Kissimmee Homes with Private Pool type

Kissimmee Homes with Private Pool type

Welcome to Kissimmee, Florida – a vibrant city that perfectly blends the magic of theme parks with the charm of a quaint community. Nestled in Osceola County, Kissimmee is a gateway to some of the world’s most renowned attractions, including Walt Disney World, Universal Studios, and SeaWorld. But beyond the thrill of the parks, this city offers a warm, welcoming atmosphere filled with beautiful landscapes, diverse dining options, and a variety of recreational activities.

One of the standout features of homes in Kissimmee is the availability of properties with private pools. Imagine stepping into your own backyard oasis, where you can unwind after a day of adventure in the Florida sun. Homes with private pools in Kissimmee are not just a luxury; they provide a perfect retreat for families and vacationers alike. Whether you’re enjoying a morning swim, hosting a barbecue, or simply soaking in the sun, a private pool enhances your living experience and adds a touch of tranquility to your home.

Kissimmee's real estate market boasts a diverse range of options, from cozy townhomes to luxurious villas, many of which come equipped with stunning pool areas. These homes are ideal for both permanent residents and those looking for vacation rentals, offering an excellent investment opportunity in a city that attracts millions of visitors each year.

Discover the joy of living in Kissimmee, where the allure of Florida living meets the comfort of home. With a private pool as your personal retreat, you’ll find that every day feels like a holiday. Come explore your dream home in this enchanting city today!

Newest Kissimmee Homes with Private Pool type

1113 Castle Pines Court, Reunion
$899,000
6 Beds ⋅ 6 Baths ⋅ Reunion West Village 03a SubDv. ⋅ 34747 Zip Code
RESORT MEMBERSHIP AVAILABLE: The best priced 6 bedrooms on the market with adjacent lot available for purchase. Amazing opportunity to own a fantastic 6 bedroom home in Reunion Resort. This home is heavily used by homeowner. Impeccably styled and thoughtfully designed, this stunning home offers the perfect blend of luxury, comfort, and resort-style living. The open-concept first floor creates an ideal setting for both everyday living and entertaining, seamlessly connecting the spacious living room and gourmet kitchen so everyone can gather while meals are prepared. The living area is bright and inviting, featuring a soothing neutral color palette, an oversized sectional, multiple seating areas, and space designed to accommodate the whole family. The chef’s kitchen is equipped with stainless steel appliances, granite countertops, abundant cabinetry, and a generous breakfast bar with seating for six. Adjacent to the living space, the dining area offers a large table that comfortably seats eight—perfect for hosting family dinners or guests. The primary suite is conveniently located on the first floor with elegant finishes, and a spa-inspired en-suite bath featuring dual vanities, a soaking tub, and an oversized walk-in shower. Upstairs, you’ll find five additional bedroom suites, including one with a private balcony overlooking the golf course. Two themed bedrooms add a fun and unique touch, making this home especially appealing for families and guests. A spacious loft provides an additional gathering space with a large sectional and gaming setup, while the dedicated home theater delivers an immersive movie-night experience. Step outside to your own private pool deck, where serene golf course views create a peaceful backdrop for swimming, relaxing, or entertaining. The outdoor summer kitchen makes al fresco dining effortless—ideal for barbecues and evenings under the stars. Located within the prestigious, amenity-rich Reunion Resort, enjoy access to three world-class PGA Championship golf courses, multiple resort pools, a five-acre water park with a lazy river and slides, tennis and sports courts, a full fitness center, spa services, and a variety of on-site dining options. Whether used as a primary residence, second home, or luxury vacation rental, this exceptional property delivers the lifestyle and location buyers seek in one of Central Florida’s most desirable resort communities.

