Kailypso

3 Bedrooms 2 Bathrooms 8 Sleeps Grand Cayman

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 on the screened-in porch. A concrete pathway leads you down from the pool deck onto a soft sandy beach with a private boat dock. Beach lovers will love this slice of paradise. 


Take full advantage of the villa's private dock by booking a charter to Stingray City. Request to be picked up and dropped off right on your dock for 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 three bedrooms include a primary suite with an ensuite bathroom and two additional bedrooms with a shared bathroom between them. 


Sleeping Arrangements
(Sleeps 8 guests total, 6 adults max)



  • Primary Suite - king bed, ocean views, television, walk-out access to screened porch, ensuite bath with double vanity and shower.

  • Ocean Bedroom - king bed, ocean views, television, walk-out access to screened porch, shares hall bathroom furnished with shower.

  • Garden Bedroom - queen bed + bunk bed for kids, garden views, shares hall bathroom furnished with shower.


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 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 with seating for 8.


A charcoal grill and outdoor dining table, with seating for 6, sit on the pool deck and are perfect for island cookouts under the stars.


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, The Kaibo, or Starfish Point. 


With a great location and fabulous outdoor amenities, it's easy to see why guests love Kailypso!



Note: The boat photographed at the dock is not included with the villa, however, a boat rental can be arranged.  


*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.

  • Barefoot Beach
  • Private Pool
  • Private Dock
  • 2 Single Kayaks Included
  • Chaise Lounges
  • Beach Hammocks
  • Outdoor Shower
  • Sunroom
  • WiFi/internet
  • Keyless Entry
  • Flat Screen TVs
  • Central A/C
  • Cable TV
  • Stereo
  • DVD Player
  • Full Kitchen
  • Modern Appliances
  • Coffee Maker
  • Toaster
  • Charcoal and Propane Grills
  • Washer & Dryer
  • Linens Provided
  • Beach & Bath Towels Provided
  • Iron & Board
  • Hair Dryer
  • Off Street Parking
  • No Smoking Allowed
  • No Pets Permitted
  • Kayaks & Paddleboards for Rent
LEAVE A REVIEW
July 10, 2023 - Website

The Best!!

by Joshua
My family and I just returned from our best vacation to date. The house and location was absolutely perfect. We typically stay around 7 mile beach but from here on out we will be back to run point and hopefully this house.
April 17, 2023 - Website

Picture on a Postcard

by Gary
We had an awesome time staying at the Kailypso. The view of the bay could of been a picture on a postcard. The kids enjoyed using the Kayaks on the Bay and laying out by the pool. It was nice having the gas grill, as we cooked out almost every night. Loved our stay and hope to visit again in the future.
April 13, 2023 - Website

Fantastic

by Pete
Fantastic experience Thank you
March 25, 2023 - Website

Location

by Chris
Great house in beautiful location! Would come back hear every time we visit.
January 20, 2023 - Website

Great Villa, beautiful and quiet location

by Ian
We stayed at Villa Kailypso over Christmas and New Year 2023. The Villa was great, with a fantastic beach front aspect. From the reviews we read we had expected a lot and the Villa didn\'t disappoint! You definitely need a car, we toured most of the island and this confirmed that we had chosen the best area for our needs. Relaxed and quiet location. The walkable dining options were limited but this will improve when Rum Point is fully open in summer 2023. Grand Cayman Villa staff were helpful before and during stay, cleaning appointment was missed but quickly resolved.
December 12, 2022 - Website

Bioluminescence!!!

by Becky
We chose this property to experience the bioluminescence and be away from the crowds. The bioluminescence did not disappoint! It is incredible to kayak and see it. We did this several nights. It is much better than taking an excursion and only seeing it once. We rented a car so we could go to several beaches and go into Georgetown but we stayed mostly at the property because it was everything we needed to relax and have a great stay. The pool was a nice touch to cool off when in the sun. The property manager answered any requests quickly. The only downside was Rum Point is closed for renovations until April.
December 2, 2022 - Website

Magical

by MK
We had a wonderful stay at the Kailypso. The house was clean and comfortable. We ate every night in the screen porch. Mornings, we would go walk or run in the neighborhood. Kayaking during the day in the Bay and there is a ton of beautiful starfish right off the bay. Although Rum Point restaurant was closed for renovation, the Snorkeling was great. Bioluminescence at night was magical. We will miss this place very much.
September 8, 2022 - Website

Family vacation

by Mihnea
Property is acceptable with the pool being a plus. Well stocked with the basic necessities of a rental. Location is a little challenging since it is a solid 45 minutes driving from the busy part of the island. So no car, no fun! Property manager was very good helping in more than one occasion. However the service company attached to this property was utterly useless. No interest in helping with anything despite the fact that we were told that it was their job! Overall a good stay-on the pricey side but again this is 2022!!
June 30, 2022 - Website

Kailypso

by Jennifer

The property was beautiful and in a great location.

