Home Vacation Rentals By Owner In North Side, Grand Cayman

Showing 15 Of 15 Vacation Rentals
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Exceptional(10)

$402.27

/ Nightly
Condo

BEACH and POOL at Rum Point - North Side in most secluded and tranquil area

North Side, Grand Cayman, Cayman Islands

NORTH SIDE, RUM POINT, GRAND CAYMANbrCondo - 2bedrooms/2bathroomsbrGorgeous condo secluded on a quiet and serene area of the island that gives you an secluded feeling from the rest of the world, North Side is the safest area in the safest island of the Caribbean. Our place is for visitors that love private time with direct access to semi-private beach & pool, our condo is on ground floor exactly at center of the condominium with spectacular and privileged direct access to the beach just in front, and the pool to the left.brbrOur condo is spacious and lots of light through the morning. The shades provide an excellent darkness at time of rest at night, or if you’d keep it open you can enjoy the night breeze while enjoying time at the lanai or back patio.brbrTwo bedrooms with bathrooms each, living room and dining room that is comfortable to spend moments with family and friends. The fully equipped kitchen has all the appliances and utensils necessary for a comfortable stay and still wanting to do some cooking. You will be surprised a the fully stocked of condiments we have to share with you.brbrJust 10 condos in the condominium, meaning lots of beach and pool to enjoy just by yourself! Never a crowd. Our condo is spacious and painted in peaceful white to give you the comfort you need to relax and enjoy the shapes of blue and green the ocean offers.brbrIn the morning you can enjoy the most spectacular sunrises with multicolor effects on the sky, enjoy the day with several tones of blue and green the sky and ocean offers through the day, and then enjoy sunset in different color shades through the afternoon. When appealed to watch the sunset directly, just a five minutes drive to Rum Point makes the trick and then you can enjoy sunset in direct view.brbrParadise in Earth.
Bed 2

Bed

Bath 2

Bath

Sleep 6

Sleeps

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Exceptional(23)

$659.66

/ Nightly
Private Vacation Home

Northside Grand Cayman Getaway w/ Private Beach!

North Side, Grand Cayman, Cayman Islands

Snorkel right out your back door at 'Conquered Fame,' a 4-bedroom, 2-bathroom Cayman Islands vacation rental. Nestled on the north end of the island, this beachfront villa provides an escape from the tourist crowds of Seven Mile Beach, yet still boasts easy access to turquoise Caribbean waters and delicious restaurants! Drive 3 miles to Starfish Point or take a boat to Stingray City for unbeatable photo ops and lifelong memories. Caribbean paradise awaits you and your loved ones at this getaway!brbr-- THE PROPERTY --brbrFree WiFi | Sun Porch | Air ConditioningbrbrStep into a Caribbean paradise when you arrive at this beach bungalow, perfect for several couples, two families, or a friend group looking for the ultimate Grand Cayman vacation!brbrBedroom 1: King Bed | Bedroom 2: Queen Bed | Bedroom 3: Full Bed, Twin Bed | Bedroom 4: 2 Twin Beds | Living Room: Sleeper Sofa | Sun Porch: Sleeper SofabrbrOUTDOOR LIVING: Patio, private beach, outdoor dining area, panoramic Caribbean Sea views, charcoal grill, beach chairsbrINDOOR LIVING: Cable TV, DVD player, dining table, vaulted ceilings, ceiling fansbrKITCHEN: Fully equipped, breakfast bar, toaster, coffee maker, dishware/flatwarebrGENERAL: Washer & dryer, linens, towels, beach towelsbrFAQ: 2 steps required for accessbrPARKING: Driveway (4-5 vehicles)brbr-- THE LOCATION --brbrBEACH WONDERS: Rum Point Beach (1.6 miles), Water Cay Public Beach (2.7 miles), Starfish Point (3.1 miles), Barefoot Beach (8.7 miles), Seven Mile Beach (26.7 miles), Governors Beach (27.2 miles), Kittiwake Shipwreck & Artificial Reef (30.1 miles), West Bay (30.5 miles)brGUIDED FUN: Stingray City (24.2 miles), Wall to Wall Diving (24.6 miles), Cayman Ferries (26.0 miles), Red Sail Sports (28.2 miles)brLOCAL DINING: The Wreck Bar & Grill (1.6 miles), Rum Point Club (1.6 miles), Over the Edge (4.7 miles), Breakers (8.3 miles)brCAYMAN FUN: Cayman Crystal Caves (5.2 miles), George Town (22.6 miles), Cayman Spirits Co. (24.3 miles), Cayman Turtle Center (31.6 miles), Dolphin Discovery Grand Cayman (31.7 miles)brAIRPORT: Owen Roberts International Airport (24.0 miles)brbr-- REST EASY WITH US --brbrEvolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.brbr-- POLICIES --brbr- No smokingbr- No pets allowedbr- No events, parties, or large gatheringsbr- Must be at least 25 years old to bookbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbr- NOTE: The property requires 2 steps to access
Bed 4

Bed

Bath 2

Bath

Sleep 10

Sleeps

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Exceptional(21)

