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!

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.

4.87 out of 5 average rating, 261 reviews

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**

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 |

✨ Experience comfort, style, and a private heated pool 💦 (optional) just 7 minutes from Disney World! This 3BR/2BA Kissimmee home is perfectly located near theme parks, shopping, and dining — and designed for families looking to unwind in a sparkling-clean, beautifully curated space. 📍Prime Kissimmee Location ⭐7 Min– Walt Disney World ⭐5 min–Orlando Premium Outlets ⭐15 min – Universal Studios, SeaWorld, Epic Universe 🎢 ⭐ 25 min – MCO Airport ✈️ ⭐ Walk to Walmart, Publix & Starbucks ☕️

A single-story home is showcased with a light gray exterior and a dark garage door. Lush green grass surrounds the front, complemented by palm trees and shrubs. The driveway leads to the entrance, under a clear blue sky with a few clouds.

4.9 out of 5 average rating, 150 reviews

Peaceful Waterfront Retreat, Close to Everything!

Beautiful 4br peaceful lakefront home in safe, quiet community. Close to major shopping and restaurants! Just a short drive to the Turnpike and 417 highway, close to Disney, Seaworld, Medical City, Lake Nona and the VA Hospital. Comfortable space with smart TVs and central AC. Fully equipped kitchen. Split floor plan perfect for families and friends. The master bedroom faces the rear of the home, large windows allowing natural light to enter the home all while enjoying your waterview!

A shaded outdoor deck features a rectangular wooden table surrounded by four dark wicker chairs. A ceiling fan hangs above, providing airflow. The view beyond includes lush greenery and the presence of trees, creating a serene and private setting.

4.89 out of 5 average rating, 116 reviews

Kissimmee cottage *15mi to WDW*

Brand new private home in Mill Creek RV park. 1 bedroom home with queen bed and additional pull out sofa. Play yard/crib available for 5th guest. Full kitchen, washer/dryer in home. Enjoy a central location backing onto a green space with pond for peaceful privacy on the back deck. Full access to all Mill creek amenities ( pool, gym, playground, corn hole, pickle ball, putting green) 2 smart TV’s in unit 1 mile to Walmart 15 mile to Disney World & Universal 13 mile to Orlando airport

Superhost

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!

Superhost

A screened-in pool area is illuminated by string lights, offering a serene view of the lake at sunrise. The inviting pool features floating noodles, and the surrounding space is bordered by greenery, enhancing the tranquil atmosphere.

4.85 out of 5 average rating, 214 reviews

Disney & Universal Retreat| Heated Pool | Fire Pit

Sit back and relax in this stylish home with all the amenities you need for a fun family getaway. This home has a spacious layout with 3 bedrooms and 2 baths. We have thought of everything so you don't have to-toiletries,washer/dryer, and wifi. Enjoy your morning coffee in the screened in pool area with a beautiful sunrise and lake view or sip a glass of wine while floating in the pool. Just minutes to Theme Parks and major highways, this is the dream home you have been waiting for!

4.95 out of 5 average rating, 112 reviews

Glamorous and Modern House 8 minutes to Disney

The house where your dreams come true, really close to Disney located in the gated Magic Village Resort. This house was practically built and decorated to offer the highest quality services our guests. This 4 bedrooms (all with private bathrooms attached) + 1 social bathroom house has everything you will need for a comfortable stay with your family & friends. It has modern appliances, furniture and BBQ/Grill the latest generation, with comfortable spaces and free Wi-Fi Internet.

4.96 out of 5 average rating, 135 reviews

A modern living area features an L-shaped sofa in a neutral tone, accompanied by a geometric area rug. A dining set with two blue chairs surrounds a small table by the window, separated from the entryway by decorative elements. A large wall-mounted TV is positioned across from the seating.

Home in Windhover

New & Modern 1 Bedroom - Walk to Universal Studios

Welcome to your vacation home, walking distance to Universal! This unit is part of a duplex and includes a full kitchen, with shared laundry on site. Located walking distance to Universal Studios, & within a short drive to Epic Universe, Volcano Bay Water Park, Wizarding World of Harry Potter, Disney World, Disney Springs, Sea World, Malls/Outlets, Downtown Orlando, Amway Center, Dr Phillips Performing Arts Center, International Drive, Convention Center.

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.

Popular amenities for Kissimmee house rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

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

A modern dining area features a long white table set for six, complemented by blue placemats and tableware. A comfortable living area with a blue sofa is visible in the background along with a sleek kitchen equipped with stainless steel appliances.

4.93 out of 5 average rating, 14 reviews

2024 Magic New 3 suites 5 Min to Disney

5 out of 5 average rating, 30 reviews

Escape to Nature Home Near Disney Big Yard & BBQ

A resort area is depicted with a large swimming pool surrounded by palm trees. The two-story building features numerous windows and outdoor seating, creating an inviting space. Soft evening light reflects on the water's surface, enhancing the tranquil atmosphere.

4.86 out of 5 average rating, 125 reviews

Resort TH 2b/2.5b With Private Hot Tub near Disney

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

4.87 out of 5 average rating, 181 reviews

Kingfisher at Watersong- Perfect for Disney!

4.91 out of 5 average rating, 34 reviews

Elegant Lake Villa - Game Room, Pool & Hot Tub!

Weekly house rentals

An outdoor space features a spacious pool surrounded by a sunbathing area. A covered seating area offers shade under a large umbrella, while palm trees add a touch of greenery. The screen enclosure provides protection while allowing for natural light and fresh air.

4.91 out of 5 average rating, 22 reviews

Dream vacation, near Disney

A spacious living area features a light-colored sofa with decorative pillows and a sleek coffee table. A large television hangs on a textured black feature wall. Natural light fills the space, highlighting the contemporary decor and the open layout leading to a dining area in the background.

4.83 out of 5 average rating, 18 reviews

Modern Escape in Kissimmee

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

5 out of 5 average rating, 41 reviews

Private Ranch Suite Enormous Yard

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

4.92 out of 5 average rating, 37 reviews

Luxurious Gem near Disney ~ Workspace ~ Movie Room

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, 36 reviews

Stunning and modern 4 bedroom home with pool

Private house rentals

The exterior of a modern two-story home is presented, featuring a stylish facade with light-colored walls and dark stone accents. Tall, rectangular windows provide natural light, while a paved driveway leads to a two-car garage. Lush greenery and palm trees frame the front entrance.

5 out of 5 average rating, 53 reviews

Luxury Home near Disney

A sprawling water park is displayed with multiple pools and slides. Lush palm trees provide shade, while guests enjoy leisurely floats in a lazy river. An array of colorful water slides adds vibrancy, surrounded by modern resort buildings, creating an inviting and fun atmosphere.

4.93 out of 5 average rating, 85 reviews

Spectacular Condo 2Bed/2Bath Close 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!

4.91 out of 5 average rating, 23 reviews

Fully renovated. 15Mi - Disney. 10Min - Airport.

5 out of 5 average rating, 30 reviews

15 Min to Disney•Cozy Home Heated Pool & Game Room

4.89 out of 5 average rating, 55 reviews

The Denmark

A modern living room is showcased, featuring a cozy seating arrangement with gray sofas positioned around a central table. A flat-screen TV is mounted on the wall, with plants and decor enhancing the space. Natural light floods in through the windows, brightening the room.

5 out of 5 average rating, 16 reviews

Haven Luxury