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Browse Cayman Island Boat Rentals.

Page 1 of 118 listings

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
Navigate your way to fun with us!
Powerboats in George Town · 9 guests

Navigate your way to fun with us!

5.0
$175+/hour
31ft Chaparral Yacht Charter from Cayman
Events in Rum Point · 10 guests

31ft Chaparral Yacht Charter from Cayman

5.0
$200+/hour
Instant Book
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
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
$300/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
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
Instant Book
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
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
Instant Book
40' Motor Yacht Charter - Friendly North Sound Exploration, Swim, Snorkel, Relax
Events in George Town · 10 guests

40' Motor Yacht Charter - Friendly North Sound Exploration, Swim, Snorkel, Relax

5.0
$250/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
The Ultimate Stingray City Tour
Tours in Rum Point · 15 guests

The Ultimate Stingray City Tour

New
$275+/hour
Your perfect day on our 380 Searay, in the Cayman Islands,
Events in George Town · 8 guests

Your perfect day on our 380 Searay, in the Cayman Islands,

New
$375/hour
Private Yachting & Adventure Tours in Paradise
Events in West Bay · 25 guests

Private Yachting & Adventure Tours in Paradise

New
Snoozed - Active 17 Oct 2025

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Cayman Islands Reviews

  1. mariano

    mariano

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

    We had an amazing experience with captain Oneil (hope I am spelling is right) and Nino. The boat was amazing and comfortable and both of them cater to our needs and requests to ensure we had a very amazing and customized experience. Karen who helped us book was also super communicative and kind to help us through the booking process!

  2. zr

    zachery

    31ft Chaparral Yacht Charter from Cayman

    If I could give 10 stars I would! Nick and Carlos were hands down some of the best crew we’ve ever had. The stops were amazing, they knew what they were doing and they were right on time. The boat while older was well maintained and a great value, I will be booking again on our next vacation!

  3. DE

    Dana

    Navigate your way to fun with us!

    Dillan was fantastic at communication before our trip. We did a bio bay/starfish point evening charter and then a 5 hour morning sting ray city/snorkel charter with him. His boat was well maintained and clean. He was professional and knowledgeable. We had a fantastic experience and would recommend him to anyone!

  4. TM

    Tina

    Navigate your way to fun with us!

    Booked for a 6 hour tour. Visited stingray city (a must), snorkeled, looked at million dollar homes(so fun) had a great lunch then ended the day with a stop at Starfish beach. It was a fabulous day. On a side note, left my wallet on the boat and Dillan brought it to us even after we told him we would meet him. We actually booked a day fishing with them after this trip, would recommend 100%!

  5. AS

    Amanda

    31ft Chaparral Yacht Charter from Cayman

    We had the most amazing day with this crew! My kids said it was the best day we had on vacation. They got to swim with stingrays, play sand volleyball at rum point and snorkel! Amazing experience!

  6. JD

    Jim

    Navigate your way to fun with us!

    Had a great trip. Hooked us up on a shark and a huge queen trigger fish as well as many others. Offered to change our start time due to tides in order to maximize fishing. Would do again.