HomeAway uses cookies to improve your site experience. Learn more. By continuing, you consent to our use of cookies.
HomeAway uses cookies to improve your site experience. Learn more. By continuing, you consent to our use of cookies.
check navigate-up navigate-left navigate-right expand

Jim Leavitt

Member since: 2000
Speaks English

7BR-Cayman Castle: Oceanfront Estate with Infinity Pool, Great Snorkeling

15 Reviews
Bedrooms 7
Separate WC's1
Property type villa
Minimum Stay 5 nights

Pay with confidence

Your booking will be backed by our Book with Confidence Guarantee when you complete your reservation online and finalise payment on HomeAway.

Learn more


Photos and Description of this 7 bedroom holiday villa in Cayman Islands - 7BR-Cayman Castle

7 Bedrooms, 7 Baths, Sleeps 18

7BR Luxury Cayman Castle & Guesthouse is directly oceanfront on a private 2-acre gated estate on an elevated point of land and enjoys a large private white-sand beach with excellent snorkeling & sunbathing. Infinity pool, multi-tiered oceanfront terraces, 40' roofed balcony and a covered 1st floor veranda provide guests plenty of room to spread out, dine together or just enjoy the views. (3) thatched palapas, (4) kayaks, pool heater in winter and walking distance to Ocean Frontiers dive shop (as well as 3 lunch spots) make this home a wonderful choice for a larger family. Great snorkel spot 250 yds in front of Castle. This is not barefoot swimming, as there is a marine environment. Cayman Castle also makes a great wedding venue FOR RESIDENT GUESTS ONLY (no invited guests permitted). Custom 18' mahogany & mosaic dining table for large family meals and entertaining. Seats 18 easily .

This grand estate is not only one of the largest rental villas on the entire island; it also is a notable landmark. Virtually anyone on the island will know of the "Castle in East End". Adjacent to the "Wreck of The 10 Sails Park" and police constable's residence; this property enjoys no residential neighbors to the north for 500 feet+ or to the south for 300 feet+. With the gate shut in the evenings; guests enjoy their privacy.

The owner maintains the property quite well; making upgrades every fall to keep the experience not only refreshing and pleasant for the repeat guests as well as for newcomers to Cayman Castle.

Stainless propane BBQ cooking center with granite top, central A/C, (10) lounge chaises, WiFi Internet access. AppleTV, multiple Plasma TVs, Sonos wireless speakers.Plenty of off-street parking.

5BR Castle and 2BR Guesthouse accommodate 18 people (14 adults max.). Guesthouse offers a second private pool, covered oceanfront verandah and additional parking.

All rates INCLUDE Government Occupancy tax.

Mid-week maid service provided.

(3) King Suites, (3) Queen Suites, bunkroom with 2 twins and 2 fulls. The first floor Queen suite offers a private entrance and TV area. Sleeper sofa in the second floor Queen Suite for children. 2 full-sized folding cribs provided.

$2,000 refundable damage deposit waived with purchase of $49 ADP - Accidental Damage Protection.

20% Discount Available Sep - Oct.

Discounts Offered For Multi-Week Rentals.

Weddings limited to guests staying at the house (no invited guests-18 maximum).

Booking Rules:

Minimum Stay:

5 Nights if between Saturdays

Can accommodate longer rentals

Holiday weeks are strictly weekend to weekend

Minimum age of 25 yrs old to lease any of the villas and lessee must occupy the villa during the entirety of the rental period.

Owner requires refundable $250 Excess Cleaning Fee Deposit.

More Details
  • Events Allowed
  • Minimum Age Limit for Renters
  • children welcome
  • non smoking only
  • pets not allowed
Jim Leavitt (Property Manager)
Speaks English

About Jim Leavitt

Owner purchased the condemned hulk of a 2 story castle and 750' of shore in 2002 out of a foreclosure sale. Sold the last 200' of sandy beach to a friend and later sold another 100'; keeping 450' for the estate. Neither owner has built as yet, but he would like the neighbors!

Why Jim Leavitt chose Cayman Islands

The Castle is 24' above sea level and has a commanding 180 degree view of the east end reef, is within walking distance of the best dive shop in the Caribbean (2013) Ocean Frontiers; and had room to install a large infinity pool and 2BR guesthouse. Owner added a story to the Castle as well.

What makes this villa unique

Unique privacy, space and views. The stone patio out on the point offers guests the opportunity to watch for shooting stars at night and observe the kite-boarders and dive boats during the day. Eagle Rays and even the Christmas Manta have been seen in front of the Castle in the shallows.


based on 15 holidaymaker reviews

7BR-Cayman Castle: Oceanfront Estate with Infinity Pool, Great Snorkeling
average rating of 4.733333 based on 15 reviews

Absolutely awesome!

