
Vacation rentals with a kayak in Midland
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Top-rated kayak rentals in Midland
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Fire & Ice Spa w/ Private Sauna!
Welcome to the most unique suite at Friday Harbour Resort! Relax, refresh and unwind in your very own private spa experience which includes large infrared sauna, 3 indoor fireplaces and outdoor fire table. Kiss those winter blues away while you warm up in the most cozy suite, perfect for a romantic getaway. Every stay includes a bottle of bubbly to toast with the one who is most important to you! Make Fire & Ice your next vacation destination and reconnect in a most romantic, relaxing suite!

Relax at The Rock: Muskoka Waterfront Cottage
Enjoy fishing, swimming and paddling 22km of the green and black rivers. Paddleboat, canoe, 2 kayaks, and a SUP provided. Take the short 5 minute stroll into town for ice cream or fresh baked treats. Lay out on the elevated deck or in the screened in porch with a good book. End your evening at the riverfront firepit. Nearby day adventures include hiking, golfing, parks, beaches, breweries, casino rama, and downhill skiing at Mount St Louis Moonstone and Horseshoe Valley (30 minute drive).

Muskoka Stunning Cottage On Little Lake
Surrounded by Little Lake, this gem provides a relaxing getaway with amazing water views. Spend your days peacefully rowing on the lake or having a picnic on the private beach, and your nights settling by a crackling fire. The home itself is plenty spacious for unwinding and getting a good night's sleep, views all-inclusive. Explore Port Severn Park right next door and play around in the public beach and splash pad. For more adventure, hike the beautiful Georgian Bay Islands National Park.

Forest Harbour Hideaway
Situated on beautiful Georgian Bay, this cozy and quaint waterfront cottage delivers an escape from reality with all the comforts of home! With private access to the water and dock, and two public beaches within a 5 minute walk, unwind, relax and reset in the heart of our quiet cottage neighbourhood. Both Midland and Orillia are 20 minutes away by car, where you can find a variety of shops, restaurants and local attractions, like Sainte-Marie Among the Hurons and Wye Marsh Wildlife Centre.

Tiny Luxury Cottage with Hot Tub
This tiny luxury 2 bedroom cottage with loft is perfect for a romantic couple or small family getaway. Nestled on 1.5 acres among majestic trees and granite outcrops, creates beautiful views from the deck with BBQ, fire pit, hot tub or massive windows throughout the cottage. Water dam and river across the road create relaxing waterfall sounds that are heard from deck or enjoy it close up from the private shoreline deck and dock. Explore the Muskoka River on the kayak, SUP or river tubes.

Log Cabin on the Lake Bed and Breakfast
Log Cabin on the Lake Bed and Breakfast We provide a 1st morning continental breakfast A Lakefront getaway for couples with an amazing view. Experience tiny home living in a custom built Log Cabin. Landscaping provides privacy for all parties (owner next door) we have parking for a boat , with 2 launches within 5 min. One into Morrison Lake the other into the Trent Severn . cross country skiing, ice fishing, water skiing swimming boating. Ready to escape, our Log Cabin could be it.

The Friday Flat | Sunny Escape by the Marina
Enjoy access to all of Friday Harbour's world-class amenities, including a golf course and sandy beach. Take a dip in the outdoor pool and explore the kilometres of scenic walking trails that wind through the Nature Preserve Located just a short drive from Toronto, Friday Harbour offers the perfect escape from city life. Spend your days exploring the shops and restaurants of the promenade, or venture out onto the lake Come experience the ultimate waterfront getaway at Friday Harbour

Muskoka Hideaway-hot tub/private trails/wood stove
Hidden amongst the trees in the middle of Muskoka, this Hemlock log cabin boasts high ceilings and a true "cabin in the woods" feel. Its not hard to relax and unwind with a coffee in front of the fire, or go and explore along the private forest trails (1-2k of walking trails). As well, downtown Bracebridge is a convenient 10 minute drive away with all amenities. There is a veggie garden on the property and depending when you come you can pick away at it :) Pets are welcome in the home!

The Bay View Cottage w/hot tub
Welcome to our 4 season, 2 family cottage with Georgian Bay views and a hot tub. 3 min walk to the cutest small beach that has stunning sunsets, 12 min to Awenda Provincial Park which has great hiking, beaches, biking and winter activities. Short drive to Balm Beach. Downtown Midland has great restaurants and everything a quaint downtown has to offer. Winter has so much to offer including ice fishing, OFSC snowmobile trails, cross country skiing and much more. Max occupancy is 8 adult.

