Holiday rentals with a pool in Rum Point

4.99 out of 5 average rating, 331 reviews

The exterior of the cottage is framed by vibrant tropical plants and flowering shrubs, showcasing a blend of lush greenery and colorful blooms. The white structure features a sloping roof, supported by two elegant columns at the entrance.

Cottage in West Bay

Luxury Cottage, 1bd/1ba steps to Pool+7 Mile Beach

Our Queen Cottages are part of the Botanica collection of award winning island style cottages. This unit has a private outdoor dining and garden shower. At Botanica, our focus is on casual luxury, dreamy details and high end amenities. Property highlights includes a resort style pool with heated spa set in a tropical oasis. We also offer a complimentary shuttle in our vintage Land Rover Defender to nearby beaches. Be sure to check out our other listings under my profile. Non Smoking Complex

An open living area features a modern kitchen with white cabinetry and stainless steel appliances, complemented by a wooden bar with two stools. A comfortable gray sectional sofa and a unique wood block coffee table enhance the inviting atmosphere, with natural light illuminating the space.

4.9 out of 5 average rating, 122 reviews

Starfish Paradise Beachfront Condo

Starfish Paradise is a 2 bed, 2 bath ground-floor unit with direct beach access. Situated in the quiet, tranquil area of Kaibo with stunning ocean views. Just steps from a beach bar, restaurant, and coffee shop. Enjoy world-class diving, Stingray City, bioluminescent tours, and snorkeling—or simply relax on the sand. Whether it's a romantic escape, family trip, or work-from-paradise stay—Starfish Paradise has it all. 💫 Special rates from August to October—book your slice of paradise now!

Place to stay in Rum Point

An expansive infinity pool reflects swaying palm trees under a sunset sky. Lounge chairs are arranged along the poolside, inviting relaxation by the water. The serene atmosphere is enhanced by the soft colors of the sky and the tranquil water's surface.

5 out of 5 average rating, 24 reviews

Yippee Kai Yay Beachfront oasis

Welcome to Yippee Kai Yay /Kaibo Sunset - Unit B17! Situated within the prestigious development of Cayman Kai, where us locals go to unwind and relax ,Kaibo Sunset is the premiere vacation getaway in Grand Cayman with fun and activities at your fingertips! For the water enthusiast, it is paradise, with soft white sandy beaches fringed with coconut and royal palms intermixed with carefully chosen tropical plants ,a beautiful infinity pool and hot tub for the true Cayman Caribbean experience.

A sandy beach is framed by tall palm trees, with a relaxing hammock suspended between them. Two lounge chairs are positioned nearby, offering a peaceful spot to enjoy the ocean view, while calm waters stretch into the distance under a clear blue sky.

4.95 out of 5 average rating, 42 reviews

"Mai Kai" Recently renovated Oceanfront Condo

“Mai Kai” is a beautiful renovated 2 bedroom, 2 bathroom oceanfront condo at Kaibo Yacht Club II, in the heart of the Cayman Kai community. At ground floor level you have direct easy access to the gorgeous beach through the private screened outdoor patio. Steps away is the large pool and hot tub to laze away the days, two Kayaks are also included for your use and enjoyment. So whether you are seeking a romantic getaway or a family fun filled vacation "Mai Kai" and surroundings will deliver!

A tranquil scene at sunset features palm trees silhouetted against a colorful sky, reflected in a serene pool. Lounge chairs are positioned near the water's edge, with a sandy beach leading to the horizon where boats can be seen in the distance.

5 out of 5 average rating, 61 reviews

Seaside Serenity at Cayman Kai

Forget your worries in this spacious and serene space. Kaibo Yacht Club Phase II is a small, 30-unit complex on the quiet side of Grand Cayman. Guests love the peacefulness of Cayman Kai, located on the opposite side of the island from Seven Mile Beach. A rental car is strongly recommended to fully appreciate island-wide attractions and to enjoy the many restaurants. Kaibo Restaurant, next door, offers many options. If you are a legal resident advise us at booking for tourist tax waiver.