$1244.15

/ Nightly
Private Vacation Home

Far Tortuga: 20 Adults Single Level Beach Villa w/ Heated Pool and Private Dock

North Side, Grand Cayman, Cayman Islands

Welcome to Far Tortuga, a stunning single level, 8-bedroom, 7.5-bathroom luxury villa located on the peaceful North Side of Grand Cayman. This exquisite property offers breathtaking panoramic views of the Caribbean Sea and provides direct access to an expansive sandy beach, a living coral reef, and a private dock for endless water activities. Whether you want to snorkel, kayak, or simply relax by the ocean, the villa offers a perfect backdrop for unforgettable experiences.brbrFar Tortuga is a stunning retreat offering 8 beautifully appointed bedrooms, including two oceanfront king ensuites with sweeping views of the pristine waters. These suites provide the perfect setting for relaxation with unparalleled vistas right from your room.brbrWithin the main house, you’ll find two additional king ensuites, one of which comes with a crib for families traveling with young children. The main house also boasts a unique ensuite bunk bedroom featuring two sets of bunks—one with a full over twin and twin trundle bunkbed and a two-twin bunkbed—ideal for kids or group stays.brbrFor those seeking a bit more privacy, the Western Cottage features a charming queen ensuite, perfect for a peaceful retreat. Meanwhile, the Eastern Cottage offers a spacious two-bedroom, one-bathroom layout with a kitchenette, making it an ideal choice for families. The Eastern Cottage includes a king bedroom and a room with two twin beds, ensuring comfort for all.brbrNote- Far Tortuga comfortably sleeps 20 adults, but with the use of 3 rollaway beds and crib, it can sleep 24 guests. Please let us know in advanced if you would like this arranged prior to your stay.brbrOutdoor LivingbrbrStep outside onto the expansive oceanfront patio at Far Tortuga and immerse yourself in the beauty of the Caribbean breeze. Take a refreshing dip in the heated pool, lounge in comfort, and savor the stunning views. A handcrafted charcoal grill, made by a local stone mason, is perfect for grilling fresh seafood or other culinary delights. Just steps from the patio, you'll find a shaded beach table, beach chairs, and an outdoor shower for ultimate relaxation. Enjoy the water with 4 kayaks and snorkeling gear provided, perfect for exploring the crystal-clear waters and vibrant marine life. Dine or unwind in the oceanfront screened-in patio while listening to the soothing sounds of the waves. With so many activities right at your doorstep, Far Tortuga offers a luxurious experience without ever needing to leave the property.brbrbrInterior FeaturesbrbrThe interior of Far Tortuga is thoughtfully designed to provide both comfort and privacy for guests of all ages. The spacious open-floor plan features a brand-new kitchen with modern stainless-steel appliances, including two full-size refrigerators to cater to all your needs. The kitchen is equipped with a full complement of small appliances such as a blender, crockpot, kettle, toaster, Keurig coffee machine, drip coffee maker, coffee grinder, and electric griddle. There’s also a coffee bar with a beverage fridge, a large breakfast bar with seating for seven, and a vaulted ceiling with a fan to create a spacious and airy atmosphere. For families with young children, the villa offers 2 highchairs, 1 crib, and 2 pack-n-plays for added convenience and comfort.brbrAdjacent to the kitchen is a laundry room with a washing machine and dryer, and there’s another laundry room in the Eastern Cottage with a brand-new LG washing machine/dryer tower.brbrThe villa’s sprawling living area is designed for relaxation, featuring comfortable seating, a large flat-screen Smart TV, and an arcade game nook for entertainment. Two large dining tables provide ample seating, ensuring everyone has a comfortable place to gather.brbrbrActivitiesbrbrFar Tortuga offers the perfect blend of relaxation and adventure, with easy access to the nearby Cayman Kai area, home to Rum Point, Starfish Point, and the Bioluminescent Bay, where you can experience natural wonders like glowing waters at night. The area is also ideal for water-sport activities, including excursions to Stingray City, as well as dining at the Kaibo Yacht Club, which features an espresso shop for morning coffee. For convenience, a small grocery store is just two minutes away for all your essentials, making it easy to enjoy both the tranquility of the villa and the vibrant local attractions.brbrbr Please Note brbr-Many beaches around Grand Cayman are protected by Ironshore along the shoreline, and while you may notice a small amount of Ironshore at Far Tortuga, there is plenty of soft, white sand for our guests to enjoy. The beach provides easy access to the water for activities like kayaking, snorkeling, and swimming. Right in front of the house lies the Barrier Reef, offering protected snorkeling just waiting for you to explore. For foot protection, water shoes or fins are recommended, given the abundant marine life and coral. While beaches in Grand Cayman may occasionally experience floating ocean debris and sargassum weed, which is a generally harmless floating seaweed that has become more frequent in recent years, it is mostly seasonal, particularly in the summer. brbr-13% Cayman Islands Government tax is added to all rates, as with any hotel, house, villa or condo in Caymanbrbr-Minimum stay is between 5 and 7 nights depending on the time of year. Certain weeks require Saturday check in/out. Considerations can be made, feel free to contact us in regard of this.brbr-No pets allowed without prior approval and written permission.brbr-Far Tortuga requires a $2500, full refundable, excess cleaning and damage deposit.brbr-Most stores in Cayman are closed on Sundays, so plan accordingly. Please utilize the grocery shopping and pre-stocking if you plan to arrive on a Sunday.
Bed 8

Bed

Bath 7

Bath

Sleep 20

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Exceptional(98)

$896.77

/ Nightly
Private Vacation Home

Villa Esprit – Stunning 3 Bedroom Beachfront Villa in North Side with pool!

