Holiday rentals with a pool in Barrie

4.91 out of 5 average rating, 126 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

Our luxury home rental is located in one of the best neighborhoods in Barrie. Secluded neighborhood surrounded by forest. 5 min to HWY 400 8 min to Downtown Barrie 11 min to Snow Valley Ski resort 40 min to Blue Mountain & Wasaga Beach 25 min to Friday Harbor Resort Free WiFi-Cable & Parking Perfect home for families and large groups. Newly renovated home, with beautiful large outside area and swimming pool. Accommodates up to 9 guests. Pool open May 31 (Solar heated) Pool closes Sept.7

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, 456 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...

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.

5 out of 5 average rating, 205 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!

4.91 out of 5 average rating, 256 reviews

Cottage in Alcona

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.

The living area features a modern design with a large flat-screen TV mounted above a stone fireplace. A cozy gray sofa is paired with a rustic coffee table and a comfortable orange armchair. Natural light enters through double glass doors leading outside.

4.98 out of 5 average rating, 108 reviews

Resort Condo (2 suites) near Horseshoe Valley

Enjoy a stylish experience in this spacious and serene space at Carriage Country Club Resort. A completely equipped designer condo with 2 suites for families looking for perfect vacation. Enjoy a peaceful night in your private Jacuzzi , prepare your own meal in the fully equipped kitchen. Few minutes drive to Horseshoe Valley Resort, and walkable to Vettä Nordic Spa. For Mount St. Louis Moonstone, only about 15 minutes drive away. Our heated indoor/outdoor swiming pool, available year-round.

4.96 out of 5 average rating, 151 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.

A modern living area features a spacious sectional sofa complemented by decorative pillows and a large coffee table. Natural light floods in through expansive glass windows, revealing a view of the private patio. Minimalist decor includes a geometric wall design and a stylish light fixture.

4.94 out of 5 average rating, 131 reviews

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!

4.93 out of 5 average rating, 209 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

An open living space is displayed, featuring a comfortable sofa adorned with throw pillows. A central coffee table rests atop a patterned area rug, while a wooden dining table with seating for six is visible. The kitchen area is positioned at the back, showcasing modern appliances.

4.88 out of 5 average rating, 102 reviews

Stunning Suite in Horseshoe Valley

Sitting on top of Horseshoe Valley, this stunning and unique condo sets the stage for a memorable and cozy trip. This suite has it all! - Fully stocked kitchen - 6-person dining table - Pull-out couch + loveseat + lounge chair - Cozy fireplace - Comfortable king-size bed - 2-person soaker tub + shower - Private Balcony - Year-round indoor/outdoor pool with hot tub and sauna - Fully equipped gym Minutes away from Vetta Spa, Horseshoe Valley, golf courses and more!

A cozy living area features a spacious sectional sofa adorned with soft pillows, complemented by a minimalist coffee table. Natural elements are highlighted by an accent wall showcasing a scenic forest mural. The nearby sleeping area includes a neatly made bed with fresh linens.

4.99 out of 5 average rating, 102 reviews

Wildwood HotTub+Indoor/Outdoor Pool+Sauna+GameRoom

Welcome to our cozy, modern condo in Horseshoe Valley — the perfect destination for families and groups of friends seeking adventure, relaxation, and unforgettable memories. Just a 2-hour drive from Toronto, our condo offers a prime location to experience it all. Whether you're hitting the slopes, unwinding at the Nordic spa, or exploring the outdoors with mountain biking, golf and tree-top trekking, you'll find everything you need for a perfect getaway.

A modern living area features a gray sectional sofa adorned with yellow cushions. A light wood coffee table is positioned in front. The kitchen bar area with high stools is visible, complemented by sleek cabinetry. Large glass doors provide access to the outdoor patio.

4.87 out of 5 average rating, 122 reviews

Aquarius bldg @ Friday Harbour 1st fl 2 bdr/2 bath

Main floor 2 bdr 2 bath condo in Aquarius building 825 sq. ft of indoor space. With a seasonal pool available . Enjoy a luxurious stay at an all season resort at Friday Harbour. We are Steps away from marina, beach, boardwalk, trails and more. Plenty of outdoor activities to enjoy all year round. Our fully furnished condo is ready for you and your guests to enjoy. Outdoor patio to catch fresh air & a cozy, stylish indoor space to unwind and enjoy.

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, 109 reviews

Bohemian Luxury at Friday Harbour Resort Simcoe

Welcome to a Bohemian Paradise in the Heart of Friday Harbour. Treat yourself to a relaxing experience only 1hr from Toronto. This beautifully designed condo was designed to make your experience at Friday Harbour the best it can be. **Convenience** One of the few condos with direct walkout to the courtyard’s Firepit and BBQs. Steps away from Restaurants, Nature Trails, Beach & Boardwalk, Golfing, Live Music Events every Weekend.

Popular amenities for Barrie rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.95 out of 5 average rating, 56 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

4.98 out of 5 average rating, 40 reviews

A serene backyard view showcases a well-maintained lawn bordered by diverse greenery and a calm river. Several seating areas, including white chairs and a shaded gazebo, provide relaxation spots. A swimming pool is visible, reflecting the clear blue sky above, creating a peaceful outdoor setting.

