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All listings in Caribbean

Amazing wakeboarding rentals in the Caribbean.

4.8
(271 Reviews)

Page 1 of 232 listings

Captained Nautique Wake Sports Boat - Complete Equipment Included - Miami
Powerboats in Coral Gables · 6 guests

Captained Nautique Wake Sports Boat - Complete Equipment Included - Miami

5.0
$275hour
Captain included, Sandbar hangout, Backcountry, SunSet Cruise, Water-sports
Powerboats in Key West · 6 guests

Captain included, Sandbar hangout, Backcountry, SunSet Cruise, Water-sports

5.0
$141hour
2022 Yamaha 252XE in Key largo, FL
Powerboats in Key Largo · 10 guests

2022 Yamaha 252XE in Key largo, FL

5.0
$125hour
2023 Yamaha Jetboat: Make Waves, Create Memories, Have Fun!
Water Sports in North Bay Village · 8 guests

2023 Yamaha Jetboat: Make Waves, Create Memories, Have Fun!

New
$150hour
26' Monterey M5 Ski Boat for Boat Cruise and Watersports
Powerboats in Miami · 12 guests

26' Monterey M5 Ski Boat for Boat Cruise and Watersports

4.9
$120hour
Unleash Fun: 2023 Yamaha AR220 for Small Groups – All-Inclusive
Powerboats in Miami · 8 guests

Unleash Fun: 2023 Yamaha AR220 for Small Groups – All-Inclusive

5.0
$100hour
Cruise and Party in Style! 26' Luxurious Ski Boat! Price don't include fuel.
Powerboats in Miami · 12 guests

Cruise and Party in Style! 26' Luxurious Ski Boat! Price don't include fuel.

5.0
$125hour
Amazing Punta Cana Sand Bar Party with Chaparral Motor Yacht!
Events in Bávaro · 150 guests

Amazing Punta Cana Sand Bar Party with Chaparral Motor Yacht!

5.0
$45hour
Fully Customizable Half Day PRIVATE Charter
Powerboats in Leeward Settlement · 10 guests

Fully Customizable Half Day PRIVATE Charter

5.0
$250hour
Wake Surf Wake Skate In Key West, Florida
Tours in Key West · 6 guests

Wake Surf Wake Skate In Key West, Florida

5.0
Snoozed - Active 02 Jan 2025
27' Yamaha 2021 Super Powerboat In Miami Beach, Florida!
Powerboats in Miami · 10 guests

27' Yamaha 2021 Super Powerboat In Miami Beach, Florida!

4.0
Best of 2023
$100hour
24’ Yamaha 242 Limited S Jet Boat! Captained - Wakeboard Kit!
Powerboats in Miami · 6 guests

24’ Yamaha 242 Limited S Jet Boat! Captained - Wakeboard Kit!

5.0
$400hour
Wakesurf - Wakeboard - Tube - Ski -Slalom
Powerboats in Sunny Isles Beach · 6 guests

Wakesurf - Wakeboard - Tube - Ski -Slalom

5.0
$220hour
2022 Yamaha 252XE Powerboat in Marco Island, FL
Powerboats in Marco Island · 10 guests

2022 Yamaha 252XE Powerboat in Marco Island, FL

New
$140hour
BOAT RENTAL - Boynton or Delray, FL  Rental As Low as $125hr
Powerboats in Boca Raton · 10 guests

BOAT RENTAL - Boynton or Delray, FL Rental As Low as $125hr

5.0
$150hour
Stingray 21ft Bowrider Wakeboarding Session in Miami Beach, Florida
Powerboats in Miami Beach · 6 guests

Stingray 21ft Bowrider Wakeboarding Session in Miami Beach, Florida

3.0
$185hour
90/h for the boat and captain and fuel is extra in the final price
Powerboats in Miami · 8 guests

90/h for the boat and captain and fuel is extra in the final price

New
$90hour
Parasailing in Trelawny Parish
Adventures in Montego Bay · 8 guests

Parasailing in Trelawny Parish

New
$165person
4-Pack All Boards Watersports Combo in Montego Bay
Adventures in Montego Bay · 8 guests

4-Pack All Boards Watersports Combo in Montego Bay

New
$384person
The Miami Wakesurf Experience with Malibu 26LSV Bowrider!
Powerboats in Miami Beach · 6 guests

The Miami Wakesurf Experience with Malibu 26LSV Bowrider!

