Holiday rentals with a pool in Orillia

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, 444 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, 202 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!

4.97 out of 5 average rating, 149 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.

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.

4.78 out of 5 average rating, 142 reviews

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!

4.93 out of 5 average rating, 208 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

A spacious bedroom is highlighted by a large bed with crisp white linens and a decorative throw pillow. A cozy seating area features a light-colored sofa and lamps, adding to the calm ambiance. Framed artwork and a neutral color palette create an inviting atmosphere.

4.75 out of 5 average rating, 114 reviews

Lovely king size room with kitchenette

An inviting four-season natural playground surrounded by rolling hills and forested trails is located in a spectacular country setting. The Mount St. Louis Moonstone Ski Area is 12 km away, Barrie is 25 km away, and Toronto is 138 km away. Onsite amenities include a pool, fitness center, fire pit, and play area. Nearby, you can enjoy an array of fun attractions and activities for every season! Several convenient perks are available to provide you with the best and most comfortable stay.

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, 178 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!

4.85 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 Shanty Bay

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

Enjoy a stylish experience in this spacious and serene space at Highland Estates Resort. You get a completely equipped designer suite that is perfect for couples sneaking away, or families looking for the perfect vacation. Enjoy a peaceful night in your private Jacuzzi then snuggle up in a King Bed. The next day, prepare your own meal in the fully equipped kitchen with Microwave and Electric Stove. Access Netflix, Prime, Disney+. Our Pool is Open! Book Us Today

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, 100 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 spacious bed is centered in the room, adorned with a decorative throw pillow. Nightstands are positioned on either side, each featuring a lamp that casts a soft glow. Framed artwork enhances the wall above the bed, contributing to a calming atmosphere.

4.73 out of 5 average rating, 327 reviews

Cozy Deluxe Studio 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!

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, 105 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.

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.

4.96 out of 5 average rating, 178 reviews

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 Orillia 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, 55 reviews

Home in Orillia

Cute and Cozy House

4.94 out of 5 average rating, 235 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, 123 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, 29 reviews

A modern living room is presented, featuring a deep grey sofa and a round coffee table at its center. Two abstract artworks adorn the walls, while large sliding glass doors provide views of a snowy landscape outside. A cozy armchair and decorative plants add warmth to the space.

Home in Gravenhurst

Luxury Resort Villa on Muskoka Bay Golf Course

5 out of 5 average rating, 13 reviews

A modern condominium building is displayed, featuring a mix of white and dark gray exterior walls. Windows are arranged symmetrically, and small trees are placed along the walkway. A pathway leading to the entrance is visible, enhancing the building's contemporary design.

Home in Orillia

Orilluxstay

4.96 out of 5 average rating, 54 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

4.87 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

4.77 out of 5 average rating, 81 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, 111 reviews

Cozy Stays – Your Winter Getaway at Friday Harbour

4.98 out of 5 average rating, 96 reviews

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

4.96 out of 5 average rating, 27 reviews

A cozy bedroom is highlighted by a plush bed adorned with soft linens and decorative pillows. A bedside lamp casts a warm glow, while art prints with nature motifs hang above the bed. Nearby, a modern dresser and a comfortable sofa are visible, providing inviting spaces for relaxation.

Apartment in Shanty Bay

Serenity Studio Sauna+HotTub+Indoor/OutdoorPool

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, 138 reviews

Friday Harbour Luxury Condo Escape, Sleeps 4

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

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

4.98 out of 5 average rating, 104 reviews

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.

Apartment in Shanty Bay

Resort Condo (2 suites) near Horseshoe Valley

The exterior showcases a striking building with a red-and-white color scheme, surrounded by lush greenery. An indoor pool area is visible through large glass windows. An inviting fireplace is framed by stone, while a spacious dining area features a wooden table accompanied by six chairs.

4.86 out of 5 average rating, 212 reviews

Private 2BR Condo | 4 Beds+Pool+Resort

Other holiday rentals with a pool

5 out of 5 average rating, 18 reviews

A cozy bedroom is presented with a spacious bed adorned in crisp white linens and a dark throw blanket. Flanking the bed are two bedside lamps, adding soft illumination. A plant adds a touch of greenery, while a living area is visible through an open doorway.

Apartment in Oro-Medonte

NEW Ski-In Ski-Out 1-BED Condo - Pool, Gym, Sauna

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.

4.93 out of 5 average rating, 30 reviews

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

5 out of 5 average rating, 59 reviews

A single-story home is seen with a well-manicured lawn and vibrant flower beds. A Canada flag is displayed on the front porch. A driveway accommodates one vehicle, while decorative stones border the driveway, adding a neat touch to the entrance.

Bungalow in Keswick

Dave & Jenny’s Apartment.

5 out of 5 average rating, 13 reviews

A warm and inviting dining area features a large wooden table at the center, surrounded by three stools. A well-lit window provides natural light, with greenery visible outside. The space includes a flat-screen television and a cozy seating area, enhancing the overall comfort.

Flat in Georgina

Quiet Country Escape Close To Beach Parks And Golf

4.92 out of 5 average rating, 60 reviews

Nature trail views with cozy patio and firetable!

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, 77 reviews

Cozy Residence with Walkout to Courtyard

4.91 out of 5 average rating, 32 reviews

A modern kitchen is displayed, featuring sleek white cabinets and dark granite countertops. Illuminated by pendant lights, the space includes a double sink and an island with seating. Stainless steel appliances and a mosaic backsplash add to the contemporary design while maintaining an organized feel.

Flat in Barrie

Clean, bright and cozy walkout basement