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All listings in Caribbean

Awesome kayak rentals in the Caribbean.

4.8
(1,166 Reviews)

Page 2 of 6133 listings

41ft Metta Sailing Catamaran in Turks and Caicos Islands
Sailing in Leeward Settlement · 12 guests

41ft Metta Sailing Catamaran in Turks and Caicos Islands

5.0
$450/hour
Custom Private Bioluminescence Kayak Tour in Fajardo
Adventures in Fajardo · 18 guests

Custom Private Bioluminescence Kayak Tour in Fajardo

2.3
Superowner
$99/day
Fort Lauderdale - Bahamas Sailing Charters
Sailing in Fort Lauderdale · 6 guests

Fort Lauderdale - Bahamas Sailing Charters

5.0
$130+/hour
VanDutch 55 Motor Yacht Charter Anguilla | St Barths | St Martin
Events in Crocus Hill · 15 guests

VanDutch 55 Motor Yacht Charter Anguilla | St Barths | St Martin

5.0
$850/hour
Private Motor Boat Excursion - 8 persons - Axopar 29 ft with captain
Powerboats in Saint Martin · 8 guests

Private Motor Boat Excursion - 8 persons - Axopar 29 ft with captain

5.0
$160+/hour
Sleek & Stylish 23ft SeaRay: Your Dream Cruiser Awaits!
Powerboats in Boynton Beach · 8 guests

Sleek & Stylish 23ft SeaRay: Your Dream Cruiser Awaits!

5.0
$85+/hour
Luxury Catamaran Punta Cana
Events in La Romana · 150 guests

Luxury Catamaran Punta Cana

5.0
Superowner
Best of 2026
$70/hour
Ocean Paddle Adventure: Kayak Rental
Adventures in Fajardo · 2 guests

Ocean Paddle Adventure: Kayak Rental

5.0
$50/hour
Cap Cana Private yacht sandbar & snorkel - Cap Cana, Punta Cana
Powerboats in Punta Cana · 18 guests

Cap Cana Private yacht sandbar & snorkel - Cap Cana, Punta Cana

4.6
Superowner
$190/hour
Limited Availability
Beautiful Azimut Italian yacht 55’ Flybridge
Events in Dania Beach · 12 guests

Beautiful Azimut Italian yacht 55’ Flybridge

5.0
$290+/hour
Sea-Doo GTR 230 Supercharged Jet Ski Rental in Miami, Florida
Water Sports in Hallandale Beach · 3 guests

Sea-Doo GTR 230 Supercharged Jet Ski Rental in Miami, Florida

5.0
$110+/hour
Be Happy 40ft - Private Catamaran Charter - Discover the beautiful St Maarten
Caribbean · 12 guests

Be Happy 40ft - Private Catamaran Charter - Discover the beautiful St Maarten

5.0
$1,850/day
VanDutch 55 Motor Yacht Charter St Barths | Anguilla | St Martin
Events in Gustavia · 12 guests

VanDutch 55 Motor Yacht Charter St Barths | Anguilla | St Martin

5.0
$900/hour
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
$400/hour
Private Islamorada Charters in the Florida Keys aboard 23' Hurricane Fun Deck
Powerboats in Islamorada · 6 guests

Private Islamorada Charters in the Florida Keys aboard 23' Hurricane Fun Deck

5.0
$135/hour
AFFORDABLE 27 ft SEA RAY SUNDECK 270 IN FORT LAUDERDALE
Events in Fort Lauderdale · 12 guests

AFFORDABLE 27 ft SEA RAY SUNDECK 270 IN FORT LAUDERDALE

5.0
$185+/hour
45' Lagoon Sailing Catamaran in St. Thomas, U.S. Virgin Islands
Sailing in St. Thomas · 12 guests

45' Lagoon Sailing Catamaran in St. Thomas, U.S. Virgin Islands

5.0
$2,000/day
72'/22M Mangusta Available Now In Nassau, Bahamas
Events in Nassau · 13 guests

72'/22M Mangusta Available Now In Nassau, Bahamas

5.0
$810+/hour
Proline 30ft Cuddy Cabin for Miami Biscayne Bay Cruising
Tours in Miami · 5 guests

