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

BUILD YOUR DREAM HOME IN REUNION! Exceptional opportunity to own a vacant homesite in one of Central Florida's most recognizable luxury resort communities. Located at 7453 Excitement Drive, this approximately 7,405 SF lot offers the chance to design and build a custom residence in an established neighborhood surrounded by impressive luxury homes. LOCATION IS EVERYTHING! Reunion is ideally positioned within the highly desirable Kissimmee/Orlando vacation corridor, offering convenient access to Walt Disney World, world-class attractions, shopping, dining, entertainment and major Central Florida roadways. Whether you're envisioning a luxury vacation home, second residence, primary home or investment property, this homesite provides an exciting opportunity to build rather than compromise on an existing property. Create the floor plan, finishes and outdoor living spaces that fit your vision while taking advantage of an established resort-community setting. This is an opportunity to secure your piece of Reunion and become part of an area known for its beautiful homes, resort atmosphere and exceptional Central Florida location. Bring your builder, bring your plans and imagine the possibilities at 7453 Excitement Drive! Bring Your Offers to Secure This Rare Corner Lot Opportunity!

7453 Excitement Drive, Kissimmee

3 Beds ⋅ 3 Baths ⋅ O6433292 MLS ⋅ Na BLDG.

Fully furnished and beautifully decorated 3-bedroom townhome in Regal Oaks at Old Town, a gated resort community where short-term rentals are permitted, just approximately 3 miles from the entrance to Walt Disney World. This two-story home features a spacious screened patio overlooking a wooded area, offering exceptional privacy and a peaceful setting for relaxing or entertaining. It offers 3 bedrooms and 2.5 baths. The open-concept main level features a granite kitchen with wood cabinetry and stainless-steel appliances, flowing into the dining and living areas. Sliding glass doors open to a screened lanai with a private hot tub, an upgraded feature beyond the standard unit in the community. A convenient half bath completes the first floor. The home features durable hard-surface flooring throughout with no carpet, and the interior was freshly painted in 2025. Upstairs, the primary suite includes a private bath with dual sinks, while two additional bedrooms share a second full bath. A full-size washer and dryer are also included. Owners and guests enjoy access to the extensive Regal Oaks resort amenities, including multiple pools with water slides, a spa, poolside bar, on-site restaurant and market, fitness center, tennis courts, game room, and gated entry. Currently operating as a short-term rental with an established booking history, the property is offered fully turnkey. The sale includes furniture, televisions, wall art, mirrors, décor, linens, towels, cookware, dinnerware, small appliances, and the existing appliances, washer, and dryer. The buyer may continue the existing rental operation, use the home as a personal vacation property, occupy it directly, or enjoy a combination of personal use and rental income. Prime location near Orlando's top attractions: Old Town adjoins the community, Fun Spot is approximately 0.5 mile away, Publix is about 1.2 miles, Celebration and Super Target approximately 3 miles, Premium Outlets approximately 7 miles, SeaWorld approximately 8.5 miles, and Universal Orlando approximately 12 miles. Sold as-is with right to inspect. Buyer and buyer's agent to independently verify all room dimensions, square footage, HOA fees, lease and rental restrictions, and regulations, etc.

5710 Olga Street, Kissimmee

3 Beds ⋅ 3 Baths ⋅ O6434033 MLS

Welcome to your Reunion retreat! This beautifully maintained 3- Bedroom, 2.5 bath home located in the highly sought after Reunion resort community. The property offers an inviting open-concept floor plan, a private pool and peaceful pond view front from master room and front of the property. Imagine the lifestyle with convenient access to golf, dining, recreation and major central Florida attraction.

7766 Linkside Loop, Kissimmee

2 Beds ⋅ 2 Baths ⋅ S5155426 MLS

2 Bed / 2 Bath Ground-Floor Villa in the Heart of Kissimmee To see it is to buy it. This beautifully updated villa blends comfort, style, and unbeatable location. Step into a bright, inviting space featuring a fully remodeled kitchen with modern finishes, perfect for cooking, hosting, or simply enjoying your morning coffee. The ground-floor layout offers easy access and seamless living, with two spacious bedrooms and two well-appointed bathrooms designed for convenience and privacy. Two dedicated parking spots right at your doorstep Located in the heart of Kissimmee, you’ll be just minutes from shopping, dining, entertainment, and major attractions. The community is peaceful, well-maintained, and ideal for both homeowners and investors.

