
Family-friendly holiday rentals in Orillia
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Top-rated family-friendly rentals in Orillia
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RELAX @ our HOT TUB and SAUNA in the woods
PLEASE READ! Mt. St. Louis & Horseshoe Valley at doorstep! This is a bright, large and private walk-out GUEST SUITE (basement apartment). Hot tub, patio, fire pit & secluded path in the woods to enjoy nature. Kitchen is equipped with an induction cooktop and all things necessary, even wine bottle opener:) Open concept living room/kitchen/dining room with TV & Roku. Bedroom is a work of Art: dark, mysterious and romantic! Custom Queen bed made from weathered barn wood salvaged from our property.

Four season glamping dome under the stars
Whether you are looking for a romantic getaway for two, a solo remote work week in solitude surrounded by nature, or a family adventure, this 4-season geodesic dome is just the right place. Explore picturesque trails of Scanlon Creek Conservation Area, enjoy inground pool in summer, experience breathtaking sunsets over the farm fields, the starry skies by the bonfire, mesmerizing dance of fireflies in June, and let the frogs and crickets lull you to sleep in the place where time stands still...

Hillside Haven: Serene Studio Retreat for 4
Escape to the serene Carriage Club Resort Studio! Dive into our inviting swimming pool, gather 'round the firepit, or challenge friends to volleyball. Stay active in our modern gym, then explore nearby skiing and golf. Pamper yourself at Vetta SPA or hit mountain biking and hiking trails. Your cozy studio, with a king-size bed and pull-out sofa, sleeps 4 comfortably. Nestled in rolling hills, just a 15-minute drive from Bass Lake's sandy shores. Discover tranquility with a touch of adventure!

Warnica Coach House
Welcome to the Warnica Coach House! This unique and historic property will not disappoint! Built by George R. Warnica in 1900, this spectacular property was the recipient of the Heritage Barrie award in 2018. The Coach House where you will stay, once housed horses and carriages, has been completely renovated top to bottom in 2023 with the finest touches. We are centrally located with a 30 second drive from the 400, and an 8 minute walk to the waterfront, restaurants, and downtown fun.

Orillia TwnHse Oasis w King Bed
Have fun with the whole family at this stylish townhouse oasis. The townhouse features 3 bedrooms, 2.5 bathrooms and 4 beds. The principle bedroom has a king bed, the 2nd bedroom has a queen bed, and the third bedroom has a queen bunk bed (qn bttm, qn top). The house features a large deck with a gas bbq, outdoor dining, and lots of lounging space. Right behind the townhouse is a beautiful nature ravine with lots of trails. Come, enjoy and relax. The property offers super high speed internet.

New Charming tinyhome Experience
Come spend a few days in our warm and cozy hideaway. Enjoy the winter wonderland with some Snow shoeing, cross country skiing or Snowmobiling right from your backyard! OR, perhaps you would like to go to the new Vetta Spa only mins away. Or downhill, snowboard at Horseshoe or Moonstone? OR maybe you just want to disconnect from technology for awhile and reconnect with yourself or loved one. Please inquire if you would like more than 3 guests. The options are plentiful from this location.

Days Away! free parking - no cleaning fee
Welcome to Days Away! Hosted by Lisa and Brad Day. Our city and surrounding areas have so many events, attractions and seasonal activities. We love to explore so we know all the wonderful hidden gems. It is a central/convenient location. We entered hosting because we love to entertain and participate in local events/activities. Whether you are here for sports, attractions, festivals... We want to share this amazing area with you. Come stay with us and let us exceed your expectations!

Waterfront Cottage sauna/golf/kayaks/beach/games
Welcome to Hally’s Cove Riverside Retreat! A fully loaded 4-season escape on the Trent Severn River! Dock your boat with shore power ⚓, lounge in the over-the-water hammock 🌅, relax in the panoramic sauna 🧖♀️, or play in the games room 🕹️ (ping pong, basketball, air hockey plus lots more). Enjoy the 4-hole putting green ⛳, 6 kayaks 🛶, lily pad and custom landscaped Muskoka rock fire pit 🔥. Summer Bonus - Mosquito-sprayed for extra comfort! IG to see more photos: @hallys_cove

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!

