On The Rocks

7 Bedrooms 4 Bathrooms 14 Sleeps Grand Cayman

Welcome to On The Rocks. This oceanfront gated estate is conveniently located 20 minutes from the airport in the planned residential community of Beach Bay. 


The dozen or so homes along this rugged coastline share a key neighborhood amenity: a wonderful sandy beach cove, with protected swimming and excellent snorkeling, just 5 minutes from the villa! Our guests report seeing lobster, octopus, and teeming juvenile fish along the coral heads.


Architecturally, the design and flow of the house is low-country plantation-style with elevated ocean views throughout, a wrap-around veranda, and a central great room with walk-out access to a private freshwater pool.


There is an enormous driveway for parking and a garage with an optional guest suite above.


The main 6-bedroom, 3-bathroom villa features a wrap-around veranda that provides a full-day respite from the Caribbean sun with shaded areas for a good read, morning yoga sessions, breakfast, or sunset viewings. 


The freshwater pool has a wide sundeck with lounge chaises as well as a gazebo for al fresco dining by the sea. A zoysia grass lawn feels cool on bare feet and the estate has many mature palm trees for additional shade.


Sleeping Arrangements
(Main Villa Sleeps 12 Guests.
Main Villa + Guest Suite Sleeps 14 Guests.)



  • Primary Suite: upper-level, king bed, ocean views, television, walk-out access to a private balcony, ensuite bathroom with deep soaking tub and separate shower.

  • Bedroom #1: upper-level, four poster queen bed, ocean views, desk + chair, shares upper-level hall bathroom equipped with a shared bath.

  • Bedroom #2: upper-level, two twin beds, garden views, shares upper-level hall bathroom equipped with a shower bath.

  • Bedroom #3: upper-level, queen bed, garden views, shares upper-level hall bathroom equipped with a shower bath.

  • Bedroom #4: lower-level, queen bed, ocean views, television, walk-out access to the pool deck, shares connected bathroom equipped with a shower bath.

  • Bedroom #5: lower-level, queen bed, shares connect bathroom equipped with shower bath. 

  • Optional Guest Suite: detached and above the garage with air conditioning, kitchenette, living and dining area, television with AppleTV + Xbox 360, queen bed, and bathroom with shower. 


The optional guest suite is ideal for those who prefer to be under separate roofs from the rest of the group—nannies, teenagers, in-laws, snoring uncles, etc. 


Key Features


LOWER LEVEL



  • The great room is furnished with plush sofa seating, a large cable television, plus ocean views with walk-out access to the pool deck.

  • A gourmet kitchen is stocked with modern appliances including cookware, flatware, glassware, and cutlery.

  • The oceanside veranda is furnished with outdoor dining tables seating 12 guests, plus a lounge area with patio seating. 

  • Gazebo dining table seats 4 with oceanfront views. 

  • Large full laundry room directly off the kitchen.


UPPER LEVEL



  • Enormous oceanfront primary suite with walk-out access to a private furnished balcony. 

  • A second den with cable television, Apple TV, and a DVD player

  • 2 queen bedrooms and 1 twin bedroom all share one hall bathroom equipped with a shower bath. 


With heavy landscaping on both sides of the property, On The Rocks provides guests with enhanced privacy and quiet enjoyment throughout their stay. 



^Reduced rates are offered to small groups not requiring all bedrooms. See Rates tab for pricing.


*Note: A Cleaning Fee is included due to enhanced cleaning, sanitation, and inspection protocols.


**Silver Thatch tandem kayaks available for discounted rental. Signed waiver required. 

  • Gated & Walled Estate
  • Oceanfront Villa
  • Private Freshwater Pool
  • Poolside Cabana
  • Veranda
  • Wrap-Around Porch
  • 4 Zone Central A/C
  • WiFi/Internet
  • Keyless Entry
  • Flat Screen TVs
  • Cable TV
  • Apple TV
  • DVD Player
  • Gourmet Kitchen
  • Modern Appliances
  • Propane Grill
  • Home Security System
  • Guest Deposit Safe
  • Washer/Dryer
  • Beach & Bath Towels Provided
  • Linens Provided
  • Off-Street Parking
  • No Smoking Permitted
  • No Pets Allowed
  • Kayaks for Rent
LEAVE A REVIEW
August 8, 2023 - Website

