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All listings in Caribbean

Awesome paddleboard rentals in the Caribbean.

5.0
(289 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
$195/hour
50ft Catamaran Charter with Water Toys - Deerfield/Boca Raton, FL
Sailing in Deerfield Beach · 12 guests

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

5.0
$350/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
2018 Godfrey Sweetwater 23' Pontoon Available Throughout All SWFL
Powerboats in Bonita Springs · 12 guests

2018 Godfrey Sweetwater 23' Pontoon Available Throughout All SWFL

5.0
$340+/day
💎 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
$1,688+/hour
Instant Book
Snorkeling & Boat Experience with Lunch and Drinks!
Powerboats in Fajardo · 6 guests

Snorkeling & Boat Experience with Lunch and Drinks!

5.0
$150/hour
  #1 CHARTER IN KEY LARGO!! sandbar trips,  island hopping, reef tours.’!
Events in Key Largo · 6 guests

#1 CHARTER IN KEY LARGO!! sandbar trips, island hopping, reef tours.’!

5.0
Superowner
$180/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

5.0
$178/hour
Boston Whaler 24ft Sandbar Hangout Key West
Powerboats in Key West · 6 guests

Boston Whaler 24ft Sandbar Hangout Key West

4.9
$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
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
Best of 2025
$160+/hour
WOW! Delray Beach $319!! per hour
Events in Delray Beach · 12 guests

WOW! Delray Beach $319!! per hour

5.0
$319/hour
Sport Cruiser Exodus Experience Tour in Montego Bay
Events in Montego Bay · 11 guests

Sport Cruiser Exodus Experience Tour in Montego Bay

5.0
$840/hour
Fort Lauderdale Bahamas Sailing Charters
Sailing in Fort Lauderdale · 6 guests

Fort Lauderdale Bahamas Sailing Charters

5.0
$130+/hour
Discover St Maarten on this beautiful catamaran
Sailing in Upper Prince's Quarter · 15 guests

Discover St Maarten on this beautiful catamaran

5.0
$1,750/day
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
Ultimate Sailing Adventure
Sailing in Nassau · 12 guests

Ultimate Sailing Adventure

New
$375/hour
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
79ft Ferretti Yacht | Includes 4 Suites 4 Bathrooms Jet Skis Water Toys Jacuzzi
Events in Miami · 13 guests

79ft Ferretti Yacht | Includes 4 Suites 4 Bathrooms Jet Skis Water Toys Jacuzzi

New
$625+/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
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
$800/hour
Beneteau 48 Motor Yacht Charter St Barths | St Martin | Anguilla
Events in Gustavia · 10 guests

Beneteau 48 Motor Yacht Charter St Barths | St Martin | Anguilla

New
$600/hour
Night Snorkeling Boat Experience with Snack and Drinks
Powerboats in Fajardo · 6 guests

Night Snorkeling Boat Experience with Snack and Drinks

New
$185/hour
Stand Up Paddleboard Rental Experience
Adventures in Fajardo · 1 guest

Stand Up Paddleboard Rental Experience

5.0
$25/hour

Paddleboard Reviews in Caribbean

  1. DS

    Domenic

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

    This was a great experience. We were 2 families on spring break with 5 teenagers and everyone had a large time. Fantastic Catamaran and exceptional captain (Jamie) and first mate (Kristen). We had so much fun we extended our trip. Well worth the price.

  2. GC

    Guilherme

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

    The boat trip was perfect! The boat was clean and well-organized, and we were offered drinks and snacks. Also, the sailor Mike was very respectful and fun, which made the trip even more special! We highly recommend it.

  3. CV

    CARLOTA

    Boston Whaler 24ft Sandbar Hangout Key West

    The experience was amazing! The places are very beautiful. It was just a shame the miscommunication: when I booked I had agreed that we’d stop for lunch at a restaurant and the capitain didn’t know about it.

  4. LE

    Lia

    Fort Lauderdale Bahamas Sailing Charters

    Truly incredible experience with Jose and Alex. Absolutely magical adventure and highly recommended to anyone looking for an unforgettable time. The food was also out of this world and so much attention to detail in every moment. We will absolutely be back and everyone needs to experience this.

  5. MB

    Meredith

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

    We had an absolutely amazing trip with Miguel! I cannot recommend this experience highly enough, he made everything so easy and fun and my group had an amazing time in Icacos. You won’t regret booking!

  6. CH

    Cody

    #1 CHARTER IN KEY LARGO!! sandbar trips, island hopping, reef tours.’!

    This boat tour was nothing short of spectacular! From start to finish, this experience exceeded all of our expectations. The boat was spacious, comfortable, and well maintained. The captain was attentive to all our needs, ensuring we were comfortable and always having a great time. Whether we were enjoying the serene moments of the journey or engaging in some fun water activities, he was always made sure we had everything we needed. His warm, laid-back approach made us feel like we were cruising with an old friend. This tour was the perfect mix of relaxation, adventure, and breathtaking natural beauty. If you’re looking for an unforgettable family experience on the water, this private boat tour is an absolute must. Thank you again- and we plan to be back! Your AR friends.