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Winter Haven, Florida Boat Rentals & Yacht Charters

Page 1 of 124 listings

Luxury MasterCraft Cruise with Captain
Powerboats in Winter Haven · 12 guests

Luxury MasterCraft Cruise with Captain

New
$120/hour
24’ Hurricane deck boat for 12 person
Powerboats in Winter Haven · 12 guests

24’ Hurricane deck boat for 12 person

5.0
$80/hour
23’ Hurricane Deck Boat
Powerboats in Winter Haven · 12 guests

23’ Hurricane Deck Boat

5.0
$80/hour
Sweetwater 22ft Pontoon in Lake Wales
Powerboats in Florida · 8 guests

Sweetwater 22ft Pontoon in Lake Wales

New
$450/day
Great Bentley 24ft Pontoon Rental in Lake Wales, Florida
Powerboats in Florida · 8 guests

Great Bentley 24ft Pontoon Rental in Lake Wales, Florida

New
$450/day
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
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

5.0
$67/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
St. Pete & Anna Maria Boat Rentals – Fishing & Family Fun
Powerboats in Saint Cloud · 8 guests

St. Pete & Anna Maria Boat Rentals – Fishing & Family Fun

5.0
$80+/hour
40' Regal Luxury Yacht Rental In St. Cloud
Events in Saint Cloud · 12 guests

40' Regal Luxury Yacht Rental In St. Cloud

5.0
$174/hour
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
Inflatable Boat with Aluminum Floor in St. Cloud, Florida
Fishing in Saint Cloud · 4 guests

Inflatable Boat with Aluminum Floor in St. Cloud, Florida

5.0
$75/day
2023 Yamaha AR250 - Like New
Powerboats in Windermere · 12 guests

2023 Yamaha AR250 - Like New

5.0
$150/hour
22' Sweetwater Party Barge Pontoon - Seats up to 12
Powerboats in Clermont · 12 guests

22' Sweetwater Party Barge Pontoon - Seats up to 12

New
$65+/hour
2017 Sea Ray SPX 210 Bowrider in Orlando, Florida
Powerboats in Orlando · 10 guests

2017 Sea Ray SPX 210 Bowrider in Orlando, Florida

5.0
$175/hour
Experience the Thrill on a 22' Yamaha Jetboat in Tampa Bay, Florida
Powerboats in Riverview · 10 guests

Experience the Thrill on a 22' Yamaha Jetboat in Tampa Bay, Florida

5.0
$75+/hour
2025 Tahoe Bowrider - Captained Charters from Riverview Marina, FL
Powerboats in Riverview · 8 guests

2025 Tahoe Bowrider - Captained Charters from Riverview Marina, FL

New
$125/hour
Bentley Pontoon-Double Bimini Boat for Rent in Riverview
Powerboats in Riverview · 13 guests

Bentley Pontoon-Double Bimini Boat for Rent in Riverview

New
$400/day
2023 Sundance B20CCR – Family Fun, Fishing, & Beach Adventures!
Fishing in Orlando · 6 guests

2023 Sundance B20CCR – Family Fun, Fishing, & Beach Adventures!

5.0
$70+/hour
Godfrey 20ft Pontoon for Boat Day in Central Florida – Easy Booking
Powerboats in Orlando · 8 guests

Godfrey 20ft Pontoon for Boat Day in Central Florida – Easy Booking

New
$90/hour
2024 Yamaha 195s Jetboat - up to 7 passengers
Powerboats in Orlando · 7 guests

2024 Yamaha 195s Jetboat - up to 7 passengers

5.0
$120+/hour
2021 A20 Surf & Wake Boat-Come Board in Florida's Premier Weather, Year Round!
Powerboats in Ocoee · 8 guests

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

5.0
$100/hour
25' Tidewater Center Console for rent in Orlando
Powerboats in Orlando · 6 guests

25' Tidewater Center Console for rent in Orlando

New
$100/hour
26' Party Deck Boat - Loud Sound System, Comfy Seats, Up to 12 Guests
Powerboats in Tampa · 12 guests

26' Party Deck Boat - Loud Sound System, Comfy Seats, Up to 12 Guests

New
$120+/hour

Winter Haven Reviews

  1. CW

    Cassidy

    40' Regal Luxury Yacht Rental In St. Cloud

    Everything was perfect. They already had places we could go to see things and to just hang out. It was so relaxing and fun at the same time. Owner of the boat is excellent at communication and overall just a super fun guy.

  2. Kate

    Kate

    2024 Yamaha 195s Jetboat - up to 7 passengers

    Ricardo was incredibly attentive, responsive, and ensured a safe operation throughout the entire experience. His professionalism and communication made everything easy. I will absolutely be booking with him again in the future.

  3. DR

    Dominic

    2024 Yamaha 195s Jetboat - up to 7 passengers

    This was by far the best experience my family has had since we started coming to Florida every year for spring break. Ricardo went above and beyond to make sure we got the full experience. My family is terrified of the water and they all got on the tube so that speaks volume of his professionalism . I highly recommend adding the jetski to your rental. Definitely a 10/10 experience!

  4. SH

    Steven

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

    Avery was fantastic to work with. We rented his bass boat for fishing on Lake Toho in Kissimmee, and the entire experience exceeded expectations. The boat performed flawlessly and was clearly well-maintained, with great upgrades like shallow water anchors and top-notch electronics that made a big difference on the water. Over the course of three days, we caught around 30 bass—and honestly, we weren’t even fishing that hard. Once the sun got hot, we’d call it a day and still had incredible success. More importantly, it gave our family the chance to make some lifelong memories together. Avery delivered on everything he promised, and then some. I wouldn’t hesitate to rent from him again the next time we’re in the area. Highly recommend.

  5. BM

    Bailey

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

    Kevin was so amazing! The water was perfect and he was so patient with us and our experience!

  6. EL

    Eli

    2024 Yamaha 195s Jetboat - up to 7 passengers

    Ricardo’s add, pricing, services and communication deserve a 7 star rating along with the planning punctionality, care and personalized experience while service. Ricardo covers all the areas and knows the lake very well. Our party loved the experience and we will return for more!!