
Cayman Castle & Guesthouse
- Overview
- Amenities
- Calendar
- Rates
- Guest Services
- Beach Notes
- Map
- Reviews
- Floor Plan
- Virtual Tour
- Video
- Book Now
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 infinity 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.
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 beach within.
The owner takes immaculate care of the homemaking upgrades every fall to keep the experience not only refreshing and pleasant for repeat guests, but for newcomers to Cayman Island as well.
18 guest maximum, of whom 14 may be adults 18 years or older. Infants in cribs do not count against guest occupancy.
Cayman Castle & Guesthouse's Sleeping Arrangements
(Sleeps 18 guests total, 14 adults max)
- Oceanfront Master Suite – Gorgeous, third-floor oceanfront master king suite on its own floor with private roofed balcony, TV, panoramic views, table desk and private ensuite bathroom with a spacious walk-in shower
- Second Floor Guest Suite #1 – King suite with ocean views, bench, desk, chair, and private ensuite bath with walk-in shower
- Second Floor Guest Suite #2 – King suite with ocean views, sturdy bunk-beds (for child/teen suite or young family) and private ensuite bath with walk-in shower
- First Floor Suite – Queen suite with ocean views, private entry from the pool deck, sitting area, TV, and private ensuite bathroom with walk-in shower
- First Floor Bunk Suite – Bunkbed suite with two full-over-full bunks (easily sleeps 4 small children), a large smart/Apple TV for movies, private ensuite bath with walk-in shower. 2 folding cribs stored in this bedroom.
- Guesthouse Suite #1 – Oceanfront king suite with stunning views, desk, large chairs, and private ensuite bath with a large walk-in shower
- Guesthouse Suite #2 – Oceanfront queen suite with stunning views, one set of bunk beds, large chairs, dual vanities, and private ensuite bath with walk-in shower
Cayman Castle’s Unique Features
OUTDOORS
- 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.
- 300 feet of private white sand 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 van for you free!
- Custom 17-foot mosaic dining table on the main porch seats 18 easily 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!
- Stainless steel propane BBQ cooking center with granite top between Castle & Castle Guesthouse
- Private driveway, 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 dining 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.
INDOORS
- 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 coffeemaker, Kitchenaid mixer, drip coffeemakers, blenders, mixer and tons of counter space. Barstool seating for 8
- Indoor breakfast table for 6-8
- 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.
- Similar 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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Amenities
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 here...it 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
- $2,500 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 ,9 user reviews
stars based onFantastic Home and Location
Fabulous Cayman Castle and guesthouse
Something Different than 7 Mile Beach
Exceptional Vacation Villa
A Wonderful Place for a Big Family to Have a Memorable Time
Manager Response:
Thank you for the kind review. We try to be responsive when things come up!
Scott
Grand Cayman Villas
Cayman Castle - Beautiful Spot!!!
Wonderful Property on Quiet Side of the Island
Cayman Castle Wedding
Manager Response:
So glad you had a nice time!!! Please come again soon!!!
Scott
Grand Cayman Villas
Fantastic vacation from start to finish
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Begins | Ends | Daily | Weekly | Bi-Weekly |
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Jan 06, 2021 | Mar 05, 2021 | $1,995 | $12,900 | $21,285 |
Mar 06, 2021 | Apr 16, 2021 | $2,295 | $14,500 | $23,925 |
Apr 17, 2021 | May 28, 2021 | $1,695 | $10,000 | $16,500 |
May 29, 2021 | Aug 20, 2021 | $1,895 | $12,000 | $19,800 |
Aug 21, 2021 | Nov 05, 2021 | $1,295 | $8,000 | $13,200 |
Nov 06, 2021 | Nov 19, 2021 | $1,595 | $9,500 | $15,675 |
Nov 20, 2021 | Nov 27, 2021 | $2,295 | $16,065 | |
Nov 28, 2021 | Dec 17, 2021 | $1,895 | $12,000 | $19,800 |
Dec 18, 2021 | Dec 25, 2021 | $2,950 | $20,500 | |
Dec 26, 2021 | Jan 04, 2022 | $3,650 | $24,900 | |
Jan 05, 2022 | Mar 05, 2022 | $1,995 | $13,000 | $21,450 |
Mar 06, 2022 | Apr 15, 2022 | $2,295 | $14,500 | $23,925 |
Apr 16, 2022 | May 27, 2022 | $1,695 | $10,000 | $16,500 |
May 28, 2022 | Aug 19, 2022 | $1,895 | $11,700 | $19,305 |
- 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
- Owner requires a $1,000 refundable excess cleaning and damage deposit
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.
- Must be 25 years or older to book, and must occupy the home during the entire stay.
Villa Cleaning & Sanitation
We're committed to the health and safety of all our guests and have adopted enhanced cleaning safeguards to suppress the spread of COVID-19.
All villas are cleaned and sanitized prior to each guest's arrival using health agency-approved cleaners and disinfectants. 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 on-island.
Flexible Cancellation Policy
I. CANCELLATION TERMS
1). Once the guest's signed rental contract is confirmed with a deposit, should the guest cancel in writing prior to 60 days of arrival, half of the initial deposit (usually 25% of rent) will be refunded to the card on file, less a 3.50% processing/admin fee of the deposit. Should the villa owner be able to replace the reservation in whole or in part, the (prorated) un-refunded balance of the initial deposit will be returned less any re-booking costs incurred. Should the owner not be able to replace the reservation, the balance of the initial deposit is forfeited.
***PANDEMIC/EPIDEMIC EXCEPTION: Should a declared Pandemic or Epidemic prevent reasonable air transport options to the Cayman Islands, the guest may cancel and the entire initial deposit will be refunded, less a processing/admin fee of 3.50%.
2). Once full payment has been made (or the 60-day mark has passed and the guest has not paid the balance), should the guest cancel in writing, GCVC will refund any occupancy taxes, cleaning fees, cancelable services, and refundable damage deposits to the card on file. The dates will be opened on the calendar for rebooking. Should the reservation be replaced in whole or part, the guest will receive up to 100% of monies paid less a 3.50% admin/processing fee or rebooking charges incurred. Should GCVC not be able to replace the reservation, the rent and service fee will be forfeited; however, the guest will receive a credit for 50% of rent to be used for a similar stay at the same property, taken within 13 months of the original date of arrival.
***PANDEMIC/EPIDEMIC EXCEPTION: Should a declared Pandemic or Epidemic prevent reasonable air transport options after full payment, the guest may cancel up until the day of arrival and all payments will be refunded, less a 3.50% processing/admin fee on all monies processed.
***HURRICANE WARNING EXCEPTION: Should a hurricane warning (not a hurricane watch) affect Grand Cayman's ability to welcome guests; the guest will have the option of rescheduling the trip with generous owner flexibility or a full 100% refund of all monies paid with no deduction.
We strongly advise the purchase of CSA trip interruption insurance to indemnify the risk of cancellation, weather delay, airline interruption, medical reason for non-travel, etc.
II. ENTRY & IMMIGRATION REQUIREMENTS
The Cayman Islands is a foreign country and has both entry and immigration requirements in order to enter. Entry into the Cayman Islands requires each person to present a valid passport. Citizens from some countries may require a visa. The Cayman Islands also may require tourists to submit to viral testing (either pre or post-arrival) or require proof of vaccination.
Please check all official government sources for current entry (https://www.gov.ky/) and visa requirements (http://www.immigration.gov.ky).