Wonderful Vacation Home

by Claudio Ortiz Family
On The Rocks was a wonderful vacation home for my family of 8. The house was very comfortable, the rooms, kitchen, and pool. Its location on the island was also great for excursions. Many thanks to Penni and the cleaning staff for being so helpful and welcoming!
August 8, 2023 - Website

Beautiful Home!

by Buckley Family
We had a great time at On The Rocks! Kids and adults played in the pool, gathered n the kitchen and at the table, and watched the sunsets and quick storms from the patio. We loved it and appreciate the opportunity to enjoy Cayman from this beautiful home. Thank you!
August 7, 2023 - Website

Highly Recommend!

by Isalys
My family and I had an amazing time at “On the Rocks”. We enjoyed the peaceful surroundings, clean beautiful comfortable home and wonderfully manicured outdoor space. Everyone had plenty of room and the common spaces were wonderful for a large family; plenty of seating and gathering space. It’s location on the island was perfect for us; right in the center of the island, quiet and within driving distance to all touristy activities. They cleaning crew and manager, Penni, were wonderful and welcoming. I highly recommend the home for a relaxing get away with a large group.
November 28, 2022 - Website

Better Than Expected!

by Laura
Our multi-generational family of 10 spent 7 glorious days at On the Rocks in Grand Cayman. The property is better than the pictures suggest. Upon opening the front door, we were struck with the beauty of the ocean view - straight through the large family room , overlooking the pool and patio area. There are multiple, spacious seating areas throughout the house. The second floor family room became a favorite with the teens. The kitchen has more than enough pots, pans, dishes, and glassware to make cooking and dining in a joy. We found the furniture was not only lovely to look at, but comfortable to sit on. We appreciate the great customer service we received and the spectacular week we spent in Grand Cayman.
July 12, 2022 - Website

Will Be Back!

by John
Wonderful home, loved it! See you in December.
July 12, 2022 - Website

Once in a Lifetime Destination

by Josh
On the Rocks will be our \"Once in a Lifetime\" vacation destination. We hope to return soon! Thank you for the island experience.
March 29, 2022 - Website

Couldn’t Have Been Happier

by Grandma, her children and grandchildren

From the mesmerizing view and sound of the surf to the amenities in the villa, On the Rocks provided a stress-free and relaxing 8 days on Grand Cayman. The villa was spotless, and everything we needed was there. It was the most well-equipped and cleanest kitchen we ever had in the Caymans. We spent lots of time enjoying the pool and the nearby snorkel beach. We also loved the proximity to other snorkeling spots and to the grocery stores. Our family goes to Grand Cayman for carefree relaxation — and On the Rocks made that wish come true.

February 4, 2020 - Website

Again and again!

by Rocco
I think that November 2019 was our 5th year in a row at On the Rocks says it all!
November 9, 2019 - Website

A great house

by Tina
We rented this house with friends and had a magnificent time. When you walk in it is like being in paradise the house is immaculate and the pool overlooking the ocean absolutely breathtaking anytime of the day. The amenities were perfect and I like that we were not in the main stream noise and traffic. I hope we Visit again soon. This is a hard place to leave from to go home.
September 25, 2019 - Website

Tranquility

by Yvette
Although our stay was only 6 nights, the time was special to celebrate family and just get together for a while. Recharge and reenergize. On the Rocks was a beautiful home, everything looked new inside! The pool deck was a great gathering pot. The views were sensational. We recommend this property and will return another time.
May 18, 2019 - Website

Family vacation and birthday celebration

by Phil & Lucienne
Our stay at on the rocks was a combination of birthday celebration for my wife and a family vacation for our four adult children spouses and grandchildren. The stay at this villa was absolutely fantastic. We had outstanding weather the entire time, the pool was very well use throughout the week and it was wonderful to Visit the variety of wonderful beaches on the island. We mixed in some golf, a lot of sightseeing, and wonderful dining at a variety of small and large restaurants. We would highly recommend this place to any and all of my friends thank you very much for the gracious on-site assistance from Penni she was fantastic.
May 10, 2019 - Website

Great Accommodations and Amenities

by Phil
We absolutely adored the house. We loved the accommodations and amenities of On the Rocks! A truly beautiful place. Everything you need is here in the house! The hosts were amazing!
May 10, 2019 - Website

Wonderful Time

by Tony

We had a wonderful time! "On the Rocks" is a beautiful home and comes with a magnificent view. Thank you for the memories. Cheers!