  • 5 of 5

This property was fabulous! The location is private and very quiet which made for a very relaxing vacation. The sunrises and panoramic view was stunning with a constant breeze. Our adult girls loved using the kayaks on the very calm water. The house is well appointed and had more than ample outdoor seating on 5 different levels. The pictures of this property do not do it justice! If you are looking for a quiet, relaxing, gorgeous place to stay, this is it! There are excellent restaurants within a 15 minute drive and a convenience store to pick up groceries. The owner gave us so much information about the property and area we immediately felt at home. LOVED, LOVED, LOVED our time here! Thank you for making it a wonderful stress free vacation!

  • Review Submitted: Mar 24, 2016
  • Date of Stay: Mar 2016
  • Source: VRBO, from HomeAway
Did you find this review helpful?
0 0
Plymouth, MN

Highly recommend

  • 5 of 5

Our trip to the Cayman Castle was incredible. If you value your privacy and space, I don't think you will find a better place on the island. My wife and I, plus our 5 kids aged 9-16, plus my parents in their early 70's stayed at the Castle for one week. There was plenty of space for all of us, and none of us wanted to leave at the end!

There are so many areas to enjoy on the property it was almost hard to find time to enjoy them all within a week. The kitchen is large and very nice to cook in. We found it much more convenient to prepare our own meals than to eat out. We didn't want to leave the house! The house sits on a point and has more than 180 degree views that never get old. The rooms were very comfortable and the house was well decorated.

The property's kayaks were also a huge hit - we used them every day to explore the ocean in front of the house. If you are ambitious, there are some amazing snorkel spots that are a ways out.

We also enjoyed the incredible close proximity of the Ocean Frontiers Dive Shop. We booked snorkeling and diving trips with them, as well as a trip to Sting Ray City. The dive shop is top notch!

We started our trip at the Ritz Carlton on 7 mile beach for one night, then spent a week at the Castle, then spent one more night on 7 mile beach at the Marriott. We found it interesting to compare the hotel style vacation on 7 mile beach with the private home style vacation on the east end. And while the hotels were very nice, they did not compare in any way to our stay at the castle. We want to go back and do it all over again! It was a perfect vacation.

  • Review Submitted: Nov 27, 2015
  • Date of Stay: Oct 2015
  • Source: VRBO, from HomeAway
Did you find this review helpful?
4 0

GRAND Accomodation at Grand Cayman

  • 5 of 5

Our stay at Cayman Castle started out a bit bumpy! (But please read ENTIRE review).

The day before our arrival we were advised of an electrical short at the Cayman Castle, causing all electricity to be out for the weekend. Our entire trip had been planned solely to stay at “The Castle”, so this news was devastating to us! We were advised that we would be put up temporarily at another location for two nights, and promises were made that the problem would be fixed over the weekend. (But we were skeptical that ANY repairs could be done on Saturday & Sunday, and feared our Family Reunion Vacation was ruined! …….we were proven wrong!!!!!).

Our temporary weekend accommodations were somewhat cramped, but VERY NICE (“Two Rainbows” Villa, over at Rum Point). During that time I was stunned to see 5-6 workmen pulling double-overtime on Sat & Sun to repair the problem at The Castle. (It was no minor problem!!!!). And as promised, it was ready for us on Monday! And it was worth the wait! (And for our trouble, we were not only compensated for the difference in price for our temporary 2-day relocation, but also afforded a “dinner on Jim” at the FABULOUS Tukka Restaurant nearby!).

And now, with that out of the way, my REVIEW OF CAYMAN CASTLE: Our family chose The Castle based on the pictures we saw on the website, and the luxury, exclusivity, spaciousness and amenities of the entire property! We were not disappointed. The rooms are fresh, updated and luxurious! The bathrooms are all roomy, modern and beautifully designed. Kitchen is first class and affords all modern conveniences. Linens are fresh, and towels plentiful. But all that is a distant second to the beautiful location of The Castle. The porches, decks and patios overlook some of the prettiest water in the Caymans. There is a fantastic snorkel reef about 200 yards straight away from the Castle’s stairs into the Caribbean. (Use the kayaks provided to row out to underwater heaven. Tie up to the buoy and swim around to see stingray, squid, lobster, starfish and a whole aquarium of colorful fish, just a short paddle away). We also enjoyed sharing the grounds with some fascinating (and large) Iguanas who seemed to join us for coffee each morning on the lower patio. (But don’t worry! They are harmless, and more afraid of you, than you are of them!). The pool and surrounding patio, is not only cool and refreshing, but offers a fantastic setting to wind down at the end of the day! The view over the zero

