Cayman Islands comprise of three isles - Grand Cayman, Little Cayman, and Cayman Brac. It is located in the western portion of Caribbean Sea, just south of Cuba. Starfish Point has shallow water, making it easy for you to admire vibrantly colored starfish. Queen Elizabeth II Botanic Park has a garden rich in flora and fauna. Cayman Crystal Caves, meanwhile, is an area you can explore if you want to experience spelunking. Of course, you can’t spend time here without hitting the beach. Seven Mile Beach is the perfect place to head to if you want to play water sports or just soak up the sun. However, you don’t have to hit the beach to take a dip. Book one of the best villas with private pool in the Cayman Islands so you can swim anytime you want during your stay.
We handpicked these listings carefully, considering (wherever possible) host status, recent guest reviews, location, accommodation type, prices, availability of dates, decor, and access to private pool. The image galleries get refreshed with the latest updates regularly. They were last updated on April 14, 2024.
1. Oceans Edge SeaSide Estate, Bodden Town (from USD 2500)
Oceans Edge SeaSide Estate has an infinity pool that is spacious and overlooks the sea. A hot tub along with a deck can be found right by it. The deck has lounge chairs and a grill so you can enjoy a cookout as you take in the views. You can rent the main villa or the whole estate if you need more space.
If you want to hit the beach, the closest one, Spotts Beach, is just a five-minute drive away. Seven Mile Beach is a 15-minute drive away, as is the Botanical Gardens.
Top guest reviews
Amenities & Room:
the view is stunning the pool and hot tub inviting and rooms were luxuriousCleanliness:
we felt very secluded though clean well keptHost:
great service from caretakerthanks to the owners for allowing us to share in their piece of paradiseeveryone is so helpfulthe property manager was very attentive and helpful with anything we needed during our staygreat staff luxurious accommodation private quiet spacious everything we needed for a memorable family reunionRead more reviewsLocation:
this is a beautiful locationwe had an amazing stay location perfect distance from airport shopping and getting around islandclose to beach grocery and easy access to restaurantsif you want to truly get away from it all this is the place for you
2. Villa Emmanuel, North Side (from USD 995)
Staying at this beachfront home will provide you with two options where you can swim - the sea and the pool. The poolside has sun loungers so you have spots to relax while cooling off. You will enjoy views of the setting sun on the horizon. Beach towels are also provided for guests’ use.
This centrally located villa is in a quiet neighborhood that nonetheless puts you close to attractions in Grand Cayman, including Stingray City, Rum Point Beach, and Kaibo Yacht Club.
Top guest reviews
Amenities & Room:
nice large screened in area right in front of pool deckthe pool and beach area were perfect for playing with/watching the grandchildrenthe pool worked great for our 2 and 6 year old grandchildrenCleanliness:
it was very clean and the beds were comfortablethe pool was clean and comfortable and pool company even cleaned it once while we were thereRead more reviewsLocation:
very nice house on a beautiful location and beachloved grand cayman loved the location and the peopletrade winds were from ens so waters on beach were always smooth and calm
3. Sun Serenity, North Side (from USD 3500)
This spacious villa has an equally large pool just a few steps away from the beach. If you want to soak under the sun, you can go for a swim in the sea. Paddleboards and kayaks are provided if you want to paddle your way around the area. If you prefer to play in the shade, the pool, which comes with immersed stools and loungers, awaits you.
Once you’ve had your fill of the water, you can head indoors and have fun in the game room, which is equipped with a foosball table.
Top guest reviews
Host:
my entire family enjoyed the sun serenity villa and i especially loved that the home was kid-friendlyRead more reviewsLocation:
beautiful property great for a large family lots of things to do close by
4. Southern Reach, Cayman Brac (from USD 238)
Southern Reach has a ground pool right on the porch. It has a maximum depth of 5 ft (1.5 m), which makes this a good option if you prefer shallower pools. There’s also a bench installed on one end where you can sit around. Meanwhile, the porch has two hammocks where you can take a snooze.
You can enjoy views of the sea even if you’ve already made your way inside through the sliding doors. Besides being furnished with the essentials, the villa includes books, CDs, and DVDs that you are welcome to use to entertain yourselves.
Top guest reviews
Cleanliness:
property was clean and as describedsouthern reach was spacious clean and privateeverything was absolutely beautiful people are very friendly and the island is very cleaneverything was absolutely beautiful people are very friendly and the island is very cleanHost:
paul (owner) made sure everything was in order for our arrivalRead more reviewsLocation:
we loved the pool and secluded location
5. Endless Breeze, East End (from USD 375)
This beachside house provides relaxing views of the sea from the pool and the gazebo. If you’re lucky, you may be able to witness turtle eggs hatching and the hatchlings making their way to the water. Snorkeling and fishing can be enjoyed right by the property.
Despite its quiet location, this property actually puts you near restaurants so you can try local cuisine. The house has two outdoor security cameras installed for safety, but you can request to have these turned off for privacy. High-speed internet is available here so you can stay connected even while on holiday.
