Vacation rentals with a pool in George Town

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Top-rated rentals with a pool in George Town

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Guest favorite

Condo in George Town

4.98 out of 5 average rating, 47 reviews

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.

Aug 25 – Sep 1

G$96,189 GYD per night

Guest favorite

Condo 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.

Jan 10 – 17

G$60,594 GYD per night

Guest favorite

Condo 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!

Feb 1 – 8

G$91,010 GYD per night

Superhost

Condo 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.

Oct 11 – 18

G$79,699 GYD per night

Guest favorite

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.

Apr 18 – 25

G$35,641 GYD per night

Superhost

Condo in George Town

4.95 out of 5 average rating, 61 reviews

Oceanfront 2bed 2bath Condo Seven Mile Beach

Seven Mile Beach property with direct ocean views newly refurbished throughout. Walking distance to Georgetown, supermarket, shops, gym, spa’s, and a variety of restaurants from fast food to fine dining. Spacious open plan condo with a private patio. The complex is small and family friendly with a pool, exclusive beach (with great snorkeling) & access to a tennis court. There is a comfy sofa, dining area, cable, ensuite master w/ ocean view, bedroom with a twin/king ensuite.

Aug 3 – 10

G$80,869 GYD per night

Guest favorite

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.

Jul 7 – 14

G$98,069 GYD per night

Guest favorite

Condo in George Town

4.88 out of 5 average rating, 130 reviews

Beautiful Modern Condo on 7 Mile Beach

Welcome to our beautiful second floor condo on the world renowned Seven Mile Beach. Sunset Cove is a beachfront resort minutes from George Town. It has a stunning beach lagoon and amazing pool with a kiddies pool, hot tub and swim-up bar. Our “beach chic” condo has just been fully renovated. We stripped it back to the bare concrete floor and walls and everything is brand new. We hope you like it and look forward to welcoming you to our little island paradise!

Oct 30 – Nov 6

G$83,845 GYD per night

Guest favorite

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.

Jun 12 – 19

G$33,794 GYD per night

Guest favorite

Apartment in George Town

4.96 out of 5 average rating, 117 reviews

Flip Flop Villa

A superb location to all things fun makes this condo a great spot! Centrally located to Spotts Beach or Smith Cove Beach its only 10 mins away or George Town to Seven Mile Beach 15 mins away. Ideally located to explore both coasts. Out of the way of the hustle & bustle but close to it if you like. Two grocery, convenient stores and restaurants within a few mins.

Aug 29 – Sep 5

G$52,974 GYD per night

Superhost

Condo 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.

Sep 2 – 9

G$25,705 GYD per night

Guest favorite

Condo 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.

Sep 15 – 22

G$78,578 GYD per night