The Best Vacation Rentals to Book in the Cayman Islands

Bag yourself a rental near Harbour Drive in George Town for easy access to waterside dining
Bag yourself a rental near Harbour Drive in George Town for easy access to waterside dining | © robertharding / Alamy Stock Photo
Photo of Gabi Ancarola
29 December 2021

Just south of Cuba, the Cayman Islands are an idyllic trio headed by Grand Cayman, an island blessed with blissful Caribbean beaches and unmissable sights, including Pedro St James Castle and Stingray City. Visit the sister islands, Little Cayman and Cayman Brac, for diverse wildlife, deserted beaches, lush forests and accessible shipwrecks beneath the ocean. If you’re looking for vacation rentals in the Cayman Islands, check out our selection of the best, all bookable on Culture Trip.

Casa Caribe Condominiums Unit 21, for contemporary condos on Seven Mile Beach

5/5 (4 Reviews)
The octagonal outdoor swimming pool at Casa Caribe Condominiums on Seven Mile Beach.
Courtesy of Casa Caribe Condominiums Unit 21 /
Unavailable for the next 3 months
Direct access to the resort-lined, sugar-sand Seven Mile Beach is your reward for checking into unit 21 at Casa Caribe. The three-bed condo comes with a screened patio overlooking the sea; sit and drink your morning brew cooled by the breeze and the sound of the waves. Cook up a storm in the kitchen and spend your days in the dive-in swimming pool, bubbling hot tub, gym and tennis court. Being on the west coast of Grand Cayman means you’re just over 4km (3mi) from Stingray City, a group of sandbanks where you can snorkel among southern stingrays.
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Sprat Bay Luxury Villa, for fancy, family-friendly fun in George Town

The palm-fringed, beachfront plunge pools at Sprat Bay Luxury Villa in George Town.
Courtesy of Sprat Bay Luxury Villa / Expedia
Price Drop
Now from $2426 per night

On the coast of George Town, overlooking Crawl Bay, this large, lavish villa will stop you in your tracks with turquoise pools and loungers perfectly matching the ocean backdrop. Lofty palm trees lining a private sandy shore enhance the impact. Admire the view from your bed with a sundowner in hand. Adding to the serene vibe, interiors are cool and cream-coloured, from the floor tiles to the leather sofas. Your children will love the kids’ play area – a handy resource in a vacation home sleeping up to 22.

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Ocean Paradise, for beachfront bliss at Rum Point

4.8/5 (32 Reviews)
Ocean Paradise
Courtesy of Ocean Paradise / Expedia
Price Drop
Now from $458 per night
On the tranquil northern coast of Grand Cayman, Ocean Paradise is a complex of five three-bedroom villas in tropical grounds. The villas are named for their colours; Cream is furthest from the beach but makes up for it with knockout views, while Green and Yellow are right by the sand. Choose to spend your vacay swinging in a hammock, soaking up the ocean views from your balcony or sofa, or snorkelling in the warm sea. Rum Point is steps away, home to a quiet beach where you can sink into your lounger with a creamy, chilled piña colada and a juicy burger from the lively Wreck Bar.
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The Grandview Condos on Seven Mile Beach, for laid-back living

4.8/5 (84 Reviews)
An oceanfront pool surrounded by lounge chairs and tables at the Grandview Condos on Seven Mile Beach.
Courtesy of The Grandview Condos on Seven Mile Beach / Expedia
Unavailable for the next 3 months

At the quieter, southern end of Seven Mile Beach, an eight-minute drive from George Town, these pastel blue condos aren’t just pretty. Stay here to play basketball and tennis before cooling off in the ocean-view swimming pool. Come nightfall, just chill in the hot tub. With a reef just offshore, there’s no excuse for not snorkelling. Inside your condo, you’ll find a bright space with a screened porch, where you can relax knowing your favourite groceries will be delivered to your door – so fire up the grill and dine under the stars.

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Buttonwood Apartment, for a home from home in Prospect Park

Buttonwood Apartment
Courtesy of Buttonwood Apartment /
Unavailable for the next 3 months
In Prospect Park, just under 2mi (3km) from Spotts Public Beach, this cosy Grand Cayman vacation rental will make you feel at home. Get the barbecue going and dine beneath the parasol on the decked patio, surrounded by palm-fringed lawns. The three bedrooms are painted in warm peachy tones, with tropical-pattern throws and white floor tiles. If you fancy exploring the island by car or bike, you can rent both onsite. It’s under a 10-minute drive to Pedro St James Castle, Grand Harbour and George Town.
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  • Aqua Bay Club Condos, for splendid isolation on Seven Mile Beach

    4.8/5 (68 Reviews)
    The palm tree-lined pool in front of Aqua Bay Club Condos on Seven Mile Beach.
    Courtesy of Aqua Bay Club Condos / Expedia
    Unavailable for the next 3 months

    Wake up each day and step onto your private terrace overlooking one of the best beaches in the Caribbean. Set on attractive grounds studded with banana and palm trees, this dusty-pink property offers one- and two-bedroom condos spread across three levels on a quiet, northern section of Seven Mile Beach. If the coastal interiors – featuring beachy artwork and wicker furniture – get you in the mood for snorkelling and diving, the access point to Cemetery Reef is less than 10 minutes’ walk away.

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    Coral Stone Club, for casual, Caribbean-style apartments on Seven Mile Beach

    4.8/5 (27 Reviews)
    The oceanfront Coral Stone Club condos on Seven Mile Beach.
    Courtesy of Coral Stone Club / Expedia
    Unavailable for the next 3 months

    Set on the popular Seven Mile Beach, these three-bedroom condos each have balconies or terraces with beautiful ocean views. Each also has individual style, meaning some feature fancy gold tones and four-poster beds, while others come with relaxed wicker furnishings and tropical-patterned fabrics. No matter what your interior taste, you’ll love relaxing in the well-manicured grounds woven with pathways leading to the freeform pool and beach. Stock up at the grocery store, a six-minute walk away, or grab a table at one of the many restaurants within walking distance.

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    Regal Beach Club, for refined condo comfort on Seven Mile Beach

    4.8/5 (152 Reviews)
    A balcony overlooking the sunshine-yellow Regal Beach Club and Seven Mile Beach.
    Courtesy of Regal Beach Club / Expedia
    Price Drop
    Now from $546 per night
    Another top spot on Seven Mile Beach, this sunshine-yellow complex features sleek, three-bedroom, three-bathroom condos. You’ll be fighting over the master suite, which features private terraces overlooking the Caribbean Sea. When you want to dip and dive, there are two pools: an oval, oceanfront option and a circular alternative set back in the leafy grounds. If a cooling breeze rolls through, thrash your partner at tennis before retiring to the hot tub, with a sundowner in hand.
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    Caribbean Club Luxury Condo Hotel, for ocean-view opulence on Seven Mile Beach

    4.9/5 (36 Reviews)
    An aerial view of the rectangular swimming pool at Caribbean Club Luxury Condo Hotel on Seven Mile Beach.
    Courtesy of Caribbean Club Luxury Condo Hotel / Expedia
    Price Drop
    Now from $1147 per night
    On Seven Mile Beach, under 3km (2mi) from North Sound Golf Club, these spacious suites and villas combine island glamour with luxurious home comforts – we’re talking jetted baths, memory-foam beds and Egyptian cotton sheets. There’s no need to head to the grocery store as you’ll arrive to a well-stocked kitchen. If you’re feeling too lazy to cook, head downstairs to Luca, one of the most popular Italian restaurants on the island. Spend your days swimming in the huge, ocean-facing pool, then curl up in a beach cabana with a cold cocktail.
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