Thank you! Please come back soon!

April 4, 2019 - Website

Amazing property

by Soo
The house was fabulous. Great views, lots of space and privacy for a large group and an amazing master bedroom and bathroom. The pictures online don’t it justice.
April 2, 2019 - Website

Beautiful and Protected!

by SJ
The house was amazing! Lots of space and privacy for a large group. Well equipped, beautifully furnished and accommodating.
February 25, 2019 - Website

On The Rocks is Special

by Anonymous

We had a wonderful time during my stay with Grand Cayman Villas at ON THE ROCKS for 11 nights. The house was spacious, comfortable, and beautiful situated. It was stocked with everything we needed inside and out, to enjoy our time there. Penni Bell, who was our on island manager, was great to work with. She was very helpful to my family. W This house is really private. The small swimming beach down the road was really useful, and safe for kids because of the breakwater. It still seems to be under some ongoing construction, though. Hopefully that will conclude at some future date, because I would use the house and the managers again. Please thank everyone on my behalf

February 4, 2019 - Website

Nice Stay

by J
First off, booking through this property management group was wonderful. They were very accommodating, worked with us when we had a few members of our group drop out, and went out of their way to make us feel comfortable traveling with small children. They delivered all of the pack n plays and high chairs without charge and everything was there upon our arrival. The house itself was beautiful with a very relaxing backyard and lovely pool. Bedroom setup was perfect for our group (4 couples each traveling with one small child). The location of the house was centrally located and equidistant from both Seven Mile Beach and Rum Point. Penni was very quick to respond when we had an issue with the hot water and got it fixed ASAP. The only drawback was the beach within walking distance from the house wasn’t exactly wonderful as described. If you’re looking for a beach to walk to daily (as we were hoping to with all of the kids) then this house might not be for you, but if you’re okay with a bit of a drive, then this house is great! All said and done I would definitely book with this group again, they were amazing!
January 20, 2019 - Website

2 Weeks in Paradise

by MJ
On The Rocks is a beautiful home with a stunning oceanfront view. The beach is a short walk away at the end of the street. We loved the neighborhood and the elevation. We had many family members visit for days during our stay. Family time! We ventured out to several other beaches as well - Rum Point, 7 Mile Beach, Heritage Beach, but Spotts Beach was our favorite. Thank you to Grand Cayman Villas for recommending beaches, snorkel sites, restaurants and activities. George with Silver Thatch Charters was our highlight of the trip. Two weeks flew by. We will be back and recommend the home to others. MJ
January 20, 2019 - Website

Fantastic Property

by Ellen
We searched for a while for the perfect home for our family and could not be happier with our choice! Not too far from George Town, 7 Mile Beach, grocery and many restaurants. But also private and away from the crowds. We recommend On The Rocks to anyone considering a stay here! Thank you for sharing your wonderful property.
January 20, 2019 - Website

Christmas in Cayman

by S.P.
We spent a wonderful Holiday at On the Rocks with our extended family of 8 adults and 5 children. The home is very large and there was plenty of room for everyone. Great quiet time and great family time. The beach is a walk down the street which was not an issue for us. We are used to staying on hillside homes on St John and St Thomas. This was a special treat being oceanfront. The locals are wonderful and helpful. The rental company was great. We did use the fitness center twice and were very happy with the assortment of workout options. Penni met us upon arrival and could not have been nicer. We will be back!
June 22, 2018 - Website

Amazing Vacation!!

by BR
The home was stunning, meticulously clean and well appointed. Everything we could have needed or wanted was available. The pool was beautiful.....our family enjoyed it every day ☀. Thank you to the staff as well for making this an unforgettable family vacation!
September 2023
S M T W T F S
          01 02
03 04 05 06 07 08 09
10 11 12 13 14 15 16
17 18 19 20 21 22 23
24 25 26 27 28 29 30
October 2023
S M T W T F S
01
$
 02
$
 03
$
 04
$
 05
$
 06
$
 07
$
08
$
 09
$
 10
$
 11
$
 12
$
 13
$
 14
$
15
$
 16
$
 17
$
 18
$
 19
$
 20
$
 21
22 23 24 25 26 27 28
$
29
$
 30
$
 31
$
        
