Holiday rentals in Oak Bluff

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Top-rated holiday rentals in Oak Bluff

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite

A two-story house is set against a cloudy sky, surrounded by well-maintained green grass and trees. A pathway leads to the entrance, with a gravel trail visible to the side. The structure features a mix of light and dark siding, providing a contemporary look.

Guest suite in Headingley

Private Luxury 2 bedrooms Basement Suite Winnipeg

New Fully Furnished Basement suite This suites offer 📌 2 bedrooms (1 King Size and 1 Queen Size) 📌 1 Full washroom 📌 spacious Living Area 📌 Large Kitchen 📌 Dining area 📌 Led Tv 4K UHD 65 Inches with Netflix 📌 Separate Entrance 📌 Lit path 📌 Free 24 Hrs Parking 📌 Free WiFi Welcome to our New Suite nestled in Very peaceful neighbourhood in Blumberg Trail Just Stones throw away from Trans Canada Hyw 1. Whether you're here for a relaxing getaway our location ensures Privacy nd convenience.

4.98 out of 5 average rating, 247 reviews

Superhost

A spacious two-story house is presented, featuring a large front garage and multiple windows that allow natural light to fill the interior. Snow accumulates along the driveway, indicating the winter season. The exterior is a combination of light-colored stucco and a dark brown garage door.

Home in Winnipeg

Marvellous House / 2 min to University of Manitoba

Welcome to your home away from home! This beautifully designed 6-bedroom house is perfect for large families, travel groups, visiting academics, or sports teams; and for small group that desire privacy and affordability; it offers comfort, space, and convenience in one of the city’s most sought-after quiet neighborhoods. Features: 12 guests; Fully Equip. Kitchen; Dedicated Dinning; Living room and bedrooms with Smart TVs; Fenced Yard; Parking for 4 cars; Free Laundry; 3.5 Baths; Deck & Barbeque.

4.79 out of 5 average rating, 105 reviews

Top guest favourite

Barn in Saint Germain South

River Creek Retreat

Experience the quiet of our 900-sq ft timber frame straw-bale suite. Relax in the 3-person eco-friendly hot tub. The private, main floor suite is surrounded by gardens and trees. Situated on an acreage 11 kms south of Winnipeg, only a 30 minute drive from downtown (10 min longer now, due to road closure). A close-to-the-city location that feels remote and relaxing. In winter, experience the luxury of radiant floor heating. In summer, marvel at how the space remains cool without air conditioning.

4.99 out of 5 average rating, 90 reviews

Guest favourite

Home in Winnipeg

1-bedroom Walkout basement with private entrance

Bright walkout 1-bedroom basement suite with private entrance in a quiet, family-friendly neighborhood. Part of a well-maintained single-family home, this cozy space has large windows, plenty of natural light, and a modern layout. ✔ Private entrance ✔ Bright walkout basement suite ✔ Quiet residential neighborhood ✔ Ideal for short & long-term stays ✔ Close to walking trails & green spaces To ensure a peaceful environment for everyone, quiet hours are observed between 10:00 PM and 7:00 AM.

4.85 out of 5 average rating, 59 reviews

Top guest favourite

A spacious dining area is presented with a round wooden table surrounded by cross-back chairs. A yellow bowl sits at the center of the table. Light wood flooring complements the neutral walls, while a charming patterned chair adds a touch of color to the space.

Home in Winnipeg

Aubrey Fox Den #STRA-2026-2479756

This cozy character home is nestled in the heart of Wolseley, one of Winnipeg's most beloved, safe, urban neighbourhoods. The Aubrey Fox Den is only a short walk from an Italian specialty food store, organic grocery store, wool shop, bookstore, juice bar, and wonderful local breweries, artisanal coffee shops bakeries and bistros. With easy travel downtown and minutes away from the Assiniboine River with gorgeous kayaking in the summer and walks, skiing, skating and campfires in the winter.

4.96 out of 5 average rating, 178 reviews

Top guest favourite

A wooden pathway illuminated by string lights leads to the treehouse, reflecting warmly on the water. The structure's large window offers a glimpse of the interior, while trees line the background, creating a serene atmosphere at dusk.

