Vacation rentals with a pool in Cayman Islands

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Popular amenities for Cayman Islands rentals with a pool

House rentals with a pool

Top guest favorite
An aerial view captures the spacious layout of the property, surrounded by lush greenery. The inviting pool glimmers amidst the tropical landscape, with the blue ocean visible in the background. Nearby homes and vibrant trees contribute to the serene environment.
Home in George Town
5 out of 5 average rating, 10 reviews

Beautiful 4 BR/3 BA South Sound Home w/pool.

JeremyRating, 5 stars4 days ago
We had two families with little kids staying at Julie’s house and it was perfect for our group. The kitchen is well equipped. Bedrooms and bathrooms were clean, comfortable, and as advertised. The pool is great. Great spot!
Top guest favorite
The beachfront home is showcased from an aerial view, highlighting its two-level structure with a white roof. A spacious sun deck is visible, featuring loungers and steps leading directly to the sandy beach, framed by palm trees and lush greenery.
Home in Rum Point
5 out of 5 average rating, 24 reviews

Beachfront Retreat w/ Pool – Rum Point Paradise

SamanthaRating, 5 stars2 weeks ago
The house was beautiful and clean. The host responded quickly and we had no issues. The view was incredible and within walking distance of a nice beach and restaurant. The neighborhood is safe, quiet and peaceful! Worth every penny!
Guest favorite
A brightly colored two-story villa features a spacious deck and a pool, surrounded by tropical greenery. The ocean is visible in the background, with sandy beach leading to the water. The building has a red roof and multiple seating areas for relaxation.
Home in KY
4.73 out of 5 average rating, 15 reviews

Parrot-ise 4 Bedroom Oceanfront Villa in Cayman Ka

MelanieRating, 5 stars3 weeks ago
Parrot-ise is wonderful! Beautiful house. Beautiful pool. Lovely neighborhood. We pulled gorgeous conch shells out of the ocean and enjoyed the private beach. There is coral, so water shoes will increase your enjoyment. We will definitely return! Thank you for a wonderful family vacation!
Top guest favorite
A serene outdoor space features a turquoise swimming pool surrounded by a tiled deck with several lounge chairs. A light-colored home with large windows and a shaded patio area offers views of lush greenery and a clear sky.
Home in West Bay
5 out of 5 average rating, 24 reviews

Oceanfront Oasis Home with cottage & private pool

StevenRating, 5 stars2 months ago
We came for spring break and absolutely loved the place. First, the view is absolutely fantastic! Being able to wake up and enjoy our morning coffee with the views of the ocean were a great way to greet the day. The pool was well used on our trip and it was both warm and clean! Loved the built in seats in the pool. The place was located near some great restaurants and close enough to everything that we didn't spend a lot of time getting from place to place. Chelsea was extremely helpful and very responsive. We will be back for sure!
Guest favorite
A spacious living area presents large sliding glass doors, allowing natural light to fill the room. A comfortable sectional sofa and stylish coffee table are positioned on a neutral-toned area rug. Lush greenery is visible outside, enhancing the sense of tranquility.
Home in Grand cayman
5 out of 5 average rating, 5 reviews

3 Bed Brand New by 7 Mile Beach!

JonathanRating, 5 stars2 weeks ago
I was on island for a quick trip. This end-unit townhouse was spotless, modern, conveniently located and our host was friendly, responsive and proactive. Highly recommended!
Top guest favorite
A spacious living area features large glass windows that provide panoramic ocean views. A balcony extends off the room, allowing direct access to the tranquil outdoors. A dining area is visible in the foreground, complementing the bright and airy design.
Home in Bodden Town
5 out of 5 average rating, 51 reviews

Casa Avi - Shoreline Sanctuary in Grand Cayman

JoanRating, 5 stars5 days ago
Comfortable, unique and spotless! Family oasis! Magical property! My little family has stayed on a variety of spots on this island over the years and this is our favorite. A delightfully private beach. We went snorkeling every day and saw a variety of tropical fish. We also took the kayak farther out and spotted stingrays and tarpon. Nearby Potts Beach is an easy ten minute drive and we spotted sea turtles! We cooked the majority of our meals on site, so the nearby Bodden Town Shopping Plaza is convenient. The house itself is a perfect vibe, its design and construction in conversation with the landscape. Avril Ward's art creates a distinctly vibrant sense of place. Swoon inducing views from every angle, inside and out. We made good use of the lower level, which opens in all directions. There's a gorgeous pool outdoor shower, so the transition from sea to land is as comfortable as it gets. A true Caribbean paradise. We'll definitely return.
Guest favorite
A vibrant yellow villa stands beside a sandy beach, framed by palm trees and lush greenery. The clear blue sky and fluffy white clouds create a serene backdrop, while lounge chairs are positioned on the sand, inviting relaxation by the ocean.
Home in North Side
4.96 out of 5 average rating, 50 reviews