June 21, 2022 - Website

Thank you Grand Cayman Villas!

by Shelley
We so much enjoyed out stay...Judy our host was wonderful! Such an inviting, comfortable home, the kitchen was well stocked, Clean linens, exterior maintained, and that view was incredible!
May 31, 2022 - Website

Highly Recommend!

by Robert
It is as beautiful as the picture! Clean beach right on the bio bay. We paddled kayaks each evening. I swam laps in the bay and ran in the mornings around the quiet neighborhood. Kayak to starfish point. Did many excursions within walking distance to Kaibo marina. It was perfect for our family of six (3 adult kids and 1 teenager). Highly recommend!
May 10, 2022 - Website

Our fourth Visit

by Fritz

Full disclosure I am in the Hotel business as a Hotel Operator and Developer, so when my wife and I get to travel with and hopefully without kids, we prefer to stay in homes as I'm in hotels every day. I am also keenly aware of the type of service you receive when booking, we always book through rental agencies because of incredible service compared to Air BnB or VRBO. We booked our fourth Trip Kailypso in Spring of 2019, and due to covid we were finally able to return in 2022, which was too long as Kailypso has become our "southern cabin." We just wrapped up our fourth visit to this charming private home and it was as good as it's ever been. This is the perfect place for a couple or small family. Private, calm waters, out of the wind and walking distance to everything you need. We spend our days at the pool or Rum Point Club, bone fishing in the mornings and this year, much to our pleasure at the new Silverthatch service center. This new feature from Silverthatch made our trip, access to a gym, concierge service, and free rentals of snorkel gear, blue tooth speaker, coolers made this destination even better. I hope to return multiple times every year to this location. Feel free to reach out to myself with any personal questions you may have or references. fritz.heller@nmhmhotels.com

January 17, 2022 - Website

Exactly as described

by Jeff W
Our small party of four really enjoyed our time at Kailypso, it was a shame that the two nearby restaurants etc (Rum Point and Yacht Club) were closed but that cannot detract from the location or the facilities of Kailypso. We had one small issue with water temperature at one shower, but this was promptly dealt with. We have twice previously rented through GCV&C and following this very positive experience would have no hesitation in doing so again or recommending their services to one and all.
September 2, 2021 - Website

Awesome stay

by Willie F
We spent a week\'s staycation at Kailypso and had a relaxing time. The villa is well laid out and everything was clean and tidy. We enjoyed early morning walks along the main road followed by leisurely dips in the pool followed by our morning coffee on the extensive pool deck overlooking the lagoon. Lots of deck furniture let us always find a shady spot. We were joined most afternoons by a pair of friendly Caribbean Whistling ducks who would take bread from our fingers. We used the kayaks to explore the bio-luminescent lagoon right off the dock. Local restaurants included Over The Edge for breakfasts and the Italian Kitchen for sit in or delivery. Kaibo and Rum Point restaurants are closed at this time of year so the well appointed kitchen was put to good use. Recommended 🙂
April 20, 2020 - Website

COVID-19

by Deann
We unfortunately could not stay due to COVID-19 but the rental company was absolutely wonderful. They had great communication even before the airport shut down. Then they reached out to everyone as soon as the airport closed. They offered full refunds and did so in a timely fashion. I highly recommend this rental company.
March 10, 2020 - Website

Bay Beauty

by Anne
Well equipped and beautiful home on the beach of bioluminescent bay! The house was perfect for us (6) with 3 bedrooms, 2 full baths, comfortable living room and well equipped kitchen. The pool area was awesome and we kayaked every day. Location was perfect for us- we explored the area by the bay and especially loved Kaibo! An amazing restaurant within walking distance! Would go back!
February 11, 2020 - Website