A screened-in covered patio features a wicker hanging chair and a sofa adorned with light cushions. Large glass doors provide unobstructed views of palm trees and the beachfront, while vibrant flowers add a touch of color to the tranquil space.

4.97 out of 5 average rating, 36 reviews

Newly Renovated 2 Bed Beachfront Condo w/Pool+Hot

Nestled in the heart of serene and picturesque Cayman Kai, welcome to Jelly Kai, Unit A9, a 2 bedroom 2 bathroom beachfront condo located at Kaibo Yacht Club Phase 2. As you step into this recently renovated second-floor condo, you'll immediately feel the tranquil ambiance that the Cayman Kai area is renowned for. The condo's recent and meticulous renovation (Summer 2023) spared no expense, creating a welcoming retreat that will ensure that you and your family feel right at home.

An outdoor dining area is presented under a vibrant teal umbrella, featuring a glass-top table surrounded by several green chairs. The view beyond includes sandy beach and the Caribbean Sea, framed by palm trees and coastal vegetation.

4.94 out of 5 average rating, 154 reviews

Nature's View: Pools of the Kai #2

Discover the peaceful Caribbean paradise of Cayman Kai. This secluded oasis will put you at ease as soon as you walk through the door. Our beach front property features stunning views across the Caribbean Sea to an unspoiled nature reserve. The double story screened in private pool deck can't be beat. Perfect for family holidays or a romantic getaway. Savor heavenly mornings and sundowners on your master bedroom balcony. Stroll down the beach to Kaibo, true barefoot living!

A beachfront gazebo with a thatched roof is surrounded by palm trees, swaying gently in the breeze. The sandy area leads to the calm waters, showcasing the serene atmosphere of the property. A portion of the building is visible to the right.

5 out of 5 average rating, 32 reviews

Beachfront Kaibo Condo

** POOL CLOSED for repairs until Dec 22nd** Relax with the whole family at this peaceful place to stay. Spend lazy days under the coconut palms or lounging in a hammock in the shade under the beachfront gazebo. Kaibo Brisote is just a short walk to Cayman's famous Star Fish Point and an even shorter walk down the beach to Kaibo Beach Marina, Restaurant and Bar. The perfect spot for family vacations or just a quiet get away. Come make your Cayman Islands memories with us.

4.89 out of 5 average rating, 61 reviews

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

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

Perfectly located on the tranquil north side of Grand Cayman for those who prefer an almost secluded island retreat. Ocean Paradise offers luxury and relaxation in world-class vacation accommodations and is conveniently located near renowned Stingray City, Rum Point and Kaibo’s restaurants, beaches and water sport activities. Bask on the white sand beach, enjoy the pool, swim and snorkel with a myriad of sea life, or simply lounge in your hammock snoozing away the day.

Apartment in Grand Harbour

A light-filled living area features a comfortable sofa facing a modern coffee table. Floor-to-ceiling curtains frame a set of glass doors that lead to a balcony with a view. A wall-mounted television is positioned beside a console, enhancing the space's contemporary design.

4.87 out of 5 average rating, 105 reviews

Waterfront Sanctuary Cove 2BR King Bd Pool Porch

Enhance your getaway experience in our meticulously clean, spacious, and tranquil retreat. Immerse yourself in serenity, surrounded by picturesque water views and a lush tropical landscape that will effortlessly melt your worries away. Ideally situated, our Sanctuary offers not just a stay, but a rejuvenating escape into nature's embrace. Come find your peace in this beautifully designed space, where every detail is crafted for your ultimate relaxation and enjoyment.

5 out of 5 average rating, 10 reviews

A clear, blue pool is surrounded by lush greenery and palm trees, offering a serene setting. White lounge chairs are arranged along the pool's edge, inviting relaxation. The area is well-maintained, with a staircase leading into the water and a gentle slope for easy access.

