Kissimmee Homes with Pool

Kissimmee Homes with Pool

Welcome to Kissimmee, a vibrant 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.

Imagine coming home to your very own piece of paradise in Kissimmee - a beautiful house with a pool where you can unwind and soak up the Florida sunshine. Homes with pools in Kissimmee are not just a luxury but a way of life, offering residents a refreshing retreat right in their backyard.

Whether you're looking for a cozy single-family home or a spacious estate, Kissimmee has a diverse range of properties with pools to suit every lifestyle. From entertaining guests to enjoying a peaceful morning swim, owning a home with a pool in Kissimmee adds an element of luxury to your everyday life.

As you explore real estate options in Kissimmee, consider the added value and enjoyment that a pool can bring to your home. It's not just a feature; it's a lifestyle upgrade that enhances your property and creates unforgettable memories with family and friends.

Discover the allure of Kissimmee living and find your dream home with a pool in this enchanting city in the heart of Florida. Experience the best of both worlds - the excitement of theme parks and the tranquility of your own private oasis. Welcome home to Kissimmee, where every day feels like a vacation.

Newest Kissimmee Homes with Pool

4 Beds ⋅ 3 Baths ⋅ O6434358 MLS ⋅ 4006 BLDG.

OWN THIS beautifully updated and fully furnished end-unit townhouse in the 24-hour guard-gated community of Venetian Bay Village. Offering 4 bedrooms, 3 bathrooms, and a flexible two-story layout, this property is ideal as a vacation home, full-time residence, or income-producing investment. Recent 2025 upgrades include new flooring, a new water heater, quartz countertops throughout, and renovated bathrooms, giving the home a fresh and move-in-ready feel. The main level features an open living and dining area, a well-appointed kitchen, and a highly desirable first-floor primary suite with an en-suite bathroom and walk-in closet. Upstairs, a second primary suite provides extra flexibility for guests and family, while two additional bedrooms offer comfortable accommodations for family or visitors. Enjoy the charm of a covered front porch and side porch, along with access to resort-style amenities including community pool, clubhouse, fitness center, playground, tennis courts, and 24-hour security. Located just minutes from Disney, shopping, dining, major roadways, and Central Florida’s top attractions, this turnkey property offers comfort, convenience, and strong rental potential in one of Kissimmee’s established vacation communities. Schedule your showing today!

4006 San Gallo Drive Unit 108, Kissimmee

2 Beds ⋅ 2 Baths ⋅ O6434484 MLS ⋅ 2212 BLDG.

LOCATION, LIFESTYLE & FLEXIBILITY—PLUS A RARE BONUS FLEX SPACE! Welcome to a spacious 2-bedroom, 2-bath condominium in the gated, resort-style community of Villas del Sol at Kissimmee. What truly sets this unit apart is the additional dedicated office/flex room, a valuable and hard-to-find feature within the community—ideal for a home office, study, hobby room, media space or additional flexible living area. Inside, the bright and open floor plan offers comfortable living and dining spaces, a functional kitchen, generously sized bedrooms and tile flooring throughout the main living areas. The versatile bonus room adds functionality rarely found in the traditional 2-bedroom layouts within Villas del Sol. Enjoy the Florida lifestyle without leaving the community! Villas del Sol offers an impressive collection of resort-style amenities, including two swimming pools, clubhouse, fitness center, tennis courts, playground and beautifully maintained common areas, all within a gated setting. The location is another standout. Situated in the heart of Kissimmee with convenient access to US-192, John Young Parkway, Osceola Parkway and Florida's Turnpike, this property places shopping, dining and entertainment within easy reach. The Loop shopping and entertainment district, Walt Disney World Resort and Central Florida's world-renowned attractions are all conveniently accessible, while Orlando and surrounding employment and entertainment destinations are just a drive away. Whether you're searching for a primary residence, Florida snowbird retreat, vacation-area home or investment property, this condo offers an attractive combination of location, amenities and versatility. Seller is offering a contribution toward an interest rate buy-down when buyer uses preferred lender, subject to buyer qualification, lender approval and applicable loan/program guidelines. Ask for details. INVESTORS TAKE NOTE:The property is currently tenant-occupied through November 14, 2026, providing the opportunity to acquire an already-leased property while planning for its future use. With 2 bedrooms, 2 full bathrooms PLUS the rare additional office/flex space, resort-style community amenities and a central Kissimmee location near shopping, dining, major roadways and Orlando's attractions, this Villas del Sol condo offers something truly different. Schedule your private showing and discover the possibilities!

