
Condo holiday rentals in Simcoe County
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Top-rated condo rentals in Simcoe County
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Popular amenities for Simcoe County condo rentals
Weekly condo rentals

Lake/Marina Front, Luxury 2 Storie 1500 Sqft At FH
We recently had the pleasure of staying at a fantastic condo in Friday Harbour, and we can’t recommend it highly enough! From the moment we arrived, we were greeted with warm hospitality and a stunning view that took our breath away. The condo itself was a perfect blend of luxury and comfort. It was impeccably clean, stylishly decorated, and equipped with all the amenities one could wish for. One of the highlights of our stay was the private balcony, where we spent many mornings sipping coffee and evenings watching the sunset over the harbor. The location of the condo is unbeatable. Just a short walk to charming local shops, restaurants, and the marina, it offered the perfect mix of relaxation and convenience. Overall, our stay at this condo in Friday Harbour was exceptional. It’s clear that the owners have put a lot of thought and care into creating a perfect retreat. If you’re looking for a memorable getaway, this place should be at the top of your list!

Luxury Getaway @ Friday Harbour Condo at Marina
We had such a peaceful long weekend stay at Ana's! The location was perfect and exactly described; overlooks right into the marina, amazing restaurants just right down the steps and extremely quiet! We didn't hear a single sound from any of neighbours around us. The space looked even more beautiful than the pictures. My husband and I were shocked to see just how incredibly clean the apartment was; not a single speckle anywhere! We were welcomed by a lovely snack basket (which my husband devoured on the first night) and a bottle of wine. Even included amenities in the bathroom which was wonderful since I forgot our toothbrush. The bathroom was so cozy and such a lovely surprise to have a tub. We will definitely be coming back!

Friday Harbour Ground Floor w/ Large Terrance
We had amazing time! Tiana goes above and beyond. The outside patio was so nice and relaxing. Recommend to everyone. Thank you!

Cozy south view suite overlooking the nature trail
Loved our stay! Place was spotless and just as described, and check-in was smooth with clear instructions. Unfortunately the Nature Preserve was closed during our stay, and the pool was closed for maintenance, but Lina was accommodating otherwise. One thing to note is that the unit is right next to a stairwell exit, so if you have a sensitive dog like ours, they may be disturbed by some noises. Thanks again for the great stay!

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

Romantic Stay at Friday Harbour Resort Lake Simcoe
Jack was an amazing host!! Extremely friendly, responsive and helpful throughout the entire process, before & during the stay, and morning of check out. Provided us with very clear instructions including a map if we needed, as well as linked us to the local events / dining page for the resort. The place was spotless! Matched the listing page. Would definitely recommend reserving one of Jack's listings after the great experience we had.

Wildwood HotTub+Indoor/Outdoor Pool+Sauna+GameRoom
Perfect place to have a peaceful break from the city!!

Spacious King Studio - Pool, Hottub, Kitchenette
Our stay was exactly what we were looking for quiet, nice location, good price communication was clear and concise. If we are ever that way again we would definitely stay here again. Would be nice to stay more than one night to enjoy the area and what the location has to fully offer.
Pet-friendly condo rentals

Large 3BR Modern Luxury Escape | Walk to Blue
It was great staying at Karim’s place. The location is ideal for visiting Blue Mountain with restaurants and grocery stores near by. Also, Karim was very responsive and made sure we had everything we needed.

Spring Sneak Away | Blue Mountain
Loved our stay at the moose cabin even though it was short. We just needed a place to break a long drive up. Unfortunately we arrived late and left early because the location was awesome!! Cabin very comfortable. The communications were fast host was very helpful. Wish we could have stayed for a week!!!!

Stylish & Spacious 2 Bdrm/2 bths/2 balc Condo Loft
We had a great stay! The place was exactly as described- clean, comfortable, and well-equipped. It’s in a perfect location, within walking distance to both Blue Mountain Village and the beach, which made it super convenient for our trip. The host was friendly and responsive, and everything went smoothly from check-in to check-out. Highly recommend!

