Kissimmee/Celebration Homes with Pool

Kissimmee/Celebration Homes with Pool

Welcome to the enchanting region of Kissimmee and Celebration, Florida, where sunshine meets serenity! Nestled in the heart of Osceola County, this vibrant area is known for its picturesque landscapes, rich history, and close proximity to world-renowned attractions like Walt Disney World and Universal Studios. With its warm climate and lush greenery, Kissimmee offers a perfect blend of urban amenities and natural beauty, making it an ideal place to call home.

In Kissimmee, you’ll discover a diverse array of homes, many of which come with the added luxury of private pools. Imagine stepping out into your own backyard oasis, where you can bask in the Florida sun or take a refreshing dip at any time of the day. Homes with pools in this area are not just a luxury; they are a lifestyle choice that enhances your living experience. Whether you’re hosting a summer barbecue, enjoying a quiet morning coffee by the water, or unwinding after a long day, a pool provides the perfect backdrop for relaxation and entertainment.

Celebration, a charming community designed by The Walt Disney Company, is just a stone's throw away from Kissimmee. With its quaint streets, delightful shops, and community events, Celebration exudes a small-town charm that complements the excitement of nearby attractions.

Whether you’re looking for a family home, a vacation getaway, or a lucrative investment opportunity, Kissimmee and Celebration offer an array of options that cater to every lifestyle. With homes featuring stunning pools and a vibrant community spirit, this region invites you to dive into a life of comfort and joy. Come explore the possibilities that await you in this magical corner of Florida!

Newest Kissimmee/Celebration Homes with Pool

no property photo
$900,990
4 Beds ⋅ 3 Baths ⋅ O6455472 MLS
Under Construction. This Heron is a thoughtfully designed 2-story family home in Central Florida, offering spacious, open-concept living perfect for modern lifestyles. This 4-bedroom, 2.5-bath home includes a loft, ideal for a playroom or additional living space. The first-floor flex room was converted/upgraded into a private study. The chef-inspired gourmet kitchen features a 30” natural gas cooktop with stainless steel vent hood and built-in microwave and oven in the cabinetry. Quartz countertops complete the elevated look on your breakfast bar. A morning kitchen featuring additional cabinets and counter space leads to the walk-in pantry with ventilated shelving. Designed for comfort and functionality, the Heron combines a flexible layout with premium finishes and a prime location near shopping, dining, parks, and top-rated schools—making it an ideal choice for families seeking new homes in Celebration, FL.

