Vacation rentals with a pool in Lake of Bays

Find and book unique homes with a pool on Airbnb

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Popular amenities for Lake of Bays rentals with a pool

House rentals with a pool

Guest favorite
A pristine in-ground pool is surrounded by a well-maintained patio and grassy area. The house features a modern exterior with a sloped roof and accessible steps leading to a deck adorned with planters. Sunlight reflects off the water, creating a calming ambiance.
Home in Orillia
4.96 out of 5 average rating, 28 reviews

Cute and Cozy House

BrianRating, 5 stars1 week ago
Anzhelika’s place was great. The house and property were really well-maintained and exactly as described in the listing. She was a very helpful and accommodating host. The location was great, nice and close to downtown and other amenities. My family and I, including two kids under 10, were very happy with the accommodations. I’d definitely recommend staying here
Top guest favorite
An outdoor swimming pool is surrounded by a wooden deck, offering space for relaxation. A serene landscape of lush green grass and tall trees stretches into the distance, providing a picturesque backdrop. A few lounge chairs are visible near the pool's edge.
Home in Kearney
5 out of 5 average rating, 25 reviews

Rondial Cottage: Lrg. Kitchen, Hot Tub, Pool &More

QuintenRating, 5 stars2 weeks ago
Property and home are extremely beautiful, we had great weather and spent most the weekend outside. Definitely considering booking this cottage again in the future. Thanks for the stay
Guest favorite
A modern living area is highlighted by a sleek, electric fireplace beneath a large flat-screen TV. A rustic accent wall features wooden panels and decorative art. A comfortable gray sofa and a table set for dining complete the welcoming space, complemented by blue and natural tones.
Home in Innisfil
4.92 out of 5 average rating, 50 reviews

2 Bd Boardwalk Condo Patio Oasis

JoannRating, 5 stars2 days ago
We really enjoyed our stay at Friday Harbour so much so I think we’re gonna be coming back again next year thank you again so much!!!
Guest favorite
A serene outdoor space features a sparkling pool surrounded by a mix of greenery, including a neatly trimmed tree and ornamental stones. A wooden fence provides privacy, while decorative white stones add a clean touch to the pool area.
Home in Barrie
4.92 out of 5 average rating, 95 reviews

Luxurious 4BDRM-King Bed-Barrie-near Snow Resorts

DianeRating, 5 stars1 week ago
This house was perfect for our large group: for couples and a baby. Having the pool was a bonus that we really appreciated in the warm weather. The kitchen was extremely well equipped, and there were enough linens as well as pool towels for us all. There was plenty of space for everybody as the rooms were all quite large, particularly the master bedroom. The house were incredibly accommodating when we realized after checkout that we had left a couple of items behind. They were able to make arrangements for us to retrieve them several days later back in Toronto! I definitely can recommend this house.
Guest favorite
A refreshing swimming pool is surrounded by a paved patio and lush greenery. An umbrella provides shade over an outdoor seating area featuring lounge chairs. The vibrant colors of the landscaping complement the clear blue water, creating a tranquil and inviting outdoor space.
Home in Midland
4.8 out of 5 average rating, 45 reviews

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

AnneRating, 5 stars4 months ago
We were so satisfied for being the first time we booked a AIRBNB. We like the clean airy atmosphere when we walked in. Kitchen was fully equipped for our needs. ( I do a lot of cooking ). We were there for 6 weeks. Our hosts were always in contact to make sure our needs were met. We so enjoyed Midland and everyone was so friendly. We highly recommend this AIRBNB👍💗
Top guest favorite
Home in Gravenhurst
5 out of 5 average rating, 17 reviews

Luxury Resort Villa on Muskoka Bay Golf Course

DebRating, 5 stars4 months ago
Excellent stay and great amenities
Guest favorite
An above-ground pool with a wooden deck is positioned in a grassy area, bordered by reeds and a tranquil body of water. Two metal ladders are attached to the pool, and multiple chairs and storage items are visible nearby, suggesting a relaxed outdoor setting.
Home in Elmvale
4.89 out of 5 average rating, 19 reviews

Cozy Lakefront Cottage with Hot tub and Pool.

KreenaRating, 5 stars9 months ago
We went to this cottage for a beautiful romantic weekend getaway and we were happy we got that. The owner of the cottage Necker was very kind and helpful, absolutely loved the place and there was plenty of water activities to do. It was easy to check in, communicate and plenty of peaceful vibes. Recommended 100%, please go visit this cottage it is very well worth it. P.S: we loved the character of the cottage with little artpieces and wall art from all over the globe 🌎.
Guest favorite
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
4.95 out of 5 average rating, 41 reviews

Comfort, Luxury and Relaxation

LauraRating, 5 stars5 days ago
Aaron was such a wonderful host! Extremely responsive, communicative, and pleasant to deal with. I’ve stayed in his unit before and will absolutely stay again. It’s always very clean and tidy, warm, comfortable, and welcoming. Thank you again for being such a pleasure and allowing me to stay in your space!