North Side, Grand Cayman, Cayman Islands

This exclusive, expansive 3-bedroom beachfront villa in North Side is adorned with elegant furnishings and cutting-edge fixtures, ensuring your ultimate comfort and convenience. A pleasant 50 minute drive from the airport, this house will take your breath away and the views will mesmerise you and entice you to swim, snorkel and relax on the private beach and soak up the sun around the private pool!brbrStep into this ultra-modern villa boasting a sleek design and a fully equipped modern kitchen outfitted with new appliances, gadgets, and every amenity needed for meal preparation. Entertain in the open-concept living and dining area, perfect for intimate dinners or cozying up with your favorite book while enjoying the large flat-screen TV. With 3 spacious and beautifully appointed bedrooms, including a King bed in the Primary bedroom (installed in September 2025), a queen bed in the 2nd bedroom, and twin beds in the 3rd, that can be converted into a king upon request, everyone will find their perfect retreat.brbrOutside, your private pool and BBQ area await, along with two kayaks inviting you to explore the sparkling ocean and its breathtaking underwater wonderland just beyond the reef. The beach is sandy and rocky, so we recommend water shoes for those of you who like to snorkel and explore the marine life!brbrLocated on the ever-breezy north shore of Grand Cayman, a short drive takes you to a small shopping mall with a grocery store and restaurants, in East End. The famed Cayman Kai/Rum Point area, known for its eateries, bars, and water sports, is a mere 10-minute drive away, while George Town (the main town) and the airport are approximately 55 minutes away.brbrWith its clean contemporary style, this exquisite beachfront abode beckons you to unwind and relish all the splendors of a warm and inviting Caribbean ambiance!
Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps

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Exceptional(30)

$1460.06

/ Nightly
Villa

Treasure Cove – Luxurious private villa with pool and boat dock in Cayman Kai

North Side, Grand Cayman, Cayman Islands

Nestled in the heart of the exclusive Cayman Kai residential community, Treasure Cove is a magnificent retreat that promises an unforgettable experience for reunions with friends or family. This modern, unique, and spacious villa is perfectly situated beside the tranquil waters of the bioluminescent bay, offering a serene and picturesque setting for your vacation. 6 bedrooms, and 4 bathrooms ensure there is ample space to comfortably accommodate up to 14 guests, with a sleeper sofa in the TV area on the second floor. brbrBoasting a range of luxurious amenities, Treasure Cove caters to the needs of discerning guests. Whether you're looking to relax by the pristine private pool, set off on adventures with the two double kayaks and paddleboard provided for exploring the warm waters of the inlet, or simply unwind on your own private boat dock, this villa has everything you need for a truly memorable stay.brbrCayman Kai is a prestigious residential and holiday community known for its exclusivity and tranquility. Most of the villas and condos in the area serve as second homes, ensuring peaceful days and nights, except during major holiday weekends such as Easter, 4th of July, Thanksgiving, and Christmas.brbrFor those seeking a taste of local culture and social interaction, the nearby Rum Point Club and Kaibo Yacht Club Beach Bar and Restaurant offer a vibrant atmosphere where residents and tourists come together to enjoy delicious seafood, sip cocktails, engage in water sports, and relax on the legendary barefoot beaches.brbrStep inside Treasure Cove, and you'll be greeted by a light-filled and professionally decorated interior that serves as the perfect backdrop for your vacation. The spacious living area features multiple conversation areas, including a comfortable L-shaped leather sectional couch ideal for lazy afternoon naps or movie nights. A gleaming gourmet kitchen provides a stylish and well-equipped space for preparing meals and entertaining guests.brbrWhether you're unwinding by the pool, exploring the bay on kayaks, or enjoying a leisurely dinner with loved ones, Treasure Cove offers a luxurious and unforgettable retreat for your next gathering in the Cayman Islands.
Bed 6

Bed

Bath 4

Bath

Sleep 14

Sleeps

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Exceptional(31)

$462.35

/ Nightly
Private Vacation Home

Private, quiet oceanfront home, wrap-around screened porch. Relax on 1+ acres

North Side, Grand Cayman, Cayman Islands

Breezy Bay is an oceanfront, private, single-level home in North Side (Old Man Bay) perfect for your relaxing Grand Cayman vacation. Enjoy panoramic oceanfront views from this beach house with a bright, open air concept and large vaulted ceilings.brbrThe home sits on 1+ acres full of coconut and sea grape trees with lots of places to explore. The oceanfront property has a sea wall with private water access. In front of the home in the crystal clear Caribbean Sea you’ll enjoy snorkeling, kayaking, or shore diving to the nearest site. brbrThe living room, dining and kitchen have an open concept with beautiful ocean views from every room. Relax on the 360 degree wraparound screened porch which has two seating areas both boasting oceanfront views of the Caribbean Sea.brbrThe main house includes 2 bedrooms. The Queen bedroom has private porch access and en suite bathroom. The second bedroom has two (2) twin beds with private porch access and en suite bathroom. Each bedroom has bathroom with toilet and vanity with a shared shower between the two bedrooms (double Jack & Jill). A sleeper sofa is available in the living room to sleep two additional persons.brbrThe Primary/guest suite, 3rd bedroom, is separate from the main house with access from the wrap-around screened porch. The private suite has a king bed, newly renovated bathroom with double vanity and large shower, 3-panel slider door and walk-out patio featuring oceanfront views. This room has a mini-fridge/freezer, toaster, coffee maker, microwave, etc.brbrThe main house is a unique hexagon shape providing fantastic oceanfront views from the open living spaces. The centre of the house features a beautiful Caymanian stone wall up leading to the beach cottage themed vaulted ceilings. The home has an open air concept with views of the crow’s nest from every room in the house. brbrIf you love nature, you will love this private house…plenty of sand, coconut and sea grape trees and even some sightings of Cayman Parrots. A hammock is nestled in between two coconut trees. Kids will enjoy the tree swings and tree house. King sized outside day bed is the perfect place to look out at the sea and take an afternoon nap.brbrSmart TVs and fibre internet throughout. Cable TV in living room and primary suite.brbrWhen accessing the sea, please wear water shoes or fins to protect your feet.brWasher and dryer are available in the garage. Cornhole boards for use as well.brbrKayaks available for guest use (additional waiver required)brbrYou will truly enjoy the serenity of this home in the quiet area of North Side.
Bed 3

