Holiday rentals with a pool in Gravenhurst

Dome in Bradford West Gwillimbury

Vibrant autumn foliage displays shades of yellow and orange surrounding a geodesic dome. A pathway of stone steps leads through a lawn covered in colorful leaves, creating a serene outdoor setting amidst lush greenery.

4.96 out of 5 average rating, 412 reviews

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...

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!

4.83 out of 5 average rating, 113 reviews

A spacious living area features a comfortable tan sofa and modern black dining chairs surrounding a circular table. A gas fireplace and television are positioned against a light stone wall, while large windows allow natural light to fill the room. Decorative elements include a floor plant and a wine display.

Townhouse in Shanty Bay

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.

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.

4.8 out of 5 average rating, 119 reviews

An outdoor pool area is featured, surrounded by lounge chairs and picnic tables. A large building with expansive glass windows serves as a backdrop, while bright blue umbrellas provide shade. The surrounding greenery enhances the tranquil ambiance of the resort.

Condo in Oro

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!

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

4.94 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!

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.

4.87 out of 5 average rating, 168 reviews

Friday Harbor Upscale 1Bed+Sofabed+Pool Option

Experience the allure of Friday Harbour! Stay in this gorgeously furnished 1-bedroom condo, complete with a pullout sofa bed. Enjoy the stunning outdoor relaxation area that overlooks the courtyard pool. The condo features a spacious bedroom with a closet and a large bathroom. Its layout is perfect for both relaxation and entertainment, with an open concept living area and a kitchen featuring an island. Embrace the ultimate indoor and outdoor living experience at Friday Harbour!

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!

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 Gravenhurst 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

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, 105 reviews

The Cozy Corner Townhome - Shuttle to the Village

4.88 out of 5 average rating, 250 reviews

Large 4 Br - 4.5 Bathroom: 2 King beds/Sauna/games

An open-concept living area is displayed, featuring a gas fireplace with a mounted television above it. A spacious wooden coffee table is centered on a light-colored rug. The dining area, with a dark table and chairs, is visible in the background, complemented by a well-equipped kitchen.

4.9 out of 5 average rating, 101 reviews

Rivergrass Oasis: Steps to Blue Mountain Village!

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.

4.87 out of 5 average rating, 127 reviews

Blue Mountain Retreat In Historic Snowbridge

4.94 out of 5 average rating, 232 reviews

A private hot tub is positioned on a wooden deck beneath a lattice covering, allowing for relaxed soaking. Lounge chairs are arranged nearby, and vibrant greenery and decorative flowers provide a natural backdrop. A swimming pool can be seen in the distance, enhancing the outdoor ambiance.

Home in Port Perry

Home away from home with a hot tub and pool

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

A master bedroom features a spacious bed adorned with a blue and white comforter. Light wooden flooring is complemented by a decorative nightstand and a stylish chandelier. Large windows allow natural light to fill the room, offering views of the greenery outside.

4.93 out of 5 average rating, 215 reviews

Serene mountainside home with View/Shuttle Bus

Condo rentals with a pool

4.82 out of 5 average rating, 219 reviews

Still Winds - Private Patio / Shuttle to Blue

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.

4.89 out of 5 average rating, 270 reviews

Hidden Haven - Shuttle to Blue / Private Patio

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, 110 reviews

3 Peaks at Blue Mountains, your luxury staycation!

4.92 out of 5 average rating, 132 reviews

Highlands Lodge & Loft - Shuttle to the Village

The open-concept living area features two comfortable sofas with decorative cushions. A dining table is set for six nearby, while kitchen access is visible in the background. Natural light enters from large windows, with wooden accents enhancing the space.

4.87 out of 5 average rating, 146 reviews

Out of the Blue - Shuttle to Blue, Walk & Trails!

The living room is designed with a cozy sectional sofa and a coffee table placed centrally. A mounted flat-screen TV is positioned above a white-brick fireplace. Natural light filters through sheer curtains, enhancing the welcoming feel of the space.

4.94 out of 5 average rating, 332 reviews

Cozy & Charming Retreat at Blue Mountain

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

Other holiday 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

4.95 out of 5 average rating, 22 reviews

A private rooftop patio features comfortable seating and views overlooking Lake Simcoe. An outdoor pool with lounge chairs invites relaxation, while an interior view showcases a modern chef’s kitchen with sleek appliances and bar seating. Natural light fills the open living space through large windows.

Townhouse in Orillia

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

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.

4.9 out of 5 average rating, 20 reviews

Luxury Modern Muskoka Retreat

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.

4.93 out of 5 average rating, 15 reviews

Nordic Elegance Villa in Muskoka

An outdoor seating area is displayed with a glass-top coffee table surrounded by two chairs and a spacious sectional sofa. Lush greenery and trees are visible in the background, creating a serene view of the natural landscape.

4.83 out of 5 average rating, 6 reviews

Villa On The Green

The living area features a light-colored sofa paired with a stylish armchair, placed on a neutral-toned area rug. Large glass doors provide access to the private patio, allowing natural light to fill the space. An elegant coffee table is centered in the area, complemented by modern decor.

4.96 out of 5 average rating, 71 reviews

Walkout to Courtyard w/ Pool, Hot Tub and Fire Pit

An aerial view captures the resort’s clubhouse surrounded by vibrant autumn foliage and rolling landscapes. Two outdoor pools are visible, complemented by sun loungers and a rocky terrain. The expansive greenery suggests recreational opportunities nearby, inviting exploration of the diverse natural surroundings.

4.88 out of 5 average rating, 25 reviews

ScandinaVilla Retreat

An outdoor dining area features a large table surrounded by six chairs, with additional seating provided by two tall chairs nearby. A modern barbecue grill is positioned to the side. The backdrop includes a spacious patio and large windows leading into the villa.