110 people have viewed this property this week.

Cayman Castle & Guesthouse

East End
20 Guests
7 Bedrooms
7.5 Bathrooms

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.

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)

  • 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.
  • Bunk Suite – lower-level, full-over-full bunk beds, television with Apple TV, 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

Oceanfront
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
Beach Cabana
Satellite TV
Stereo
4 Apple TVs
Central A/C
Washer/Dryer
Dishwasher
Keurig & Drip Coffee Makers
Ice Coolers
Beach & Bath Towels Provided
Hair Dryers
Additional Kayaks for Rent
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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.

 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
  • 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
  • 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 15 user reviews

Outstanding!


         
Review by Joy on 03/19/2024
5 out of 5
The Cayman Castle and guest house were outstanding! We were a large group (19) and had plenty of room to spread out and have privacy if wanted. The great room, kitchen and outside patio area were very big and we did not feel crowded at all when all together. The views were fantastic and the facility extremely clean. My only thought for anyone that wants to spend time at 7 mile beach and Georgetown restaurants (I didn\'t) is that it is a bit of a drive, but for me I loved the fact it was in a quiet area without the crowds of the populated side of the island. There were a few restaurants close to the castle that were great! We took advantage of having the house pre-stocked with groceries and also used one of their recommended chefs one night. Check in and any contact we had with the management company was seamless. We will be back!

Awesome Property!


         
Review by Cayman Crew 2024 on 02/26/2024
5 out of 5
We had a beautiful time at the Cayman Castle and Guesthouse. Property was exactly as advertised. Clean and well maintained. Cayman Villas staff did a superb job in attending to our requests and needs. Very enjoyable stay and we plan to do it again at the Castle! Love East End Grand Cayman.

Wonderful Time Staying at The Castle!


         
Review by Sue on 02/12/2024
5 out of 5
We had a wonderful time staying in the castle! We had 8 adults and 2 children. There was plenty of space for everyone. The views are spectacular! We especially loved the shady, comfortable area around the pool where we spent a lot of our time. The beach was beautiful and also had great shade and chairs under a new wooden palapa. We really enjoyed snorkeling especially around the first buoy nearest the house. I'd recommend this home to everyone!

Better Than Advertised!


         
Review by Lesa on 01/13/2024
5 out of 5
Our group had 15 people ranging in age from 5 months to 75 years old. The property is even better than advertised. We never felt cramped or lacked for any room. The Castle and guest house are wonderfully stocked with lot of towels and any kitchen gadget you would need. Lots of books, games, puzzles, pool toys and kayaks. A wonderful place to spend our anniversary with 4 generations of our family. We would love to come back some day.

Very Lovely Spot


         
Review by The Stricklands on 12/06/2023
5 out of 5
The house is in a very lovely spot. The ocean views are amazing, even the stars are spectacular at night. The sun shining in the window in the morning letting us know it's time to awake to another wonderful day on the island. We enjoyed pizza from the Italian Kitchen. It is delicious. La Casita was also wonderful for dinner. Over The Edge- fried chicken- best on the island. Sorry to leave the island but we will be back again. Leaving with fond memories. 

Enjoyed Our Stay Immensely


         
Review by The Smiths on 12/06/2023
5 out of 5
We have enjoyed our stay immensely. The views from the veranda are beyond compare. The private beach is made for total relaxation and book reading. There is nothing we can think of that would have made it better. Many eateries very close that were great. We highly recommend the Italian Kitchen, La Casita, and The Czech Inn Grill(fantastic burgers). Owner is very entertaining!

Absolutely Spectacular!


         
Review by The Donovans on 12/06/2023
5 out of 5
Absolutely spectacular! We loved every moment spent in this hidden gem. Until next time...

40th Birthday!


         
Review by Iowa Friends on 12/06/2023
5 out of 5
Partied like rockstars for my 40th!! Starfish point is great. Tukka has excellent food. Snorkeling at Rum Point(big coral perpendicular to dock). Don\'t miss Stingray City!

Beautiful Island


         
Review by The Chester Family on 12/06/2023
5 out of 5
Beautiful island. Beautiful people. Wonderful place for family. Reunion-vacay!

Cayman Castle


         
Review by Michael on 11/29/2023
5 out of 5
Awesome place great views. Great time. Loved eastern side of the island. Better than pictures.

Cayman Castle and Guesthouse


         
Review by Michael on 07/02/2023
5 out of 5
Awesome place great views. Great time. Loved eastern side of the island. Better than pictures.

Excellent!


         
Review by Ramona on 04/03/2023
5 out of 5
Exceeded expectations! Excellent location. Quiet east end of island. Snorkeling by the barrier reef was some of the best on the island. Several restaurants & bars within walking distance. House was perfect for our group of 18 spanning 3 generations. We loved the Cayman Castle!

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
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    Available     Unavailable  Check-In Only  Check-Out Only

Begins Ends Daily
Apr 06, 2024May 24, 2024 $1,750
May 25, 2024Aug 14, 2024 $1,950
Aug 15, 2024Nov 01, 2024 $1,495
Nov 02, 2024Nov 22, 2024 $1,950
Nov 23, 2024Nov 30, 2024 $2,350
Dec 01, 2024Dec 18, 2024 $2,050
Dec 19, 2024Dec 26, 2024 $3,895
Dec 27, 2024Jan 03, 2025 $4,295
Jan 06, 2025Mar 01, 2025 $2,350
Mar 02, 2025Apr 12, 2025 $2,450
Apr 13, 2025May 24, 2025 $1,750
May 25, 2025Aug 14, 2025 $1,950
Aug 15, 2025Nov 01, 2025 $1,495
Nov 02, 2025Nov 22, 2025 $1,950
Nov 23, 2025Nov 30, 2025 $2,350
Dec 01, 2025Dec 18, 2025 $2,050
Dec 19, 2025Dec 26, 2025 $3,895
Dec 27, 2025Jan 03, 2026 $4,295
  • 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.
  • A refundable damage deposit is required for all stays.
  • Refundable damage deposits will be returned to the guest 7 days after departure pending any damages.
  • We accept Visa, MC, Discover, and Bank Wire for payments. 

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.

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 Budget CaymanAvis, or Marshalls.

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