Vacation rentals with a pool in Grand Cayman

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Top-rated rentals with a pool in Grand Cayman

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

5.0 out of 5 average rating, 49 reviews

Beautiful apartment in Seven Mile Beach

The apartment has been recently renovated and has new, modern furniture. The kitchen is very complete with all the necessary utensils to prepare meals. It is on the second floor and overlooks the pool. The Sunset Cove condominium has 3 swimming pools, the main one, the children's pool and also a hot tub. The condominium has its own private beach, it is surrounded by rocks looking like a natural pool, ideal for relaxing, snorkeling and also for children. Near the restaurants and bars in SMB.

Apr 27 – May 4

R9,518 ZAR per night

Guest favorite

Condo in George Town

4.94 out of 5 average rating, 154 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!

Sep 29 – Oct 6

R6,078 ZAR per night

Guest favorite

Guesthouse in Cayman Islands

5.0 out of 5 average rating, 34 reviews

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

This lovely one-bedroom, one-bath charismatic bungalow is located in the quiet neighbourhood of Sunrise Landing, Newlands, and is perfect for couples or small families. Tua’r Mor provides everything you need to feel at home, with an open kitchenette and dining/living area. The unit has everything from beach towels, beach chairs, and coolers so you can enjoy a day out. A hammock awaits you in your own private garden, overlooking the canal, where you can enjoy watching the sun rise or set.

Oct 4 – 11

R2,409 ZAR per night

Superhost

Condo in George Town

4.85 out of 5 average rating, 121 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.

Dec 17 – 24

R11,679 ZAR 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 3 – 10

R3,168 ZAR per night

Guest favorite

Condo in Rum Point

4.92 out of 5 average rating, 115 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!

Nov 9 – 16

R8,591 ZAR per night

Guest favorite

Apartment in East End

4.91 out of 5 average rating, 11 reviews

Spacious Oceanfront Studio

Take a break and unwind at this peaceful studio overlooking the sea from your private patio. The studio boasts unparalleled views with a bathroom, king size bed and a kitchenette. Set within the Reef Resort, enjoy lazing the day on the beach, snorkelling or diving. The property boasts a lively bar, restaurant with daily menus, coffee shop, spa, and fitness centre. You also have a small market and adult beverage store just across the street! Come join us in Cayman!!!

Oct 14 – 21

R3,266 ZAR per night

Guest favorite

Cottage in West Bay

5.0 out of 5 average rating, 177 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.

Apr 9 – 16

R11,498 ZAR 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.

Jul 12 – 19

R3,003 ZAR 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 5 – 12

R4,708 ZAR per night

Superhost

Condo in George Town

4.84 out of 5 average rating, 103 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.

Oct 13 – 20

R2,309 ZAR per night

Guest favorite

Condo in George Town

4.95 out of 5 average rating, 108 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.

Aug 29 – Sep 5

R6,848 ZAR per night