November 2023
S M T W T F S
      01
$
 02
$
 03
$
 04
$
05 06 07 08 09 10
$
 11
$
12
$
 13
$
 14
$
 15
$
 16
$
 17
$
 18
$
19
$
 20
$
 21
$
 22
$
 23
$
 24
$
 25
$
26
$
 27
$
 28
$
 29
$
 30
$
    
December 2023
S M T W T F S
          01
$
 02
$
03
$
 04
$
 05
$
 06
$
 07
$
 08
$
 09
$
10
$
 11
$
 12
$
 13
$
 14
$
 15
$
 16
$
17
$
 18
$
 19
$
 20
$
 21
$
 22
$
 23
$
24
$
 25
$
 26
$
 27 28 29 30
31            
January 2024
S M T W T F S
  01 02
$
 03
$
 04
$
 05
$
 06
07 08 09 10 11 12 13
14 15 16 17 18 19 20
$
21
$
 22
$
 23
$
 24
$
 25 26 27
28 29 30 31
$
      
February 2024
S M T W T F S
        01
$
 02
$
 03
$
04
$
 05
$
 06
$
 07
$
 08
$
 09
$
 10
$
11 12 13 14 15 16 17
$
18
$
 19
$
 20
$
 21
$
 22
$
 23
$
 24
$
25
$
 26
$
 27
$
 28
$
 29
$
    
March 2024
S M T W T F S
          01
$
 02
$
03
$
 04
$
 05
$
 06
$
 07
$
 08
$
 09
$
10
$
 11
$
 12
$
 13
$
 14
$
 15
$
 16
$
17
$
 18
$
 19
$
 20
$
 21
$
 22
$
 23
$
24 25 26 27 28 29 30
$
31
$
            
April 2024
S M T W T F S
  01
$
 02
$
 03
$
 04
$
 05
$
 06
$
07
$
 08
$
 09
$
 10
$
 11
$
 12
$
 13
$
14
$
 15
$
 16
$
 17
$
 18
$
 19
$
 20
$
21
$
 22
$
 23
$
 24
$
 25
$
 26
$
 27
$
28
$
 29
$
 30
$
        
May 2024
S M T W T F S
      01
$
 02
$
 03
$
 04
$
05
$
 06
$
 07
$
 08
$
 09
$
 10
$
 11
$
12
$
 13
$
 14
$
 15
$
 16
$
 17
$
 18
$
19
$
 20
$
 21
$
 22
$
 23
$
 24
$
 25
$
26
$
 27
$
 28
$
 29
$
 30
$
 31
$
  
June 2024
S M T W T F S
            01
$
02
$
 03
$
 04
$
 05
$
 06
$
 07
$
 08
$
09
$
 10
$
 11
$
 12
$
 13
$
 14
$
 15
$
16
$
 17
$
 18
$
 19
$
 20
$
 21
$
 22
$
23
$
 24
$
 25
$
 26
$
 27
$
 28
$
 29
$
30
$
            
July 2024
S M T W T F S
  01
$
 02
$
 03
$
 04
$
 05
$
 06
$
07
$
 08
$
 09
$
 10
$
 11
$
 12
$
 13
$
14
$
 15
$
 16
$
 17
$
 18
$
 19
$
 20
$
21
$
 22
$
 23
$
 24
$
 25
$
 26
$
 27
$
28
$
 29
$
 30
$
 31
$
      
August 2024
S M T W T F S
        01
$
 02
$
 03
$
04
$
 05
$
 06
$
 07
$
 08
$
 09
$
 10
$
11
$
 12
$
 13
$
 14
$
 15
$
 16
$
 17
$
18
$
 19
$
 20
$
 21
$
 22
$
 23
$
 24
$
25
$
 26
$
 27
$
 28
$
 29
$
 30
$
 31
$
September 2024
S M T W T F S
01
$
 02
$
 03
$
 04
$
 05
$
 06
$
 07
$
08
$
 09
$
 10
$
 11
$
 12
$
 13
$
 14
$
15
$
 16
$
 17
$
 18
$
 19
$
 20
$
 21
$
22
$
 23
$
 24
$
 25
$
 26
$
 27
$
 28
$
29
$
 30
$
          
