Kissimmee/Celebration Homes with Gated Amenities

Kissimmee/Celebration Homes with Gated Amenities

Welcome to Kissimmee and Celebration, two enchanting communities nestled in the heart of Osceola County, Florida. Known for their vibrant atmosphere and proximity to world-renowned attractions, these areas blend the charm of small-town living with the excitement of urban conveniences.

Kissimmee, a gateway to the magic of Central Florida, is famous for its lush landscapes, stunning lakes, and a rich tapestry of cultural experiences. Just a stone's throw away, Celebration offers a picturesque setting with its beautifully designed streets, quaint shops, and delightful eateries, all inspired by traditional American small-town aesthetics. Whether you’re exploring the scenic parks or indulging in local cuisine, both communities provide a perfect backdrop for a fulfilling lifestyle.

For those seeking a sense of security and exclusivity, homes with gated amenities are a prominent feature in Kissimmee and Celebration. These properties offer not only luxurious living spaces but also peace of mind with their secure, gated entrances. Imagine coming home to a serene environment where you can unwind in beautifully landscaped gardens, take a stroll by the community pool, or enjoy recreational facilities tailored for an active lifestyle.

Gated communities in this region often boast a variety of amenities such as fitness centers, playgrounds, and clubhouses, fostering a true sense of community among residents. With easy access to major highways and proximity to theme parks, shopping, and dining, Kissimmee and Celebration present an extraordinary opportunity for those looking to invest in their dream home. Embrace the charm and security of these remarkable neighborhoods, where every day feels like a vacation!

Newest Kissimmee/Celebration Homes with Gated Amenities

$679,000
5 Beds ⋅ 5 Baths ⋅ Windsor Hills Ph 06 SubDv. ⋅ 34747 Zip Code
This well-maintained 5 bedroom, 5 bath home in the 5-Star Windsor Hills Resort offers buyers a rare opportunity to acquire a proven, income-producing short-term rental just minutes from Walt Disney World—one of the strongest and most reliable vacation-rental corridors in the United States. Designed with the resort’s most desirable 5-bedroom open floorplan, the home consistently attracts large families and multi-generational groups, maximizing both occupancy and nightly rate potential. For buyers seeking immediate continuity of income, the seller is willing to transfer future bookings, allowing a seamless transition with no downtime. Interior Features for High-Demand Guest Use Multiple dining areas and a spacious main living room built to accommodate high guest volume Stainless steel appliances in the kitchen Two ground floor ensuites plus an additional twin bedroom—ideal for multi-family bookings Two junior suites upstairs, each with a private bath, supporting strong guest satisfaction and repeat stays Converted garage game room with foosball and pool tables—an amenity that significantly boosts rental performance Outdoor & Resort Amenities The screened lanai features a private heated pool, a top-performing feature for year-round bookings. Windsor Hills remains one of Central Florida’s top-performing vacation rental communities, offering: Lagoon-style resort pool Clubhouse, fitness center, and marketplace Tennis, racquetball, basketball, and volleyball Theater, arcade, playgrounds, and putting greens 24-hour guarded security Its unmatched proximity to Disney drives consistent occupancy, premium nightly rates, and strong year-round demand. Investment Highlights This property represents a rare chance to acquire a low-maintenance, high-demand, income-generating asset in one of the region’s most reliable STR markets. Windsor Hills is a purpose-built resort community offering amenities for all ages while remaining less than five minutes from Walt Disney World—making it an ideal choice for families and groups seeking affordable luxury in a prime location.

7777 Teascone Boulevard, Kissimmee
$648,800
5 Beds ⋅ 5 Baths ⋅ Solara Resort SubDv. ⋅ 34747 Zip Code
Welcome to this exceptional home in Solara Resort. This is a rare opportunity! Although located in one of Orlando’s most sought-after short-term rental communities, this home has never been used as a vacation rental. It has had only one owner and has been enjoyed exclusively by the same family since it was built. The home has been very well cared for and remains in outstanding condition. The first floor features a large suite, perfect for the owners or guests. Upstairs, there is a loft that can be used as a media room, game room, or family lounge, plus another spacious suite and three additional bedrooms. Two of the bedrooms share a convenient Jack and Jill bathroom. Offered fully furnished and move-in ready, this home is located just minutes from Walt Disney World, Universal Orlando, shopping, dining, and entertainment. Solara Resort offers great amenities including a clubhouse, resort-style pool, splash park, FlowRider® surf simulator, fitness center, sports courts, playgrounds, restaurant, café, and 24-hour gated security. Perfect as a primary residence, vacation home, or investment property with excellent short-term rental potential.

