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Osceola County Villas Guide

Escape to Osceola County, Florida, where sun-kissed beaches, tranquil lakes, and warm hospitality await your villa holiday.

Villas in Osceola County

4 Bedroom Executive Home with Private Pool and Spa
£185  night
8
4
3
Details View Offers
“3 MILES TO DISNEY’S MAIN GATE” 5⭐️ 4BD 3BTH HOME with SOUTH FACING POOL+GAME RM
4.9/5
£109  night
10
5
3
Details View Offers
Pool home 15 minutes drive to Disney in Emerald Island Resort
4.0/5
£150  night
14
7
6
Details View Offers
Sprawling Private Pool Home near Disney wSprawling Private Pool Home near Disney w/ Pond Views & Game Room/ Pond Views & Game Room
3.5/5
£193  night
14
7
4
Details View Offers
Last Minute Disney Getaway! Private Pool, Hot Tub & Games Room. Book Now! #109541
£399  night
16
6
6
Details View Offers
5 Star Villa on Orlando’s most Exclusive Reunion Resort and Spa, Orlando Villa 4599
£474  night
12
5
5
Details View Offers
Last Minute Disney Getaway! Private Pool, Hot Tub & Games Room. Book Now! #15116
£166  night
13
5
3
Details View Offers
PeRfEcT! 5PeRfEcT! 5/5 w/private Pool/Spa 20min to DiSnEy/5 wPeRfEcT! 5/5 w/private Pool/Spa 20min to DiSnEy/private PoolPeRfEcT! 5/5 w/private Pool/Spa 20min to DiSnEy/Spa 20min to DiSnEy
£242  night
11
5
5
Details View Offers
Amazing Champions Gate 8 Bedroom 5 Bathroom Villa
4.3/5
£250  night
19
8
5
Details View Offers
Luxury Villa Estate wLuxury Villa Estate w/ One-of-a-kind Theme Bedrooms at Reunion Resort/ One-of-a-kind Theme Bedrooms at Reunion Resort
5.0/5
£1181  night
28
8
10
Details View Offers
Amazing 6 BD 6BA Luxury Villa Champions Gate
3.0/5
£286  night
15
6
6
Details View Offers
9 Miles to Disney! 8 Br9 Miles to Disney! 8 Br/6 Ba Villa with Pool/Game/Patio/6 Ba Villa with Pool9 Miles to Disney! 8 Br/6 Ba Villa with Pool/Game/Patio/Game9 Miles to Disney! 8 Br/6 Ba Villa with Pool/Game/Patio/Patio
4.0/5
£206  night
16
8
6
Details View Offers
Dream Weaver Villa® - Blooming Alamanda - Lakefront - Disney - Pool & Spa Heated
5.0/5
£132  night
8
4
2
Details View Offers
Last Minute Disney Getaway! Private Pool, Hot Tub & Games Room. Book Now! #21748
5.0/5
£120  night
8
4
3
Details View Offers
Last Minute Disney Getaway! Private Pool, Hot Tub & Games Room. Book Now! #15156
£231  night
12
6
5
Details View Offers
Windsor Palms Retreat: Pool, Resort Access & Minutes to Disney
4.7/5
£104  night
8
4
3
Details View Offers
Splendid Villa Solara 6BedSplendid Villa Solara 6Bed/5Bath/Pool/Jacuzzi/18 Min From Disney/5BathSplendid Villa Solara 6Bed/5Bath/Pool/Jacuzzi/18 Min From Disney/PoolSplendid Villa Solara 6Bed/5Bath/Pool/Jacuzzi/18 Min From Disney/JacuzziSplendid Villa Solara 6Bed/5Bath/Pool/Jacuzzi/18 Min From Disney/18 Min From Disney
3.0/5
£283  night
16
6
5
Details View Offers
Orlando BeachHouse ❤️ Expanded pool deck & HotTub Recent renos, close to Disney!
5.0/5
£128  night
8
4
2
Details View Offers
3 bed 2 bath Single Level Villa. Only 5 miles west of Disney's Main Gate!
4.5/5
£82  night
6
3
2
Details View Offers
Fabulous South Facing Lakeside Villa with Private Pool
4.7/5
£110  night
8
4
2
Details View Offers

