Holiday rentals with a pool in Lake of Bays

Guest suite in Kawartha Lakes

The exterior of a well-maintained home is captured, surrounded by lush greenery and flower beds. A stone pathway leads to the entrance, which features a covered porch with large windows. Colorful flowers add vibrancy to the garden area, complemented by a serene natural setting.

4.98 out of 5 average rating, 398 reviews

A "Peace" of Eden -- Private suite in country home

Quiet country setting surrounded by forest and farmland, bordering on the Altberg Wildlife Sanctuary Nature Reserve. Lower level suite with private entrance includes one separate bedroom, one bed with room divider in the common space, plus a full bath, kitchen facilities, and living area. Once called the "United Nations of birds", we are just a short drive from public beaches, lakes, the Victoria Rail Trail, and Monck's Landing Golf Course (stay and play package available). Fabulous star-gazing!

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.

4.99 out of 5 average rating, 175 reviews

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!

4.96 out of 5 average rating, 135 reviews

A peaceful beach scene captures the soft sand shoreline leading to the water's edge. Gentle waves lap at the shore, and the sky is filled with warm sunset hues. A cottage is visible in the background, nestled among trees, enhancing the serene atmosphere.

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, 142 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.

A serene bedroom features a dark headboard positioned against light gray walls. Three botanical prints hang above a cozy bed with soft blue bedding. On either side, glass lamps provide gentle illumination, and a potted plant adds a touch of greenery near the window.

4.93 out of 5 average rating, 193 reviews

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

4.98 out of 5 average rating, 108 reviews

The historic log home features detailed architecture with hand-sewn logs, complemented by a vibrant red front door. A well-maintained garden with yellow flowers and greenery surrounds the entrance, while a stone pathway leads to the porch, providing easy access for guests.

Cottage in Sprucedale

*HotTub*Large* Fall Colours*FirePit* Cozy*Private*

Welcome to our enchanting family-friendly log home, a spacious and cozy retreat nestled on a secluded lot, surrounded by a lush canopy of mature trees. If you're seeking peace and tranquility, this is the perfect haven for you. Unique large, cozy log home nestled on a very private lot. Cottage is well furnished and equipped. Indoor and outdoor activities for everyone in your group to enjoy. Enjoy all four seasons at this cottage. The perfect getaway for your family and friends.

4.94 out of 5 average rating, 155 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!

4.88 out of 5 average rating, 192 reviews

Two red Adirondack chairs are positioned on a grassy area, facing a calm lake. A sandy beach and dock are visible in the background, with trees lining the shore. The scene is bathed in natural light under a clear blue sky.

Townhouse in Huntsville

Truly Amazing Muskoka Chalet - Beach & Ski hill

*Our Chalet is a licensed Airbnb* Enjoy the Muskoka lifestyle here at our spacious 3 bdrm, 2 bath, Hidden Valley chalet on beautiful Peninsula Lake. The 3 levels of living area provide everyone with their own space. Loft bedroom has its own private bath and provides a nice getaway with views of the lake and ski hills. A place perfect for couples, families and extended families. Enjoy the sandy beach & outdoor pool in the summer months and skiing and snowboarding in the winter.

4.95 out of 5 average rating, 124 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

4.88 out of 5 average rating, 275 reviews

Aerial view of a charming multi-unit building surrounded by lush greenery. The structure features a combination of yellow and white exteriors, with distinct architectural details. A paved parking area is visible in the foreground, providing ample space for vehicles.

Condo in Oro

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!

Superhost

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

4.83 out of 5 average rating, 118 reviews

Lakefront Cabin W Hottub, Sauna, Near Sir Sam Ski!

Tucked in wooded hills with private access to Redstone lake, our 5-BR, 2.5-bath cottage offers the perfect balance of comfort and nature. Just 10 mins from local shops, trails, and LCBO, and 20 mins to Haliburton. Enjoy a private saltwater pool (June–Sept), hot tub, sauna, fire pit, and high-speed Wi-Fi. Swim, paddleboard (1), or kayak (2) from the dock. We love creating a welcoming space—please, treat it as your own. Questions? Message us anytime!

4.95 out of 5 average rating, 159 reviews

A living room features a flat-screen television mounted on a stone accent wall above a small fireplace. A cozy armchair and a wooden dining table with matching chairs are visible. Natural light filters in through a window adorned with soft curtains.

Condo in Oro

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!

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

4.95 out of 5 average rating, 44 reviews

The exterior of a renovated house is framed by lush green trees and shrubs. A wooden staircase leads to the front door, enhancing the welcoming entrance. The light blue siding complements the dark green roof, while a driveway is visible alongside the property.

Home in Orillia

Cute and Cozy House

4.97 out of 5 average rating, 39 reviews

An outdoor space features multiple Muskoka chairs arranged in a semi-circle around a stone fire pit. A tranquil pond with a fountain is visible in the background, surrounded by lush greenery and trees. The evening sky is tinged with soft pastel hues.

Home in Kearney

Rondial Cottage: Lrg. Kitchen, Hot Tub, Pool &More

Superhost

An aerial view captures a stunning lakeside property featuring a spacious deck, a swimming pool, and a private dock. Surrounded by lush greenery, the retreat offers outdoor seating areas and kayaks, inviting relaxation and outdoor activities in a serene environment.