1113 Castle Pines Court, Reunion
1848 Sandy Park Trail, Kissimmee
$529,000
6 Beds ⋅ 5 Baths ⋅ Solara Resort SubDv. ⋅ 34747 Zip Code
Welcome to your dream vacation retreat in the heart of Kissimmee! This stunning 6-bedroom, 4.5-bathroom home in the highly sought-after Solara Resort offers the perfect blend of luxury, comfort, and investment appeal. Featuring an elegant open-concept layout, two spacious primary suites, generously sized bedrooms, and a private pool, this beautifully appointed home is designed for unforgettable stays and effortless entertaining. A proven and highly productive rental property, the home has enjoyed consistently strong demand, making it an excellent opportunity for investors seeking an established income-producing property. Solara Resort offers world-class amenities, including a resort-style clubhouse, heated pool, Flow Rider® surf simulator, fitness center, sports courts, playground, game room, restaurant, bar, lounge areas, and more. Ideally located just minutes from Disney, dining, shopping, and Orlando’s premier attractions, this exceptional property is a perfect choice for a vacation home, second residence, or short-term rental investment. Whether relaxing poolside or exploring all that Central Florida, this home delivers the ultimate resort lifestyle.

1848 Sandy Park Trail, Kissimmee
3151 Yellow Lantana Lane, Kissimmee
$415,000
4 Beds ⋅ 3 Baths ⋅ Encantada Ph 1 SubDv. ⋅ 34747 Zip Code
Ultimate flexibility meets premium LOCATION!, LOCATION, LOCATION!!! Nestled in the highly desirable gated community of Encantada Resort, this beautiful 4-bedroom, 3-bathroom premium corner-lot townhome offers a true quiet oasis. Step outside to your private pool and soak in peaceful views of the community lake. Boasting 1,636 sq ft of optimized living space, the layout features a highly convenient downstairs bedroom with the remaining bedrooms upstairs. The layout of the kitchen, dining room and living room provide a welcoming open concept for larger groups opening to the private pool and screened patio. This premium end unit boasts extra windows, offering a significantly brighter and more open living space. Enjoy the best lake views and a very short, scenic walk around the water to the resort-style community pools, clubhouse, fitness center and restaurant. Located just minutes from world-class theme parks and local dining. Zoned for short-term rentals, a part-time vacation getaway, or your primary residence—the choice is yours! Fully furnished and turnkey potential in an unbeatable Central Florida location.

3151 Yellow Lantana Lane, Kissimmee
2736 Bookmark Drive, Kissimmee
$599,000
6 Beds ⋅ 5 Baths ⋅ Cove At Storey Lake Ii SubDv. ⋅ 34746 Zip Code
Welcome to your dream vacation retreat! This fully furnished 6-bedroom, 5-bathroom home is nestled in the highly sought-after Storey LakeResort, offering the ultimate in resort-style living with unparalleled amenities. Decorated to perfection, this stunning home features spaciousliving areas, an elegant modern kitchen, and beautifully designed bedrooms. Step outside to your screened private pool and spa, providing theperfect retreat for relaxation and entertainment. Storey Lake is a gated community boasting multiple clubhouses, resort-style pools, lazy river,waterslides, fitness center, volleyball and tennis courts, and more! The HOA covers lawn maintenance, internet, cable, and daily valet trashservice for a seamless experience. Conveniently located near world-class shopping, dining, and top attractions, this home is perfect for avacation retreat or a lucrative investment property. Don’t miss out—schedule your showing today!

