The Cayman Islands may be best known for its tax benefits, but ask a travel buff what’s so special about this British Overseas Territory and they will wax eloquent about the beautiful, white sand beaches, the magnificent diving spots, and the warming hospitality of the people there.
However, the Cayman Islands are spread over 264 square kilometers and each island is quite different from the next. There are also some areas that are more touristy than others.
If you’re looking for diving spots, The North Sound’s reef is a protected lagoon that is a must-see, or for beach buffs, the famous Seven Mile Beach is one of the best in the Caribbean. For nature lovers, you will love the diverse wildlife on Little Cayman.
Wherever you go in the country, there is no doubt that the Cayman Islands is a beautiful holiday destination, especially if you are a keen diver.
When it comes to choosing a place to stay, I always recommend choosing a vacation rental. Not only do they offer an authentic experience and all the homely comforts that a hotel just can’t compete with, but they are ideally located. And in the Cayman Islands, there are tons of amazing beachfront vacation rentals for an affordable price. It’s a no-brainer, really.
In this guide, I have selected my top 20 perfect vacation rentals in the Cayman Islands for you to choose from. I have taken into account the different travel styles, group sizes, and budgets so you will be sure to find one that is right for you.
So, without further ado, let’s take a look…
Quick Answer: These are the Top 5 Vacation Rentals in the Cayman Islands
2BR Beach Home
- > $$
- > 4 Guests
- > Relaxed beachside home
- > Located in North Side
Cute 1BR Home
- > $
- > 3 Guests
- > Jacuzzi and luxury amenities
- > Located in Grand Harbor, George Town
2BR Villa W/ Private Beach
- > $
- > 4 Guests
- > Beautiful garden and deck
- > Located in Banksville
2BR Seaside Home
- > $$
- > 7 Guests
- > Beautiful views of the Caribbean Sea
- > Located in Cayman Brac
6BR Beachfront Mansion
- > $$$$
- > 14 Guests
- > Incredible luxury villa
- > Located in Rum Point, North Side
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Types of Accommodation in the Cayman Islands
The Cayman Islands is definitely a tourist and expat-driven country, with many hotels, resorts, and private villas for travelers to choose from. Depending on your preferences and budget, there may be numerous places you could book.
But before you start looking for where to stay in the Cayman Islands, let’s quickly break down the most common types of accommodation that you will find across the islands so you can see which one would be best suited for you.
Apartments and Condos
Due to the existence of an international airport on Grand Cayman, there is a higher frequency of apartments and condos available to rent in and around George Town.
Most of these apartments offer amenities like full kitchens, laundry rooms, and views for days, most likely a beautiful view of the sea. In fact, it is almost a given that vacation rentals in the Cayman Islands will have a beautiful view.
Most of these apartments and condos will also have access to shared pools and fitness centers, and maybe even private parking.
If you’re a solo traveler or you’re looking for cheaper accommodation, apartments will be your best bet.
Houses and Villas
If beach holidays are your thing, the Cayman Islands will be the highlight of your life. There is possibly a gazillion independent houses and villas that are available for you to book, irrespective of your group size or budget. Okay, perhaps a “gazillion” might be an overstatement, but you get a general idea.
Beach homes and villas tend to be the more luxurious style of accommodation and can range in size and budget, but typically they have more than 2 bedrooms and are better suited to families and groups.
Some of the more swanky villas and homes will also have their own stretch of private beach space, too. Private infinity pools looking out to the sea are very common to see from some villas.
Timeshares in Resorts
The Cayman Islands’ economy is predominantly driven by international tourists and ex-pats. Many of these visitors from overseas countries like to maintain a semi-permanent base of sorts on the Cayman Islands. Hence, they often buy private suites within resorts and hotels. When not in use, they rent these out as vacation rentals in the Cayman Islands.
Timeshares can be quite reasonably priced, as they are second homes for ex-pats, so not really an investment for tourism. If you’re looking to travel to one of the best Caribbean islands and not burn a hole in your wallet, this might help you out.
