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Caribbean Boat Rentals & Yacht Charters - 2026

4.8
(25,137 Reviews)

Page 45 of 141 • 3,369 listings

⭐⭐⭐Miami Escape – 60ft Azimut Flybridge Luxury Yacht Experience
Events in Miami · 13 guests

⭐⭐⭐Miami Escape – 60ft Azimut Flybridge Luxury Yacht Experience

5.0
$210/hour
Instant Book
Enjoy 21ft Monterey in Cape Coral (minimum 3 days rental)
Powerboats in Cape Coral · 8 guests

Enjoy 21ft Monterey in Cape Coral (minimum 3 days rental)

5.0
$175+/day
Cap Cana Private yacht sandbar & snorkel - Cap Cana, Punta Cana
Powerboats in Punta Cana · 18 guests

Cap Cana Private yacht sandbar & snorkel - Cap Cana, Punta Cana

4.6
Superowner
$190/hour
Full Day Aboard MV Hydra Luxury Power Catamaran
Powerboats in St. Thomas · 12 guests

Full Day Aboard MV Hydra Luxury Power Catamaran

5.0
$1,795/day
60ft PRIVATE YACHT CRUISE + FREE HOUR
Events in Miami · 13 guests

60ft PRIVATE YACHT CRUISE + FREE HOUR

New
$100+/hour
Ultimate Day Sailing Charter Onboard 40' Baba Sailboat in St. Thomas
Sailing in St. Thomas · 6 guests

Ultimate Day Sailing Charter Onboard 40' Baba Sailboat in St. Thomas

5.0
$220/hour
Charter 80' Ferretti Power Mega Yacht in Miami, Florida
Events in Aventura · 13 guests

Charter 80' Ferretti Power Mega Yacht in Miami, Florida

5.0
$1,000/hour
Enjoy Miami in our 70ft Sunseeker Manhattan Yacht
Events in Miami Beach · 13 guests

Enjoy Miami in our 70ft Sunseeker Manhattan Yacht

New
Superowner
Best of 2026
$950/hour
Sailing Charters On 37' Hunter Legend Cruising Monohull In Virgin Islands
Sailing in Charlotte Amalie West · 6 guests

Sailing Charters On 37' Hunter Legend Cruising Monohull In Virgin Islands

5.0
$210/hour
⭐⭐⭐Explore Biscayne Bay on 45' Sea Ray Express Cruiser in Miami
Events in Miami · 13 guests

⭐⭐⭐Explore Biscayne Bay on 45' Sea Ray Express Cruiser in Miami

New
$100/hour
Instant Book
Luxury Sailing Catamaran Charter in Fajardo, Puerto Rico
Sailing in Fajardo · 19 guests

Luxury Sailing Catamaran Charter in Fajardo, Puerto Rico

5.0
$450/hour
Starcraft 23ft Fort Lauderdale/Pompano for 12 Guests
Powerboats in Pompano Beach · 12 guests

Starcraft 23ft Fort Lauderdale/Pompano for 12 Guests

4.0
$69/hour
Charter a Center Console in Montego Bay, Jamaica
Powerboats in Montego Bay · 4 guests

Charter a Center Console in Montego Bay, Jamaica

4.9
$200/hour
Good times on the water - 22 foot Pontoon Sun Tracker
Powerboats in North Miami Beach · 11 guests

Good times on the water - 22 foot Pontoon Sun Tracker

5.0
$85+/hour
Enjoy Cartagena on a 55ft Azimut Luxury Yacht!
Events in Cartagena · 18 guests

Enjoy Cartagena on a 55ft Azimut Luxury Yacht!