2736 Bookmark Drive, Kissimmee
7491 Gathering Drive, Kissimmee
$1,420,000
5 Beds ⋅ 5 Baths ⋅ Reunion Ph 1 Prcl 1 Unit 3 SubDv. ⋅ 34747 Zip Code
Luxury, Legacy and Lifestyle are on display at one of Reunion’s most unique floorplans and it’s yours to enjoy at 7491 Gathering Drive. *REUNION RESORT MEMBERSHP** Home went through a series of major upgrades. Nestled in the historic Homestead Community at Reunion Resort you will find this 4,664 square foot home that offers 2 OVERSIZED SUITES, a large open floor plan, along with a home office, loft and media spaces and an extremely private SCREENED in pool and spa area. The home is surrounded by mature trees and really feels like the best of Golf Course Community Living. You enter the home and are greeted by tall ceilings, a large staircase and tons of natural light. Once inside you will see that the first floor of the home wraps itself around the pool area and this sets the tone for relaxation. The home office is a new addition to the property and is the perfect way to be able to enjoy working from home but be careful, you could get caught daydreaming about jumping in the pool. Exploring deeper into the home you will see great use of space with an oversized open concept kitchen and living area. New countertops, reimagined island space and white cabinets only add to the clean lines of the home. Along with bar stool seating there is a separate dining area that is well thought out and very accommodating. Glass doors outline the back wall of the property and create an Oasis like feeling while also giving you pristine golf course views. You are located on the Watson Course, hole number 2. Once outside on the first-floor patio of the home you are then again reminded of the quietness of the property and the green space that surrounds you. There are two bedrooms on the first floor of the home that have been re-imagined spaces. At the rear of the home is where you will find one of two master suites at the property. It is accented by a large walk-in closet space and large picture windows that are framed by exterior foliage. A laundry room and a spacious 2 CAR GARAGE round out the first floor. Upstairs you are greeted by new designs that include new flooring, an additional bathroom, re-designed shower spaces and re-thought media and loft areas that help the home continue to excite. The media room has a newly installed oversized projection screen and projector. The additional three bedrooms are located on the second floor led by the second master suite that overlooks the golf course. The second master also has received special attention during the re-imagination and now boasts a spa like feel with a new shower and seating area. The large game room loft is connected to the second story balcony and does not disappoint. You can watch golf on the big screen and on the balcony at the same time! This home has it all. 7491 Gathering Drive, does have an active Reunion Resort Transferable Membership, along with tankless water heaters and 1 new AC and newer roof. If you are looking for the best of quiet Golf Course living in Reunion, you have found it. Reunion Resort has everything you want in a community including 3 signature golf courses, world class dining, waterparks, lazy river, water slides, firework viewing areas, tree lined streets, dog park, playground, golf simulator, member events, in-resort shuttle service, and event space and close to all the major attractions. Welcome Home!

7491 Gathering Drive, Kissimmee
1097 Castle Pines Court, Kissimmee
$950,000
5 Beds ⋅ 4 Baths ⋅ Reunion West Village 3a SubDv. ⋅ 34747 Zip Code
Luxury, Legacy and Lifestyle! Where are you having thanksgiving this year? OVER 3300 square feet with pristine GOLF COURSE views and nestled in the Highly Desirable Fairway Ridge Portion of Reunion Resort. Don’t settle for anything less than this spectacular custom-built home. You will not find this level of attention to detail and charm in any home of this size. EXTREMLY WELL MAINTAINED WITH NEW THEMED GARAGE MAKE OVER! The pool and outdoor space really stands out for style and size. Respectfully, the pictures do not tell the real story. The home has been energized with brand new paint inside and out. The Zen feeling in the home promotes a truly calm and tranquil feeling. When walking into the home your eyes are instantly drawn down the custom hallway into the large gathering space. The calm color palette is inviting and makes you start realizing there is something different about this home. The first-floor bedroom and that is hidden behind a secret hidden doorway. Once you discover the bedroom, you will want to see more of the home. The custom wood archway flows into a large open floor plan. Custom kitchen wood cabinetry, stainless steel appliances, granite countertops, and an island that should have its own zip code. Tons of seating for a quick bite or enjoying a glass of wine while a private chef entertains. Across from the kitchen behind a glass door there is a separate custom wine closet and storage area outfitted with a custom wine fridge. The living room is arranged with form and function in mind. A large comfortable sitting area with perfectly picked out furniture lets you know that not a detail was missed. The first-floor windows are also nicely accented with plantation shutters. After the inside of the property captures you, make your way outside through the oversized sliding glass door to the pool area. A covered lanai that is the width of the home shades you from the Florida rays. The pool and hot tub overlook the Nicklaus golf course and is the perfect place for some private swimming and lounging. The second floor is introduced to you by a wooden staircase and then you are greeted by a large loft area. The Master has a large walk-in closet and large master bath. There is also an oversized shower area. The back of the home also features a private master bedroom balcony which is the perfect escape for a early morning coffee. Reunion has it all! Three Signature Golf Courses- The Watson, The Palmer and The Nicklaus weave their way through the rolling landscape of the resort. The Tree lined streets make for great long walks or bike rides. Reunion boasts great dining options from a ROOF TOP TAPAS RESTURANT AND BAR, to THE CHOP HOUSE. Maybe its sushi in the lobby or a trip to a Reunion Hot Spot- THE NICKLAUS CLUBHOUSE. A Golf Cart Friendly community that is filled with activities for all, including Tennis, Putt-Putt, Pickle Ball, Member Events, Parties and a waterpark. If living or visiting Reunion, remember it is super close to theme-parks, shopping, and beaches. A Gated Community that works hard on staying the nicest in the area. This property is in a short-term rental program- which can really help it make sense when you not using it. The home will come fully furnished. Schedule a viewing today. It is in a STR program and does come with an ***ACTIVE REUNION RESORT MEMBERSHIP***