9083 Sunshine Ridge Loop, Kissimmee
$3,199,999
11 Beds ⋅ 13 Baths ⋅ Reunion West Vlgs North SubDv. ⋅ 34747 Zip Code
Welcome to an exceptional luxury estate located within the prestigious Reunion Resort, where sophisticated design, expansive living spaces, and resort-style entertainment come together to create an extraordinary Central Florida retreat. Spanning three thoughtfully designed levels, this impressive 11-bedroom, 11-bath residence has been curated for both luxurious everyday living and the highly desirable vacation rental market. The main level welcomes you with beautifully appointed living and dining spaces anchored by a spacious gourmet kitchen designed for entertaining. An impressive game room offers skeeball, basketball, air hockey, arcade games and shuffleboard, while multiple gathering areas throughout the home provide plenty of space for guests to relax and entertain. Step outside to your private resort-style pool and spillover spa surrounded by generous patio space, outdoor seating and a built-in barbecue—creating the perfect setting for enjoying Florida's year-round sunshine. Entertainment continues throughout the upper levels with a dedicated movie theater featuring reclining theater seating, fitness area, playroom, billiards room, dual gaming stations and multiple screened balconies. The home's extensive bedroom configuration includes multiple king suites along with imaginative themed bunk rooms, offering exceptional flexibility for large families and vacationing groups. Located within Reunion Resort's sought-after Legends Corner neighborhood, the property combines privacy with convenient access to the world-class attractions, dining, golf and entertainment that make the Orlando area one of the world's premier vacation destinations. Whether envisioned as an impressive personal retreat, second home or luxury vacation-rental investment, this remarkable Reunion estate delivers the space, amenities and entertainment today's resort buyer is looking for—all in one unforgettable property.

550 Muirfield Loop, Kissimmee
$325,000
2 Beds ⋅ 2 Baths ⋅ Reunion Grande Condo SubDv. ⋅ 34747 Zip Code
**LIMITED-TIME LAUNCH PRICING — secure this Reunion Grande residence at its introductory price before it returns to market-value pricing after Week 3!** Welcome to Unit #307, a fully furnished 2-bedroom, 2-bath residence offering one of the most compelling features in Reunion: direct, unobstructed views toward Walt Disney World from your own private balcony, where you can take in spectacular Florida sunsets and nightly Disney fireworks. Offering approximately 1,430 square feet, the residence features an open and inviting floor plan with upgraded finishes, crown molding, granite countertops, and a kitchen that flows seamlessly into the living and dining areas. The split-bedroom configuration creates two private bedroom suites with well-appointed bathrooms, making the layout equally suited for personal use, vacationing, or hosting guests. Offered fully furnished and turnkey, #307 is positioned for immediate enjoyment and offers the flexibility of primary, second-home, or vacation-rental use. An active Reunion Resort membership is included and transferable to the new owner, providing access to Reunion's renowned resort lifestyle, including three signature golf courses designed by Arnold Palmer, Tom Watson, and Jack Nicklaus, the multimillion-dollar water park, resort pools, tennis and pickleball, fitness facilities, and additional amenities. Within the Reunion Grande itself, enjoy front desk concierge service, valet parking for members, 7593 Chophouse, a lobby-level sushi bar, Starbucks coffee and gift shop, plus the rooftop restaurant and pool overlooking the surrounding resort and Central Florida skyline. Located just minutes from Walt Disney World and convenient to Orlando's other world-famous attractions, #307 combines location, flexibility, resort amenities, and a view that is difficult to replicate. **With launch pricing available for only the first three weeks, this is the opportunity to act before the property returns to market value.**

