Kissimmee Homes with Pool Amenities

Kissimmee Homes with Pool Amenities

Welcome to Kissimmee, a charming city located in Osceola County, Florida. Known for its proximity to world-famous theme parks like Walt Disney World, Universal Studios, and SeaWorld, Kissimmee offers a perfect blend of entertainment and relaxation for residents and visitors alike.

One of the most sought-after amenities in Kissimmee is homes with pool access. With the year-round warm weather that Florida is famous for, having a pool in your backyard is not just a luxury but a necessity. Imagine starting your day with a refreshing swim or unwinding by the pool after a long day - the possibilities are endless.

Whether you're looking for a cozy single-family home or a spacious villa, Kissimmee has a wide range of properties with pool amenities to suit every taste and budget. From modern designs to traditional architecture, you'll find a variety of options to choose from in this vibrant city.

Living in a home with pool amenities in Kissimmee is not just about enjoying the water - it's about embracing a lifestyle of comfort and luxury. So why wait? Dive into the Kissimmee real estate market and find your dream home with pool amenities today.

Newest Kissimmee Homes with Pool Amenities

4 Beds ⋅ 2 Baths ⋅ Seasons At Big Sky SubDv. ⋅ 34744 Zip Code

LAKE VIEWS & OPEN-CONCEPT LIVING! Welcome to this beautiful 4-bedroom, 2-bathroom home in the desirable St. Cloud at the Seasons at Big Sky community in Kissimmee. This inviting home features a bright, open-concept layout with a spacious kitchen, an oversized island with plenty of seating, abundant cabinetry, modern pendant lighting, and a seamless connection to the dining and living areas. Large sliding glass doors bring in plenty of natural light and showcase the beautiful lake views, creating a relaxing setting for everyday living and entertaining. Enjoy the lifestyle Seasons at Big Sky has with resort-style amenities, including a community pool, playground, sports courts, walking trails, and beautifully maintained open spaces. Conveniently located near US-192, major highways, shopping, dining, and Central Florida's world-famous attractions. Come experience the comfort, views, and convenience this home offers!

2949 Gavin Sky Drive, Kissimmee

7 Beds ⋅ 5 Baths ⋅ Emerald Island Residence Ph 05-B SubDv. ⋅ 34747 Zip Code

The search is over! Welcome to 2752 Lido Key Dr, a spacious FURNISHED 7-bedroom, 4.5-bath pool home located in the gated Emerald Island Resort, just minutes from Central Florida’s world-famous attractions. Offering 2,883 sq. ft. of heated living space, this home provides the space, flexibility, and resort-style setting ideal for a primary residence, vacation home, or short-term rental opportunity. Designed with large families and vacation groups in mind, the home features two primary suites—one upstairs and one downstairs—and sleeping accommodations for up to 16 guests. The bright, open living area features soaring ceilings and abundant natural light, while the spacious kitchen offers granite countertops, stainless steel appliances, a large island with seating, and plenty of cabinet and prep space. Step outside to your own Florida retreat featuring a screened private pool and spa with a covered lanai, perfect for relaxing, outdoor dining, and entertaining. And the fun doesn’t stop there! The garage has been converted into a theater/game room featuring a projection system, recliner seating, and game area—an added entertainment space for family and vacation guests. Emerald Island Resort offers an impressive collection of amenities including a clubhouse, fitness center, sauna, community pool and spa, tiki bar, tennis, basketball, and volleyball courts, all within a gated resort community. The home is conveniently located near Walt Disney World, shopping, dining, entertainment, and major roadways. Whether you're looking for a spacious Florida residence, your own vacation getaway, or a furnished property with short-term rental potential, 2752 Lido Key Dr offers an exceptional combination of space, amenities, and location. The property may also qualify for up to $3,000 toward closing costs when using the seller's preferred lender. Contact us for eligibility requirements and details. Hurry!!! - schedule your private showing today!

2752 Lido Key Drive, Kissimmee

3 Beds ⋅ 2 Baths ⋅ Wyndham Palms Condo Ph 1 SubDv. ⋅ 34747 Zip Code

Discover this fully furnished 3-bedroom, 2-bath condo in Windsor Palms Resort, a guard-gated community conveniently located just minutes from Walt Disney World, shopping, dining, entertainment, and major highways. Offering a comfortable and functional layout, the unit features vinyl flooring throughout the main living areas and includes all furnishings (except 3rd bedroom - twin beds were removed). The community permits both short-term and long-term rentals, providing flexibility for investors, vacation home buyers, or future full-time residents. Basic cable and internet are included in the HOA fee, while residents and guests enjoy access to a variety of resort-style amenities. The property is currently tenant-occupied with a lease through July 31, 2027; however, the tenant may be willing to negotiate an early move-out.

