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All listings in Caribbean

Awesome paddleboard rentals in the Caribbean.

5.0
(166 Reviews)

Page 1 of 2 • 28 listings

Lets go boating like a local Sandbar hangout
Powerboats in Key West · 6 guests

Lets go boating like a local Sandbar hangout

4.8
$158+/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
$620/hour
Luxury 55' Yacht charter in Nassau Bahamas
Events in Nassau · 16 guests

Luxury 55' Yacht charter in Nassau Bahamas

5.0
$900/hour
Limited Availability
Incredible 45' Sea Ray Yacht for 13 Guests in Haulover sandbar!!
Events in Sunny Isles Beach · 13 guests

Incredible 45' Sea Ray Yacht for 13 Guests in Haulover sandbar!!

5.0
$115+/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 43' Beneteau Sailing Charter – Day Sails & Bahamas Trips
Sailing in Fort Lauderdale · 6 guests

Fort Lauderdale 43' Beneteau Sailing Charter – Day Sails & Bahamas Trips

5.0
$130+/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 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
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
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
Luxe 77' Azimut Yacht with Jetski, Seabob, Paddleboards, Serving The Bahamas
Events in Nassau · 12 guests

Luxe 77' Azimut Yacht with Jetski, Seabob, Paddleboards, Serving The Bahamas

New
$1,350+/hour
Twilight Snorkeling Cruise with Drinks & Gourmet Bites
Powerboats in Fajardo · 6 guests

Twilight Snorkeling Cruise with Drinks & Gourmet Bites

New
$185/hour
Luxe 80ft Lazzara w/ Jetski, Kayaks & More Water Toys in South Florida & Bahamas
Events in Boca Raton · 12 guests

Luxe 80ft Lazzara w/ Jetski, Kayaks & More Water Toys in South Florida & Bahamas

New
$1,000+/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
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
$726/hour
Mojito 44ft Catamaran - Luxury Private Charter - St Maarten or Anguilla
Caribbean · 16 guests

Mojito 44ft Catamaran - Luxury Private Charter - St Maarten or Anguilla

New
$2,100/day
Don't Worry 45ft Catamaran - Luxury Private Charter - St Maarten or Anguilla
Caribbean · 16 guests

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

New
$2,350/day
Catamaran Charter In San Blas Panama
Sailing in Guna Yala Comarca · 10 guests

Catamaran Charter In San Blas Panama

New
$1,229/night
All-inclusive Crewed Charter on 40ft Nautitech Sailing Catamaran in San Blas
Sailing in Guna Yala Comarca · 7 guests

All-inclusive Crewed Charter on 40ft Nautitech Sailing Catamaran in San Blas

New
$1,000/night
Couach 21m "NEREE"  from Anguilla
Events in Sandy Ground · 12 guests

Couach 21m "NEREE" from Anguilla

New
$7,376/day

Paddleboard Reviews in Caribbean

  1. EB

    Evan

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

    10/10 experience! D and the captain was very kind and wonderful. The boat was absolutely beautiful and the weather was perfect for the day. I would recommend to anyone to book with them. You will not be disappointed!

  2. AG

    Allison

    The Wanderlust Ultimate Catamaran Adventure

    We cannot say enough wonderful things about our charter! It was truly one of the best experiences we’ve had as a family. Captain David was fantastic—knowledgeable, easygoing, and absolutely wonderful with our kids. He took us on an amazing snorkeling adventure and made the experience so easy and fun for them. Ashley was the sweetest with our daughter and made us a delicious lunch, and Max completely made Jack’s day by letting him help around the boat. The whole crew was warm, fun, and incredibly accommodating. We made such special family memories and will absolutely be rebooking on our next trip. Couldn’t recommend them more!

  3. MH

    Missy

    Lets go boating like a local Sandbar hangout

    Couldn’t have asked for a better 40th birthday! Anthony helped us decided on the best spots for what we wanted to do. Mystic the pug was a welcome bonus. The most amazing and unexpected part was the incredible drone footage of our party enjoying the water that Anthony shot and shared with us. Definitely book with Anthony!

  4. JI

    John

    Lets go boating like a local Sandbar hangout

    Great time out with Anthony. He suggested a nice itinerary based on what we wanted to see. He very patiently taught my 13 year old son how to wake skate. Probably the highlight of his trip. Overall, couldn’t have asked for a better captain. We had a blast and hope to do it again.

  5. LL

    Lauren

    Lets go boating like a local Sandbar hangout

    Our trip was amazing!! I went with 3 other friends and the trip was perfect! Would highly recommend to anyone looking for a day out on a boat in key west! We loved going to the sand bars and floating. Will definitely books again next time we are back!

  6. Jb

    Jody

    Lets go boating like a local Sandbar hangout

    We cant say enough good things about Capt Anthony. He is very knowledgeable about the area and is a very capable, qualified operator. Our family spent 7 hours with him and it was money well spent. DONT RENT A BOAT...Hire Capt Anthony. We requested how we wanted the day to go and he exceeded our expectations. There is nothing negative we can think of to say. We look forward to visiting with him and his side kick Mystic the next time we go. Was the highlight of our trip to Key West! Way to go Captain!