Holiday rentals in Winsloe South

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Top-rated holiday rentals in Winsloe South

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Top guest favourite
A modern two-story home features a spacious balcony with glass railing and outdoor seating. Lush green grass surrounds the property, while trees provide natural landscaping. The structure showcases an angled roof, integrating natural materials for a seamless connection with the environment.
Guest house in Downtown Charlottetown
4.89 out of 5 average rating, 207 reviews

Wharfside - Waterfront + Downtown + Victoria Park

Unwind in this newly built main level suite overlooking the Charlottetown Harbour and the picturesque Victoria Park and just a short stroll to downtown shops & restaurants. Modern architecture at its finest, this loft has spared no expense. Floor to ceiling windows look out to sailboats and sunsets. Appointed with the luxury traveller in mind, this home is equipped with high end appliances, marble countertops, luxury linens and a king size bed for a truly restful sleep and stay. License #4000033

Guest favourite
A large waterfront home is positioned on lush green grass, with scenic views of the water. The building features a neutral exterior and a sloped roof, framed by a clear sky. A driveway leads toward the house, enhancing accessibility.
Home in Marshfield
4.95 out of 5 average rating, 60 reviews

Beau View River House

Welcome to our beautiful waterfront property located just 10 minutes from downtown Charlottetown and 15 minutes to PEI's world renowned North Shore beaches! With 4 bedrooms and 3 baths, our large and private countryside rental has everything you need for a relaxing vacation with family and friends. Enjoy the spacious outdoors playing lawn games, having a campfire or relaxing on the deck. Spend your time indoors in our cozy, open concept living area or playing pool or ping pong in the game room.

Superhost
Guest suite in Brackley Beach
5 out of 5 average rating, 3 reviews

Brackley Beach Bunker

This one bedroom, basement apartment, is a very comfortable hideaway in Brackley Beach. If you’re looking for a cozy, movie themed underground retreat, and be in a central area on PEI, this is the spot. The owner loves movies, and the shelves have a great movie collection. There is also a great collection of books. A heated bathroom floor, cozy carpeted bedroom, and a kitchen with all the necessities. *It is a basement apartment, so you will hear footsteps above you from the other guests.*

Guest favourite
A modern kitchen is presented with stainless steel appliances, including a refrigerator and stove. Sleek gray cabinets provide storage, while a small island features two red bar stools. A window above the sink allows natural light to illuminate the space, complemented by a red accent rug.
Guest suite in Charlottetown
4.83 out of 5 average rating, 82 reviews

Maple Leaf home/Olde Brighton/10 mins to downtown

The suite is in the walk out lower level of our home in what is know as Olde Brighton. You are a pleasant 12 minute walk to Downtown Charlottetown, the waterfront “Boardwalk” and Victoria Park with its expansive view along the Ocean. Victoria Park is home to the Lieutenant Governor's residence, open daily to the public with free admission. It is a wonderful area to host a picnic, take in a swim in the large, free, outdoor pool or enjoy the large well-designed children’s playground.

Top guest favourite
A hot tub is shown with bubbling water, illuminated by soft pink lights. Two elegant glasses are placed on the ledge, set against a backdrop of a sunset sky featuring shades of purple and orange over the water.
Home in Mermaid
4.98 out of 5 average rating, 83 reviews

The Mermaid Shore House is a gem on the water.

The Mermaid Shore House is a brand new wheelchair accessible build overlooking the Hillsborough River, a small beach and city lights of Charlottetown. This well equipped two bedroom house is bright and spacious with numerous windows that take advantage of the stunning water views and sunsets. Imagine, after an evening BBQ sipping chilled wine in your hot tub while enjoying the harbour lights. Launching from the shore is easy and convenient. Bring your kayaks, seadoos or paddle boards.

Top guest favourite
A neighborhood scene features a vibrant rainbow arching over several houses, creating a colorful contrast against a cloudy sky. Power lines traverse the image, with wet pavement reflecting the greenery surrounding the homes.
Flat in Charlottetown
4.87 out of 5 average rating, 256 reviews

Charlottetown brand-new suite

This brand-new basement suite is modern and stylish. Our location is ideal for tourists. 5 minutes from airport. 15 minutes drive to downtown Charlottetown where guests can explore historic sites. 15 minutes drive to Brackley Beach, one of the largest and popular beach in PEI. This newly built basement suite is fully furnished with modern amenities, offering guests a comfortable and convenient stay. We take pride in providing guests with a clean and welcoming environment.

