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Winter Park, Florida Boat Rentals

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
$47-$113hour
21' Yamaha Jetboat - Cruising & Wake Sports in Orlando
Powerboats in Orlando · 8 guests

21' Yamaha Jetboat - Cruising & Wake Sports in Orlando

5.0
$129-$144hour
Godfrey 20' Pontoon Boat for Rental in Orlando
Powerboats in Orlando · 11 guests

Godfrey 20' Pontoon Boat for Rental in Orlando

5.0
$125hour
2024 Tahoe 2150 OB with 200HP Engine, Fishing Package, and Elevated Comfort
Powerboats in Orlando · 10 guests

2024 Tahoe 2150 OB with 200HP Engine, Fishing Package, and Elevated Comfort

New
$70hour
52' Midnight Lace Luxury Yacht
Events in Orlando · 12 guests

52' Midnight Lace Luxury Yacht

5.0
Superowner
$250hour
2017 Sea Ray SPX 210 Bowrider Charter in Orlando
Powerboats in Orlando · 12 guests

2017 Sea Ray SPX 210 Bowrider Charter in Orlando

5.0
$135hour
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
Flats Fishing Charter with Captain Chris in Orlando, Florida
Fishing in Orlando · 3 guests

Flats Fishing Charter with Captain Chris in Orlando, Florida

New
$94-$125hour
Orlando Jet Ski, Yamaha GP 1.8
Water Sports in Orlando · 3 guests

Orlando Jet Ski, Yamaha GP 1.8

New
$120hour
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
$57-$150hour
259 Splendor Platinum Cuddy Boat on Orlando Lakes!!
Powerboats in Orlando · 6 guests

259 Splendor Platinum Cuddy Boat on Orlando Lakes!!

5.0
$55-$65hour
 Pontoon for rent in Belle Isle, Florida
Powerboats in Belle Isle · 9 guests

Pontoon for rent in Belle Isle, Florida

5.0
$500day
Family Time or Party Time - Sea-Doo Switch Cruise 21
Powerboats in Orlando · 8 guests

Family Time or Party Time - Sea-Doo Switch Cruise 21

New
$85-$150hour
2024 23ft Lowe Tritoon Boat Rental in Windermere, Florida
Powerboats in Windermere · 10 guests

2024 23ft Lowe Tritoon Boat Rental in Windermere, Florida

5.0
$550day
2019 Air Nautique GS22 Surf Boat perfect!
Powerboats in Windermere · 12 guests

2019 Air Nautique GS22 Surf Boat perfect!

5.0
$100hour
Brand New 2024 Yamaha 195s Jetboat - up to 6 passengers
Powerboats in Orlando · 8 guests

Brand New 2024 Yamaha 195s Jetboat - up to 6 passengers

New
$140hour
18ft Maxum for Rent lake butler/Conway
Powerboats in Windermere · 6 guests

18ft Maxum for Rent lake butler/Conway

New
$300day
Brand new 2022 Regal OBX 23' with Comfortable Seating in Orlando
Powerboats in Winter Garden · 8 guests

Brand new 2022 Regal OBX 23' with Comfortable Seating in Orlando

5.0
$90hour
Luxury and elegant REGAL LS2 bowrider in Central FL
Powerboats in Windermere · 6 guests

Luxury and elegant REGAL LS2 bowrider in Central FL

4.9
Superowner
Best of 2023
$50-$127hour
20' Encore Bentley Pontoon for rent in Sanford *FUEL INCLUDED*
Powerboats in Daytona Beach · 8 guests

20' Encore Bentley Pontoon for rent in Sanford *FUEL INCLUDED*

New
$47-$113hour
Axis Surf / Ski / Tube / Wakeboard Boat
Powerboats in Clermont · 11 guests

Axis Surf / Ski / Tube / Wakeboard Boat

5.0
$82hour
Pontoon boat with Captain- Day and Night Cruises, St Cloud FL
Events in Saint Cloud · 20 guests

Pontoon boat with Captain- Day and Night Cruises, St Cloud FL

5.0
$300hour
35' Regal Luxury Day Yacht Rental in St. Cloud, Florida
Events in Saint Cloud · 12 guests

35' Regal Luxury Day Yacht Rental in St. Cloud, Florida

4.9
$495day
Eco Airboat Tour in Kissimmee, Florida
Powerboats in Kissimmee · 10 guests

Eco Airboat Tour in Kissimmee, Florida

5.0
$55hour

Top Destinations Nearby

Winter Park Reviews

  1. MR

    Maria

    Luxury and elegant REGAL LS2 bowrider in Central FL

    Marc was NOTHING SHORT OF AMAZING!! Marc throughly made sure we were comfortable on the boat, he took our pictures, made suggestions along the way for the birthday celebration and my family HAD A BLAST EVERY SINGLE MINUTED! Captain, John also was kind, approachable, made sure we were safe, explained history and fun facts on the water tour. MARC AND JOHN WERE THE PERFECT TEAM!! The boat is clean, roomy, up to date, we blasted our music on the water and the laughs and fun was memorable!! We will be back and will be telling my friends and family to book!! Choosing Marc and Anna's boat, you will NOT be disappointed!!

  2. CC

    Caitlyn

    259 Splendor Platinum Cuddy Boat on Orlando Lakes!!

    Francisco makes the boat renting experience easy and fun! He is so flexible and accommodating. This was the second time I rented from him and I have nothing but positive remarks for both him and the Frale! Definitely would recommend this rental to anyone and everyone! We’ll be coming back at least annually!

  3. SM

    Shay

    Luxury and elegant REGAL LS2 bowrider in Central FL

    Everything was wonderful! Mark was really nice and everything was really smooth, great communication, the boat is beautiful, and we were paired with a great captain(John). I couldn’t have asked for a better time. Thanks Mark and Anna for allowing us to grace your boat!

  4. TM

    Theresa

    2024 23ft Lowe Tritoon Boat Rental in Windermere, Florida

    Great experience! David made everything really easy for use. Boat was beautiful. Weather was perfect. Communication was easy and highly responsive. Will definitely use again.

  5. Makeba

    Makeba

    52' Midnight Lace Luxury Yacht

    This was by far the best boat experience I’ve ever been on. The Captain was extremely knowledgeable and a joy to be around. I had a phenomenal time for my bestfriends birthday. We saw dolphins, mansions, pelicans & the sound system was bomb.com. If your ever in Cocoa Beach…. Look no further! It’s by far the best and largest vessel with the best captain! Oh and the price is better than anyone else’s too!

  6. Ron

    Ron

    2024 23ft Lowe Tritoon Boat Rental in Windermere, Florida

    We had a great time, beautiful boat, and a very easy booking experience. Look forward to booking again on our next trip.