Villa holiday rentals in Kissimmee

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.

4.87 out of 5 average rating, 148 reviews

Unique 6BR Home • Private Pool & Full Game Room +

Create unforgettable memories in this family-friendly vacation home near Disney. Spacious 6BR / 5.5BA with themed rooms,TVs throughout, fully equipped kitchen, private pool, BBQ area and resort-style amenities. Enjoy an epic game room with arcade games, pool table, play area, tube slide, bar and PS5. Perfect for families, groups and friends seeking comfort, fun and great vibes. A wild stay awaits!! Plus, enjoy relaxing outdoor spaces, amazing photo spots, and nonstop entertainment for all ages!!

4.69 out of 5 average rating, 115 reviews

Spacious Disney Getaway: King Suites, Pool & Spa!

Escape to the magic of Orlando with your family and friends in style! Discover the ultimate vacation experience at our stunning 5-bedroom rental in the Bella Vida Resort, Kissimmee. This is your gateway to an unforgettable Florida getaway! Bella Vida Resort is conveniently located just minutes from Walt Disney World, Universal Studios, and all the top attractions Orlando has to offer. Plus, you'll have easy access to restaurants, shopping, and golf courses for an all-around incredible vacation.

A themed game room showcases a Batman-inspired design with a bright yellow slide leading to a two-level play area. An air hockey table is positioned prominently, surrounded by stylized dark walls, creating an immersive gaming environment.

4.96 out of 5 average rating, 161 reviews

Sleeps 21|Free Pool Heat|15 min to Disney|Hot Tub

Make memories to last a lifetime in our luxurious seven-bedroom home (sleeps 21) at Orlando's premier vacation community. Enjoy your own Batman cave game room, private pool (heated at no extra charge*), and hot tub. Our 100% Five-Star rating from previous guests and our generous cancellation policy means you can book with confidence. Only 15 minutes to Disney and a short walk to a fabulous resort clubhouse with free access to a lavish pool, kids waterpark, restaurant, playground, gym, and more!

4.95 out of 5 average rating, 121 reviews

Beauty 4 miles to Disney 3Br 2Ba Pool Home

Clean & Cozy stay in private pool home. Can't beat the location!! 4 miles to Disney World. 4 mi to Orlando Premium Outlets. Epic Universe 9.5 mi Free Garage & driveway parking. Peaceful Neighborhood. One floor house within minutes of all Orlando theme parks. Magic Kingdom, Animal Kingdom, Universal Studios, Island of Adventure, Sea World & Aquatica. The area is also filled with dining and shopping options. This special place is managed with care and love to build your unforgettable experience.

An outdoor dining area features a large, custom-built wooden table surrounded by black chairs. Blue plates and glassware are meticulously arranged for an inviting meal. A bright blue pool glimmers in the background, enclosed by a mesh screen to ensure privacy.

4.97 out of 5 average rating, 167 reviews

*Hibiscus Hideaway* Minutes to Disney+Free Resort!

Closest FREE resort to Disney Parks! Hibiscus Hideaway is a 6 bedroom 4 bathroom luxury villa that sleeps 14. Completely renovated in October 2022! * Kitchen is loaded & all baby gear provided. * Custom game room with A/C, LED panel lighting & ROCK CLIMBING WALL! * New Roku smart TVs & NEST tech throughout. * Outdoor space includes your own private pool, hot tub, overhead lighting, NEW BBQ grill & 10' custom-built farmhouse table to seat the whole family! Every detail has been thought of!

The image captures a view from the pool, showcasing the villa's large glass windows and covered outdoor seating area. Loungers are positioned around the pool, offering ample space for relaxation. The sparkling water reflects the modern architecture above, framed by a screened enclosure.

4.94 out of 5 average rating, 131 reviews

Private Pool & Free Heat - Close to Disney!

3 bed, 3 bath luxury villa in exclusive gated community 10 mins from Disney. Private pool & hot tub with free heat not overlooked by other homes. Main rooms open onto pool. Kitchen with granite counter tops. Outside bar, loungers, table & chairs. Master bedroom with double sink ensuite and twin with ensuite shower room. Queen is separate to main house providing additional privacy when travelling with friends/family. 32 inch tv's and comfortable beds with pillow top mattresses in all bedrooms

A game room features various entertainment options, including a treadmill, exercise bike, and classic arcade machines. The decor showcases a 'Star Wars' theme with vibrant blue lighting and dark walls, creating an inviting atmosphere for guests to enjoy recreational activities.