7593 Gathering Drive Unit 307, Kissimmee
$325,000
2 Beds ⋅ 2 Baths ⋅ Reunion Grande Condo SubDv. ⋅ 34747 Zip Code
**LIMITED-TIME LAUNCH PRICING — take advantage of this introductory price before the property returns to market-value pricing after Week 3!** Welcome to Unit #706 at the Reunion Grande, an exceptional opportunity to own a fully furnished, turnkey 2-bedroom, 2-bath residence in the heart of Reunion Resort. Positioned on the 7th floor with desirable east-facing exposure, this spacious 1,430-square-foot condo offers beautiful morning light, elevated resort views, and comfortable shaded afternoons from your private balcony. Inside, an open-concept layout connects the kitchen, dining, and living spaces, while the split-bedroom design provides privacy for owners and guests alike. Offered fully furnished and ready for immediate enjoyment, this residence offers tremendous flexibility as a primary residence, second home, vacation retreat, or short-term rental opportunity. Located inside the iconic Reunion Grande, owners and guests are surrounded by resort-style conveniences including valet parking, front desk concierge service, on-site dining, Starbucks coffee and gift shop, the acclaimed 7593 Chophouse, sushi bar, and an 11th-floor rooftop restaurant and pool offering panoramic views across Central Florida. Beyond the Grande, Reunion Resort encompasses approximately 2,300 acres and is home to three signature championship golf courses, resort pools, dining, fitness and recreation opportunities, and its multimillion-dollar water park. Best of all, you're approximately 6 miles from Walt Disney World with convenient access to Orlando's world-famous attractions and major highways. Whether you're looking for your own Central Florida getaway or a furnished property with vacation-rental flexibility, #706 delivers the location, lifestyle, and versatility Reunion is known for. **The launch price is available for a limited three-week window — don't wait for the price to return to market value.**

7593 Gathering Drive Unit 706, Kissimmee
$350,000
Reunion West Village 3a SubDv. ⋅ 34747 Zip Code
Build your dream home in the prestigious Reunion Resort! This homesite offers a fantastic location within the community, surrounded by beautiful luxury homes and just steps from Reunion’s renowned golf courses. Enjoy the opportunity to design a custom residence or vacation retreat in one of Central Florida’s premier resort communities, conveniently located near Walt Disney World, dining, shopping, and Orlando’s world-class attractions.

1006 Coyote Creek Way, Kissimmee
$695,000
6 Beds ⋅ 4 Baths ⋅ Windsor Hills Ph 3 SubDv. ⋅ 34747 Zip Code
TURNKEY VACATION RENTAL INVESTMENT MINUTES FROM DISNEY WORLD! This beautifully decorated and totally renovated 6-bedroom, 3.5-bath single-family home is located in the highly desirable Windsor Hills Resort—one of the closest vacation home communities to Walt Disney World. Designed to stand out in the competitive vacation rental market, this home is being offered turnkey and is ready for its next owner and guests. The updated interior features stylish décor, granite countertops in the kitchen and bathrooms, and fun Star Wars-themed bedrooms that are sure to be a hit with younger guests. Outside, enjoy a south-facing private pool with no rear neighbors, providing excellent sun exposure and added privacy. One of the home's standout features is the poolside theater, allowing guests to watch movies, sports and TV while relaxing in or around the pool. The converted garage has been transformed into a fun, air-conditioned game room, adding another guest-favorite amenity and entertainment space. Location within the resort is another major advantage. The home is just a short 3-block walk to the Windsor Hills clubhouse, resort pool and water park. With its combination of location, renovations, privacy, themed bedrooms and guest-focused amenities, this property offers an outstanding opportunity for buyers seeking a turnkey Disney-area vacation home and short-term rental investment.