Why a holiday villa in Osceola County

Osceola County, Florida is a treasure trove of sunshine and adventure, making it the perfect destination for your next villa holiday. With its beautiful lakes, rolling hills, and sparkling beaches, you'll find endless opportunities to soak up the sun, explore the great outdoors, and experience the authentic charm of small-town America.

From relaxing by the pool or taking a leisurely boat ride on Lake Tohopekaliga to exploring the vibrant city of Kissimmee, there's something for everyone in Osceola County. Whether you're traveling with family, friends, or that special someone, our villas offer the perfect blend of comfort, convenience, and luxury to make your holiday truly unforgettable.

Osceola County is also steeped in history and culture, with a rich heritage that's waiting to be discovered. Visit the Osceola County Historical Society Museum to learn about the area's fascinating past, or take a stroll along the shores of Lake Tohopekaliga to enjoy the scenic views and peaceful atmosphere. With its unique blend of urban excitement and natural beauty, Osceola County is the ideal destination for your next villa holiday.

When to rent a villa in Osceola County

When it comes to planning your villa holiday in Osceola County, Florida, timing is everything. If you're looking for warm weather and sunshine, winter (December to February) is a great time to visit, with average highs in the mid-70s to low 80s Fahrenheit (23-27°C). The dry season has just begun, making it perfect for outdoor activities like fishing, hiking, or simply lounging by the pool. And if you're lucky, you might even catch a glimpse of the beautiful winter blooms that dot the landscape.

If you prefer warmer weather and don't mind the occasional summer storm, June to September is another great time to visit Osceola County. The temperatures soar into the mid-90s Fahrenheit (35-37°C), but the beachgoers love it! And if you're not a fan of heat, consider visiting in the spring (March to May) or fall (October to November), when the weather is mild and pleasant, with average highs in the 70s and 80s Fahrenheit (21-27°C). Just be aware that these periods are peak tourist season, so expect larger crowds and potentially higher prices for villas. Whatever time of year you choose, Osceola County promises to deliver a sunny and memorable villa holiday experience!

Where to go in Osceola County

From the bustling streets of Kissimmee to the tranquil shores of Lake Tohopekaliga, Osceola County offers a diverse range of experiences and landscapes that will suit every taste and preference. If you're looking for a vibrant nightlife, head to downtown Kissimmee, where you'll find a lively mix of bars, clubs, and restaurants that are perfect for letting loose with friends or family. Alternatively, if you prefer a more relaxed atmosphere, consider staying in the quiet town of Celebration, which is known for its picturesque canals, quaint shops, and mouth-watering eateries.

For those seeking sun-kissed bliss, head to the shores of Lake Tohopekaliga or the beaches along the Kissimmee River, where you can enjoy water sports, fishing, or simply bask in the warm Florida sunshine. And if you're a foodie, be sure to explore the many restaurants and cafes that serve up delicious Southern cuisine, fresh seafood, and international flavors. With its unique blend of urban excitement and natural beauty, Osceola County has something for everyone - so why not come and discover it for yourself?

