
Kailypso
Welcome to Kailypso, a 3-bedroom beachfront villa in Cayman Kai located on Bio Bay. Measuring over 2,800 square feet with spectacular outdoor spaces, cozy interiors, and a secluded beach, this popular villa is the perfect destination for family vacations and group getaways.
Nestled among tall palm trees and lush tropical plants, Kailypso’s waterfront pool and patio create a tropical oasis. Plenty of loungers dot the pool deck for sunbathers to kick back and work on their tans. After hours under the sun, cool off with a refreshing dip in the pool or seek shade in the screened-in porch. A wooden pathway leads you down from the pool deck on to a soft sandy beach with private boat dock.
Beach lovers will love this wide slice of paradise with chairs, loungers, tiki torches, and hammocks set up on the beach. Take full advantage of the private dock by booking a charter to Sting Ray City and request to be picked up right off your dock—it’s the ultimate charter experience!
Two single kayaks are provided during your stay. During the day, launch from the dock and explore the calm surrounding waters of Cayman Kai. Then, on moonless nights, take the kayaks out and watch the water glow with light as you paddle. Bio Bay is one of the few bioluminescent bays in the world making it an unforgettable experience.
Kailypso’s interiors feature an open concept great room with living and dining areas furnished in light tropical decor. The formal dining table seats 6 and is adjacent to the kitchen with ocean views. A galley kitchen comes equipped with modern appliances including a microwave and dishwasher, plus cookware, dishes, glassware, and cutlery.
A full-width screened-in porch sits off the great room leading out to the pool deck. The porch is furnished with comfortable seating areas and a patio dining table (seats 8). A charcoal grill and outdoor dining table (seats 6) sits on the pool deck and is perfect for island cookouts under the stars.
Kailypso’s three bedrooms include a master suite with private bathroom and two additional bedrooms with a shared bath.
Kailypso’s Bedroom Layout
(Sleeps 8 guests total, 6 adults max)
- Master Suite - Furnished with a king bed, ensuite bath with double vanity and shower, plus flat screen TV, ocean views, and private access to the sunroom.
- Guest Bedroom #1 - Ocean views, private access to the sunroom, shared bathroom, and furnished with a queen bed and flat screen TV.
- Guest Bedroom #2 - Garden views, shared bathroom, and furnished with a queen bed and set of bunk beds for kids.
Finally, Kailypso’s location puts it at the center of all the best that Cayman Kai has to offer minus the crowds. Guests can walk to Rum Point to find a heavenly barefoot beach plus watersports activities, a beach bar and grill, a souvenir shop, and a fine-dining restaurant.
The Kaibo is another popular beachfront club also within walking distance featuring live music, food, and drinks, plus limbo on the beach—how low can you go? Ferry service to Camana Bay in Seven Mile Beach departs from the Kaibo Marina and Rum Point regularly making it perfect for day trips.
With a great location and fabulous outdoor amenities, it's easy to see why guests love Kailypso!
*Note: A Cleaning Fee is included due to enhanced cleaning, sanitation, and inspection protocols.
**Silver Thatch tandem kayaks and stand up paddleboards (SUPs) available for discounted rental. Signed waiver required.
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Amenities
Beach Notes
The entire island is only 22 miles wide from west to east, so you are never too far from anywhere on Grand Cayman.
The cove-front homes in Cayman Kai offer calm serene water for docking a rental boat, private charter pick-up if the villa has a dock or just safe shallow water along the edge swimming for little children. Adults won’t swim in the cove—Rum Point is too nice by comparison—the water is shallow and has a softer bottom and there is no reef here for fish life...but we do see the occasional turtle, eagle ray or tarpon swim by in the shallows! Another benefit is that we rarely get any seaweed in the cove so the beaches stay cleaner than the oceanfront beaches.
The beaches are flat white barefoot sand. The big draw to this area is the proximity to the Rum Point Club, a public beach club within a short walk that offers a fantastic barefoot beach, many water sports, a restaurant and bar, gift shop and pick-up beach volleyball games. Also nearby is the Kaibo, a beachfront restaurant, bar, and marina.
