Cookies & Agreements

By continuing to use this website, you have read and agree to the Terms of Use and agree to the collection and use of your information by cookies and similar technologies, as set forth in our Privacy Policy.

All listings in Caribbean

Awesome paddleboard rentals in the Caribbean.

5.0
(338 Reviews)

Page 1 of 248 listings

Private San Juan Bay Cruise 37' Sailboat
Sailing in San Juan · 6 guests

Private San Juan Bay Cruise 37' Sailboat

5.0
Superowner
Best of 2026
$195/hour
Lets go boating like a local Sandbar hangout/ Island Hopping/ Paddle-boarding
Powerboats in Key West · 6 guests

Lets go boating like a local Sandbar hangout/ Island Hopping/ Paddle-boarding

4.9
$158+/hour
Explore & Enjoy the Gulf & Back Bay Waters of Bonita on Our 22ft Godfrey Pontoon
Powerboats in Bonita Springs · 12 guests

Explore & Enjoy the Gulf & Back Bay Waters of Bonita on Our 22ft Godfrey Pontoon

5.0
$340+/day
50ft Catamaran Charter with Water Toys -Boca Raton, FL
Sailing in Deerfield Beach · 12 guests

50ft Catamaran Charter with Water Toys -Boca Raton, FL

5.0
$350/hour
The Wanderlust Ultimate Catamaran Adventure
Sailing in Nassau · 12 guests

The Wanderlust Ultimate Catamaran Adventure

5.0
$645/hour
Instant Book
Boston Whaler 24ft Sandbar Hangout Key West
Powerboats in Key West · 6 guests

Boston Whaler 24ft Sandbar Hangout Key West

5.0
$130/hour
Best Value In South East Florida!!!!
Events in Delray Beach · 12 guests

Best Value In South East Florida!!!!

5.0
Superowner
$300/hour
Incredible 45' Sea Ray Sundancer Yacht in Miami Beach!!
Events in Sunny Isles Beach · 13 guests

Incredible 45' Sea Ray Sundancer Yacht in Miami Beach!!

5.0
$160+/hour
Luxury 55' Yacht charter in Nassau Bahamas
Events in Nassau · 12 guests

Luxury 55' Yacht charter in Nassau Bahamas

5.0
$975/hour
3 Islands Tour @Pursuit 2670 Twin '2022 Center Console with Yamaha F250 Engines
Powerboats in San Juan · 6 guests

3 Islands Tour @Pursuit 2670 Twin '2022 Center Console with Yamaha F250 Engines

4.8
$178/hour
LUXURIOUS TIARA 40 EXPRESS
Events in Fajardo · 12 guests

LUXURIOUS TIARA 40 EXPRESS

5.0
$400/hour
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
Fort Lauderdale - Bahamas Sailing Charters
Sailing in Fort Lauderdale · 6 guests

Fort Lauderdale - Bahamas Sailing Charters

5.0
$130+/hour
Private Islamorada Charters in the Florida Keys
Powerboats in Islamorada · 6 guests

Private Islamorada Charters in the Florida Keys

5.0
$135/hour
Private Catamaran Charter - Be Happy 40ft - Discover the beautiful St Maarten
Sailing in Upper Prince's Quarter · 12 guests

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

5.0
$1,750/day
Best Day Ever! Private, All Inclusive & Custom Sailing, Snorkeling, Adventure!
Sailing in St. Thomas · 10 guests

Best Day Ever! Private, All Inclusive & Custom Sailing, Snorkeling, Adventure!

5.0
$225/hour
VIP Experience: 108 Mangusta Luxury Yacht in The Bahamas
Events in Nassau · 12 guests

VIP Experience: 108 Mangusta Luxury Yacht in The Bahamas

5.0
$1,750/hour
Fountaine Pajot 40ft Catamaran! African Dream, Turks and Caicos
Sailing in Leeward Settlement · 10 guests

Fountaine Pajot 40ft Catamaran! African Dream, Turks and Caicos

5.0
$728+/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
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
28 GUESTS - OCEAN VOYAGER 53 CRUISING CATAMARAN
Events in The Valley · 28 guests

28 GUESTS - OCEAN VOYAGER 53 CRUISING CATAMARAN

New
$711/hour
Luxury 33' Sea Ray Sundancer
Events in Aventura · 10 guests

Luxury 33' Sea Ray Sundancer

5.0
$90+/hour
Glide & Discover: SUP Adventure
Adventures in Fajardo · 1 guest

Glide & Discover: SUP Adventure

5.0
$25/hour
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

Paddleboard Reviews in Caribbean

  1. Anna

    Anna

    LUXURIOUS TIARA 40 EXPRESS

    If you have a chance to book a boat day with Miguel, I would definitely recommend! The day was truly one of the highlights of our trip to Puerto Rico. The boat itself was beautiful, spacious, and spotless, and having a bathroom on board made the day even more comfortable. Icacos was the perfect island, crystal-clear water, soft sand, and exactly the relaxing escape we were hoping for. Miguel and his team were absolutely incredible. From the moment we stepped on board, they made sure everyone was taken care of and having a great time. They provided drinks and snacks throughout the day and went above and beyond to create such a fun, easy, and stress-free experience. They also provided tons of floaties and a mat for us to hang in the water and a jet ski! Everything was perfectly organized, the vibes were amazing, and the crew truly made the day unforgettable. I can’t recommend this experience enough, if you’re considering a boat day in Puerto Rico, this is the one to book!

  2. Eric

    Eric

    The Wanderlust Ultimate Catamaran Adventure

    Great day on the boat with David & Z! They were great host who made us feel welcome. We snorkel’d twice where we saw turtles & a reef teaming with fish. If we ever come back we’ll definitely do this again. Our only regret is that we didn’t book an entire day!

  3. Stephen

    Stephen

    Private San Juan Bay Cruise 37' Sailboat

    Luis and Chad were friendly, accommodating and informative as they gave us an amazing ride on the waves.

  4. RM

    Rachel

    The Wanderlust Ultimate Catamaran Adventure

    What a WONDERFUL day we had out on the water on this magnificent beauty of a catamaran. Jim and Dave were the icing on the cake also that made the day so very special and fun. They were both so professional, funny, safety minded, and just plain cool 😎 Our girls had a ball on the front part of the boat doing summersaults on the mesh while the adults lounged :) Later the floating dock and snorkeling were just amazing. We are looking forward to our next trip with this crew. Thanks again to all involved for making it a day we will remember for a long time! ❤️

  5. KN

    Kennedy

    Explore & Enjoy the Gulf & Back Bay Waters of Bonita on Our 22ft Godfrey Pontoon

    Boat was exactly as described- we had a great time with our group! Would definitely rent from Justin again

  6. KR

    Kristy

    Lets go boating like a local Sandbar hangout/ Island Hopping/ Paddle-boarding

    Mike was our captain and was so much fun aboard!! He did a great job of showing us around and was very accommodating. I would highly recommend them to anyone!