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Holiday houses in Cayman Islands

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Top-rated holiday rentals in Cayman Islands

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Luxe
Home in North Side
5 out of 5 average rating, 35 reviews

Luxury Beachview Retreat, Cayman Island.

Luxurious, four bedroom, four and a half bath home with ensuite bathrooms and a half bath for guest. All bedrooms provide a private balcony with stunning oceanviews. This modern gated home in Northside is only 40mins from the airport and features a private pool, public beach access and a mini-golf course. BEDS Master on upper level has a king bed Second bedroom on upper level has a queen bed Third bedroom on upper level has 1 full bed and 3 twins Fourth bedroom on lower level has a queen bed.

Top Guest favourite
The exterior of the cottage is framed by vibrant tropical plants and flowering shrubs, showcasing a blend of lush greenery and colorful blooms. The white structure features a sloping roof, supported by two elegant columns at the entrance.
Cottage in West Bay
4.99 out of 5 average rating, 375 reviews

Luxury Cottage, 1bd/1ba steps to Pool+7 Mile Beach

Our Queen Cottages are part of the Botanica collection of award winning island style cottages. This unit has a private outdoor dining and garden shower. At Botanica, our focus is on casual luxury, dreamy details and high end amenities. Property highlights includes a resort style pool with heated spa set in a tropical oasis. We also offer a complimentary shuttle in our vintage Land Rover Defender to nearby beaches. Be sure to check out our other listings under my profile. Non Smoking Complex

Guest favourite
The studio apartment features a spacious bed adorned with a light blanket, accompanied by a round dining table and four chairs. Natural wood paneling enhances the ceiling, while decorative wall pieces and patterned kitchen tiles add character to the space.
Apartment in Grand Cayman
4.96 out of 5 average rating, 171 reviews

Adorable Boho-Style Beach Villa

This adorable studio apartment has been fully renovated & has everything you need to enjoy the perfect Caribbean getaway. Calypso Cove is directly across from the famous Seven Mile Beach, where you can swim in the crystal clear blue sea every day. The studio has a balcony so you can enjoy the sunset or a morning coffee. Walking distance to supermarket, restaurants, bank and pharmacy, this apartment is in the perfect location. Keurig coffee machine, deck chairs, fins and mask and beach umbrella.

Guest favourite
A screened-in patio features a colorful area rug and seating arrangement with patterned cushions. A ceiling fan is visible above, while views of the lush garden and cove are framed by large glass panels. Kayaks and lounge chairs are positioned outside, enhancing the outdoor atmosphere.
Apartment in Cayman Kai
4.93 out of 5 average rating, 229 reviews

Rum Cove on the Bioluminescent Bay with Ocean View

Welcome to Rum Cove – your private escape on the bioluminescent bay, just steps from the world-famous Rum Point. This bright & breezy 1-bedroom retreat is part of a charming triplex and offers stunning 360° views. Whether you’re relaxing on the patio, kayaking under the stars, or sipping coffee at sunrise, Rum Cove surrounds you with natural beauty & peace. A perfect space for couples, solo travelers or small families looking for a quiet getaway with the best of Cayman Kai on your doorstep.

Top Guest favourite
Cottage in East End
4.98 out of 5 average rating, 121 reviews

Hidden Gem Cottage on the Beach

Hidden Gem is a Traditional Cayman Style cottage located at Grapetree Cove on a beautiful beach area in sleepy fishing village of East End. The property is filled with trees that gives it a dreamy Island ambiance. The Cottage has been fully renovated with modern amenities that makes is very comfortable and homey. Hidden Gem offers a unique CaymanKind experience from a Caymanian host that knows the area well. Located minutes away from local dinning places and many key attractions in the area.

Top Guest favourite
Home in Rum Point
4.94 out of 5 average rating, 34 reviews

Whispering Kai: beach home on Bio Bay, Cayman Kai

A quiet oasis with unforgettable views. Located directly on the Bioilluminesce Bay in the wonderful residential area of Cayman Kai is our luxurious yet comfortable 2 bedroom, 2 bathroom secluded beachfront home complete with a spacious screened-in back patio overlooking the water on a white sandy beach with a private boat dock. Check us out on Insta: @whisperingkai Master Bedroom: King Bed Guest Bedroom: King Bed plus two pull-out sofas (twins) Living Room: One pull-out sofa (double)

Top Guest favourite
The exterior of the studio apartment is framed by lush greenery and flowering plants. An outdoor dining set with an umbrella is positioned on a blue deck. The building features large windows and light-colored walls, complemented by stone accents and manicured landscaping.
Guesthouse in Grand Harbour
4.97 out of 5 average rating, 190 reviews

Heavenly Suite 2 - The M @ The Edge

Heavenly Suíte #2 at The M @ The Edge is a studio apartment with sleek & modern furnishings, smart HD TV, sound bar, chandeliers, state of the art kitchenette with quartz counter-tops, Delta faucet, and under counter lights. The chic bedroom fashioned in white crisp tiles, scones and recessed lighting mimics the luxurious bath styled in porcelain & Carrera tiles, Delta faucets, mirrors. . The patio enlivened by red/white accents, greenery, bar, pergolas, and Jacuzzi.