Stix N Stones (Includes Light Breakfast & Kayaks)
Nestled in the woods on Walkers Point, this is a great opportunity to reconnect with nature. We promise when you leave you’ll appreciate the forest as much as the water that surrounds us. Although we are not on the water, we are a 3min drive to a semi-private beach. Kayaks & life vests included (& delivered). Snowshoes incl in winter. Light breakfast is yogurt & fruit. Short distance to renowned hiking trails, Hardy Lake Park, Sawdust City & Clearlake Brewery, Muskoka Winery.

Moon Rock Cottage BnB With Gorgeous Waterfront
Welcome to Moonrock! Our beautiful waterfront cottage is nestled in the heart of Muskoka. A quick two minute drive to Bala for the shops, Ice cream, restaurants and our local bakery. Close to trails for hiking or relax on the dock or deck. Not only will you enjoy all the creature comforts offered at our cottage, you can explore the local lakes, stores, natural features and great local restaurants in the area. A true natural getaway for you and your family!

The Muskoka River Chalet - The King's Den
Welcome to Muskoka River Chalet! **Please read full listing description before booking.** Relax in your fully private one-bedroom walkout apartment with private kitchen, cozy living room, featuring smart TVs and toasty fireplaces. Explore our shared outdoor spaces along 60' of waterfront. Indulge in the hot tub for relaxation. Just minutes walking to town for shopping, dining, and nightlife. Book now for a perfect blend of comfort and convenience!
Popular amenities for Midland kayak rentals
House rentals with a kayak

Welcoming Waterfront Cottage

River's End: Explore the river by kayak or canoe!

Relax & enjoy fall- 20 min drive to Blue Mnt

[Casa Luna]Chic Lakehouse| BBQ|HotTub|LakeViews

Your Bala home away from home

Waterfront Retreat | 6BR • Hot Tub • Private Beach

Victoria Harbor cottage

Midland ON - Lakehouse
Cottage rentals with a kayak

Waterfront cottage on quiet Spence lake

Riverfront Cottage with HotTub

Lakefront Cottage with Sauna and Steam Room

Waterfront @Muskoka Pines /kayaks/bbq/firepit

Spacious Cottage Escape with Lakeside Hot Tub

Waterfront Paradise on the Georgian Bay

Cottage on the lake

Charming Lakefront Bala Cottage
Cabin rentals with a kayak

Oak Cabin on Sparrow Lake

The Blue Cottage

Gorgeous Muskokan Cottage on Six Mile Lake

90 Min to GTA Waterfront Cottage in Kawartha Lakes

Cozy Severn River Family Cottage

Beautiful Six Mile Lake Muskoka

Cabin by the Lake

Charming Muskoka cottage, amazing views!
Quick stats about vacation rentals with a kayak in Midland

Total vacation rentals
Explore 30 vacation rentals in Midland

Nightly prices starting at
Midland vacation rentals start at G$16,753Â GYD per night before taxes and fees

Verified guest reviews
Over 1,440 verified reviews to help you choose

Family-friendly vacation rentals
30 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wi-Fi availability
30 of Midland vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Midland rentals

4.8 Average rating
Midland stays are highly rated by guests—averaging 4.8 out of 5!
Destinations to explore
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- Apartment rentals Midland
- Rentals with pools Midland
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- Rentals with a fire pit Midland
- Cottage rentals Midland
- Pet-friendly rentals Midland
- Rentals with a washer and dryer Midland
- Rentals with a fireplace Midland
- Rentals with outdoor seating Midland
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- Family-friendly rentals Midland
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- Rentals with an EV charger Midland
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- Rentals with a hot tub Midland
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- Blue Mountain Village
- Snow Valley Ski Resort
- Beaver Valley Ski Club
- Osler Bluff Ski Club
- Devil's Glen Country Club
- Craigleith Ski Club
- Rocky Crest Golf Club
- Port Carling Golf & Country Club
- Mount St. Louis Moonstone
- The Georgian Peaks Club
- Lake Joseph Golf Club
- Muskoka Lakes Golf and Country Club
- Muskoka Bay Resort
- The Club At Bond Head
- Windermere Golf & Country Club
- Georgian Bay Islands National Park
- The Georgian Bay Club
- Barrie Country Club
- Toronto Ski Club
- Alpine Ski Club
- Mansfield Ski Club
- Hawk Ridge Golf & Country Club
- Heritage Hills Golf Club
- Springwater Golf Course