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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

Last Minute Disney Getaway! Private Pool, Hot Tub & Games Room. Book Now! #100817
£380  night
18
9
7
Details View Offers
5 BED | 4 BATH Amazing Villa w5 BED | 4 BATH Amazing Villa w/ Gamesroom & POOL 7387Oak/ Gamesroom & POOL 7387Oak
5.0/5
£151  night
12
5
4
Details View Offers
LUXURY 4 BEDROOM 3 BATH IN GATED EMERALD ISLAND RESORT
5.0/5
£121  night
8
4
3
Details View Offers
Fantastic 5 Bedroom Champions Gate Resort Home With Spa and Pool
£176  night
10
5
5
Details View Offers
2021 BRAND NEW LUXURY 7 BR CLOSE DISNEY&THEMED ,6
£267  night
14
7
6
Details View Offers
6 bedroom 5 bathroom with Spa and Games Room Brand New Modern Furnishings
£123  night
12
6
5
Details View Offers
Ultimate Bespoke 6 Bedroom Champions Gate Pool Villa
£133  night
14
6
5
Details View Offers
The Secret to Enjoying a Villa Holiday of a Lifetime to Reunion Resort, Villa Orlando 2018
£378  night
10
5
5
Details View Offers
Large spacious 5 bed 5 bath home with no rear neighbors and themed bedrooms
5.0/5
£189  night
12
5
5
Details View Offers
Enchanted 9BR Villa | Disney Fun Awaits
3.7/5
£277  night
23
9
5
Details View Offers
Wynstone Elegance | Screened Pool, Summer Kitchen & Games Room
3.8/5
£313  night
14
7
6
Details View Offers
❤ of Champions Gate ✦Pool ✦King Bed ✦20min→Disney
£125  night
10
4
3
Details View Offers
Built For Vacation | South-Facing, Large Screen Pool, Splash Pad, Game,Movie Room
4.7/5
£825  night
20
8
8
Details View Offers
Vacationer's Delight | 5BR, Private Movie Theater, Golf Course View
£292  night
16
5
6
Details View Offers
6 Bed Amazing Pool6 Bed Amazing Pool/Spa Combo With Privacy In Back/Spa Combo With Privacy In Back
£243  night
14
6
4
Details View Offers
Skylight Ceiling Cinema! Brand New Luxury 12BRSkylight Ceiling Cinema! Brand New Luxury 12BR/11.5BA Pool Villa Near Disney/11.5BA Pool Villa Near Disney
1.0/5
£506  night
28
12
12
Details View Offers
Stunning Sunsets & Private Pool | 7BD Dream Villa
3.7/5
£141  night
16
7
7
Details View Offers
Lake view *Disney->20min *Paradise Palms 5BDLake view *Disney->20min *Paradise Palms 5BD/5BA/5BA
£211  night
12
5
5
Details View Offers
Last Minute Disney Getaway! Private Pool, Hot Tub & Games Room. Book Now! #60457
£270  night
10
5
4
Details View Offers
10 min to Disney, private pool home on luxury resort, brand new hardwood floors.
4.7/5
£371  night
22
10
10
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

Last Minute Disney Getaway! Private Pool, Hot Tub & Games Room. Book Now! #100817
£380  night
18
9
7
Details View Offers
5 BED | 4 BATH Amazing Villa w5 BED | 4 BATH Amazing Villa w/ Gamesroom & POOL 7387Oak/ Gamesroom & POOL 7387Oak
5.0/5
£151  night
12
5
4
Details View Offers
LUXURY 4 BEDROOM 3 BATH IN GATED EMERALD ISLAND RESORT
5.0/5
£121  night
8
4
3
Details View Offers
Fantastic 5 Bedroom Champions Gate Resort Home With Spa and Pool
£176  night
10
5
5
Details View Offers
2021 BRAND NEW LUXURY 7 BR CLOSE DISNEY&THEMED ,6
£267  night
14
7
6
Details View Offers
6 bedroom 5 bathroom with Spa and Games Room Brand New Modern Furnishings
£123  night
12
6
5
Details View Offers
Ultimate Bespoke 6 Bedroom Champions Gate Pool Villa
£133  night
14
6
5
Details View Offers
The Secret to Enjoying a Villa Holiday of a Lifetime to Reunion Resort, Villa Orlando 2018
£378  night
10
5
5
Details View Offers
Large spacious 5 bed 5 bath home with no rear neighbors and themed bedrooms
5.0/5
£189  night
12
5
5
Details View Offers
Enchanted 9BR Villa | Disney Fun Awaits
3.7/5
£277  night
23
9
5
Details View Offers
Wynstone Elegance | Screened Pool, Summer Kitchen & Games Room
3.8/5
£313  night
14
7
6
Details View Offers
❤ of Champions Gate ✦Pool ✦King Bed ✦20min→Disney
£125  night
10
4
3
Details View Offers
Built For Vacation | South-Facing, Large Screen Pool, Splash Pad, Game,Movie Room
4.7/5
£825  night
20
8
8
Details View Offers
Vacationer's Delight | 5BR, Private Movie Theater, Golf Course View
£292  night
16
5
6
Details View Offers
6 Bed Amazing Pool6 Bed Amazing Pool/Spa Combo With Privacy In Back/Spa Combo With Privacy In Back
£243  night
14
6
4
Details View Offers
Skylight Ceiling Cinema! Brand New Luxury 12BRSkylight Ceiling Cinema! Brand New Luxury 12BR/11.5BA Pool Villa Near Disney/11.5BA Pool Villa Near Disney
1.0/5
£506  night
28
12
12
Details View Offers
Stunning Sunsets & Private Pool | 7BD Dream Villa
3.7/5
£141  night
16
7
7
Details View Offers
Lake view *Disney->20min *Paradise Palms 5BDLake view *Disney->20min *Paradise Palms 5BD/5BA/5BA
£211  night
12
5
5
Details View Offers
Last Minute Disney Getaway! Private Pool, Hot Tub & Games Room. Book Now! #60457
£270  night
10
5
4
Details View Offers
10 min to Disney, private pool home on luxury resort, brand new hardwood floors.
4.7/5
£371  night
22
10
10
Details View Offers