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Midland, Ontario Boat Rentals

Page 1 of 124 listings

Go Fast in Penetanguishene, Canada with Powerquest 290 Enticer Bowrider
Powerboats in Penetanguishene · 5 guests

Go Fast in Penetanguishene, Canada with Powerquest 290 Enticer Bowrider

New
$236/hour
Exclusive Getaway for 10 People in Collingwood
Events in Collingwood · 10 guests

Exclusive Getaway for 10 People in Collingwood

5.0
$327/hour
Regal 3360 Motor Yacht Rental in Orillia, Ontario
Events in Orillia · 8 guests

Regal 3360 Motor Yacht Rental in Orillia, Ontario

5.0
$153+/hour
Luxury Day Charter from Downtown Barrie and Friday Harbour
Powerboats in Barrie · 12 guests

Luxury Day Charter from Downtown Barrie and Friday Harbour

5.0
$182+/hour
Professional Luxury Yacht Charter in the Muskoka Lakes
Events in Muskoka Lakes · 12 guests

Professional Luxury Yacht Charter in the Muskoka Lakes

5.0
$473/hour
Private Unique 34' Beautiful Mark Twain Boat In Toronto, 8-10 persons, Sleeps 6
Events in Innisfil · 8 guests

Private Unique 34' Beautiful Mark Twain Boat In Toronto, 8-10 persons, Sleeps 6

4.9
Superowner
$127/hour
28' Luxury Charter Serving Lake Simcoe and area
Events in Innisfil · 6 guests

28' Luxury Charter Serving Lake Simcoe and area

5.0
$127/hour
Instant Book
Stingray powerboat at Simcoe lake
Powerboats in Georgina · 5 guests

Stingray powerboat at Simcoe lake

5.0
$109/hour
25 ft Glastron Powerboat in Innisfil, Ontario
Powerboats in Innisfil · 7 guests

25 ft Glastron Powerboat in Innisfil, Ontario

5.0
$87/hour
16ft Tracker Bass Boat for rent
Fishing in Innisfil · 4 guests

16ft Tracker Bass Boat for rent

New
Snoozed - Active 17 Aug 2025
Monark 17ft Bass fishing boat for rent $250
Fishing in Innisfil · 4 guests

Monark 17ft Bass fishing boat for rent $250

5.0
$188/day
Lake Simcoe Fishing Charter - 18ft Alumacraft Dominator
Fishing in Innisfil · 3 guests

Lake Simcoe Fishing Charter - 18ft Alumacraft Dominator

New
$102/hour
Experience an Unforgettable Party on 34ft Yacht Capacity for 8 Guests
Powerboats in Georgina · 8 guests

Experience an Unforgettable Party on 34ft Yacht Capacity for 8 Guests

5.0
Superowner
$113/hour
2024 19ft Price Craft Pontoon Boat
Powerboats in Georgina · 10 guests

2024 19ft Price Craft Pontoon Boat

5.0
$55+/hour
Fishing/ Cruise Suntracker Pontoon Perfect for a Day on Lake Simcoe!
Powerboats in Georgina · 10 guests

Fishing/ Cruise Suntracker Pontoon Perfect for a Day on Lake Simcoe!

5.0
$55+/hour
18' Sea Swirl Bowrider 90hp Outboard
Powerboats in Huntsville · 8 guests

18' Sea Swirl Bowrider 90hp Outboard

New
$72/hour
22' Ski Ray Tournament 260hp Ski & Wake Boat
Powerboats in Huntsville · 8 guests

22' Ski Ray Tournament 260hp Ski & Wake Boat

New
$95/hour
Ready to Party on 34ft MTX Stylish Motor Yachts in Toronto (8 or 10 people)
Events in Georgina · 8 guests

Ready to Party on 34ft MTX Stylish Motor Yachts in Toronto (8 or 10 people)

5.0
Superowner
$127/hour
Boating on Pigeon Lake - Pleasure- Day/Afternoon/Evening cruises | Fishing
Powerboats in Trent Lakes · 9 guests

Boating on Pigeon Lake - Pleasure- Day/Afternoon/Evening cruises | Fishing

New
$145/hour
Hatteras 43ft Luxury Power Yacht in Pickering, friends and family party!
Events in Pickering · 6 guests

Hatteras 43ft Luxury Power Yacht in Pickering, friends and family party!

New
$182/hour
Private Yacht with Captain, Enjoy with friends and family Beautiful Lake Ontario
Events in Pickering · 6 guests

Private Yacht with Captain, Enjoy with friends and family Beautiful Lake Ontario

5.0
$276/hour
Luxury Regal 1900 Bowrider with Captain
Powerboats in Scarborough · 6 guests

Luxury Regal 1900 Bowrider with Captain

New
$131/hour
Four Winns Vista 258 in Toronto, Ontario
Events in Scarborough · 7 guests

Four Winns Vista 258 in Toronto, Ontario

5.0
$138/hour
Sea Ray 33ft Cruiser in Toronto
Powerboats in Toronto · 8 guests

Sea Ray 33ft Cruiser in Toronto

New
$255/hour

Midland Reviews

  1. Ls

    Lochan

    28' Luxury Charter Serving Lake Simcoe and area

    “My partner and I had such a wonderful time. It was great to be welcomed by such a sweet gesture in the beginning.Captain was so friendly and made sure we were all comfortable and having a good time. It was so much fun to be out on the water and watching the beautiful sunset over the water. Absolutely loved it and will book another boat with Captain next time when we visit . We did our pre wedding shoot on the boat and Captain turned the things so comfortable and easy for us for our shoot. Thanks for your patience and understanding as we reached late to the destination ane Captain was so flexible with the timings. Really apperciate it . Thanks again.

  2. OS

    Olga

    Four Winns Vista 258 in Toronto, Ontario

    We had an absolutely amazing time with this yacht rental — truly a 5-star experience from start to finish! Alvee was warm, professional, and attentive to every detail, making us feel completely relaxed and taken care of throughout the trip. The yacht itself was spotless — perfect for both comfort and style. One of the absolute highlights was watching the sunset from the deck. It was incredibly romantic — the sky lit up with stunning shades of orange, pink, and gold as we gently cruised along the water. It felt like a scene from a movie and was a moment we’ll never forget. Whether you're planning a special occasion or just want to escape for a day, I can’t recommend this yacht rental enough. The views, the service, and especially that sunset made it an experience we’ll treasure forever.

  3. CA

    Cassidy

    Exclusive Getaway for 10 People in Collingwood

    Had the best time with Joe on his boat! We had an absolute blast and couldn’t have asked for a better experience. The vibes were amazing, the music was on point, and the whole day was a solid 10/10. Highly recommend, we’ll definitely be booking with Joe again!

  4. VS

    VIKAS

    Four Winns Vista 258 in Toronto, Ontario

    ALVEE was fantastic! The boat was spotllss, he was super friendly, and made the whole experience enjoyable. I thoroughly enjoyed the ride and would highly recommend him to anyone looking for a great time on the water.

  5. JC

    Jasmeet

    Four Winns Vista 258 in Toronto, Ontario

    we chartered the boat for 2 people and it was a great experience. Alvee was very helpful in guiding us to the parking lot. he was punctual, friendly and a great captain. we would definitely recommend it and return for another trip.

  6. SS

    Sheryl

    Four Winns Vista 258 in Toronto, Ontario

    Not enough words to describe it. Alvee is kind, friendly, and an expert in what he does. He made our time so worthwhile, we are definitely booking again! Don't think twice before booking, you got nothing to worry about:)