Bed

Bath 3

Bath

Sleep 8

Sleeps

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Exceptional(6)

$898.69

/ Nightly
Private Vacation Home

Rum& Little Barron Villa: Your North Side Haven-Beach, Ocean, Garden Views!

North Side, Grand Cayman, Cayman Islands

Welcome to Little & Rum Baron, your exclusive oasis of luxury and tranquility nestled along the pristine shores of Grand Cayman's North Side. This enchanting estate offers the perfect blend of Caribbean charm and modern amenities, providing an unforgettable retreat for discerning travelers seeking the ultimate island getaway.brbrAs you step onto the grounds of Little & Rum Baron, you're immediately greeted by the serene ambiance and breathtaking views of the Caribbean Sea. The Rum Baron main house stands as a beacon of elegance, boasting three beautifully appointed bedrooms, each offering a haven of comfort and tranquility. Sink into the sumptuous king-size beds adorned with crisp linens and plush pillows, and drift off to sleep to the gentle sound of waves lapping against the shore. Each bedroom boasts its own full ensuite bathroom, ensuring privacy and convenience for every guest.brbrStep outside onto the expansive verandas and immerse yourself in the beauty of the surrounding gardens, where vibrant tropical blooms perfume the air and majestic palms sway in the breeze. Whether you're savoring your morning coffee as the sun rises over the horizon or enjoying a leisurely afternoon siesta in the shade, the verandas provide the perfect setting for relaxation and rejuvenation.brbrJust a stone's throw away from the main house lies the charming Little Baron cottage, offering an additional bedroom for those seeking a more intimate retreat. This cozy abode is nestled amidst lush foliage, with panoramic views of the beach and the sparkling turquoise waters beyond. The bedroom features a luxurious king-size bed and a full ensuite bathroom, providing a private oasis of comfort and tranquility. Step outside onto your private patio and feel the soft Caribbean breeze on your skin as you bask in the beauty of your surroundings.brbrOne of the highlights of Little & Rum Baron is its outdoor amenities, designed for both relaxation and entertainment. Take a refreshing dip in the private pool, surrounded by lush landscaping and comfortable lounge chairs where you can soak up the warm Caribbean sun. Gather with friends and family in the outdoor lounge area, where you can enjoy a leisurely afternoon barbecue or sip cocktails as you watch the sun set over the horizon.brbrFor added convenience, the Rum Baron main house is equipped with a personal washer and dryer, allowing you to pack light and enjoy your stay without worrying about laundry. And with a barbecue grill situated between the main house and the cottage, guests can come together to share delicious meals and create lasting memories under the Caribbean sky.brbrWhether you're seeking adventure or relaxation, romance or family fun, Little & Rum Baron offers an unparalleled retreat that captures the essence of island living. From its luxurious accommodations to its breathtaking surroundings, every moment spent here is infused with the magic of the Caribbean. Come experience the beauty and tranquility of Grand Cayman's North Side at Little & Rum Baron – your own private paradise in paradise.
Bed 4

Bed

Bath 3

Bath

Sleep 8

Sleeps

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$506.35

/ Nightly
Private Vacation Home

Mahogany Point 3 – A Beachfront Townhouse with amazing views-by Cayman Villas

North Side, Grand Cayman, Cayman Islands

Nestled within a serene and secluded enclave, this charming resort of oceanfront villas offers a tranquil escape amidst the cool sea breezes and breathtaking vistas of the Caribbean Sea. With both sandy and rocky shorelines, the snorkeling experience right in front of the complex is truly exceptional, and the double kayak provided, make snorkelling a fun excursion! We highly recommend water shoes, as the shoreline is rocky as you enter the sea.brbrMahogany Point 3 stands as one of only five exclusive beachfront units, granting direct access to the pristine white sands just steps from your door. Alternatively, you can unwind on the shaded beachfront patio, savoring the gentle ocean breezes. Amidst the lush gardens surrounding the complex, a freshwater pool offers a refreshing retreat, often providing a private oasis due to the intimate scale of Mahogany Point.brbrStep inside this welcoming space, where extensive remodeling and tasteful redecoration have transformed the condo into a haven of modern luxury. The sleek and fully equipped kitchen boasts upscale appliances, while upstairs, the primary bedroom features a king bed and ensuite, open plan bathroom facilities with a spacious walk-in rainfall shower. The second guest bedroom also offers a king bed and open plan, ensuite bathroom with a powerful shower over a large Kohler tub, while the third guest bedroom downstairs provides a queen bed and adjacent bathroom, ensuring ample space for up to 6 guests.brbrFor water enthusiasts, the condo is equipped with a two-person kayak and two stand-up paddleboards for private use, perfect for exploring the coastline and indulging in snorkeling adventures.brbrVenture just a short 10-minute drive to Rum Point, where you can enjoy beachside dining, watersports, and a vibrant atmosphere. Explore the Botanical Gardens and Blue Iguana Sanctuary, marvel at the wonders of the Crystal Caves, or embark on a breathtaking bioluminescent tour in Cayman Kai. Plan your visit accordingly to witness the magical cove light up with the touch of your hand during the week before and after the New Moon.brbrWhile Mahogany Point is a 45-minute drive from the airport, George Town, and Seven Mile Beach (a rental car is recommended), it offers easy access to renowned local restaurants such as Over the Edge, Rum Point Restaurant, and Kaibo Beach Bar and Grill, as well as beach bars, watersport shops, activities, and a small local grocery store. For larger shopping needs, Fosters is just a scenic 20-minute coastal drive away in East End. brbrRetreat to Mahogany Point 3 for an unforgettable blend of relaxation, adventure, and natural beauty on the captivating shores of North Side, Grand Cayman!
Bed 3

