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

Guest favorite
A charming yellow home is nestled among palm trees, featuring a spacious porch with seating and a hammock. The inviting pool area is visible nearby, surrounded by well-manicured greenery and white sand, under a bright blue sky dotted with fluffy clouds.
Home in Rum Point
4.88 out of 5 average rating, 56 reviews

Luxury 3bd Beach Front, # 5 Yellow, Stunning Views

DustinRating, 5 stars2 months ago
The home and location were really nice. The North Side of the island is pretty far from everything which is nice if you want quiet, you'll have the whole beach to yourself. There are a few decent restaurants within 10 minutes. Most activities are 30-45 minutes away. We really enjoyed our stay, but 1.5 hours of driving every day to and from activities got kinda old after a few days. If you plan to spend most of your time at the house/beach/pool this is a great place to stay.
Superhost
Lounge chairs sit poolside, offering a view of the ocean waves. The bright sky contrasts with the tranquil water, while the surrounding deck features a patterned edge. The scene is designed for relaxation and enjoyment of the coastal ambiance.
Home in Cayman Brac
4.73 out of 5 average rating, 55 reviews

Villa Villekulla - Relax Poolside

GingerRating, 5 stars2 months ago
A beautiful spot on Cayman Brac. We watched the sunrise every morning. Very clean, accurate photos and description, comfortable beds, gorgeous views. The pool needed some attention while we were there and the host was super responsive. As previously mentioned in other comments, the pool area is very sunny during the afternoon. We had an amazing stay and would stay again when visiting Brac.
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, 9 reviews

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

DanielRating, 5 stars2 weeks ago
Beautiful home! The place was spotless and had great amenities. The pool and backyard area was super nice. Julie was very responsive and accommodating. I would definitely stay again!
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 stars1 month 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 refreshing pool is framed by palm trees and offers a view of the ocean beyond. The surrounding area features colorful buildings and landscaped pathways, creating a serene environment for relaxation. The clear blue water invites enjoyment under a clear sky.
Home in Grand Cayman
4.92 out of 5 average rating, 26 reviews

3 Bedroom Beach House with Pools

LeeRating, 5 stars2 months ago
Everything as advertised! Beautiful, peaceful and far from the crowds. If you like driving around the island and having a great place to come back to, this is where you want to be!
Top guest favorite
Home in Stake Bay
5 out of 5 average rating, 60 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!
Top guest favorite
A tranquil shared pool is depicted, surrounded by lush greenery and tall palm trees. Comfortable lounge chairs are positioned around the water, inviting relaxation. The clear blue sky reflects on the surface of the pool, enhancing the serenity of the outdoor space.
Home in George Town
5 out of 5 average rating, 8 reviews

Hidden Hideaway House -7 mile -2King/1Queen- Pool

ElizabethRating, 5 stars4 months ago
Monika's house was the perfect place to spend a week in Grand Cayman. The location was perfect and close to the grocery store, across the street from the beach and within walking distance to many restaurants including Camana Bay. We enjoyed the pool, large backyard and safety of the residential neighborhood. The house was "as described" and we felt that we had everything we needed for the week. Thanks again!
Guest favorite
A bright living area features a gray sectional sofa adorned with colorful cushions in yellow, teal, and pink. A glass coffee table is positioned on a patterned rug, while a red lamp provides light. The open layout includes glimpses of the dining area and kitchen.
Home in Patricks Island
4.97 out of 5 average rating, 29 reviews

Seabreezes-Your Oceanside Escape

TerryRating, 5 stars1 month ago
Phillip’s place was perfect for our stay. It was close to groceries, restaurants, snorkel spots and Georgetown. His property is well equipped, very clean and comfortable. Bed was great, porch was fantastic spot to enjoy morning coffee and there was even a hose available to wash down our snorkel gear each day. Loved that beach chairs, beach towels and more were available for our use. Neighbors are very friendly, we typically had the pool to ourselves, loved the Oceanside boardwalk. Would definitely recommend to any group of 1 or 2 travelers.

Condo rentals with a pool

Superhost
An outdoor dining area is visible, featuring a glass-topped table surrounded by six gray chairs. Lush greenery frames the space, and a view of the ocean can be seen in the background, with palm trees swaying gently in the breeze.
Condo in Seven Mile Beach
4.71 out of 5 average rating, 7 reviews

Regal Beach Club #114

KaylaRating, 5 stars15 months ago
We had a great trip. Starting with the welcome packet, that was very detailed. The location was outstanding. We were steps to the pool or ocean. The place is very laid back and all the quests are very respectful. There were so many options for food and shopping within an easy walking distance. We enjoyed Peppers and got take out from Chicken Chicken and even had a sunset dinner next door at the Marriott. All the communication with the host was so helpful.
Guest favorite
A pool is set beside an open terrace, leading to a sandy beach and the ocean. Lush palm trees are visible, gently swaying in the breeze. The clear blue water of the pool reflects the sky, creating a serene outdoor environment.
Condo in Bodden Town
5 out of 5 average rating, 5 reviews

