviting outdoor retreat provides space for refreshing swims, poolside relaxation, and making the most of Florida’s sunshine. The lanai and surrounding deck offer room to create outdoor dining and lounge areas, giving owners and guests a welcoming place to unwind after a day at the parks. LOCATION IS A KEY PART OF THE APPEAL. Enjoy access to Walt Disney World Resort, Disney Springs, SeaWorld Orlando, and Universal Orlando Resort, along with the dining and entertainment options throughout the surrounding tourist corridor. Nearby outings include Medieval Times Dinner & Tournament and Old Town Kissimmee, adding variety beyond the major theme parks. Shopping destinations within the surrounding area include The LOOP and LOOP West, Lake Buena Vista Factory Stores, and Orlando Vineland Premium Outlets. Restaurants, grocery stores, and everyday conveniences along US-192 make it easy to stock the kitchen, dine out, and plan a comfortable extended stay. For buyers exploring short-term rental opportunities, the combination of five ensuite bedrooms, a private backyard pool, recreation space, and resort amenities provides compelling features to showcase in a future vacation rental listing. The layout accommodates shared gatherings while offering separate spaces for privacy, and the location gives visitors access to theme parks, shopping, dining, and entertainment throughout their stay. Offered UNFURNISHED, this property gives the next owner the freedom to develop a distinctive design and furnishing package. Create themed bedrooms, a coordinated interior, and an inviting game room tailored to your vision for a personal retreat or vacation rental. Bella Vida Resort complements the home with guard-gated entry, a clubhouse, community pool and spa, fitness center, and recreation amenities. Discover the possibilities of owning a spacious pool home in an established Kissimmee vacation-home community. Schedule your private showing today! Buyer to verify rental eligibility, licensing requirements, occupancy limits, HOA restrictions, fees, and amenity access.

4511 Monado Drive, Kissimmee
801 Oak Shadows Road, Celebration
$2,495,000
6 Beds ⋅ 5 Baths ⋅ Celebration East Village Unit 3 SubDv. ⋅ 34747 Zip Code
Tucked on a quiet, tree-lined street in Celebration's sought after East Village, this single-story 6 bedrooms estate greets you with a wrap-around porch of red Chicago brick, made for slow afternoons, and a screened side porch off the dining room for dinner al fresco. Set on an oversized homesite of nearly half an acre, it offers a sense of space and privacy that is hard to find in Celebration. Double doors open to formal dining, a living room or office, and a formal living room overlooking the screened patio and pool. High ceilings and crown molding throughout. The upgraded kitchen flows into a breakfast nook wrapped in glass and a family room. The owner's suite opens to the patio, with plantation shutters, two large closets, a soaking tub, separate vanities and a sauna in the shower. Two bedrooms share a Jack and Jill bath, and a third bedroom or office connects to a pool bath. A large laundry room and two flex rooms complete the home. Step outside and the home becomes a private resort. The screened patio opens to a sparkling pool and spa framed by lush, mature landscaping, with palms and tropical greenery creating a natural sense of seclusion. Beyond the pool, a sprawling backyard unfolds, with citrus trees and room to garden, play or entertain, all backing to conservation woods. A porte-cochère and long driveway lead to a six-car garage with a 2-bed, 2-bath guest house above, with a full kitchen and a private deck over conservation woods. A six-car garage is almost unheard of in Celebration, with room for a car collection, a workshop, golf carts and more. Paid-off solar adds lasting savings. Living in East Village means morning walks on tree-shaded sidewalks, evenings by golf cart to the lakefront shops and restaurants of downtown Celebration, and a community of parks, trails and front porches, just minutes from Disney and the best of Central Florida. Schedule your private showing today.

801 Oak Shadows Road, Celebration
1435 Pro Shop Court, Davenport
$389,900
3 Beds ⋅ 2 Baths ⋅ Stoneybrook South Ph F-1 SubDv. ⋅ 33896 Zip Code
Welcome to luxury golf-community living in the highly desirable gated enclave of ChampionsGate Country Club! Situated on an oversized lot directly across from hole sixteen, this home features three bedrooms, two full bathrooms, a two-car garage, and light-filled, open-concept living space with high-end custom finishes. The completely carpet-free interior boasts elegant tile flooring throughout the main living areas and newly updated laminate flooring in all bedrooms. Step outside to your private east-facing screened back patio, highlighted by beautiful brick pavers and equipped with a brand-new dedicated air conditioning unit for comfortable, climate-controlled year-round outdoor entertaining. Enjoy top-tier resort-style HOA amenities, including golf access, tennis courts, a splash park and lazy river pool, a state-of-the-art fitness center, clubhouse, and full lawn maintenance. Perfectly situated with convenient access to Interstate four and Highway twenty-seven, you are minutes from ChampionsGate Village dining and about ten minutes from Posner Park for shopping, restaurants, and IMAX theater entertainment. Theme park enthusiasts will appreciate being approximately fifteen minutes from Walt Disney World Resort and within easy reach of Universal Studios and SeaWorld. Outdoor enthusiasts can take advantage of nearby paved walking trails at Northeast Regional Park, hiking and kayaking at Lake Louisa State Park, world-class fishing at Lake Tohopekaliga, or day trips to Florida coast beaches. Top educational options abound, with public school zoning for Osceola County Schools alongside highly regarded charter alternatives right in the community including BridgePrep Academy of ChampionsGate, Four Corners Charter School, and Osceola Science Charter School.

