Holiday rentals with a pool in Lake of Bays

4.88 out of 5 average rating, 102 reviews

A bright living area features a comfortable gray sectional sofa with yellow accent pillows. A round coffee table sits in front, while large windows allow natural light to fill the space. A ceiling fan hangs overhead, and a piece of wall art adds a touch of color.

Condo in Huntsville

Huntsville Lakeside & Ski Chalet

Enjoy the charm of Muskoka lakeside living at our newly renovated, spacious 3-bedroom, 2-bath chalet on stunning Peninsula Lake. Perfect for families seeking a peaceful getaway—no parties permitted. This lake & ski retreat offers three levels of living space, ensuring everyone has their own private area. The loft BR with private bath provides a peaceful escape with stunning views of the lake and ski hills. Enjoy the sandy beach and outdoor pool in summer, and skiing and snowboarding in winter.

4.99 out of 5 average rating, 189 reviews

A glass table is set on a balcony, featuring an ice bucket holding a bottle of sparkling wine, accompanied by two elegant glasses. Soft string lights provide gentle illumination, enhancing the cozy atmosphere. A potted plant adds a touch of greenery.

Condo in Innisfil

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!

Apartment in Blue Mountain Resort Area

An open layout of the studio unit is displayed, featuring a modern kitchen with a breakfast bar and sleek cabinetry. The cozy living area contains a pullout sofa with decorative cushions, and a spacious king bed is situated in the corner, complemented by subtle green accent walls.

4.98 out of 5 average rating, 195 reviews

Evergreen Studio-KingBed/Pool/HotTub/Shuttle

Renovated studio unit at the North Creek Resort featuring: * King Bed * SMART TV, High-Speed Rogers Ignite WIFI and TV * Pull Out Sofa * Stone Fireplace * Modern, Stylish Decor *please note there is not a traditional oven- there is a microwave/convection oven combo along with a stove top *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)

4.97 out of 5 average rating, 145 reviews

Cottage in Tiny

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.

4.98 out of 5 average rating, 145 reviews

The main living area includes a comfortable sectional sofa and an armchair beside the large windows, offering views of the lake. A wooden dining table with matching chairs is centered beneath a lantern. Natural light fills the space, complemented by warm wooden accents.

Townhouse in Huntsville

Lakehill Haven in Hidden Valley Slope and Lakeside

2 bed, 1.5 bath, 2 levels & spectacular views of Peninsula Lake & mountains. Two balconies to relax on. Enjoy a beach, tennis & basketball courts, sauna, hot tub, indoor & outdoor pool included in price next door at Hidden Valley Resort ( has a bar/restaurant). Ski hill across the road has a variety of hills and when ready, an ice rink on the lake for a game of shinny or fun skate. Also a hill for sledding out front! The area also has numerous places to visit. No water equipment provided.

4.94 out of 5 average rating, 156 reviews

A serene balcony overlooks a sparkling lake, surrounded by lush greenery and distant rolling hills. A single adirondack chair is positioned on the wooden deck, inviting relaxation and enjoyment of the peaceful view.

Condo in Huntsville

Your Home Away from Home in Beautiful Huntsville!

Take some time away at this Hidden Valley Hideaway in Huntsville, in Muskoka. Located at the Hidden Valley Resort, next to Deerhurst, this 2-bedroom condominium is perfectly located for all seasons. Winter: Enjoy downhill and cross-country skiing, snowmobile trails, and skating all at your doorstep. Spring/Summer/Fall: Enjoy the beach, water sports, golf, treetop trekking, and so much more. With Arrowhead and Algonquin parks nearby, explore this beautiful part of Ontario!

4.97 out of 5 average rating, 249 reviews

Dome in MONT

Natural Spa: Dome, pool, hot tub, sauna & trails

The Meadow Dome is a private oasis surrounded by 98 acres of gorgeous nature you will have all to yourself. •NEW natural pool •Cedar cabin sauna •Chemical-free hot tub •Walking trails •Indoor fireplace •Outdoor fire pit Close to Algonquin Park Surrounded by thousands of lakes. Meadow Dome is an ideal spot if you want to unwind and enjoy nature at its finest. Meadow Dome is solar powered with wood heating and drinking water provided. There is a close by outhouse.

4.95 out of 5 average rating, 127 reviews

An indoor heated pool is featured, surrounded by wooden paneling and large windows that provide natural light. A comfortable seating area is positioned nearby, along with exercise equipment visible in the background. The clean water reflects the light, enhancing the serene ambiance.

Cottage in Baysville

Muskoka Forest Chalet with a Private Indoor Pool

Welcome to the beautiful Muskoka Forest Chalet. Equipped with a private indoor pool, wood burning fireplace, home gym, fully stocked kitchen, theatre room, new modern furnishings and much more. Escape the city life with a one-of-a-kind recently upgraded cottage. Whether you are coming with family or friends, our cottage provides a fun and relaxing experience for every guest. Enjoy activities nearby including ice fishing, hiking, snowmobile trails or shopping and dining

Apartment in Blue Mountain Resort Area

The airy studio unit features a spacious king bed framed by green accent walls. A cozy sectional sofa is positioned in front of a coffee table. Natural light filters through window shutters, highlighting the adjacent balcony with Muskoka chairs.

