Villa holiday rentals in Kissimmee

A private movie theater features a 150-inch screen displaying a Disney image. Black walls and hardwood flooring create a modern atmosphere. Comfortable reclining seats with cup holders are arranged for a cinematic experience, ensuring a cozy and immersive viewing environment.

4.82 out of 5 average rating, 266 reviews

150 Inch 4K Movie Theater Pool & Spa sleeps 16

"Just 3 miles from Disney up to 16 guests! Unwind in the pool & jacuzzi. A private cutting-edge Movie Theater, featuring a 150-inch screen, 4K projector, and immersive surround sound. Relive your favorite movie moments like never before! Stream on Roku, game on PS5, and enjoy high-speed Wi-Fi for endless fun. The well-equipped kitchen is perfect for large families and with 6 bedrooms and 4 en-suite baths, privacy is guaranteed. A Star Wars and a Disney-themed rooms so the kids will feel at home.

A private pool area features a sparkling blue pool surrounded by a screened enclosure. Comfortable lounge chairs are positioned on the pool deck, with tropical landscaping visible in the background under a clear blue sky.

4.93 out of 5 average rating, 136 reviews

Time to relax and enjoy family time

Endless Summer Villa is the perfect vacation destination. With a game room, 4 bedrooms & 4 bathrooms, our villa is handicap accessible and perfect for families. Take a splash in the private pool or relax in one of our two master suites, each outfitted with top-quality furnishings and bedding. Let our beautifully landscaped pool transport you to a tropical paradise, all while being just a short drive away from Disney, SeaWorld, and Universal. Book your stay with Orista Endless Summer Villa today!

A spacious living area showcases a large sectional sofa adorned with colorful cushions, set against a striking stone wall decorated with framed artwork. Tall windows allow natural light to enter, while rich red curtains add a touch of warmth. A decorative rug anchors the seating area.

4.94 out of 5 average rating, 247 reviews

Enchanted Villa with Lake View 6-Bedroom in Resort

In the exclusive Lake Berkley Resort, this magical manor is a spacious 6 bedroom, 3.5 bathroom home with private pool & spectacular lake views. A 10 minute drive to Disney World, 15 minutes to Sea World and 20 minutes to Universal’s Wizarding World of Harry Potter. Ensure an immersive experience at this thematic home, perfect for families & groups of friends looking to cook in the well stocked kitchen, enjoy meals together in Great Hall or patio by the pool and watch movies & more in the Common

A private pool deck is enclosed with mesh, providing a clear view of the surrounding greenery. Two comfortable loungers are arranged beside the inviting swimming pool, adorned with orange striped towels. The peaceful outdoor space is well-lit by natural sunlight.

4.86 out of 5 average rating, 118 reviews

Sunny Family Retreat ~ Peaceful Pool ~ Game Room

Unwind in this sunny 4 Bedroom 3 Bath house nestled in a serene family-friendly neighborhood. This prime location allows quick access to nearby restaurants and shops while being just a short drive away from Disney World, Universal, Legoland, and more. The lively pool deck and entertaining game room offer various relaxing and fun amenities. ✔ 4 Comfortable Bedrooms ✔ 3 Large Bathrooms ✔ Fully Equipped Kitchen ✔ Swimming Pool ✔ Game Room ✔ Six TVs w/ Roku ✔ Sun Loungers Learn more below!

The outdoor living space features a cozy seating area surrounding a fire pit and a large dining table. A private swimming pool is illuminated in blue, with sun loungers lining the edge. The backyard is framed by palm trees, creating a tropical ambiance at dusk.

5 out of 5 average rating, 110 reviews

8 BR Villa, Private Pool, Theater, Min to Disney!

Big and Beautiful Themed Vacation Villa in premium gated Encore Resort. Spacious main floor for entertaining large groups - bring the family and friends! Enjoy the included resort amenities a minute's walk from the front door. Or, relax around your private pool and custom summer kitchen. Enjoy big-screen movies and sound in the theater in premium loungers, and play classic arcade games! 10-15 min from Disney, one of the closest villa resorts. Tons of shopping and dining nearby!

