Book Luxury Monthly Rentals in Osceola County

We selected the 313 homes worth renting in this location

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Home spotlights in Osceola County

Sugar Sky

Sugar Sky

  • 24 guests

  • 10 bedrooms

Polk County, Florida

This Orlando villa is the perfect family vacation home, with plenty of entertainment options for kids and adults alike. The themed bedrooms are a hit with the little ones, including a toy room and basketball-themed bedroom complete with over-the-top bunk beds.

Black & White Paradise

Black & White Paradise

  • 4 guests

  • 2 bedrooms

Osceola County, Florida

This brand new vacation rental condo is located in the beautiful Storey Lake Resort and is perfect for a family or group of friends. With two bedrooms and two bathrooms, this condo comfortably accommodates up to four guests.

Under the Sea Escape

Under the Sea Escape

  • 12 guests

  • 6 bedrooms

Polk County, Florida

If you're looking for a family-friendly vacation rental near Disney World, look no further than this stunning home in the Solterra Resort. With its pirate-themed bunk room, Star Wars arcade, and sports-themed den, this home has something for everyone.

Pineapple Peach

Pineapple Peach

  • 18 guests

  • 8 bedrooms

Four Corners, Osceola County

One thing’s for sure in this Floridian home – you’ll never be bored. Jam-packed with entertainment options including a home cinema, games room, private pool and hot tub, there’s something for everyone here.


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

Explore the 313 most perfect homes in our collection

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Most popular homes in Osceola County

The Great Blue Hole

The Great Blue Hole

  • 18 guests

  • 7 bedrooms

Four Corners, Osceola County

Sea View Sanctuary

Sea View Sanctuary

  • 20 guests

  • 7 bedrooms

Osceola County, Florida

The Magic of Ketchikan

The Magic of Ketchikan

  • 26 guests

  • 10 bedrooms

Four Corners, Osceola County

Summer's Insomniac Dream

Summer's Insomniac Dream

  • 10 guests

  • 4 bedrooms

Osceola County, Florida

The Old Cabin

The Old Cabin

  • 10 guests

  • 4 bedrooms

Four Corners, Osceola County

Lemon Blue

Lemon Blue

  • 26 guests

  • 10 bedrooms

Four Corners, Osceola County

A Disney Mania

A Disney Mania

  • 16 guests

  • 6 bedrooms

Four Corners, Osceola County

A History of the Sun

A History of the Sun

  • 10 guests

  • 4 bedrooms

Osceola 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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