2522 Celebration Boulevard, Kissimmee
400 Lasso Drive, Kissimmee
$640,000
6 Beds ⋅ 6 Baths ⋅ O6451936 MLS
EXCEPTIONAL OPPORTUNITY! MOTIVATED SELLER! ELEGANTLY APPOINTED, FULLY FURNISHED 6-BEDROOM, 6-BATH POOL HOME IN GATED ENCORE CLUB AT REUNION! Discover an exceptional combination of comfort, sophistication, entertainment, and versatility, complete with HIGH-QUALITY FURNISHINGS throughout. Whether you're seeking a PRIMARY RESIDENCE, SECOND HOME, VACATION RETREAT, or SHORT-TERM RENTAL INVESTMENT, this impressive property offers something for everyone. With its private pool, outstanding entertainment spaces, extensive HOA-included services, and desirable resort location, this is a compelling opportunity to enjoy Central Florida living! Offering 2,822 square feet, this two-story residence features SIX SPACIOUS BEDROOMS, EACH WITH ITS OWN PRIVATE EN-SUITE BATHROOM, providing exceptional privacy and comfort for family and guests alike. The inviting OPEN-CONCEPT FLOOR PLAN features generous living and dining areas and a beautifully appointed kitchen with granite countertops, 42-inch cabinetry, and a LARGE CENTER ISLAND. The living area flows seamlessly to the COVERED PATIO and PRIVATE POOL, perfect for entertaining, relaxing, and enjoying Florida's sunshine year-round! ENTERTAINMENT IS A STANDOUT FEATURE! The garage has been transformed into a DEDICATED, AIR-CONDITIONED MOVIE AND GAME ROOM, providing ADDITIONAL FUNCTIONAL RECREATIONAL SPACE. Complete with ELEVATED MOVIE SEATING, LARGE MOVIE SCREEN AND PROJECTOR, VIDEO GAMING TV, POOL TABLE, and FOOSBALL TABLE, this incredible space is perfect for family fun and memorable gatherings. TWO THEMED BEDROOMS add another distinctive touch for guests of all ages. ELEGANTLY FURNISHED AND READY TO ENJOY! HIGH-QUALITY FURNISHINGS create a welcoming, upscale atmosphere throughout, offering the convenience of a fully furnished home without the added expense of furnishing six bedrooms and multiple entertainment spaces. Five bedrooms and the laundry room are upstairs, with LUXURY VINYL PLANK FLOORING in all bedrooms. Additional highlights include NO CARPET THROUGHOUT, 8-FOOT INTERIOR DOORS, and RECENT INTERIOR AND EXTERIOR PAINT. ENJOY LOW-MAINTENANCE OWNERSHIP WITH EXTENSIVE HOA-INCLUDED SERVICES! HOA fees cover PRIVATE POOL MAINTENANCE, LAWN CARE AND LANDSCAPING, PEST CONTROL, CABLE TELEVISION, INTERNET, TRASH, and other community services. These valuable inclusions simplify ownership whether you're living here full-time, visiting seasonally, or utilizing its rental potential. Located within GUARD-GATED ENCORE CLUB AT REUNION, residents and guests can enjoy resort-style amenities including a WATER PARK, SPORTS COURTS, ARCADE, FITNESS CENTER, RESTAURANT, BAR, and MARKET, subject to applicable access provisions. Conveniently located near THEME PARKS, championship golf, shopping, dining, and Central Florida's world-famous attractions! SELLER IS HIGHLY MOTIVATED AND READY TO CONSIDER OFFERS! SCHEDULE YOUR PRIVATE SHOWING TODAY AND DISCOVER THE EXCEPTIONAL VALUE THIS PROPERTY HAS TO OFFER! PROPERTY IS ON A SHORT-TERM RENTAL PROGRAM CURRENTLY BUT EVERY EFFORT WILL BE MADE TO ACCOMMODATE SHOWING REQUESTS FOR QUALIFIED BUYERS.

400 Lasso Drive, Kissimmee
7944 Jacks Clb Drive, Kissimmee
$1,895,000
6 Beds ⋅ 7 Baths ⋅ R4912308 MLS
A fully transferable membership is available with this home. A luxury home in the gated Bear’s Den at Reunion Resort, backing directly to the Jack Nicklaus Signature Golf Course. Offering 6 bedrooms, 6 full baths, 1 half bath, and 4,588 heated square feet (over 6,200 total square feet), this modern home is designed for effortless primary living or a turnkey short-term rental powerhouse. Outside, enjoy a pool deck with a heated pool, integrated sun shelf, elevated stone spillover spa, and panoramic fairway views. The covered summer kitchen includes a stainless steel grill with commercial hood, prep sink, granite counters, outdoor TV, and dining area. Upstairs, a private covered viewing balcony overlooks the course. Inside, entertainment highlights include a dedicated private cinema room, and games room and two immersive, themed bedrooms—one inspired by Mario and another designed around 20,000 Leagues Under the Sea. Five of the bedrooms feature their own private en-suite bathroom and there is also a main-level powder room. The full laundry suite features solid-surface counters and extensive storage. The main living area, kitchen and dining are open and airy and have all the luxuries to be expected in a house of this caliber. Reunion Resort amenities include 24-hour guarded security, three championship golf courses (Nicklaus, Palmer, Watson), a multi-acre water park with lazy river, tennis and pickleball courts, a fitness center and on-site dining including the rooftop Eleven and Chophouse steak restaurant, all just minutes from Disney.

