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Holiday rentals with a pool in The Archipelago

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in The Archipelago

Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

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Guest favourite
Home in Midland
4.82 out of 5 average rating, 49 reviews

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

Stylish. Privacy. Location. Our Vacation Home, is in vibrant Downtown Midland. We’ve recently renovated our amazing century home and it is ready for you to enjoy! – its beauty matches the beauty of the town. Our spacious home features a great backyard for you to relax in. When venturing out to explore the area we know you’ll enjoy Midland Harbour. This picturesque natural attraction has been a favourite of tourists and boaters from around the world. Our home is just a few minutes’ walk away!

Superhost
The swimming pool is framed by concrete surfaces and features a sleek diving board at its edge. Lounge seating is positioned nearby, with vibrant greenery lining the space and providing a sense of privacy. A well-maintained property is visible in the background, surrounded by trees.
Cottage in Penetanguishene
4.75 out of 5 average rating, 65 reviews

Discovery Retreat: Hot Tub, Firepit, Game Room

Welcome to The Discovery Retreat. Nestled amidst 100-year-old trees in the historic town of Penetanguishene, our cozy wooden cottage offers serenity and charm. Wake up to breathtaking views of the forest from your bedroom window. Relax in our large hot tub and a heated 600sqft pool, overlooking the tranquil discovery bay and vibrant sunset hues. Watch the night sky huddled up by the fire pit. Choose from our extensive collection of indoor games for a cozy night in. Your perfect retreat awaits!

Top guest favourite
Townhouse in Port Severn
4.99 out of 5 average rating, 212 reviews

Wifi, Free parking, Ski, Kitchen, Laundry, TV, BBQ

Welcome We share with you our ⭐️⭐️⭐️⭐️⭐️ ‘super clean’ and pet friendly home -Free parking, -EV Charger, -Fast Wifi, -Indoor Fireplace (downstairs in the winter months only) -two outdoor fire pits (Solo Stove) -Full Kitchen, -Air Conditioning, -Peloton, -Hot Tub -Loft -Smart TV, -Washer and Dryer Oak Bay Golf Course, large yard, seasonal shared pool. Children's supplies -Crib, -toys, -playmat and custom dog 🐾house Minutes from Georgian Bay Island National Park in Muskoka.

Guest favourite
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
4.96 out of 5 average rating, 137 reviews

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.

Superhost
An inviting living space features a comfortable gray sofa adorned with decorative pillows. A rustic wooden coffee table sits at the center on a layered area rug, complemented by the natural light filtering through the windows. Plants add a touch of greenery to the room.
Cottage in Penetanguishene
4.92 out of 5 average rating, 39 reviews

Georgian Bay Escape

Located right next to Georgian Bay, our well-equipped home is the perfect get away with lots of activities in the quaint town of Penetanguishene. Explore the area with a snowmobile tour or ski at near by slopes. Lots of beautiful beach's near by for your summer stays. The home is also equipped for remote work. Only minutes from the waterfront, Champlain Wendat Park with a splash pad, outdoor gym, skateboard, museum , floating fishing dock, beach volleyball, restaurants along the way!

Superhost
A wooden deck leads to the entrance of the house, featuring a covered seating area with hanging chairs. Lush greenery surrounds the property, providing a natural backdrop. The stairs are designed for easy access, ensuring a welcoming entrance for all guests.
Cottage in Huntsville
4.73 out of 5 average rating, 117 reviews

Muskoka cottage with Pool

Enjoy at this stylish, spacious, & family-friendly place with your friends and family ➤5 Bedrooms house with 3 queens, 1 king, & 1 bunk bed ➤2 Living rooms with sitting arrangements & a sofa bed ➤3 Full bathrooms ➤Pool (available during summer only) ➤Fully equipped kitchen ➤Toy room in the basement for Kids ➤85" HD TV with Netflix ➤Patio, BBQ, & fire pit ➤Fresh linens, towels, toiletries, & essentials provided ➤Professionally cleaned every time ➤On-driveway parking for up to 4 vehicles

Guest favourite
Cottage in Burk's Falls
4.94 out of 5 average rating, 18 reviews

The North Retreat

The ultimate escape at this tranquil 4-season, 3-acre getaway on 3 Mile Lake, 25 minutes north of Huntsville. Loads of water activities, a massive private sandy beach for relaxation & play, captivating creek & forest to explore, & the option to unwind in the hot tub or swim spa, offers endless possibilities. This private getaway provides the perfect setting for a memorable experience all year round. Close to Hidden Valley Ski Hilll, Algonquin ice skating and OFSC snowmobile trails.