Cozy Off-Grid Bunkie on a Horse Farm
Take time away to rejuvenate in nature in our cozy off-grid bunkie on our 25 acre property and horse farm. Our hidden slice of heaven is on outskirts of Orillia, 10 minutes from restaurants, shopping, outings and adventures! Ask us about our Horse Connection experience! Walk our trails, relax with a book, play outdoor games, head to the local beach or enjoy a campfire under the stars.

Cozy getaway for two with hot tub!
Unwind in our peaceful guest suite attached to our home located near Mount St-Louis Moonstone, Vetta Nordic Spa and the cozy town of Coldwater. With its private entrance, hot tub (accessible daily between 8am and 10pm) and serene forest surroundings, this space is designed for guests who value calm, quiet and nature. We ask that guests share our appreciation for a tranquil environment.

Lovely Open Concept Friday Harbor Resort Condo
This is a perfect getaway! Just bring a suitcase and enjoy! Only an hour from Toronto and minutes to Barrie with a resort feel. This condo has a great location with a short walk to grocery store, restaurants, marina etc. → Approx. 700ft² / 65m² of space → Highspeed WIFI! → Beach access → Parking for 1 vehicle → In-unit washer + dryer → Fully equipped kitchen
Popular amenities for Orillia family-friendly rentals
Family-friendly home rentals with a hot tub

Tranquil Retreat private Hot Tub Horseshoe Valley

Riverfront Cottage with HotTub

Lakefront Cozy Cottage w Hot Tub!

Spacious Cottage Escape with Lakeside Hot Tub

CARL in Muskoka: Waterfront Cottage with Hot Tub

Mill Pond Cabin, Nordic Cabin w/ Sauna + Hot-tub

Teremok Log Cabin & Cedar Hot Tub & Sauna on Wood

Couples retreat w/hot tub: Romantic Getaway
Family- and pet-friendly home rentals

A-Frame in the Woods of GeorgianBay, Muskoka

Retreat 82

Luxury, Waterfront, 4 bdrm Bungalow in Sth Muskoka

Serenity, Simplicity and Stone

Tiny House in Penetanguishene

Horseshoe Valley Fieldview Farm

Woodland Muskoka Tiny House

Glass Dome - Sleep Under The Stars- Free Sundays
Family-friendly home rentals with a pool

Farmhouse Guest Suite; Year round hot tub

GATED RESORT COTTAGE

Lake Simcoe Family Stay | 3BR+Rooftop+Pool+Kayaks

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

Mackenzie Cottage

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

Modern Condo at Friday harbour/Pet Friendly

A "Peace" of Eden -- Private suite in country home
Quick stats about holiday rentals that are family-friendly in Orillia
Total rentals
90 properties
Nightly prices starting at
€ 43 before taxes and fees
Total number of reviews
2.8K reviews
Pet-friendly rentals
50 properties allow pets
Rentals with a pool
10 properties have a pool
Rentals with dedicated workspaces
50 properties have a dedicated workspace
Destinations to explore
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- Family-friendly rentals Simcoe County
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- Blue Mountain Village
- Horseshoe Resort
- Snow Valley Ski Resort
- Osler Bluff Ski Club
- Craigleith Ski Club
- Gull Lake
- Devil's Glen Country Club
- Rocky Crest Golf Club
- Angus Glen Golf Club
- Port Carling Golf & Country Club
- The Georgian Peaks Club
- Lakeridge Ski Resort
- Lake Joseph Golf Club
- Mount St. Louis Moonstone
- The Club At Bond Head
- Wooden Sticks Golf Club
- Muskoka Lakes Golf and Country Club
- Bigwin Island Golf Club
- Georgian Bay Islands National Park
- Muskoka Bay Resort
- Windermere Golf & Country Club
- Dagmar Ski Resort
- Barrie Country Club
- The Georgian Bay Club