Holiday houses in George Town

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Top-rated holiday rentals in George Town

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Top Guest favourite
The living area features a comfortable sofa adorned with decorative cushions. A light wooden coffee table sits on a patterned rug, and a wall-mounted TV is positioned across from the seating. Sunlight floods in through the sliding doors that open to a private patio.
Condo in George Town
4.95 out of 5 average rating, 193 reviews

Cayman Reef Resort on Seven Mile Beach

At the heart of Seven Mile Beach, our home is in the middle of everything and far from nothing. Extensively renovated and well maintained, the condo is designed for you to enjoy a tranquil beach getaway in a luxurious setting with all the comforts of home. Picture perfect views, top of the line amenities and our local touch provide a warm welcome and cozy stay. We are fully licenced and our rate includes the 13% tourist accommodation tax. 20% discount from list price for local residents!

Guest favourite
A pool area is shown with lounge chairs arranged around a clear blue pool. The deck is paved with light-colored bricks and surrounded by greenery. In the background, a covered seating area with multiple chairs can be seen, alongside colorful buildings under a sunny sky.
Condo in Grand Harbour
4.92 out of 5 average rating, 280 reviews

Waterfront Sanctuary Serene | 2BR | Pool & Porch

Cool clean contemporary Sanctuary with water views; a two bedroom/two bathroom condo with a full kitchen and living room packed with all popular amenities (wifi, cable television, Apple TV, Netflix, Playstation game console, central A/C, iron and ironing board, washer and dryer, outdoor patio, pool and free parking) - conveniently located in Grand Harbour. The Shoppes at Grand Harbour, & Harbour Walk are next door. Perfect for exploring and enjoying all that the Cayman Islands has to offer.

Guest favourite
Condo in Grand Cayman
5 out of 5 average rating, 11 reviews

Beachside Retreat - Walk to 7 Mile Beach

New Listing! Enjoy our brand-new unit at special introductory rates for a limited time. Modern renovated ground-floor 1BR/1BA — Seven Mile Beach Corridor Enjoy luxury living walking distance from Seven Mile Beach, top dining, shopping, and nightlife. Relax in the large, screened patio overlooking lush, landscaped grounds. Amenities include: - Swimming pool - 2 x beach chairs with coolers - 1 x beach umbrella - 2x beach towels - 2 x bath towels - Starter Shampoo and conditioner

Guest favourite
A screened patio is furnished with a round glass table and four woven chairs, providing a comfortable space for outdoor dining. Lush greenery is visible through the balcony railing, enhancing the view of the surrounding landscape.
Condo in George Town
4.93 out of 5 average rating, 15 reviews

Regal Beach Club #322 - 2BR Ocean View on SMB

Welcome to Regal Beach Club #322, your private haven on the world-renowned Seven Mile Beach. This beautifully designed 2-bedroom, 2-bathroom second-floor condo comfortably sleeps up to 6 guests and showcases breathtaking views of the Caribbean Sea and unforgettable sunsets from its private patio. With thoughtful touches throughout, plus access to resort-style amenities—Regal Beach Club #322 delivers the perfect blend of style, comfort, and location for your ultimate Cayman escape.

Top Guest favourite
A cozy cottage is surrounded by lush tropical greenery, with a gravel driveway leading up to it. A large blue umbrella provides shade to a seating area, complemented by a barbecue grill nearby. The inviting entrance features a wooden deck with steps leading to the door.
Home in Grand Harbour
5 out of 5 average rating, 10 reviews

Happy Place 1 Bed/1 Bath Cayman Cottage in Red Bay

Take it easy at this unique and tranquil getaway. Our simple, comfortable cottage, is the perfect place for those wanting a private, relaxing stay in Grand Cayman. It is set back from the road on a lush 2/3 acre property, in a quiet and safe neighborhood, yet just a few minutes drive to beaches and amenities. Whether you want to spend time inside cooking or watching movies, or lounging outside watching the birds, you'll find everything you need for your private retreat in paradise!

Top Guest favourite
A modern living area features a teal sofa and a circular wooden coffee table. A light rug with a minimal pattern lies beneath. The space opens to a dining area with a sleek table and chairs. Warm light is provided by stylish ceiling fixtures.
Apartment in George Town
4.96 out of 5 average rating, 45 reviews

Seaside Serenity at Allure

Affectionately dubbed the Seaside Chateau by owner and local fragrance designer Ted Green, Seaside Serenity at Allure is less Chateau and more contemporary island retreat that just happens to be nestled at the sea's edge of the North Sound (Caribbean Sea). A perfectly appointed and centrally located retreat. You will feel nestled away from it all, but in actuality, you're no farther than 5-10 mins from your favorite spots in South Sound, George Town, or Seven Mile Beach.