  • Review Submitted: Jul 21, 2014
  • Date of Stay: Jul 2014
  • Source: HomeAway
Did you find this review helpful?
6 1

family birthday celebration

  • 1 of 5

The castle was great UNTIL it rained. Our family rented the castle & guesthouse. We were in the guesthouse & on our last day water poured in thru the windows & water leaked from the ceiling fan in the center of the room. We spent our last day in Cayman cleaning up large amounts of water dripping from the ceiling fan, kitchen & windows. I would NOT recommend anyone staying there unless this is rectified. We were not told that the place leaked before booking the house. If we knew about the leaks, we may have chosen to stay somewhere else

  • Review Submitted: May 28, 2012
  • Date of Stay: May 2012
  • Source: VRBO, from HomeAway
Owner's Response: This large family stayed for two weeks...and enjoyed great weather until day #9 when the heavens opened (tropical storm Beryl formed over top of Grand Cayman). Cayman had record rainfall of 13" in 2 days(!!) and it rained sideways..the schools closed and government buildings shut down. The Castle & Guesthouse are in east end and the rain & wind came from the east..so it was sideways against the sliding doors and windows and leaked under the sliders-- the guests used towels to soak up rainwater--and we sent out maids to do the towels for them. We also had a roof drain blocked which caused a ceiling leak--so our roofer and contractor went over and unplugged that clog..so the kitchen roof stopped leaking. We also caulked the doors...It was just a rotten final 5 nights in Cayman for this family...so I offered to send them to the Lighthouse Restaurant for dinner ($1,000 limit) even though the second week I discounted for them almost 30%. They didn't accept the offer...and only after they left the island, posted this abysmal review of the house (1 star?) AND demanded a refund. I did what I could do for them while on island and offered a nice dinner as a kind gesture of condolence for the weather. There is just no way to please everyone. I am sure they will want to submit more negative reviews. Please read the 5 years of good reviews and understand that some people can never be happy when the weather turns bad like it did. 13" of rain is almost half the annual rainfall for the east end historically!! CORRECTIVE ACTION: I flew down as soon as they left..hired a roofer and contractor and completely removed the second floor roof and re-sloped the decking, installed a new membrane and drains...we also siliconed around the sliding glass doors--but in a 30mph 1"/hr sideways rainstorm...sliding door tracks will spill over...I am glad that we only have 1-2 of these storms a year.
Did you find this review helpful?
47 7
Lakeville, Massachusetts

Cayman Castle

  • 5 of 5

The stay at the "Castle" was outstanding. (We rented the castle and guesthouse) It was March of 2009 and it was our chance to bring family and friends together in one great location. Our kids; grandchildren and friends enjoyed the spacious accommodations that allowed all of us the opportunity for both privacy and socialization. The rooms were comfortable and the location great for water sports (swimming (ocean and heated pool), kayaking, snorkeling and kite surfing!) We have been renting in the Caribbean since 2002 and without question Jim offers the most personalized of services. PS: My grandson, now nine, has a goal to one day buy the castle, top that for a recommendation! Bill from Massachusetts

  • Review Submitted: Sep 12, 2011
  • Date of Stay: Mar 2009
  • Source: VRBO, from HomeAway
Did you find this review helpful?
18 0
Washington DC


  • 5 of 5

I spent my honeymoon at the Castle and Guest House in 2008 (Hurricane Paloma) ...we had all ages and mobilities of folks staying - the week was ideal - so easy for an 89 year old to enjoy ... and safe for the little ones .... Hurricane (Cat 3+) did not even touch us - round castle and watertight ... amazing ... The ad understates the experience you will have - The exclusive location of this heaven keeps us coming back (5 trips so far) ... the staff at the dive place next door are incredibly helpful - nice to be able to walk there! and to Vivine's Kitchen!! And some of the best snorkeling is a swim from the personal dock - Also, close to Rum Point, and Kaibo - wonderful wonderful vacation spot - all the amenities with the requisite 'turn off button' from crazy East Coast lives .... HIGHLY RECOMMENDED

  • Review Submitted: Sep 9, 2011
  • Date of Stay: Oct 2008
  • Source: VRBO, from HomeAway
Did you find this review helpful?
8 0


