Cayman Castle & Guesthouse

127 people have viewed this property this week.
7 Bedrooms
7.5 Bathrooms
20 Sleeps

Cayman Castle and Guesthouse sits directly oceanfront on a private 2-acre gated estate and enjoys a wide white-sandy beach with fabulous snorkeling, kayaking, and sunbathing. Two private pools, multi-tiered oceanfront terraces, a panoramic veranda balcony, and a well-shaded pool deck provide guests plenty of room to spread out and enjoy island living. The views are breathtaking.

This grand estate is not only one of the largest rental villas on the entire island, but it also is a notable landmark.  Virtually anyone on the island will be familiar with the Castle in the East End.  While we are neighbors to the Wreck of The 10 Sails Park and the police constable's residence to the north, this property enjoys no residential neighbors to the north or south for 500 feet in either direction.  This is a gated and walled estate with a private beachfront. 

The owner takes immaculate care of the home, making upgrades each fall to keep the experience not only refreshing and pleasant for repeat guests, but for newcomers to Cayman as well.

20 guests maximum, of whom 16 may be adults 18 years or older.  Up to 2 infants, sleeping in cribs do not count against guest occupancy.  

Sleeping Arrangements
(Sleeps 20 guests total, 16 adults max)

  • Master Suite – spans entire third-floor, oceanfront views, walk-out sun terrace, furnished with a king bed, TV, small dining table, and ensuite bath with walk-in shower. 2 Adults
  • South King Suite – second-floor, ocean views, furnished with a king bed, bed bench, small workstation, and ensuite bath with walk-in shower. 2 Adults.
  • Family King Suite – second-floor, furnished with a king bed and set of quality RH bunk beds, ensuite bath with walk-in shower. 4 persons max.; 3 of whom can be adults.
  • Queen Suite – lower-level with private outside entry, ocean views, walk-out access to the pool deck, furnished with queen bed, TV, and ensuite bathroom with walk-in shower. 2 Adults
  • Bunk Suite – lower-level, furnished with strong full-over-full bunk beds, TV with Apple TV for streaming, private ensuite bath with walk-in shower. 2 Adults or 4 children permitted.
  • Guesthouse Suite #1 – Oceanfront king suite with stunning views, desk, large chairs, private ensuite bath with large walk-in shower
  • Guesthouse Suite #2 – Oceanfront queen/family suite with stunning views, bunk beds, large chairs, private ensuite bath with dual vanities and walk-in shower

Cayman Castle & Guesthouse Unique Features


  • Two oceanfront pools! The main house features a gorgeous oceanfront infinity pool (heated to 84 degrees in the winter gratis), while the guesthouse enjoys a smaller, but very private pool.
  • 500 feet of shoreline, 200 feet is sandy beach. Step off our driveway onto white sand!
  • 3 thatched beach palapas, 4 kayaks (2 tandem and 2 single), and walking distance to Ocean Frontiers dive shop, 3 restaurants make this home a convenient choice for larger families. Call Tukka Restaurant to send their complimentary van!
  • Custom 17-foot mosaic dining table on the main porch seats 18-20 and offers panoramic views while you dine.
  • A flight of stone steps from the pool deck takes you past the Adirondacks and loungers on the sunny patio and down to the water, where guests can enjoy excellent snorkeling or kayaking. A healthy marine ecosystem awaits your discovery—so we ask that you wear pool shoes or fins when you enter the water!
  • Propane BBQ cooking center with granite top between Castle & Castle Guesthouse 
  • Private driveways, with plenty of off-street parking for guests. 
  • Lounge chaises and outdoor sectionals on the pool decks, porches, and balconies. Our guests can relax in the sun or shade. Outdoor table for 8 under the pool-side verandah.
  • Separate L-shaped bar with a beverage fridge just off the pool area.
  • Multiple roofed verandas at both Castle & Guesthouse provide guests protection from the sun.   