7944 Jacks Clb Drive, Kissimmee
8958 Cat Palm Road, Kissimmee
$357,000
4 Beds ⋅ 3 Baths ⋅ O6454797 MLS ⋅ - BLDG.
Elegant Vacation Home with Private Pool in Paradise Palms Resort – Excellent Investment Opportunity! Welcome to this beautifully renovated vacation home located in the highly desirable Paradise Palms Resort, just 7 miles from Walt Disney World and approximately 20 miles from Universal Studios! Whether you're looking for a profitable short-term rental investment or the perfect vacation home for your family, this property offers the best of both worlds. Designed to comfortably accommodate 8–12 guests, this home features a private pool, a gourmet kitchen, and an open-concept floor plan, creating the perfect setting for relaxation and entertainment. The property has earned Airbnb's Guest Favorite recognition, making it an attractive opportunity for investors looking to generate rental income from day one. Enjoy the convenience and security of a 24-hour guard-gated community, along with an impressive selection of resort-style amenities, including a clubhouse, resort-style swimming pool, spa, fitness center, movie theater, tennis court, and playground. Ideally located with easy access to US-192, I-4, and major attractions, the property offers convenient connections to Orlando, Davenport, Clermont, and Tampa. Even better, the sale includes high-quality furnishings and existing rental bookings, offering a seamless transition for the new owner! Don't miss this opportunity to own a beautifully updated vacation property in one of Central Florida's most desirable resort communities!

8958 Cat Palm Road, Kissimmee
7446 Excitement Drive Unit 103, Kissimmee
$399,000
3 Beds ⋅ 2 Baths ⋅ O6455590 MLS ⋅ 5 BLDG.
Under Construction. NEW CONSTRUCTION ** Experience life at The Crescent at Reunion, a gated resort community where three signature golf courses, tennis courts, a water park and on-site dining are all within the resort. Start the day on the course, spend the afternoon by the water and finish with dinner close to home. Exclusive Reunion Resort membership is included with the property deed, subject to applicable membership fees and terms. Walt Disney World, shopping and dining are nearby. Recently reduced in price and ready for immediate occupancy, this newly built 3-bedroom, 2-bath condo offers approximately 1,125 square feet and comes with a one-car garage. The Lucía floor plan features an open kitchen with an island overlooking the living and dining area, with direct access to a private balcony. The primary suite includes a walk-in closet and in suite bath, and the building features a brick and stucco exterior. Included appliances are a double-door refrigerator, range, over-the-range microwave with exhaust fan, dishwasher, garbage disposal, washer and dryer. Seller concessions are available. Ask for details.

7446 Excitement Drive Unit 103, Kissimmee
1201 Wynstone Way, Kissimmee
$1,500,000
5 Beds ⋅ 5 Baths ⋅ O6455379 MLS
Located on a beautiful cul-de-sac in Reunion Resort’s Heritage Preserve neighborhood, this custom home sits on an oversized lot with nearly 140 feet of waterfront and beautiful conservation views. The recently expanded outdoor living area features a heated pool and spa, and a beautiful new turf lawn, providing plenty of space to relax and entertain while enjoying the Florida sunsets. Inside, you'll find an open two-story living area, an updated kitchen with Thermador appliances and quartzite countertops, and a spacious downstairs primary suite overlooking the pool. Two additional bedroom suites are upstairs, while a separate courtyard casita offers guest accommodations and a bunk and recreation room. An expansive bonus entertainment and game room provides even more space for recreation and gatherings. Primarily used as a second home, the property has been well maintained and features an active Reunion Club membership, offering access to three championship golf courses, a water park, tennis, pickleball, restaurants, and more. Just minutes from Walt Disney World!

1201 Wynstone Way, Kissimmee
473 Water Street Unit 473, Kissimmee
$369,000
2 Beds ⋅ 2 Baths ⋅ S5160843 MLS ⋅ 473 BLDG.
LOCATION, LOCATION, LOCATION! Just steps from Downtown Celebration! Enjoy the charm and convenience of Celebration living in this light and bright third-floor, 2-bedroom, 2-bath condominium located on desirable Water Street. Offering 1,261 square feet of living space, this inviting residence provides a comfortable layout with plenty of natural light and a welcoming atmosphere. The true highlight of this property is its exceptional location! Step outside and enjoy a short stroll to Downtown Celebration, where you'll find popular local restaurants, shopping, lakeside views & rocking chairs, and year-round community events. Enjoy the beautiful walking and biking trails, community pools, parks, and recreational amenities that make Celebration such a special place to call home. Whether you're looking for a full-time residence or a Florida getaway, this condo offers the opportunity to enjoy a low-maintenance lifestyle in the heart of one of Central Florida's most sought-after communities. Conveniently located near Walt Disney World, major highways, and Orlando's world-famous attractions. Leave the car behind and experience the Celebration lifestyle right outside your door! CLOSE BY THE END OF THE YEAR! TENANT LEASE ENDS DEC 31, 2026.