The image showcases a vibrant collage of the villa's features. The top left displays a colorful Encanto-themed bedroom with a playful bed. The top right features the modern living area with large windows and comfortable seating. The bottom left presents a private pool area, and the bottom right highlights a Mario-themed game room with arcade games.

4.98 out of 5 average rating, 119 reviews

5BR Family Vacation Villa w/Free Pool Heat

Professional Hosts & Guest Favorite Home! Immaculate and well equipped Stargazer Villas vacation home at Windsor Island Resort now featuring Pickleball Court! This central Florida villa has heated pool included for your family to relax in after a busy day at the parks. Family friendly, featuring Star Wars, Harry Potter, & Encanto themed bedrooms, and a new Mario World game room! Stargazer Villas provides the perfect place to create unforgettable memories with your family.

A vibrant collage highlights the Tiki Tropical Oasis. The inviting pool is surrounded by lounge chairs under umbrellas. A colorful putting green and BBQ grill add to the outdoor appeal. The interior features thematic rooms, showcasing tropical decor and immersive environments designed for family enjoyment.

4.99 out of 5 average rating, 109 reviews

OMG Private Pool Oasis! LED Lights! Mini Golf!

This is the place! Look no further for the most magical immersive dream vacay! Welcome to your own private tropical paradise oasis minutes from Disney World! In Encore Resort by Reunion (gated community) enjoy your private pool, hot tub/jacuzzi, hammock swings, tiki bar, unique mini golf experience. The LED lighting in the backyard & throughout the house will wow you! Gorgeous decor and immersive themed rooms for the kids! The perfect place for your dream family vacation!

4.91 out of 5 average rating, 238 reviews

House by the Mouse: Something for Everyone!

Welcome to our completely remodeled solar four bedroom, three bath villa, less then four miles to Disney World, and only a short drive to Universal, Sea World, Lego Land, and other local attractions. Designed themed bedrooms include Harry Potter, Mickey and Minnie Mouse, Star Wars, and a romantic master bedroom that allows you to relax in comfort. The pool, spa, and the entire villa is just for you, no need to share with anyone else, so kick back and enjoy!

A game room features striking themed decor, with large flat-screen TVs and seating. The private pool area showcases a serene swimming pool surrounded by a screen enclosure, highlighted by comfortable lounge furniture. A cozy outdoor seating area is visible, offering a relaxing view.

4.95 out of 5 average rating, 156 reviews

"Disney Serenity": Luxe 8BR Villa/ Privacy/ Pool

**Exclusive Discount!** Mention **Disney Serenity** when booking 90+ days in advance for special savings! 🏡 **Welcome to Disney Serenity** – a family-friendly villa near Disney World! Enjoy a **private heated pool**, **game room**, and **cinematic home theater**. Plus, access resort amenities like a **lazy river, gym, and tiki bar**. **Wheelchair-friendly** and perfectly located for Disney & Universal adventures. Book now for a magical stay! ✨

A private screened patio features a heated swimming pool and a Jacuzzi surrounded by a spacious deck. Outdoor seating is provided, with a dining table and lounge chairs positioned for relaxation. Sunlight glimmers on the water, creating a serene atmosphere.

4.91 out of 5 average rating, 114 reviews

Gorgeous 3 bed, 2 bath villa w/ pool and jacuzzi

Gorgeous 3 bedroom, 2-bathroom villa set on a 1/4 acre of land, with our own screened, private, heated swimming pool & Jacuzzi, and high speed internet. Situated in a quiet residential community on the sought after Sunridge Woods in Davenport, only 9 miles from Disney. 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**

Villa in Championsgate Village

The image displays four distinct sections of Sky Lantern Manor. A vibrant kids' room with a whimsical design is featured. An indoor theater is shown with plush seating. An outdoor view reveals a private pool surrounded by a lanai. A game room is highlighted with colorful LED lighting.