Of course, because I prefer holiday rentals that are a far cry from most cookie-cutter hotel rooms and suites, I try not to include such timeshares in any lists I create, unless they are so amazing that they could be considered a gift to humankind! Again, you probably get my drift…
Looking for other types of accommodation? Check out our guide to Where to Stay in Cayman Islands!
The Top 20 Vacation Rentals in the Cayman Islands
There are myriad reasons why the Cayman Islands make for a fantastic holiday destination, but you already know that. But vacation rentals do really make a holiday complete, if you get a good one.
So now it’s time for me to make your life easier by showing you not one or two, but twenty amazing holiday rentals in the Cayman Islands… Let’s begin, shall we?
Best Overall Vacation Rental | 2BR Beach Home
- $$
- Relaxed beachside home
- 4 Guests
- Located in North Side
This 2 bedroom, 2 bathroom home might be located on a property that is shared with four other villas, but they have been all constructed in a way that offers the guests in each villa adequate privacy.
There is a shared pool with a shaded outdoor area. The beach is only a few steps away.
The villa has a full setup kitchen and separate bathrooms for each bedroom, meaning that you don’t have to share your space. There is a separate bar area and a spacious living area. Towels and linen can be changed daily on request.
Budget Vacation Rental in The Cayman Islands | Cute 1BR Home
- $
- Jacuzzi and luxury amenities
- 3 Guests
- Located in Grand Harbor, George Town
This is a small family-owned vacation rental in The Cayman Islands, nestled at the edge of the North Sound, in Tropical Gardens. It is within minutes of the airport, the world-famous beaches, and local attractions.
This one-bedroom property can sleep up to three guests and has an amazing view of the sunset, perfect for a romantic getaway for two. Plus there is direct access to the lake in case the beaches get too much (as if they would!).
The property has a modern style throughout and all the state-of-the-art appliances. There’s also a Jacuzzi, a private entrance, kitchenette, en-suite bathroom with walk-in shower, and best of all – a super affordable price tag.
Best Vacation Rental for a Families | 2BR Seaside Home
- $$
- Beautiful views of the Caribbean Sea
- 7 Guests
- Located in Cayman Brac
This vacation rental in The Cayman Islands is perfect for a lazy seaside holiday, where you laze, read, eat, and swim every day. Located only a few steps away from the sea, you will be treated to fantastic water views from almost every corner of the house.
There are many superb diving sites around the house, and this would be a great opportunity to introduce younger members of the family to the wonders of the world underwater. There are several stores nearby that offer diving equipment for rent.
Best Vacation Rental for Budget Couples | 2BR Villa W/ Private Beach
- $
- Beautiful garden and deck
- 4 Guests
- Located in Banksville
Travelling on a budget does not always have to result in staying in mediocre properties. Take for example this vacation rental in the Cayman Islands, appropriately named “Lovely Sea Dreams Villa”.
Boasting perks like a private beach, this 2 bedroom villa is the perfect place to return home to after a long day of lounging on the beach and soaking in some vitamin D.
At night, rest on the covered sea-facing patio with a glass of wine or a cocktail and marvel at the stars overhead. After all, there is so much joy to be found in doing nothing on one of the best tropical islands, too.
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View on Osprey View on REITop Value for Money Holiday Rental in The Cayman Islands | 3BR Bungalow
- $
- Affordable luxury villa with endless sea views
- 6 Guests
- Located in Cayman Brac
This villa is super affordable and its location cannot be beaten. While Cayman Brac is considered to be one of the world’s ultimate outdoor paradises, what with all the activities that one can do here, no one will blame you for simply wanting to stay ‘home’ and laze by the pool all day!
The house offers amazing views and is also set up with the most modern conveniences, including smart TVs in all three bedrooms as well as the living room. There’s also an Xbox to keep the kids entertained.