  • Kitchen, dining, and living area are all oceanfront on the second floor, offering lovely panoramic views through the multiple sliding glass doors that lead to the main level roofed balcony and outdoor seating area. Dining table seating 20 max
  • Modern kitchen features GE oven, Bosch dishwasher, 48" SubZero refrigerator, ceramic glass stovetop, microwave, Keurig & drip coffeemakers, Kitchenaid mixer, drip coffeemakers, blenders and tons of counter space. Barstool seating in Castle for 8
  • Indoor breakfast table for 6 at Castle, 4 at Guesthouse
  • Comfortable living area with 60" flatscreen TV and full channel programming for unwinding after a day of sun and surf. WiFi internet with extenders for the pool and balcony areas.
  • Bar area with wine/beverage fridge adjacent to the lower level pool deck
  • Back-up, full-sized fridge, and icemaker in laundry
  • Plenty of dishes, utensils, glassware, barware and cookware provided

Castle Guesthouse Unique Features

  • Full modern kitchen with refrigerator/freezer, Bosch dishwasher, stove, oven, microwave, blender, and coffeemaker.
  • Comfortable sectional sofa with large flatscreen TV.
  • Outdoor sectional sofa as well as Adirondack chairs.
  • Dining table seating for 4.

Both homes come equipped with central A/C, complimentary WiFi, Apple TV.  The kitchens are stocked with dishes, glasses, cookware, and utensils.  Linens, towels, and beach towels are also provided for guests.

*Note: A Cleaning Fee is inlcuded due to enhanced cleaning, sanitation, and inspection protocols.

**Additional Silver Thatch tandem kayaks available for discounted rental.  Signed waiver required. 

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Infinity Pool (Heated in winter)
Gated Privacy
Snorkeling Reef
Private Barefoot Beach
Beach Chaises & Thatched Palapas
2 Sundecks
4 Owner Provided Kayaks
Short Walk to Dive Shop
Propane Grill
Bluetooth Speaker
High-speed Fiber Internet
Keyless Entry
5 Flatscreen TVs
iMac Computer
Satellite TV
4 Apple TVs
Central A/C
Keurig Coffee Maker
Ice Coolers
Beach & Bath Towels Provided
Hair Dryers
Additional Kayaks for Rent

Beach Notes

Cayman Castle sits on a 2 acre gated estate in Gun Bay in East End; adjacent to 6 acres of government land that includes the Wreck of the 10 Sails park and the East End Constable's residence & office. 

2-3 lunch places are within walking distance and Tukka Restaurant is only a mile north. Two miles north are the 2 large resorts (Morritt's and The Reef) where they maintain manicured beaches, pools, restaurants, bars and watersports. Those resorts are great places to entertain older kids and for anyone to spend the day.

The beach at the Castle is white sand and is quite private. We have three thatched palapas, 4 kayaks and 6 lounge chaises on the beach. Most folks will spend the day sunning around the pool but we offer the beach option too. The water is more snorkeling than swimming is a marine environment and we recommend pool shoes or fins. 

You can walk down our stairs on the point to sit down and put on your fins as well. We have a great snorkeling site straight out 200 yds from the castle marked with a white PVC pole. You may also tie up the kayaks to that pole as well.

General Grand Cayman Beach Notes

All beaches in Grand Cayman are technically “public” since the Queen owns up to the high water mark and the shoreline quality behind your property may vary seasonally. Be advised that the beach or water entry behind your property may vary slightly from the images on our website because of the weather. The next-door beach is also always available for your use.

Ocean Debris & Sargassum Seaweed

Beaches in Grand Cayman may also experience floating ocean debris and sargassum weed seasonally. Sargassum is a generally harmless floating seaweed that has increased in frequency in recent years. Although sargassum is an unsightly nuisance, it is largely seasonal in summer. Our owners do make efforts to remove heavy sargassum and will have the beach raked prior to your arrival. 