Home in Peterborough

4.9 out of 5 average rating, 42 reviews

Lakeside Retreat - Pool+GolfSim+HotTub+Sauna+Gym

4.9 out of 5 average rating, 93 reviews

A bright and spacious living area features a comfortable white sofa paired with dark blue accent chairs. A stylish dining table is set for meals, while a gas fireplace and mounted television create a cozy atmosphere. Natural light fills the room through large windows.

Home in Shanty Bay

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

4.91 out of 5 average rating, 116 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

5 out of 5 average rating, 26 reviews

Home in Gravenhurst

Luxury Resort Villa on Muskoka Bay Golf Course

4.96 out of 5 average rating, 49 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

4.76 out of 5 average rating, 68 reviews

An indoor pool is framed by large windows that allow natural light to fill the space. The ceiling features wooden beams that create an airy atmosphere. Two chairs are positioned nearby, and vibrant yellow flowers are visible through an adjacent window.

Home in Orillia

Casa ~ Pool ~ Fire Pit ~ BBQ

Condo rentals with a pool

An open living area is highlighted by a spacious sectional sofa and a round coffee table. Floor-to-ceiling windows offer views of the marina. A dining table with chairs is positioned nearby, and a stylish kitchen island with a marble countertop completes the space.

4.98 out of 5 average rating, 61 reviews

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

A modern living area features a light-colored sofa adorned with decorative pillows, positioned next to a wooden coffee table. A striped area rug lies beneath, while a kitchen island with bar stools and stainless steel appliances is visible in the background.

4.97 out of 5 average rating, 101 reviews

Cozy Stays – Your Fall Getaway at Friday Harbour

A bright and airy living area showcases a plush white sectional sofa, paired with a modern light fixture above. Large windows invite natural light, while a sleek kitchen with bar seating is visible in the background. The backyard patio is furnished for outdoor gatherings.

5 out of 5 average rating, 53 reviews

Friday Harbour Ground Floor w/ Large Terrance

The living room features a comfortable sofa adorned with decorative pillows. A Smart TV is positioned on the wall opposite a glass dining table set for four. Natural light floods the space through large glass doors, offering views of the private patio.

4.91 out of 5 average rating, 151 reviews

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

A bright living area is showcased with a red sofa and a glass coffee table positioned on a patterned rug. Large glass doors open to a balcony. A colorful wall art piece features a scenic landscape, adding a vibrant touch to the space.

4.94 out of 5 average rating, 131 reviews

Friday Harbour Luxury Condo Escape, Sleeps 4

A stylish living area features a soft gray sofa adorned with various decorative pillows in shades of blue. A light wooden coffee table, with a woven basket beneath, is positioned in front. A serene abstract mural in cool tones enhances the calming ambiance.

5 out of 5 average rating, 55 reviews

Charming 2 Bed/2 Bath at Friday Harbour Resort

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.

4.85 out of 5 average rating, 188 reviews

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

An open living area features a deep green sofa, a round coffee table, and a warm rug on light wood flooring. Natural light floods through large glass doors adorned with teal curtains, framed by plants and decorative wall art, creating a cozy and vibrant atmosphere.

4.99 out of 5 average rating, 87 reviews

Bohemian Luxury at Friday Harbour Resort Simcoe

Other holiday rentals with a pool

4.9 out of 5 average rating, 20 reviews

A circular arrangement of four dark blue Adirondack chairs features cozy white blankets draped over the arms. In the center, a fire pit sits on a stone patio, surrounded by a lush green lawn and trees displaying vibrant autumn foliage.

Villa in Gravenhurst

Luxury Modern Muskoka Retreat

Superhost

A modern living area features a spacious gray sofa with decorative pillows, an upholstered chair, and a large ottoman placed on a soft area rug. Bright natural light fills the room through expansive sliding glass doors that open to a serene outdoor view.

Villa in Gravenhurst

4.93 out of 5 average rating, 15 reviews

Nordic Elegance Villa in Muskoka

An outdoor area features a large swimming pool surrounded by lounge chairs and tables. A clubhouse is visible in the background, alongside a calm lake. Lush greenery and flowers are positioned around the space, creating a serene environment.

4.94 out of 5 average rating, 34 reviews

Luxurious Friday Harbour Condo

4.84 out of 5 average rating, 57 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

4.98 out of 5 average rating, 43 reviews

A modern living area features a gray sofa adorned with decorative pillows, accompanied by a glass coffee table and a patterned area rug. Wall shelves display decorative items and potted plants, adding a fresh touch to the muted backdrop.

Apartment in Innisfil

Trendy 1 Bdrm w/Pool & Hot Tub View

4.98 out of 5 average rating, 92 reviews

The chalet showcases a rustic wooden exterior with large windows and a sloped roof, surrounded by a snow-covered landscape. A fenced yard provides privacy, and an outdoor staircase leads to the upper level, enhancing the chalet's two-story design.

Guesthouse in Barrie

Warm rustic luxury chalet near lake & skiing

4.95 out of 5 average rating, 20 reviews

A modern living area is presented with a light-colored sofa and a cozy blue armchair. A coffee table adorned with flowers centers the space, while built-in shelves display decorative items and a television is mounted on the wall. Soft light filters through the windows, enhancing the serene atmosphere.

Apartment in Innisfil

Perfect 2 bedrm resort style unit Getaway-Top Host