
Cayman Castle & Guesthouse
- Overview
- Amenities
- Calendar
- Rates
- Guest Services
- Beach Notes
- Map
- Reviews
- Floor Plan
- Virtual Tour
- Book Now
Cayman Castle and Guesthouse sits directly oceanfront on a private 2-acre walled estate. Perched on an elevated point of land, the Cayman Castle grounds include an attached private white sandy beach with excellent snorkeling and sunbathing. Infinity pool (heated in the winter), multi-tiered oceanfront terraces, panoramic roofed balconies, and a covered first-floor veranda provide guests plenty of room to spread out, share meals, or enjoy the stunning vistas.
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 is 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, this property enjoys no residential neighbors to the north or south for a good 500 feet in either direction. With the Castle's gate shut in the evenings, guest can enjoy their privacy.
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, and an ensuite bathroom with a spacious walk-in shower
- Second Floor Guest Suite #1 – King suite with ocean views, couch, desk, chair, and an ensuite bath with a walk-in shower
- Second Floor Guest Suite #2 – Queen suite with ocean views, a couch, and an ensuite bath with a walk-in shower
- First Floor Suite – Queen suite with ocean views, doors to the pool deck, a sitting area, TV, and an ensuite bath with a walk-in shower
- First Floor Bunk Suite – Bunk bed suite with two full over full bunks, a TV, and an ensuite bath with a brand new walk-in shower
- Guesthouse Suite #1 – Oceanfront king suite with stunning views, desk, large chairs, and an 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 an ensuite bath with a 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), 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, and walking distance to Ocean Frontiers dive shop, 3 restaurants make this home a convenient choice for larger families.
- 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 Adirondack chairs 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—we ask that you wear pool shoes or fins when you go exploring!
- Stainless steel propane grill and prep area with granite countertops.
- Wide driveway with plenty of off-street parking for guests.
- Lounge chaises and outdoor sectionals on pool decks, porches, and balconies for guests to relax in style.
- Multiple roofed verandas at both Castle & Guesthouse provide guests protection from the sun and rainstorms.
INDOORS
- Kitchen, dining, and living area are all oceanfront on the second floor, offering lovely views through the multiple sliding glass doors that lead to the main level porch and outdoor dining area.
- The full modern kitchen features double ovens, dishwasher, new SubZero 48" refrigerator, stovetop, microwave, Keurig coffeemaker, Kitchenmaid mixer, multiple coffeemakers, blenders, tons of counter space, and bar seating for 6-8.
- Indoor dining seating for 6-8.
- Comfortable living area with 60" flat screen TV for unwinding after a day of sun and surf.
- Back-up full-sized fridge with icemaker in Laundry.
- Serving bar with wine fridge adjacent to the lower level pool deck.
Castle Guesthouse Unique Features
- Full modern kitchen refrigerator, dishwasher, stove, oven, microwave, blender, and coffeemaker.
- Comfortable sectional sofa with large flatscreen TV & Bose speaker bar.
- 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, plus indoor and outdoor Bluetooth speakers. The kitchens are stocked with dishes, glasses, cookware, and utensils. Linens, towels, and beach towels are also provided for guests.
*Note: Additional Silver Thatch tandem kayaks available for discounted rental. Signed waiver and 5-day minimum required with 6th and 7th day free: US$39 per day per kayak ($195 per week/each). Paddles included.
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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 service fee is capped at seven 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
- $150 discount towards a Silver Thatch stingray/snorkel 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 and 5 day minimum required with 6th and 7th day free, paddles included: US$39 per day per kayak ($195 per week/each).
Guest Reviews of cayman castle & guesthouse
442 Austin Connally Drive Grand Cayman ,
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
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Begins | Ends | Daily | Weekly | Monthly |
---|---|---|---|---|
Dec 01, 2019 | Dec 18, 2019 | $1,695 | ||
Dec 19, 2019 | Dec 26, 2019 | $2,895 | ||
Dec 27, 2019 | Jan 05, 2020 | $3,295 | ||
Jan 06, 2020 | Mar 06, 2020 | $1,995 | ||
Mar 07, 2020 | Apr 14, 2020 | $2,195 | ||
Apr 15, 2020 | May 29, 2020 | $1,595 | ||
May 30, 2020 | Aug 21, 2020 | $1,795 | ||
Aug 22, 2020 | Nov 06, 2020 | $1,295 | ||
Nov 07, 2020 | Nov 20, 2020 | $1,595 | ||
Nov 21, 2020 | Nov 28, 2020 | $1,895 | ||
Nov 29, 2020 | Dec 18, 2020 | $1,695 | ||
Dec 19, 2020 | Dec 25, 2020 | $2,895 | ||
Dec 26, 2020 | Jan 05, 2021 | $3,295 | ||
Jan 06, 2021 | Mar 05, 2021 | $1,995 | ||
Mar 06, 2021 | Apr 16, 2021 | $2,195 | ||
Apr 17, 2021 | May 28, 2021 | $1,595 | ||
May 29, 2021 | Aug 20, 2021 | $1,795 |
- 13% Occupancy Tax added to all rates
- 10% Guest Service Fee includes your Silver Thatch Membership
- Guest Service Fee is capped at 7 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.
- Inquire for shorter stays if calendar suits.
- Discounts offered for multi-week stays.
- Must be 25 years or older to book, and must occupy the home during the entire stay.