2212 Grand Cayman Court Unit 1617, Kissimmee

4 Beds ⋅ 3 Baths ⋅ O6431031 MLS ⋅ 4833 BLDG.

Turnkey furnished vacation home in the sought-after Storey Lake resort community, ideally located just minutes from Central Florida’s world-famous attractions. Approximately 6 miles to Walt Disney World Resort, 11 miles to Universal Orlando Resort, 7 miles to SeaWorld Orlando, and just a few miles to Disney Springs, this 4-bedroom, 3-bathroom home offers a location and layout well suited for short-term rental use, a vacation home, or a primary residence. The open-concept first floor features a spacious kitchen with 42-inch cabinets, stainless steel appliances, quartz countertops, and a large island with breakfast bar overlooking the dining and living areas. A first-floor bedroom and full bathroom with walk-in shower provide added flexibility for guests and multigenerational stays. Upstairs, the primary suite offers a walk-in closet and ensuite bathroom with dual sinks and a shower/tub combination. Two additional bedrooms share a full bathroom with dual sinks and a walk-in shower, with an upstairs laundry closet for added convenience. The covered patio and private screened-in pool overlook peaceful water views, creating a private outdoor retreat for guests after a day at the area's theme parks and attractions. Storey Lake offers an extensive selection of resort amenities, including two clubhouses, two lazy rivers, resort pools, water slides, splash pad, mini-golf, fitness centers, tennis, basketball, volleyball, playgrounds, scenic walking trails, canoe and kayak rentals, community dock, tiki bars and restaurants, private beach, dog parks, and shuttle service. The community is also conveniently located near shopping, dining, golf, entertainment, outlet malls, and Orlando International Airport. The HOA includes garage service, cable, internet, exterior maintenance, landscaping, and gated security. Fully furnished and positioned in one of Central Florida’s most popular vacation destinations, 4833 Romeo Circle offers the flexibility and amenities sought by today’s vacation rental market while also providing an ideal place to enjoy Central Florida yourself.

4833 Romeo Circle, Kissimmee

5 Beds ⋅ 4 Baths ⋅ O6433022 MLS

WELL-BOOKED SHORT TERM RENTAL PROPERTY! This TURNKEY, FULLY FURNISHED 5-bedroom, 4-bath pool home is a high-performing short-term rental located in the sought-after NO HOA / NO CDD community of Indian Creek. Professionally decorated and designed for guest appeal, the home features a flexible, semi-open floor plan with durable tile flooring throughout and modern finishes—ideal for low-maintenance ownership. The layout is perfectly suited for rental success, offering multiple bedroom suites and excellent privacy. A front guest bedroom and adjacent full bath provide convenience for early arrivals, while two additional bedrooms share a full bath on one wing of the home. A private en-suite bedroom with direct pool access adds strong guest appeal, and the spacious primary suite—separate from other bedrooms—features dual vanities, a soaking tub, glass-enclosed shower, two walk-in closets, and private access to the pool. The kitchen is fully equipped with modern cabinetry, granite countertops, stainless steel appliances, a breakfast bar, and dinette, flowing seamlessly into the dining and main living areas filled with natural light—perfect for hosting larger groups. Sliding doors open to a screened-in pool and lanai, set within a fully fenced backyard, creating a resort-style outdoor space guests love. Located just minutes from Disney and major theme parks, shopping, dining, and entertainment, this home benefits from consistent demand and easy access to major roadways. With no rental restrictions, no HOA fees, and no CDD, this property is an exceptional opportunity for investors seeking a ready-to-go Airbnb or short-term rental with STRONG INCOME POTENTIAL in the heart of Central Florida. ROOF 2019, A/C 2016. **This house comes with a REDUCED RATE through the seller's preferred lender. This is a lender-paid rate buydown that reduces the buyer's interest rate and monthly payment.**

