Vacation rentals with a pool in Cayman Islands

Find and book unique homes with a pool on Airbnb

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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Top guest favorite

An aerial view reveals a resort-style pool surrounded by lush greenery and tropical plants. Several shaded lounge areas with dark umbrellas and seating are arranged near the water. A heated spa sits adjacent to the pool, enhancing the serene outdoor environment.

Cottage in West Bay

4.99 out of 5 average rating, 310 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 favorite

A serene pool area is surrounded by a landscaped patio featuring palmy greenery. The pool is seamlessly integrated with the outdoor clubhouse, which is framed by tall columns and a light-colored roof. Lounge chairs are positioned nearby for relaxation.

Condo in Grand Harbour

4.93 out of 5 average rating, 269 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 favorite

A large swimming pool is surrounded by well-maintained greenery and palm trees. Blue lounge chairs and umbrellas are positioned by the poolside, providing ample shade and relaxation options. The backdrop features a contemporary condo complex with balconies overlooking the grounds.

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 favorite

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

4.87 out of 5 average rating, 157 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 favorite

An outdoor dining area features a large wooden table surrounded by metal chairs, with panoramic views of the ocean framed by retractable glass doors. Sun loungers and a hammock are positioned on sandy ground, providing a serene connection to the beach and lush greenery.

Home in Bodden Town

5 out of 5 average rating, 57 reviews

Casa Avi - Paradise by the Sea

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.

Superhost

A clear blue swimming pool is surrounded by a well-maintained patio area. Two lounge chairs are positioned beside the pool, with lush greenery in the background. Bright, sunny skies and a modern building can be seen beyond the pool area.

Condo in George Town

4.84 out of 5 average rating, 132 reviews

Cozy Condo near Seven Mile Beach!

Welcome to the Cozy Condo, the spot for everyone coming to Grand Cayman for work, play, or a little bit of both—all at a budget-friendly price! You’ll love our prime location, just minutes from the George Town, the lively Camana Bay, and the beautiful Seven Mile Beach. Plus, you’ll find two convenient supermarkets and pharmacy within easy walking distance or a quick drive which has everything you could want, from shopping and dining to entertainment and drinks. We can’t wait to to host you!

Top guest favorite

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, 251 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 favorite

An aerial view reveals two distinct pools: a freshwater infinity pool and a sea pool, both adjacent to rocky shorelines. The crystal-clear waters extend towards the ocean, highlighting the natural beauty of the surrounding landscape and the well-planned layout of the modern condo.

Condo in West Bay

4.96 out of 5 average rating, 51 reviews

Modern Penthouse Oceanfront 1 Bdr Condo /w Pool

Welcome to this stunning, newly built oceanfront condo that boasts breathtaking and uninterrupted views of the sea from the living room, kitchen, and bedroom. Whether you choose to admire the scenery from the stylish and modern interior or step outside onto the expansive patio area, you'll be captivated by the beauty that surrounds you. This spacious one-bedroom, one-bathroom condo featuring sleek and modern accents and furnishings offers ample comfort and convenience for your stay.

Top guest favorite

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, 48 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.

Top guest favorite

An infinity pool extends towards the ocean, merging seamlessly with the water's edge. Natural rocky formations are visible nearby, creating a rugged contrast against the serene sea. The sky is partly cloudy, allowing for glimpses of bright blue between the clouds.

Condo in West Bay

5 out of 5 average rating, 84 reviews

Oceanfront: 2 pools, diving & snorkeling on-site

This beautiful oceanfront condo boasts unique wood furniture and accents paired with soothing neutral tones, creating an atmosphere of warmth and elegance. Large glass doors allow for stunning views and natural light to flood the spacious living area, while electric blinds provide privacy. With meticulous attention to detail, this one-bedroom, one-bathroom home offers a serene retreat for those seeking coastal charm and sophistication.

Top guest favorite

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

4.97 out of 5 average rating, 178 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!

Guest favorite

A private pool is surrounded by sun loungers and tropical palms, with a clear blue sky overhead. The pool features a gentle curve and steps leading in, offering a serene space for relaxation and enjoyment near the ocean.

Condo in George Town

4.98 out of 5 average rating, 87 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!