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

Cute and Cozy House

Large 4 Br - 4.5 Bath; Sauna/Heated Pool/2 King

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

Blue Mountain Retreat w/ Pool + Village Shuttle

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

Pool Open / Serene mountainside home View/Shuttle

Family & Friends Retreat

Comfort, Luxury and Relaxation
Condo rentals with a pool

Blue Mountain Getaway at North Creek Resort

Mountainside Escape at Blue - Outdoor Pool

Cozy Studio Mountainside stay in Blue Mountains

Hidden Haven - Shuttle to Blue / Outdoor Pool

3 Peaks at Blue Mountains, your luxury staycation!

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

2 Bedroom, 2 Level Condo on Blue Mountain!

The Blue Mountain's Dream Escape | Pool | Hot Tub
Other vacation rentals with a pool

Lake/Marina Front, Luxury 2 Storie 1500 Sqft At FH

Luxury Stay at Friday Harbour Resort Lake Simcoe

El Edén, your dream vacation in Simcoe County

Gorgeous Two Bedroom Condo Overlooking Ski Hill

Wildwood HotTub+Indoor/Outdoor Pool+Sauna+GameRoom

Float House on Georgian Bay

Beautiful 2 Bed/2 Bath Condo, Private Balcony

Sweet Memories of Georgian Bay
Quick stats about vacation rentals with a pool in Midland
Total rentals
20 properties
Nightly prices starting at
$96 CAD before taxes and fees
Total number of reviews
450 reviews
Family-friendly rentals
20 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Destinations to explore
- Greater Toronto and Hamilton Area Vacation rentals
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- Cottage rentals Midland
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- Rentals with a hot tub Midland
- Waterfront rentals Midland
- Rentals with a fireplace Midland
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- Apartment rentals Midland
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- Beachfront rentals Midland
- Rentals with a washer and dryer Midland
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- House rentals Midland
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- Rentals with a firepit Midland
- Rentals with a kayak Midland
- Cabin rentals Midland
- Pet-friendly rentals Midland
- Rentals with pools Simcoe County
- Rentals with pools Ontario
- Rentals with pools Canada
- Blue Mountain Village
- Horseshoe Resort
- Snow Valley Ski Resort
- Port Carling Golf & Country Club
- Osler Bluff Ski Club
- Devil's Glen Country Club
- Craigleith Ski Club
- Rocky Crest Golf Club
- Beaver Valley Ski Club
- Mount St. Louis Moonstone
- Lake Joseph 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
- The Georgian Bay Club
- Windermere Golf & Country Club
- Toronto Ski Club
- Alpine Ski Club
- Hawk Ridge Golf & Country Club
- Barrie Country Club
- Heritage Hills Golf Club
- Muskoka Highlands Golf Links