1097 Castle Pines Court, Kissimmee
7605 Brookhurst Lane, Kissimmee
$650,000
6 Beds ⋅ 7 Baths ⋅ Reunion West SubDv. ⋅ 34747 Zip Code
Welcome to Magical Memories Mansion, a premium, fully furnished, turnkey luxury vacation home located in the guard-gated Encore Resort at Reunion. Situated less than seven miles from Disney, this expansive 6 bedroom, 6.5 bath retreat is designed to accommodate 16+ guests with ease. Thoughtfully planned for comfort and short-term rental appeal, every bedroom functions as its own private suite, giving guests added privacy while maximizing flexibility for groups of families and friends. This home delivers a truly immersive experience with Disney-inspired theming throughout. The spectacular Little Mermaid suite features hand-painted, floor-to-ceiling murals, two custom-built bunk beds that sleep four, a sculpted Ariel detail, and a one-of-a-kind slide that transitions into a Cars-themed bonus room with Radiator Springs-inspired rockwork. Nearby, the Pirates of the Caribbean suite offers another fully hand-painted retreat, highlighted by a custom pirate ship-style queen/twin bunk bed and a sculpted Captain-inspired centerpiece. For younger heroes, the Marvel/Avengers room provides a customized bunk bed plus an additional twin. The Frozen suite includes a queen bed and a full-size crib, offering a convenient setup for the youngest princes and princesses. Both the Star Wars first-floor primary suite and the Brave second-floor primary suite provide comfortable, private accommodations with walk-in closets. The gourmet kitchen and dining area continues the storytelling with a Beauty and the Beast theme, complemented by granite countertops, stainless steel appliances, abundant wood cabinetry, and seating for 16+ guests. Additional themed spaces extend through the home with Peter Pan and Sleeping Beauty-inspired hallways, along with a charming Cinderella laundry room. Outside, the property becomes a private resort oasis with a heated pool and spa, lush tropical landscaping and hardscaping, outdoor solar lighting, two new teal hammocks with stands, and matching lounge chairs—an ideal place to relax after a day in the parks. The home has been meticulously upgraded and maintained, including new updates in 2025 such as a 5-ton HVAC system, an over-the-range microwave, a washer integrated into the stackable washer/dryer, gray waterproof luxury vinyl plank flooring throughout, professional landscaping and solar lighting, leaf-blocking gutters and downspouts, a Nest security system with cameras plus Nest doorbell, an Ecobee thermostat, upgraded outdoor furniture, and a new pool pump and heater. It also includes new mattresses and protective bedding, featuring zippered waterproof mattress protectors, pillow protectors, and waterproof elastic mattress pads. Family-friendly essentials are also included, including a crib, changing table, Pack ’n Play with mattress, high chair, and additional baby and child amenities to make traveling with little ones easier. The two-car garage features epoxy flooring and an air conditioning unit, with the ability to park your vehicle while also providing extra usable space for activities, including the included pool table. For owner convenience, the home includes multiple fingerprint-coded, app-controlled owners closets, including a large walk-in closet on the second floor and two linen closets on the second floor. Finally, as part of the guard-gated Encore Resort at Reunion, owners and guests enjoy world-class amenities such as a resort water park with thrilling slides.