Proline 30ft Cuddy Cabin for Miami Biscayne Bay Cruising

New
$88/hour
55' Azimut Flybridge II 2020
Events in Miami Beach · 13 guests

55' Azimut Flybridge II 2020

5.0
Superowner
$200/hour
Super Fun Deck Boat Captain included
Powerboats in Islamorada · 6 guests

Super Fun Deck Boat Captain included

5.0
$85/hour
Guided Clear Kayak /Paddle Board Tours and Rentals
Adventures in Leeward Settlement · 8 guests

Guided Clear Kayak /Paddle Board Tours and Rentals

New
$115/hour
EXPERIENCE MIAMI IN STYLE - 40FT CRUISER 🛥️🌴
Events in Miami · 12 guests

EXPERIENCE MIAMI IN STYLE - 40FT CRUISER 🛥️🌴

New
Superowner
$75/hour
1 Hour Reef Snorkeling Trip in the Sandy Reefs in Negril Sea, Jamaica
Tours in West End · 12 guests

1 Hour Reef Snorkeling Trip in the Sandy Reefs in Negril Sea, Jamaica

5.0
$240/hour

Kayak Reviews in Caribbean

  1. TW

    Terry

    41ft Metta Sailing Catamaran in Turks and Caicos Islands

    A perfect day on the Metta. After messaging about our grandkids interests, the captain took us to the boat wreck to snorkel and then to a great coral reef! Snacks, drinks and gear were provided and they were very helpful. Last, we swam and played on the most beautiful beach and the kids saw iguanas! Great hosts! We will book the Metta again!

  2. KH

    Kanisha

    41ft Metta Sailing Catamaran in Turks and Caicos Islands

    We had an amazing time with our group of 8 adults and 3 kids under 5. We had a totally customized itinerary and the crew is so incredibly helpful and welcoming. We had an amazing time on a half day charter and would definitely do a full day with this crew any time. The highlight of our trip was JoJo the dolphin following us during the whole charter! We got to snorkel with him and the kids were so happy to see him following alongside the boat the whole way!

  3. LE

    Lia

    Fort Lauderdale - Bahamas Sailing Charters

    Truly incredible experience with Jose and Alex. Absolutely magical adventure and highly recommended to anyone looking for an unforgettable time. The food was also out of this world and so much attention to detail in every moment. We will absolutely be back and everyone needs to experience this.

  4. Sofia

    Sofia

    Fort Lauderdale - Bahamas Sailing Charters

    Wow, this was an incredible experience for a very reasonable price. Jose and Alexandria’s hospitality and generosity is unmatched. I left the boat with two new friends, and I will definitely be keeping their information for future trips. We did a trip around Fort Lauderdale, and we were lucky enough to see some dolphins! We swam around in the beautiful and refreshing water and we had some incredible snacks, wellness drinks, and a meal at the end. All very healthy, and we left the boat feeling much better than we did when we got on. That’s the power of high quality, healthy food. Everything about this trip was amazing, but I must say the best part was their kindness. They took great care of me and my friends. Wonderful people and a very impressive boat!

  5. AH

    Andrew

    Fort Lauderdale - Bahamas Sailing Charters

    I cannot overstate how wonderful our afternoon sail was with Jose and Luke. The weather was perfect, the boat in correct order, and each phase of the experience was conducted seamlessly. With that said, the calming center of the day - and by far the main reason we had such a special time -was Jose. Every once in a while, you meet a special person who has mastered their craft, acts as an enthusiastic and patient instructor, while making sure each person was comfortable and happy. For some, sailing can be intimidating, especially when the wind and waves act up. Jose was 'present' every moment to show us the joys of switching from power to wind, with confidence and professionalism. While we have charted powerboats and sailboats, this particular experience is not to be missed. He even prepared us healthy, vegan food once we returned to dock, showing us being in nature, enjoying the sea, and having yummy healthy food is all part of finding some momentary tranquility. Book this experience! I know we will again.

  6. William

    William

    Fort Lauderdale - Bahamas Sailing Charters

    Awesome and experienced Captain, Jose, who was a pleasure to spend time with. Great communication, very flexible to accommodate my individual aims for the sailing experience. Exceedingly accommodating to spend time on a special request to focus of our time on navigating dockage. His coaching made a big difference for me! 5 stars all the way!