Kailypso

by Drue
This was a wonderful home to stay in. Very quiet area. The bay is awesome. We were checking in late and the manager even got us some basic grocery supplies for the morning so we had essentials. We hope to go back some day!
January 14, 2020 - Website

Two Weeks in Paradise

by D.S.
Our family enjoyed two wonderful weeks in the Kailypso. We all agreed that it was one of the best vacations we have enjoyed. We would stay there again and refer it to our BEST Friends.
October 5, 2019 - Website

Special Home for Our Vacation

by Monks and Trabourgs
This marks out third time to Grand Cayman and third different property. We love the Cayman Kai and Rum Point area. Kailypso is our favorite so far and we will visit again.
October 5, 2019 - Website

The Heat of Summer and Beauty of Grand Cayman

by Doug
Wonderful location and home. Scott at Grand Cayman Villas helped us decide on Kailypso after we looked at 4 options. We are happy with the choice we mage. Near restaurants, snorkeling, activities. Nice beach, long walks, rented bikes. Pick this home - you will not be disappointed.
October 5, 2019 - Website

Kailypso Beauty

by Nelson
Loved everything about this home. No hype. All promises kept! We will come again!
October 5, 2019 - Website

Birthdays Celebrated

by Meyer Family
Our family is one of those with multiple June birthdays. We celebrated at Kailypso. Amazing home, on a peaceful bay, short, safe walks to Rum Point and Kaibo. Fantastic food and fun activities at both locations. Make sure you go out to the stingray sandbar with Joe at Silver Thatch Charters! Courteous, knowledgeable and just a fun guy! If we could give this home 6 stars, we would!
October 5, 2019 - Website

Start of Summer

by Smart Family
We started our summer at Kailypso on Grand Cayman. Wish we could have spent the entire summer in Grand Cayman! Fresh, safe, quiet, fantastic water, food and beverages! Rum Point and Kaibo were favorites. This is the are you want to stay!
October 5, 2019 - Website

Peaceful Retreat - Recharge!

by Mary and Faye
Two couples, friends forever, travel to a destination every year. This year we picked Grand Cayman. Honestly can not believe we have not been here before and we will come again! Peaceful, quiet, safe, lots of activities! Kailypso was a wonderful home. Larger than what the pictures suggest. Rarely do you find a home the is better in person than the photos online - Kailypso is one such home! Magical location, we walked, swam, rented bikes/kayaks and paddle boards. We will book this home next spring as well!
October 5, 2019 - Website

Springtime in Cayman!

by Elizabeth and Dan
Perfect home. Perfect location, Perfect weather. Everyone friendly. Highly recommend!
October 5, 2019 - Website

Best Views and Walking to Restaurants

by Fran
Kailypso was a wonderful home for our family of 6. We spent every day between Kailypso, Rum Point and starfis point. Safe area, no traffic, you can walk everywhere. We did take the Ferry over to 7 Mile Beach and recommend that for a morning/afternoon. Restaurants in the north side were wonderful! Thank you for sharing your wonderful home! Fran M.
October 5, 2019 - Website

Spring Break!

by B. Hendricks
Our family stayed at Kailypso over spring break. We looked at many homes in the Cayman Kai / Rum Point area before deciding on Kailypso. Wonderfully well-maintained home, great location. Paddleboarding off the beach every day. Walks to Rum Point, starfish point and Kaibo. Grand Cayman Villas was prompt with responses and helped us plan a memorable vacation. We recommend Kailypso to all ages! Jus a fantastic home. We hope to return another time!
May 20, 2019 - Website

Great House, Great Location for Young Families

by Allison
We were 4 Adults and 3 kids and found Kailypso very comfortable. The pool was great and even better were the kayaks. We paddled around the bay day and night and very much enjoyed the bioluminescence! We enjoyed kayaking out to the beach at the bay entrance and snorkling. Starfish Point is a 5 min drive and was another highlight of our trip. Rum Point was even closer and we took advantage of the restaurant and the Red Sail watersports. The kitchen was fully loaded with all the cookware we needed and we just had to supply the charcoal for the bbq grill. We would definitely recommend this to other families looking for a peaceful vacation!
May 20, 2019 - Website

Best Vacation!