Base of Blue Mountain, Modern Studio
Kate was a responsive host and the suite was comfortable. The king sized bed was a dream. The kitchen had everything we needed and there were ice cubes in the freezer upon our arrival.

Convenient Garden Walkout to Pier, 2BR+2bath Condo
Kin provided us with a beautiful place to stay and gave very clear instructions on what to do for check in, check out, where garbage can be disposed, and was super responsive when we had any questions. The pool and hottub were out of service at this time so giving us a heads up about that would be the only thing we would have changed! Everything else was perfect and we had everything we needed, we will definitely be back! Thank you so much Kin for providing us with a wonderful and stress free place to stay!

Lux Studio in Horseshoe Valley
Very accommodating and flexible, and they didn’t hesitate to approve our last-minute late check-in request.

Sunsets by the Lake at 2BR 2BA Condo in Innisfil
We had a lovely family stay at these peaceful and beautifully located apartments. Surrounded by nature and calm, it was the perfect escape from the city. The apartment was very clean, and the kitchen had everything we needed to cook and feel comfortable. The host was kind, responsive, and made us feel truly welcome. We appreciated the quiet atmosphere, the fresh air, and the overall coziness. Highly recommended for families looking for a relaxing getaway!

Creekside Smart Studio at Blue Mountain
Small but has everything we needed. Fantastic t.v. A little bit dated but clean and comfortable
Condo rentals with a pool

*Blue Mountain Village* Walk To Blue, Pool, HotTub
Great location, really close to the village, golf, trails and the Scandinave Spa. Condo unit is exactly as advertised with a comfy sofa to lunge on. Beds are comfortable and all linens and needed amenities were easy to find and use.

Close to Village, 2 Bedrooms , Rivergrass
Bruce was super helpful and has a great place. Would highly recommend!

Out of the Blue - Outdoor Pool / Shuttle to Blue
We lived our visit to this condo! It was warm and cozy and exactly as advertised. My daughter loved the loft area and chilling out on the pull-out sofa. We even went for a swim - the pool facilities are lovely! Thanks for a great stay - we will be back!

Elegant 2bdrm/2bath condo at Friday Harbour
Mary was very accommodating! The place was clean. The appliances were in great condition. She provided everything that we needed during our WHOLE stay. Most places we’ve been at jist gives us a starter kit, but Mary went above and beyond to make our stay enjoyable, and well taken care of. She even gave our kiddos bubble wands when we came in. It’s the little touch that gives the biggest meaning. Thank you! The only thing we wish there was, was more storage. We kept our clothes in our luggages. The rack could use some storage bins maybe? So that we can store clothes in it without it calling off the shelves. But overall the stay was just great! If we come back to Friday harbour again, we sure will come back to Mary!

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

Ski in/out @ North Creek W King bed! New Hot Tub
Great location, walking distance to Blue Mountain Village! Stephanie was incredibly friendly and helpful with instructions for check-in and check-out. Would absolutely stay here again!

Friday Harbour Luxury Condo Escape, Sleeps 4
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

Mountain Side One Bedroom
My husband and i make a date once a month to go away locally for a night (kid free) and this place was so cozy and perfect! We had dinner outside on the picnic table on the deck, bed was super comfortable.
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- Blue Mountain Village
- TPC Toronto at Osprey Valley
- Port Carling Golf & Country Club
- Osler Bluff Ski Club
- Horseshoe Resort
- Devil's Glen Country Club
- Georgian Bay Islands National Park
- Beaver Valley Ski Club
- Mount St. Louis Moonstone
- Snow Valley Ski Resort
- Lake Joseph Golf Club
- Hockley Valley Resort - Golf, Spa and Ski
- Muskoka Lakes Golf and Country Club
- Angus Glen Golf Club
- Lakeridge Ski Resort
- The Club At Bond Head
- The Georgian Peaks Club
- Muskoka Bay Resort
- Caledon Country Club
- Alpine Ski Club
- Wooden Sticks Golf Club
- Dagmar Ski Resort
- National Pines Golf Club
- Barrie Country Club