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All listings in Caribbean

Awesome sailboat rentals in the Caribbean.

4.7
(2,254 Reviews)

Page 3 of 18416 listings

Beautiful Cruising Catamaran for Up to 20 Friends in Cartagena, Colombia
Sailing in Cartagena · 20 guests

Beautiful Cruising Catamaran for Up to 20 Friends in Cartagena, Colombia

4.8
Superowner
$900/day
All Inclusive, Luxury 42 Lagoon Catamaran Adventure in Fajardo, Puerto Rico
Sailing in Fajardo · 12 guests

All Inclusive, Luxury 42 Lagoon Catamaran Adventure in Fajardo, Puerto Rico

5.0
$467+/hour
44 Luxury Catamaran BIG BEN
Sailing in Leeward Settlement · 18 guests

44 Luxury Catamaran BIG BEN

5.0
$875+/hour
Lagoon 38 Catamaran trip in St Martin with skipper, departure from Orient bay
Sailing in Saint Martin · 12 guests

Lagoon 38 Catamaran trip in St Martin with skipper, departure from Orient bay

4.9
Superowner
$1,130/day
Lagoon 450 Sailing Catamaran Charter in Saint Martin Community
Sailing in Saint Martin · 20 guests

Lagoon 450 Sailing Catamaran Charter in Saint Martin Community

4.9
$1,826/day
Punta Cana Booze Cruise Experience  Snorkeling • Sandbar • Music • Drinks
Events in Punta Cana · 180 guests

Punta Cana Booze Cruise Experience Snorkeling • Sandbar • Music • Drinks

4.0
Superowner
Best of 2026
$17/hour
⛵️ Catamaran Party Boat with Captain & Crew – Up to 42 Guests!
Sailing in Miami Beach · 42 guests

⛵️ Catamaran Party Boat with Captain & Crew – Up to 42 Guests!

4.8
Superowner
$700+/hour
⛵️ Catamaran 49-Person Party Boat Includes: 1-Captain, 1-Mate and 1-Bartender
Sailing in Miami Beach · 49 guests

⛵️ Catamaran 49-Person Party Boat Includes: 1-Captain, 1-Mate and 1-Bartender

5.0
Superowner
$700+/hour
Private Sail Aboard Classic 1969 Sloop in San Juan, Puerto Rico
Sailing in San Juan · 6 guests

Private Sail Aboard Classic 1969 Sloop in San Juan, Puerto Rico

4.9
Superowner
$198/hour
Sail In Caribbean Paradise with Jeanneau Sun Odyssey 44
Sailing in Jolly Harbour · 6 guests

Sail In Caribbean Paradise with Jeanneau Sun Odyssey 44

4.9
$280/day
🏝️Exciting Private Yacht: Affordable Charter with Crew🎉
Events in Punta Cana · 250 guests

🏝️Exciting Private Yacht: Affordable Charter with Crew🎉

3.0
Superowner
Best of 2026
$17/hour
Exclusive Escape with Ocean Explorer Catamaran in Punta Cana
Powerboats in Uvero Alto · 30 guests

Exclusive Escape with Ocean Explorer Catamaran in Punta Cana

4.8
Superowner
Best of 2026
$16/hour
3.5hr Catamaran Experience Montego Bay
Sailing in Montego Bay · 30 guests

3.5hr Catamaran Experience Montego Bay

5.0
Superowner
$834/hour
Private Luxury Bali 4.0 Catamaran with 3 Cabin from Old San Juan
Sailing in San Juan · 12 guests

Private Luxury Bali 4.0 Catamaran with 3 Cabin from Old San Juan

5.0
$575/hour
45' Sea Ray Yacht Charter in Turks & Caicos
Powerboats in The Bight Settlement · 15 guests

45' Sea Ray Yacht Charter in Turks & Caicos

5.0
$500/hour
Sailing From Pompano Beach, FL
Sailing in Pompano Beach · 12 guests

Sailing From Pompano Beach, FL

4.6
Superowner
$125+/hour
60ft AIcon Yacht – Perfect for Luxury Day Trips
Events in Miami · 13 guests

60ft AIcon Yacht – Perfect for Luxury Day Trips

4.8
$350/hour
3hr Classic Yacht Experience Montego Bay
Powerboats in Montego Bay · 35 guests

