Rent Osceola County Homes with Swimming Pools

We selected the 275 homes worth renting in this location

Who's coming along?

Adults

Age 13+

0

Children

Age 1 to 12

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Infants

Under 1

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Pets

An extra fee may apply

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Home spotlights in Osceola County

Pines & Greenwood

Pines & Greenwood

  • 28 guests

  • 11 bedrooms

Polk County, Florida

This villa is an extravagant mansion located in Orlando, Florida that promises to take guests on a magical journey. The great room features a stylish, contemporary design with sleek and comfy furnishings that are perfect for relaxation and conversation.

So Much Better

So Much Better

  • 34 guests

  • 12 bedrooms

Polk County, Florida

This is a luxurious villa located within a resort. The villa boasts world-class elegance with its Transitional decor and top-quality appliances in the fully equipped kitchen.

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.

Sunflower Sun

Sunflower Sun

  • 6 guests

  • 2 bedrooms

Osceola County, Florida

This brand new vacation rental condo is located in Storey Lake Resort and offers stunning lake views. The condo features two bedrooms and two bathrooms, including a king bedroom on suite and a bedroom with a full over full bunk bed.


We selected the top 3% holiday homes in Osceola County Homes with Swimming Pools

Explore the 275 most perfect homes in our collection

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Most popular homes in Osceola County

Sea View Sanctuary

Sea View Sanctuary

  • 20 guests

  • 7 bedrooms

Osceola County, Florida

Siesta Shade

Siesta Shade

  • 15 guests

  • 5 bedrooms

Loughman, Polk County

Sargasso Seas

Sargasso Seas

  • 7 guests

  • 2 bedrooms

Osceola County, Florida

Sunshine on the Seaside

Sunshine on the Seaside

  • 11 guests

  • 4 bedrooms

Campbell, Osceola County

The Lazy River

The Lazy River

  • 6 guests

  • 2 bedrooms

Osceola County, Florida

Pineview Villa

Pineview Villa

  • 34 guests

  • 12 bedrooms

Polk County, Florida

Sunshine Ranch

Sunshine Ranch

  • 13 guests

  • 5 bedrooms

Osceola County, Florida

Bulletproof Blue

Bulletproof Blue

  • 6 guests

  • 2 bedrooms

Osceola County, Florida

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Check upcoming rates & availability for Osceola County Homes with Swimming Pools


Frequently asked questions

You've certainly come to the right place if you are hoping to find one of the finest Holiday Homes with Swimming Pools in Osceola County, Florida, United States. Our exclusive collection consists solely of homes that have passed our thorough 150-step vetting process with flying colours, so you can book with true peace of mind, knowing that everything from decibel levels in the bedroom to a room's intangible atmosphere has been tested and approved. We don't list a huge number of homes one our site, just the right ones. Each property in our collection comes fully furnished and ready to welcome you, with a fully-equipped kitchen, essential bathroom toiletries, and all linen included. Contact our dedicated team of experts to find the perfect luxury Osceola County Home to Rent with a Swimming Pool today, and set up a holiday to remember.

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