Flat in Rum Point

The Retreat at Rum Point Beach #19 Cayman Kai

Forget your worries in this spacious and serene space. we're located in the peaceful beauty area known for it privates, Cayman Kai, on the most pristine beach on Grand Cayman. Known for the most beautiful sunrises and sunsets. This complex is well maintained. it has its only private tennis court/Gym . You can swim/dive or snorkel outside of your door. Can rent jet ski and other such items next door. Also great food next door. One of the safest place on earth.

Guest suite in George Town

A tranquil swimming pool is framed by palm trees and a rocky outcrop, with clear blue water inviting relaxation. The ocean is visible in the background, where waves gently meet the shore. Lounge chairs are arranged around the pool area, creating a serene atmosphere.

4.98 out of 5 average rating, 262 reviews

Paradise Escape-Charming Oceanfront Guest Suite

A tranquil oceanfront escape for couples and solo adventurers... Wake-up in bed to a lovely view of a luscious green landscape that melds with the emerald green and blue ocean, sip a hot cup of coffee on the porch, enjoy a sunset cocktail by the ocean front pool, break a sweat in a friendly game of tennis, or take a blanket out to the lawn under the palm trees for breathtaking star gazing. PLEASE NOTE: WE ARE NOT LOCATED ON BATS CAVE BEACH. AIRBNB HAS THIS WRONG!

Popular amenities for Rum Point rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

5 out of 5 average rating, 28 reviews

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

Oceanfront Oasis Home with cottage & private pool

5 out of 5 average rating, 7 reviews

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

Gorgeous 3 Bed Brand New by 7 Mile Beach

5 out of 5 average rating, 62 reviews

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

Casa Avi - Grand Cayman Serenity

4.97 out of 5 average rating, 75 reviews

A clear view of a private pool surrounded by a spacious deck is presented, with the ocean visible in the background. Palm trees sway gently in the breeze, and shaded seating areas are positioned nearby, enhancing the serene atmosphere of this beachfront location.

Home in Grand Cayman

BeachPlumVilla

Home in West Bay Road, George Town

A screened-in patio encases a large swimming pool, reflecting clear blue water and surrounded by lush greenery. Two vibrant red lounge chairs are positioned near the pool's edge, offering a comfortable spot to relax while enjoying the tropical landscape.

5 out of 5 average rating, 26 reviews

Island Oasis

4.96 out of 5 average rating, 51 reviews

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

Oceanfront Dreamsicle Villa w/Outdoor Living Area

4.97 out of 5 average rating, 31 reviews

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

Seabreezes-Your Oceanside Escape

5 out of 5 average rating, 17 reviews

A clear, inviting pool glistens under the sun, surrounded by a spacious patio. Lush tropical landscaping and palm trees add greenery to the backdrop, while the home features large windows reflecting the serene outdoor space.

Home in George Town

Sandalwood Escape Luxury Family Villa Private Pool

Apartment rentals with a pool

5 out of 5 average rating, 85 reviews

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.

Apartment in West Bay

Oceanfront: 2 pools, diving & snorkeling on-site

Apartment in Grand Cayman

A bright living area features a spacious sectional sofa and a modern coffee table. An accent wall with a colorful mural adds visual interest. Natural light filters through large sliding doors, which lead to a balcony adorned with stylish outdoor seating.

5 out of 5 average rating, 11 reviews

The Grove Residences 2Bed/2Bath Apartment

4.87 out of 5 average rating, 167 reviews

An aerial view showcases the resort's layout, featuring a large pool surrounded by lush greenery and palm trees. The pool's inviting shape contrasts with the sandy beach that gently meets the turquoise water. Loungers and umbrellas are positioned along the beach for relaxation.