473 Water Street Unit 473, Kissimmee
7511 Northern Harrier Way Unit 107, Kissimmee
$455,500
3 Beds ⋅ 2 Baths ⋅ O6453808 MLS ⋅ 1 BLDG.
Under Construction. Discover The Crescent at Reunion Resort, where luxury living meets exceptional resort-style amenities! Located within Reunion Resort Golf & Club community, featuring three championship golf courses, this new construction condominium offers a unique opportunity for a primary residence, vacation home, or short-term rental investment. Enjoy beautifully designed interiors, modern finishes, and access to an exceptional resort lifestyle. An exclusive Reunion Resort membership is included with the deed, subject to applicable membership fees and terms. Attractive developer incentives are available, including closing cost assistance and special property management opportunities, with the first year of management fees waived through the designated program. Conveniently located near Walt Disney World, shopping, dining, and Orlando's world-famous attractions. Multiple floor plans and units available. Schedule your private tour today and discover everything The Crescent has to give

7511 Northern Harrier Way Unit 107, Kissimmee
2593 Maneshaw Lane, Kissimmee
$360,000
3 Beds ⋅ 3 Baths ⋅ O6455336 MLS ⋅ 001 BLDG.
YOUR DISNEY VACATION GETAWAY WITH INVESTMENT POTENTIAL! Welcome to 2593 Maneshaw Lane, an exciting opportunity to own a vacation home in the highly sought-after Windsor Hills Resort, one of the area's premier vacation communities just minutes from Walt Disney World! Featuring 3 bedrooms, 3 bathrooms, and your very own private pool, this inviting townhome offers the perfect combination of personal enjoyment, vacation convenience, and short-term rental potential. Imagine spending your mornings exploring the magic of Disney, your afternoons relaxing poolside in your own private retreat, and your evenings enjoying everything this incredible resort community has to offer. Windsor Hills takes the vacation experience to another level with an impressive array of resort-style amenities, including a spectacular zero-entry lagoon-style swimming pool, a heated spa, Sir Windsor's AquaVenture water park with exciting waterslides and splash pad, a fully equipped fitness center, clubhouse, arcade and game room, movie theater, children's playgrounds, tennis, basketball, pickleball, sand volleyball, and a putting green. The clubhouse also features a convenient Marketplace & Grill, making it easy to enjoy a relaxing meal or grab vacation essentials without leaving the resort. All within a 24-hour guard-gated community designed around the Central Florida vacation lifestyle! Whether you're searching for your own Disney-area vacation retreat, a property to enjoy with family and friends, or an investment opportunity with the flexibility to rent through short-term vacation rental platforms when you're away, this property offers an appealing combination of location, lifestyle, and versatility. Conveniently located near Walt Disney World, Disney Springs, shopping, dining, golf, and Central Florida's world-famous attractions, this is your opportunity to experience the magic of Windsor Hills for yourself. Own your piece of the vacation lifestyle and make every visit to Central Florida unforgettable!

2593 Maneshaw Lane, Kissimmee
8629 Cavendish Drive, Kissimmee
$605,000
4 Beds ⋅ 3 Baths ⋅ OM735362 MLS
Enjoy your own pool and room to spread out in this 4-bedroom, 2.5-bath home in Kissimmee’s Lindfields neighborhood. Currently used as an Airbnb, this two-story home offers 2,230 square feet of living space on a corner lot with no HOA. Inside, high ceilings, large windows, make the living areas feel bright and open. Marble-look tile floors add a modern touch, and the kitchen features stainless steel appliances and a breakfast bar overlooking the living room. There’s also a dining area nearby, so everyone can gather comfortably. The primary bedroom is on the first floor, and bathroom features include a freestanding soaking tub, a separate shower, and a double-sink vanity. Sliding glass doors open to the screened-in pool area, where you can enjoy your morning coffee, cool off after a day out, or spend time with friends. The fenced backyard offers privacy and green space beyond the pool enclosure. A two-car garage ( Play room ) and a location near Disney-area attractions round out the home. Whether you’re looking for an everyday home or a vacation getaway, this one is worth a visit!

