Holiday rentals with a pool in Cayman Islands

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Top-rated rentals with a pool in Cayman Islands

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

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Guest favourite
Apartment in West Bay
5 out of 5 average rating, 13 reviews

Oceanviews-Restaurant, Diving & Snorkeling on site

New Oceanfront Penthouse at reduced rates. Relax in this calm, stylish space with ocean views that is never ending. Snorkeling and diving, right at your doorstep. A natural sea cove pool offers easy access to calm, crystal-clear waters — perfect for swimming, snorkeling, or shore diving. The reef lies within a marine protected area, teeming with a variety of vibrant marine life. For divers, Divetech, a full-service dive shop located on-site, provides equipment rentals, shore dives, and daily

Top guest favourite
A modern two-story home features expansive glass doors and large windows that provide views of the outdoor space. A private pool and putting green are surrounded by lush landscaping, creating a refreshing environment. Lounge chairs are positioned nearby for relaxation.
Home in North Side
5 out of 5 average rating, 27 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, 357 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 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.
Apartment in George Town
4.95 out of 5 average rating, 192 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 showcases the resort's layout, featuring a large pool surrounded by lush greenery and palm trees. The pool's inviting shape contrasts with the sandy beach that gently meets the turquoise water. Loungers and umbrellas are positioned along the beach for relaxation.
Apartment in George Town
4.87 out of 5 average rating, 174 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, 67 reviews

Casa Avi - Your Calm Coastal Gem

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 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.
Apartment 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
A comfortable seating area features a neutral-toned sofa and a green armchair. A coffee table with a textured surface is positioned in front. Large glass doors reveal a view of palm trees and the ocean, allowing natural light to brighten the space. A television sits on a light media console.
Apartment in George Town
4.91 out of 5 average rating, 101 reviews

Beautiful Beachfront 2BR Condo.

Our place is right on the beach, with close nightlife and the Warf, and other shopping and family-friendly activities. You’ll love the place because of the updated kitchen, beautiful view from the screened in patio, the comfy bed, and the touches of home and coziness. Our place is good for couples, solo adventurers, business travelers, and families (with kids). There is a community pool to relax and have a soak or simply enjoy the water of the ocean. Also, community grill and gazebo for use.

Top guest favourite
A serene view of the turquoise ocean stretches beyond a well-maintained pool area. Lush palm trees and vibrant greenery frame the space, with a sandy beach visible nearby. The outdoor seating area is partially shaded, creating a relaxing atmosphere for guests.
Holiday home in Bodden Town
5 out of 5 average rating, 105 reviews

Art Beach House, boutique style luxury.

Private getaway for couples or singles perfect for honeymooners situated at beautiful frank sound. 25 mins from George town so car essential, many attractions nearby include the crystal caves 5 mins botanical gardens and rum point, and the beautiful east end. we also boast some of the the best dining on island. So lots to do or just chill on your private beach away from the crowds. the apartment is situated on ground floor level with art studio/Gallery above. with exclusive use of pool,

Top 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.
Flat in George Town
5 out of 5 average rating, 12 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

Top 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.
Apartment in Rum Point
4.94 out of 5 average rating, 158 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
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, 277 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!

Popular amenities for Cayman Islands rentals with a pool