Top Guest favourite
Two wooden chairs are positioned on a sandy beach, surrounded by lush palm trees. The tranquil ocean stretches out in the background, with gentle waves lapping at the shore. Bright greenery and tropical plants enhance the natural setting.
Cottage in East End
4.99 out of 5 average rating, 118 reviews

Piece of Mine, Beachfront Villa #3

Private & Tranquil BEACHFRONT Cottage offers all the conveniences of a luxury home. KAYAKS and SNORKELING GEAR, daybed & smart TV on the SCREENED PORCH, beach chairs, beach swing, and beautiful SUNSETS. Hammocks are throughout the property. Modern walk-in Shower, Towels, and bathrobe. Full Kitchen, Keurig & regular coffee maker & Blender, Extra-large bedroom, Caribbean Antique four-post bed, Desk + smart TV. Enjoy paradise & experience "True Caymanian Hospitality!!"

Top Guest favourite
The outdoor area features a large swimming pool with a built-in jacuzzi, surrounded by lounge chairs and tropical vegetation. A shaded cabana is visible, providing an area for relaxation with ocean views beyond. The clear blue water and bright sky create a serene atmosphere.
Home in Stake Bay
5 out of 5 average rating, 75 reviews

Modern Oceanfront, 2Primary Suites, sleeps 6, pool

Just a 35-minute flight from Grand Cayman, this newer oceanfront home offers stunning sea views and relaxed barefoot luxury. Large windows and an open layout showcase the pool and Caribbean, connecting the kitchen, dining, and living areas. Two king suites face the ocean with tiled baths, plus a third queen room with tropical views. Travel tip: search flights to Grand Cayman first, then book the short Cayman Brac flight separately on Cayman Airways for better fares.

Top Guest favourite
A modern kitchen is featured, designed with blue cabinetry and a dark countertop. Stainless steel appliances are present, including a refrigerator and a stove. Shelves hold various dishware, while a cozy seating area with a colorful cushion adds warmth to the space.
Apartment in Grand Cayman
4.88 out of 5 average rating, 125 reviews

Paradise Pointe Rentals (Apt 9 1st floor)

Spend your vacay in West Bay with us ! Warm tropical breezes and spectacular azure ocean views await you at Paradise Pointe. This cozy apartment is situated on the northwest point coast overlooking world famous Seven Mile Beach. If you're a swimmer, snorkeler or diver, our backyard was created especially for you. In the evenings, the amazing Caribbean sunset slowly fades as the speckled lights of Seven Mile Beach create an ambiance of quiet soothing peace.

Top Guest favourite
The image showcases a newly constructed house adjacent to a semi-private pool. Sunlight reflects off the clear water, while lush greenery frames the surroundings. A patio area features tile flooring and planters, enhancing the outdoor space for relaxation and enjoyment.
Home in Little Cayman
4.96 out of 5 average rating, 195 reviews

Just Chillin in Little Cayman

Just Chillin is a new 2 bedroom house that connects to a semi private pool, with queen size bed in both bedrooms, it is close to the airport, store and restaurants, the true Island life. Little Cayman is One mile wide and 10 miles long, we also provide bikes if you’re adventurous, our waters are blue and crystal clear for the divers and People that like to snorkel, it is Paradise, and tranquility for the people that just want to chill!

Top Guest favourite
A charming white cottage features a wooden front door with a cross design, flanked by blue potted plants. Lush green foliage surrounds the stone pathway leading to the entrance, while large windows provide a view of the inviting interior.
Cottage in Savannah
4.94 out of 5 average rating, 235 reviews

John John's Hideaway

Cozy 1 bedroom cottage with en-suite bathroom, sitting area, full kitchen, washer and dryer. Located in a quiet neighbourhood, a 2 minute walk away from Pedro St. James Castle. 3 minute drive from a supermarket and local restaurants. 5 minute drive to snorkel at the picturesque Spotts Beach. 20 minute drive from other popular destinations, including shopping centres and other local attractions.

Popular amenities for Cayman Islands holiday rentals