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Holiday rentals with a pool in Grand Cayman

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Grand Cayman

Guests agree: These homes with a pool are highly rated for location, cleanliness and more.

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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, 318 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

Top 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
4.93 out of 5 average rating, 271 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
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, 186 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!

Top Guest favourite
An aerial view shows a large pool area surrounded by lush greenery and sandy beach. The pool features a curved shape with a bridge and is furnished with multiple lounge chairs and umbrellas. Clear blue water meets the gentle waves of the Caribbean Sea.
Condo in George Town
4.88 out of 5 average rating, 160 reviews

Grandview condominium directly on 7-mile beach

This family friendly condo is close to restaurants and dining, the beach, family-friendly activities, nightlife, and public transport. You’ll love this place because of the location, the people, the ambiance, the outdoors space, and the neighborhood. My place is good for couples, solo adventurers, business travelers as well as families with children. The property has biggest pool on Seven Mile Beach and hot tub overlooking beach with best sunsets. It also offers tennis courts and Basketball.

Top Guest favourite
A spacious living area features large glass windows that provide panoramic ocean views. A balcony extends off the room, allowing direct access to the tranquil outdoors. A dining area is visible in the foreground, complementing the bright and airy design.
Home in Bodden Town
5 out of 5 average rating, 58 reviews

Casa Avi - Secluded Slice of Heaven - Grand Cayman

Discover Casa-Avi an idyllic beach front oasis nestled in sea-grape trees and secluded on the edge of Bodden Town. Immerse yourself in elegant king size bedrooms, breathtaking ocean views, and art-infused living spaces curated by renowned artist Avril Ward. Savor panoramic ocean views from retractable sliding doors, enjoy direct beach access for kayaking and snorkeling adventures. Downstairs, simply unwind in the embrace of hammocks while you BBQ and refresh in the private saltwater pool.

Guest favourite
A modern living area features large windows offering expansive ocean views. A light-colored sectional sofa is paired with a round woven coffee table, while a neutral rug anchors the space. A wooden sideboard and stylish armchair complement the airy atmosphere.
Apartment in George Town
5 out of 5 average rating, 19 reviews

3-Bedroom Condo with ocean view

Experience luxury at its best with this beautiful new condo on Seven Mile. Featuring stunning ocean views, sunsets, spacious living spaces. This charming property features 3 bedrooms with 1 king bed and 2 queen beds, perfect for a group of friends or family, living areas with large windows to take in the natural beauty of the Caribbean. Amenities include a swimming pool, hot tub, fitness center, parking, rooftop lounge. Ideal for vacation or year-round living. Book your dream vacation today!

Top 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
4.98 out of 5 average rating, 255 reviews

Paradise Escape-Charming Oceanfront Guest Suite

A tranquil oceanfront escape for couples and solo adventurers... Ours is a unique community with quaint freehold condo cottages on a vast tract of oceanfront land. 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.

Guest favourite
A large swimming pool is framed by lush palm trees and tropical landscaping. Lounge chairs are arranged around the pool area, providing spaces for relaxation. The clear blue water reflects the sky, and stepping stones lead into the pool, enhancing the inviting outdoor environment.
Apartment in George Town
5 out of 5 average rating, 5 reviews

Kings Court Villa Britannia

Ground floor, spacious, modern and bright 2 bed and 2 bath canal front condo in Kings Court Britannia. Features a brand new custom wood kitchen , fitted laundry room, custom bar and extended patio. open plan living, dining and kitchen area with canal and garden views. comes with allocated parking, 24 hour security, outdoor kitchen, large pool and hot tub and beautifully landscaped gardens. located on the seven mile beach corridor and walking distance to Camana Bay and Seven Mile Beach

Guest favourite
A modern living space is shown, featuring a comfortable sofa and a light wood coffee table. Bar stools are arranged at a kitchen counter, with a fully equipped kitchen visible in the background. A ceiling fan circulates air, and a warm, inviting atmosphere is created by pendant lighting.
Apartment in West Bay
4.94 out of 5 average rating, 53 reviews

Coastal Hideaway

This charming 1-bedroom retreat is in a convenient neighborhood, minutes from beaches, restaurants, and attractions. Bright and inviting, it features a comfy queen bed, a beautifully decorated living area, and a fully-equipped kitchen. Enjoy your private patio for morning coffee or an evening drink, plus a shared pool and lush gardens. With Wi-Fi, TV streaming, and air conditioning, it’s all set for a comfortable stay. Perfect for exploring and unwinding in the Cayman Islands.

Guest favourite
An outdoor dining area is presented under a vibrant teal umbrella, featuring a glass-top table surrounded by several green chairs. The view beyond includes sandy beach and the Caribbean Sea, framed by palm trees and coastal vegetation.
Condo in Rum Point
4.94 out of 5 average rating, 147 reviews

Nature's View: Pools of the Kai #2

Discover the peaceful Caribbean paradise of Cayman Kai. This secluded oasis will put you at ease as soon as you walk through the door. Our beach front property features stunning views across the Caribbean Sea to an unspoiled nature reserve. The double story screened in private pool deck can't be beat. Perfect for family holidays or a romantic getaway. Savor heavenly mornings and sundowners on your master bedroom balcony. Stroll down the beach to Kaibo, true barefoot living!

Guest favourite
An open-concept living area features a spacious sectional sofa facing the ocean. Large glass doors provide panoramic sea views and natural light. A dining area is positioned nearby, complemented by contemporary lighting fixtures. Stylish barstools and a kitchen island offer additional seating options.
Apartment in West Bay
5 out of 5 average rating, 10 reviews

Sunset Point Oceanfront Luxury

Bask in panoramic Caribbean views from this brand-new 3-bedroom, 3-bathroom waterfront condo in Grand Cayman​. This luxury retreat blends modern design with effortless island living. Floor-to-ceiling glass doors open onto a 35-foot oceanfront balcony, blurring the lines between indoors and out​. Whether you’re sipping morning coffee listening to the waves or toasting with sunset cocktails on the terrace, this condo promises a clean, inviting, and luxurious Caribbean escape.

Guest favourite
Apartment in George Town
5 out of 5 average rating, 16 reviews

Luxury 2BR Condo | Walk to Seven Mile Beach, Pools

Enjoy upscale island living in this stylish 2BR/1BA condo, just a short walk from Seven Mile Beach. With a King and Queen bed, full kitchen, washer-dryer, Wi-Fi, and central A/C, it blends comfort and convenience. Relax on your private balcony overlooking the pool and canal, or explore the gated community’s 3 pools, hot tub, gym, and clubhouse. Perfectly located for beach days, dining, and nightlife, this is your ideal Cayman escape.

Popular amenities for Grand Cayman rentals with a pool