Book Luxury Monthly Rentals in Osceola County

We selected the 256 homes worth renting in this location

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Home spotlights in Osceola County

Pineview Villa

Pineview Villa

  • 34 guests

  • 12 bedrooms

Polk County, Florida

This is a luxurious vacation home located in a resort area. With 71 luxury homes and exclusive amenities, this brand new one-of-a-kind vacation community offers a private entrance, scenic views, and a covered playground.

The Magic of Ketchikan

The Magic of Ketchikan

  • 26 guests

  • 10 bedrooms

Four Corners, Osceola County

This luxurious vacation home has everything you need for a fun-filled family vacation. The game room features seven arcade favorites, while the gaming loft offers pool and giant scrabble competitions, karaoke, and a full bar.

Strawberry Bikini

Strawberry Bikini

  • 18 guests

  • 6 bedrooms

Polk County, Florida

This home is part of a one-of-a-kind vacation community that hosts 71 luxury homes and exclusive amenities. The villa is a brand new home with high-end, lobby-style vibes, adorned in mid-century modern style with sleek yet comfy seating.

Taller Than Life

Taller Than Life

  • 13 guests

  • 4 bedrooms

Osceola County, Florida

This brand new single-family home is perfect for those looking for a luxurious stay in the heart of Orlando. The cozy house features five bedrooms and five bathrooms, with two bedrooms conveniently located on the ground floor.


We selected the top 3% holiday homes in Osceola County Monthly Rentals

Explore the 256 most perfect homes in our collection

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Most popular homes in Osceola County

Take Me to the Ball Game

Take Me to the Ball Game

  • 16 guests

  • 6 bedrooms

Four Corners, Osceola County

Just A Chance

Just A Chance

  • 34 guests

  • 10 bedrooms

Polk County, Florida

The Indian Village

The Indian Village

  • 9 guests

  • 3 bedrooms

Osceola County, Florida

The Old Ore Mine

The Old Ore Mine

  • 6 guests

  • 2 bedrooms

Four Corners, Osceola County

Coral Canyon View Lifestyle

Coral Canyon View Lifestyle

  • 18 guests

  • 5 bedrooms

Polk County, Florida

Pineapple Peach

Pineapple Peach

  • 18 guests

  • 8 bedrooms

Four Corners, Osceola County

A Disney Mania

A Disney Mania

  • 16 guests

  • 6 bedrooms

Four Corners, Osceola County

Sugar Sky

Sugar Sky

  • 24 guests

  • 10 bedrooms

Polk County, Florida

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Frequently asked questions

Discover the ultimate collection of luxury Monthly Rentals in Osceola County, Florida, United States, and say goodbye to all your travel troubles. Here at Plum Guide, it is our promise that each and every home in our range is in the top 3% of homes in its location, so there is no doubting the consistent quality we are able to offer. Secure your extended or short stay today and enjoy the trip of a lifetime in your fully furnished home, with every property on our site including all linens, essential bathroom toiletries, and a perfectly-equipped kitchen. Our meticulous home critics test everything from Wifi speed to a home's design, so you really can trust our judgement. Rent your perfect Osceola County Monthly Apartment today with the help of our team of experts, on standby 24/7 to assist you with absolutely anything.

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