Bed

Bath 3

Bath

Sleep 6

Sleeps

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Exceptional(14)

$402.12

/ Nightly
Private Vacation Home

Luxury 3bd Ocean View, # 1 Cream, Stunning Views

North Side, Grand Cayman, Cayman Islands

Summary:brbrPerfectly located on the tranquil north side of Grand Cayman for those who prefer an almost secluded island retreat, Ocean Paradise offers luxury and relaxation in world-class vacation accommodations yet is conveniently located near renowned Stingray City, The Rum Point and Kaibo’s restaurants, beaches and water sport activities.brbrbrbrThe Space:brbrEscape to a charming, cozy retreat on the northern coast of Grand Cayman. Each one of the five homes at this intimate enclave at Ocean Paradise is characterized by a unique color, the Cream home features three bedrooms (plus a den) and three bathrooms, with fully equipped kitchen, elegant finishes, high-tech amenities, direct beach access, and breathtaking views. Designed to provide the comforts, privacy, and conveniences of your own home, the open space concept of the living and dining area is inviting and cozy, ideal for family meals. Accommodations feature soft linens and beach-inspired décor with stunning ocean vistas. brbrbrbrOcean Paradise is the ultimate destination for those seeking a serene island getaway. Nestled on the tranquil north side of Grand Cayman, this world-class vacation retreat offers a perfect blend of sophistication, relaxation, and convenience. With proximity to renowned attractions like Stingray City, Rum Point, and Kaibo's restaurants and beaches, guests can indulge in water sports activities, bask on the pristine white sand beach, take a refreshing dip in the pool, or simply unwind in a hammock, embracing the blissful tranquility of paradise.brbrbrbrGuest Access:brbrEntire Home.brbrbrbrThe Neighborhood:brbrEmbrace the allure of North Side, where every home and path offers a captivating sea view and an enchanting holiday ambiance. This idyllic district boasts a mix of long-term visitors, retirees, and short-term vacationers seeking solace at renowned retreats, including Ocean Paradise. The area offers a wealth of activities ranging from walking the Mastic Trail and exploring Crystal Caves to indulging in watersports and experiencing the mesmerizing Bioluminescence Tours. Treat your palate at local restaurants like Kaibo and Rum Point, offering a range of culinary experiences from casual beach bars to fine dining establishments, including the acclaimed Kaibo Upstairs helmed by a two Michelin-starred chef.brbrbrbrGetting Around:brbrTo fully embrace the serene ambiance of North Side, we suggest renting a car for convenient transportation, as public options may be limited. With George Town approximately 50 minutes away, having a car will grant you the freedom to explore the area's hidden treasures and embrace the picturesque beauty at your own leisurely pace.brbrbrbrOther Things to Note:brbrUpon booking, you will receive a key code for the keyless entry system, allowing for a seamless and convenient self-check-in process at this exquisite property. brbrbrbrWhile it may not be necessary for everyone, we recommend bringing sea shoes.brbrbrbrIf the booking website does not collect it directly, a refundable security deposit of US$500 will be collected by the property prior to your stay.brbrbrbrWe reserve the right to substitute equal or better accommodation in the event of a double booking or if the rental is unavailable for any reason, including but not limited to sale or repair.brbrbrbrInteraction with Guests:brbrI am on island and can assist you at anytime.
Bed 3

Bed

Bath 3

Bath

Sleep 9

Sleeps

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Exceptional(19)