3hr Classic Yacht Experience Montego Bay

5.0
Superowner
$933/hour
34ft Pacific Seacraft Sailboat for full day Trip in Santa Marta, Magdalena
Sailing in Santa Marta · 12 guests

34ft Pacific Seacraft Sailboat for full day Trip in Santa Marta, Magdalena

5.0
$100/hour
Great Catamaran for Cholon, Barú, sunset cruise, lunch or dinner on board...
Sailing in Cartagena · 45 guests

Great Catamaran for Cholon, Barú, sunset cruise, lunch or dinner on board...

4.9
Superowner
$1,000/day
Let's go Sailing in Miami!
Sailing in Miami · 6 guests

Let's go Sailing in Miami!

5.0
$45+/hour
Exclusive Private boat rental to any occasion in punta cana🥳
Events in El Cortecito · 30 guests

Exclusive Private boat rental to any occasion in punta cana🥳

New
Superowner
Best of 2026
$10/hour
Janise Sailing Afternoon Charter - Fajardo, Puerto Rico 🇵🇷
Sailing in Fajardo · 6 guests

Janise Sailing Afternoon Charter - Fajardo, Puerto Rico 🇵🇷

4.9
$995/day
Limited Availability
Private Tours~ Snorkeling at Palomino & Icacos Islands- Pursuit 28'
Tours in Fajardo · 6 guests

Private Tours~ Snorkeling at Palomino & Icacos Islands- Pursuit 28'

5.0
Superowner
Best of 2026
$675/day

Sailing Reviews in Caribbean

  1. ML

    Myeves

    Private Tours~ Snorkeling at Palomino & Icacos Islands- Pursuit 28'

    i had the most amazing time. from all the gadgets they had like floaters, beach volleyball, and snorkels/flippers we were set up for success!!! he took such good care of us and even pointed out where to snorkel, WE GOT TO SEE TURTLES !!! food was delicious and service was great (at one point i had salt water in my eye and he helped wipe it!). truly an amazing group of gentleman that i hope i get to meet again!

  2. PC

    Paris

    Private Tours~ Snorkeling at Palomino & Icacos Islands- Pursuit 28'

    ⭐⭐⭐⭐⭐ We had an amazing experience and couldn’t have asked for a better day on the water! The captain took us to beautiful spots with crystal-clear water, and each stop was perfect for swimming and relaxing. The snorkeling was incredible, with plenty to see and a great selection of gear provided. The food was fresh and delicious, and the drinks kept coming all day. You can tell they truly care about making sure everyone has a fun, memorable experience. If you’re looking for a private boat trip in Puerto Rico, I highly recommend booking with them. Professional, friendly, and worth every penny. This was easily one of the highlights of our vacation, and we would absolutely book again!

  3. Melissa

    Melissa

    Lagoon 450 Sailing Catamaran Charter in Saint Martin Community

    We had such a great time! Robin and Bonnie welcomed us onto the boat with a spread of pastries and unlimited waters, sodas, beers, wine, and mixed drinks. At each stop they got out the floating mat and we were able to snorkel or paddle board. We also had fun jumping off the side of the boat. There was lots of space on the boat with ample spots for shade and sun. Everyone agreed, this was the best part of our vacation!

  4. lb

    lauren

    Lagoon 38 Catamaran trip in St Martin with skipper, departure from Orient bay

    We had a wonderful day on this boat! The captain was great, took us to the best spots for snorkeling and lunch, and we loved leaving from Orient Bay so we didn’t have to sail as long in the rougher waters. Spectacular day all around and highly recommend

  5. Nelson

    Nelson

    Private Tours~ Snorkeling at Palomino & Icacos Islands- Pursuit 28'

    Jose and his crew were fantastic. The food was excellent, communication was great, timing was spot on, and the service throughout the entire experience was outstanding. Highly recommend!

  6. LL

    Luke

    All Inclusive, Luxury 42 Lagoon Catamaran Adventure in Fajardo, Puerto Rico

    Minell was awesome helping set up everything. We rented a catamaran and it was so much fun. Hands down highlight of our trip! She took care of the bus there and back as well which was nice.