Lastly, about 20 minutes east there are 2 large resorts--Morritt's and The Reef--that offer manicured beaches, plus restaurants, a grocery store, liquor store, gift shops, a Subway sandwich shop, the Italian Kitchen Restaurant. These two resorts also offer scuba, snorkel trips, jet ski rentals, windsurfing, kiteboarding, oceanfront pools, and bar service.
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.

The 10% Guest Service Fee includes your Silver Thatch Membership.
The Guest Service Fee is capped at 10 days for extended stays.
Member Benefits
- Centralized on-island Guest Services & Welcome Center
- Unlimited use of Silver Thatch Fitness Center (18+ yrs.)
- Business Center Access: computers, printer, scanner, & FedEx/DHL supplies
- Silver Thatch Discount Card for savings at area businesses
- 10% advance booking discount for private charter
- Complimentary use of snorkel equipment
- Complimentary pack-n-plays, booster seats, & baby gates
- Referral to preferred vendors, guest services desk assistance
- Complimentary early check-in, if no check out on same day
- $500 of Accidental Villa Damage Protection
- Additional tandem kayaks & paddleboards available for discounted rental*
*Signed waiver required.
Guest Reviews of Kailypso
240 Water Cay Road Grand Cayman ,23 user reviews
stars based onCOVID-19
Bay Beauty
Kailypso
Two Weeks in Paradise
Spring Break!
Best Views and Walking to Restaurants
Springtime in Cayman!
Peaceful Retreat - Recharge!
Start of Summer
Birthdays Celebrated
Kailypso Beauty
The Heat of Summer and Beauty of Grand Cayman
Special Home for Our Vacation
Best Vacation!
Great House, Great Location for Young Families
Perfect Vacation
Amazing New Years in Cayman
Kailypso !!!!
Perfect Spot
Fantastic Memories
Kailypso Sweetness
Something Special at Kailypso
Beauty! Beauty! Beauty!
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Begins | Ends | Daily | Weekly |
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Mar 06, 2021 | Apr 16, 2021 | $800 | $4,800 |
Apr 17, 2021 | May 28, 2021 | $675 | $4,050 |
May 29, 2021 | Aug 20, 2021 | $700 | $4,200 |
Aug 21, 2021 | Nov 05, 2021 | $495 | $2,970 |
Nov 06, 2021 | Nov 19, 2021 | $550 | $3,300 |
Nov 20, 2021 | Nov 27, 2021 | $650 | |
Nov 28, 2021 | Dec 17, 2021 | $600 | $3,600 |
Dec 18, 2021 | Dec 25, 2021 | $1,000 | |
Dec 26, 2021 | Jan 04, 2022 | $1,100 | |
Jan 05, 2022 | Mar 05, 2022 | $750 | $4,500 |
Mar 06, 2022 | Apr 15, 2022 | $800 | $4,800 |
Apr 16, 2022 | May 27, 2022 | $675 | $4,050 |
May 28, 2022 | Aug 19, 2022 | $700 | $4,200 |
Aug 20, 2022 | Nov 04, 2022 | $495 | $2,970 |
- 13% Occupancy Tax added to all rates.
- 10% Guest Service Fee includes your Silver Thatch Membership.
- Guest Service Fee is capped at 10 days for extended stays.
- $145 Cleaning Fee (5 days+), higher cleaning fee for shorter stays
- Owner requires a $500 refundable excess cleaning and damage deposit.
Booking Rules
- 5 nights minimum; shorter stays (on request) incure add'l cleaning fees.
- 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.
- Must be 25 years or older to book and must occupy the property during the entire stay.
Flexible Cancellation Options
Travel planning can be unpredictable right now with reopening protocols subject to change by the government. That’s why we have expanded our cancellation policy to provide you peace of mind should the pandemic upend your travel plans.
Within 60 days of your arrival, should there be no reasonable transport options to Grand Cayman or an unforeseen quarantine is required, you will have two options:
- Defer your trip up to 12 months from the planned arrival date with full payment credited towards a subsequent similar stay, or
- Request to cancel for a full refund of monies paid less a 3.50% cancellation fee.
Book with confidence and review our Cancellation Policy for complete details.
Villa Cleaning & Sanitation
We're committed to the health and safety of all our guests and have adopted enhanced cleaning safeguards to suppress the spread of COVID-19. All villas are cleaned and sanitized prior to each guest's arrival using health agency-approved cleaners and disinfectants. 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.