Apartment in George Town

Grandview condominium directly on 7-mile beach

4.91 out of 5 average rating, 56 reviews

A serene beachfront scene is captured, featuring palm trees swaying gently in the breeze. A sandy shore leads to a calm turquoise ocean, with a wooden dock extending into the water. A manicured pathway runs alongside the beach, bordered by a low stone wall.

Apartment in West Bay

Bougainvillea at Pappagallo Beach Villas (condo#2)

Superhost

A clear blue swimming pool is surrounded by a well-maintained patio area. Two lounge chairs are positioned beside the pool, with lush greenery in the background. Bright, sunny skies and a modern building can be seen beyond the pool area.

Apartment in George Town

4.84 out of 5 average rating, 134 reviews

Cozy Condo near Seven Mile Beach!

Superhost

An aerial view captures the beachfront resort, characterized by multiple low-rise buildings surrounded by lush greenery. The sandy beach meets the turquoise lagoon, with a rocky jetty extending into the water. Lounge chairs are positioned by the pool area, inviting relaxation.

Apartment in George Town

4.85 out of 5 average rating, 178 reviews

Beautiful Modern Condo on 7 Mile Beach

Apartment in Seven Mile Beach

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.

5 out of 5 average rating, 29 reviews

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

4.96 out of 5 average rating, 93 reviews

A spacious screened-in porch features comfortable seating and a dining area, with large windows that provide unobstructed views of the beach and ocean. Tropical palm trees are visible outside, enhancing the serene coastal atmosphere.

Apartment in Savannah

Beachfront walkout with amazing patio & view

Other holiday rentals with a pool

4.94 out of 5 average rating, 35 reviews

A modern living area features a teal sofa and a circular wooden coffee table. A light rug with a minimal pattern lies beneath. The space opens to a dining area with a sleek table and chairs. Warm light is provided by stylish ceiling fixtures.

Flat in George Town

Seaside Serenity at Allure

Guest house in Cayman Islands

A serene outdoor space is showcased, featuring two lounge chairs oriented towards a tranquil canal. Lush greenery and palm trees frame the area, enhancing the view of the water. A well-maintained garden includes potted plants, contributing to a relaxing atmosphere.

5 out of 5 average rating, 56 reviews

Tua'r Mor (near the sea) quiet waterfront escape.

A dining area is featured on a spacious screened-in balcony, showcasing a glass table surrounded by comfortable chairs. Brightly colored towels are draped over the chairs, and a bowl of fresh fruit sits at the center, with stunning views of the turquoise waters and palm trees in the background.

4.88 out of 5 average rating, 8 reviews

The Retreat # 30 Beachfront Oasis at Rum Point

5 out of 5 average rating, 31 reviews

A modern kitchen features white cabinetry and a spacious island with a light-colored countertop. Comfortable bar stools are positioned around the island. Large windows enhance natural light, revealing views of the beachfront balcony. A stylish living area is visible in the background.

Flat in Savannah

Beachfront on Spotts Beach!

5 out of 5 average rating, 12 reviews

A modern living area is showcased with a large sectional sofa accented by light blue and beige pillows. A plush rug anchors the space, while natural light pours in through sliding glass doors that lead to a private balcony with greenery.

Flat in Bodden Town

Moonbay dream

4.87 out of 5 average rating, 92 reviews

A modern living space features a light-colored sofa adorned with decorative pillows and a cozy blanket. A wooden coffee table is placed on a textured area rug, surrounded by greenery from a tall indoor plant. Large glass doors lead to a balcony, allowing in natural light.

Flat in West Bay

New, Luxury 1 Bed/ 1 Bath At 7 Mile Beach

4.96 out of 5 average rating, 25 reviews

A tranquil beach scene features soft sand and clear turquoise waters. Palm trees frame the area, with a wooden pier extending into the sea. A signpost indicating various destinations stands nearby, while a lounge chair invites relaxation under the sun.

Home in GRAND CAYMAN

Beach House at Rum Point/3 Kayaks/4 bikes/WI-FI