2207 Caribbean Drive, Kissimmee

3 Beds ⋅ 3 Baths ⋅ S5155726 MLS ⋅ Na BLDG.

Great investment opportunity in the highly sought-after Regal Oaks Resort, a gated community ideally located near Central Florida’s world-famous attractions. This fully furnished 3-bedroom, 2.5-bath luxury townhome offers an open-concept floor plan designed for both comfort and vacation living.The main level features a spacious living and dining area, a well-appointed kitchen with granite countertops, and a convenient powder room. Sliding glass doors lead to a private screened-in lanai featuring a heated spa and sun loungers, creating the perfect space to relax and enjoy the Florida lifestyle.Regal Oaks offers an impressive selection of resort-style amenities, including a state-of-the-art clubhouse, resort pools with dueling water slides, poolside bar and snack bar, cabanas, restaurant and lounge, fitness center, tennis court, and convenience store. HOA services include cable TV, internet, exterior and grounds maintenance, pest control, guard-gated entrance, and valet trash.The community allows short-term rentals and may also be enjoyed as a second home or primary residence, offering excellent flexibility for owners. With its desirable location and strong appeal among vacation guests, this property presents an excellent opportunity to own a fully furnished home in one of the area’s most popular resort communities.

2774 Corvette Lane, Kissimmee

6 Beds ⋅ 5 Baths ⋅ S5155604 MLS

Welcome to 1517 Mumbai Way, a spacious and beautifully positioned 6-bedroom, 4.5-bathroom pool home in the highly sought-after Windsor at Westside community! Built in 2019 and offering approximately 3,142 square feet of living space, this impressive two-story residence provides the perfect combination of comfort, space, and Florida resort-style living. Step inside to discover an open and inviting layout designed for both everyday living and entertaining. With six bedrooms and four-and-a-half bathrooms, there is plenty of room for family, guests, or hosting larger groups. The home also features a private screened-in pool and spa, creating your own relaxing outdoor retreat for enjoying Florida's year-round sunshine. A two-car garage, spacious living areas, walk-in closets, stone countertops, ceramic tile flooring, and a thoughtfully designed floor plan add to the home's functionality and appeal. Located in Windsor at Westside, residents can enjoy the lifestyle of a resort-style community while being conveniently positioned in the heart of the Kissimmee/Orlando vacation corridor. Whether you're looking for a full-time residence, a second home, or an investment property, this home offers an exceptional opportunity to own a spacious Florida property in a popular destination. Come experience the space, privacy, and resort-style lifestyle that make 1517 Mumbai Way a property worth seeing!

1517 Mumbai Way, Kissimmee

4 Beds ⋅ 4 Baths ⋅ O6433983 MLS

This beautifully maintained 4-bedroom, 4-bathroom pool home offers the perfect blend of comfort and income potential, whether you’re looking for a second home getaway or a turnkey short-term rental investment. Located just steps from the community clubhouse, this Mediterranean-style home welcomes you with a charming tile roof, arched entryway, and a two-car garage. Step inside to an open-concept living space filled with natural light, featuring tile flooring throughout the main living areas, a stylish neutral palette, and a spacious living room that flows seamlessly into the dining area and kitchen — perfect for entertaining. The kitchen boasts white cabinetry, granite countertops, and a breakfast bar with seating for four. The luxurious primary suite is a true retreat, showcasing a plush tufted velvet bed frame, designer artwork, and an en-suite bath. Three additional bedrooms and three more full baths provide ample space for family and guests. Out back, unwind in your private screened-in pool and spa oasis, surrounded by lush greenery and mature trees for added privacy — ideal for year-round Florida relaxation. Located in the sought-after Veranda Palms community, residents enjoy resort-style amenities including a clubhouse, pool, and more — all just minutes from Orlando’s world-famous theme parks, shopping, and dining. Don’t miss this incredible opportunity — schedule your showing today!

2658 Tranquility Way, Kissimmee

4 Beds ⋅ 3 Baths ⋅ O6428133 MLS

POOL HOME WITH 4 BED AND 3 BATH, ABUTS TO WOODS AND POND, NEWLY RENOVATED, SOLID COUNTER TOP. KITCHEN CABINET, NEW BATHROOOMS. THIS HOUSE IS IN CLOSE PROXIMITY TO AIRPORT, THEME PARKS, THE LOOPS, GROCERY SHOPPING AND ACCESS TO MAJOR HIGHWAYS.

