Book Luxury Monthly Rentals in Osceola County

We selected the 277 homes worth renting in this location

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Home spotlights in Osceola County

Siesta Shade

Siesta Shade

  • 15 guests

  • 5 bedrooms

Loughman, Polk County

This luxurious new single-family home boasts six bedrooms, six bathrooms, and a game room complete with air hockey, pool table, and ping pong. The first floor features one suite while the second floor has two suites and a spacious loft.

A Little Piece of Sunshine

A Little Piece of Sunshine

  • 28 guests

  • 11 bedrooms

Polk County, Florida

This villa is a luxurious and spacious 7,200-square-foot mansion in Orlando, Florida. This stunning property boasts a chef's kitchen with black marble countertops and upgraded appliances, an adjacent versatile dining room, and a beautiful great room with modern couches and chairs.

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.

Sunshine Ranch

Sunshine Ranch

  • 13 guests

  • 5 bedrooms

Osceola County, Florida

This brand new 5-bedroom, 4-bathroom vacation rental with a pool is located in the Storey Lake Resort, providing an unforgettable vacation. The bedrooms consist of two king bedrooms, one king suite, one bedroom with a full and twin bed, and one bedroom with a bunk bed twin over full with a twin trundle bed.


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

Explore the 277 most perfect homes in our collection

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Most popular homes in Osceola County

Black & White Paradise

Black & White Paradise

  • 4 guests

  • 2 bedrooms

Osceola County, Florida

Old Folks At Home

Old Folks At Home

  • 34 guests

  • 10 bedrooms

Polk County, Florida

The Magic of Disney

The Magic of Disney

  • 18 guests

  • 8 bedrooms

Four Corners, Osceola County

The Old Cabin

The Old Cabin

  • 10 guests

  • 4 bedrooms

Four Corners, Osceola County

Just Another Day At The Beach

Just Another Day At The Beach

  • 18 guests

  • 7 bedrooms

Four Corners, Osceola County

Sargasso Seas

Sargasso Seas

  • 7 guests

  • 2 bedrooms

Osceola County, Florida

The Great Blue Hole

The Great Blue Hole

  • 18 guests

  • 7 bedrooms

Four Corners, Osceola County

Take Me to the Ball Game

Take Me to the Ball Game

  • 16 guests

  • 6 bedrooms

Four Corners, Osceola County

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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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