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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
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
Sweetwater 22ft Pontoon in Lake Wales
Powerboats in Florida · 8 guests

Sweetwater 22ft Pontoon in Lake Wales

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
Sun, Lakes & Vibes – Captained Robalo 160 Center Console in Chicago
Powerboats in Windermere · 3 guests

Sun, Lakes & Vibes – Captained Robalo 160 Center Console in Chicago

New
$64/hour
24 foot Sweetwater Pontoon - Seats up to 12
Powerboats in Clermont · 12 guests

24 foot Sweetwater Pontoon - Seats up to 12

New
$63+/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
2023 Kawasaki STX 160X Jet Ski Rental for Family Fun in Riverview, Florida
Water Sports in Riverview · 3 guests

2023 Kawasaki STX 160X Jet Ski Rental for Family Fun in Riverview, Florida

New
$60/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
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

Winter Haven Reviews

  1. JM

    Johnny

    24’ Hurricane deck boat for 12 person

    Renting JT's Hurricane boat was the right choice. My family and friends (8 of us) had a great time. JT was on time, with the boat in th water, full tank of gas, included a cooler with 2 bags of ice! He also let us use his tube to pull the kids around. Excellent 4th of July experience. Highly recommend.

  2. EC

    Eric

    2024 Yamaha 195s Jetboat - up to 7 passengers

    Ricardo went above and beyond to make it a great day even though we had to deal with thunderstorms and rain. We went to different lakes through channels trying to find less rain and clearer skies in the scattered Florida storms. And we did. We had a great time tubing in the warm water despite not having a lot of sunshine. Most of the other Orlando attractions were weather delayed but Ricardo was all systems go. Highly recommend.

  3. DJ

    Daria

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

    Kevin was amazing! My friends and I have never waterboarded or tubed before and he made the experience so comfortable and pleasant. My friend had a great time and appreciated his hospitality. If we are in town again then we will definitely book with Kevin.

  4. 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.

  5. 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.

  6. Jessica

    Jessica

    24’ Hurricane deck boat for 12 person

    We had an incredible time out on the water with JT! Our entire family had an absolute blast — from start to finish, it was fun, safe, and unforgettable. The boat was in great condition, the vibes were relaxed and upbeat, and JT made sure everyone felt comfortable, whether we were cruising or trying something new. Highly recommend booking a trip if you’re in the area!🚤🌊