1435 Pro Shop Court, Davenport
911 Dartmouth Court, Kissimmee
$259,900
3 Beds ⋅ 2 Baths ⋅ Poinciana Village 2 Nbhd 1 SubDv. ⋅ 34758 Zip Code
BEAUTIFULLY REFRESHED, MOVE-IN READY KISSIMMEE HOME WITH STYLISH UPGRADES AND INVITING LIVING SPACES! Welcome home to this beautifully refreshed 3-bedroom, 2-bathroom, 1,329-square-foot gem nestled in the desirable Poinciana Villages community! Thoughtfully updated and staged to perfection, this charming residence offers the perfect blend of modern finishes, comfortable living, and everyday functionality. From the moment you step inside, you'll appreciate the fresh interior paint, gorgeous new luxury vinyl plank flooring throughout, and an abundance of natural light that creates a warm and welcoming atmosphere. The inviting foyer opens to two generously sized bedrooms on the right, while straight ahead, the spacious living and dining areas provide the perfect setting for gathering with family and friends. The beautifully updated kitchen is sure to impress! Featuring stunning granite countertops, ample cabinetry, a convenient breakfast bar, and an additional eat-in dining space, this kitchen offers both beauty and practicality with plenty of room to cook, entertain, and make lasting memories. Both bathrooms have been tastefully refreshed with stylish new vanities, fixtures, and faucets, adding a modern touch throughout the home. Privately situated off the main living area, the spacious primary suite offers a peaceful retreat complete with a gorgeously updated ensuite bathroom designed with comfort and style in mind. Every room has been thoughtfully refreshed, creating a cohesive, move-in-ready home that feels as inviting as it looks! STEP OUTSIDE AND ENJOY THE BEST OF FLORIDA LIVING! Sliding glass doors lead to a spacious screened-in patio overlooking the large, fenced backyard, offering the perfect backdrop for morning coffee, weekend barbecues, outdoor dining, or simply relaxing and enjoying the beautiful Florida weather. With plenty of room for entertaining, pets, and outdoor activities, this backyard is ready for you to make it your own! Residents of Poinciana Villages enjoy access to an impressive variety of community amenities, including a swimming pool, fitness center, playgrounds, basketball courts, pickleball and racquetball courts, tennis courts, and 11 neighborhood parks! Conveniently located near shopping, dining, schools, Disney Wilderness Preserve, Shingle Creek Regional Park, and Kissimmee Lakefront Park, with access to Central Florida's major roadways and world-famous attractions, this location offers both convenience and recreation. BEAUTIFULLY UPDATED, METICULOUSLY MAINTAINED, AND READY TO WELCOME YOU HOME! Whether you're purchasing your first home, looking for a comfortable place to settle down, or seeking your next investment opportunity, this Kissimmee beauty checks all the boxes. Schedule your private showing today and discover everything this wonderful home has to offer!

911 Dartmouth Court, Kissimmee
8513 Bay Lilly Loop, Kissimmee
$380,000
4 Beds ⋅ 3 Baths ⋅ Encantada Ph 1 SubDv. ⋅ 34747 Zip Code
Attention Investors! This beautiful FULLY FURNISHED 4-bedroom 3-bathroom Townhouse with private heated pool could be yours. This home comes not just fully furnished, but equipped with appliances, dishes, flatware, bowls, coffee makers (including Keurig), blender, popcorn machine, sheets, towels, washcloths, pillows, everything you will need for a fully operational short-term rental, turnkey. The four bedrooms are all furnished with beds, nightstands, lamps, dressers, flat screen televisions, ready for you and your family or your guests. Encantada is a short-term rental community with a fully functioning award-winning clubhouse, with a gym/fitness center, game room, restaurant/cafe, sundry shop, two community pools, two hot tubs/spa, and a very peaceful and delightful fishing pier. Upon entering you will notice the bright open space. When opening the sliding patio doors to your private pool and patio, you'll be in awe. The 4-burner grill is included in the sale of this property. This space is great for entertainment and relaxation. HOA fees include 24-hour manned security, landscaping, high-speed Internet, cable, private telephone with a local number and free calls within the U.S. and of course outside maintenance and repairs. ENCANTADA, is located off of US 192, and minutes from Disney World, restaurants, shopping plazas with the most popular and convenient stores. A/C is only 18 months old; Pool includes a smart heater than can be accessed using a phone app. The property is equipped with an electronic smart lock with key. Whether you want to occupy it or use it as a short-term rental vacation home This townhome has a lot to offer at an exceptional value. A Must See!