8060 Santee Drive, Kissimmee

4 Beds ⋅ 3 Baths ⋅ O6432614 MLS

Welcome to this inviting 4-bedroom, 3-bathroom pool home located in the gated resort-style community of Windsor Palms. Offering 1,835 square feet of heated living space, this well-designed single-story residence features an open floor plan, a desirable split-bedroom layout, high ceilings, and an abundance of natural light. The spacious kitchen is equipped with granite countertops, ample cabinetry, a center island with breakfast-bar seating, and a casual dining area overlooking the pool. The kitchen flows seamlessly into the family room, creating a comfortable and functional space for everyday living and entertaining. A separate dining area provides additional room for gatherings. The primary suite offers privacy and features an en-suite bathroom with a garden tub and separate shower. Three additional bedrooms provide plenty of flexibility for family, guests, or a home office. Sliding glass doors open to a covered lanai and a private screened-in, heated saltwater pool and spa, perfect for relaxing and enjoying Florida’s year-round sunshine. The backyard offers added privacy, while the two-car garage and interior laundry room provide everyday convenience. Windsor Palms offers an impressive selection of amenities, including a guarded gated entrance, clubhouse, fitness center, community pool, playground, tennis courts, and more. With short-term rentals permitted, this property is an excellent option as a primary residence, vacation home, or investment property. Schedule your private showing today!

8066 King Palm Circle, Kissimmee

5 Beds ⋅ 4 Baths ⋅ O6434113 MLS ⋅ Na BLDG.

Set on a corner homesite in gated Storey Lake Resort, this fully furnished 5-bedroom, 4-bath townhome gives everyone room to gather and room to recharge. The first floor opens into a bright, connected kitchen, dining, and living space where a granite-topped breakfast bar anchors the kitchen and sliding glass doors keep the private pool in view. Two main-level bedrooms add flexibility for guests, a home office, or multigenerational stays. Outside, the covered patio and screened, heated pool create a private retreat for morning coffee, afternoon swims, and relaxed evenings at home. Upstairs, the primary suite features a walk-in closet and dual-sink bath. An impressive 17-by-15 second-floor guest suite with a private en-suite bath creates another comfortable retreat for extended stays, while a third upstairs bedroom completes the guest-friendly layout. Ceramic tile throughout the main living areas, carpeted bedrooms, in-unit laundry, stainless steel appliances, and a tankless water heater add everyday comfort. Storey Lake’s resort amenities are within easy reach, including resort-style pools, a lazy river, water slides, splash area, clubhouse, fitness center, mini golf, sports courts, playground, and lake access. With furnishings included and Walt Disney World, dining, shopping, and Orlando attractions nearby, this is a turnkey opportunity for a vacation home, second residence, or full-time escape.

3087 Juliet Drive, Kissimmee

4 Beds ⋅ 2 Baths ⋅ O6434115 MLS

Set in the heart of Kissimmee, 1534 Oak Reserve Dr keeps shopping, restaurants, theme parks, the airport, and major roads all within easy reach. This new listing pairs a connected address with a bright, move-in ready interior built for comfortable Florida living. Inside, 1,846 square feet of open, welcoming space await. High ceilings lend each room an airy feel, while the open floor plan links the main living areas for smooth, natural flow. Hard flooring runs through the shared spaces for effortless upkeep, and cozy carpet warms every bedroom, adding a soft, restful touch where it counts. At the center of the home, the kitchen shines with granite countertops and stainless steel appliances, making everyday cooking and casual entertaining simple. A smart split floor plan tucks the primary bedroom away for added privacy, creating a peaceful retreat at day's end. Three additional bedrooms flex easily for family, guests, or a home office, and the seller has added custom closets in the kids'rooms for extra storage. Two full bathrooms keep busy mornings running smoothly. Out back, a screened-in porch invites you to sip morning coffee or unwind in the shade, while a fully fenced yard offers privacy and room to play, garden, or gather. Residents also enjoy community perks like multiple pools and parks. With its handy location, thoughtful layout, and move-in ready condition, this Kissimmee charmer checks every box. Schedule your private showing today and see it for yourself.

1534 Oak Reserve Drive, Kissimmee

5 Beds ⋅ 5 Baths ⋅ O6434446 MLS

Whether you're looking for an income-producing vacation rental or a personal retreat, this 5-bedroom, 5-bath home in the highly desirable gated community of Windsor Hills is an excellent opportunity. The kitchen is positioned at the front of the home and overlooks the formal dining area, creating a welcoming space for family meals and entertaining. The living room is located at the rear of the home and opens to the screened-in pool deck, offering a relaxing space to enjoy the Florida sunshine. Two bedrooms are conveniently located on the first floor, along with two of the bathrooms, while the remaining bedrooms and bathrooms are upstairs, providing comfort and privacy for guests. The garage has been converted into a fun games room with pool and foosball tables, adding extra appeal for renters. Windsor Hills is one of the closest resorts to Disney and features outstanding amenities, including a resort-style pool with water slides, clubhouse, fitness center, and sports courts. Ideal for short-term rental investment, second home, or full-time residence.