4.93 out of 5 average rating, 113 reviews

Luxury Villa! /Game Room/ Pool Heater

Luxury Villa on a gated community in Kissimmee (Four Corners). Modern. Situated 10 min. from Disney theme parks. Well decorated and presented. Game Room, Mini Gym, Beautiful, large pool deck which is totally enclosed and secluded. There is a private Pool and overflow Spa. Three Bedrooms and Bedroom one is separate from the main house but still enclosed in the building. This would be ideal for a young couple within the group as it has its own bathroom, small kitchen and also total privacy.

4.87 out of 5 average rating, 127 reviews

8Bd 4K Movie Theater 155 Inch Screen Pool & Spa

A vacation home that takes your entertainment seriously! That’s our 8-bedroom villa in Emerald Island Resort at 3 miles from Disney… Ready to enjoy themed bedrooms, a premium private movie theater with a 155-inch screen, 4K projector, 5.1 surround sound, and a PS5 for gaming? Relive your favorite films in stunning quality, just like in the best movie theaters. Private Pool and Spa will make your vacation unforgettable! We’re ready for families and groups, to offer fun, comfort, and luxury.

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.

4.87 out of 5 average rating, 255 reviews

Mad Men Magic Kingdom House*FAB POOL*OutdoorMOVIE

AMAZING Pool Deck Extension cira 2023! Its the BIGGEST pool deck at the resort! Plus JAW DROPPING, Fancy, Fun, Fountain Jets w/ LED lighting, high-end glass tile & a Mickey Mosaic giving you an ULTIMATE luxury pool experience. This SALT WATER POOL/SPA will leave your skin feeling soft w/ no eye-sting & it has botanical qualities for your muscles after long days at the parks! Enjoy all this plus our unique OUTDOOR MOVIE EXPERIENCE & FIRE-PIT for the BEST vacay ever only 6 miles to Disney!

4.94 out of 5 average rating, 124 reviews

Storey Lake 10BR Villa Near Disney, Pool Waterpark

✨ Step into your own Disney adventure! Once an NBA star’s vacation home, this villa sleeps 23 and blends luxury with fun: • 🛏 Themed Bedrooms (Frozen, Cars, Harry Potter, Star Wars & more) • 🎬 Galactic Theater w/ 86” Screen, Surround Sound, Arcade, Xbox & Nintendo • 💦 Heated Pool & Spa w/ Lounge Seating + Peaceful Forest Views • 🎢 Resort Water Parks w/ Lazy River, Pirate Ship, Water Slides & Mini Golf • 📍 Prime Location: Only 7 Miles to Disney & 19 Miles to MCO attractions

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, 136 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!

4.93 out of 5 average rating, 102 reviews

Batman’s Cave w/ Pool + BBQ | Game Room Fun

Welcome to this enchanting 7-bedroom, 5.5-bath single-family home at Windsor Island Resort, just 9 miles from Disney! Beautifully designed space, it’s perfect for families seeking comfort, fun, and convenience. The first floor features a King suite, spacious living and dining areas, a fully equipped kitchen, laundry room, and a themed game room with PS5 and PlayStation Plus. Step outside to a private north-facing pool area with a 75" Smart TV for outdoor entertainment.

Popular amenities for Kissimmee villa rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Private villa rentals

4.91 out of 5 average rating, 34 reviews

5 Bed Villa | Private Heated Pool | Near Disney

A spacious dining area features a long glass table surrounded by white chairs, set for a large meal with blue and gold accents. A striking blue wall with geometric gold patterns creates a modern backdrop, while contemporary light fixtures illuminate the space.

4.94 out of 5 average rating, 131 reviews

Blue Paradise 15BR 11BA, Sleeps 36, Theater/GameRm

4.88 out of 5 average rating, 185 reviews

Premium 6BR | Theater, Games & Heated Pool

The exterior of a single-story home is presented, featuring a paved driveway leading to a two-car garage. Lush green grass surrounds the house, and palm trees are positioned near the entrance. A colorful sunset sky provides a picturesque backdrop.

4.99 out of 5 average rating, 156 reviews

Beautiful home. Private pool. Close to Disney!

4.88 out of 5 average rating, 101 reviews

Villa in Four Corners

6BD Villa, Game Room, Home Theater, Pool/Sleeps 15

A private pool area is illuminated in a soft green hue, surrounded by a screened enclosure. Comfortable lounge chairs are positioned nearby, with a table set under an umbrella. String lights create a warm ambiance as the evening sky darkens.

