
Holiday rentals with a pool in Tiny
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Tiny
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

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...

Sunny Pines Farm Studio Tennis Court/Bruce Trail
Perfect for a getaway in the country. A bright, spacious, open-concept designer studio featuring beautiful rolling-hill vistas, queen bed, 3-piece bathroom, dedicated bbq, heat/AC plus a wood burning stove, wet bar with a Nespresso machine, deluxe counter-top oven & bar fridge and all new tennis court, laundry available upon request. Mono Cliffs, Boyne Valley, Hockley Valley Nature Reserve Prov. Parks & Mansfield Recreation Centre are minutes away. Ideal hiking, cycling, snowshoeing and xcsking.

Fire & Ice Spa w/ Private Sauna!
Welcome to the most unique suite at Friday Harbour Resort! Relax, refresh and unwind in your very own private spa experience which includes large infrared sauna, 3 indoor fireplaces and outdoor fire table. Kiss those winter blues away while you warm up in the most cozy suite, perfect for a romantic getaway. Every stay includes a bottle of bubbly to toast with the one who is most important to you! Make Fire & Ice your next vacation destination and reconnect in a most romantic, relaxing suite!

Waterfront | Heated Pool, Beachfront, BBQ, AC
Enjoy your morning coffee on your waterfront balcony in your 2 bedroom townhouse, steps away from the beautiful sands of Wasaga Beach. Fall asleep to the rhythmic sounds of the water & watch stunning sunsets from your balcony. Cotton bed linens (680 thread count) & towels included Family friendly with pool & beach- perfect for a summer getaway Located on quiet Beach 4. ~1.5 hr drive from GTA, 20 min to Collingwood/Blue Mountain. 2 parking spots. Perfect for family fun & making new memories!

Utopia villa and spa
Welcome to Utopia B&B, a peaceful retreat where lasting memories are created with family and friends. Just minutes from the beach, grocery stores, gas stations, and all everyday essentials. With so much to enjoy, you may never want to leave! Spend your day savoring good food by the fireplace, relaxing in the hot tub, unwinding in the sauna, and having fun in the game room. Indulge yourself with an unforgettable stay. : No smoking or eating in the hot tub. Any violation will result $500 fine.

Ultimate Georgian Bay Vacation Getaway
Come and stay at our beautifully renovated *all-season* beachfront cottage and enjoy a breathtaking panoramic view of Georgian Bay! You'll discover the cottage sitting atop a sand dune, right on one of the most stunning freshwater beaches in the world. This rare location hosts a private covered deck hovering over the white sand, in a beach house closer to the bay than anywhere else around! Summer guests also enjoy use of a heated salt water pool and large resort deck created by Paul Lafrance.

The Trails Retreat (Private Cabin)
Beautifully renovated 2-story private hilltop cabin for romantic getaway, family stay or friends' retreat, experience a taste of the country together. Backed by forest and trails and set away from our family home, minutes to the Bruce Trail, Hockley Ski & Golf Resort, Mansfield Ski Club and charming Orangeville. Enjoy total guest privacy & spectacular sunrises. Guests are welcome to share our heated pool in season:) Add a playful Yoga/Functional Movement class or chef's dinner to your stay!

Exceptional 2+1 ground floor condo @Friday Harbour
Enjoy early check in and extra late check out in an exceptional 2+1 condo on the ground floor of the desired Aquarius building at Friday Harbour resort. Professionally designed for comfort and style. Aquarius building offers an outdoor pool, BBQ and sitting area. Friday Harbour is an all-season resort, 1 hour north of Toronto, that offers fine dining, LCBO, Starbucks and grocery store within walking distance. Enjoy seasonal activities & events all year round, water sports, live music & more!

Après Blue- 2bed2bath w/Pool 6 min walk to village
Welcome to Apres Blue at Blue Mountain! Unbeatable location @ 110 Fairway Court, only a 5 minute walk to Blue Mountain Village, Ski lifts & Monterra Golf Course. Professionally decorated ground floor unit with full kitchen, gas fireplace, high speed internet, walk out private patio with outdoor dining area, private gas BBQ and shared seasonal pool. This spacious ground floor, 2 bedroom, 2 full bathroom end unit townhouse has everything you need to enjoy your stay! License #LCSTR20230000084

Tiny Home Nestled between Thornbury & Meaford
Tinyhome situated 10 min to Thornbury and Meaford, and 20 min from Blue Mountain Village, nestled a country/residential area so it is quiet and dark at night. Has all the basic comforts including spacious 3 piece bathroom. Close drive to beaches and many hikes and cross country ski trails in the area. It is also a 15 minute drive from Beaver Valley Ski Club and a number of different cideries. Shared heated pool available for the summer months. Window Aircon/pool opens end of May or June.

