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.

1 of 1 pages1 / 1

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

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

4.99 out of 5 average rating, 412 reviews

Top Guest favourite

A private pool is framed by a wooden deck, offering views of the Caribbean Ocean. Bright blue lounge chairs are positioned nearby, alongside palm trees swaying in the gentle breeze. The turquoise water of the ocean contrasts with the sandy beach in the background.

Home in Rum Point

No Big Ting - Private Beach Home

Entering No Big Ting you're immediately greeted with stunning views of the beautiful Caribbean Ocean. It's all about outdoor living, from the spacious screened porch to the soft sandy beach. Cool off in the private pool or adventure out to the protected reef to snorkel with the abundant sea life. End a perfect day star gazing on the deck listening to the waves under the moonlight. No Big Ting delivers a tranquil ocean vibe and is the ultimate beachfront oasis to relax with family and friends.

5.0 out of 5 average rating, 19 reviews

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

Paradise Escape-Charming Oceanfront Guest Suite

A tranquil oceanfront escape for couples and solo adventurers... Wake-up to a lovely view of a luscious landscape that melds with the emerald green and blue ocean, sip a hot cup of coffee on the porch or enjoy a sunset cocktail by the ocean front pool. Accuracy Disclaimer Important: Airbnb currently displays an incorrect message stating this home is “Right on Bats Cave Beach.” The property is located near Spotts Beach, approx a 1-min drive away. Bats Cave Beach is private and not accessible.

4.97 out of 5 average rating, 304 reviews

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

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,

5.0 out of 5 average rating, 114 reviews

Top Guest favourite

An infinity pool reflects the vibrant colors of the sunset over the sea, surrounded by palm trees. Three transparent float loungers gently rest on the water's surface, creating a serene atmosphere. The calm ocean horizon is visible in the background, complementing the tranquil setting.

Home in Old Man Bay

Coral Cottage - Beach Front w/ Private Pool

Coral Cottage – Luxury Beachfront Retreat with Private Pool & Sea Views Old Man Bay, Grand Cayman | Sleeps 6 | 3 Bedrooms | 3 Bathrooms | Escape to your own slice of paradise. Nestled on the pristine beachfront of Old Man Bay, North Side. Coral Cottage is a stylish semi-detached villa offering the perfect blend of Caymanian charm and upscale comfort. With panoramic sea views, a private saltwater infinity pool, and lush gardens for al fresco dining, this is island living at its finest.

5.0 out of 5 average rating, 32 reviews

Top Guest favourite

An aerial view captures the well-maintained grounds of a beachfront property, featuring a central pool surrounded by loungers. Tall palm trees offer shade, while the pristine sand and turquoise ocean provide a scenic backdrop, emphasizing the property's proximity to the beach.

Apartment in Seven Mile Beach

3-Bedroom Oceanview + Pool on Seven Mile Beach

Unit 35 at Plantana is a 3-bedroom ocean view condominium for 7 guests located directly on the best part of Seven Mile Beach. Enjoy walking distance to all the newest shops and restaurants and relax in the gorgeous ocean-front pool with plenty of beach umbrellas and loungers on the widest and most beautiful section of Seven Mile Beach. We provide all toiletries, soft cotton linens, and a no-cost mid-stay beach towel refresh. The kitchen is newly renovated with all new appliances.

5.0 out of 5 average rating, 24 reviews

Guest favourite

Condo in Grand Harbour

Waterfront Escape | King Suite + Pool + Walkable

Enhance your getaway experience in our meticulously clean, spacious, and tranquil retreat. Immerse yourself in serenity, surrounded by picturesque water views and a lush tropical landscape that will effortlessly melt your worries away. Ideally situated, our Sanctuary offers not just a stay, but a rejuvenating escape into nature's embrace. Come find your peace in this beautifully designed space, where every detail is crafted for your ultimate relaxation and enjoyment.

4.88 out of 5 average rating, 128 reviews

Top Guest favourite

A serene ocean view captures calm turquoise waters meeting the sky, dotted with fluffy white clouds. The image features a rocky shoreline with a concrete dock extending into the water, surrounded by lush greenery and picturesque coastal scenery.

Condo in West Bay

Oceanfront- Restaurant,Diving & Snorkeling on site

Magnificent Oceanfront condo Relax in this calm, stylish space with breathtaking ocean views. There is a natural sea cove pool with access for diving/snorkeling and one of the best house reefs on the island. The reef is in a marine protected area abundant in sea turtles, small marine life, parrot fish, and rays. Divetech, a full service dive shop, is conveniently located on site and offer shore as well as boat dives. Vivo restaurant is also located on site.

4.95 out of 5 average rating, 110 reviews

Guest favourite

Apartment in Grand Cayman

The Grove Too - 1 Bedroom Apartment

The one-bedroom suite at The Grove Too offers refined island elegance with generous living space, designer furnishings, and a private balcony overlooking our beautiful garden. Ideal for couples or solo travelers, the suite features a fully equipped kitchen, spa-inspired bathroom, and access to all resort-style amenities including the rooftop pool and personalized concierge services. To take a virtual tour of the unit please visit our website

4.96 out of 5 average rating, 67 reviews

Guest favourite

A contemporary living area features a sleek white countertop that overlooks a spacious seating arrangement. Large glass doors provide views of the outdoor pool and lush greenery, while pendant lighting adds a modern touch to the bright space.

Apartment in George Town

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.

4.96 out of 5 average rating, 50 reviews

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

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!

4.97 out of 5 average rating, 119 reviews

Top Guest favourite

A spacious living area is furnished with a light grey sectional sofa and a circular coffee table. A large flat-screen television is positioned on a wooden media console. Natural light floods in through glass doors, which lead to a balcony with views of greenery, enhancing the inviting ambience.

Apartment in George Town

2 Bedroom 2 Bathroom Condo 7 Mile Beach

The apartment was previously used by us as a home. It has everything you need for a relaxed vacation. It is located on the northern side of the complex with a pleasant peaceful garden view yet close to the action on the Seven Mile Beach corridor where Camana Bay, the nightlife and famous Seven Mile Beach are located. The amenities of the complex are a short walk away.

4.9 out of 5 average rating, 111 reviews