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Cayman Islands Boat Rentals - 2026

Page 1 of 122 listings

Cruise, Chill & Soak Up Paradise – Private Boat Tour Experience
Powerboats in George Town · 9 guests

Cruise, Chill & Soak Up Paradise – Private Boat Tour Experience

5.0
$200+/hour
31ft Chaparral Yacht Charter from Cayman
Events in George Town · 10 guests

31ft Chaparral Yacht Charter from Cayman

4.9
$200+/hour
New addition! Lagoon 450 Catamaran
Sailing in George Town · 30 guests

New addition! Lagoon 450 Catamaran

5.0
$500/hour
Charters with Captain Bibi on a 30ft powerboat in Grand Cayman
Fishing in West Bay · 12 guests

Charters with Captain Bibi on a 30ft powerboat in Grand Cayman

5.0
$225/hour
Sailing Catamaran Grand Cayman for Sunrise, Sunset or Any Time Cruise
Sailing in West Bay · 20 guests

Sailing Catamaran Grand Cayman for Sunrise, Sunset or Any Time Cruise

5.0
$400/hour
Charter with captain Bibi in Grand Cayman (bigger capacity boat)
Powerboats in George Town · 35 guests

Charter with captain Bibi in Grand Cayman (bigger capacity boat)

5.0
$250/hour
40 ft Searay Sundancer in Grand Cayman
Events in George Town · 12 guests

40 ft Searay Sundancer in Grand Cayman

5.0
$350/hour
Beneteau Oceanis 473 Luxury Sailing Charter in Grand Cayman, Cayman Islands
Sailing in West Bay · 15 guests

Beneteau Oceanis 473 Luxury Sailing Charter in Grand Cayman, Cayman Islands

5.0
$350/hour
A 8-Guests Cobalt boat 252  Bowrider for Charter in George Town, Cayman Islands
Powerboats in West Bay · 8 guests

A 8-Guests Cobalt boat 252 Bowrider for Charter in George Town, Cayman Islands

5.0
$200/hour
Luxury Beneteau Sense 55 Sailing Yacht Rental in George Town, Cayman Islands
Sailing in George Town · 20 guests

Luxury Beneteau Sense 55 Sailing Yacht Rental in George Town, Cayman Islands

5.0
$425/hour
31ft SeaRay Sundancer Luxury Boat Chartering in Grand Cayman
Powerboats in George Town · 9 guests

31ft SeaRay Sundancer Luxury Boat Chartering in Grand Cayman

5.0
$300/hour
Offshore Thrills on a 32ft Regulator – Reel in the Adventure!
Fishing in George Town · 10 guests

Offshore Thrills on a 32ft Regulator – Reel in the Adventure!

New
$400/hour
Cobalt R5 Bowrider Boat Rental In George Town, Cayman Islands
Powerboats in George Town · 8 guests

Cobalt R5 Bowrider Boat Rental In George Town, Cayman Islands

5.0
$288+/hour
Private Custom Charter, Stingray City, Coral Reef Snorkeling, Starfish 34ft
Events in West Bay · 12 guests

Private Custom Charter, Stingray City, Coral Reef Snorkeling, Starfish 34ft

5.0
$225+/hour
45ft Sea Ray Sundancer Luxury Tour in Grand Cayman
Powerboats in George Town · 15 guests

45ft Sea Ray Sundancer Luxury Tour in Grand Cayman

New
$400/hour
Stingray City and Snorkeling Coral Gardens
Powerboats in West Bay · 10 guests

Stingray City and Snorkeling Coral Gardens

New
$250/hour
 Private Yacht Charters, Enjoy The Beautiful Cayman Waters in Comfort.
Events in George Town · 8 guests

Private Yacht Charters, Enjoy The Beautiful Cayman Waters in Comfort.

5.0
$375/hour
Private Custom Charter - 28ft Grady - Stingrays, snorkeling, Starfish, tubing.
Tours in West Bay · 8 guests

Private Custom Charter - 28ft Grady - Stingrays, snorkeling, Starfish, tubing.

New
$200+/hour
2008 Wellcraft Scarab Boat for Eco & Fishing Charters!
Powerboats in North Sound Estates · 8 guests

2008 Wellcraft Scarab Boat for Eco & Fishing Charters!

New
$300/hour
Experience the ultimate blend of luxury and relaxation, Enjoy The Caribbean Sun
Events in George Town · 10 guests

Experience the ultimate blend of luxury and relaxation, Enjoy The Caribbean Sun

New
$350/hour
The Ultimate Stingray City Tour
Tours in Rum Point · 15 guests

The Ultimate Stingray City Tour

New
$275+/hour
Private Boat Charter - Stingray City, Coral Gardens, Starfish Point, & many more
Powerboats in West Bay · 10 guests

Private Boat Charter - Stingray City, Coral Gardens, Starfish Point, & many more

New
$200/hour

Top Destinations Nearby

Cayman Islands Reviews

  1. JM

    John

    31ft Chaparral Yacht Charter from Cayman

    Yarick was the absolute best! super friendly guy, very accommodating in making the trip exactly what we wanted it to be. he let us control the aux, pick what we wanted to do, and how long we wanted to be there. he also knows all the best spots, specifically where the turtles Kirby and Charlie hang out:) would recommend to anybody! 10/10!!!!

  2. JD

    Jessica

    Sailing Catamaran Grand Cayman for Sunrise, Sunset or Any Time Cruise

    I cannot speak more highly of our sailing adventure with James and Nino! They were so accommodating, so much fun and took us to the most amazing spots for snorkeling. We even got to swim with stingrays. THE BEST EXPERIENCE!!!

  3. MJ

    Mariah

    New addition! Lagoon 450 Catamaran

    Capt Dean and Jasper were nothing less than amazing. The boat itself was beautiful, and had all the amenities my group needed and more. They were accommodating in more than ways than one and which allowed us to have an amazing experience. I was comfortable, and knew I was in good hands with our boating adventures. I thank both of them over and over and will definitely be the only captain/boat I book with when I visit the Cayman Islands.

  4. JT

    Jamie

    A 8-Guests Cobalt boat 252 Bowrider for Charter in George Town, Cayman Islands

    Do yourself a favor and don’t waste time or money with big company tours and all the people book private Cira and our captain were great 4 stops bunch pictures well worth it!!!

  5. DC

    David

    40 ft Searay Sundancer in Grand Cayman

    Awesome time in a great boat. We had a wonderful time exploring new spots, private areas for snorkeling and swimming. Captain and his crew mate were super friendly and fun.

  6. JS

    John

    A 8-Guests Cobalt boat 252 Bowrider for Charter in George Town, Cayman Islands

    Cira and Hank were great. It was so good having a private trip with individualized attention and not being crowded into a boat with 50 others. They made it a fun trip