Top Guest favourite
A graphic featuring green leaves creates a natural backdrop for the text 'Nim's Retreat,' which is displayed in a soft blue font. The overall design emphasizes a connection to nature, indicative of the serene environment surrounding the property.
Apartment in George Town
4.99 out of 5 average rating, 75 reviews

~Nim's Retreat~ Grand Cayman BWI

Nim's Retreat is a unique dwelling designed and built by the USA based architect Rufus Nims. Nim's Retreat features two bedrooms with King size beds and two baths. It is centrally located near some of the best restaurants and dive sites on Grand Cayman. Just a short trip to Smith Cove to enjoy a quick swim and beautiful sunset. Nim's Retreat can comfortably accommodate up to six persons when using the pull-out queen sleeper sofa. The property features SONOs in each room.

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, 185 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.

Guest favourite
A tranquil swimming pool is framed by palm trees and a rocky outcrop, with clear blue water inviting relaxation. The ocean is visible in the background, where waves gently meet the shore. Lounge chairs are arranged around the pool area, creating a serene atmosphere.
Guest suite in George Town
4.96 out of 5 average rating, 279 reviews

Paradise Escape-Charming Oceanfront Guest Suite

A tranquil oceanfront escape for couples and solo adventurers... Wake-up in bed to a lovely view of a luscious green landscape that melds with the emerald green and blue ocean, sip a hot cup of coffee on the porch, enjoy a sunset cocktail by the ocean front pool, break a sweat in a friendly game of tennis, or take a blanket out to the lawn under the palm trees for breathtaking star gazing. PLEASE NOTE: WE ARE NOT LOCATED ON BATS CAVE BEACH. AIRBNB HAS THIS WRONG!

Guest favourite
The living area features a comfortable blue sofa with decorative pillows, paired with a glass coffee table atop a patterned rug. A functional kitchen is visible, equipped with modern appliances, including a refrigerator and a washer-dryer. Natural light enters through nearby windows.
Apartment in Grand Harbour
4.85 out of 5 average rating, 33 reviews

Elegant One-Bedroom Apartment in Grand Harbour

Escape to a stress-free vacation in our elegant one-bedroom apartment, nestled in the family-friendly Grand Harbour neighbourhood. With ample free parking, complimentary WiFi and a heated rooftop pool, our apartment offers all the comforts of home and the luxury of a relaxing getaway. The apartment consists of one bedroom with a queen sized bed plus a pull out queen sized sofa bed in the living area. Please note this is not a 2 bedroom apartment.

Superhost
A cozy bedroom features a spacious bed with a patterned blanket. A small television is positioned on a dresser against a wall. Natural light filters through textured window treatments, complementing the earthy tones of the decor. A comfortable chair is located nearby, adding to the inviting space.
Guesthouse in George Town
4.87 out of 5 average rating, 182 reviews

Zen Den 3, cozy private studio in George Town

Welcome to this private cozy studio in the vibrant heart of George Town! Lokated 10-15 minute walking distance to Smiths Cove Beach, this is separate unit with an independent entry. Has a bedroom, kitchenette, washer dryer, bathroom and designated parking spot. Located in George Town near hospitals, pharmacy, gas station and restaurants. Bedroom has queen bed, split A/C, smart TV and Internet. Private outside patio with seating and a hammock.

Top Guest favourite
An airy living area is depicted with a spacious couch, a coffee table, and a dining area featuring light-colored chairs. Large windows offer views of palm trees and the beach, while natural light brightens the room, creating a fresh and inviting atmosphere.
Condo in George Town
4.97 out of 5 average rating, 103 reviews

Oceanview 2BR Condo w/ Big Balcony on 7 Mile Beach

Stylish, spacious, and steps from the sea—Cocoplum 10 is a renovated 2-bedroom, 2-bath condo with ocean views, coastal-modern interiors, and a large private balcony overlooking the Pool and Ocean. Located on the quieter end of Seven Mile Beach, you’ll enjoy calm waters for snorkeling and paddleboarding, a beachfront pool, and easy walks to local restaurants and shops. One of the most popular 2BR condos on the island—book early!

Popular amenities for George Town holiday rentals