New
Superowner
Best of 2026
$223/hour
62' Azimut “Priceless” | Luxury Miami Yacht Charter
Events in Miami Beach · 13 guests

62' Azimut “Priceless” | Luxury Miami Yacht Charter

5.0
$680+/hour
2023 Pardo 43 – Modern Performance & Luxury in Miami
Events in Miami · 12 guests

2023 Pardo 43 – Modern Performance & Luxury in Miami

5.0
$625+/hour
Charter 42' Whistle Wind Motor Yacht in Port of Spain, Trinidad and Tobago
Events in Trinidad and Tobago · 20 guests

Charter 42' Whistle Wind Motor Yacht in Port of Spain, Trinidad and Tobago

5.0
$910/day
Your Perfect Day on the Water Starts Here 219FS Key West in SWFL Bonita Springs
Powerboats in Cape Coral · 8 guests

Your Perfect Day on the Water Starts Here 219FS Key West in SWFL Bonita Springs

5.0
$85/hour
2026 VIP Birthday Celebration - Bachelor-bachelorette And More! Book Now!
Events in Bávaro · 100 guests

2026 VIP Birthday Celebration - Bachelor-bachelorette And More! Book Now!

New
Superowner
Best of 2026
$17/hour
31' Wellcraft. New, Fast Powerboat for Full Day in St. Thomas
Powerboats in St. Thomas · 12 guests

31' Wellcraft. New, Fast Powerboat for Full Day in St. Thomas

5.0
$1,450/day
60' Viking Princess Motor Yacht - Day Cruises Or Multi Day Charters!
Events in Aventura · 12 guests

60' Viking Princess Motor Yacht - Day Cruises Or Multi Day Charters!

5.0
$375+/hour
Inflatable motorboat 7 meters 2 x 115 hp 12 persons
Powerboats in Saint Martin · 12 guests

Inflatable motorboat 7 meters 2 x 115 hp 12 persons

5.0
Superowner
$613/day
Visit Saona Island and Natural Pool renting our yacht from Punta Cana
Events in Punta Cana · 12 guests

Visit Saona Island and Natural Pool renting our yacht from Punta Cana

5.0
$2,120/day

Caribbean Reviews

  1. Avri

    Avri

    Cap Cana Private yacht sandbar & snorkel - Cap Cana, Punta Cana

    My boyfriend and I had a great time on this boat. It was the perfect balance between attentiveness and privacy. We first went sailing along the coast near the marina, then scuba diving, and finally to a really beautiful “natural pool” which was crystal clear and the perfect way to end the trip. It was very fun and they had a Bluetooth speaker for us to sync our music. Carlos and José were awesome captains. We would definitely do this again.

  2. Caitlin

    Caitlin

    Sailing Charters On 37' Hunter Legend Cruising Monohull In Virgin Islands

    This was one of the best days of our lives! Christina and Jon were beyond accommodating. The drinks, the FOOD (get the lobster and mahi), the music, the snorkeling (saw so many beautiful fish and sea turtles!!) and the conversation were so enjoyable. These people know the islands so well and teach you a lot on top of giving you one of the best experiences of your life! Could not recommend it enough!!!!!

  3. KR

    Kelsey

    Sailing Charters On 37' Hunter Legend Cruising Monohull In Virgin Islands

    Jon and his team delivered the best experience of our St. John’s vacation. This is an island best seen by boat. Our kids are young (2,5,7). He customized an itinerary, snacks etc to the group. We went to one beautiful beach with turtles and a great snorkeling spot with fish. As our kids say, three thumbs up!

  4. LK

    Liz

    Sailing Charters On 37' Hunter Legend Cruising Monohull In Virgin Islands

    Jon and Christina were absolutely amazing! They made the experience so much fun and were very accommodating to everything we wanted to do, whether snorkeling, bringing us into to hang on the beach or whatever we wanted to experience. They also served the best food and drinks, it was the best part of our trip!

  5. ML

    Michael

    Sailing Charters On 37' Hunter Legend Cruising Monohull In Virgin Islands

    We have been on multiple day trips around the water during our stay on St. John. Our trip with Jon and Christina was by far the best experience. They actually asked us for input and what we would like to see and do. The lunch they served us was the best meal we have had here on St. John. Not only was it the best experience, it was also the best value. I highly recommend this duo for a great afternoon of sailing and snorkeling. We will be back.

  6. Cherry

    Cherry

    Sailing Charters On 37' Hunter Legend Cruising Monohull In Virgin Islands

    The crew are knowledgeable about the islands, serve the best mango dip appetizer, and delicious pork and mahi mahi meals. Their snorkeling equpment is like new and works great. They give you masks and fins plus noodles for those who need assistance. Great value for money.