Home in Holland Landing

Private river access with pool, canoes, kayak

4.88 out of 5 average rating, 99 reviews

A modern living area is highlighted by a sleek, electric fireplace beneath a large flat-screen TV. A rustic accent wall features wooden panels and decorative art. A comfortable gray sofa and a table set for dining complete the welcoming space, complemented by blue and natural tones.

Home in Innisfil

2 Bd Boardwalk Condo Patio Oasis

4.85 out of 5 average rating, 110 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 Horseshoe Valley

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

4.8 out of 5 average rating, 51 reviews

A private swimming pool is surrounded by well-maintained gardens, featuring vibrant green shrubs and flowers. A spacious patio area with outdoor furniture is also visible. The clear blue sky enhances the serene ambiance of this inviting outdoor space.

Home in Midland

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

4.81 out of 5 average rating, 16 reviews

Home in Barrie

Themed Escape - Pool | Bunkie | Sleeps 12

4.87 out of 5 average rating, 99 reviews

A hot tub is situated under a wooden gazebo, featuring railings and a ceiling adorned with decorative elements. Sunlight illuminates the scene, highlighting the inviting water surface. A view of the snowy landscape and frozen lake extends in the background, enhancing the serene atmosphere.

Home in Elmvale

Ski, Swim, Soak, Boat & Golf

4.76 out of 5 average rating, 84 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

Apartment rentals with a pool

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, 112 reviews

Golf, Spa & Spring Vibes Getaway at Friday Harbour

An aerial view captures the expansive Friday Harbour Resort, showcasing the marina and surrounding greenery. The second image features a bright dining area, furnished with a circular table and chairs, adjacent to a comfortable living space with a sofa and large windows. An inviting outdoor pool area is depicted, surrounded by elegant lounge seating and woody accents, providing a relaxing atmosphere.

4.91 out of 5 average rating, 32 reviews

FH Penthouse | Luxury 4-Bed | Pool & Hot Tub | BBQ

4.98 out of 5 average rating, 99 reviews

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

The living area features a comfortable sofa beside a stone fireplace, providing a cozy focal point. A light-toned armchair sits nearby, while a television is mounted on the wall. Natural light enters through the glass door, leading to an outdoor space.

4.81 out of 5 average rating, 155 reviews

Cozy 1-Bedroom Romantic Retreat with full Kitchen

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.

4.9 out of 5 average rating, 42 reviews

Luxurious Friday Harbour Winter Wellness Escape

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, 78 reviews

Cozy Residence with Walkout to Courtyard

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, 179 reviews

Friday Harbor Upscale 1Bed+Sofabed+Pool Option

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, 140 reviews

Friday Harbour Luxury Condo Escape, Sleeps 4

Other holiday rentals with a pool

5 out of 5 average rating, 26 reviews

Flat in King City

The King's Rest

4.92 out of 5 average rating, 60 reviews

Nature trail views with cozy patio and firetable!

A modern kitchen features sleek appliances, ample counter space, and cabinetry, creating an inviting cooking area. An expansive outdoor pool area is surrounded by lounge chairs, providing a relaxed atmosphere. The marina glows with lights, showcasing boats and waterfront amenities, encapsulating serene evenings by the water.

4.94 out of 5 average rating, 16 reviews

1BR Friday Harbour Retreat | Balcony + Pool Access

4.93 out of 5 average rating, 41 reviews

A heated pool is set within a spacious patio area, featuring inviting blue waters and a bright green inflatable float. Two chairs are positioned alongside the pool, with a tall red umbrella providing shade. Lush greenery and a secure fence surround the area.

Guest house in Uxbridge

Redwood Haven East: Your Dream Getaway in Uxbridge

An outdoor seating area is furnished with a large sectional sofa and a table, providing a comfortable space for relaxation. The balcony overlooks a pool surrounded by greenery and modern buildings, offering a serene view of the outdoor amenities.

4.98 out of 5 average rating, 41 reviews

Modern Luxury Delight with a Pool and Hot Tub

Villa in Whitchurch-Stouffville

A serene pool area is illuminated by soft lighting, highlighting the clear water and inviting atmosphere. Surrounding the pool, comfortable lounge chairs and seating areas are arranged for relaxation. The natural surroundings create a peaceful backdrop, enhanced by the warm glow of lights.

4.97 out of 5 average rating, 35 reviews

Cedar Escape • Sauna • 10-Acre Private Forest

A contemporary living space features a spacious sofa with cozy blue pillows set against large windows. A round coffee table rests on a patterned rug, and stylish dining chairs surround a kitchen island in the open-concept design.

4.95 out of 5 average rating, 56 reviews

NEW Luxurious Corner Unit at Friday Harbour Resort

A modern kitchen is featured with light wood cabinetry and a spacious island. Bar stools are positioned at the island, and appliances include a stainless steel stove and refrigerator. A large window allows natural light to illuminate the space, revealing serene outdoor views.