Oceanfront Dreamsicle Villa w/Outdoor Living Area

ReedRating, 5 stars2 months ago
To make a long review short, well worth the money. It's a huge house, it could comfortable sleep 6-8 people and not be crowded. Each bedroom has it's own bathroom. Every time we needed something, even things you wouldn't expect like a coffee bean grinder. toaster oven, or snorkel, it was there. The sandy beach was maybe 20 yards to the East. It's worth the price. Would go back again and again.
Top guest favorite
Home in Stake Bay
5 out of 5 average rating, 61 reviews

Modern Oceanfront, 2Primary Suites, sleeps 6, pool

ShahlaRating, 5 stars1 month ago
Our stay at Tides End, Cayman Brac was nothing short of spectacular. The home itself was absolutely stunning—beautifully designed, immaculately clean, and equipped with every amenity you could possibly need (and more!). The location couldn’t have been more perfect—peaceful, private, and surrounded by breathtaking views. From the moment we arrived, we felt completely at ease. The hosts were incredibly gracious and attentive, making sure we had everything we needed to enjoy our stay to the fullest. Their warm hospitality added a personal touch that made the experience even more special. Whether you’re looking for a relaxing escape or a base to explore all that Cayman Brac has to offer, Tides End is the ideal choice. We can’t wait to return!

Condo rentals with a pool

Top guest favorite
A balcony view features two chairs facing a vibrant sunset over the ocean. Two glasses and a bottle are positioned on a small table, with the golden sun reflecting on the water below. The calm waves are visible in the foreground.
Condo in West Bay
5 out of 5 average rating, 81 reviews

Oceanfront: 2 pools, diving & snorkeling on-site

SandyRating, 5 stars3 weeks ago
My husband and I enjoyed an amazing 10 days in West Bay. Staying in Sean's oceanfront was the highlight! The view from the full lenghth windows was spectacular: watching the ocean, gentle, rolling waves, and sunsets were both peaceful and breathtaking. The snorkeling at Lighthouse Bay, just steps from the penthouse was full of delights: comical squid, a rainbow of parrotfish, cowfish, angelfish and tangs! Many other fantastic snorkeling spots, such as Eden Rock, Macabuca and Cemetary beach were close by. The penthouse itself was, as other have said both tastefully decorated, pristine, and comfortable! The bedroom was a dream and the kitchen fully outfitted for cooking and dining! If we ever return to Grand Cayman, this penthouse is where we would stay! As others have commented this condo's description and photos were totally accurate, not fully capturing its magic!
Guest favorite
A serene view of the ocean can be seen from the terrace, highlighting clear turquoise waters meeting a sandy shore. The scene is complemented by a bright sky, where distant boats are visible, suggesting a tranquil coastal environment.
Condo in George Town
4.86 out of 5 average rating, 37 reviews

Enjoy Sunsets at Cayman Reef Resort - 7 Mile Beach

PatrickRating, 5 stars4 days ago
Our family of 5 found the accommodation ideal for us with three bedrooms and two bathrooms. Plenty of space in the kitchen and living/dining room areas. Kitchen was well stocked with cooking items and utensils. Beautiful views from the balconies. Great location to some nice restaurants. Close parking spot. Beach towels provided. Cable TV and some streaming apps are available. Even though there was no accessible beach immediately in front of the condo, there is a beach immediately to the right of the property. However, we drove to the more popular Seven Mile beaches just north of the condo (ex. Governor’s and Cemetery Beach). Definitely close to some good walking restaurants and 10-15 minutes from the airport. REM provided good communication prior to our arrival. All we had to do was lock the door and they took care of all cleaning, including trash. If you’re looking for a convenient location close to Seven Mile Beach, I would not hesitate to rent this property.
Top guest favorite
A well-lit hot tub is positioned within a landscaped area, surrounded by tropical plants and blooming flowers. The glowing blue water reflects the evening sky, while palm trees frame the view. Nearby benches invite relaxation, creating a serene atmosphere in the outdoor space.
Condo in George Town
5 out of 5 average rating, 42 reviews

