
Holiday rentals with a pool in Orillia
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Orillia
Guests agree: These homes with a pool are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Orillia rentals with a pool
House rentals with a pool

Cute and Cozy House

2 Bd Boardwalk Condo Patio Oasis

Our vacation home. Fully equipped. Pool. Fire Pit.

Home away from home with a hot tub and pool

Luxurious 4BDRM-King Bed-Barrie-near Snow Resorts

Hockley Valley - Jazzy Pines - 4 BR with Pool

Beautiful Waterfront Cottage with Pool&HomeTheater

Luxury Resort Villa on Muskoka Bay Golf Course
Condo rentals with a pool

Beautiful Condo, 2 Bedrooms and a Den in a Resort!

Modern elegance Aquarius Fri Harb

Sunsets by the Lake at 2BR 2BA Condo in Innisfil

Spectacular 2 BDRM Penthouse at Friday Harbour

Friday Harbour Luxury Condo Escape, Sleeps 4

Lake Simco penthouse at Friday Harbour resort

Private 2BR Condo | 4 Beds+Pool+Resort

FH Harbour Flats 2BR 2BA- Every Day is Friday
Other holiday rentals with a pool

Summer Escape at Friday Harbour

Oro-Medonte/(ski),in/out pool 1

NEW Ski-In Ski-Out 1-BED Condo - Pool, Gym, Sauna

Your Dream Escape at Friday Harbour - 2Bdrm 2Bath

El Edén, your dream vacation in Simcoe County

Modern Luxury Delight with a Pool and Hot Tub

Trendy 1 Bdrm w/Pool & Hot Tub View

Rustic luxury chalet near beach with private pool
Quick stats about holiday rentals with a pool in Orillia
Total rentals
10 properties
Nightly prices starting at
$122 AUD before taxes and fees
Total number of reviews
410 reviews
Family-friendly rentals
10 properties are a good fit for families
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wi-Fi availability
10 properties include access to Wi-Fi
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- Rentals with pools Simcoe County
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- Blue Mountain Village
- Horseshoe Resort
- Snow Valley Ski Resort
- Port Carling Golf & Country Club
- Osler Bluff Ski Club
- Gull Lake
- Devil's Glen Country Club
- Craigleith Ski Club
- Angus Glen Golf Club
- Rocky Crest Golf Club
- Lakeridge Ski Resort
- Mount St. Louis Moonstone
- Lake Joseph Golf Club
- Bigwin Island Golf Club
- Wooden Sticks Golf Club
- The Club At Bond Head
- Muskoka Lakes Golf and Country Club
- The Georgian Peaks Club
- Muskoka Bay Resort
- Georgian Bay Islands National Park
- Dagmar Ski Resort
- The Georgian Bay Club
- Windermere Golf & Country Club
- Toronto Ski Club