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.
Guest Reviews of cayman castle & guesthouse
East End , East End
Good Place with Splendid Views
5 out of 5 stars
cayman Castle
5 out of 5 stars
Picture Perfect ??
5 out of 5 stars
My family loved our week staying at this property
5 out of 5 stars
Wish we could have stayed longer!
5 out of 5 stars
Outstanding!
5 out of 5 stars
Awesome Property!
5 out of 5 stars
Wonderful Time Staying at The Castle!
5 out of 5 stars
Better Than Advertised!
5 out of 5 stars
Beautiful Island
5 out of 5 stars
40th Birthday!
5 out of 5 stars
Absolutely Spectacular!
5 out of 5 stars
Enjoyed Our Stay Immensely
5 out of 5 stars
Very Lovely Spot
5 out of 5 stars
Cayman Castle
5 out of 5 stars
Cayman Castle and Guesthouse
5 out of 5 stars
Excellent!
5 out of 5 stars
Perfect Location
5 out of 5 stars
Great Spot - Cayman Castle Guesthouse
5 out of 5 stars
Property Exceeded our Highest Expectations
5 out of 5 stars
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The Concierge & Service Fee includes Guest Services Membership for you and your guests.
Guest Member Benefits
- Complimentary use of snorkel equipment
- 10% Advance Booking Discount for private scuba and snorkel charters
- Guest benefit & discount card for savings at Preferred Vendors
- Jacques Scott Wine & Spirits pre-order & delivery to your villa
- Guest parcel receipt & delivery to your villa
- Centralized on-island Guest Services & Welcome Center
- Personalized itinerary for scheduled events & reservations
- Coordinate special events, private dinners & private transportation
- Referral to preferred vendors, restaurants and watersports
- Fast-Track VIP Airport Arrival through Immigration & Customs (fees apply)
- Arrange private airport pickup and transfer (fees apply)
- Unlimited use of Silver Thatch Fitness Center (18+ yrs.)
- Business Center Access: computers, printer, scanner, & FedEx/DHL supplies
At-Villa Benefits
- Welcome amenity gift basket: Locally-sourced products
- Luxury linens, towels, & robes provided
- Complimentary early check-in or late check-out if no same-day conflict
- Pre-stocking of groceries & beverages prior to your arrival ($75 delivery fee credit)
- Convenience & activity items: baby equipment, snorkel equipment, Apple TVs, rollaway bed
- Hotel grade bath products
- Arrange chefs, cooks, babysitting, massage or family photography services
- $2,500 of Accidental Damage Protection for villa (indoor items/decor)
- Tandem kayaks, single kayaks, Seaview boards & paddleboards available for discounted rental & free delivery*
*Signed waiver required
| Begins | Ends | Daily (before fees & tax) |
|---|---|---|
| Nov 07, 2025 | Nov 07, 2025 | $1,495 |
| Nov 08, 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 | Apr 30, 2027 | $1,750 |
Rate Details
- 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.
Have questions about this property? Email us using the white button below.