7605 Brookhurst Lane, Kissimmee
2911 Banana Palm Drive, Kissimmee
$335,000
4 Beds ⋅ 3 Baths ⋅ Paradise Palms Residence Ph 4 SubDv. ⋅ 34747 Zip Code
Welcome to your turnkey Florida retreat in the gated Paradise Palms Resort community! This beautifully updated, furnished 4-bedroom, 3- full bath townhome features fresh interior paint, luxury vinyl flooring, an open great area, and a spacious kitchen with granite countertops and wood cabinetry. The split-bedroom layout includes a first-floor bedroom and full bath, with the primary suite and two additional bedrooms upstairs. Enjoy your private screened-in pool, covered patio, and fenced backyard—or walk to the resort’s impressive amenities, including a lagoon-style pool with slide and waterfall, spas, Tiki bar and grill, movie theater, fitness center, sauna, arcade, and sports courts. HOA services include cable, phone, high-speed internet, trash valet, security, and common-area maintenance. Short-term rentals are permitted, offering flexibility for personal use and rental income potential. Conveniently located near Disney, Universal, SeaWorld, shopping, dining, and major highways. This home is ideal as a vacation getaway, investment property, or full-time residence.

2911 Banana Palm Drive, Kissimmee
2541 Jasmine Trace Drive, Kissimmee
$490,000
4 Beds ⋅ 3 Baths ⋅ Jasmine Pointe At Crescent Lakes SubDv. ⋅ 34758 Zip Code
2541 Jasmine Trace Dr is a two-story Kissimmee home in Crescent Lakes featuring a screened-in swimming pool and an open, light-filled layout. Soaring two-story ceilings and clerestory windows highlight the main living room, where hardwood floors and sliding glass doors connect directly out to the pool deck and covered lanai. The central kitchen features white cabinetry with glass-front display uppers, dark granite countertops, stainless steel appliances, and an island with breakfast-bar seating. An open staircase leads up to a gallery loft overlooking the living areas below. The primary suite includes custom built-in closet shelving and an ensuite bath with dual vanities, a deep soaking tub, and a step-in shower. A dedicated laundry room and an attached two-car garage complete the home, located near neighborhood lakes, community trails, and Central Florida conveniences. Included 100-Day Home Warranty with buyer activation

