House holiday rentals in Kissimmee

A compact kitchen features white cabinetry and modern stainless steel appliances. An electric stovetop is positioned beside a microwave, with a coffee maker and various kitchen utensils visible. A small refrigerator stands nearby, complemented by decorative items on the open shelves.

4.99 out of 5 average rating, 150 reviews

Private Suite with Independent Entrance

Private Suite with Independent Entrance Kissimmee, Fl Enjoy a modern and fully equipped private suite, perfect for couples or travelers looking for comfort, privacy, and a relaxing stay just minutes away from Orlando’s top attractions. 📍Perfect Location Conveniently located in Kissimmee, just minutes from: 🎢 Disney World 🎬 Universal Studios 🌊 SeaWorld and Aquatica You’ll also find restaurants, supermarkets, outlets, and gas stations nearby an excellent location for your Orlando vacation!

4.87 out of 5 average rating, 261 reviews

The villa features a modern exterior with a sloped roof and a two-car garage. Palm trees are landscaped around the front yard, which is bordered by well-maintained grass. A clear blue sky provides a bright backdrop to the welcoming entrance.

Home

3 bedroom Villa in Kissimmee

The villa is in a residential area within a 5-min drive to local amenities including, a pharmacy, 3 supermarkets and 2 gas stations. The property is between 15 - 40 mins drive from Disney, Epic Universe, SeaWorld, Gatorland & Universal Studios. Orlando International Airport is only about 17 mins drive away. Osceola Heritage Park, the home of the world’s largest collector car auction is only 4 mins drive from the villa. The Florida Turnpike that runs through Miami is 6 mins from the property.

A private pool area features a crystal clear pool with a built-in spa, surrounded by a screened enclosure. A spacious patio is equipped with lounge chairs, a dining set, and a barbecue grill, offering a relaxed outdoor environment.

4.95 out of 5 average rating, 136 reviews

Vacation Home 3 bedroom/2 full bath/private pool

Bring the whole family to this great place with lots of room for fun. This house is perfect for you, your family, and friends! Spacious 3 bedrooms and 2 full baths that can accommodate up to 9 people. The house is fully air conditioned and has a pool. Indoor entertainment such as board games, ping pong table and TV cable. Please note smoking or parties are NOT allowed in house premises. No pool heater available during May through October. **You also MUST be 21 or older to rent this property**

4.77 out of 5 average rating, 339 reviews

Free Waterpark! Fantasy World - Fun at BnB

Experience magic at our Fantasy World Villas retreat, minutes from Disney, Universal & Sea World. This modern 2-bed villa boasts a Mickey-themed room, king-size bed in the master, full kitchen, laundry, private patio, free Wi-Fi & parking. Resort amenities include heated pools, hot tubs, lazy river, water slides, tiki bar, gym, playground, sports courts, and more. Enjoy nearby restaurants & grocery stores. Create unforgettable memories in this captivating home away from home! Book Now!

4.92 out of 5 average rating, 103 reviews

The dining area features a modern table set with grey chairs, adorned with red napkins and dishes. A large mural of Mickey Mouse adds a playful touch to the wall. The kitchenette, equipped with sleek white cabinets and appliances, is visible in the background.

Home in Four Corners

Mickey and Donald

The Mickey and Donald house was decorated with joy and friendship in mind, mainly featuring Mickey, Minnie, Donald, and Daisy. Each area of the house is cute, stylish, and fun; Some of the highlights include the adorable Donald and Daisy bedroom, and the gorgeous Mickey Mouse mural in the dining area.There’s something for everyone in the family in this vibrant house that is sure to make for many happy vacation memories, also a equipped kitchen, laundry and free access to 2 clubhouses.

The exterior of the house is viewed from the sidewalk, surrounded by neatly maintained lawns. Two large trees provide ample shade. The home features a light-colored facade and a driveway visible on the right, complemented by a two-car garage.

4.86 out of 5 average rating, 118 reviews

Harmony Place - W/ Pool - Near Walt Disney

Welcome to Harmony Place, your perfect getaway! Relax and unwind with the whole family at this serene retreat. This stunning home features a private pool, 3 spacious bedrooms, and 2 bathrooms, comfortably accommodating up to 9 guests. Located in the exclusive Crescent Lakes community in Kissimmee, Florida, you’ll be just 11 miles from Walt Disney World, 22 miles from Universal Studios, and 18 miles from SeaWorld Orlando. Enjoy nearby dining and shopping options for added convenience!

A sunny pool deck features a private pool surrounded by a screened enclosure. Four chaise lounge chairs are positioned near the pool, alongside a covered area with a table and chairs for outdoor dining.

4.96 out of 5 average rating, 160 reviews

Large House | Near Disney | Private Pool | 6 beds

Modern, clean and comfortable designs welcome you as you walk into this gorgeous updated 4 bedroom, 2,800 sq. ft. house. Enjoy the open feel the corner lot offers. A perfect getaway for families and friends with Disney only 5 miles away! Relax in the sun, splash in the private pool, or chill in the updated game room. Located in the beautiful Veranda Palms gated community where you can enjoy the heated community pool, hot tub, water park, splash pad, and gym within a 3 minute walk!

