
Fitness-friendly vacation rentals in Grey Highlands
Find and book unique fitness-friendly rentals on Airbnb
Top-rated fitness-friendly rentals in Grey Highlands
Guests agree: these fitness-friendly rentals are highly rated for location, cleanliness, and more.

Perch by the Bay - Downtown Midland / Private Loft
Luxury, Comfort & Georgian Bay Style. This first class rental, "Perch By The Bay", is located in Downtown Midland. Walk everywhere, park your car (free) & enjoy what Midland has to offer. Midland's boat harbour, is only minutes by foot. Live our lifestyle, enjoy our many festivals, professional theatre, artisans, culinary cuisine, etc! It's "sister" AirBnB is "Nest By The Bay" private loft at the rear of the building. 2 night min. preferred, 1 night by request. Not suitable for ages under 6

Marina view at Friday Harbour 2bd/2bth Pool option
This Black Cherry model condo is the most sought after layout at Friday harbour, featuring a spacious-well-designed kitchen, living room and balcony area with two bedrooms and two bathrooms ideal for families, couples, or solo travellers. Enjoy comfortable sleeping with a king bed in the master bedroom also featuring an ensuite bath and walking closet, and a Queen bed in the second bedroom. Enjoy a view of the beautiful landscaped courtyard out to the marina while lounging or eating outside.

Ravine Backyard, King Bed, Jacuzzi, Pool, Hot Tub
Forget your worries in this spacious and serene space at Highland Estates. You get a full designer suite perfect for couples, equipped with a King Sized Bed, and a Jacuzzi for romantics. Prepare your own meals in the fully equipped kitchen with Microwave and Electric Stove. Access your favorite Streaming-TV accounts like Netflix, Prime, and Disney+ Close to Vetta Spa and major Ski Hills; literally the Best Retreat in Oro-Medonte. Book with Us Today! Please note the Fireplace isn't working.

Wifi, Free parking, Ski, Kitchen, Laundry, TV, BBQ
Welcome We share with you our ⭐️⭐️⭐️⭐️⭐️ ‘super clean’ and pet friendly home -Free parking, -EV Charger, -Fast Wifi, -Indoor Fireplace (downstairs in the winter months only) -two outdoor fire pits (Solo Stove) -Full Kitchen, -Air Conditioning, -Peloton, -Hot Tub -Loft -Smart TV, -Washer and Dryer Oak Bay Golf Course, large yard, seasonal shared pool. Children's supplies -Crib, -toys, -playmat and custom dog 🐾house Minutes from Georgian Bay Island National Park in Muskoka.

Cozy cottage in the woods near trails & waterfalls
High Pines Cottage is a spacious yet cozy, pet friendly retreat. Located on a beautiful 1.8 acre lot that hosts a variety of large pines and other beautiful trees, it offers privacy and relaxation. It is perfect for any season with many activities from hiking to skiing and has a home gym. Whether you are looking to curl up by the fireplace or enjoy the trails with your pup, our cottage offers what you need to unwind or connect with friends and family. Check out Instagr. @high_pines_cottage

Lovely king size room with kitchenette
An inviting four-season natural playground surrounded by rolling hills and forested trails is located in a spectacular country setting. The Mount St. Louis Moonstone Ski Area is 12 km away, Barrie is 25 km away, and Toronto is 138 km away. Onsite amenities include a pool, fitness center, fire pit, and play area. Nearby, you can enjoy an array of fun attractions and activities for every season! Several convenient perks are available to provide you with the best and most comfortable stay.

Mono — Cabin in the Woods Experience
This cozy cabin in the woods is perfect for content creation, photography, proposals or just enjoying nature and swimming in the summer or ice skating throughout the winter. Only minutes from Orangeville, Hockley Valley and less than one hour from downtown Toronto you feel hours away from everything. Swim in your private pond, recharge and escape the noise of the city and relax in your own personal paradise! Cabinonthe9 is one of Canada's top short term rental destinations.

Blue Mountain Village Townhome w Free Shuttle
Blue Mountain STA Licence # LCSTR20220000118 Brand New 3 Bedroom Executive Town-home in Historic Snowbridge that can sleep 10-Comfortably. Full Kitchen, Washer & Dryers, Garage, Parking and Free Shuttle Service to the Village and Skiing 24 hrs per day on demand and Free. Please note due to the Free 24 hrs Shuttle Service that we consider this Townhome to be Ski in & Ski out as the service will take you do and from Skiing to the Front Door of the Townhome.