Nearest Airport
22 Miles
Owen Robeerts (GCM)
Nearest Barpub
250 Metres
Eagle Rays
Nearest Restaurant
1 Miles
Car: necessary

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 www.thereef.com and www.morritts.com 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


Prices & Availability

Enter dates to see total
Enquire Now
Available arrival


Accommodation and facilities for this holiday villa on Cayman Islands on Caribbean

Property Type:
  • villa
  • Self-catering
Floor Area:
  • 7000 sq. ft.
Location Type:
  • Beachfront ...
  • Oceanfront ...
  • Away From It All
  • Family
  • Romantic
  • Sports & Activities
  • Air Conditioning
  • Clothes Dryer
  • Hair Dryer
  • Internet
  • Iron & Board
  • Linens Provided
  • Living Room ...
  • Parking ...
  • Telephone
  • Towels Provided ...
  • Washing Machine
  • Coffee Maker ...
  • Dishes & Utensils
  • Dishwasher ...
  • Kitchen ...
  • Microwave
  • Oven ...
  • Pantry Items ...
  • Refrigerator ...
  • Hob
  • Toaster
  • Dining ...
  • Dining Area
  • seating for 14 people
  • 7 Bathrooms
  • 1 Separate WC
  • 1st Floor Powder Room - Toilet , Foyer located Powder Room
    1st Floor Queen Ensuite - Toilet , Shower Enclosure , Glass Block Shower and Granite Counters European Sinks
    3rd Floor King Ensuite - Toilet , Shower Enclosure , Glass Block Shower and Granite Counters European Sinks
    2nd Floor King Ensuite - Toilet , Shower Enclosure , Glass Block Shower and Granite Counters European Sinks
    2nd Floor Queen Ensuite - Toilet , Shower Enclosure , Glass Block Shower and Granite Counters European Sinks
    GH King Ensuite - Toilet , Shower Enclosure , Glass Block Shower and Granite Counters European Sinks
    GH Queen Ensuite - Toilet , Shower Enclosure , Glass Block Shower and Granite Counters Two Sink areas
    Outdoor Pool Shower - Shower Enclosure , Hot/Cold Water Shower by Pool Area
  • 7 Bedrooms, Sleeps 18
  • Bunk Room - 2 Double Bed , 2 Single Bed , Full over Full and Twin over Twin. 50' Plasma TV for movies
    3rd Floor Honeymoon King Suite - 1 Extra Lg. Double Bed , Ensuite Bathroom with 40' LCD Sat. TV and Apple TV, Porch
    2nd Floor King Suite - 1 Extra Lg. Double Bed , Ensuite bathroom glass block shower with granite counters
    Guesthouse King Suite - 1 Extra Lg. Double Bed , Oceanfront King Ensuite with Glass Block Shower & Sat. TV
    Guesthouse Queen Suite - 1 Large Double Bed , 2 Single Bed , GH Queen Suite with BUnks for children, ensuite bathroom
    2nd Floor Queen Suite - 1 Large Double Bed , 1 Sofa bed/Futon , Queen ensuite with Pull Out Sofa, Glass Block Shower/Granite
    1st Floor Private Queen Suite - 1 Large Double Bed , Ensuite with private entrance, 40' LED Sat. TV and Bathroom
  • Books
  • DVD Player
  • Games
  • Satellite / Cable
  • Stereo
  • Television ...
  • Toys
  • Balcony ...
  • Terrace ...
  • Kayak / Canoe ...
  • Barbecue
  • Events Allowed
  • Minimum Age Limit for Renters ...
  • children welcome
  • non smoking only
  • pets not allowed
Pool / Spa:
  • Heated Pool
  • Private Pool
Onsite Services:
  • Chauffeur
  • Concierge
  • Massage
  • Private Chef
  • botanical garden
  • caves
  • churches
  • duty free shops
  • festivals
  • marina
  • museums
  • reefs
  • restaurants
Leisure Activities:
  • beachcombing
  • eco tourism
  • horse riding
  • paddle boating
  • photography
  • scenic drives
  • sight seeing
  • walking
Local Services & Businesses:
  • ATM/bank
  • Babysitter
  • groceries
  • hospital
  • massage therapist
  • medical services
Sports & Adventure Activities:
  • deepsea fishing
  • fishing
  • fly fishing
  • golf
  • golf pass optional
  • hiking
  • jet skiing
  • paragliding
  • pier fishing
  • sailing
  • diving
  • snorkelling
  • caving
  • swimming
  • water skiing
  • wind-surfing

Partner Offers

Portable wifi hotspot

You might like these similar properties