3119 Fairfield Drive, Kissimmee

3 Beds ⋅ 3 Baths ⋅ O6433933 MLS ⋅ 123 BLDG.

Turn Key Townhouse in Guard-Gated Terra Verde — Minutes from Disney Whether you're searching for a vacation getaway, a short-term rental investment, or your next home, this fully furnished townhouse at 123 Pompano Beach Dr delivers. Nestled in the 24-hour guard gated resort community of Terra Verde, you're just minutes from Disney, Orlando's theme parks, and a wealth of nearby dining, shopping, and hospitals. Step inside to an open, airy floor plan with ceiling fans throughout — keeping the home comfortable year-round. The combined living and dining space flows effortlessly for both everyday living and entertaining, while the kitchen's cozy eating nook is ideal for casual meals. Upstairs, the primary bedroom offers a private retreat tucked away from the main living areas. Life in Terra Verde means resort-style amenities at your doorstep: a fitness center, community pool, sauna, hot tub/spa, clubhouse, tennis courts, volleyball court, movie theater, and more. Stay active or unwind by the pool — this community truly has it all. Don't miss your chance to own a slice of Kissimmee paradise. Schedule your private showing today!

123 Pompano Beach Drive, Kissimmee

Exceptional opportunity to build in one of the most desirable locations within Reunion Resort. This golf-front homesite in the established Homestead neighborhood overlooks the Tom Watson Signature Golf Course and is ideally positioned close distance to the Reunion Grande, Golf Clubhouse, Seven Eagles Pool Pavilion, dining and more. The 55' x 125' homesite offers the perfect setting to design and build your own custom residence, vacation home or investment property while enjoying beautiful golf course views and easy access to the heart of the resort. Reunion Resort is one of Central Florida's premier gated golf communities, featuring three Signature golf courses designed by Arnold Palmer, Tom Watson and Jack Nicklaus, along with an impressive collection of resort amenities. Located just minutes from Walt Disney World with convenient access to I-4 and SR 429. With its golf-front setting, established neighborhood and proximity to Reunion's main resort amenities, 1221 Radiant offers a combination of location and views that is becoming increasingly difficult to find.

1221 Radiant Street, Kissimmee

3 Beds ⋅ 3 Baths ⋅ S5155482 MLS ⋅ Q BLDG.

Virtually Staged. Welcome to Seven Eagles at Reunion Resort! This beautifully updated 3-bedroom, 3-bath condo offers a unique and flexible floor plan ideal for multi-generational living, shared living, or those looking to generate rental income while maintaining their own private space. With two bedrooms on the first floor and the main living area upstairs, the layout provides the opportunity to live upstairs while renting or sharing the downstairs space. The home features luxury vinyl plank flooring throughout, fresh interior paint, a bright open-concept living area, and a refreshed kitchen with refinished cabinetry. Appliances, including the washer and dryer, were replaced in 2023. Additional upgrades include a 2023 tankless water heater and replaced upstairs A/C system. Upstairs, enjoy private balconies overlooking a peaceful, tree-lined walkway shaded by mature landscaping. The walkway offers convenient access to the community pool, tiki bar and fitness center, adding to the relaxed resort-style setting. Downstairs, enjoy two private covered porches—one in the front and one in the back, offering additional outdoor spaces to relax. Located in the heart of Reunion Resort, residents enjoy an impressive selection of amenities including multiple community pools, clubhouse, fitness center, restaurant, tennis courts, playgrounds, dog park and gated 24-hour security. Cable, internet, water, sewer, exterior and grounds maintenance are also included. Flexible lease terms and short-term leases are allowed, making this an excellent option for relocation, extended stays, multi-generational households or shared living arrangements. Conveniently located near Disney, shopping, dining and Central Florida’s major attractions.

7510 Seven Eagles Way, Kissimmee

3 Beds ⋅ 2 Baths ⋅ O6433899 MLS ⋅ 3226 BLDG.

Welcome home to the beautiful, established community of Shadow Bay! This delightful 2-story condominium offers the perfect blend of comfort, style, and unbeatable convenience. Boasting 3 spacious bedrooms and 2 full bathrooms across 1,375 square feet of functional living space, this home is designed to impress. The highly sought-after floor plan features a private primary bedroom suite on the main level, complete with its own full bathroom. Upstairs, you will find two additional bright and airy bedrooms, perfect for family, guests, or a dedicated home office. Enjoy low-maintenance Florida living just minutes away from premier shopping centers, popular dining districts, local schools, and major highways for an easy commute. Schedule your private viewing today and make this cozy home your new residence.

3226 Rio Grande Trl Unit 3226, Kissimmee

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