2541 Jasmine Trace Drive, Kissimmee
2948 Penelope Loop, Kissimmee
$730,000
6 Beds ⋅ 6 Baths ⋅ Cove At Storey Lake 4 SubDv. ⋅ 34746 Zip Code
Save Big: 1% lender credit (based on loan amount) toward closing costs or rate buy-down with seller’s preferred lender. Ask for details! | INVESTMENT OPPORTUNITY IN THE COVE AT STOREY LAKE! This spacious 6 bedroom, 6 bathroom pool home offers an exceptional combination of resort-style living and a proven track record as a successful vacation rental. Future bookings are already scheduled and can be transferred to the new owner if the current management company is kept in place. Documentation indicates that over $130,000 in gross rental revenue has been generated in the last 12 months, providing an opportunity for rental income to start from day one. Designed to comfortably accommodate large groups, the home offers an abundance of living and entertaining space. The flexible floor plan features a theater with the addition of a bonus room downstairs and a spacious loft upstairs, providing multiple areas for guests to gather, relax, play, or entertain. Step outside to your own private Florida retreat featuring a paver lanai, screened pool and spa, and peaceful views of the conservation area behind the home. With no immediate rear neighbor, guests can enjoy additional privacy while relaxing poolside after a day at Central Florida's attractions. Located within The Cove at Storey Park, owners and guests enjoy access to an impressive collection of resort style amenities, including community pools, lazy river, hot tub, water slide, splash park, fitness center, basketball and volleyball courts, tiki bar, and more. Mini golf and kayaking are also available for an additional fee. The gated resort community provides 24-hour controlled access and is conveniently located near Walt Disney World, Universal Orlando, shopping, dining, grocery stores, and other Central Florida attractions. This property has a strong vacation rental history, boasting a guest rating of 4.92 out of 5 based on reviews. Whether you are looking for an income-generating vacation rental, a second home close to Orlando's attractions, or a spacious Florida retreat with resort-style amenities, this home offers the ideal combination for today's vacation home buyers.

2948 Penelope Loop, Kissimmee
4773 Cumbrian Lakes Drive, Kissimmee
$470,000
4 Beds ⋅ 4 Baths ⋅ Cumbrian Lakes Resort SubDv. ⋅ 34746 Zip Code
Welcome to your next home in Kissimmee, just 15 minutes from Walt Disney World Resort! This fully furnished four-bedroom, three-bath pool home in a secure gated community is an amazing investment opportunity. Split floor plan, with beautiful master suite. Kitchen is an open concept, ideal for entertaining. Location is key, close to Disney, shopping and dining. The nearby Loop offers 70 stores and 15 restaurants for endless options. Beautiful pool and lanai overlooking a serene lake. Recent updates include new roof (2026), newer air-conditioning unit (2024), new dishwasher (2025), repainted exterior (2025) and new pool pump (2026). This is a turnkey property, ready for Airbnb success or personal enjoyment. Don't miss out on this chance to enter into the world of income-generating real estate.

4773 Cumbrian Lakes Drive, Kissimmee
1852 Caribbean View Terrace, Kissimmee
$799,000
9 Beds ⋅ 7 Baths ⋅ Solara Resort SubDv. ⋅ 34747 Zip Code
Step into paradise and experience the ultimate luxury lifestyle at "Wizarding Wonderland," located at 1852 Caribbean View Terrace! This exceptional, fully furnished 9-bedroom, 6.5-bathroom retreat in the prestigious, gated Solara Resort offers comfort, fun, and effortless group entertaining. Ideal as a magical vacation destination, multi-generational primary residence, or turnkey investment property, this spacious layout accommodates large gatherings with ease. Highlights include designer king- and full-sized suites, captivating wizard- and Hawaiian-themed kids' rooms, and a custom garage-converted home theater complete with a 100-inch projection screen and plush leather recliners. For nonstop entertainment, enjoy a dedicated arcade room packed with classic games, plus a separate upstairs lounge loft with additional games and a karaoke setup. Step outside to your private oasis featuring a screened-in pool with spillover spa, a 12-seat patio dining table, sun loungers, and poolside games—delivering the ultimate indoor-outdoor Florida lifestyle. Beyond the front door, owners and guests enjoy seamless access to Central Florida's top attractions—including Walt Disney World, Universal's Epic Universe, world-class dining, and premier shopping. Positioned just moments from Solara Resort’s world-class clubhouse amenities, residents can take advantage of the FlowRider® surfing simulator, heated Grand Pool, splash parks, full-service fitness center, sports courts, and on-site dining. Whether you are looking for an extraordinary family vacation home or an asset in one of Orlando's most sought-after resort communities, this property offers an unparalleled turnkey opportunity.

1852 Caribbean View Terrace, Kissimmee
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