New
$330-$360hour
Cruise and Sandbar on Amazing Axis A24 Wakeboat in Miami
Powerboats in Miami Beach · 6 guests

Cruise and Sandbar on Amazing Axis A24 Wakeboat in Miami

New
$280hour
Surf Lessons In Punta Cana
Adventures in Macao · 1 guest

Surf Lessons In Punta Cana

New
$95person
🌴 Watersports boat perfect for the family 🌴
Powerboats in Delray Beach · 8 guests

🌴 Watersports boat perfect for the family 🌴

New
$190-$215hour
Ride The Adventurous Waves In Chocó, Colombia!
Adventures in Antioquia · 1 guest

Ride The Adventurous Waves In Chocó, Colombia!

New
$690person

Wakeboarding Reviews in Caribbean

  1. kayla

    kayla

    26' Monterey M5 Ski Boat for Boat Cruise and Watersports

    David was a fantastic captain! Very friendly and knows his stuff! He was extremely helpful with us wakeboarding. If you have never done wakeboarding before but want to try, he is the captain to book! We went to a great spot that has a beautiful Miami view behind us which was fun to see while surfing. He keeps his boat extremely clean and tidy which shows how much he’s cares! We even got to see a few dolphin while we were out! Boat had plenty of space and seats surprised me with how comfy they were! Great sound system. All around a 10/10. You must book with David!

  2. Itzhak

    Itzhak

    26' Monterey M5 Ski Boat for Boat Cruise and Watersports

    We had an awesome experience amazing captain. Highly recommend

  3. Holly

    Holly

    Captain included, Sandbar hangout, Backcountry, SunSet Cruise, Water-sports

    Anthony called us ahead of time to warn of the wind and asked if we wanted to reschedule. Due to our travel plans, we decided not to, but still had a wonderful time! Anthony was knowledgeable, friendly and knew what he was doing! We would recommend him.

  4. LA

    Laura

    Captain included, Sandbar hangout, Backcountry, SunSet Cruise, Water-sports

    We all enjoyed the hole trip, it was our last day in key west and we couldn’t have asked for a better way to finish our trip to key west. We all felt save with Anthony as a captain, he told us a lot about the island as we sailed around. The biggest recommendation from us if you are looking for something to top your vacation

  5. Michele

    Michele

    Captain included, Sandbar hangout, Backcountry, SunSet Cruise, Water-sports

    Stop looking! THIS is your boat/captain experience. I researched the heck out of what boat to hire for our trip to Key West. And we saw a ton of other boats/captains on our sandbar sunset trip…this is the best boat and Anthony was by far the most warm, service oriented, and knowledgeable captain. And his little pug, Mystic, absolutely made the trip feel like we were on our own boat. We will be back and will use Anthony every time.

  6. AE

    ALISA

    Captain included, Sandbar hangout, Backcountry, SunSet Cruise, Water-sports

    We hired Anthony for a 4 hour boat cruise and had an absolute blast. The boat (a 23' Boston Whaler) was very comfortable to ride and also provided shade when it got too hot. Anthony took us to sand bars, shared his knowledge of the Keys and even procured a 12 pack for us from a party boat when we ran out (a rookie mistake indeed!). Anthony is a very competent captain and I felt safe the entire time. We've hired several boats with captains before and Anthony is the best one by far. The bonus was he brought his 20 lb pug, Mystic, who is soooo sweet and always well-behaved. What a day!! Thank you so much, Anthony!!