For the adults, the Jacuzzi, outdoor gas grill, and the hammock among the palm trees should be a welcome escape from normal everyday life.
Most Accessible Holiday Rental | 3BR Luxury Condo W/ Views
- $$$
- Single level ground floor condo
- 8 Guests
- Located on Seven Mile Beach
This is a modern apartment on the ground floor in a shared building. Tastefully decorated with high-end décor and elegant furnishings, this condo would also be suitable for guests using wheelchairs, as there are no stairs in the house and the rooms are easily navigable.
If you are in the mood to dine out or catch a quick drink, there are several resorts nearby, the most noteworthy of them being the Marriott. Most reviews of this vacation rental in the Cayman Islands have mentioned how incredibly welcoming the owner is, making this rental rate highly on the hospitality meter.
Best Modern Condo in The Cayman Islands | 3BR Luxe Condo
- $$$
- Oversized patio
- 6 Guests
- Located on Seven Mile Beach
Seven Mile Beach is often considered to be the hub of all activity in the Cayman Islands. As such, there are numerous resorts, hotels, eateries, bars, and entertainment venues in this area. Thus, this modern condo is best suited to travellers who love to be in the midst of all the hubbub and activity.
The condo itself has been decorated with contemporary furnishings and state-of-the-art appliances. The aesthetics of the condo are modern with a great balance of colour and modern design. The cherry on the cake though would have to be the oversized terrace/patio with its striking views of the open sea.
OTT Beachfront Holiday Rental | 6BR Beachfront Mansion
- $$$$
- Incredible luxury villa
- 14 Guests
- Located in Rum Point, North Side
Nothing I say about this mansion will ever do it justice. Nor will the pictures be able to adequately convey the beauty of this vacation rental in the Cayman Islands. Of course, the interiors are designer… Of course, it has an infinity pool and a spa pool… Of course, it is facing the sea and has incredible views on offer.
I mean, these are all pretty expected anyway, right?
However, nothing prepares you for the beauty of this Bali-esque vacation rental. The vaulted, high ceilings, the sleek marble floors, the huge gourmet kitchen all welcome you to stay indoors.
Outdoors, the koi ponds, thatched beach cabana, and the hammocks will call to you. I could go on and on about this rental for a few more hours, but I should probably stop now and let you check out the rest of the pictures of this house!
Best Vacation Rental for Parents with Babies | 2BR Home W/ Cot
- $$
- On its own private beach
- 6 Guests
- Located in West Bay, Cayman Islands
Looking for a place that goes beyond the usual? This just might be the rental you’ve been manifesting!
This beautiful 2 bedroom home is located directly on its own private beach and is within a short drive to the famous 7-mile beach. You can open the sliding doors of the living space and marvel at the beautiful shades of blue in the sea in front of you from your own private balcony.
This rental also allows guests access to a shared pool and there is also free parking. If you’re traveling with babies, there is a cot, baby bath, high chair, and all the equipment you might need.
Best Vacation Rental for a Large Group | 7BR Luxury Villa
- $$$$
- Grand, massive villa
- 16 Guests
- Located in West Bay
This vacation rental in the Cayman Islands is definitely pricier than most but is also meant for a larger group – so splitting the cost between mates can make it much more affordable.
If you are celebrating an important milestone with a group of friends or family or marking a significant achievement in your life, I guess it makes sense to splurge out on this vacation rental.
This villa has 7 bedrooms and 7 bathrooms, not that you could expect anything less with the steep nightly rate being charged. The house is beautifully designed and has a gorgeous outdoor area, complete with a pool and garden. The popular West Bay Beach is also about 2.7 kilometres away.
Best Vacation Rental for a Budget Family | 3BR Home W/ Pool
- $
- Located in a secure gated community
- 8 Guests
- Located in George Town
When you’re travelling as a family on a budget, it becomes important to save money where you can so that you can spend it on more important things like sightseeing or on local attractions. This vacation rental in the Cayman Islands promises a lot of bang for very little buck!