2301 Butterfly Palm Way Unit 203, Kissimmee

3 Beds ⋅ 3 Baths ⋅ Villas At Reunion Square SubDv. ⋅ 34747 Zip Code

**TOP-FLOOR CORNER UNIT IN REUNION RESORT!** Whether you are looking for a luxurious vacation home, a primary residence, or a short-term rental investment, this beautifully furnished 3-bedroom, 3-bath condominium offers the flexibility to fit your lifestyle. Currently used as an active short-term rental and enjoyed by the owners as a weekend getaway, this fourth-floor corner unit offers a wonderful combination of comfort, privacy, and resort-style living. Step inside to a bright and spacious open-concept floor plan featuring a fully equipped kitchen with stainless steel appliances, wood cabinetry, granite countertops, and ample storage. The kitchen opens seamlessly into the expansive Great Room, creating the perfect space for entertaining family and friends or simply relaxing after a day enjoying the resort. Large sliding glass doors fill the living area with natural light and open to an impressive private balcony that stretches across the entire width of the condominium. Enjoy your morning coffee, dine al fresco, or unwind while taking in beautiful views of the Tom Watson Signature Golf Course and watching golfers make their way down the course. Each of the three bedrooms features its own private ensuite bathroom and generous closet space, providing comfort and privacy for owners and guests alike. The spacious primary suite includes two walk-in closets, a luxurious ensuite bath with both a soaking tub and separate shower, and its own sliding glass doors providing direct access to the balcony. Reunion Resort offers an exceptional vacation lifestyle with 24-hour gated security, multiple resort-style pools, restaurants, fitness facilities, and an array of amenities for owners and guests to enjoy. Conveniently located near Walt Disney World and Central Florida's world-class theme parks, attractions, dining, and entertainment, this property offers both an incredible personal getaway and an attractive rental opportunity. Come experience all that Reunion Resort has to offer and discover why this top-floor corner condominium could be the perfect fit for your Central Florida lifestyle!

1100 Sunset View Cir Unit 402, Reunion

2 Beds ⋅ 2 Baths ⋅ Bvl Unit 1 SubDv. ⋅ 34743 Zip Code

HANDYMAN SPECIAL! LOW HOA AND NOT A CONDO! Immediately available 2-bedroom, 2-bath home featuring an updated roof installed in 2022 and a rear screened porch. This property offers an excellent opportunity for an investor looking for a rental or an owner-occupant seeking a home they can personalize and improve. With a low HOA and plenty of potential, this one is ready for your vision!

99 Lake Villa Way, Kissimmee

4 Beds ⋅ 2 Baths ⋅ Poinciana Village 1 Nbhd 1 North SubDv. ⋅ 34758 Zip Code

4/2/2 block home. Needs full renovation but has great bones. handyman/investor special priced accordingly.

303 Cortez Court, Kissimmee

3 Beds ⋅ 2 Baths ⋅ Flora Ridge Condo Ph 1 Bldg 1 SubDv. ⋅ 34741 Zip Code

Desirable location in the Kissimmee area. Investors are welcome! This beautiful, well-kept 3-bedroom, 2-bath condo has a bonus room directly connected to the master bedroom; The exterior was recently renovated. The spacious kitchen is equipped with all the proper appliances. This cozy condo in a gated community is strategically located near major access roads such as John Young Pky, Osceola Trnpk, US 192, and major park attractions like Disney World, SeaWorld, and Universal Studios. This property offers exceptional convenience due to its closeness to the famous Loop Shopping Center. This jewel is located just 15 -20 minutes from Disney World, 20-25 minutes from Universal Studios, and Orlando International Airport. The property includes elevators and covered parking, plus additional parking spaces are available. Hurry! Don't delay and take advantage of this low price. The seller is contributing to some closing costs.

3351 Whitestone Circle Unit 204, Kissimmee

7 Beds ⋅ 10 Baths ⋅ Reunion West Fairways 17 & 18 SubDv. ⋅ 34747 Zip Code

Exceptional luxury, privacy, and rental appeal await in Reunion Resort’s prestigious Bear’s Den Club. Set on a rare oversized homesite with no rear neighbors and a private park directly behind the property, this fully furnished seven-bedroom residence offers one of the most desirable settings in the community. Professionally designed for unforgettable guest experiences, the home features immersive custom-themed bedrooms, multiple king suites, two creative bunk rooms, a state-of-the-art home theater, a spacious loft with billiards, and a dedicated arcade. The open-concept living area flows seamlessly outdoors to a private pool and spa, covered dining area, and fully equipped summer kitchen—perfect for entertaining and enjoying the Florida sunshine. Located just minutes from Walt Disney World and Orlando’s premier attractions, Bear’s Den offers access to Reunion Resort’s world-class golf courses, dining, tennis, water park, fitness center, and concierge services. An active Reunion Club membership is available, providing immediate access to the resort’s extensive amenities. Whether you’re looking for a luxury vacation retreat or a standout investment property designed to accommodate large groups, this home delivers an exceptional combination of location, entertainment, privacy, and resort living. Be sure to view the video tour!

