Dream Caribbean Vacations: Cayman Islands Resorts And Rental Accommodations

When dreaming of an island getaway, you want something that checks all the boxes. There are many Cayman Islands Resorts that do just that!

Think of sunny warm weather with stunning sandy shores. Turquoise water so clear you can see your feet at the bottom and fish swimming by. Residents that welcome guests warmly no matter who you are or where you’re from. Delicious cuisine that surprises you in all the best ways. Easy to get to with many non-stop flight options. And lastly, accommodations for all types of travelers and budget points.

The Cayman Islands seemingly checks all those boxes. I was fortunate to tour a whole host of Cayman resorts and rental accommodations on my recent trip. Here’s a list of 17 hotels, resorts, condos, timeshares, and private villas to consider for your next couples, family, or group getaway.

But First, A Quick Cayman Islands Overview

The Cayman Islands are three land masses between Cancun, Mexico, and Jamaica. This British overseas territory received a Trip Advisor’s Traveler’s Choice Best of the Best 2023 award for its many above-and-beyond reviews from its community in the Caribbean.

Known for its idyllic beaches and stunning turquoise waters, it is a dreamy island escape for divers, honeymooners, families, groups, and foodies. Known as the Culinary Capital of The Caribbean, the islands have 200 restaurants and casual eateries across cuisines, as their small islands residents represent 142 nationalities.

Boston, Charlotte, Atlanta, Chicago, Denver, Houston, Dallas, Los Angeles, Miami, Minneapolis, Newark, New York, Philadelphia, Tampa, Fort Lauderdale, Washington, D.C., and Baltimore all have direct flights. Additionally, the Cayman Islands in the Caribbean have non-stop flights from Toronto and London.

Cayman Resorts and Rentals: Grand Cayman Island

The largest and most developed of the three islands have a broad range of hotels, resorts, timeshares, and rental properties. Whether you’re looking for an oceanfront luxe hotel or condo on Seven Mile Beach, a secluded private rental home, or an affordable stay, you can find an option for your getaway on Grand Cayman.

1. Kimpton Seafire Resort and Spa

The minute you walk into this hotel, you’ll see why it’s named the top resort on the island, even though it is the newest offering. Their open-air design lets guests enjoy the near-perfect year-round Caribbean weather and provides endless water vistas from its elevated 24-foot perch above Seven Mile Beach.

From the breathtaking entry and winding gardens filled with secret hideaway spots to their two seaside pools, it’s easy to see why couples and families are drawn to this property and its 264 guest rooms. Whether you book this property or not, don’t miss their epic Sunday Brunch or cocktails at Library by The Sea, offering original drinks inspired by literary works and libations made with decades-old vintage spirits.

2. The Ritz-Carlton Grand Cayman

This luxury resort on Seven Mile Beach is surprisingly family-friendly. With a whole host of beach activities and an on-site Starfish Cay water zone, kids will enjoy the waterslides and fountains while parents will appreciate the legendary ambiance and service The Ritz is known for. Golfers of all ages will marvel at the nine-hole Greg Norman-designed golf course built around The North Sound.

3. Palm Heights

Palm Heights offers the best of both worlds for hip travelers who want to be on world-renowned Seven Mile Beach but crave a smaller, almost all-inclusive environment. Created from an old estate, the first boutique hotel in Grand Cayman is a mix of understated high-design, cheeky, yet effortlessly cool.

How cool? Recently Bella Hadid, Emily Ratajkowsk, and Chloë Sevigny stayed. With a restaurant so good that guests don’t feel a need to leave and an evening environment that is fun and social yet unpretentious, you’ll never know this unassuming property is filled with a collection of the who’s whos visiting the island.

4. The Westin Grand Cayman Seven Mile Beach Resort & Spa

The floor-to-ceiling view of their beachfront property hits you the second you walk into the lobby. It’s instant vacation bliss. With 700 feet of beachfront acreage, guests can spread out along some of the most pristine white sand on Seven Mile Beach. No matter your room location, it’s a quick walk to the beach, water sports, or the largest freshwater pool in Grand Cayman.

The food offerings at Westin Grand Cayman are way beyond your typical hotel fare. Headed by classically French-trained Executive Chef Sandy Tuason, who previously worked with Four Seasons Resorts and at Daniel Boulud and David Burke’s New York City hot spots. That’s why their legendary local-loved Sunday brunch and a meal at Woto can’t be missed.

5. Grand Cayman Marriott Resort

If you love basking in the sun and taking in ocean views but prefer staying off the beach, consider Grand Cayman Marriott Resort. This oceanfront hotel has a stunning courtyard, hip lobby, open-concept multi-restaurant scene, and a beachfront pool. Every Friday, the lobby is filled with socializing guests enjoying the DJ, ramen and sushi cafe, bar, and other culinary offerings.

6. Hampton by Hilton Grand Cayman

Adding an affordable option to Seven Mile Beach, Hampton’s chic design and warm atmosphere take you by surprise. With a lively outdoor courtyard and tropical garden pool, the beach is only 43 steps down a short path. They offer guests standard hotel rooms, studios, and one or two bedrooms options. Most rooms include a kitchenette with a microwave and a mini fridge, and there are even shared laundry facilities for those who like to travel light.