Regal Beach Condo #233 on Seven Mile Beach

LisaRating, 5 stars1 month ago
I had a fantastic stay at Maggie's place. The unit was exactly as described- airy, beautifully furnished, very clean and incredibly comfortable. The location could not have been better- just steps from the beautiful beach and great local restaurants. Maggie was wonderful, thoughtful and attentive, checking in to make sure everything was perfect. She went the extra mile with small touches that made the stay extra special. I highly recommend it and would only want to stay here the next time I'm in Grand Cayman. Thank you again Maggie for a wonderful experience!
Guest favorite
A community pool is surrounded by a spacious deck featuring beige concrete. Lush green trees provide a natural backdrop, while the clear water invites relaxation. A gentle slope leads into the shallow end, complemented by a ladder for easy access.
Condo in Savannah
4.92 out of 5 average rating, 62 reviews

Seaing Spotts: Beachfront Seaside retreat! Cayman

Dawn Rating, 5 stars2 months ago
This condo is spacious and beautiful. A quick walk to the beach with a beautiful view. We didn’t see as much snorkeling but that’s ok. The home decor is so cute! The only thing I’ve had in every other Airbnb is hand soap to wash your hands after going to the bathroom. This place has none. Just an FYI. Everything else was perfect.
Guest favorite
A clear blue swimming pool is surrounded by lounge chairs and shaded by colorful umbrellas. A pink flotation device rests on the water's surface, reflecting the sunlight. Lush greenery frames the pool area, enhancing the inviting outdoor space.
Condo in George Town
4.93 out of 5 average rating, 161 reviews

Seven Mile Beach with Soul

AbrahamRating, 5 stars1 month ago
Reno and Agata were super supportive of our requests. Great location and very comfortable. The AC was refreshing after a day in the heat. They had all amenities to make a stay comfortable. The beach is steps from the place along with shopping stores and restaurants. The apartment was clean and had everything we needed for a comfortable stay. Thank you.
Guest favorite
Condo in West Bay
5 out of 5 average rating, 41 reviews

Panoramic Ocean views and Magnificent Snorkeling

AnthonyRating, 5 stars2 weeks ago
Great place and my family really enjoyed the stay. Snorkeling off the back is only recommended for the experienced and you definitely have to wait for a calm day with how wind to do it safely. Luckily lots of great beaches minutes down the road by car. Great location, easy access to the Turtle center and the docks for Stingray city tours. Great grocery store 3 minutes away. Pool was great and the kids used it every night. Loved it and would return!
Superhost
The image captures a tranquil beach scene with soft, golden sand meeting clear turquoise waters. Gentle waves lapping at the shore create a soothing atmosphere, while the horizon blends seamlessly into a bright blue sky dotted with a few clouds.
Condo in Grand Cayman
5 out of 5 average rating, 3 reviews

Cayman Reef Resort 7-Mile Beach1-Bed 1-Bath Condo

PaulRating, 5 stars3 months ago
Gary and Shannon's first floor condo is superb in many ways. The beach is right outside your door, and there is a manmade sandy area with enough lounge chairs to accomodate the complex. The grounds and beach area are maintained daily so the resort is spotless. Location is amazing for anything you want to do in Grand Cayman including very short and easy ride to and from the airport. Washer and dryer are brand new. I would rent this condo again without even looking elsewhere when we return. Wendy's and Burger King if you have little ones or need a familiar bite are literally right across the street. Didn't spend too much time at the pool but it was in line with everything else I've mentioned. Paul and Sandy Esposito
Guest favorite
A large swimming pool is surrounded by well-maintained greenery and palm trees. Blue lounge chairs and umbrellas are positioned by the poolside, providing ample shade and relaxation options. The backdrop features a contemporary condo complex with balconies overlooking the grounds.
Condo in George Town
4.95 out of 5 average rating, 183 reviews

Cayman Reef Resort on Seven Mile Beach

KarenRating, 5 stars4 weeks ago
We loved the condo, the location, the decorations, and the landscaping of the complex. The condo had everything and more for what we needed. It had every possible amenity, utensils, soap, shampoo, conditioner, iron, internet...the list goes on and on. The location was extremely convenient to the beach, food, and other places nearby. We would absolutely consider staying here again next time.

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