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All listings in Caribbean

Awesome paddleboard rentals in the Caribbean.

5.0
(344 Reviews)

Page 1 of 244 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
Boston Whaler 24ft Sandbar Hangout Key West
Powerboats in Key West · 6 guests

Boston Whaler 24ft Sandbar Hangout Key West

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

The Wanderlust Ultimate Catamaran Adventure

5.0
$642/hour
Instant Book
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
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
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
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
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
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
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
$707/hour
Luxury 33' Sea Ray Sundancer
Events in Aventura · 10 guests

Luxury 33' Sea Ray Sundancer

5.0
$90+/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
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

Paddleboard Reviews in Caribbean

  1. 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!!

  2. SA

    Sarah

    LUXURIOUS TIARA 40 EXPRESS

    Everything was perfect! The boat was incredible and had a bathroom and kitchen. The snacks and burgers were great. We went to Icacos for the day and it was beautiful! Would absolutely book with Miguel again!

  3. 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!

  4. 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!

  5. Matt

    Matt

    Beautiful Azimut Italian yacht 55’ Flybridge

    My family had an AMAZING voyage with Captain Lee on a sick yacht! The boat was pristine! Comfortable lounging areas in the sun and shade and nice cold A/C when it got to hot. Lee was a Captain of captains! Can't wait until our next one!

  6. Elizabeth

    Elizabeth

    The Wanderlust Ultimate Catamaran Adventure

    Gabrielle was kind, professional, very responsive and helpful.