When it comes to holiday homes for a family, space becomes really important, and this rental scores high on that factor. It’s located directly on 7-Mile beach, so you are within walking distance of the top attraction in the Cayman Islands. Tours to Stingray City and other water sport activities can be found within walking distance, too.
There’s also a shared swimming pool directly outside the property which you can see from your own private balcony. Being a part of a resort community, guests also have access to shared tennis court too.
Best Location for a Vacation Rental | 1BR Cottage on the Beach
- $
- Cute Beachfront Cottage
- 2 Guests
- Located in George Town, Grand Cayman
This vacation rental in the Cayman Islands is located just meters from George Town harbor and is just 30 meters from the ocean. This one-bedroom property has a queen-size bed, a kitchenette, and BBQ outside.
This beachfront cottage is the perfect rental for a couple or solo traveler looking to stay in an affordable property directly on the beach. The highlight of this house is the outdoor deck, which has two loungers facing amazing views of the blue sea.
Luxury Vacation Rental in The Cayman Islands | 4BR Oceanfront Villa
- $$$
- Amazing extras for guests
- 8 Guests
- Located in Rum Point
This holiday home in the Cayman Islands sits on an elevated ridge and offers uninterrupted views of the ocean. The house itself is huge with more than enough space for everyone.
What is great about this vacation rental is that it comes with several value-add amenities such as a beautiful private infinity pool, a jacuzzi, a beautiful deck to soak up the sun from, and additional benefits.
The rental charges a 10% Guest Services Fee which includes the following benefits: use of the Fitness Center, use of snorkelling equipment, discounts on kayak rentals. Pre-stocking of groceries and arranging chefs, cooks, babysitting, and family photography can also be done at an additional cost.
Affordable Luxury Vacation Rental | 4BR Luxe Home on the Beach
- $$$
- Stunning water views from the villa
- 8 Guests
- Located in Rum Point, Grand Cayman
Located directly on the beach, this very private villa is great if you want a relaxed holiday where you don’t do much. White sands and crystal clear waters will welcome you a mere few steps from your front door.
Being a part of the Air BnB Luxe collection, you know you will get your money’s worth in this vacation rental in the Cayman Islands. If prior permission is taken, this villa would be stunning as the venue for a very intimate beach wedding.
Inside the villa, the bedrooms are luxurious and well-appointed with fine linen. There are hammocks for you to while away the day in, as well as other luxuries like a surround sound system, modern appliances, and plush furniture, among others.
Holiday Rental in The Cayman Islands with a View | 1BR Beach Home
- $$
- Unbeatable views of the beach and ocean
- 2 Guests
- Located on Rum Cove, Bioluminescent Bay
There are few countries in this world that offer such postcard views as the Cayman Islands. In fact, no matter where you go, you can be guaranteed beautiful pictures that will be a hit on the gram!
This rental is the cherry on the cake! This cute little cottage is located on Bioluminescent Bay which lights up at night by the fluorescent algae. It’s also within walking distance of top-rated restaurant Rum Point bar and Restaurant.
The beach in front of the villa is extremely private and you only have two neighbors, each with one-bedroom cottages too. There is also a workspace for any digital nomads wanting somewhere to hunker down for a while.
Best Cottage Style Vacation Rental | Cosy Cottage for a Couple
- $$$
- Beautiful luxury cottage
- 2 Guests
- Located in Rum Point
This charming cottage is located directly across the street from Rum Point, and is perfect for a couple looking for some peace and quiet.
Of course, being a part of Grand Cayman, you will never be too far away from some amazing eateries, bars, and shopping!
The cottage itself is cozy but fitted with everything you may need for a comfortable and luxurious stay. It is also within a few steps to the beach and there is an outdoor shower in the backyard, so you can snorkel on the nearby reef and rinse off in your very own tropical oasis. This duplex also has a full kitchen and laundry facilities.
