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All listings in Caribbean

Awesome paddleboard rentals in the Caribbean.

5.0
(319 Reviews)

Page 1 of 243 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
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
$349/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
LUXURIOUS TIARA 40 EXPRESS
Events in Fajardo · 12 guests

LUXURIOUS TIARA 40 EXPRESS

5.0
$400/hour
Luxury 55' Yacht charter in Nassau Bahamas
Events in Nassau · 12 guests

Luxury 55' Yacht charter in Nassau Bahamas

5.0
$750/hour
The Wanderlust Ultimate Catamaran Adventure
Sailing in Nassau · 13 guests

The Wanderlust Ultimate Catamaran Adventure

5.0
$632/hour
Instant Book
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
Beautiful Azimut Italian yacht 55’ Flybridge
Events in Dania Beach · 12 guests

Beautiful Azimut Italian yacht 55’ Flybridge

5.0
$290+/hour
Be Happy 40ft - Private Catamaran Charter - Discover the beautiful St Maarten
Sailing in Upper Prince's Quarter · 12 guests

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

5.0
$1,850/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
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
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
Glide & Discover: SUP Adventure
Adventures in Fajardo · 1 guest

Glide & Discover: SUP Adventure

5.0
$25/hour
Sailing catamaran in USVI
Sailing in Charlotte Amalie · 6 guests

Sailing catamaran in USVI

5.0
$1,300/day
Twilight Snorkeling Cruise with Drinks & Gourmet Bites
Powerboats in Fajardo · 6 guests

Twilight Snorkeling Cruise with Drinks & Gourmet Bites

New
$185/hour
Knot at Work 40 - Private Catamaran Charter - Discover the beautiful St Maarten
Sailing in Upper Prince's Quarter · 12 guests

Knot at Work 40 - Private Catamaran Charter - Discover the beautiful St Maarten

New
$1,850/day
48ft Sailing Catamaran | Bubble
Sailing in Miami · 12 guests

48ft Sailing Catamaran | Bubble

New
$423+/hour
BRAND NEW 2025  Lagoon 43 Luxury Catamaran with AC price include 2 guests
Sailing in Guna Yala Comarca · 8 guests

BRAND NEW 2025 Lagoon 43 Luxury Catamaran with AC price include 2 guests

New
$2,200/night
SUP Paddle Board & Snorkel Adventure Tour
Adventures in Saint George Basseterre Parish · 12 guests

SUP Paddle Board & Snorkel Adventure Tour

New
$69/day
Couach 21m Motor Yacht "NEREE" from Marigot, Saint-Martin
Events in Marigot · 12 guests

Couach 21m Motor Yacht "NEREE" from Marigot, Saint-Martin

New
$750/hour

Paddleboard Reviews in Caribbean

  1. JC

    Jose

    Private San Juan Bay Cruise 37' Sailboat

    Captain Luis & Andrea were incredible. My group enjoyed their energy and appreciation and even though we dealt with some rain and gray sky’s, our experience was phenomenal. I would not only recommend Luis, but I would take another trip out with him when I return to PR. We had an exceptional time at sea. Gracias por todo y hasta la próxima.

  2. Josh

    Josh

    Luxury 55' Yacht charter in Nassau Bahamas

    This was my second charter boat experience and my kids first. We could not have been happier! The vessel was exactly at it appeared on the website, the jet ski was amazing (and powerful) our day couldn’t have been much better. The staff made it fun and memorable for all of us. We went snorkeling, swimming with turtles, checked out a remote and private beach that we wouldn’t have been able to experience any other way. To add to experience, we were served out of this world food and beverages. The amazing hospitality we received and unforgettable tasty treats made for a perfect day. My only regret is not booking more time on the vessel with this crew. We booked a 10am - 4pm trip and could have easily done a 9am-6pm or even 7pm. We absolutely loved it!

  3. ER

    Emily

    Best Value In South East Florida!!!!

    Stephen showed us the absolute best time for my bachelorette trip! He was so kind and communicative, let us have the best day! We will definitely come back to see him. I completely recommend if you want an overall fun day!!!!

  4. db

    daniel

    Boston Whaler 24ft Sandbar Hangout Key West

    We had an incredible day out on the water with Captain Anthony! He took us out to Mud Keys and Snipes, and both spots were absolutely stunning. Anthony is a fantastic captain-- professional, knowledgeable about the local waters, and made sure the entire trip felt relaxed and seamless. Whether you're looking for a hidden sandbar to lounge on or want to explore the unique scenery of the keys, he knows exactly where to go to beat the crowds. Ilf you're looking for an authentic and stress-free Key West boat day, we can't recommend Anthony enough. Well definitely be booking with him again next time we're in town!

  5. AZ

    Alex

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

    Would highly recommend working with Justin! We had a great experience. Does a thorough job onboarding you to the nuances of the boat/safety and they’re very well kept/clean. Will definitely be renting a boat from him again in the future!

  6. Robert

    Robert

    Boston Whaler 24ft Sandbar Hangout Key West

    Reservation & pre trip communication with Anthony was easy & straight forward. The boat was perfect and in great shape. Captain Zack was personable, knowledgeable and fun to chill with. we alk enjoyed a fabulous day!!