The exterior of the home showcases a single-story structure with a combination of pastel hues and stone accents. Lush green grass surrounds the building, accompanied by a variety of tropical plants and a palm tree. A well-maintained driveway leads to a two-car garage.

4.88 out of 5 average rating, 130 reviews

Relaxing Orlando 4 BR home, pool & water view

Charming home just 10-20 miles away from Disney World, SeaWorld, and Universal Studios, owned by Kim & Shawn Beus. Tranquil neighborhood with walking/running pathways. It is just 10 minutes away from many restaurants, grocery, shopping, and entertainment options like Medieval Times, Fun Spot America, and Give Kids the World. Relax in the private screened in pool (heated for additional fee) and patio and watch birds play in the pond.

An outdoor area with a screened enclosure showcases a private pool surrounded by a well-maintained yard. Lounge chairs are positioned near the water, and pathway stones lead to the pool, illuminated by soft lights above. The evening sky adds a serene backdrop.

4.97 out of 5 average rating, 121 reviews

Kissimmee/20 min to Disney/Private Heated Pool

This 3-bedroom house in Kissimmee is perfect for your escape to relaxation. With 2 queen beds and 2 twin bed, guest will find comfort and space to unwind. The property offers essential amenities like Wifi, a washing machine, and heating for a fantastic stay. The 2 bathrooms are equipped with a hairdryer and a shower for convenice. Our place is equipped for long or short stays to make your holiday one to remember.

4.91 out of 5 average rating, 129 reviews

Entire Modern Home near Disney • Pool & Game Room

Make memories at our beautifully renovated home in Kissimmee — close to Disney, Universal, and everything Orlando has to offer. Relax in your private pool, enjoy 3 comfortable bedrooms and 2 full baths, and check in easily with keyless entry. Nestled in the safe, gated community of Cumbrian Lakes, it’s the perfect spot for families and friends to unwind together.

A two-story home with a light brown exterior is set within a lush green landscape. A spacious driveway leads to a white garage with a large door. The property is enclosed by a white privacy fence, creating a secluded outdoor environment.

4.93 out of 5 average rating, 170 reviews

South Facing Pool Home! 5 Miles from Disney

Beautiful South Facing Pool Home! 5 Miles from Disney. This beautiful 4-bedroom home with two master bedrooms is located just minutes from Disney World, Sea World, Universal Studios, and other Orlando attractions.The home includes a private fenced in South facing swimming pool. We offer free Pool heat, Gas Grill, and High Speed Wireless internet and Cable TV .

A spacious living area is furnished with comfortable gray sofas and a soft rectangular ottoman. A stone accent wall with a mounted flat-screen TV adds texture. Artistic wall decor and stylish lighting fixtures complement the modern design, creating an inviting space for relaxation.

4.82 out of 5 average rating, 179 reviews

7485 - Luxurious 3 Bedroom Townhouse behind Disney

Welcome to your ultimate vacation getaway at Magic Village Views! Experience a stylish, centrally-located stay at this beautiful 3-bedroom vacation townhouse in Kissimmee, perfect for up to six guests. Just 10 minutes from Walt Disney World and 20 minutes from Universal Studios and Volcano Bay, this home offers comfort, convenience, and a touch of luxury.

Popular amenities for house rentals in Kissimmee

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

A private heated pool is surrounded by a screened enclosure, featuring a brightly colored tiled edge. Sun loungers are positioned nearby, offering a relaxing space to unwind. A covered BBQ grill is accessible on the patio, creating an inviting setting for outdoor gatherings.

4.92 out of 5 average rating, 106 reviews

3BR / 2BR Heated Pool Home 7 Min to Disney |

A sunlit pool area features a screened enclosure, providing a serene space for relaxation. The curved pool is surrounded by lounge chairs and provides ample space for outdoor enjoyment. Lush greenery is visible in the background, adding to the tranquil setting.

4.81 out of 5 average rating, 315 reviews

Sunnyside Villa Near Disney Private Pool 8 guests

An inviting pool area is framed by a screened enclosure, revealing beautiful water views at sunset. Soft lighting enhances the relaxing atmosphere, with lounge seating positioned nearby for comfort. The tranquil setting is ideal for unwinding and enjoying outdoor moments by the pool.

4.96 out of 5 average rating, 332 reviews

Game Room/HeatedPool/Piano Upscale Waterfront Home

The exterior of the home is showcased, featuring a sloped roof and a front entrance flanked by tall windows. A two-car garage is visible, surrounded by lush greenery and neatly trimmed bushes. Nearby houses and a clear sky can be seen in the background.

4.95 out of 5 average rating, 38 reviews

Disney Area 3BR Pool Home | Family-Friendly

A private patio area is presented, featuring a refreshing turquoise rug adorned with floral patterns. Two wicker chairs, accompanied by a small table and a potted plant, offer a cozy seating arrangement beside a sparkling pool, enclosed by a protective mesh screen.