4.96 out of 5 average rating, 335 reviews

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)

4.82 out of 5 average rating, 125 reviews

A well-lit outdoor deck is surrounded by snow-covered terrain, featuring patio furniture arranged for relaxation. Warm string lights are hung above, creating a charming atmosphere. A hot tub and barbecue grill are positioned nearby, inviting guests to enjoy the tranquil winter setting.

Cottage in Haliburton

Lakefront Cabin W Hottub, Sauna, Near Sir Sam Ski

Set in quiet wooded hills with private Redstone Lake access, our 5-BR cottage invites slow mornings and feel-good days. Coffee on dock, swims in saltwater pool (June–Sept), long soaks in hot tub, warm moments in sauna, fast wi-fi for movie nights and starry nights by fire pit. Kayaks and paddleboard ready for lake fun. Trails, shops, LCBO 10 and Haliburton 20 mins away. A space thoughtfully curated for you—for JOY, REST, and MEMORIES. Questions? Message us!

Apartment in Blue Mountain Resort Area

An open-concept studio unit is shown, featuring a cozy living area with a dark sectional sofa and a wooden coffee table. The king bed is visible in the background, accompanied by modern bedding. The kitchen area includes a bar with stools and is equipped with countertop appliances.

4.98 out of 5 average rating, 128 reviews

Alpine Bliss: King Bed/Pool/HotTub/Shuttle

Newly renovated studio unit at the mountainside North Creek Resort featuring: * King Bed * SMART TV, High-Speed Rogers Ignite WIFI and TV * Double Pull Out Sofa * Remodeled Washroom *Equipped Kitchen with Keurig * Modern, Stylish Decor *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)!

4.84 out of 5 average rating, 270 reviews

Cottage in Lafontaine

Cozy Beach Cottage with Pool | Georgian Bay

Georgian Bay Beach club. Cute cottage perfect for families, couples, or anyone wanting to relax! 2 bedrooms, 1 bathroom, furnished, pool and private beach on the shores of beautiful Georgian Bay in Tiny township. Cottage is part of a 12 cottage community that shares the pool and beach area. Always super clean, professionally cleaned after every guest! Note: pool is closed October to mid May.

Popular amenities for Lake of Bays rentals with a pool

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

Home in Blue Mountain Resort Area

A spacious bed is adorned with a textured white bedspread and a decorative 'welcome' pillow. Behind the bed, a scenic mural displays misty mountains and lush forests, enhancing the room's atmosphere. Two sleek reading lights are positioned on either side, adding functionality to the space.

4.84 out of 5 average rating, 108 reviews

Cozy Corner Townhome | Shuttle To The Village

Home in Blue Mountain Resort Area

The living area features large windows allowing natural light to illuminate the space. A modern sectional sofa with colorful pillows and a decorative throw faces a sleek coffee table. A cozy fireplace is positioned beneath a wall-mounted TV, creating a warm environment.

4.88 out of 5 average rating, 130 reviews

Blue Mountain Retreat In Historic Snowbridge

4.91 out of 5 average rating, 117 reviews

The entrance features double doors in a dark finish, adorned with elegant seasonal wreaths. Flanking the doors are decorative wall art pieces. A small bistro table with two chairs is positioned on a stone patio, complemented by potted snake plants and decorative pumpkins.

Home in Barrie

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

4.85 out of 5 average rating, 60 reviews

An indoor heated pool area is featured, enclosed with high ceilings and large windows. Comfortable seating is arranged nearby, with a minimalist coffee table in the center. A garage-style door allows for an open transition to the outdoors, enhancing the spacious feel of the room.

Home in Beaverton

Luxury Family Home Indoor Pool Hot Tub Lake Access

4.96 out of 5 average rating, 52 reviews

The exterior of the villa showcases a modern design with a combination of wood and dark paneling. Large glass doors provide access to a patio area, while a well-maintained lawn offers a green space for outdoor activities.

Home in Gravenhurst

Comfort, Luxury and Relaxation

4.94 out of 5 average rating, 35 reviews

Home in Huntsville

Muskoka Farmhouse w/ Family Amenities | +5 Acres

5 out of 5 average rating, 14 reviews

A hot tub is positioned in the foreground, bubbling gently under a twilight sky. In the background, a modern lakefront cottage with extensive glass windows offers views of the surrounding nature. A well-maintained yard features a pathway leading to the cottage and additional outdoor seating.

Home in Victoria Harbour

Sunrise

4.92 out of 5 average rating, 142 reviews

A modern living area features a comfortable sectional sofa and a sleek coffee table, with a fireplace and TV mounted on the wall. A spacious bedroom showcases a king-sized bed and contemporary decor. A private indoor sauna adds a unique wellness element to the condo.