2630 Dinville Street, Kissimmee
$166,000
Reunion Ph 02 Prcl 01 & 1a SubDv. ⋅ 34747 Zip Code
Amazing opportunity to own a fantastic lot on the 3rd hole of the Palmer signature golf course. Land is hard to come by in Reunion these days so purchase while you can. The homesites do not have a time restriction to begin construction immediately so purchase now or for future generations to own. Build for full time residence or vacation home. Great proximity to all the major theme parks especially WALT DISNEY WORLD being just 2 exits away, makes this vacation community a top choice for visitors of all ages. If you are looking to take a few golf swings while on your vacation you can take the challenge on any of the 3 World Class Championship GOLF COURSES designed by Arnold Palmer, Tom Watson And Jack Nicklaus that are located on-site. Reunion offers many onsite restaurants from hamburgers at The Cove to fine dining at Chophouse and everything in between. There are 14 pools in the community including MULTIMILLION DOLLAR WATER PARK with lazy river & water slide.

7632 Excitement Drive, Reunion
$299,900
3 Beds ⋅ 3 Baths ⋅ Reunion Ph 1 Prcl 2 SubDv. ⋅ 34747 Zip Code
Virtually Staged. **Reunion Club Membership Available** Welcome to Carriage Pointe, located within the renowned guard-gated community of Reunion Resort. This beautifully renovated 3-bedroom, 2.5-bath townhome offers a truly exceptional combination of luxury, style, and modern design, complete with an attached 1-car garage. Completely renovated is an understatement, over $100,000 was invested into transforming this home from the studs up, with no detail overlooked. From the moment you enter, you’ll notice the luxury vinyl plank flooring that flows throughout the entire home, creating a sleek and cohesive feel. The heart of the home is the brand new open concept chef’s kitchen, featuring a large island, new appliances, and beautiful granite countertops. The contemporary upgrades continue upstairs, where custom under stair accent lighting adds a upscale touch, while the stunning cable railing system enhances the modern aesthetic. The spacious primary suite offers a private retreat with its own balcony and a beautifully remodeled en-suite bathroom featuring new cabinetry, quartz countertops, and an upgraded rainfall shower. Two additional bedrooms are located upstairs and share a second fully remodeled bathroom. With extensive renovations, high-end finishes, and a modern contemporary design throughout, this Carriage Pointe townhome is truly move-in ready and offers the opportunity to enjoy the exceptional lifestyle of Reunion Resort. Reunion Resort is a luxury resort, that also allows short term rental, and is a top choice for visitors of all ages, Reunion features 12 Pools In The Community, Including a multimillion dollar water park, Complete with a lazy river, splash park for the little ones, tiki bar, & Water Slides, 3 championship golf courses, 5 restaurants, tennis/pickleball courts, putt putt golf, and many more amenities, making Reunion truly a city within gates. This townhome is turnkey, and has so much more to see, that you will have to see in person to appreciate. It is now your turn to call Reunion Resort your new home, or home away from home, welcome home!

815 Assembly Court, Kissimmee
$590,000
7 Beds ⋅ 5 Baths ⋅ Emerald Island Resort SubDv. ⋅ 34747 Zip Code
Welcome to Emerald Island Resort, a gated and guarded vacation community located just minutes from Walt Disney World! This property has a very good rental history, ($81,080.40 in 2025) & ($60,097.00 ytd in 2026). This spacious 7-bedroom, 4.5-bathroom home offers the perfect combination of a turnkey short-term rental investment, second home, or full-time Florida residence. Situated on a private conservation lot, the home features a large south-facing heated private pool and spa, extended sundeck, spacious covered lanai, and peaceful conservation views. The open floor plan includes a large kitchen with island, granite countertops and stainless steel appliances, three king-size bedroom suites, themed bedrooms, and a garage converted into a fully air-conditioned game room. The home is being sold fully furnished and is ready for immediate use or continued vacation rental operation. For investors, the property offers the opportunity to assume the existing future bookings, representing upwards of $30,000 in rental revenue, providing an immediate head start for the new owner. Recent improvements include a roof replacement in 2022, a full interior and exterior paint refresh in 2023, resolution of a prior A/C issue in 2026, and a newly replaced pool pump and air blower. Additional features include laminate flooring, updated window treatments, pool/spa heater, and updated upstairs and downstairs A/C systems. Emerald Island Resort offers an exceptional location and resort lifestyle, surrounded by conservation areas and conveniently located near Disney, restaurants, shopping and Central Florida’s major attractions. Owners and guests enjoy access to an impressive array of amenities, including a clubhouse, sauna, fitness center, resort pools and spas, food court and bar, tennis, basketball, volleyball, miniature golf, children’s play areas, walking trails and more. The clubhouse is approximately a 7-minute walk from the home. Whether you’re looking for a proven vacation rental opportunity, a family retreat, or a permanent Florida residence, this beautifully maintained and fully furnished home offers flexibility, privacy, resort amenities and an unbeatable location near the area’s world-famous attractions. Schedule your private showing today!