Top guest favourite
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
4.98 out of 5 average rating, 108 reviews

*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.

Superhost
A living area features two comfortable sofas arranged around a wooden coffee table, which holds decorative items. A dining table with white chairs is positioned nearby, and the wall displays a subtle blue texture, adding visual interest to the space.
Home in Carling
5 out of 5 average rating, 4 reviews

The Franklin at Dillon Cove

- 3-bedroom rental overlooking the bay– perfect for families or small groups - Sleeps up to 6+ guests with 1 queen bed, 1 double bed, bunk bed, and a futon - Step outside to your private deck with comfortable patio furniture for relaxing outdoors - Equipped with a coffee maker and microwave for convenient meals - Dishes and utensils included for all your cooking needs - Fire TV available for your entertainment - 4-piece bathroom (tub, shower, toilet, sink) - Propane BBQ

Guest favourite
The cottage features a welcoming porch with large windows, providing a view of the surrounding trees and nature. The entrance is flanked by picnic tables, inviting outdoor gatherings. Soft evening light enhances the cozy atmosphere of the renovated exterior.
Bungalow in Lafontaine Beach
4.91 out of 5 average rating, 74 reviews

Sweet Memories of Georgian Bay

Beautiful renovated cottage at the family oriented Georgian Bay Beach Club! Amazing views of Georgian Bay. Private beach, stunning pool and lounge area. Private courtyard for dining/lounge beside cottage. Enclosed porch with view of Georgian Bay. Very quiet and tranquil, nature walks outside your door. Surrounded by beautiful mature trees...the perfect place just to read a book and watch the waves. Parking for 2 cars with easy access to main entrance door.

Top guest favourite
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
4.96 out of 5 average rating, 50 reviews

Comfort, Luxury and Relaxation

Welcome to beautiful Muskoka! Escape the city and relax in this calm, quiet and luxury 4 season villa. Located at Muskoka Bay resort in Gravenhurst, this villa is located steps away from one of the Top Golf Courses in Canada. Enjoy luxury amenities including wood barrel saunas, big wheel bikes, outdoor infinity pool, outdoor children's pool (Pool seasonal) and the Cliff-Top club house boasting one of the best culinary experiences in Muskoka

Guest favourite
A clear blue sky hovers over a tranquil pool, with vibrant green hydrangeas framing the view. The pool's edge is lined with stone paving, offering direct sightlines to the expansive waters of Georgian Bay, enhancing the peaceful outdoor retreat.
Guest suite in Midland
4.95 out of 5 average rating, 43 reviews

The Magic by Georgian Bay

Settled in a quiet neighbourhood within walking distance to restaurants, shops, art and cultural events in central Midland. Enjoy waterfront views, next to a beautiful pool with direct access to the Georgian Bay trail, that is meandering along the shore of Georgian Bay. Cyclists paradise cruising the shores of Georgian Bay as part of the Trans Canada trail for miles. From Penetanguishene to Victoria Harbor and Coldwater.

Popular amenities for The Archipelago rentals with a pool

Quick stats about holiday rentals with a pool in The Archipelago

  • Total holiday rentals

    Explore 20 holiday rentals in The Archipelago

  • Nightly prices starting at

    The Archipelago holiday rentals start at $105 SGD per night before taxes and fees

  • Verified guest reviews

    Over 270 verified reviews to help you choose

  • Family-friendly holiday rentals

    20 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 10 rentals that welcome pets

  • Wifi availability

    20 of The Archipelago holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across The Archipelago rentals

  • 4.9 Average rating

    The Archipelago stays are highly rated by guests – averaging 4.9 out of 5!