Home in Innisfil

Sauna*King Bed*Fireplace*SmartTV

Condo rentals with a pool

A cozy family room features a spacious gray sectional sofa and a wooden coffee table. Light-colored walls and a patterned rug create a welcoming atmosphere. In the background, a kitchen area is visible, equipped with modern appliances and seating for two.

4.93 out of 5 average rating, 315 reviews

Cozy Studio Mountainside stay in Blue Mountains

A modern kitchen area features blue cabinetry with open shelves displaying neatly arranged dishes. A central island with seating for two is complemented by sleek bar stools. Stainless steel appliances are integrated into the kitchen layout, providing a functional and inviting cooking space.

4.87 out of 5 average rating, 473 reviews

Base of Blue Mountain, Modern Studio

The open concept living area features a modern sofa and armchair arranged around a glass coffee table. A gas fireplace is centered on the wall beneath a mounted TV. Light streams through large windows, illuminating the space.

4.88 out of 5 average rating, 278 reviews

Hidden Haven - Shuttle to the Village & Ski lifts

A bright living area features large windows that allow natural light to fill the space. Comfortable seating is arranged around a central coffee table, with a modern fireplace and a wall-mounted TV providing amenities. Soft, neutral tones dominate the décor, creating a relaxed atmosphere.

4.97 out of 5 average rating, 113 reviews

3 Peaks at Blue Mountains, your luxury staycation!

An open-concept living area is showcased, featuring a cozy sectional sofa and a stone fireplace with a modern TV mounted above. Natural light streams through large windows, illuminating the earthy tones of the decor. A circular wooden coffee table with decorative elements completes the inviting space.

4.91 out of 5 average rating, 139 reviews

Highlands Lodge & Loft - Shuttle to the Village

4.87 out of 5 average rating, 171 reviews

An open-concept kitchen features sleek white cabinetry and a black granite island with three modern bar stools. Natural light fills the space through large glass doors, which lead to a balcony. A minimalistic design with potted plants enhances the welcoming atmosphere.

Condo in Innisfil

Friday Harbor Upscale 1Bed+Sofabed+Pool Option

The studio features a spacious living area with a comfortable sofa and a modern armchair. A king bed adorned with blue and yellow linens is positioned in the background. Natural light filters through the window treatments, enhancing the serene ambiance.

4.83 out of 5 average rating, 433 reviews

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

4.85 out of 5 average rating, 188 reviews

An open-concept living space features modern furnishings and sleek cabinetry. A spacious grey sofa and an accent chair are set around a coffee table. The kitchen area includes stainless steel appliances and a breakfast bar with four stools, creating a warm and functional atmosphere.

Condo in Innisfil

Marina view at Friday Harbour 2bd/2bth Pool option

Other holiday rentals with a pool

Townhouse in Blue Mountain Resort Area

A modern living space features a stone fireplace and large windows that invite natural light. Comfortable seating is arranged around a dark coffee table, and a dining area with a long table is visible. The decor highlights a blend of contemporary style and a cozy atmosphere.

4.89 out of 5 average rating, 171 reviews

The Snowbridge Lookout on Monterra Golf Course

Townhouse in Blue Mountain Resort Area

A spacious living area features tall windows allowing natural light to fill the room. A large screen TV is mounted above a gas fireplace, surrounded by comfortable seating. Decorative pillows enhance the sectional sofa, and an elegant coffee table sits centrally, adding to the inviting atmosphere.

4.97 out of 5 average rating, 230 reviews

Après Blue- 2bed2bath w/Pool 6 min walk to village

4.95 out of 5 average rating, 296 reviews

A wooden dining area features a round table surrounded by four wooden chairs. The kitchen showcases wooden cabinets, a stove, a microwave, and a refrigerator. Natural light enters through a window above the sink, enhancing the warm wood tones of the room.

Cottage in Wasaga Beach

GATED RESORT COTTAGE

4.96 out of 5 average rating, 133 reviews

Guest suite in Keene

Welcome to Paradise on Rice Lake 4-6 month winter

5 out of 5 average rating, 52 reviews

A spacious log home is surrounded by lush greenery, showcasing a blend of natural wood and stone elements. Large windows allow light to enter, and a welcoming path leads to the entrance, framed by vibrant landscaping and towering trees.

Chalet in Mulmur

Into the Woods Log Home

4.95 out of 5 average rating, 19 reviews

Cottage in Burk's Falls

The North Retreat

4.84 out of 5 average rating, 106 reviews

The spacious living area features a comfortable couch and an additional patterned armchair. Two side tables with lamps are present, providing soft lighting. Large windows with sheer curtains allow natural light to fill the room, while a flat-screen TV is mounted on the wall.

Apartment in Shanty Bay

Spacious Hideaway in Nature