Book Luxury Monthly Rentals in Osceola County

We selected the 235 homes worth renting in this location

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Home spotlights in Osceola County

The Blue Dunes

The Blue Dunes

  • 24 guests

  • 10 bedrooms

Polk County, Florida

With a private pool and Jacuzzi, a game loft, and even a twelve-seat cinema, this villa delivers on every front. Calling out for a multi-generational family stay, expect ten en-suite bedrooms – including two themed bunk rooms for little ones – and banquet-worthy dining spaces in the free-flowing living spaces downstairs to gather together.

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 True Joy

A True Joy

  • 28 guests

  • 11 bedrooms

Polk County, Florida

With a private pool, arcade room and movie theatre, this home sets the stage for a fun-filled stay in Florida. You can enjoy long soaks in the spa and there’s an outdoor kitchen for magical evening meals.

The Great Blue Hole

The Great Blue Hole

  • 18 guests

  • 7 bedrooms

Four Corners, Osceola County

This is the perfect vacation home for families looking for a fun-filled getaway. Kids will love the superhero and Fashionista-themed bedrooms, complete with over-the-top bunk beds and decor.


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

Explore the 235 most perfect homes in our collection

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Most popular homes in Osceola County

Harmony's Place

Harmony's Place

  • 12 guests

  • 5 bedrooms

Four Corners, Osceola County

Mickey's Melody

Mickey's Melody

  • 15 guests

  • 5 bedrooms

Osceola County, Florida

The Blue Ledge

The Blue Ledge

  • 18 guests

  • 6 bedrooms

Polk County, Florida

Friends, Family & Fun

Friends, Family & Fun

  • 13 guests

  • 5 bedrooms

Osceola County, Florida

 The Fairy Godmother

The Fairy Godmother

  • 10 guests

  • 4 bedrooms

Osceola County, Florida

Sounds of Fun

Sounds of Fun

  • 34 guests

  • 12 bedrooms

Polk County, Florida

Wondrous Villa

Wondrous Villa

  • 16 guests

  • 6 bedrooms

Four Corners, Osceola County

Lake Escapes

Lake Escapes

  • 4 guests

  • 2 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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