
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.

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

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!

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.

3-Bedroom Condo with ocean view
Experience luxury at its best with this beautiful new condo on Seven Mile. Featuring stunning ocean views, sunsets, spacious living spaces. This charming property features 3 bedrooms with 1 king bed and 2 queen beds, perfect for a group of friends or family, living areas with large windows to take in the natural beauty of the Caribbean. Amenities include a swimming pool, hot tub, fitness center, parking, rooftop lounge. Ideal for vacation or year-round living. Book your dream vacation today!

Oceanfront Sunset Patio w/ BBQ + Pool, Gym & Spa
Welcome to Sunset Point #29 — a brand-new 1-bedroom, 1.5-bath oceanfront condo in Grand Cayman’s quiet North West Point. This 1,016 sq ft ground-floor retreat features floor-to-ceiling windows, a private patio with Weber grill, and the island’s best sunset views. Relax by the oversized pool and spa, work out in the fully equipped gym, or stroll 2 minutes to Macabuca for world-class diving, cocktails, and Cayman sunsets. Perfect for couples or small families seeking style and serenity.

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!

Sunset Point Oceanfront Luxury
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 Sanctuary Cove 2BR King Bd Pool Porch
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.

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!

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.

Oceanfront - On-Site Diving, Snorkeling & Dining
Enjoy our new unit at special reduced prices. Escape to this stunning oceanfront condo with magnificent views. Dive right into crystal-clear water with direct access from a natural sea cove pool, perfect for diving and snorkeling in one of the island’s best spots. Divetech is a full-service dive shop, conveniently located on-site offering both shore and boat dives. Vivo restaurant is also onsite with delicious meals and drinks with beautiful sunsets!

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

Luxury 3bd Beach Front, # 5 Yellow, Stunning Views

Beachfront Retreat w/ Pool – Rum Point Paradise

Oceanfront Oasis Home with cottage & private pool

Gorgeous 3 Bed Brand New by 7 Mile Beach

BeachPlumVilla

Island Oasis

Modern Oceanfront, 2Primary Suites, sleeps 6, pool

Willow Beach by Grand Cayman Villas
Apartment rentals with a pool

Oceanfront: 2 pools, diving & snorkeling on-site

Bougainvillea at Pappagallo Beach Villas (condo#2)

Starfish Paradise Beachfront Condo

Cozy Condo near Seven Mile Beach!

Seven Mile Beach with Soul

Beautiful Modern Condo on 7 Mile Beach

Sunset Hideaway (3)

2 BR beach condo resort with pool and ocean views
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Condo-Sunset Cove-Ocean | Pool | Seven Mile Beach

Sunset Cove Condo on Seven Mile Beach - 2bed/2bath

2 bedroom condo with pool close to beach

Oceanfront Condo on Seven Mile Beach
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