$442.77

/ Nightly
Villa

Luxury 3bd Beach Front, # 4 Green, Stunning Views

North Side, Grand Cayman, Cayman Islands

Summary:brbrPerfectly located on the tranquil north side of Grand Cayman for those who prefer an almost secluded island retreat. Ocean Paradise offers luxury and relaxation in world-class vacation accommodations and is conveniently located near renowned Stingray City, Rum Point and Kaibo’s restaurants, beaches and water sport activities.brbrbrbrBask on the white sand beach, enjoy the pool, swim and snorkel with a myriad of sea life, or simply lounge in your hammock snoozing away the day.brbrbrbrThe Space:brbrEach one of the five homes at this intimate enclave at Ocean Paradise is characterized by a unique color and Green blends in perfectly with its lush tropical surroundings. The three-bedroom, three-bathroom oasis features spacious accommodations and breathtaking Caribbean views that will leave you speechless. brbrbrbrEnjoy a fully equipped kitchen complete with modern appliances and ample seating for you and your guests. The spacious living area features comfortable seating, high-end electronics, and tasteful decor to create a relaxing and inviting atmosphere. Each of the three bedrooms is beautifully designed with plush bedding and comfortable furnishings, ensuring a peaceful night's sleep. Whether you're lounging on the private balcony, taking a dip in the nearby pool, or exploring the local area, this vacation rental is the perfect retreat for your next getaway.brbrbrbrHome #4 at Ocean Paradise is one of our two premier beachfront homes with spectacular views of Grand Cayman’s northern coastline from almost every room in the house.brbrbrbrGuest Access:brbrEntire Home.brbrbrbrThe Neighborhood:brbrEmbrace the allure of North Side, where every home and path offers a captivating sea view and an enchanting holiday ambiance. This idyllic district boasts a mix of long-term visitors, retirees, and short-term vacationers seeking solace at renowned retreats, including Ocean Paradise. The area offers a wealth of activities ranging from walking the Mastic Trail and exploring Crystal Caves to indulging in watersports and experiencing the mesmerizing Bioluminescence Tours. Treat your palate at local restaurants like Kaibo and Rum Point, offering a range of culinary experiences from casual beach bars to fine dining establishments, including the acclaimed Kaibo Upstairs helmed by a two Michelin-starred chef.brbrbrbrGetting Around:brbrTo fully embrace the serene ambiance of the North Side, we recommend renting a car for convenient transportation, as public options may be limited. With George Town approximately 50 minutes away, having a car will grant you the freedom to explore the area’s hidden treasures and embrace the picturesque beauty at your own leisurely pace.brbrbrbrOther Things to Note:brbrUpon booking, you will receive a key code for the keyless entry system, allowing for a seamless and convenient self-check-in process at this exquisite property. brbrbrbrWhile it may not be necessary for everyone, we recommend bringing sea shoes.brbrbrbrIf the booking website does not collect it directly, a refundable security deposit of US$500 will be collected by the property prior to your stay.brbrbrbrWe reserve the right to substitute equal or better accommodation in the event of a double booking or if the rental is unavailable for any reason, including but not limited to sale or repair.brbrbrbrInteraction with Guests:brbrI am on island and can assist you at anytime.
Bed 3

Bed

Bath 3

Bath

Sleep 8

Sleeps

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Exceptional(22)

$391.19

/ Nightly
Private Vacation Home

Luxury 3bd Beach View, # 3 Blue, Stunning Views

North Side, Grand Cayman, Cayman Islands

Summary:brbrPerfectly located on the tranquil north side of Grand Cayman for those who prefer an almost secluded island retreat. Ocean Paradise offers luxury and relaxation in world-class vacation accommodations and is conveniently located near renowned Stingray City, Rum Point and Kaibo’s restaurants, beaches and water sport activities.brbrbrbrBask on the white sand beach, enjoy the pool, swim and snorkel with a myriad of sea life, or simply lounge in your hammock snoozing away the day.brbrbrbrThe Space:brbrWith its mesmerizing blue exterior that blends seamlessly into the breathtaking ocean views, this home exudes a sense of tranquility and serenity. The three-bedroom, three-bathroom oceanfront home is perfectly suited for families. Each one of the five homes at this intimate enclave at Ocean Paradise is characterized by a unique color and Blue offers its own unique charm.brbrbrbrThe fully equipped kitchen features high-end appliances, ample counter space, and all the necessary cookware and utensils to whip up a culinary masterpiece. The living area is spacious and cozy, featuring plush sofas and chairs, a large coffee table, and tasteful decor that creates a warm and inviting atmosphere for relaxation and entertainment. An outdoor terrace offers the perfect spot to relax and soak up the salty sea breeze with stunning ocean views.brbrbrbrGuest Access:brbrEntire Home.brbrbrbrThe Neighborhood:brbrEmbrace the allure of North Side, where every home and path offers a captivating sea view and an enchanting holiday ambiance. This idyllic district boasts a mix of long-term visitors, retirees, and short-term vacationers seeking solace at renowned retreats, including Ocean Paradise. The area offers a wealth of activities ranging from walking the Mastic Trail and exploring Crystal Caves to indulging in watersports and experiencing the mesmerizing Bioluminescence Tours. Treat your palate at local restaurants like Kaibo and Rum Point, offering a range of culinary experiences from casual beach bars to fine dining establishments, including the acclaimed Kaibo Upstairs helmed by a two Michelin-starred chef.brbrbrbrGetting Around:brbrTo fully embrace the serene ambiance of the North Side, we recommend renting a car for convenient transportation, as public options may be limited. With George Town approximately 50 minutes away, having a car will grant you the freedom to explore the area’s hidden treasures and embrace the picturesque beauty at your own leisurely pace.brbrbrbrOther Things to Note:brbrUpon booking, you will receive a key code for the keyless entry system, allowing for a seamless and convenient self-check-in process at this exquisite property. brbrbrbrWhile it may not be necessary for everyone, we recommend bringing sea shoes.brbrbrbrIf the booking website does not collect it directly, a refundable security deposit of US$500 will be collected by the property prior to your stay.brbrbrbrWe reserve the right to substitute equal or better accommodation in the event of a double booking or if the rental is unavailable for any reason, including but not limited to sale or repair.brbrbrbrInteraction with Guests:brbrI am on island and can assist you at anytime.
Bed 3

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Bath 3

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Sleep 9

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Exceptional(36)