4.96 out of 5 average rating, 105 reviews

Walk2Clubhouse|PickleBall|Pool Movies|GameRm|Theat

Sky Lantern Manor is your dream Disney escape! With 3 luxe Master Suites and 3 themed kids’ rooms (Rapunzel, Moana & Avengers), plus a Star Wars theater, outdoor movies, karaoke, and a game room with Xbox & arcades, the fun never stops! Splash at the Oasis Club’s lazy river & slides or dive into the Retreat Club’s new waterpark. Make every moment magical—your storybook adventure starts here!

An enclosed patio area surrounds a swimming pool, featuring several lounge chairs spaced evenly around the deck. Lush greenery is visible beyond the screen enclosure, offering a view of the tranquil outdoor setting.

4.73 out of 5 average rating, 112 reviews

Disney area 4-bedrooms spacious villa for rent

Our villa offers a pleasant and relaxing place for families at an affordable price. Rent a private villa with a gorgeous swimming pool in a family-oriented residential neighbourhood. It has an excellent conservation view and outdoor space with a small pond. This home is in Eagle Point, Poinciana Blvd. in Kissimmee, near the Walt Disney World Resort.

Popular amenities for villa rentals in Kissimmee

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Private villa rentals

4.84 out of 5 average rating, 19 reviews

Villa in Clermont

Family villa w/ screened pool & spa

The newly renovated pool is visible within a screened enclosure, providing a safe area for enjoyment. The pool is shaped uniquely and features clear blue water, creating a refreshing focal point in the outdoor space surrounded by inviting patio areas.

4.92 out of 5 average rating, 63 reviews

Vacation 3 bedroom 2 bath Villa+pool

A single-story home with a light beige exterior features a well-kept lawn bordered by shrubs. The front porch, highlighted by four windows, leads to a dark front door framed by decorative elements. A clear blue sky completes the inviting outdoor scene.

4.75 out of 5 average rating, 8 reviews

Florida Cottage Getaway - (4958TV)

A private pool area is framed by a screen enclosure, with views of the lake in the background. Clear blue skies and fluffy clouds reflect in the water. Surrounding greenery adds a natural touch, creating a serene outdoor space ideal for relaxation.

4.95 out of 5 average rating, 79 reviews

Lakefront Private Pool Villa, 10min to Disney

A screened-in outdoor area features a heated in-ground pool, surrounded by paved decking. Comfortable seating is provided, with lounge chairs positioned nearby. The space is enclosed by a sturdy fence, ensuring privacy while enjoying the serene surroundings.

4.82 out of 5 average rating, 241 reviews

Veranda Palms Luxurious Home w/Pool & NEAR DISNEY

4.85 out of 5 average rating, 48 reviews

A heated swimming pool is enclosed by screen protection, providing a clear view of the water. Surrounding greenery adds privacy, while a patio area features sun loungers and a grill for outdoor dining. Sunlight reflects off the water, creating a bright atmosphere.

Villa

South facing Modern villa in quiet gated estate

The open living area features high ceilings, large windows, and a cozy seating arrangement with a sofa and armchairs. Decorative wall art and plants enhance the design, while an elegant dining space and modern kitchen are visible in the background.

4.99 out of 5 average rating, 81 reviews

The Balmoral Manor: Luxurious & Bright 5BR Oasis

A private swimming pool is enclosed within a screened area, featuring a vibrant pink flamingo float and a donut-shaped float. Sunlight reflects off the water, while a serene lake view is visible in the background, enhancing the outdoor experience.

4.93 out of 5 average rating, 15 reviews

*Special Offer*NearDisney/LakeView/PrivatePool 5BR

Luxury villa rentals

A vibrant themed room showcases a blue slide and bunk beds, enhancing playfulness. Adjacent, a cozy bedroom features rich curtains and themed decor. A home theater room displays a large projector screen and comfortable seating. The private pool area is highlighted with seating, a projector, and colorful inflatables.