Spacious 1-br w jacuzzi at Horseshoe Valley
Welcome to Horseshoe Valley, just 1.5 hrs north of Greater Toronto Area. It's a four-season wonder of nature with limitless access to lakes, rivers, trails, and rolling hills. Whether you aim to ski in snow-laden forests of pine, hit golf at one of eighteen golf courses, mountain bike or hike in several landscape trails, soak in the healing experience of Vetta Nordic spa, or simply relax at the tranquility of the area, this place is simply yours to enjoy!

Bayview Oasis: Luxe Lakeside Escape w/ Pickleball
Welcome to Bayview Oasis, our luxurious lake house on Georgian Bay. Enjoy breathtaking water views, a modern kitchen with high-end appliances, a cozy basement with a pool table and bar, and a master suite with top-notch amenities. Outdoors, relax in the cabana with a pizza oven, fireplace, picnic tables, spacious patio, hot tub, and our new custom pickleball court. Whether it's a romantic getaway or family vacation, Bayview Oasis is the perfect retreat.

Pet-friendly, 1 BR condo in Horseshoe Valley
All-season Condominium in Horseshoe Valley. Spacious BR with ensuite. Living room with fireplace, dining space, sofa bed. Private balcony, kitchen with all the necessities. Walk to the new Vetta Nordic Spa. Skiing , golfing , hiking & biking trails, treetop trekking, restaurants, groceries- 5 min drive Barrie , Orillia , Wassaga beach are 20 min. drive( beach #3 is PET FRIENDLY) Please note: we are NOT able to accept cats!

Cozy 1-Bedroom Romantic Retreat with full Kitchen
Escape to Carriage Club Resort, nestled on rolling hills near Horseshoe Valley. Our 1-bedroom vacation rental sleeps 4 with a king-size bed and pull-out sofa. Enjoy the pool, firepit, volleyball, gym, and nearby skiing, golf, and Vetta SPA. Explore hiking trails, high ropes, and a 15-minute drive to Bass Lake's beach. Experience adventure and relaxation at Carriage Club!
Popular amenities for Grey Highlands fitness-friendly rentals
Fitness-friendly apartment rentals

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

#1A Small Town Escape 1BR *weekly/monthly stays

Luxury Cottage - The Pine Loft

Highland Hidey Hole-Resort Amenities, Pet friendly

Private Balcony Suite with Jacuzzi Off of Bedroom!

Stylish 1 bedroom Pet friendly Condo by Sage Homes

Gym+Pool+PetFriendly+KingBeds

Jr Club Suite: Kitchenette, Pool, HotTub, Gym, BBQ
Fitness-friendly condo rentals

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

Convenient Garden Walkout to Pier, 2BR+2bath Condo

Lux 2BD Apartment in Horseshoe Valley, Oro-Medonte

Cozy Studio + Kitchenette & 1 Free Parking

Serenity 1Bed+Sauna+HotTub+Indoor/OutdoorPool

Resort Condo (2 suites) near Horseshoe Valley

Private 2BR Condo | 4 Beds+Pool+Resort

Enjoy the City Skyline View with Pool & Gym
Fitness-friendly house rentals

Luxury Home Blue Rose Chalet Hill View & Hot Tub

3 bedroom apartment

Underhill Riverside Retreat-Nature Preserve

4 Bedroom Fully Private Townhouse in Barrie

Birdsong, the perfect Blue Mountains getaway

Wasaga Residency

Stunning 3 Bdrm Home W/ Hot Tub, Sauna, Gym!

Luxurious Lake House for Family Stays
Quick stats about vacation rentals that are fitness-friendly in Grey Highlands
Total rentals
160 properties
Nightly prices starting at
€ 34 before taxes and fees
Total number of reviews
4.1K reviews
Family-friendly rentals
130 properties are a good fit for families
Pet-friendly rentals
60 properties allow pets
Rentals with a pool
100 properties have a pool
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- Blue Mountain Village
- Cobble Beach Golf Resort Community
- Horseshoe Resort
- Snow Valley Ski Resort
- Beaver Valley Ski Club
- Osler Bluff Ski Club
- Craigleith Ski Club
- Devil's Glen Country Club
- Hockley Valley Resort - Golf, Spa and Ski
- The Georgian Peaks Club
- TPC Toronto at Osprey Valley
- Mount St. Louis Moonstone
- The Club At Bond Head
- Caledon Country Club
- Barrie Country Club
- The Georgian Bay Club
- Alpine Ski Club
- Toronto Ski Club
- Mansfield Ski Club
- Legacy Ridge Golf Club
- Heritage Hills Golf Club
- Inglis Falls
- National Pines Golf Club
- Horseshoe Adventure Park