
Holiday 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

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

Blissful a Luxury Ocean Front Villa, Grand Harbour
Experience Blissful, your luxurious getaway in the charming Allure community of Grand Harbour. This stylish 3-bedroom condo boasts modern comforts and features a fully-equipped kitchen, pool, and stunning ocean views. With supermarkets, a wide range of dining options and outdoor activities just minutes away, Blissful offers an unbeatable blend of convenience, relaxation and value. Whether you're here for adventure or relaxation, our condo provides the perfect unforgettable stay in Grand Cayman.

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.

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!

Oceanfront 3BR Sea Haven – Cassava Point Villa 4D
Cassava Point Villa 4D is a stunning 3 bedroom, 2.5 bath, two story oceanfront smart home villa with sweeping waterfront views in the Prospect/Sea Haven area. Overlooking the tranquil North Sound and surrounding waterways, it blends luxury finishes with a warm, welcoming feel in a quiet, family friendly dead end enclave. It’s an ideal choice for up to 6 guests seeking a peaceful, water oriented Cayman retreat with dock access, pool, and easy access to the island’s beaches and attractions.

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.

Waterfront Sanctuary | King Suite | 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.

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- 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.

Luxury 3 Bedroom Waterfront Condo in Paradise
Modern 3BR/3BA waterfront home offering luxury, comfort, and uninterrupted ocean views. Enjoy morning coffee as waves roll in and end your day sipping wine with breathtaking Caribbean sunsets off your private patio area. The complex features a pool, hot tub, gym and lounge areas, all set in a welcoming neighbourhood just a 2-minute walk to Cayman’s favourite tiki bar. A stylish retreat perfect for families, couples, or friends seeking a refined island stay.
Popular amenities for Cayman Islands rentals with a pool
House rentals with a pool

Luxury 3bd Ocean View, # 1 Cream, Stunning Views

Oceanfront Oasis: Endless Views, Pool & Cottage

Sandalwood Escape Luxury Family Villa Private Pool

Modern Oceanfront, 2Primary Suites, sleeps 6, pool

Gorgeous 3 Bed Brand New by 7 Mile Beach

Willow Beach by Grand Cayman Villas

Coral Cottage - Beach Front w/ Private Pool

Oceanside Townhome with Watersports at Fingertips!
Apartment rentals with a pool

Beautiful oceanfront condo in peaceful North Side

2 BR beach condo resort with pool and ocean views

Seven Mile Beach with Soul

Oceanfront 2bed 2bath Condo Seven Mile Beach

Nature's View: Pools of the Kai #2

Beautiful Beachfront 2BR Condo.

Sunset Hideaway (2)

Oceanfront Luxury Condo w/ Private Garden
Other holiday rentals with a pool

Tropical Chic 3BR Gardenview Condo w/ Pool & Beach

Oceanfront: 3 King Suites, Pool, Shore Diving

Amazing Penthouse with Spectacular sea views

Kings Court Villa Britannia

Luxurious Penthouse Condo

Exotic Poolside Condo

Humble and Polite Little Cayman

Coastal Hideaway
Destinations to explore
- House rentals Cayman Islands
- Villa rentals Cayman Islands
- Apartment rentals Cayman Islands
- Rentals with outdoor seating Cayman Islands
- Serviced apartment rentals Cayman Islands
- Rentals with a washing machine and dryer Cayman Islands
- Rentals with a hot tub Cayman Islands
- Rentals with a kayak Cayman Islands
- Family-friendly rentals Cayman Islands
- Luxury rentals Cayman Islands
- Smoking-friendly rentals Cayman Islands
- Fitness-friendly rentals Cayman Islands
- Cottage rentals Cayman Islands
- Flat rentals Cayman Islands
- Guest house rentals Cayman Islands
- Townhouse rentals Cayman Islands
- Beach apartment rentals Cayman Islands
- Rentals with beach access Cayman Islands
- Beachfront rentals Cayman Islands
- Rentals with a firepit Cayman Islands
- Rentals with an EV charger Cayman Islands
- Rentals with a patio Cayman Islands
- Hotel rooms Cayman Islands
- Waterfront rentals Cayman Islands
- Beach house rentals Cayman Islands
- Pet-friendly rentals Cayman Islands





