
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 Beachview Retreat, Cayman Island.
Luxurious, four bedroom, four and a half bath home with ensuite bathrooms and a half bath for guest. All bedrooms provide a private balcony with stunning oceanviews. This modern gated home in Northside is only 40mins from the airport and features a private pool, public beach access and a mini-golf course. BEDS Master on upper level has a king bed Second bedroom on upper level has a queen bed Third bedroom on upper level has 1 full bed and 3 twins Fourth bedroom on lower level has a queen bed.

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.

Casa Avi - Your Calm Coastal Gem
Discover Casa-Avi an idyllic beach front oasis nestled in sea-grape trees and secluded on the edge of Bodden Town. Immerse yourself in elegant king size bedrooms, breathtaking ocean views, and art-infused living spaces curated by renowned artist Avril Ward. Savor panoramic ocean views from retractable sliding doors, enjoy direct beach access for kayaking and snorkeling adventures. Downstairs, simply unwind in the embrace of hammocks while you BBQ and refresh in the private saltwater pool.

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.

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,

Beachside Retreat - Walk to 7 Mile Beach
New Listing! Enjoy our brand-new unit at special introductory rates for a limited time. Modern renovated ground-floor 1BR/1BA — Seven Mile Beach Corridor Enjoy luxury living walking distance from Seven Mile Beach, top dining, shopping, and nightlife. Relax in the large, screened patio overlooking lush, landscaped grounds. Amenities include: - Swimming pool - 2 x beach chairs with coolers - 1 x beach umbrella - 2x beach towels - 2 x bath towels - Starter Shampoo and conditioner

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!

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.

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

Featherstone - Upstairs Beach Front Apartment

Gorgeous 3 Bed Brand New by 7 Mile Beach

BeachPlumVilla

3 Bedroom Beach House with Pools

Island Oasis

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

Modern Oceanfront, 2Primary Suites, sleeps 6, pool

Sweetie Kai by Grand Cayman Villas
Condo rentals with a pool

Seven Mile Beach Newly Renovated Modern Condo

Cayman Wind and Sea

Seven Mile Beach with Soul

Ocean View Studio, Queen Bed, Patio, Kitchenette

Beautiful Beachfront 2BR Condo.

Relax in Style in Paradise

Sunset Hideaway (3)

Serenity by SunsetCove 2b/r 2 b/r
Other holiday rentals with a pool

Seaside Serenity at Allure

Tua'r Mor (near the sea) quiet waterfront escape.

Beachfront on Spotts Beach!

Elegant One-Bedroom Apartment in Grand Harbour

OCEAN VIEW at SUNRISE SOLILOQUY - Paradise Villas

Seaing Spotts: Beachfront Seaside retreat! Cayman

Ocean front 2 bedroom condo

Incredible Beach Front Condo At Kaibo Yacht Club
Destinations to explore
- House rentals Cayman Islands
- Villa rentals Cayman Islands
- Luxury rentals Cayman Islands
- Fitness-friendly rentals Cayman Islands
- Townhouse rentals Cayman Islands
- Beachfront rentals Cayman Islands
- Rentals with a fire pit 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 kayak Cayman Islands
- Guesthouse rentals Cayman Islands
- Hotel rooms Cayman Islands
- Rentals with a patio Cayman Islands
- Apartment rentals Cayman Islands
- Rentals with a hot tub Cayman Islands
- Condo rentals Cayman Islands
- Family-friendly rentals Cayman Islands
- Rentals with an EV charger Cayman Islands
- Cottage rentals Cayman Islands
- Waterfront rentals Cayman Islands
- Pet-friendly rentals Cayman Islands
- Beach condo rentals Cayman Islands
- Smoking-friendly rentals Cayman Islands
- Beach house rentals Cayman Islands
- Rentals with beach access Cayman Islands




