Holiday rentals with a pool in Rum Point

4.99 out of 5 average rating, 325 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

4.97 out of 5 average rating, 32 reviews

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

Beachfront Retreat w/ Pool – Rum Point Paradise

Sea Charm is a beautiful spacious beachfront house in Rum Point with panoramic sea views and sunrises. The villa can hold multiple families and has a large and pristine beach front with excellent snorkeling outside the doors. Family friendly or romantic vacation at this large beachfront home is great for adventure, fun and relaxation. It’s only a 3-minute walk from Rum Point club with a bar, restaurant and beach with water sports. Starfish Point, Kaibo and Bioluminescence Bay are minutes away.

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.

Apartment in Grand Harbour

A pool area is shown with lounge chairs arranged around a clear blue pool. The deck is paved with light-colored bricks and surrounded by greenery. In the background, a covered seating area with multiple chairs can be seen, alongside colorful buildings under a sunny sky.

4.92 out of 5 average rating, 274 reviews

Waterfront Sanctuary Serene | 2BR | Pool & Porch

Cool clean contemporary Sanctuary with water views; a two bedroom/two bathroom condo with a full kitchen and living room packed with all popular amenities (wifi, cable television, Apple TV, Netflix, Playstation game console, central A/C, iron and ironing board, washer and dryer, outdoor patio, pool and free parking) - conveniently located in Grand Harbour. The Shoppes at Grand Harbour, & Harbour Walk are next door. Perfect for exploring and enjoying all that the Cayman Islands has to offer.

The living area features a comfortable sofa adorned with decorative cushions. A light wooden coffee table sits on a patterned rug, and a wall-mounted TV is positioned across from the seating. Sunlight floods in through the sliding doors that open to a private patio.

4.95 out of 5 average rating, 186 reviews

Cayman Reef Resort on Seven Mile Beach

At the heart of Seven Mile Beach, our home is in the middle of everything and far from nothing. Extensively renovated and well maintained, the condo is designed for you to enjoy a tranquil beach getaway in a luxurious setting with all the comforts of home. Picture perfect views, top of the line amenities and our local touch provide a warm welcome and cozy stay. We are fully licenced and our rate includes the 13% tourist accommodation tax. 20% discount from list price for local residents!

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.

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, 151 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!

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, 258 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!

A beachfront view of a multi-story condo complex is captured, with tropical palm trees swaying in the gentle breeze. The clear waters reflect the blue sky, while sun loungers are visible on the sandy beach, inviting relaxation along the shoreline.

4.98 out of 5 average rating, 49 reviews

Beachfront Bliss 7th Night Free @ Rum & Kai

New to AirBnB, but not new to our guests. Get away from it all at 'Rum and Kai', located at the Retreat in Rum Point. This beach front 1 bedroom condo is located in the stunning upscale vacation home enclave of Cayman Kai on beautiful Grand Cayman. The unit is tastefully decorated with high-end furnishings and the finest linens; all in an understated, yet elegant tropical West Indies motif. Private beach with world class snorkeling right off the shore.

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, 27 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, 60 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, 74 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

5 out of 5 average rating, 3 reviews

Home in Rum Point

Fantasea by Grand Cayman Villas

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

4.88 out of 5 average rating, 95 reviews

The exterior view of the Cream home showcases a two-story structure with a white metal roof and light beige walls. A balcony is visible above, featuring seating, while a spacious patio below contains outdoor furniture and a hammock surrounded by lush greenery.

Home in North Side

Luxury 3bd Ocean View, # 1 Cream, Stunning Views

Apartment rentals with a pool

5 out of 5 average rating, 84 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

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.

4.88 out of 5 average rating, 165 reviews

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)

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.

4.84 out of 5 average rating, 134 reviews

Cozy Condo near Seven Mile Beach!

A screened patio area is visible, featuring a blue dining table surrounded by six white chairs. Colorful cushions in vibrant patterns are placed on the long seating along the back. Lush greenery can be seen through the patio screens, creating a tropical atmosphere.

4.93 out of 5 average rating, 164 reviews

Seven Mile Beach with Soul

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.

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!

Other holiday rentals with a pool

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.

5 out of 5 average rating, 30 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

4.96 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

5 out of 5 average rating, 58 reviews

A bright living area features modern furnishings, including a spacious sofa and a cozy armchair. Natural light floods through a floor-to-ceiling sliding door, leading to a private balcony. Textured area rugs enhance the space, complementing the neutral color palette.

Flat in Seven Mile Beach

Luxury 1 bed apt near Seven Mile Beach, The Grove

5 out of 5 average rating, 19 reviews

An outdoor dining area is presented on a shaded balcony, featuring a large white table set with placemats, cutlery, and a small potted plant. Lush green grass, tropical plants, and the ocean are visible in the background, with a cruise ship framed by palm trees.

Flat in George Town

Oceanfront Condo on Seven Mile Beach

5 out of 5 average rating, 4 reviews

A scenic beachfront view captures the soft sandy shoreline meeting the turquoise sea. Five people are engaged in various beach activities under a partly cloudy sky. The condo’s exterior features large glass windows, offering expansive views of the ocean and beach from the patio area.

Flat in Grand Cayman

Beachfront View on 7 Mile Beach