7795 Basnett Circle, Kissimmee

2 Beds ⋅ 2 Baths ⋅ O6434424 MLS ⋅ 7 BLDG.

Welcome to Windsor Hills, one of Central Florida’s premier resort communities, located approximately two miles from Walt Disney World. This beautifully updated, fully furnished 2-bedroom, 2-bathroom condo offers turnkey convenience for use as a vacation retreat, short-term rental, or combination of both. Situated on the fourth and top floor of an elevator-served building, the condo is just one block from the clubhouse and water park—close enough for an easy walk while offering a peaceful setting. The bright, open-concept interior features a desirable split-bedroom floor plan, providing privacy for owners and guests. The remodeled kitchen includes quartz countertops, stainless steel appliances, generous workspace, and ample cabinetry. The private primary suite features an en-suite bathroom and walk-in closet. The Mickey Mouse-themed second bedroom offers flexible accommodations with a twin-over-queen bunk bed, twin trundle, foosball table, and custom Disney-inspired mural. The living room includes two leather sofas, one with a pullout bed. Both bathrooms have been fully remodeled with quartz countertops, newer soft-close vanities, custom wood backsplashes, and updated mirrors. Extensive improvements completed in 2022 and 2023 include new flooring and interior paint throughout, remodeled kitchen and bathrooms, stainless steel appliances, updated furniture, ceiling fans, lighting, and themed bedroom décor. Additional updates include a water heater replaced in 2022, and a Samsung washer and dryer installed in January 2026. A private balcony provides the perfect setting for morning coffee or relaxing after a day at the parks. Windsor Hills offers an exceptional collection of resort-style amenities, including a water park with three-story slides, an interactive splash zone, lagoon-style zero-entry pool, hot tub, tiki bar, fitness center, playground, 32-seat movie theater, putting green, arcade, convenience store, cybercafé, and tennis, basketball, and volleyball courts. The community also features 24-hour guard-gated security, convenient parking, oversized-vehicle access, and designated RV parking. Zoned for short-term rentals and offered fully furnished, this condo is ready for personal enjoyment or rental use after closing. Windsor Hills provides convenient access to Walt Disney World, Universal Orlando Resort, SeaWorld, area airports, US-192, I-4, and SR-429. Don’t miss this opportunity to own a top-floor condo in one of Central Florida’s most recognized vacation communities. Schedule your private showing today!

2817 Almaton Loop Unit 402, Kissimmee

10 Beds ⋅ 10 Baths ⋅ O6433659 MLS

Discover an exceptional SHORT-TERM RENTAL INVESTMENT OPPORTUNITY in the highly sought-after Encore Resort at Reunion. This beautifully appointed 10-bedroom, 10-bathroom TURNKEY vacation home is thoughtfully designed to accommodate large groups, multi-generational families, reunions, and Orlando vacationers, comfortably SLEEPING 20+ GUESTS. The spacious, open-concept floor plan is ideal for the vacation rental market, offering plenty of room for guests to gather while still enjoying their own private spaces. The gourmet kitchen is designed with large groups in mind and features dual refrigerators, two dishwashers, generous prep space, and sleek luxury vinyl flooring throughout the main living areas. Sliding glass doors create a seamless transition from the living and dining areas to the outdoor retreat, featuring a covered lanai, heated pool, and spa. With NO REAR NEIGHBORS and peaceful views of a greenbelt/conservation area, the backyard offers the privacy and setting vacation guests are looking for, whether enjoying a morning by the pool or relaxing after a day at Orlando's world-famous attractions. The home's impressive bedroom configuration adds to its rental appeal. Nine of the 10 bedrooms feature en-suite bathrooms, including two primary suites, one upstairs and one downstairs. A main-level accessible suite with a private accessible bathroom provides additional flexibility for guests. Upstairs, a spacious loft with a foosball table and an additional great room create even more entertainment and gathering space. Located within Encore Resort at Reunion, owners and guests can enjoy access to an impressive collection of resort-style amenities, including a spectacular clubhouse, award-winning restaurant, water park, full-service spa, playgrounds, state-of-the-art fitness center, and basketball, volleyball, and tennis courts. The community also offers gated entrances with 24-hour security and convenient resort services. A concierge desk is available at the clubhouse to assist guests with theme park tickets, dining, airline check-ins, resort-provided park shuttles, and more. Ideally positioned near Walt Disney World and Central Florida's premier attractions, as well as golf, shopping, dining, and entertainment, this property offers the combination vacation rental investors are looking for: size, guest-friendly amenities, privacy, resort appeal, and a prime Orlando-area location. Whether adding to an existing short-term rental portfolio or entering the Orlando vacation rental market, this Encore Resort property offers a compelling opportunity in one of Central Florida's most popular vacation destinations. Schedule your private tour today!