Top guest reviews
Amenities & Room:
The kids enjoyed the pool each day----so that pretty much satisfied their need for waterThe pictures do not do it justiceJim provided towels sheetsThe kitchen is well equipped and the home is welcomingThe layout is perfect with 3 bedrooms and 3 bathrooms with space for everyoneCleanliness:
We enjoyed the pool which was very cleanThe house was beautiful clean and offered us everything we needed for our stay; we all felt at home immediatelyHost:
Jim was very responsive to our questions and gave us a warm welcomeThe owner Jim is great to work and is very responsiveJim was always quick to answer any questions and easy to communicate withthe more we appreciated the designThis was very helpful as the island is definitely not cheapRead more reviewsLocation:
It's easy to get around the island from hereRestaurants were great within 20 minutes of the house if not closerbut also close to several great restaurantsThe property is away from the busy streets of Seven Mile Beach but close enough to drive to everythingThis property is in a great location and is beautiful
6. Tropical Runaway, Cayman Brac (from USD 375)
The pool area on this stunning property is shaded so you can take a dip without being overly exposed to the sun. The waterfalls only add to the fun that you can have fun in the water. Outdoor seating is available where you can relax and enjoy the sea breeze.
Diving enthusiasts will want to consider staying in this villa, which has rinse and drying stations for scuba divers. A dive shop is easily accessible from the property. Animal lovers will want to keep an eye out for local wildlife, including turtles.
Top guest reviews
Cleanliness:
the place was clean easy to find and the hosts were greatHost:
karen the owner was great to deal withkaren the owner was great to deal withwe enjoyed the pool and beach and would highly recommend this property karen and ray are gracious hostsdefinitely paradise great communication with the ownersRead more reviewsLocation:
this is a lovely place to staywe were surrounded by the naturally positive cayman brac energy at this placeit's worth it wonderful wonderful place
7. Coral Beach Villa, Cayman Brac (from USD 385)
Check out this rental if you or someone you’re traveling with someone who has mobility issues. This property can accommodate wheelchairs and scooters. It is also equipped with amenities for the benefit of guests with disabilities, such as grab bars and ramps.
The pool and the hot tub sit right by the sea, affording you relaxing views as you soak into the water. Steps are available to make entering and exiting the pool easy while also providing a space for children to splash around. Chaise loungers are close by if you prefer to relax out of the water.
Top guest reviews
Amenities & Room:
the property had all the amenities we needed and was very comfortableHost:
also the owner joy and the property manager mrRead more reviewsLocation:
the perfect place to explore the island and have a family getaway
8. Oceanfront villa with access to private beach, West Bay (from USD 578)
Privacy is the name of the game where this property is concerned. This rental is in a gated complex. The villa not only gives you access to a private freshwater pool, but also a private beach, which is just a few steps away from the pool. Just close by is a colorful reef where you can snorkel.
A grocery store is just three minutes away if you need to pick up supplies, including ingredients for the dishes that you will be whipping up in the kitchen.
Top guest reviews
Amenities & Room:
the a/c internet and appliances all just work greatthe pictures does not do it justice huge amount of space modern furnishings well-equipped/supplied comfortable and cleansmall private pool that overseas private beach incredible views in a peaceful areavery comfortable beds with plenty of space for our family of fiveamazing view from apartment right out over the pool looking at the oceanCleanliness:
the condo unit is quite spacious clean and comfortableHost:
dynamite accommodations provided by a wonderful host and property managerme app was very helpful to navigatethe home exceeded our expectations in that it was very accommodating and cleanRead more reviewsLocation:
love the location and the housethe location is better than picturedphilips house and the location are perfectamazing property in a fantastic locationwe had a wonderful vacation in cayman and enjoyed the location and house
Superhost
9. Coco Kai, North Side (from USD 785)
Coco Kai is a spacious family-friendly villa that includes a crib and a high chair among its amenities. The saltwater pool is heated, allowing you to stay comfortable while in the water. A hot tub is also available for relaxation.
Snorkeling gear and life jackets are provided so you can marvel at the coral reef right behind the villa. Six kayaks are also available if you want to explore the water. Fishing poles are provided if you want to try your luck at catching some fish.
Top guest reviews
Amenities & Room:
beds were comfortable and it was nice having a washer/dryerthere are modern appliances and the furniture is all clean and comfortablebeautiful couches and comfortable bedsCleanliness:
beautiful and clean villa as picturedawesome place clean everything we neededthe house is very clean and well maintainedhouse is clean comfortable and spacioushouse was spotless and in great shapeHost:
jason was very helpful and accommodating of our requestsjason was super helpfuljason is a great responsive hostdefinitely a 5-star host and homejason was a great host- very responsive and provided good advice and local tips prior to our arrivalRead more reviewsLocation:
great location to get away from it allgreat place away from the hustle but not far to all points of interestbeautiful location has everything you need to have an enjoyable vacationgreat location and property well equipped with games and kitchen needsbeautiful home amazing location and an attentive and generous host
10. Casa Avi, Bodden Town (from USD 990)
Casa Avi is an artistically decorated home on a secluded beach, which makes this a great option for travelers looking for peace and quiet. It comes with a saltwater plunge pool, which is just the right size for you to take a dip in and cool off.
Alternatively, you can walk over to the beach and swim in the sea. Enjoy sights of the sea from various parts of the house, including the patio. Feel free to take a nap outside on one of the hammocks or just rest and relax on a beanbag.
Top guest reviews
Amenities & Room:
the furniture is classy and comfortablethe extra pull out bed was very comfortableRead more reviewsHost:
the hosts are wonderfulthe host was always available courteous and responsivethese hosts will go above and beyond to make sure your stay is unforgettable
Rest and relax in the Cayman Islands
Cayman Islands is home to various beaches and clear water. In the above-listed accommodations, you can just take a few steps to take a dip in the pool even if you don’t want to head out to go for a swim.
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