8629 Cavendish Drive, Kissimmee
1531 Fairview Circle, Kissimmee
$710,000
5 Beds ⋅ 6 Baths ⋅ S5160774 MLS
Turnkey income opportunity in Patriots Landing at Reunion Resort! Built in 2023 and offered fully furnished, this 5-bedroom, 5.5-bath home with its own private pool delivers the space, layout and resort setting today's vacation-rental guests are looking for. At only three years old, it offers a relatively new roof, new kitchen appliances and a new air conditioning system - the big-ticket items are all recent — while giving investors and second-home buyers the advantage of newer construction and reduced near-term maintenance and repair concerns compared with older properties. With approximately 3,076 square feet of living space and all bedrooms featuring en-suite baths, the home is designed for groups who want comfort, privacy and room to gather. The open living areas flow to a private pool and outdoor entertaining space, creating the Florida vacation experience guests book again and again. A dedicated game room adds another guest-friendly amenity, while the fully furnished, lightly used interiors make this a true move-in / rent-ready offering with minimal upfront setup. Location is the revenue driver: Reunion places guests close to Walt Disney World and Orlando's world-famous theme parks, while also appealing to winter visitors seeking warm Florida sunshine and golf lovers drawn to the resort lifestyle. Whether used as a short-term rental investment, a second home with income potential when not in use, or a personal vacation retreat, 1531 Fairview Circle offers a rare combination of new-build efficiency, turnkey furnishings and strong vacation-home appeal.

1531 Fairview Circle, Kissimmee
1136 Celebration Avenue, Kissimmee
$879,000
4 Beds ⋅ 4 Baths ⋅ S5160860 MLS ⋅ 1136 BLDG.
Come and see this meticulously maintained and continually upgraded 4-bedroom, 3.5-bath ISSA-built townhome that offers over 2,800 square feet of elegant living across three stories in the heart of Celebration’s South Village. Built with solid block, this single-owner townhome radiates pride of ownership and is move-in ready. The interior features gleaming oak hardwood floors throughout, plantation shutters, wide baseboards, custom trim, wainscoting, and soaring 10-foot ceilings. The entire interior, including ceilings, was freshly painted in 2024. Major system updates include a new roof (2018), new water heater (2022), and two A/C systems (2020 and 2024) so all the hard work is done. The main level offers spacious open living and dining areas, complemented by a conveniently located half bath. The fully renovated kitchen overlooks the private, fenced courtyard and features quartz countertops, brand-new stainless steel appliances, breakfast bar seating, a separate eat-in area, updated lighting, and wine/beverage refrigerator. The kitchen flows seamlessly into the cozy family/gathering room, ideal for everyday living and entertaining. Upstairs, a signature oak staircase leads to a versatile home office/bedroom with frosted glass sliding doors, an additional bedroom, a full bath, and the primary suite. The primary suite offers park views, a huge custom walk-in closet, double raised vanities, a walk-in shower, and a large soaking tub perfect for when you want to wind down. A second oak staircase—hidden behind an elegant barn door—leads to the expansive third floor, featuring oak flooring, a full bath, and a large closet. This space is perfect for a home theater, entertainment area, or a 4th bedroom suite. Outdoor living is enhanced by a large fenced courtyard with mature landscaping and a brick paver patio, ideal for dining and grilling. A spacious two-car garage is accessed through the courtyard. The home has always been used as a vacation residence and has never housed pets, making it ideal for those seeking a pristine, allergy-friendly environment. Ideally situated directly across from Spring Park, residents enjoy access to a saltwater heated pool, state-of-the-art playground, and Heritage Hall for events and meetings. Centrally located, this home is just a short walk to community amenities, parks, shops, dining, and all that Celebration has to offer. This exceptional townhome offers the perfect balance of luxury, location, and livability—an opportunity not to be missed.

1136 Celebration Avenue, Kissimmee
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