4.95 out of 5 average rating, 83 reviews

Paradise Suite

The outdoor pool area features a heated pool and a jetted spa, surrounded by a screened-in patio. Two chaise lounge chairs are positioned nearby for relaxation, while a dining table offers additional seating. Natural light filters through the overhead structure, enhancing the inviting space.

4.94 out of 5 average rating, 129 reviews

Blue Door Escape - Private Pool - Close to Disney

An outdoor dining area features a large, custom-built farmhouse table surrounded by benches. Refreshments and fruit are displayed on the table, with a private pool visible in the background, enclosed by a screened lanai. Lush green grass complements the serene atmosphere.

4.95 out of 5 average rating, 216 reviews

★Completely Renovated★ 3 mi to Disney+Free Resort!

4.89 out of 5 average rating, 55 reviews

The Denmark

Weekly house rentals

4.94 out of 5 average rating, 97 reviews

Escape Oasis Home with Pool Spa, Games near Disney

A spacious game room features a full-sized billiard table, illuminated by an overhead fan. A vibrant green wall decorates the background, complemented by a neon sign encouraging relaxation. A small refrigerator and bar seating are visible in the adjoining area, enhancing the inviting atmosphere.

4.9 out of 5 average rating, 94 reviews

Casa Breeze - Cozy, Luxurious & Close to Disney

A swimming pool is situated in front of a club house, surrounded by palm trees and lounge chairs. The pool is clear and reflects the sky, while the club house features large windows and a rounded roof design. Sunlight illuminates the area.

4.94 out of 5 average rating, 68 reviews

Designer House <Next to Disney> Gated Resort

4.81 out of 5 average rating, 31 reviews

Astonishing Home at Windsor at Westside Resort

A private outdoor area features a heated pool with integrated spa and water fountain, surrounded by lounge chairs under a blue sky. A shaded dining area is visible alongside a summer kitchen, complemented by greenery and a basketball hoop in the background.

5 out of 5 average rating, 20 reviews

Modern Luxury 5BR Pool Movie+Game Rm @Encore 7770

A heated infinity pool is surrounded by lush tropical landscaping and palm trees. A hot tub is positioned nearby, inviting relaxation. Comfortable lounge chairs are scattered around the pool area, offering ample space for guests to unwind.

4.93 out of 5 average rating, 74 reviews

Pet Friendly Large 1 Bed/1Bbath condo at the Melia

An open-concept living area features a large sectional sofa in soft gray, arranged around a circular coffee table. A contemporary fireplace is integrated into the wall, providing a focal point. Glass doors lead to the outdoor pool area, enhancing natural light throughout the space.

5 out of 5 average rating, 56 reviews

Luxury Home w/ Pool & 6 Beds near Disney

5 out of 5 average rating, 18 reviews

4BR/3BA Townhouse w/ Private Pool in Storey Lake

Private house rentals

5 out of 5 average rating, 7 reviews

2039 Amazing Tropical Palms House w/Private Pool

A spacious bed with white bedding and decorative pillows is positioned against a wooden headboard. A bedside table with a lamp stands nearby, while a window covered by light curtains allows natural light to enter the room. A decorative piece is hung above the bed.

4.83 out of 5 average rating, 47 reviews

Private Guest suite in Kissimmee

A fenced-in backyard features a heated private pool with a unicorn float. Lounge chairs are positioned around the pool area, providing comfortable seating for relaxation. The surroundings include a well-manicured lawn and a clear sky above the screen enclosure.

4.95 out of 5 average rating, 62 reviews

Cozy Home, 20 mins from attractions!

A newly renovated house is presented with a white exterior and a bold orange front door. Large windows are framed with black shutters, contributing to the modern facade. A neatly maintained lawn surrounds the dwelling, while a driveway leads to the attached garage on the left.

4.96 out of 5 average rating, 27 reviews

10 mi to Airport - 20 to Disney

A fenced heated pool area is visible, surrounded by lush greenery and palm trees. The villa entrance features a welcoming façade and a spacious driveway. Inside, a games room showcases vibrant Nemo-themed murals, along with seating and game tables for recreational enjoyment.

4.97 out of 5 average rating, 30 reviews

Adult Luxury - Magic for Families!

The spacious open-plan living area features a large sectional sofa, a sleek coffee table, and a wall-mounted smart TV. A dining area with stylish chairs is visible in the background, along with a modern kitchen including a dining island, illuminated by pendant lights.

4.89 out of 5 average rating, 37 reviews

Stunning and modern 4 bedroom home with pool

4.95 out of 5 average rating, 43 reviews

Harry Potter House of Requirement KissimmeeOrlando

The image features a collage of various areas within the vacation home, including the outdoor pool area with a shaded screen, a cozy living room with modern furnishings, and a dining space. Bright colors from artwork and playful Disney imagery are present, showcasing the family-friendly atmosphere.