Vacation rentals with a pool in Milton

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Milton

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

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Guest favorite

Rental unit in Downtown Toronto

4.93 out of 5 average rating, 15 reviews

Ambient Vibe Downtown | CN Tower + Lake View Condo

The most exclusive condo where you can set the vibe by changing all the lights to your favourite colour. The perfect getaway and a home away from home. Immerse yourself in this two bedroom, two washroom Airbnb, with the perfect view of the CN Tower, lake and city skyline from the private balcony. Enjoy one of the only rooftop pools/terrace with unparalleled views of the city and cabanas/sun beds available to all guests, with everything you need to make your stay exceptional. Best location in TO

Superhost

Home in Aldershot

4.89 out of 5 average rating, 18 reviews

Four seasons Pool Retreat

6 bedrooms, 4 washrooms, pool, large, kitchen and family room. Mins from lake, restaurants, shopping, bars, cafes and so much more. Central, yet quiet neighbourhood. Relax and Enjoy our indoor pool available year long. Fully equipped kitchen and family room perfect for a large family. Comfortably sleep in our high-end mattresses in a thought-through decorated home. Hosting has been my passion. Super host 6 years in a row we plan to offer you the same comfort we have provided guests over years

Guest favorite

Guest suite in Doon South

4.98 out of 5 average rating, 111 reviews

The Oasis

**Hot tub open until Dec 1st**. Bright, spacious, and homey private suite. Large private backyard, fire pit area, and several walking trails right out the back gate. Retreat to the spacious walk out basement suite with 70” TV home theater, elliptical trainer, desk space and plenty of windows open to the forest view behind the house. Beautiful Doon neighbourhood within minutes of the 401. Plenty of shopping and eating choices within a few minutes drive. Hot tub and pool closed until spring 2025.

Guest favorite

Guest suite in Halton Hills

4.94 out of 5 average rating, 17 reviews

In ground heated pool, hot tub and putting green!

Well located home is 35 minutes from Airport, located close to several public golf courses. Five-minute walk from old Downtown featuring bars, restaurants, and shopping. Farmers Market on Saturdays. Beautiful heated salt swimming pool, 5-person hot tub, 5-hole putting green, firepit, gas bbq, cabana, patio furniture on stone patio. Kitchen has stovetop, fridge, dishwasher, toaster oven, microwave, air fryer and all kitchen necessities. Free Wifi, Netflix, cable TV all in a private peaceful home.

Superhost

Bungalow in Burlington

4.74 out of 5 average rating, 117 reviews

Private HotTub Pool; Sleeps 12/Min 4: Adults Only

- **Guests:** 4 min. to 12 ADULTS ONLY; No parties or unregistered guests. - Cottage Vibe Cozy, secluded. - Pool June to October. - **Hot Tub:** Year-round. CLOSED 10:30 PM. - Ping pong table. - AC/furnace. New!. - BBQ grill. - Entrance Private. - Short walk to the lake. - **Owner:** Lives in a separate apt. below as per town laws. See satisfied guest reviews. - Towels:Provided; bring beach towels. - Garbage out at Thurs. at 7:30 AM. Thank you for your cooperation! Enjoy your stay

Guest favorite

Home in Aldershot

4.92 out of 5 average rating, 25 reviews

Holiday Retreat with Pool

This unique place has a style all its own. Minutes from lake, steps from restaurants, shopping, bars, cafes and so much more. Central, yet quiet neighbourhood. Relax and Enjoy our large backyard and the pool with family. Our fully equipped kitchen and kitchenette for a large family. Comfortably sleep in our high-end mattresses in a thought-through decorated home. Hosting has been my passion. Super host 6 years in a row we plan to offer you the same comfort we have provided guests over years!

Guest favorite

Rental unit in Ariss

4.95 out of 5 average rating, 138 reviews

Rural Retreat, near to Elora

A peaceful , rural, retreat in Ariss. Hot tub, great bird watching. Well situated between Elora, Fergus, St Jacobs and Guelph. Visit Cox Creek Winery, Kissing Bridge, G2G & Cotton Tail hiking/biking trail, snowshoeing, snowmobile trails & Chicopee Ski Resort. Two dogs on the property. Walkout basement, king bed, portable crib (on request) shower, kitchenette, seating area, natural light. Large backyard, firepit, barbeque, outdoor eating area. Keyless, separate, private entry, free parking.

Superhost

Cottage in Cambridge

4.88 out of 5 average rating, 8 reviews

Waterfront home with Pool, Boat Ramp/Canoe/Kayak

This vacation home has beautiful views, southern exposure , flower gardens and greenery all around. Surrounding the pool in the back yard beside the lake there is a flagstone patio area with a campfire pit. A perfect spot for watching dreamy sunsets. There is a fabulous pool 17x36 ft with a big deck surrounding it. A picnic table and BBQ on the upper patio terrace by the cottage, overlooking the lake. We have lots of gathering places to lounge around and relax in the outdoor patio furniture.

Guest favorite

Rental unit in Downtown Toronto

4.94 out of 5 average rating, 126 reviews

5-Star Condo beside CN Tower

Mere steps to Toronto’s most popular attractions including the CN Tower, Ripley’s Aquarium, Rogers Centre, Roy Thomson Hall and the Metro Toronto Convention Centre. Located in the entertainment district at the heart of the city with a wide selection of the finest dining, shopping, night life and entertainment. Amenities including an infinity outdoor rooftop swimming pool and fitness center. Enjoy 5 star welcome from concierge. Great for families, solo adventurers and business travelers!

Guest favorite

Guest suite in Lorne Park

4.91 out of 5 average rating, 150 reviews

Full apt on Upper floor near HWY - S Mississauga

Get the privacy & convenience of a hotel and comfort of a home. In the heart of Lorne Park in S. Mississauga, the apartment is built on the upper floor of a house with a separate entrance from the rear. One minute to QEW, 17 minutes from the airport, & 20 minutes to downtown Toronto, this spacious apartment is self-sufficient with a new, full kitchen with appliances, bathroom, laundry & parking. Ideal for all types of stays. A lot of our guests are repeat guests. No smoking property.

Guest favorite

Rental unit in Dunnville

4.95 out of 5 average rating, 145 reviews

B&B @ Hunter's Heavenly Haven

Enjoy this non-smoking In-law Suite in our home which is situated on a beautiful Country Property in Dunnville, ON, which sits at the Mouth of the Grand River and 20 min. to the beaches of Lake Erie. We are located within 1 hrs drive to Niagara Falls, Niagara Wineries, and 1 hr & 1/2 to the CN Tower and the many things to do in Toronto. This property has walking trails, a pond, and use of the pool. So come and enjoy the beaches, tourist attractions or just sit back and relax!

Guest favorite

Guesthouse in Caledon

4.86 out of 5 average rating, 42 reviews

Caledon rural apartment with hot tub and pool

Come and enjoy the outdoors in a peaceful modern apartment in rural Palgrave. 6 minutes from Caledon Equestrian Park. Owners live on property and we don’r allow permit parties or events of any size. 2 Bedrooms, each with luxury king beds and bedding. Spa shower and toiletries. Apartment is self contained. No pets allowed and no smoking inside, shared use of heated salt water pool (open June 1st to Sept 30) and hot tub. No weddings, parties, or showers allowed