4.96 out of 5 average rating, 157 reviews

Magical Disney House-Pool & Hot Tub,Free Waterpark

The image showcases a vibrant gaming area with a glowing dance floor, a relaxing outdoor space featuring lounge chairs near the pool, a themed sleeping area with bunk beds, and a foosball table positioned in a cozy game room filled with colorful lighting.

4.97 out of 5 average rating, 73 reviews

6 BD/4.5 Ba Sleeps 14! Lily Pad At Solterra Resort

4.99 out of 5 average rating, 149 reviews

Villa in Osceola County

*Private Golf-Front Oasis with Pool, Spa & Cinema

Luxury villa rentals

A private pool area with a raised hot tub is enclosed by a screen, offering safety and quality views of the surroundings. The pool is accented by textured stonework and features a basketball hoop. A vibrant sunset casts colorful hues across the sky.

4.93 out of 5 average rating, 176 reviews

Private Villa near Disney & Universal W/Pool & Spa

4.98 out of 5 average rating, 122 reviews

Orlando Family Reunion Villa with Stage & Theater

A themed bedroom features dark walls adorned with a space mural, creating an immersive atmosphere. A large bed is dressed in colorful bedding featuring popular characters. A wall-mounted television is positioned above a dresser, complementing the room's playful design.

4.98 out of 5 average rating, 287 reviews

Disney-Themed Home w/ Game Room & Private Hot Tub!

An inviting screened-in lanai features a private pool surrounded by paver decking, with vibrant sunset colors reflecting overhead. The large dining area showcases a long table set for gatherings, accompanied by stylish light fixtures. The game room is equipped with multiple entertainment options, including arcade games and a pool table.

4.84 out of 5 average rating, 102 reviews

Brand New Luxury 9BR Villa/ Pool/Spa/Game Room

4.97 out of 5 average rating, 120 reviews

A private pool is framed by a stone patio, with lounge chairs positioned nearby for relaxation. Lush greenery and palm trees surround the area, creating a serene outdoor environment. A spa is positioned next to the pool, providing an inviting space for relaxation.

Villa in Four Corners

The Golden Bear Villa | Private Pool & Theater

4.97 out of 5 average rating, 137 reviews

Luxury Themed Villa 9 BR | Close to Disney

A vibrant game room displays an air hockey table and foosball station, with colorful LED lights casting an engaging glow. An adjoining indoor theater features plush seating and a large screen, while a private pool area invites relaxation, surrounded by lush greenery and floatation devices.

4.97 out of 5 average rating, 124 reviews

Pool Movies|Water Park|Movie Theater|Arcade|Themed

4.94 out of 5 average rating, 176 reviews

S-StoreyLake 9BR Sleeps 26 w/pool 5mil to Disney

Villa rentals with a pool

A private pool area is enclosed with a screen, revealing a sparkling pool surrounded by lounge chairs. The living room features comfortable seating arranged around a coffee table, complemented by large windows. An entertainment area showcases arcade games and a race car setup, while a hot tub offers a spot for relaxation.

4.92 out of 5 average rating, 77 reviews

Windsor Hills 5BR • Free Heat • Private Arcade

4.72 out of 5 average rating, 47 reviews

Tropical Boho Lakefront Villa | Private Pool & Spa

A spacious living area features light hardwood flooring and a large flat-screen TV mounted on the wall. Soft curtains frame the sliding glass doors, allowing natural light. A comfortable gray sofa and a chaise lounge provide seating, complemented by a textured area rug and decorative pillows.

4.93 out of 5 average rating, 102 reviews

FREE heated pool, 4BR near Disney, sleeps 11

A screened-in lanai features a private swimming pool with a clear blue surface. Dining area visible through sliding glass doors includes a table and chairs. The exterior is illuminated, creating a serene ambiance for evening relaxation.

4.78 out of 5 average rating, 83 reviews

Crystal Cove Villa: Relaxing 4 Bedroom 3 Bath Home

4.81 out of 5 average rating, 42 reviews

Luxury Townhouse Near Disney | 3BR

4.93 out of 5 average rating, 84 reviews

Lakeview Villa| Heated Pool, BBQ & Near Disney

A spacious living area features a modern sectional sofa, complemented by a circular coffee table and decorative plant. Bright natural light enters through window slats, enhancing the contemporary aesthetic, while the kitchen area is visible in the background with sleek cabinetry and appliances.

4.88 out of 5 average rating, 119 reviews

Charming 4 Bdr~ Villa near Disney

A large wooden dining table is surrounded by eight wooden chairs, set against a backdrop of stone-like walls with arched windows. A metal chandelier hangs overhead, while a decorative knight statue stands in the corner, adding character to the atmospheric space.