8513 Bay Lilly Loop, Kissimmee
3180 Paradox Circle Unit 106, Kissimmee
$300,000
2 Beds ⋅ 2 Baths ⋅ The Terraces At Storey Lake Condo No 2 Ph 13 Or 57 SubDv. ⋅ 34746 Zip Code
Storey Lake t is a premier, master-planned gated vacation community located in Kissimmee, Florida. This highly sought-after property is zoned for short-term rentals and long-term rentals, making it one of the top choices for real estate investors and vacation home buyers in the Greater Orlando area. Combining luxury resort amenities with an unbeatable location just minutes from Walt Disney World, it offers an exceptional blend of personal holiday enjoyment and lucrative investment potential. Five key benefits for owners are: prime location, proven rental income potential, world-class resort amenities, and low-maintenance ownership.

3180 Paradox Circle Unit 106, Kissimmee
1771 Sawyer Palm Place, Kissimmee
$549,000
6 Beds ⋅ 5 Baths ⋅ Solara Resort SubDv. ⋅ 34747 Zip Code
Experience the ultimate blend of comfort, entertainment, and turnkey convenience at 1771 Sawyer Palm Pl, an expansive 6-bedroom, 4.5-bathroom fully furnished home nestled in the premier, gated community of Solara Resort. Designed to impress vacation-home seekers and savvy short-term rental investors alike, the property boasts a light-filled, open-concept floor plan built for seamless gathering. Step outside to your private oasis featuring a screened-in lanai, private pool with an extended deck, and spa, ideal for unwinding under the warm Florida sunshine. Inside, continuous entertainment awaits in the converted garage game room, offering endless fun for guests and family members of all ages. Beyond the front door, Solara Resort delivers a world-class lifestyle with an exceptional Grand Clubhouse, zero-entry lagoon pool, FlowRider® surf simulator, kids’ splash pad, and private poolside cabanas. Residents and guests enjoy an on-site bar and grill, a modern fitness center, beach volleyball, basketball courts, and a full-size soccer field. Located just minutes from Central Florida’s world-renowned theme parks, premier golf courses, the Promenade at Sunset Walk, and an array of shopping and dining corridors, this residence offers an effortless, high-performing asset or an unforgettable family retreat.

1771 Sawyer Palm Place, Kissimmee
4714 Hemingway House Street, Kissimmee
$259,000
3 Beds ⋅ 3 Baths ⋅ Fiesta Key SubDv. ⋅ 34746 Zip Code
FULLY FURNISHED & MOVE-IN READY! SHORT-TERM RENTALS ALLOWED! Welcome to this beautiful 3-bedroom, 2.5-bathroom townhome located in the gated, resort-style community of Fiesta Key, just minutes from Walt Disney World and Celebration! Whether you're searching for a primary residence, vacation home, or investment opportunity, this property offers the perfect combination of comfort, convenience, and flexibility. All furniture and furnishings are included in the sale, making this home truly move-in ready! The interior features an upgraded kitchen with quartz countertops, ceramic tile flooring throughout the first floor, and luxury vinyl plank flooring upstairs. Enjoy the added benefit of NO CARPET throughout the entire home! The spacious primary suite features a double-sink vanity, offering both comfort and functionality. Residents and guests can enjoy an impressive selection of resort-style amenities, including a clubhouse, fitness center, community pool, playground, tennis courts, and gated security. Conveniently located near shopping, restaurants, entertainment, and Central Florida's world-famous attractions, this property is an excellent opportunity for homeowners, vacationers, and investors alike. Don't miss your chance to own a fully furnished townhome in one of Kissimmee's short-term rental-friendly communities. Schedule your private showing today!

