
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.

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

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.

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.

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,

Oceanfront Luxury Condo with Panoramic Views
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.

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.

Modern Oceanfront, 2Primary Suites, sleeps 6, pool
Just a 35-minute flight from Grand Cayman, this newer oceanfront home offers stunning sea views and relaxed barefoot luxury. Large windows and an open layout showcase the pool and Caribbean, connecting the kitchen, dining, and living areas. Two king suites face the ocean with tiled baths, plus a third queen room with tropical views. Travel tip: search flights to Grand Cayman first, then book the short Cayman Brac flight separately on Cayman Airways for better fares.

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.

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

Waterfront 2BR with private screened pool
Unwind in this renovated waterfront 2BR at Pools of the Kai, featuring a private screened pool and two king suites with water views. The upper suite has a private balcony, while the lower opens directly onto the pool deck. A sofa bed accommodates 2 additional guests. Walk to Kaibo, kayak to Starfish Point or explore Bioluminescent Bay. Fast Wi-Fi and peaceful Cayman Kai surroundings make it ideal for couples, families and groups of up to 6.

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!

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.
Popular amenities for Cayman Islands rentals with a pool
House rentals with a pool

Island Oasis

Sandalwood Escape Luxury Family Villa Private Pool

Coral Cottage - Beach Front w/ Private Pool

BeachPlumVilla

Oceanside Townhome with Watersports at Fingertips!

Savhaven - 4 Bed 4 Bath w/ Pool (2 mins to Beach)

3 Bedroom Beach House with Pools

Luxury 5 Bdr Ocean View Home w/ Pool + Hot Tub
Condo rentals with a pool

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

Nature's View: Pools of the Kai #2

Cayman Reef Resort on Seven Mile Beach

2 BR beach condo resort with pool and ocean views

Oceanfront 2bed 2bath Condo Seven Mile Beach

Seven Mile Beach with Soul

Blissful a Luxury Ocean Front Villa, Grand Harbour

Luxury Oceanfront Condo in Grand Cayman Paradise
Other vacation rentals with a pool

Cozy End Unit Apartment

Coastal Hideaway

4 Bedroom Apartment in Heart of Seven Mile Beach

3-Bedroom Oceanview + Pool on Seven Mile Beach

Yippee Kai Yay Beachfront oasis

Stunning Little Cayman 3 Bedroom Beach Townhouse

Casa de Bells 3

Caribbean Marine Park Retreat, Beachfront Bliss
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