7519 Marker Avenue, Kissimmee

11 Beds ⋅ 10 Baths ⋅ O6433708 MLS

Welcome to an exceptional TURNKEY SHORT-TERM RENTAL INVESTMENT OPPORTUNITY in Encore Resort at Reunion, just minutes from Orlando’s world-famous theme parks. This fully furnished 11-bedroom, 10-bathroom vacation home is designed with large groups and vacationers in mind, comfortably SLEEPING 20–24 GUESTS and offering an impressive combination of space, entertainment, and resort-style amenities. The spacious open-concept floor plan features a gourmet kitchen equipped with two refrigerators and two dishwashers, along with generous dining and living areas ideal for accommodating large groups. Three bedrooms are conveniently located on the main level, including a bedroom with an accessible en-suite bathroom. Upstairs are eight additional bedrooms, including four custom-themed bunk rooms inspired by Marvel, Ghostbusters, Spiderman, and Pirates of the Caribbean, creating memorable spaces for younger guests. One of the home’s standout features is the converted Star Wars-themed game room, complete with a life-size R2-D2, air hockey, Aliens Extermination, Expert Shot Basketball, and two NASCAR virtual racing arcade games. Additional gathering spaces and laundry rooms on both levels add convenience for larger groups and extended stays. Sliding glass doors from the living area open to a covered patio, private heated pool and spa, and mature landscaping that provides additional privacy. It’s an inviting outdoor retreat where guests can relax and recharge after a day at the parks. Located within Encore Resort at Reunion, owners and guests can enjoy access to an impressive collection of resort amenities, including a clubhouse, restaurant, water park, full-service spa, playgrounds, fitness center, and basketball, volleyball, and tennis courts. The gated community also offers security, concierge services, and resort-provided transportation to area theme parks. With its 11-bedroom layout, themed bedrooms, incredible game room, private pool and spa, and prime location near Walt Disney World and Central Florida attractions, this property is ideally suited for the Orlando vacation rental market. Whether adding to an existing portfolio or looking for a turnkey short-term rental investment, this Encore Resort home offers the space, features, and guest experience to stand out. Schedule your private tour today!

7643 Wilmington Loop, Kissimmee

4 Beds ⋅ 3 Baths ⋅ S5155807 MLS

Welcome to **4385 Twisted Twig Bnd**, a spacious **4-bedroom, 2.5-bath home located in the desirable Storey Creek community of Kissimmee**. Built in 2024 and offering approximately **2,357 square feet of living space**, this home combines comfort, functionality, abundant natural light, and one of its most attractive features: **no rear neighbors and peaceful views of a natural area**, creating added privacy and a relaxing setting. The main living area features an appealing **open-concept layout** that seamlessly connects the family room, dining area, and modern kitchen, creating an ideal space for everyday living and entertaining. The kitchen includes **quartz countertops, stainless steel appliances, shaker-style cabinetry, an undermount sink, LED lighting, and a large center island**. Upstairs, the spacious **owner’s suite** features a **private en-suite bathroom and a large walk-in closet**. Three additional bedrooms, a **versatile loft**, and a conveniently located laundry room provide flexible space for family, guests, a home office, or additional living areas. The property also features a **2-car garage plus a driveway with space for 2 additional vehicles**, adding convenience and functionality for everyday living. Storey Creek enhances the lifestyle with excellent community amenities including a **resort-style swimming pool, clubhouse, fitness center, playground, dog park, and basketball court**. Its convenient location provides easy access to **shopping, dining, schools, medical services, major roadways, and Central Florida’s renowned attractions**. **Schedule your private showing today and experience the spacious layout, natural light, added privacy with no rear neighbors, and the Storey Creek lifestyle that make this home stand out.**

4385 Twisted Twig Bend, Kissimmee

Start Your Search