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All listings in Caribbean

Awesome paddleboard rentals in the Caribbean.

5.0
(277 Reviews)

Page 1 of 236 listings

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
Limited Availability
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
Boston Whaler 24ft Sandbar Hangout Key West
Powerboats in Key West · 6 guests

Boston Whaler 24ft Sandbar Hangout Key West

5.0
$130/hour
High Demand
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
$450/hour
The Wanderlust Ultimate Catamaran Adventure
Sailing in Nassau · 12 guests

The Wanderlust Ultimate Catamaran Adventure

5.0
$637/hour
Best Value In South East Florida!!!!
Events in Delray Beach · 12 guests

Best Value In South East Florida!!!!

5.0
Superowner
$349/hour
Luxury 55' Yacht charter in Nassau Bahamas
Events in Nassau · 12 guests

Luxury 55' Yacht charter in Nassau Bahamas

5.0
$750/hour
High Demand
LUXURIOUS TIARA 40 EXPRESS
Events in Fajardo · 12 guests

LUXURIOUS TIARA 40 EXPRESS

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

Fort Lauderdale - Bahamas Sailing Charters

5.0
$130+/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
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
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
Caribbean · 12 guests

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

5.0
$1,850/day
Limited Availability
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
$115+/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
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
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
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
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
$2,600/night
Miami Catamaran Charter | 48ft Sailing Yacht ⚓🌊
Sailing in Miami · 12 guests

Miami Catamaran Charter | 48ft Sailing Yacht ⚓🌊

New
$426+/hour
Couach 21m Motor Yacht "NEREE" from Marigot, Saint-Martin
Events in Saint Martin · 12 guests

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

New
$757/hour
SUP Paddle Board & Snorkel Adventure Tour
Adventures in Saint George Basseterre Parish · 12 guests

SUP Paddle Board & Snorkel Adventure Tour

New
$69/day
Don't Worry 45 - Luxury Private Charter - St Maarten or Anguilla
Caribbean · 16 guests

Don't Worry 45 - Luxury Private Charter - St Maarten or Anguilla

New
$2,350/day

Paddleboard Reviews in Caribbean

  1. EJ

    Ed

    Private San Juan Bay Cruise 37' Sailboat

    A beautiful sunset cruise with my family. Wind was amazing on the bay and there was a bright moon and amazing breeze when we sailed back. Captain Luis and his deckhand Gabby were filled with information about Puerto Rico and the history. Highly recommended!

  2. JL

    James

    Private San Juan Bay Cruise 37' Sailboat

    We took a private boat tour with Captain Luis and Gaby, and it was hands-down one of the best parts of our vacation. From the moment we arrived, we were greeted warmly and walked right over to the boat, which was the perfect size for our group of friends to relax and spread out. Captain Luis is an incredible captain—he navigated the waters with total ease, took us to gorgeous spots all over, and shared fascinating tidbits about Puerto Rico along the way. Both he and Gaby kept the vibes immaculate, sharing delicious sangria and making sure we had everything we needed. We spent the day listening to our favorite music, swimming, enjoying some snacks, and soaking up the sun. If you are looking for a top-tier, stress-free day on the water, I cannot recommend Captain Luis and Gaby enough! We’d book them again in a heartbeat.

  3. GV

    Grace

    Luxury 55' Yacht charter in Nassau Bahamas

    We had such a great experience on this boat trip. The staff truly made it—they were incredibly accommodating, quick to help with anything we needed, and just so easy to be around. From the moment we arrived, everything felt seamless and well-organized. They made sure we were comfortable, had everything we needed, and kept the day running smoothly. You can tell they genuinely care about their guests having a good time. The whole experience felt relaxed but still very professional. It was exactly the kind of day we were hoping for. Would absolutely book with them again.

  4. EM

    Erin

    LUXURIOUS TIARA 40 EXPRESS

    Fantastic experience with Captain Miguel! Super friendly, professional, and made the trip so enjoyable. Beautiful boat and an unforgettable day. Highly recommend!

  5. WD

    Whit

    Boston Whaler 24ft Sandbar Hangout Key West

    Anthony was a great captain and guide for our 4 hour trip, going out of his way to find us some unique spots in the sandbars. Would definitely recommend Anthony to anyone else looking for a relaxed tour around the area.

  6. 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.