4714 Hemingway House Street, Kissimmee
8809 Dunes Court Unit 303, Kissimmee
$229,900
3 Beds ⋅ 2 Baths ⋅ Legacy Dunes Condo SubDv. ⋅ 34747 Zip Code
Expect To Be Impressed With This Pristine Maintained And Fully Furnished 3 Bedroom, 2 Bath Condo. Ideally Located With Just A Short Walking Distance To Clubhouse And Amenities. This Top Floor Condo Eliminates Any Noises Above Unit, Offers Open Living Areas With Built In Shelving, Split Bedroom Plan, Walk In Closets, Inside Laundry Room, Ceiling Fans, Screen Enclosed Lanai And Much More ! This Privacy Gated Community Provides An Array Of Resort Style Amenities Which Include A Club House, Two Pools, Fitness Center, Game Room, Lighted Tennis, Basketball, And Pickleball Courts, Sand Volley Ball Court, Playground, Walking Trails, BBQ Grills, And Golf Driving Net. All Of This Plus Being Located Just Minutes From Walt Disney World And The Other Major Tourist Attractions, Shopping, Restaurants, Main Highways/Expressways. Fantastic Opportunity To Own Full Time Or As A Vacation Property.

8809 Dunes Court Unit 303, Kissimmee
1916 Southbury Drive, Kissimmee
$494,790
5 Beds ⋅ 3 Baths ⋅ Kindred SubDv. ⋅ 34744 Zip Code
Inside this beautiful 5-bedroom, 3-bathroom home, you'll find 2,077 square feet of comfortable living. The living area is an open concept, where your kitchen, living, and dining areas blend seamlessly into a space perfect for everyday living and entertaining. The kitchen features modern cabinets, quartz countertops, and sleek stainless-steel appliances. You'll never be too far from the action with the living and dining area right there. Find RevWood Select Flooring throughout a majority of the home including the family room, primary bedroom, kitchen, bathrooms, laundry and foyer. The primary bedroom has its own attached bathroom that features a walk-in closet and all the space you need to get ready in the morning. Privacy is guaranteed with a separate door for the toilet and shower. *Photos are of similar model but not that of exact house. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built. Home and community information including pricing, included features, terms, availability and amenities are subject to change and prior sale at any time without notice or obligation. Please note that no representations or warranties are made regarding school districts or school assignments; you should conduct your own investigation regarding current and future schools and school boundaries.*

1916 Southbury Drive, Kissimmee
1617 Mohegan Boulevard, Kissimmee
$310,800
3 Beds ⋅ 3 Baths ⋅ Heritage Run SubDv. ⋅ 34744 Zip Code
Short Sale. Located in the gated community of Heritage Run this townhome offers 3 bedrooms, 2.5 bathrooms, and a functional open layout. Features include: 9-foot ceilings, a spacious kitchen with 42-inch solid wood cabinetry, granite countertops, stainless steel appliances, and a large island, family and dining room combo, convenient laundry room upstairs, large master suite with dual sinks, state of the art shower and large walk-in-closet. Close to Kissimmee, shopping, dining, and everyday amenities. Osceola Heritage Park is within walking distance, while The Loop, downtown Kissimmee, and Orlando International Airport are just minutes away. With easy access to the Florida Turnpike, this property is ideal for homeowners, investors, or anyone looking for low-maintenance living. There is a $10,000 dollar buyers premium due at closing.

1617 Mohegan Boulevard, Kissimmee
1920 Southbury Drive, Kissimmee
$501,490
5 Beds ⋅ 3 Baths ⋅ Kindred SubDv. ⋅ 34744 Zip Code
Under Construction. Kindred presents the Hayden. This amazing all concrete block construction single-family home features 5 bedrooms and 3 bathrooms optimizing living space with an open concept layout. The kitchen overlooks the dining area and great room, while having a view to the covered lanai outside. Ample windows and a set of sliding glass doors allow lighting into the living area. The well-appointed kitchen features an island with bar seating, beautiful quartz countertops and stainless-steel appliances, making entertaining a breeze. The first floor also features a flex room that provides an area for work or play, a bedroom, and full bathroom. As we head up to the second floor, we are greeted with bedroom one that features an en suite bathroom as well as three additional bedrooms that surround a second living area, a full bathroom, and a laundry area. Like all homes in Kindred, the Hayden includes Smart home technology package which allows you to control your home with your smart device while near or away. *Photos are of similar model but not that of exact house. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built. Home and community information including pricing, included features, terms, availability and amenities are subject to change and prior sale at any time without notice or obligation. Please note that no representations or warranties are made regarding school districts or school assignments; you should conduct your own investigation regarding current and future schools and school boundaries.*

1920 Southbury Drive, Kissimmee
Start Your Search

How much is your home worth?

Get instant property value now!