Cayman Castle & Guesthouse
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 ocean 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.
Sleeping Arrangements
(Sleeps 16 guests total, 12 adults max)
- Primary Suite – spans entire third-floor, ocean views, king bed, private balcony, television, small dining nook, ensuite with shower.
- South Suite – second-floor, ocean views, king bed, small workstation, ensuite with shower.
- Family Suite – second-floor, king bed + bunk beds, ensuite with shower.
- Pool Suite – lower level, queen bed, ocean views, private entry, walk-out access to the pool deck, television, ensuite with shower.
- Guesthouse Suite #1 – king bed, ocean views, desk, large chairs, ensuite with walk-in shower.
- Guesthouse Suite #2 – queen bed + bunk beds, ocean views, ensuite with dual vanities and shower.
Cayman Castle & Guesthouse 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.
- 500 feet of shoreline, 200 feet is sandy beach. Step off our driveway onto white sand!
- Large Beach Cabana, 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.
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 & 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, and 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 added due to enhanced cleaning and sanitation.
**Additional tandem kayaks are available for discounted rental. A signed waiver is required.
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Amenities
 Your Concierge & Service Fee includes your Guest Services Membership.
Member Benefits
- Centralized on-island Guest Services & Welcome Center
- Unlimited use of Private Fitness Center (18+ yrs.)
- Business Center Access: computers, printer, scanner, & FedEx/DHL supplies
- Proprietary Guest benefit & 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
- Hotel grade 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
- Tandem kayaks available for discounted rental*
*Signed waiver required.
Guest Reviews of Cayman Castle & Guesthouse
East End , East Endstars based on 20 user reviews
Good Place with Splendid Views
cayman Castle
Picture Perfect ??
My family loved our week staying at this property
Wish we could have stayed longer!
Outstanding!
Awesome Property!
Wonderful Time Staying at The Castle!
Better Than Advertised!
Beautiful Island
40th Birthday!
Absolutely Spectacular!
Enjoyed Our Stay Immensely
Very Lovely Spot
Cayman Castle
Cayman Castle and Guesthouse
Excellent!
Perfect Location
Great Spot - Cayman Castle Guesthouse
Property Exceeded our Highest Expectations
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| Begins | Ends | Daily (before fees & tax) |
|---|---|---|
| Nov 11, 2025 | Nov 21, 2025 | $1,950 |
| Nov 22, 2025 | Nov 30, 2025 | $2,350 |
| Dec 01, 2025 | Dec 18, 2025 | $2,050 |
| Dec 19, 2025 | Dec 26, 2025 | $3,895 |
| Dec 27, 2025 | Jan 03, 2026 | $4,295 |
| Jan 04, 2026 | Feb 28, 2026 | $2,350 |
| Mar 01, 2026 | Apr 11, 2026 | $2,450 |
| Apr 12, 2026 | May 22, 2026 | $1,750 |
| May 23, 2026 | Aug 13, 2026 | $1,950 |
| Aug 14, 2026 | Oct 30, 2026 | $1,495 |
| Oct 31, 2026 | Nov 20, 2026 | $1,950 |
| Nov 21, 2026 | Nov 29, 2026 | $2,350 |
| Nov 30, 2026 | Dec 17, 2026 | $2,050 |
| Dec 18, 2026 | Dec 25, 2026 | $3,895 |
| Dec 26, 2026 | Jan 03, 2027 | $4,295 |
| Jan 04, 2027 | Feb 27, 2027 | $2,350 |
| Feb 28, 2027 | Apr 10, 2027 | $2,450 |
| Apr 11, 2027 | May 04, 2027 | $1,750 |
- 13% Occupancy Tax added to all rates.
- 12.90% Villa Concierge & Service Fee added to all rates.
- A Departure Cleaning Fee is required for all stays.
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.