Picture of two young girls swimming in a pool with their floatation rings
Family friendly villas
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Image of a woman swimming in a pool at a holiday home
Private pool villas
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Picture of a Titleist golf ball on the edge of the hole on a golfing green
Villas near golf course
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Discover regions within Osceola County

Kissimmee
Kissimmee
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Kissimmee
Kissimmee
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Villas in Osceola County

4 Bedroom Executive Home with Private Pool and Spa
£185  night
8
4
3
Details View Offers
“3 MILES TO DISNEY’S MAIN GATE” 5⭐️ 4BD 3BTH HOME with SOUTH FACING POOL+GAME RM
4.9/5
£109  night
10
5
3
Details View Offers
Pool home 15 minutes drive to Disney in Emerald Island Resort
4.0/5
£150  night
14
7
6
Details View Offers
Sprawling Private Pool Home near Disney wSprawling Private Pool Home near Disney w/ Pond Views & Game Room/ Pond Views & Game Room
3.5/5
£193  night
14
7
4
Details View Offers
Last Minute Disney Getaway! Private Pool, Hot Tub & Games Room. Book Now! #109541
£399  night
16
6
6
Details View Offers
5 Star Villa on Orlando’s most Exclusive Reunion Resort and Spa, Orlando Villa 4599
£474  night
12
5
5
Details View Offers
Last Minute Disney Getaway! Private Pool, Hot Tub & Games Room. Book Now! #15116
£166  night
13
5
3
Details View Offers
PeRfEcT! 5PeRfEcT! 5/5 w/private Pool/Spa 20min to DiSnEy/5 wPeRfEcT! 5/5 w/private Pool/Spa 20min to DiSnEy/private PoolPeRfEcT! 5/5 w/private Pool/Spa 20min to DiSnEy/Spa 20min to DiSnEy
£242  night
11
5
5
Details View Offers
Amazing Champions Gate 8 Bedroom 5 Bathroom Villa
4.3/5
£250  night
19
8
5
Details View Offers
Luxury Villa Estate wLuxury Villa Estate w/ One-of-a-kind Theme Bedrooms at Reunion Resort/ One-of-a-kind Theme Bedrooms at Reunion Resort
5.0/5
£1181  night
28
8
10
Details View Offers
Amazing 6 BD 6BA Luxury Villa Champions Gate
3.0/5
£286  night
15
6
6
Details View Offers
9 Miles to Disney! 8 Br9 Miles to Disney! 8 Br/6 Ba Villa with Pool/Game/Patio/6 Ba Villa with Pool9 Miles to Disney! 8 Br/6 Ba Villa with Pool/Game/Patio/Game9 Miles to Disney! 8 Br/6 Ba Villa with Pool/Game/Patio/Patio
4.0/5
£206  night
16
8
6
Details View Offers
Dream Weaver Villa® - Blooming Alamanda - Lakefront - Disney - Pool & Spa Heated
5.0/5
£132  night
8
4
2
Details View Offers
Last Minute Disney Getaway! Private Pool, Hot Tub & Games Room. Book Now! #21748
5.0/5
£120  night
8
4
3
Details View Offers
Last Minute Disney Getaway! Private Pool, Hot Tub & Games Room. Book Now! #15156
£231  night
12
6
5
Details View Offers
Windsor Palms Retreat: Pool, Resort Access & Minutes to Disney
4.7/5
£104  night
8
4
3
Details View Offers
Splendid Villa Solara 6BedSplendid Villa Solara 6Bed/5Bath/Pool/Jacuzzi/18 Min From Disney/5BathSplendid Villa Solara 6Bed/5Bath/Pool/Jacuzzi/18 Min From Disney/PoolSplendid Villa Solara 6Bed/5Bath/Pool/Jacuzzi/18 Min From Disney/JacuzziSplendid Villa Solara 6Bed/5Bath/Pool/Jacuzzi/18 Min From Disney/18 Min From Disney
3.0/5
£283  night
16
6
5
Details View Offers
Orlando BeachHouse ❤️ Expanded pool deck & HotTub Recent renos, close to Disney!
5.0/5
£128  night
8
4
2
Details View Offers
3 bed 2 bath Single Level Villa. Only 5 miles west of Disney's Main Gate!
4.5/5
£82  night
6
3
2
Details View Offers
Fabulous South Facing Lakeside Villa with Private Pool
4.7/5
£110  night
8
4
2
Details View Offers