Guest favourite
A ranch-style house is depicted against a backdrop of trees, showcasing an expansive front lawn. The exterior features a smooth surface with a prominent arch window at the center, flanked by symmetric landscaping and entrance doors. Cloudy skies create a serene atmosphere.
Home in Milton Station
5 out of 5 average rating, 8 reviews

Cozy/Private Home away from Home

Glengyle Lane is a serene one level ranch style centrally located in Milton, PEI. This very peaceful spacious property is close to many seasonal attractions such as Brackley Beach, Cavendish Beach, many golf courses, UPEI (MacLauchlan Arena), airport and other popular places within a short drive. Open concept with comfy seating, fully stocked kitchen, large back deck/yard space including a fire pit and a lovely front veranda to relax with a book and enjoy PEI sunsets.

Guest favourite
Home in Kensington
5 out of 5 average rating, 7 reviews

Sunset Shadow

Modern yet cozy newly built home centrally located in the heart of PEI. Sunset Shadow offers three bedrooms and two bathrooms, providing comfortable accommodations for families, couples, or small groups. Just 12 km from Summerside, 25 km from Cavendish Beach, and 50 km from Charlottetown, you’ll be close to PEI’s most popular attractions. Perfect for beach trips, golf getaways, or peaceful escapes, with a serene setting beside our sister property, Sunset Hideaway.

Top guest favourite
A unique two-story structure built from shipping containers is bathed in warm sunlight. An expansive deck is visible on the upper level, while multiple windows create a light-filled entryway below. The surrounding green landscape adds to the inviting setting.
Cottage in Grand Tracadie
5 out of 5 average rating, 70 reviews

Steel Away 2 Heightened. Coastal. Comfort.

Listen to the breakers from the North Shore, Watch Osprey and Bald Eagles fish in the Bay. Spectacular panoramic Sunrises, Stars and Sunsets from an elevated deck with hammocks. Soak in the hot tub after a day of golf, at the beach or on the water in one of our kayaks or SUP. At the end of Queens Point on Tracadie Bay, watch the boats harvest blue mussels, walk around the Point, or sit and read a book. It's a special kind of peaceful here, happy to share.

Guest favourite
A modern cottage is depicted with large windows and a patio area. Red outdoor chairs are arranged around a circular table on a concrete patio, surrounded by neatly maintained grass and small trees. Additional cottages are visible in the background.
Cabin in Charlottetown
4.72 out of 5 average rating, 127 reviews

Brand New - Modern Cozy 1 Bedroom Cottage

Escape to comfort at Royalty Maples Motel & Cottages in Charlottetown. Our modern 1-bedroom cottages feature a private bedroom with Queen bed, full kitchen, bathroom, living area with sofa bed, Wi-Fi, smart TV, air conditioning, and free parking. Enjoy a quiet setting just minutes from downtown, beaches, golf, restaurants, shopping, and PEI attractions. Dog-friendly units available (max 1 pet). BBQ rentals available seasonally.

Top guest favourite
A living room features two brown sofas, one adorned with decorative pillows. A wooden coffee table occupies the center, complemented by a potted plant. Natural light enters through a large window, highlighting a welcoming atmosphere. A framed artwork of a barn is displayed on the wall.
Bungalow in Oyster Bed Bridge
4.95 out of 5 average rating, 386 reviews

The Bluejay Cottage | Close to Brackley beach!

The Bluejay cottage is set back from the road with 3 other cottages. Fully equipped with all the extras! Our cottages are conveniently located in the populair north shore area. 20 min away from Charlottetown and Cavendish, and only 5 min away from Brackley Beach. Each tip of the island is easily reached within an 1.5 hours. This is the perfect place to gather your family for a get-a-way and to explore the island!

Top guest favourite
A view from the upper level showcases warm pine walls and cathedral ceilings with skylights. The open area below features large windows, allowing natural light to fill the space. A wooden railing provides a clear separation from the living area, enhancing the cozy atmosphere.
Cottage in York
4.97 out of 5 average rating, 164 reviews

WALK to beach - charming cottage in Stanhope

Situated on a quiet private lot -a 10 min walk to the beach, our spacious, air conditioned 3 BR cottage with cathedral ceilings is a place to relax & unwind. All comforts of home with nature as well Stanhope offers: - sandy beach - golfing - fishing wharf - walking & biking trails We are 25 min drive to Charlottetown Tourism PEI - License # 2200387 & also a member of Canada Select

Popular amenities for Winsloe South holiday rentals