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Winter Garden, Florida Boat Rentals

Page 1 of 124 listings

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
$90/hour
2021 A20 Surf & Wake Boat-Come Board in Florida's Premier Weather, Year Round!
Powerboats in Ocoee · 6 guests

2021 A20 Surf & Wake Boat-Come Board in Florida's Premier Weather, Year Round!

5.0
$100/hour
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
$550/day
2019 Air Nautique GS22 Surf Boat perfect!
Powerboats in Windermere · 12 guests

2019 Air Nautique GS22 Surf Boat perfect!

5.0
$100/hour
Sea Born FX24 Center Console Boat Rental in Windermere, Florida
Powerboats in Windermere · 5 guests

Sea Born FX24 Center Console Boat Rental in Windermere, Florida

New
$100/hour
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 2025
$59+/hour
2023 Yamaha beautiful 22 ft California Jet Boat - up to 10 people or 1600 lbs.
Powerboats in Orlando · 10 guests

2023 Yamaha beautiful 22 ft California Jet Boat - up to 10 people or 1600 lbs.

New
$150/hour
Godfrey 20' Pontoon Boat for Rental in Orlando
Powerboats in Orlando · 11 guests

Godfrey 20' Pontoon Boat for Rental in Orlando

5.0
$125/hour
21' Yamaha Jetboat - Cruising & Wake Sports in Orlando
Powerboats in Orlando · 8 guests

21' Yamaha Jetboat - Cruising & Wake Sports in Orlando

5.0
$129+/hour
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
$295/hour
52' Midnight Lace Luxury Yacht
Events in Orlando · 12 guests

52' Midnight Lace Luxury Yacht

5.0
Superowner
$250/hour
2017 Sea Ray SPX 210 Bowrider
Powerboats in Orlando · 10 guests

2017 Sea Ray SPX 210 Bowrider

5.0
$175/hour
WATER SPORTS WAKE BOAT!!!
Powerboats in Winter Park · 12 guests

WATER SPORTS WAKE BOAT!!!

New
$175/hour
259 Splendor Platinum Cuddy Boat on Orlando Lakes!!
Powerboats in Orlando · 6 guests

259 Splendor Platinum Cuddy Boat on Orlando Lakes!!

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

Pontoon for rent in Belle Isle, Florida

5.0
$500/day
Brand New 2024 Yamaha 195s Jetboat - up to 7 passengers
Powerboats in Orlando · 8 guests

Brand New 2024 Yamaha 195s Jetboat - up to 7 passengers

5.0
$110+/hour
24’ Tidewater Bay Boat - up to 8 people - Captained Trips Available
Powerboats in Tavares · 8 guests

24’ Tidewater Bay Boat - up to 8 people - Captained Trips Available

New
$125/hour
Eco Airboat Tour in Kissimmee, Florida
Powerboats in Kissimmee · 10 guests

Eco Airboat Tour in Kissimmee, Florida

5.0
$55/hour
Bass Fishing Boat in St.Cloud on Big Lake Toho - 2025 Ranger Z520R
Fishing in Saint Cloud · 4 guests

Bass Fishing Boat in St.Cloud on Big Lake Toho - 2025 Ranger Z520R

New
$67/hour
Bass Fishing Boat in St. Cloud on Big Lake Toho
Fishing in Kissimmee · 4 guests

Bass Fishing Boat in St. Cloud on Big Lake Toho

4.9
$50/hour
Sea ray sundancer 240 with room and a/c
Powerboats in Davenport · 10 guests

Sea ray sundancer 240 with room and a/c

New
$120/hour
2018 Yamaha 242 Charter Kissimmee,Clearwater,silver glen.
Powerboats in Saint Cloud · 10 guests

2018 Yamaha 242 Charter Kissimmee,Clearwater,silver glen.

New
$115+/hour
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
$495/day
34' Bayliner Day Motor Yacht for 12 person
Events in Saint Cloud · 12 guests

34' Bayliner Day Motor Yacht for 12 person

5.0
$174+/hour

Winter Garden Reviews

  1. MW

    Mike

    Bass Fishing Boat in St. Cloud on Big Lake Toho

    I highly recommend Avery to everyone that is in need of a vessel to do your fishing while on vacation. Avery was very accommodating, flexible, and the absolute best host for my fishing experience. He was very responsive and communicated well with me on every occasion he was needed. I will definitely be a retuning customer on future vacations.

  2. Alex

    Alex

    2021 A20 Surf & Wake Boat-Come Board in Florida's Premier Weather, Year Round!

    Great experience. Boat was gassed up and ready to go upon arrival. Boat is in great condition and everything worked well. We will definitely go on this boat again! Perfect for wakeboarding and surfing. Throws a massive wake. Super nice interior. Couldn’t ask for more. Everyone had a great time.

  3. SD

    Shlomy

    Brand New 2024 Yamaha 195s Jetboat - up to 7 passengers

    We had an unforgettable day out on the water! The speedboat trip was exhilarating from start to finish, with breathtaking views and plenty of thrilling moments. The highlight was definitely the tubing—so much fun! Our captain Ricardo was super friendly and made sure we all felt safe while still getting that adrenaline rush. The entire experience was well-organized, and the atmosphere was amazing. Whether you’re a thrill-seeker or just want to relax and enjoy the ride, this trip is perfect. Highly recommend for anyone looking for an adventure!

  4. Sf

    Safy

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

    I had a killer birthday party here and was even able to rent out another one of Avery’s yachts and sail together. Everyone had a blast.

  5. Adam

    Adam

    Luxury and elegant REGAL LS2 bowrider in Central FL

    Had a great time on Mark and Anna's boat - can't recommend John T highly enough as a captain. We had a family of 5 with young kids and they all had a blast tubing. Mark and Anna were very gracious hosts, offering flexibility as a result of iffy weather the day of our trip. Thank you for a great memory!

  6. 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!!