1063 Jack Nicklaus Court, Kissimmee

4 Beds ⋅ 3 Baths ⋅ Preserve At Tapestry Ph 3 & 4 SubDv. ⋅ 34741 Zip Code

Welcome to 2815 Monticello Way—where comfortable living, entertaining space, and a convenient Kissimmee location come together! This 4-bedroom, 2.5-bath two-story home in the Preserve at Tapestry offers 2,328 square feet of living space, a two-car garage, and a large backyard designed for enjoying the outdoors. (*Listing includes some labeled virtually staged photographs.) Inside, the main level is made for gathering. The great room creates an easy flow between the spacious kitchen, large center island, dining area, and living room—giving everyone room to spread out while staying connected. Laminate flooring runs throughout the lower level, creating a clean and practical foundation for everyday living. Upstairs, the private primary suite offers a comfortable retreat with its own ensuite bath, while three additional bedrooms and a guest bath provide flexibility for family, guests, an office, or hobbies. Step outside and the living space continues! The large backyard features a screened porch, patio area, and garden space, creating multiple spots to relax, entertain, enjoy your morning coffee, or simply unwind at the end of the day. The generous yard also provides plenty of room to enjoy the outdoors and make the space your own. Recent updates include: Dishwasher — approximately 6 months old Range — approximately 1.5 years old Washing machine — approximately 1.5 years old Dryer — approximately 3 years old Life in Preserve at Tapestry includes access to community amenities such as a resort-style pool, clubhouse, playground, and trails, all included with the monthly HOA. Scenic ponds, tree-lined streets, and established landscaping contribute to the neighborhood's inviting setting. And then there’s the location! The Loop, shopping and dining along US-192 are just minutes away, while nearby Osceola Parkway provides convenient access toward Walt Disney World, Lake Nona, the Florida Turnpike, and SR 417. Orlando International Airport and Kissimmee Gateway Airport, Disney Springs, the major theme park corridor, Lake Tohopekaliga, and historic Downtown Kissimmee are also within easy reach. Come see 2815 Monticello Way and discover a home that offers space to gather, room to relax, and a Central Florida location that keeps you close to it all!

2815 Monticello Way, Kissimmee

4 Beds ⋅ 3 Baths ⋅ Westview 50s Gc SubDv. ⋅ 34758 Zip Code

Under Construction. This new single-story McCartney Next Gen® home features a private suite with its own entrance, living area, kitchenette, bedroom, bathroom and laundry, perfect for multigenerational households. The main home is host to an inviting open-concept layout with easy access to a covered patio for seamless indoor-outdoor living. Two secondary bedrooms are located off the foyer, and a lavish owner’s suite is tucked into a private rear corner, complete with a full bathroom and walk-in closet. Westview is a master-planned community in Poinciana, FL. This amenity-rich, pet-friendly community has something for residents of all ages to enjoy, including a swimming pool, dog park, clubhouse and sports fields. Lake Marion Creek Wildlife Management Area is nearby with hiking trails, as well as Poinciana for shopping, dining and entertainment options. The community is in close proximity to Highway 17 for easy commuting to Greater Orlando.

5595 Dennery Bay Road, Kissimmee

3 Beds ⋅ 3 Baths ⋅ Regal Oaks At Old Town SubDv. ⋅ 34746 Zip Code

Escape to one of the most desirable resort community with this beautifully maintained 3-bedroom, 2.5-bath townhome, and a private screened lanai with jacuzzi, creating the perfect setting to relax after a day of enjoying Central Florida's world-famous attractions. Step inside to discover a bright, open-concept floor plan designed for comfort and entertaining. The spacious kitchen flows seamlessly into the living and dining areas, while large windows invite natural light. Upstairs, the primary suite serves as a private retreat with balcony, featuring an en-suite bath with a generous walk-in shower. Whether you're seeking a vacation home, short-term rental investment, or full-time residence, this property offers the flexibility for the want of today's buyers. Located within the gated Regal Oaks Resort, owners and guests enjoy exceptional amenities including a resort-style pool with exciting water slides, clubhouse, restaurant, fitness center, tennis courts, and more. Imagine starting your mornings with peaceful setting and ending your evenings soaking in your private jacuzzi under the screened lanai. All of this just minutes from Disney, premier shopping, dining, and entertainment. Highlights: Tile roof... Private screened lanai with jacuzzi spa... Corner unit... 3 Bedrooms 2.5 Bathrooms... Open concept living and entertaining spaces... Inside laundry... Gated and guarded resort community with top-tier amenities... Ideal as a vacation home, investment property, or primary residence... Minutes from Disney, dining, shopping, and attractions. Don't miss your opportunity to own the community's best-valued townhome.

2715 Coupe Street, Kissimmee

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.*

1872 Southbury Drive, Kissimmee

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