Condo rentals with a pool

Top guest favorite
A rectangular hot tub is set under a wooden pergola, featuring steps leading down into the water. Surrounding greenery and a glass railing provide a sense of openness. Sunlight casts shadows across the stone tiles and water surface.
Condo in Innisfil
4.96 out of 5 average rating, 54 reviews

Walkout to Courtyard w/ Pool, Hot Tub and Fire Pit

StephanieRating, 5 stars1 week ago
My family and I had the best time at Friday Harbour accommodated my Adriana. Her place was beautiful and clean. Literally everything we needed was already thought of and stocked. The condo was walking distance to the main boardwalk area where we found lots to do. My family and I will definitely revisit this condo soon!
Guest favorite
A spacious courtyard features a tranquil pool surrounded by modern condominium buildings. Lush greenery enhances the area, while lounge chairs are positioned near the water. Bright blue skies and natural light create a cheerful atmosphere, ideal for relaxation and leisure activities.
Condo in Innisfil
4.89 out of 5 average rating, 143 reviews

Friday Harbor Upscale 1Bed+Sofabed+Pool Option

Tanuja KajalRating, 5 stars3 weeks ago
We had an amazing time at Kevin’s place! It was the perfect peaceful getaway from the city. The home was clean, comfortable, and exactly what we needed to relax and unwind. Kevin was a great host—very responsive to messages and incredibly accommodating, even allowing us a late check-out which we really appreciated. He provided clear and detailed instructions for accessing the place, which made everything smooth and easy. Thank you, Kevin, for being so thoughtful and welcoming. We’d definitely love to come back again!
Superhost
The image showcases a spacious outdoor area featuring a swimming pool surrounded by landscaped gardens. Modern buildings with balconies are visible in the background. Seating areas with tables and chairs are arranged around the pool, providing a relaxed atmosphere for guests.
Condo in Innisfil
4.91 out of 5 average rating, 142 reviews

Beautiful Condo, 2 Bedrooms and a Den in a Resort!

AnisaRating, 5 stars1 month ago
My kids & I had a fantastic experience at this Airbnb. The space was exactly as described—clean, comfortable, and well-equipped with everything I needed. The host was incredibly responsive and helpful, providing clear check-in instructions and great local recommendations. The location was perfect—close to everything, but quiet enough to relax. I would definitely stay here again and highly recommend it to anyone visiting the area!
Guest favorite
A modern living space features a cozy sectional sofa and a small coffee table on a patterned area rug. A minimalist dining area is visible with a bowl of fresh fruit and simple seating, while large windows allow natural light to brighten the room.
Condo in Innisfil
4.89 out of 5 average rating, 19 reviews

Enjoy your stay at a cozy One bedroom apartment!

YugrajRating, 5 stars3 months ago
"Peaceful and Convenient Stay!" I had a great stay at this Airbnb! The place was very peaceful, making it perfect for relaxation. The location is incredibly convenient—just a 2-minute walk to Starbucks, FH Finefood grocery store, and plenty of restaurants. It made everything super easy, whether I needed coffee, groceries, or a nice meal. The host was also responsive and helpful. I’d definitely recommend this place and would love to stay again.
Guest favorite
The image shows a private pool surrounded by modern architecture, with a spacious deck area composed of large stone tiles. Planters with greenery are positioned along the edges, enhancing the serene atmosphere. The pool features light blue water and is set against a backdrop of multi-story buildings.
Condo in Innisfil
4.94 out of 5 average rating, 115 reviews

Friday Harbour Luxury Condo Escape, Sleeps 4

SoniaRating, 5 stars9 months ago
My boyfriend and I stayed the weekend, it was a great location, Joe was very responsive and friendly! We had only 1 concern with the bbq that was not clean, but it has been handled with effectively. Overall space was very clean, it was easy to find kitchen supplies, and other items in the house! A great location with stores, restaurants at a walking distance, and other attractions within a 30 minute drive
Guest favorite
An outdoor pool area features a modern design with lounge chairs positioned along the water's edge. A wooden pergola provides shaded seating. Surrounding greenery and contemporary building façades enhance the space, creating a relaxing setting for guests.
Condo in Innisfil
4.93 out of 5 average rating, 115 reviews

Exceptional 2+1 ground floor condo @Friday Harbour

VictoriaRating, 5 stars2 weeks ago
Loved this place so much! Shai was amazing. Definitely will be coming back!
Guest favorite
An aerial view captures the layout of Friday Harbour, featuring an expansive marina surrounded by lush greenery and residential buildings. The coastline, with a sandy beach and ample water access, provides recreational opportunities. The serene water reflects the natural beauty of the surrounding landscape.
Condo in Innisfil
4.84 out of 5 average rating, 180 reviews

Marina view at Friday Harbour 2bd/2bth Pool option

Joanna LRating, 5 stars12 months ago
Immaculately clean, spacious, and Beautiful condo. It had everything we need and a few steps to the marina. Easy instructions to get inside and parked. I highly recommend!
Guest favorite
An open living area features a deep green sofa, a round coffee table, and a warm rug on light wood flooring. Natural light floods through large glass doors adorned with teal curtains, framed by plants and decorative wall art, creating a cozy and vibrant atmosphere.
Condo in Innisfil
4.98 out of 5 average rating, 58 reviews

Bohemian Luxury at Friday Harbour Resort Simcoe

DhrumilRating, 5 stars1 day ago
Stayed here for a weekend, the place was as described and the location was great. It was a walkable distance to everything, and Jack was great host who gave accurate and prompt instructions to check in and all the other questions we had. Would definitely recommend the place to friends and definitely would come back.

Quick stats about vacation rentals with a pool in Lake of Bays

  • Total rentals

    50 properties

  • Nightly prices starting at

    G$8,368 GYD before taxes and fees

  • Total number of reviews

    1.5K reviews

  • Family-friendly rentals

    40 properties are a good fit for families

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wifi availability

    50 properties include access to wifi

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