They offer a complimentary daily hot breakfast and house a beloved lunch spot on the island with locals and visitors. Ms. Piper’s outdoor lounge and restaurant is like going to your friend’s backyard to enjoy her best tapas, salads, and drinks. With live music rivaling professional performers, it’s a must-stop for any Cayman Island visitor.

7. Caribbean Club

Caribbean Club offers 2700-foot three-bedroom condos only steps from the ocean for those who prefer more home-like vacation accommodations. With wraparound balconies and sumptuous furnishings, it’s a luxury beach home that meets an exclusive boutique hotel vibe.

Just like a hotel concierge, their staff can assist you in making your dream trip a reality. Want to stock your full gourmet kitchen with all of your family or group’s food before you’re arrival? No problem!

8. Coral Stone Club

Another Seven Mile Beach boutique complex, Coral Stone Club, offers 29 beachfront two or 3-bedroom condos, beautifully appointed, plus an oceanfront swimming pool. A favorite among new and returning guests, including Food Network Star Jeff Mauro, who has been coming to the Cayman Islands with his immediate and extended family for over 30 years.

If you’re strolling down Seven Mile Beach and see a group playing cornhole on the sand in front of the property listening to the Grateful Dead, it just might be The Sandwich King himself.

9. Black Urchin

If you’re looking for a large, luxurious, private villa but don’t want to be entirely on your own, then book one of the stunning design-forward yet family-friendly villas at Black Urchin. This 2.5-acre property with its private beach has a concierge on site and chef services to tailor your family or group’s dream vacation. Take your pick from one of their two homes or four-bedroom suites for vacation or a small intimate destination wedding.

10. Wyndham Reef Resort Grand Cayman

This East End timeshare property is far from the crowds providing a more serene tropical vacation. Pick from studios, one or two-bedroom units, all of which are oceanfront and steps from the beach and prime snorkeling. Whether you want to make your own meals in your fully stocked kitchen or sign up for their all-inclusive program, you can choose at Wyndham Reef.

11. Regal Beach Club

Affiliated with the timeshare exchange company Interval International, you’ll be at your slice of paradise on Seven Mile Beach within 15 minutes from the airport. A boutique property with 21 two and three-bedroom luxe condos, it has fantastic beach acreage with the powdery white sand of your dreams.

Cayman Resorts and Accommodations on Cayman Brac

If you’re looking for a laid-back, relaxed getaway, consider the 10-square-mile island of Cayman Brac. You can fly directly from Miami International Airport or take a quick 30-minute flight from Grand Cayman.

12. Cayman Brac Beach Resort

Rebuilt after the devastating Hurricane Paloma, all 40 guest rooms, oversized free-form pool, and two-story bar are back open. Steps away from Reef Divers’ launching point, this stunning, small, and casual beachfront resort will appeal even to those non-divers in your family or group.

13. Coral Beach Escape

The passion project of one Canadian family who purchased 2.5 acres of waterfront land in 2008 is now a wholly private and secluded pair of beachfront homes. Located in Bamboo Bay, this one-bedroom cottage and three-bedroom home are available for rent. A rarity, the property is wheelchair accessible and was built according to ADA standards.

That means that all travelers can visit and enjoy the 2,000 square foot oceanfront deck space and, at night, marvel at the stars in the evening sky far away from other resorts and visitors.

Cayman Resorts and Rentals: Little Cayman

The smallest of The Cayman Islands, Little Cayman, is only ten miles long and one mile wide. But don’t let its size turn you off. It’s a tranquil favorite of couples, honeymooners, and travelers looking to escape it all. If you’ve dreamed of traveling to a private island, Little Cayman is for you. Accessibly only via air, it’s a 30-minute flight from Grand Cayman International Airport.

14. Southern Cross Club

The island’s original resort opened 65 years ago and lures guests back repeatedly. But what hasn’t changed is the 1:1 staff-guest ratio or the serene, private, personalized environment. Stay in one of their 14 colorful beach bungalows and enjoy first-class diving and fishing, delicious dining, and what they describe as their own brand of barefoot luxury.

15. Paradise Villas

If you usually book Airbnb for vacation peace and quiet, look at Paradise Villas. Their 12 traditional wooden cottages all face the ocean a few feet from the water’s edge, and they offer warm, welcoming hospitality from the resort staff.

Their spot allows for that peaceful crowd-free getaway, but its central location means you’re not too far from the shops, grocery store, nature reserve, or museum. Take one of their complementary bikes and explore the island at your own pace.

16. Little Cayman Beach Resort

A resort for divers built by divers, it’s an intimate environment that provides personalized guest services both above and below the water. A relaxed and causal family-owned property with 40 rooms, enjoy on-site dining after a day spent in Cayman’s turquoise waters and world-renowned reefs.

17. Le Soleil d’Or

Discover Le Soleil d’Or if you’ve thought of going off the grid but enjoy life’s luxuries. This secluded beachside farm-to-table retreat’s food is grown on a sprawling on-site 20-acre farm. Located on a blufftop, it’s the slow-paced escape for hectic lives.

Choose from The Coast House, The Manor House, or the three-bedroom farmhouse. Or, for a private island experience, book The Beach Studio, two miles away from the main resort grounds. This article originally appeared on Savoteur.

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