Should sargassum weed be extremely heavy behind your property, we will reach out to the owner for alternative solutions which may include a partial refund or relocation. We try our best to work around mother nature.


The 10% Guest Service Fee includes your Silver Thatch Membership.

The Guest Service Fee is capped at 10 days for extended stays. 

Member Benefits

  • Centralized on-island Guest Services & Welcome Center
  • Unlimited use of Silver Thatch Fitness Center (18+ yrs.)
  • Business Center Access: computers, printer, scanner, & FedEx/DHL supplies
  • Proprietary Silver Thatch Guest Discount Card
  • 10% advance booking discount for private charter
  • Complimentary use of snorkel equipment
  • Guest parcel receipt & hold for check-in
  • Jacques Scott Wine & Spirits pre-order & hold for check-in
  • Referral to preferred vendors, guest services desk assistance
  • Airport arrival Fast-Track VIP Process (fee charged by CAA)
  • Special event/dinner reservations

At-Villa Benefits

  • Welcome amenity basket
  • Complimentary early check-in, if no check out on same day
  • Day-after-arrival guest services follow-up
  • Gilchrist & Soames bath products
  • Pre-stocking of groceries & beverages (delivery fee applies)
  • Arrange chefs, cooks, babysitting & family photography
  • $3,000 of Accidental Villa Damage Protection
  • Complimentary pack-n-plays, booster seats, & baby gates
  • Additional tandem kayaks available for discounted rental*

*Signed waiver required.

Guest Reviews of Cayman Castle & Guesthouse

442 Austin Connally Drive Grand Cayman , 

5 out of 5 stars based on 3 user reviews

Perfect Location

Review by Tony Erskine on 08/27/2022
5 out of 5
It's quiet and private a totally different experience from Georgetown!

Great Spot - Cayman Castle + Guesthouse

Review by Kevin on 04/18/2022
5 out of 5
Great house for a large family. We had 17 with 9 grandkids. The pool was great for the kids and the location was private and relaxing with several good restaurants within a 10 minute drive. One of the best dive operations on the island is within 500 yards down the beach.

Property Exceeded our Highest Expectations

Review by Sean on 12/17/2019
5 out of 5
Property exceeded our high expectations. It was the perfect property for large extended family, as grandparents stayed in smaller unit. We liked being away from the busy side of the island and enjoyed being walking distance to many restaurants and the snorkel/dive shop. Manager was very responsive is our small requests. We hosted a chef one night and the house was perfect for that, especially that large outdoor deck for dinner. We would definitely stay there again

Booking Rules

  • 5 nights minimum required.
  • 6 nights minimum and full occupancy required over Thanksgiving week.
  • 7 nights minimum and full occupancy required over Christmas and New Year's week.
  • Christmas & New Year's are split into two rental periods. Please inquire directly with your travel dates prior to booking.
  • Shorter stays may be available but subject to a higher cleaning fee. Please inquire before booking.
  • Discounts offered for multi-week stays. Ask for Promo Code
  • Must be 25 years or older to book, and must occupy the home during the entire stay.

Villa Cleaning & Sanitation

All villas are cleaned and sanitized prior to each guest's arrival. We also ask our owners to provide a starter supply of extra cleaning products.

Additional housekeeping services can be purchased after booking in 3-hour time blocks. Scheduling may be coordinated with your property manager upon arrival.

Taxes & Fees

  • 13% Occupancy Tax added to all rates
  • 10% Guest Service Fee includes your Silver Thatch Membership
  • Guest Service Fee is capped at 10 days for extended stays
  • The owner requires a $2,500 refundable excess cleaning and damage deposit
  • We accept Visa, MC, Discover, and Bank Wire for payments. 

Map Notes

Nearby Points of Interest

Getting Around

A rental car is highly recommended. Taxi cabs are unreliable and expensive outside of town and Seven Mile Beach. Plus, there is no Uber or Lyft on the island

For rental cars, we recommend AvisMarshalls, or Hertz

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