Villa vacation rentals in Kissimmee

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Top-rated villa rentals in Kissimmee

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Top guest favorite

The villa features a distinct architectural style with a terracotta roof and a landscaped front yard. Lush palm trees are positioned around the entrance, while a spacious driveway leads to a three-car garage, all set against a tranquil evening sky.

Villa in Kissimmee

5 out of 5 average rating, 116 reviews

Villa Sol Peaceful private Pool/Hot tub Home

Close to all major attractions, and airport sits this private villa. It has a little something for all ages! Your family can play in the pool or relax in the hot tub. Enjoy fun game nights with a cabinet full of games, or play a game of basketball, pickleball, or tennis right outside our pool. Fun on the playground or enjoy the clubhouse gym. All of your needs for the beach trips or the ball games. All of your baby's needs are covered as well. Ask about Stroller and cart rentals. We have it all

Superhost

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.

Villa in Kissimmee

4.86 out of 5 average rating, 101 reviews

Charming 4 Bdr~ Villa near Disney

We offer a Luxurious Villa with the things you need to enjoy your stay in the most wonderful experience possible. 4 bedrooms, 3 bathrooms,dedicated game room and private pool you will be able to enjoy all day fun while still having space to relax after a long day at Disney World. Brand new Villa extremely comfortable and well-equipped for up to 8 people, free parking,free wifi and more make it a great choice for families or groups of friends. Have fun with the whole family at this stylish place.

Guest favorite

Villa in Kissimmee

4.82 out of 5 average rating, 261 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.

Top guest favorite

Villa in Davenport

4.93 out of 5 average rating, 136 reviews

Rest Relax Unwind at Orista Endless Summer Villa

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!

Superhost

A private pool is set within a screened enclosure, overlooking tranquil waters. Lounge chairs with striped cushions are arranged near the pool, and lush greenery frames the serene view, creating a relaxing outdoor space.

Villa in Kissimmee

4.88 out of 5 average rating, 112 reviews

Beautiful Home with Pool near Golf & Disney

This luxury 4 bedroom home with a private pool and waterview is located in the gated golf community of Remington, within 20 mins of all Disney Parks, Universal Studios and the Orlando Airport Perfect for 1 or 2 families with 2 master bedrooms with ensuites bathrooms and 2 additional bedrooms with 2 twin beds each and a shared bathroom. Each bedroom has a flat TV as well as a 55 " flat screen in the living area. Fully equipped kitchen, plus washer and dryer We welcome you to enjoy our villa!

Guest favorite

A private pool is framed by a screened enclosure, featuring a gentle waterfall and bordered by comfortable lounge chairs. The serene lake view is visible beyond the pool, complemented by lush greenery lining the shore.

Villa in Kissimmee

4.87 out of 5 average rating, 186 reviews

Near Disney Gated LakeView Pvt Heated Pool

Lowest Cleaning fee! Military discounts. New Sofa set, Dolby Home theatre, new 65" HD LED TV w/ Airplay. A separate Remote office setup! Sunset Lakes is a secured gated comnty ~12 min from Disney & other parks. Updated Villa offers Lake View pvt pool, gorgeous sunset, Play room, BBQ Grill, Fishing dock. Fully furnished & sparkling clean w/ 4 beds - 1 King, 2 Queens, 2 Twin beds with 3 baths, kitchen & laundry. Come & enjoy your next trip to Disney & leave everything to a fantastic experience!

Guest favorite

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.

Villa in Davenport

4.94 out of 5 average rating, 120 reviews

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

Nestled in the peaceful 4 Corners community close to Disney & top rated attractions, Target, Publix & restaurants. Newly updated, inviting and modern 2 level, 5 bedroom/3.5 bath with comfortable luxurious beds! Equipped with a private pool (heat for an extra fee), game room, BBQ grill & free Nespresso. Out back is a mini golf putting green, corn hole and fire pit for the family to gather around under the warm vibe of string lights. A place for the family to retreat, relax, reset and have fun!

Superhost

Villa in Kissimmee

4.79 out of 5 average rating, 205 reviews

King Bed • Pool • Free Parking • 14 min to Disney

✅ Ensuite baths in every bedroom ✅ Windsor Palms Resort access – no resort fees ✅ FREE parking ✅ Private splash pool ✅ 14 minutes to Disney ✅ 5 minutes to shopping & dining Escape to your oasis! Park in your private spot, kick off your shoes, and enjoy crisp, clean reverse osmosis water. Your private splash pool—just steps from the kitchen—beckons you to relax. Feet up, worries out… welcome home. Your perfect retreat awaits—book today! NOT SURE? Ask any question - just press "ask host"

Superhost

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.

Villa in Kissimmee

4.89 out of 5 average rating, 223 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!

Guest favorite

A home cinema room features a large flat-screen TV displaying a film scene. The walls are painted blue and red, and plush seating is arranged in front of the screen. Decor includes framed posters and a Mickey Mouse silhouette, creating an engaging entertainment space.

Villa in Kissimmee

4.86 out of 5 average rating, 422 reviews

OMG! Disney Area, Movie Theater, Game Room & Pool!

Comfort and Space in an Elegant home with a lot of amenities, 4Bed/3Bath. Private Movie Theater, Game Room, Pool and Themed Rooms. Here the Fun never ends! A well equipped Kitchen, Laundry, 3 parking spaces, WiFi and Smart TVs. The house is located at Crystal Cove Resort, a gated community, close to Disney. Perfect Location! Few minutes to Walmart, Target, Sams Club, Publix, Outlets, Restaurants, Disney, Sea World, OCCC, EPIC and Universal. Magic Kingdom is Only 20 minutes driving!

Top guest favorite

A private pool area is enclosed by a spacious screen, featuring a clear blue pool with steps leading in. Two white lounge chairs are set beside the pool, offering a relaxing spot under the sun. Lush greenery is visible in the background.

Villa in Kissimmee

4.94 out of 5 average rating, 139 reviews

Beautiful Villa with pool near Orlando attractions

This home with a private pool is just what your family needs for that memorable vacation in Orlando. The privacy fence around the house provides the privacy you deserve to enjoy your private backyard and pool to the max! we focus the design to create the story of a perfect vacation for you, your family, and your friends. Enjoy the game room full of gaming options. Our Home is close to major parks and attractions such as Disney, Universal, Sea World, Gift shop, and Outlets.

Guest favorite

A private pool area is enclosed by a protective screen, showcasing clear turquoise water. Lush palm trees are visible in the background, providing a tropical ambiance, while the surrounding patio features lounge chairs for relaxation. A spacious outdoor environment invites leisure and enjoyment.

Villa in Kissimmee

4.77 out of 5 average rating, 229 reviews

Feel the Magic:9min Disney • South Pool • Play Fun

✨ Your Magical Getaway Starts Here Wake up to the Florida sun shining over your private pool, unwind in the spa at sunset, and enjoy memorable days in a charming, fully equipped, and comfortable home. Magic Kings House invites you to create unforgettable memories with family and friends, offering comfort and privacy in Windsor Palms, the resort of choice for the guests. Every detail has been thoughtfully prepared to make your vacation easy, relaxing, and truly memorable.