Family-friendly holiday rentals in Milton

Tranquil Tiny House Retreat 4-Season Radiant Floor

Take it easy at this unique cabin experience in the city. The Tiny House is a private 9’ x 12’, fully insulated, 4 season cabin with a couch, kitchenette with running water, queen bed, Loftnet hammock & outdoor shower. Enjoy the natural beauty of our half acre tree-filled backyard, yet still close to downtown Guelph. This is a glamping experience that requires appreciation for tiny house living. Guests have access to a separate portable washroom, by walking about 100ft to the back of the yard.

Cozy 2 Bedroom Basement, 2 Queen Beds, 1 Parking.

Brand new basement 2 Bedrooms with comfortable Queen bed in each room and one full washroom legal basement, seprate entrance and 1 parking in Milton. Have fun with your family/ friends. Gather around the breakfast dining table, comfortably seating four. Stay connected and entertained with high-speed Wi-Fi and a smart TV. Laundry, free parking. Minutes to Kelso Park, Mattamy Cycling Center, Milton Go station. Border of Burlington, Oakville and Mississauga, 15 minutes to Toronto Premium Mall.

The Clayhill Bunkie

Looking for a place to get away that’s semi off-grid or a place that’s kind of like glamping? On The Bruce Trail and minutes from Silvercreek & Terra Cotta Cons. areas, the Credit River, the villages of Glen Williams &Terra Cotta, &the town of Georgetown. Spend your day hiking, cycling, antique hunting, tubing, or site seeing, then order in or grab take-out and come relax by a roaring fire. Firewood is included, adding great value to your stay. You WILL hear wildlife and farm animals here.

Spacious and Comfy 2 BR Suite

Discover tranquility in our 2-bedroom legal basement apartment, nestled in Milton’s quiet and peaceful neighborhood. Enjoy an open-concept living room with 8.5 ft ceiling, and 2 roomy bedrooms; perfect for couples or families to relax in this comfortable, private, retreat. Easy access to Oakville, Burlington, Mississauga, and Toronto Pearson Airport, and minutes away from Toronto Premium Outlets, Mattamy Cycling Centre, and scenic trails, makes this location ideal for both work and play.

Luxury Guest Suite

Welcome to our cozy basement apartment! This modern Airbnb is located in a peaceful residential neighborhood 40 min drive from Toronto downtown and an hour from Niagara Falls. The well-lit space features a comfortable queen-sized bed, ample storage in the spacious closet, and a beautifully designed interior with natural light flooding through large windows. Note: We have 2 single folding matresses available to place on the floor in the living room. Extra linen and pillows are provided.

Luxury tiny home on peaceful country estate

Escape to Heirloom Tiny Home - where macro luxury meets a micro footprint. Nestled on 23 peaceful acres, surrounded by aspen and pine forests, just 10 minutes from the picturesque town of Elora. Wake up to serene pond views as horses and sheep graze in your view. Organic linens, artisanal soaps, and a spa-like bathroom soothe the senses. Cozy up by the indoor fire and gaze at the stars. Enjoy fine dining at the Elora Mill and Spa, enjoy popular shops or hike the Elora Gorge nearby.

Halton Hills Hideaway_Private Suite

🌿 Halton Hills Hideaway – Cozy Basement Suite Near Downtown Georgetown ✨ What You’ll Love: 🚪 Private Basement Suite – Separate entrance & no shared areas 🛏️ Queen Bed – Comfy and perfect for solo travelers or couples 🌳 Garden Views – Enjoy calming green views from your lookout window 🧼 Clean & Cozy – Thoughtfully prepared for a peaceful stay 🏘️ Charming Neighborhood – Quiet, friendly, and safe 🔍 Check the amenities section for full details—we’d love to host you!

Winter Escape Tropical Dome! Animal Lovers Dream

Jungle Dome on a farm in Burlington! Enjoy a tropical stay in our 500 square foot geodesic dome “glamping” greenhouse dwelling! Sleeps 4. Complete with a fish and turtle pond and filled to the brim with tropical plants! Designed to be a tropical vacation getaway when you can’t get away to the tropics! Situated on a 5 acre animal farm where guests can feed and interact with goats, horses, highland cows, sheep, pigs and poultry. An Animal Lovers Dream!

Arcade Bar For 2

This basement apartment is the getaway you've been waiting for! ✅ Pool table ✅ Bar ✅ Arcade ✅ Cozy bedroom ✅ Large Soaker tub(no jets) Should I go on? Hours of fun for a night-in or a cool place to stay on a trip through town. Whatever your journey, let us be the destination. 🧳🛸🛎 Share our home and experience an unforgettable stay! 🎮🎱🍹 The suite is a fully private apartment that sleeps 2 and is not suitable for events.

Backyard Oasis Guesthouse.

POOL IS CLOSED TILL MAY 2026 Welcome to our cozy walk-out basement apartment with no kitchen. It is a completely private unit with separate entrance. Perfect for making some memories at this unique and family-friendly place. Backing on to the Sixteen-mile creek, this backyard oasis has a sun-drenched inground pool surrounded by mature perennial gardens, a new manufactured stone patio, with upper and lower shaded lounge areas.

Blue Haven Retreat, Downtown Milton's Hidden Gem!

Situated in Downtown Milton’s vibrant and fun neighbourhood, where you’ll enjoy all the benefits of being within walking distance to boutique shopping, restaurants, and the stunning Mill Pond! You’ll also be minutes to Halton’s best conservation parks where you can embark on all of your favourite outdoor adventures! FROM THE AIRPORT 25 mins from Pearson International Airport 40 mins from Hamilton Airport.

Warm & Cozy Home w/3 Bedrooms Free WIFI & Parking

Enjoy a peaceful stay in our modern 3-bedroom Milton home! Perfect for families or business travelers, featuring a fully equipped kitchen, fast Wi-Fi, private parking, and cozy living space. Minutes from Kelso, Rattlesnake Point, and shops. Please: no parties, no pets, no smoking. Quiet hours after 10 PM. Entire home is yours—no one lives in the basement. Book your relaxing getaway today!