The Friday Flat | Sunny Escape by the Marina
Enjoy access to all of Friday Harbour's world-class amenities, including a golf course and sandy beach. Take a dip in the outdoor pool and explore the kilometres of scenic walking trails that wind through the Nature Preserve Located just a short drive from Toronto, Friday Harbour offers the perfect escape from city life. Spend your days exploring the shops and restaurants of the promenade, or venture out onto the lake Come experience the ultimate waterfront getaway at Friday Harbour

Studio at Blue-KingBed/Pool/HotTub/Shuttle
Welcome to our studio unit in the mountainside North Creek Resort! *King bed *sofa bed-double sized memory foam mattress *SMART TV, High-Speed Rogers Ignite WIFI and TV *Cookware, Utensils and Keurig *freshly painted *remodeled washroom Property Features: *Shuttle Service *Year Round Hot Tub *Pool (closed for the winter season- to reopen Spring '26) *Tennis Courts *Ski or Hike In/Out to the North Hill (hiking trails, intermediate-advanced daytime skiing)
Popular amenities for Tiny rentals with a pool
House rentals with a pool

Cozy Corner Townhome | Shuttle To The Village

King Bed, Pool, Gym, Ravine View, Your Getaway!

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

Blue Mountain Retreat In Historic Snowbridge

Home away from home with a hot tub and pool

Blue Mountain Village Townhome 4 Bedroom w Shuttle

Heart of Kimberley - with views and a hot tub

The Castle
Apartment rentals with a pool

Cozy Stays – Your Winter Getaway at Friday Harbour

Spacious 1-br w jacuzzi at Horseshoe Valley

Stylish & Spacious 2 Bdrm/2 bths/2 balc Condo Loft

BLUE MOUNTAIN STUDIO OASIS

3 Peaks at Blue Mountains, your luxury staycation!

Cozy & Charming Retreat at Blue Mountain

Ski in/out @ North Creek W King bed! New Hot Tub

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

Cute and Cozy House

HotTub & Fireplace - Headwaters Spring Getaway

Stunning 1BR w Pool ~ Free Parking & Self Check-In

Blue Mountain Escape! Lux 3 bdrm. Hot Tub!

Gorgeous Winfield Chalet Cottage

Cedar Escape • Sauna • 10-Acre Private Forest

Ski, Swim, Soak, Boat & Golf

Sweet Memories of Georgian Bay
Quick stats about holiday rentals with a pool in Tiny

Total holiday rentals
Explore 30 holiday rentals in Tiny

Nightly prices starting at
Tiny holiday rentals start at £38 per night before taxes and fees

Verified guest reviews
Over 1,620 verified reviews to help you choose

Family-friendly holiday rentals
20 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wifi availability
30 of Tiny holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Tiny rentals

4.7 Average rating
Tiny stays receive an average rating of 4.7 out of 5 from guests

Nearby attractions
Tiny’s top spots include Awenda Provincial Park, Balm Beach and Wye Marsh Wildlife Centre
Destinations to explore
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- House rentals Tiny
- Rentals with pools Simcoe County
- Rentals with pools Ontario
- Rentals with pools Canada
- Blue Mountain Village
- Snow Valley Ski Resort
- Mount St. Louis Moonstone
- Beaver Valley Ski Club
- Wasaga Beach Area
- Osler Bluff Ski Club
- Devil's Glen Country Club
- Three Mile Lake
- Georgian Bay Islands National Park
- Scandinave Spa Blue Mountain
- Kee To Bala
- Harrison Park
- Torrance Barrens Dark Sky Conservation Area
- Inglis Falls
- Taboo Muskoka Resort & Golf
- Burl's Creek Event Grounds
- Innisfil Beach Park
- Casino Rama Resort
- Mono Cliffs Provincial Park
- Bass Lake Provincial Park
- Awenda Provincial Park
- Wye Marsh Wildlife Centre
- Centennial Beach
- Orillia Opera House