Lovely Ocean Front Sea Palm Villa #2

DeanneRating, 5 stars1 month ago
Beautiful location free from overwhelming crowd and noise. It was easy to drive to local beaches, and explore other parts of island. This was the perfect center location geographically to either side of island.
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
4.85 out of 5 average rating, 34 reviews

Enjoy Sunsets at Cayman Reef Resort - 7 Mile Beach

SaraRating, 5 stars2 weeks ago
This place was great! Soooo close to the beach, literally you go downstairs and take just a few steps. Pool was nice, too. Cabana Bay was easy walking distance along a nice footpath. Gabrielle was super friendly and helpful with any questions I had. To accommodate my flight times, I was able to check in early and check out late as well. Would highly recommend to stay here. I love the roosters and hens, too! I hope they always get to stay. They aren't a bother and no one should consider them as such. Although they can't be fed there, that is still their home. ❤️ 🐓
Superhost
Condo in George Town
4.87 out of 5 average rating, 166 reviews

Beautiful Modern Condo on 7 Mile Beach

TessaRating, 5 stars1 week ago
Condo was exactly as advertised. Large balcony was great for drying beach towels and snorkeling gear. AC worked great. Steps to pool and beach. Plenty of beach and pool lounge chairs and umbrellas. Can walk up or down the beach from the resort beach. Host was quickly responsive to our texts.
Top guest favorite
An expansive pool area is featured, surrounded by modern buildings and lush landscaping. Lounge chairs are positioned along the pool's edge, reflecting the vibrant colors of the sunset. Umbrellas provide shade, enhancing the space for relaxation and enjoyment.
Condo in Seven Mile Beach
5 out of 5 average rating, 29 reviews

Seven Mile Beach Area, Kyle's Condo @ ONE Resort!

EugeneRating, 5 stars3 weeks ago
Great stay! The place was clean, comfortable, and exactly as described. Check-in was easy, and the host was responsive and helpful. Would definitely stay here again.
Guest favorite
A balcony view showcases a large swimming pool surrounded by lounge chairs and umbrellas. In the foreground, a thatched-roof gazebo is visible. Lush greenery and palm trees frame the scene, while the façade of the condominium buildings provides a backdrop beneath a blue sky with scattered clouds.
Condo in George Town
5 out of 5 average rating, 12 reviews

Condo-Sunset Cove-Ocean | Pool | Seven Mile Beach

AnnaRating, 5 stars1 month ago
The condo at Sunset Cove was just perfect for our family of 3! Our 8 year old loved swimming in the pool and the ocean. There were lots of kids to play with and everyone was so friendly! I would recommend bringing a float with you to use in the pool. Having the swim up bar/restaurant was so great. The food was delicious for bar food. It is walkable enough especially for the price. Super clean, quiet, beds are comfortable. We will be back!!
Guest favorite
The view features a serene courtyard with a swimming pool surrounded by lush greenery. Palm trees frame the area, and lounge chairs are positioned near the pool. Light-colored buildings with aqua roofs are visible in the background under a bright blue sky.
Condo in George Town
4.88 out of 5 average rating, 58 reviews

3 Bedroom 2 Bath Condo right on 7 Mile Beach

AngeloRating, 5 stars1 month ago
Gary and Shannon really thought of everything! Having traveled around the world, these hosts had way more things for their guests than most. For example, snorkel gear, beach toys for kids, sports and games, phone/table charger in every room. Stocked with plenty of items to get you in the door and your vacation started. Having been to the Cayman Islands in the past, I was pleasantly surprised to see the water and beach were as beautiful as ever ! Crystal clear and loaded with life. Had a great time with a bunch of family and we all couldn’t be happier with the accommodations. Gary and Shannon delivered the goods and I am hoping for a repeat visit in the near future.
Superhost
Condo in George Town
4.91 out of 5 average rating, 98 reviews

Beautiful Beachfront 2BR Condo.

HeatherRating, 5 stars2 months ago
The condo was absolutely beautiful. We loved the view from the kitchen/living room right out to the ocean. It had everything we needed to be able to cook some meals at the condo during our stay. The pool was big with plenty of room for everyone who wanted to enjoy it. And we also enjoyed having access into the water right in front of the condo- we were able to snorkel the ship wreck a few times. The outdoor shared patio’s were also great to have access to and watch the sunset from. We appreciated having access to the washer and dryer as well. They also have beach chairs, small cooler and other beach supplies if you need them- which is great so you don’t have to travel with those items or rent them. There was construction going on at the large building beside the condos - it didn’t bother us too much because we were always out and about during the day exploring. Parking is tight, so a smaller car is best - we backed into the spot which was much easier to get in/out. Loved this place!

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