by Susanne
We have had the best vacation! We are all wishing we could stay longer! We loved the house and being near Rum Point and Kaibo is the perfect location. We rented a car and drove all over the island, we even went to Seven Mile beach for the day and it made us realize we love being in Cayman Kai! The house is so nice with the pool and being right on the Bio Bay, it was perfect for us. We can\'t wait to come back!
May 20, 2019 - Website

Perfect Vacation

by Ann
Thanks for the use of your beautiful home, It was perfect for our vacation and checked off all the boxes. We appreciated the location as well as the amenities and made use of them daily. We had an small issue with a ceiling fan but it was addressed quite quickly and resolved easily thanks to Judy\'s help. We would highly recommend this home and would go back again in a heartbeat!
May 20, 2019 - Website

Amazing New Years in Cayman

by Dee
Thank you for sharing your home with our family over New Years. We enjoyed the home and look forward to returning soon. Rum Point and Kaibo were wonderful day and night.
May 20, 2019 - Website

Kailypso !!!!

by Allison
Kailypso was a wonderful choice. We had 4 adults and two small children. The area is safe, perfect for small children. Walk to Rum Point. No traffic. The bedrooms were nice and comfy. The kitchen was well stocked. Lots of space for everyone. We highly recommend Kailypso and hope to return next year!
May 20, 2019 - Website

Perfect Spot

by Elizabeth M.
We can not say enough positives about Kailypso. Would give the home a 6 star if that was an option! Great location and views. Safe. No seaweed! The Bio Bay is stunning at night time! Rum Point was a favorite daytime spot, as well as lunch!
May 20, 2019 - Website

Fantastic Memories

by Keith S
Great memories from our time at Kailypso. We will be returning here. Great location, home, walks to Rum Point and Kaibo. Starfish Point is a must. Bio Bay. Snorkel charter to Stingray City is a must and they will pick you up at Kailypso - ask for Joe at Silver Thatch Watersports.
May 20, 2019 - Website

Kailypso Sweetness

by Edwards Family
Pictures do no justice to this home. Relax with a great view, fresh breeze, great safe walking area. We have already booked for next year!
May 20, 2019 - Website

Something Special at Kailypso

by Roger and Pat
Every aspect of Kailypso was special for our family. Third time on island - first time at Kailypso. The other homes we stayed in were very nice, but Kailypso was a notch above and our favorite. The kids loved the deck and pool, kayaking and paddle boards. We rented jet skiis for one day as well. The home is clean and up to date. Nice bedrooms, Comfortable beds. Plenty of room to spread out. We will be back.
May 20, 2019 - Website

Beauty! Beauty! Beauty!

by Beth Ann
Wonderful home. Do not miss this one!!!
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    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
  • Guest Services 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
  • $1,500 of Accidental Villa Damage Protection
  • Additional tandem kayaks & paddleboards available for discounted rental*

*Signed waiver required.

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 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 $595
Nov 04, 2023Nov 17, 2023 $650
Nov 18, 2023Nov 25, 2023 $750
Nov 26, 2023Dec 15, 2023 $695
Dec 16, 2023Dec 26, 2023 $1,250
Dec 27, 2023Jan 04, 2024 $1,450
Jan 05, 2024Mar 01, 2024 $850
Mar 02, 2024Apr 12, 2024 $895
Apr 13, 2024May 24, 2024 $875
May 25, 2024Aug 14, 2024 $795
Aug 15, 2024Nov 01, 2024 $595
Nov 02, 2024Nov 22, 2024 $650
Nov 23, 2024Nov 30, 2024 $750
Dec 01, 2024Dec 18, 2024 $695
Dec 19, 2024Dec 26, 2024 $1,250
Dec 27, 2024Jan 05, 2025 $1,450
Jan 06, 2025Mar 01, 2025 $850
Mar 02, 2025Apr 12, 2025 $895
Apr 13, 2025May 24, 2025 $875
May 25, 2025Aug 14, 2025 $795
Aug 15, 2025Nov 01, 2025 $595
Nov 02, 2025Nov 22, 2025 $650
Nov 23, 2025Nov 30, 2025 $750
Dec 01, 2025Dec 18, 2025 $695
Dec 19, 2025Dec 26, 2025 $1,250
  • 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. 

Booking Rules

  • 5 nights minimum.
  • 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.

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.

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