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.

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Guest favourite

Home in Stake Bay

5.0 out of 5 average rating, 35 reviews

Modern Oceanfront, 2Primary Suites, sleeps 6, pool

We offer a Hurricane Worry-free Guarantee. Only a short 25-minute flight from Grand Cayman, this newer home provides stunning oceanfront vistas with all modern amenities to enjoy barefoot luxury. Large windows and the open concept floor plan allow for breathtaking views of the pool and sea and include a fully-equipped kitchen, dining, and living areas. Also overlooking the ocean are two master king-size bed suites with tiled baths. A third bedroom has a queen bed and views of tropical foliage.

15–22 Aug

$640 SGD per night

Guest favourite

Apartment in George Town

4.93 out of 5 average rating, 152 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!

1–8 Feb

$607 SGD per night

Guest favourite

Apartment in Grand Harbour

4.92 out of 5 average rating, 197 reviews

The Sanctuary serene Grand Harbour view 2Bed/2Bath

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.

10–17 Jan

$396 SGD per night

Guest favourite

Home in West End

5.0 out of 5 average rating, 12 reviews

POOL, sandy beach w/cabana, wi-fi, a/c, sunsets

Truly Amazing Tropical Beach Paradise on the Water w/Pool. Prop has private entrances, full kitchen (with everything), dining, living, full bathroom, beach cabana, hammocks, bikes available, grill, kayaks, fire pit. WiFi. Great snorkeling right out front. Great sunsets! One of the few rental places on the island with a sandy beach. Leeward side of the island so many days with calm waters. Local cell phone provided. Washer and Dryer, TV, Linens, beach and bath towels & more. 1 of only 3 units.

26 Oct – 2 Nov

$207 SGD per night

Superhost

Apartment in George Town

4.85 out of 5 average rating, 120 reviews

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.

11–18 Oct

$531 SGD per night

Guest favourite

Guest suite in Savannah

4.97 out of 5 average rating, 196 reviews

Paradise Escape-Charming Oceanfront Guest Suite

A tranquil oceanfront escape for couples and solo adventurers... Ours is a unique community with quaint freehold condo cottages on a vast tract of oceanfront land. 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.

18–25 Apr

$238 SGD per night

Guest favourite

Apartment in Rum Point

4.92 out of 5 average rating, 113 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!

3–10 Dec

$795 SGD per night

Guest favourite

Cottage in West Bay

5.0 out of 5 average rating, 173 reviews

Luxury Cottage, 1bd/1ba steps to Pool+7 Mile Beach

Our Queen Cottages are part of the Botanica collection of charming island style cottages which won the coveted 2021 Governor's Award for Excellence in Design and Construction. Our focus is casual luxury with dreamy details and high end amenities. Amenity highlight includes a resort style pool with a heated spa set in a tropical oasis with ample space to hang out and enjoy some down time. Be sure to check out our other listings under my profile. Non Smoking Complex.

7–14 Jul

$640 SGD per night

Guest favourite

Home in Patricks Island

5.0 out of 5 average rating, 10 reviews

Seabreezes-Your Oceanside Escape

Kick back and relax in this calm, stylish loft situated in an oceanfront community- a perfect Caribbean get away for a short break or longer holiday. The central location allows for easy access by car to all the areas of this lovely holiday Island. The property offers open spaces, 5 pools, an oceanfront walkway and a Cabana. Step outside to enjoy a morning swim in the pool; a glass of wine on the porch, or a romantic evening stroll by the boardwalk.

12–19 Jun

$226 SGD per night

Guest favourite

Home in Little Cayman

4.97 out of 5 average rating, 144 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!

2–9 Sep

$285 SGD per night

Superhost

Apartment in George Town

4.84 out of 5 average rating, 102 reviews

Cozy Condo near Seven Mile Beach!

The Cozy condo is a great choice for guests who come to Grand Cayman for work, play or both! Its location is minutes away from George Town, Camana Bay and Seven Mile Beach. There is are 2 supermarkets/pharmacy easily accessible by foot or a short drive. Camana Bay is about a 3 minute drive away and has entertainment, shopping, drinking and dining.

2–9 Sep

$172 SGD per night

Guest favourite

Apartment in George Town

4.95 out of 5 average rating, 107 reviews

2 BR beach condo resort with pool and ocean views

This luxury penthouse condo has everything for your perfect vacation. Enjoy stunning views of the sun setting over the Caribbean Sea from your private balcony. Located in a resort style complex with a great amenities. This includes bike use, large pool with swim up bar, kiddie pool and hot tub. Great snorkeling off our beach.

15–22 Sep

$523 SGD per night