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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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Guest favorite
A modern living space features a light-colored sofa adorned with decorative pillows and a cozy blanket. A wooden coffee table is placed on a textured area rug, surrounded by greenery from a tall indoor plant. Large glass doors lead to a balcony, allowing in natural light.
Apartment in West Bay
4.88 out of 5 average rating, 101 reviews

New, Luxury 1 Bed/ 1 Bath At 7 Mile Beach

Discover the perfect beachside retreat in our newly furnished 2nd floor apartment, just steps away from the beach. Indulge in the modern amenities, including a Smeg oven, dishwasher, and KitchenAid utensils, as well as a flat screen TV and high-speed fiber WiFi. The spacious living room and dining area provide ample space for relaxation. Unwind in the king-sized bed with a brand new hybrid mattress and luxury pillows, adorned with premium Brooklinen sheets. The modern bathroom features a refresh

Top guest favorite
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, 365 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
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, 194 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!

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
4.96 out of 5 average rating, 285 reviews

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.

Guest favorite
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
4.92 out of 5 average rating, 286 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 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.
Condo 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 favorite
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.
Vacation home in Bodden Town
5 out of 5 average rating, 108 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 favorite
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, 161 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!

Superhost
Apartment in Seven Mile Corridor
4.85 out of 5 average rating, 122 reviews

Modern 1BR Apartment – Steps to Seven Mile Beach

Experience modern island living in this bright one-bedroom apartment, perfectly located in the Seven Mile Beach Corridor of Grand Cayman. Just a 2-minute walk to Governors Beach and a short drive from Owen Roberts International Airport, it’s your ideal Cayman Islands getaway. Enjoy a private bathroom, kitchenette, high-speed Wi-Fi, workspace, and free parking. Relax in a peaceful, secure setting at Governors Village - your home away from home in paradise.

Superhost
Home in Grand Cayman
4.9 out of 5 average rating, 30 reviews

Pools of the Kai #6 by Grand Cayman Villas

Relax under your own private, screened pool atrium at Pools of the Kai #6, a renovated 2-bedroom waterfront condo with all the island vibes. This tropical retreat offers a private pool with stunning water views, perfect for couples or families seeking a quiet getaway. Prime island experiences are just steps away: walk barefoot to The Kaibo for sunset drinks, snorkel the pier at Rum Point Club, explore Starfish Point, or take a kayak tour of the Bio-Bay.

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
4.96 out of 5 average rating, 193 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!

Top guest favorite
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 in George Town
4.97 out of 5 average rating, 104 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!

Popular amenities for Cayman Islands rentals with a pool