
Villa holiday rentals in Kissimmee
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Top-rated villa rentals in Kissimmee
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Bright Open-Concept Home | Pool and Jacuzzi!
Escape to the magic of Orlando with your family and friends in style! Discover the ultimate vacation experience at our stunning 4-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.

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!

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!

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

Villa Near Parks/Hot Tub/Pool/Golf/Sunset Views
Stunning 5BR, 3BA Highlands Reserve Golf Resort Estate overlooking the golf course with breathtaking sunset views. The SW-facing pool maximizes sun exposure and offers stunning sunset vistas. Minutes from Disney (12 min) and MCO Airport (20 min), with nearby restaurants, bars, and outlets. Enjoy a 4-person hot tub poolside and Smart TVs throughout, for seamless streaming. Whether relaxation or adventure, this private pool home in a golf community promises an unforgettable getaway for all ages.

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.

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!

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 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.

"Magical 8BR Resort Oasis: Pool, Themes & Games!"
Welcome to Grand Orlando! Discover a luxurious 8-bedroom retreat at Windsor at Westside Resort, featuring a grand open-plan living space, a fully-equipped kitchen, and two large dining tables. Enjoy a Marvel-themed game room, a Pixar loft with a giant movie screen, and themed bedrooms including Star Wars and Harry Potter. Outdoors, find a LED-lit pool with color-changing lights, a BBQ area, and an outdoor TV. The perfect blend of comfort and magic for an unforgettable stay.

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!

Luxury Themed Villa 9 BR | Close to Disney
🏖️☀️🏄♀️Experience the heart of Orlando in this luxurious house! Perfect for an unforgettable time with family, this new house has 9 stylish bedrooms and can house 22 people! This house is incredibly close to Disney World, Universal, Sea World, and the Orlando Airport! Located in Storey Lakes, Orlando's premier resort, we have wonderfully themed bedrooms (perfect for kids!), a game room, and a patio and pool.🌴👙🩳🥽🩴 We'd love to welcome you here!❤️❤️

Cozy 3 bed, 2 bath home 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**
Popular amenities for villa rentals in Kissimmee
Private villa rentals

Best Value BnB Disney Villa W/ Private Pool & SPA

5 Bed Villa | Private Heated Pool | Near Disney

10Br Pet Friendly - sleeps 31

6BR+Spa&Pool+Walk to Clubhouse+Theater+ThemedRooms

Fun Packed 5 Bedroom Villa, Pool/Spa & Game Room

Stunning Disney Lakefront Pool villa + Games Room

Diamond Villa - 20% Off for stays of 7+ nights!

Lakeside villa. Full remodel for 2026. New pool!
Luxury villa rentals

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

Supervilla at Championsgate | Waterpark | Themed

Magical Disney House-Pool & Hot Tub,Free Waterpark

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

The Golden Bear Villa | Private Pool & Theater

Brand New Storey Lake 10 Bedroom Villa with Pool &

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

Walk2Clubhouse|Waterpark|Arcade|Theater|Themed
Villa rentals with a pool

Arcade + Pool Villa • 2.5 Miles to Disney

Family Ready Pool Villa with Star Wars Game Room,

Lakefront Private Pool Villa, 10min to Disney

10BD Bella Vida House Private Pool (BV 287)

Stunning Family-Friendly Home (400995)

Magical Manor | Sleeps 22 | Arcade | Themed Rooms

Sunset Paradise Villa in Orlando, Disney area.

Beautiful 4 bedrooms with South/West facing pool
When is the best time to visit Kissimmee?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £160 | £164 | £185 | £168 | £149 | £171 | £183 | £149 | £137 | £140 | £161 | £192 |
| Avg. temp | 16°C | 18°C | 20°C | 22°C | 25°C | 27°C | 28°C | 28°C | 27°C | 24°C | 20°C | 17°C |
Quick stats about villa rentals in Kissimmee

Total holiday rentals
Explore 710 holiday rentals in Kissimmee

Nightly prices starting at
Kissimmee holiday rentals start at £22 per night before taxes and fees

Verified guest reviews
Over 21,750 verified reviews to help you choose

Family-friendly holiday rentals
700 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 110 rentals that welcome pets

Holiday rentals with a pool
670 properties feature pools

Rentals with dedicated workspaces
430 properties have a dedicated workspace

Wifi availability
710 of Kissimmee holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Kissimmee rentals

4.6 Average rating
Kissimmee stays receive an average rating of 4.6 out of 5 from guests
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- Universal Studios Florida
- Walt Disney World Resort
- Universal Orlando Resort
- Orange County Convention Center
- Disney Springs
- SeaWorld Orlando
- Universal's Volcano Bay
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- Magic Kingdom Park
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- Reunion Resort Golf Courses - Palmer & Watson
- Camping World Stadium
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- Southern Dunes Golf and Country Club
- ChampionsGate Golf Club
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