Best Luxurious Vacation Rental | 3BR Villa on Rum Point
- $$$$
- Guests must be ages 10 and over
- 8 Guests
- Located in Grand Cayman
This is a great vacation rental in The Cayman Islands if you want to go all out on a luxurious holiday with friends or family. The rental is luxurious without being unaffordable and over the top.
The outdoor area of the villa includes a delightful salt water pool that looks out to the beach and ocean. There’s also comfortable outdoor seating that includes an alfresco dining area, loungers to soak up some sun, and more chairs and sofas.
There’s also a fire pit for the evenings. If you are an avid angler, the long dock attracts plenty of tropical fish. The villa also includes kayaks for guests to use and several other benefits.
Unique Vacation Rental in The Cayman Islands | 3BR Bubble Home
- $
- 4000 square feet home
- 10 Guests
- Located close to the Eastern end of Cayman Brac
This house is definitely an eye catching structure, with its cute dome shaped structure. It is way more spacious than you can imagine, with almost 3 levels inside. Guests have access to the entire second floor which includes a lovely balcony where you can catch the most epic sunsets from.
Most reviews of the place have said that the owner is extremely courteous and goes out of his way to make his guests comfortable, which is always what you want to hear when booking a holiday home for yourself and your group!
Romantic Vacation Rental | 2BR Cottage
- $$
- Charming island style cottage
- 2 Guests
- Located in East End, Grand Cayman
Romantic and sparkling clean, this cottage is part of the Grape Tree Cove on the East End of the island, which means that you get to be somewhere more quiet than the famous Seven Mile Beach.
The beach itself is known for its soft white sand and gorgeous turquoise blue waters, while the area is known to be a sleepy fishing village known for snorkelling and scuba diving, with amazing eateries and bars.
The house itself has one bedroom and sleeps just two guests. There’s a full kitchen as well as a small eating area. The property is basic but kitted out with everything you need, plus it’s direct access to the beach is what makes it special.
Beautiful Vacation Rental in The Cayman Islands | 3BR Pink House
- $$
- Villa with panoramic views
- 6 Guests
- Located in Rum Point, Grand Cayman
This eye catching Pink House sits on its own private, reef protected, white sandy beach, which makes it super secluded, while being close to all that Rum Point has to offer. The villa has a beautiful, large outdoor area that is professionally landscaped to include bright flowering Bougainvillea, palm trees, and a lush grass lawn.
The renovated pool has a large deck that looks out directly on to the Caribbean. Completely surrounded by vegetation and palm trees, there is a very pleasing tropical vibe from the entire rental.
Don’t Forget Your Cayman Islands Travel Insurance
ALWAYS sort out your backpacker insurance before your trip. There’s plenty to choose from in that department, but a good place to start is Safety Wing.
They offer month-to-month payments, no lock-in contracts, and require absolutely no itineraries: that’s the exact kind of insurance long-term travellers and digital nomads need.
SafetyWing is cheap, easy, and admin-free: just sign up lickety-split so you can get back to it!
Click the button below to learn more about SafetyWing’s setup or read our insider review for the full tasty scoop.
Final Thoughts
The Cayman Islands is a great place to enjoy some much-needed sun, sea, and white sand beaches. With its warming hospitality and endearing locals, there’s not much that can go wrong when you choose the Cayman Islands to vacation in.
However, choosing a vacation rental in the Cayman Islands is definitely one way to make sure you have all the comforts you need to make sure your trip is a memorable one.
If you’re ever stuck for ideas, you could always pick my overall favourite holiday home, the2BR Beach Home that is just 20 steps away from the beach. Not only is it affordable, but it’s cute and packed with everything you need.
Do you have a favourite on my list? Let me know in the comments.
And for transparency’s sake, please know that some of the links in our content are affiliate links. That means that if you book your accommodation, buy your gear, or sort your insurance through our link, we earn a small commission (at no extra cost to you). That said, we only link to the gear we trust and never recommend services we don’t believe are up to scratch. Again, thank you!