$501.68

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Private Vacation Home

Mahogany Point 2 – A Beachfront Townhouse with amazing views-by Cayman Villas

North Side, Grand Cayman, Cayman Islands

Nestled amidst the enchanting backdrop of the Caribbean Sea, Mahogany Point is a charming retreat comprising tastefully decorated oceanfront villas, perfectly positioned to capture the refreshing sea breezes and mesmerizing ocean views. With both sandy and rocky beaches, the snorkeling opportunities right in front of the villas are nothing short of spectacular.brbrStep out the back door to discover a pristine beach where vibrant coral reefs await exploration, or embark on a scenic kayak journey along the picturesque shoreline. Alternatively, unwind by the freshwater pool, nestled amidst the tranquil coconut trees, offering a serene oasis in the heart of the complex. Thanks to its intimate scale, Mahogany Point often offers blissful solitude on both the beach and by the pool.brbrInside, this inviting condo features a king bed in the master bedroom with an ensuite bathroom, a queen bed in the upstairs bedroom also with an ensuite bathroom, and a queen bed in the downstairs bedroom with its own full ensuite bathroom, accommodating up to 6 guests comfortably. The recently remodeled kitchen is fully equipped with everything you need to prepare delicious meals, whether you opt for fresh seafood from Rum Point or consult with your property manager for local recommendations. Enjoy sunset breezes and Caribbean cocktails on the patio, the perfect spot to unwind after a day of adventure.brbrFor those seeking activity, the completely newly renovated Rum Point, with its beach bar, restaurant, and watersports shop, is just a short 10-minute drive away. Explore the local flora and fauna at the Botanical Gardens, marvel at the wonders of the Crystal Caves, or embark on a breathtaking bioluminescent tour in Cayman Kai. Plan your visit accordingly to witness the cove light up with the touch of your hand during the week before and after the New Moon.brbrAlthough a 45-minute drive from the airport and George Town (rental car highly recommended!), Mahogany Point is conveniently located just minutes away from a variety of local amenities, including restaurants like Over the Edge, Rum Point Restaurant, and Kaibo Beach Bar and Grill, as well as beach bars, watersport shops, activities such as Crystal Caves, and a small local grocery store at Chisholm’s. Retreat to Mahogany Point for a tranquil escape surrounded by natural beauty and endless opportunities for relaxation and adventure.
Bed 3

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Bath 3

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Sleep 6

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Exceptional(13)

$302.47

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Condo

Spacious 2-Bedroom 2-Bathroom Beachfront Condo with Heated Pool

North Side, Grand Cayman, Cayman Islands

Summary:brbrThis two 2-bedroom condominium located in Old Man Bay on the North Side of Grand Cayman is nestled in a prime oceanfront location. Step into this expansive unit boasting over 1,685 sq ft of living space, including a generously sized balcony that offers panoramic and uninterrupted vistas of the magnificent Caribbean Sea. Immerse yourself in the breathtaking views not only from the balcony, but also from the comfort of the living room and kitchen, creating a truly mesmerizing experience.brbrbrbrThe Space:brbrWith classic furnishings and tasteful decor, this exquisite retreat features a spacious living area, fully equipped kitchen with top-of-the-line appliances, two cozy bedrooms and bathrooms. Experience the perfect tropical escape in this tranquil oasis.brbrbrbrThe complex is designed to be fully wheelchair accessible, ensuring that individuals with mobility restrictions can navigate it comfortably. Additionally, for the upper floors, the complex features an elevator—an amenity not commonly found in many condo complexes in Cayman, even those situated along the renowned Seven Mile Beach. This inclusion demonstrates our commitment to providing convenient and inclusive accommodations for all guests.brbrbrbrGuest Access:brbrCondo, shared heated pool and beach.brbrbrbrThe Neighborhood:brbrEmbrace the allure of North Side, where every home and path offers a captivating sea view and an enchanting holiday ambiance. This idyllic district boasts a mix of long-term visitors, retirees, and short-term vacationers seeking solace at renowned retreats, including Ocean Paradise. The area offers a wealth of activities ranging from walking the Mastic Trail and exploring Crystal Caves to indulging in watersports and experiencing the mesmerizing Bioluminescence Tours. Treat your palate at local restaurants like Kaibo and Rum Point, offering a range of culinary experiences from casual beach bars to fine dining establishments, including the acclaimed Kaibo Upstairs helmed by a two Michelin-starred chef.brbrbrbrGetting Around:brbrTo fully embrace the serene ambiance of the North Side, we recommend renting a car for convenient transportation, as public options may be limited. With George Town approximately 50 minutes away, having a car will grant you the freedom to explore the area’s hidden treasures and embrace the picturesque beauty at your own leisurely pace.brbrbrbrA restaurant, bar, liquor store and gas station are within walking distance.brbrbrbrOther Things to Note:brbrIf the booking website does not collect it directly, a refundable security deposit of US$500 will be collected by the property prior to your stay.brbrbrbrWe reserve the right to substitute equal or better accommodation in the event of a double booking or if the rental is unavailable for any reason, including but not limited to sale or repair.
Bed 2

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Bath 2

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Sleep 6

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Exceptional(6)

$1007.07

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Private Vacation Home

Flip Flop Kai: Private Pool + Dock & 2 Free Kayaks on Bio Bay.