4.97 out of 5 average rating, 116 reviews

Pickleball PoolsideMovies |WalkToWaterpark| Arcade

4.97 out of 5 average rating, 113 reviews

15min2parks! 9B, Pool/Spa/Theater/Karaoke/Vgames

An inviting outdoor pool area is featured, surrounded by a protective screen enclosure. The pool water is a clear turquoise, reflecting the evening sky. Comfortable seating is arranged nearby, alongside a BBQ grill. Soft lighting enhances the tranquil atmosphere.

4.94 out of 5 average rating, 121 reviews

❤NEW Gorgeous 5br/3.5ba|POOL| Game ROOM| Disney

A vibrant outdoor area features a sparkling saltwater pool with fountain jets and colorful LED lighting. A large screen displays a movie, surrounded by lounge chairs. The area is enhanced by string lights and a cozy seating arrangement, creating an inviting space for relaxation and entertainment.

4.88 out of 5 average rating, 225 reviews

Mad Men Magic Kingdom House*FAB POOL*OutdoorMOVIE

A spacious living room features a large sectional sofa arranged around a wall-mounted television. Natural light enters through large windows, enhancing the airy atmosphere. A game room showcases a pool table and arcade games, while the private pool area is enclosed with a netted structure, ensuring safety and comfort.

4.86 out of 5 average rating, 133 reviews

NEW Unique 6BR,private pool,Full game room, + MORE

The outdoor screened lanai provides a private pool and spa with seating areas overlooking Storey Lake. Lounge chairs are arranged around the pool, situated in a spacious setting, creating an inviting space for relaxation.

4.92 out of 5 average rating, 52 reviews

Lakeview Luxury Villa with Everything!

The image showcases a vibrant outdoor area featuring a private pool and spa, with a large projector for outdoor movie viewing. Inside, two game rooms are filled with themed decor and various entertainment options, including virtual reality experiences and arcade games.

5 out of 5 average rating, 44 reviews

Rotating VR Machine, Arcade, Slide | 3mi to Disney

The image displays four themed bedrooms, each uniquely designed. A Moana-inspired room features vibrant ocean murals and a queen bed. The Toy Story room shows playful characters with a twin bunk bed. A Frozen-themed room highlights snowy landscapes with two twin beds, and a Mickey Mouse room displays bold colors and playful decor.

4.94 out of 5 average rating, 68 reviews

Top Rated Luxury Villa @ Storey Lake mins 2 Disney

Villa rentals with a pool

4.91 out of 5 average rating, 56 reviews

Luxury Villa 6BR/6.5 BA Near Disney/Sleeps16/Pool

5 out of 5 average rating, 9 reviews

Casita Kissimmee!Family Vacation Villa! 8minDisney

5 out of 5 average rating, 25 reviews

7BR Disney Villa Escape Room+ Pool +Cinema+Game Rm

The exterior of a two-story villa is displayed, featuring a beige facade with a red tile roof. A blue front door welcomes guests, flanked by windows. A well-maintained lawn surrounds the home, complemented by small shrubs and trees. A paved driveway leads to a garage on the left.

4.89 out of 5 average rating, 37 reviews

Disc rate Spacious View4bdrm SplashPool & Yoga Rm

A vibrant gaming room is highlighted with space-themed murals and wall art. A pool table sits centrally, flanked by a modern lighting fixture. The room includes two large television screens and multiple gaming chairs for comfortable play.

4.96 out of 5 average rating, 47 reviews

Private Family Villa w/ Pool, Game Room, Resort

An aerial view showcases the expansive resort amenities illuminated at night. The area features a winding lazy river, a large pool, palm trees, and lounge chairs strategically placed around the pools. The clubhouse is prominently situated, surrounded by landscape elements that enhance the outdoor space.

4.79 out of 5 average rating, 80 reviews

Dreamy 5 Bed w/ Game Room, Pool & Themed Bedrooms!

The pool deck features a spacious swimming pool surrounded by a screened enclosure. Four sun loungers are positioned nearby, accompanied by a cantilevered umbrella for shade. The tranquil conservation area is visible in the background, providing a peaceful setting.

4.98 out of 5 average rating, 46 reviews

Beautiful 4 bedrooms with South/West facing pool