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Winter Park, Florida Boat Rentals - 2023

4.9(Average of 50,610 reviews in this area)
24 listings
20 ' Bentley Pontoon - Cruise on Lake Maitland *FUEL INCLUDED*
Powerboats in Maitland · 8 guests

20 ' Bentley Pontoon - Cruise on Lake Maitland *FUEL INCLUDED*

5.0
$70hour
Pelican Stand Up Paddle Board on Lake Howell!
Adventures in Casselberry · 1 guest

Pelican Stand Up Paddle Board on Lake Howell!

New
$50day
Hobie Pedal Blue and Orange Kayaks for Rent on Lake Howell
Adventures in Casselberry · 1 guest

Hobie Pedal Blue and Orange Kayaks for Rent on Lake Howell

New
$75day
Yamaha 2020 VX Cruiser HO in Winter Park, FL
Water Sports in Casselberry · 3 guests

Yamaha 2020 VX Cruiser HO in Winter Park, FL

New
$85hour
Tracker Classic XL Bass Boat for Fishing and Scenic Tours in Casselberry
Powerboats in Casselberry · 4 guests

Tracker Classic XL Bass Boat for Fishing and Scenic Tours in Casselberry

New
$300day
Hydra Sport Boat Rental in Orlando, Florida
Powerboats in Orlando · 5 guests

Hydra Sport Boat Rental in Orlando, Florida

New
$100hour
Seadoo Jet Skis for Rent in Orlando
Water Sports in Orlando · 2 guests

Seadoo Jet Skis for Rent in Orlando

New
$100hour
NEW! Rent a Chariot Style Towable Tube in Central Florida | Great with Boats & Jetski!
Adventures in Orlando · 3 guests

NEW! Rent a Chariot Style Towable Tube in Central Florida | Great with Boats & Jetski!

New
$49hour
NEW! Rent the Splash n Chill Island Float in Central Florida | Great for Lakes & Ponds!
Sailing in Orlando · 7 guests

NEW! Rent the Splash n Chill Island Float in Central Florida | Great for Lakes & Ponds!

New
$30hour
Hobie Compass 12ft Pedal Kayak in Orlando, Florida
Adventures in Orlando · 1 guest

Hobie Compass 12ft Pedal Kayak in Orlando, Florida

New
$25hour
Kawasaki Ultra LX 3 seater Delivery option anywhere you want!
Water Sports in Orlando · 3 guests

Kawasaki Ultra LX 3 seater Delivery option anywhere you want!

New
$80hour
52' Midnight Lace Luxury Yacht
Events in Orlando · 12 guests

52' Midnight Lace Luxury Yacht

5.0
Superowner
$250hour
Flats Fishing Charter with Captain Chris in Orlando, Florida
Fishing in Orlando · 3 guests

Flats Fishing Charter with Captain Chris in Orlando, Florida

New
$125hour
2021 Super Air Nautique G23!! Wakesports with Florida's Premier Wakeboat Charter
Powerboats in Orlando · 12 guests

2021 Super Air Nautique G23!! Wakesports with Florida's Premier Wakeboat Charter

5.0
$295hour
Amazing SeaDoo Switch 2022 Tritoon for Rent in Clermont FL
Powerboats in Orlando · 7 guests

Amazing SeaDoo Switch 2022 Tritoon for Rent in Clermont FL

New
$82hour
Neon Drift Seadoo Switch Cruise Boat Rental in Orlando, Florida
Powerboats in Orlando · 7 guests

Neon Drift Seadoo Switch Cruise Boat Rental in Orlando, Florida

New
$82hour
Power in Orlando
Tours in Orlando · 18 guests

Power in Orlando

New
$300hour
Ascend t12 Fishing kayak in Belle Isle, Florida
Adventures in Orlando · 1 guest

Ascend t12 Fishing kayak in Belle Isle, Florida

5.0
$40day
259 Splendor Platinum Cuddy Boat on Orlando Lakes!!
Powerboats in Orlando · 8 guests

259 Splendor Platinum Cuddy Boat on Orlando Lakes!!

5.0
$75hour
20 ' Bentley Pontoon - Cruise on Conway Chain of Lakes *FUEL INCLUDED*
Powerboats in Belle Isle · 8 guests

20 ' Bentley Pontoon - Cruise on Conway Chain of Lakes *FUEL INCLUDED*

5.0
$90hour
2022 Kawasaki Jetski For Rent Up To 68mph Located In Orlando, Florida
Water Sports in Orlando · 3 guests

2022 Kawasaki Jetski For Rent Up To 68mph Located In Orlando, Florida

New
$75hour
Sylvan 20ft Pontoon for rent in Belle Isle, Florida
Powerboats in Belle Isle · 9 guests

Sylvan 20ft Pontoon for rent in Belle Isle, Florida

New
$500day
Rinker captiva 192 Bowrider Rental in Orlando, Florida
Powerboats in Orlando · 8 guests

Rinker captiva 192 Bowrider Rental in Orlando, Florida

New
$400day
SEA DOO Jet Ski Rentals • One or Two Skis Available • Fun Guaranteed! • Chain Of Lakes, Windermere, Florida!
Water Sports in Windermere · 4 guests

SEA DOO Jet Ski Rentals • One or Two Skis Available • Fun Guaranteed! • Chain Of Lakes, Windermere, Florida!

5.0
$75hour

Top Destinations Nearby

Winter Park Reviews

  1. JG
    Jade
    259 Splendor Platinum Cuddy Boat on Orlando Lakes!!

    Great communication. On time and boat was perfect for what we needed. Had a fun time tubing and hanging out. Would definitely book again and recommend

  2. GJ
    Gabrielle
    52' Midnight Lace Luxury Yacht

    Best boat ride ever. We drover from Alabama to ride this boat and it was worth every bit of the ride. The captain was great, made us feel very comfortable and safe. I can’t wait until our next vacation to come back. Nice, clean boat highly recommended.

  3. WB
    Wendy
    52' Midnight Lace Luxury Yacht

    It was the best boat we’ve ever been on. Captain JB and Keith were so helpful with our trip. Recommend that we’d go to the sandbar and we explored a small island. We had so much time and yet it by so quick. The boat was extremely clean and very spacious. We will definitely be booking again soon!

  4. Kayla
    Kayla
    52' Midnight Lace Luxury Yacht

    Our charter with Keith was awesome! He was very knowledgeable about not only his boat but the local area. The boat was beautiful and had plenty of room! Captain Keith gave us the option of where to dock and we landed on a sandbar with a bunch of other boats! Provided our own food and drink, but still had an awesome time! thanks again! Will definitely rebook when im in the area

  5. KM
    Kincaid
    2021 Super Air Nautique G23!! Wakesports with Florida's Premier Wakeboat Charter

    This was my first time booking a boat cruise especially out of state with the amount of people I had. It honestly exceeded my expectations from the communication, location, and comfortability on the boat. Mike and Ashton were awesome and kept my group entertained - I'd book again if I'm in the area.

  6. CP
    Chad
    259 Splendor Platinum Cuddy Boat on Orlando Lakes!!

    Wow !!! What an amazing time we had !!! From start to end. We inquired about the boat the morning of and Fransisco was super responsive and was waiting for us at the dock with less then 2 hour notice. He's boat is gorgeous and he explained everything before we sailed and made sure to even drop a pin on our maps on the phone. Will definitely be back on our next trip to Florida !!!