North Side, Grand Cayman, Cayman Islands

*** PROPERTY DESCRIPTION ***brWelcome to this lovely private villa situated on a sandy beach with scenic views of the Bioluminescent Bay, in Cayman Kai. Newly redecorated and painted, Flip Flop is a popular 3-bedroom beach cottage with fabulous amenities. brbrThis home boasts stunning water vistas from almost every room plus a delightful beachfront veranda and gazebo, where you can listen to the gentle sound of lapping waves and savor beautiful sunsets. Flip Flop ticks almost all the boxes with a pool, sunset views, screened porch, thatched cabana, private dock, and within walking distance to beach bars and restaurants. brbrThe freshwater private pool is shaded by palm trees, making it a perfect hideaway spot for relaxing with a tropical drink. The spa is located at the end of the pool and can be heated as an optional add-on for the duration of your stay for $50/day, year-round.brbrOn the sandy beach, you can enjoy paddleboarding and kayaking. During moonless nights, you can venture out into the bay to witness the incredible light display provided by nature! The owners also own the adjacent sandy lot; perfect for frisbee and soccer. brbrFlip Flop Kai has a private dock with thatched cabana, which allows you to rent a boat or jet skis. Book a charter to Stingray City and coordinate dockside service right off the home's dock! It's the ultimate convenience for private snorkeling or scuba charters with our friends at Silver Thatch Water Sports.brbrInside, this beautifully decorated beach villa is an ideal place for a comfortable family gathering or a fun vacation with friends. Lots of glass brings the Caribbean blue indoors.brbrThe open-concept kitchen is fully equipped, perfect for the chef in your group to prepare delicious meals. There's also a gas BBQ for grilling and a large thatched beach cabana for sunset cocktail hour.brbr***Sleeping Arrangements***br(Licensed to sleep 8 guests total, 6 adults max.)br-- Bedroom #1: upper level, king bed, waterfront views, television, DVD player, ensuite with double vanity and shower. br-- Bedroom #2: upper level, two queen beds, ceiling fan, shares adjacent bathroom equipped with shower bath.br-- Bedroom #3: upper level, two twin XL beds, ceiling fan, shares adjacent bathroom equipped with shower bath; beds can be fitted into a king bed upon request.br-- Additional bedding: sleeper sofa in the media den for children only; uses half-bath on the first floor. brbrWithin walking distance of the villa, you'll discover Starfish Point, a family-friendly beach spot where you can interact with starfish. Along the way, you'll find The Kaibo, a beachfront dining destination with two restaurants and a coffee shop.brbrTo the north, you won't want to miss the new Rum Point Club, a public beach with great snorkeling, beach service, an open-air beach bar, plus a new restaurant serving lunch and dinner. Red Sail Watersports operates off the dock for excursions to Stingray Sandbar, or a sunset cruise just before dinner. brbrFlip Flop Kai truly offers an ideal place to relax and unwind, Cayman-style, with your loved ones in a sunny paradise...barefooted. brbr================brbr***Rate Details*** br-- 13% Occupancy Tax added to all rates.br-- 10% Guest Service Fee includes your Guest Services Membership.br-- A $225 Departure Cleaning Fee is added for all stays.br-- A Refundable Damage Deposit of $1,500 is required for all stays.br-- Refundable Damage Deposits will be returned to the guest 7 business days after departure pending any damages.brbr***Booking Rules***br-- Christmas & New Year's dates are split into two rental periods. Please inquire about your travel dates before booking.br-- Shorter stays may be available but subject to a higher cleaning fee. Please inquire before booking.br-- Must be 25 years or older to book and must occupy the property during the entire stay.brbr***Grand Cayman Villas & Condos Guest Services***brThe 10% Guest Service Fee includes your Guest Services Membership. brbr***Member Benefits***br-- Complimentary use of snorkel equipmentbr-- Complimentary pack-n-plays, booster seats, & baby gatesbr-- Guest Services Discount Card for 10% savings with our restaurant partnersbr-- 10% Advance Booking Discount for a private Stingray City charterbr-- Complimentary early check-in, if no check out on same daybr-- Centralized on-island Guest Services & Welcome Centerbr-- Unlimited use of Private Fitness Center (18+ yrs.)br-- Business Center Access: computers, printer, scanner, & FedEx/DHL suppliesbr-- Referral to preferred vendors, guest services desk assistancebr-- Additional single/tandem kayaks & paddleboards are available for discounted rental. A signed waiver is required.brbr***Nearby Points of Interest***br-- Villa is located on Cayman's Bioluminescent Baybr-- 13-minute walk to the Rum Point Club & the Kaibo Beach Bar & Grillbr-- 20-minute walk to Starfish Pointbr-- 5 miles to the nearest grocery store, Chisholm's Grocerybr-- 6.7 miles to Over the Edge restaurantbr-- 7.2 miles to Cayman Crystal Cavesbr-- 9.2 miles to our Guest Services Welcome Centerbr-- 13 miles to the nearest supermarket, Foster's Expressbr-- 26.5 miles (50 min drive) from Owen Roberts Airport (GCM)brbr***Getting Around***brA 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 Cayman, Avis, or Marshalls.brbr***Beach Notes***brAll beaches in Grand Cayman are technically public since the Crown owns up to the high watermark. Be advised, the beach or water entry behind your property may vary slightly from the images displayed due to shifting weather and tide patterns. The next-door beach is also always available for your use. We advise guests to wear foot protection (pool socks or aqua shoes) when entering the ocean to avoid injury on coral heads, ironshore, or rocks.brbr***Ocean Debris & Sargassum Seaweed***brBeaches 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. This is VERY RARE for homes along the Cayman Kai Cove.
Bed 3

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Bath 3

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Sleep 8

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