8452 Secret Key Cove, Kissimmee
$654,900
7 Beds ⋅ 6 Baths ⋅ Emerald Island Resort Ph 4 SubDv. ⋅ 34747 Zip Code
Turnkey short-term rental home, minutes to Disney! Discover a rare opportunity to own this stunning 7 bedroom, 6 bathroom pool home in the sought after Emerald Island Resort. Boasting the largest layout in the community at 3,667 sq. ft., this home is perfectly suited as a vacation getaway, income-generating investment, or forever family home. Enjoy unparalleled waterfront views framed by lush wooded backdrops, creating a serene and private retreat. The expansive screened lanai, which spans the length of the house, features a partially covered area ideal for year round entertaining. Relax by the sparkling South facing private pool and spa and take in the ultimate Florida lifestyle. Step inside to find a well designed floor plan with ample living space, ideal for families or hosting guests. The stylish kitchen is a chef’s dream with abundant cabinet and countertop space, a breakfast bar, and a breakfast nook overlooking the huge living room and pool, your new favorite spot for morning coffee or casual dining. The main floor also features two bedrooms, a formal dining room and the charming “Harry Potter” closet for extra fun and storage. The upper level is thoughtfully divided by two staircases. One leads to a loft sitting area and three themed bedrooms and the other leads to two additional themed bedrooms, all designed for comfort, as five of the bedrooms feature en-suite bathrooms, while the remaining two share a convenient Jack and Jill bath. The 3 car garage has been transformed into an entertainment haven with air conditioning, complete with a mini movie theatre (seating for 8) and a game room with a pool table. Updates include: A brand new roof (11/24), a new pool heater (04/24), newer exterior paint (01/22) and a newer A/C and heat pump (11/20), replumbed A/C lines (2024) and spa actuators replaced (2024). As part of this premier gated community, you’ll enjoy access to an impressive clubhouse with a resort-style pool, Tiki bar, fitness center, sauna, and sundry shop. Other amenities include tennis and pickleball courts, volleyball, basketball, bike rentals, and 11 acres of natural walking trails. The prime location is conveniently located near Orlando’s major attractions, including theme parks, outlet shopping, restaurants, Promenade at Sunset Walk, and Island H2O Live! water park. This home comes fully furnished and equipped with a strong rental history, ready to generate income as a short term rental or provide your family with a wonderful retreat. Schedule your tour today and experience the ultimate Florida lifestyle in this stunning property.

8557 La Isla Drive, Kissimmee
$415,000
5 Beds ⋅ 5 Baths ⋅ Windsor At Westside Ph 1 SubDv. ⋅ 34747 Zip Code
Where else can you live in Florida feeling like you are on Vacation everyday?! Resort style pools, Lazy River, Water Playground, Fitness Center, Restaurant & Club House, Pond and Pier and so much more! Those are just the amenities; lets talk about this 5 Bedroom & 5 Bath with a private garage in paradise. You have enough space for the family and some including a theatre area for all to enjoy. Subtle taste of Disney throughout the home and a very nice size kitchen for all to gather. Don't want to stop the fun from the community pool? Well bring it home since you'll have your very own private pool and patio area to enjoy. Its spacious, its clean and comes completely furnished as you see it all you need is the key to make it yours. You can enjoy this home as little or as much as you'd like as short term rental is allowed as well as long term if you'd choose. Want the best of both worlds? Why not leave your vehicle stored in the garage and some personal items in your very own, owners closet's throughout the house. Having too many options is never a bad thing when you either way you are making the right choice. Schedule your next appointment today!

9025 Rhodes Street, Kissimmee
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