Treehouse in Rosenort

Treehouse on the River

Reconnect with nature at this unforgettable escape just 30 minutes from Winnipeg. This cozy treehouse is a perfect getaway for rest, creativity and renewal. The single bedroom is surrounded by a wraparound deck with peaceful river views, offering a true sense of immersion in the outdoors. Finish your day and canoe along the river while watching wildlife or relax with a bon fire underneath a canopy of stars. Clear your mind in this serene setting. (bathroom on property 100 meters away)

4.93 out of 5 average rating, 306 reviews

Guest favourite

A spacious bedroom is highlighted by a large bed with a dark headboard and soft bedding. Natural light filters through a window, framed by dark curtains. A small desk and lamp are positioned nearby, while recessed lighting enhances the overall ambiance.

Home in Winnipeg

Entire Suite in Crestview

Welcome to our amazing new suite nestled in a peaceful neighborhood in Crestview, just a stone's throw away from Winnipeg's finest dining establishments and shopping centers. Whether you're here for a relaxing getaway or a business trip, our location ensures convenience and tranquility. Situated a mere 15-minute drive from Winnipeg Airport and Polo Park, our suite is easily accessible. As part of a new duplex-style home, this unit offers complete privacy with its own separate entrance.

4.96 out of 5 average rating, 444 reviews

Top guest favourite

The exterior of a spacious two-story house features a welcoming porch with decorative railings, flanked by two garage doors. Lush green grass surrounds the driveway, and colorful landscaping adds charm. The clear blue sky complements the neutral-colored siding, creating a bright and inviting appearance.

Home in Winnipeg

Luxury lifestyle in trendy location, king bed

This stylish and spacious place to stay is perfect for families and small traveling working groups. The house is located on the quiet street in the heart of Bridgwater Lakes, desirable location close to all city spots. Overflowing with stylish details and offering a well-designed layout with 18 and 9 ft ceiling, open concept kitchen and dining with a huge island. No pets please(e.g. service dogs); we have severe allergies ;it sends us to an emergency room. Thanks for understanding.

4.95 out of 5 average rating, 123 reviews

Top guest favourite

Home in Winnipeg

Luxury Stay With What Hotels Wish They Had

Designed for those who expect more from where they stay. This luxury show home in south Winnipeg offers premium bedding, plush towels, and a level of comfort you feel the moment you walk in. Enjoy spacious living, large smart TVs, and a fully equipped kitchen for effortless stays. Immaculately clean, private, and thoughtfully designed throughout — a polished, five-star experience that goes beyond the standard and delivers comfort, quality, and ease at every turn.

5.0 out of 5 average rating, 35 reviews

Superhost

Home in Winnipeg

19 min — Downtown. • 3BR- king bed•free parking

🌊 Luxury Lakeview Retreat Wake up to breathtaking lake views in this elegant 3-bedroom, 2.5-bath home—ideal for families, holidays, or group getaways. Designed for comfort, space, and relaxation. ✨ Highlights: • Private deck with lake views • Spacious living area for gatherings • King bed & smart TV (Netflix, Prime, Disney+) • Fully equipped kitchen for group meals • ⚡ Fast Wi-Fi & 🚗 free parking (One of the cushions on the living room couch is a bit dented)

4.61 out of 5 average rating, 57 reviews

Top guest favourite

Home in St. Boniface

Riverfront 4BR Luxe w/ Hot Tub & Fire Pit

Riverfront retreat minutes from downtown! Unwind in the hot tub, gather by the fire pit, or stroll straight into Bois-des-Esprits forest. Inside: 4 spacious bedrooms, 2 baths, grand living room, game lounge with pool table, ping-pong, arcade, gym & smart TVs. Huge kitchen and dining for family feasts. Kayaks, riverside sunsets, walks on a frozen river and year-round adventure await—relax or explore, then book now to secure your dates!

4.95 out of 5 average rating, 125 reviews

Top guest favourite

A quaint cabin is surrounded by lush greenery, featuring a wooden deck with two red chairs facing the entrance. A grilling area is visible on the side, alongside a rustic woodpile. The grassy yard leads into dense trees, providing a tranquil and secluded setting.

Tiny home in Blumenort

Unwind at cozy guest cabin & nature retreat

LISTING since Dec 2021! Lakefront guest cabin with walking trails and amazing sunset views. Located on 120 private acres of oak and boreal forests, meadows, tallgrass prairie, pristine marl lake, and charming homestead. Having been in the family for 4 generations, the property hides treasures like old farm implements and quaint buildings which are quiet remnants of bygone farming days. Tranquil, nostalgic, and photo-worthy!

4.97 out of 5 average rating, 268 reviews