    Available     Unavailable  Check-In Only  Check-Out Only

 

The 10% Guest 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
  • Jacques Scott Wine & Spirits pre-order & hold for check-in
  • Referral to preferred vendors, guest services desk assistance

At-Villa Benefits

  • Day-after-arrival guest services follow-up
  • Complimentary early check-in, if no check out on same day
  • Gilchrist & Soames bath products
  • Pre-stocking of groceries & beverages (delivery fee applies)
  • Arrange chefs, cooks, babysitting & family photography
  • $1,500 of Accidental Villa Damage Protection
  • Complimentary pack-n-plays, booster seats, & baby gates
  • Tandem kayaks available for discounted rental*

*Signed waiver required.

On The Rocks estate is on an elevated rocky bluff overlooking the Caribbean Sea. In the evening it is not unusual to see cruise ships passing by on their way back to Jamaica or the USA. We have great panoramic views, however, you would not enter the beach from the rear of the house. 

This executive residential development of "Beach Bay" has about 12 homes, like On The Rocks, that all share a sandy beach cove with protected snorkeling just east of the villa. Parking is offered if you prefer to drive.  The owner has 6 beach chairs for you to use. If you need more, please ask the manager.

The beach offers a sandy entry into the water and multiple palm trees provide shade--no need to take an umbrella! As this is still a marine environment, we recommend either swim fins or stretchy water shoes to protect the feet from sharp shell shards, broken urchin spines, etc.  

The water is clear and the bottom is sandy, but we still err on the side of caution.

General Grand Cayman Beach Notes

All beaches in Grand Cayman are technically public since the Crown owns up to the high water mark.

The shoreline quality behind your property may vary slightly from the images on our website due to shifting tides and weather patterns. 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 over the years during the 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.

Begins Ends Daily
Aug 15, 2023Nov 03, 2023 $1,000
Nov 04, 2023Nov 17, 2023 $1,200
Nov 18, 2023Nov 25, 2023 $1,795
Nov 26, 2023Dec 15, 2023 $1,395
Dec 16, 2023Dec 26, 2023 $2,395
Dec 27, 2023Jan 04, 2024 $2,645
Jan 05, 2024Mar 01, 2024 $1,695
Mar 02, 2024Apr 12, 2024 $1,845
Apr 13, 2024May 24, 2024 $1,245
May 25, 2024Aug 14, 2024 $1,350
Aug 15, 2024Nov 01, 2024 $1,000
Nov 02, 2024Nov 22, 2024 $1,200
Nov 23, 2024Nov 30, 2024 $1,795
Dec 01, 2024Dec 18, 2024 $1,395
Dec 19, 2024Dec 26, 2024 $2,395
Dec 27, 2024Jan 05, 2025 $2,645
Jan 06, 2025Mar 01, 2025 $1,695
Mar 02, 2025Apr 12, 2025 $1,845
Apr 13, 2025May 24, 2025 $1,245
May 25, 2025Aug 14, 2025 $1,350
Aug 15, 2025Nov 01, 2025 $1,000
Nov 02, 2025Nov 22, 2025 $1,200
Nov 23, 2025Nov 30, 2025 $1,795
Dec 01, 2025Dec 18, 2025 $1,395
Dec 19, 2025Dec 26, 2025 $2,395
  • Rates above assume full occupancy of the villa + guest suite, 14 guests total.
  • 13% Occupancy Tax added to all rates.
  • 10% Guest 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. 

Lower Occupancy Discounts

Owner offers lower rates for fewer guests:

  • Groups of 12 or fewer guests, not needing the guest suite over non-holiday nights, receive a $150 discount off the daily rate. 
  • The guest suite will be locked off for the duration of your stay.

Occupancy Discounts are automatically applied against the full base rent when entering your dates and number of guests.  

Booking Rules

  • 5-night minimum stay 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 dates are split into two rental periods. Please inquire with your travel dates prior to booking.
  • Shorter stays may be available but subject to a higher cleaning fee. Please inquire before booking.
  • Must be 25 years or older to rent and must occupy the home during the entire stay.
  • Owner does not permit local rentals or staycations.

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.

Book Your Stay!

Our reservations team is here to help you.
Call 866-358-8455

Have questions about this property? Email us using the button below.

Ask a Question