Family-friendly holiday rentals in Rum Point

4.99 out of 5 average rating, 412 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

Indoor spacesFamilyGetting around

4.99 out of 5 average rating, 117 reviews

Home in North Side

North Side Grand Cayman Beachfront Villa

Spacious beachfront home on Grand Cayman’s peaceful North Side. Walk out to crystal-clear water for snorkeling and paddleboarding — we provide kayaks, paddleboards, and snorkel gear. 4 en-suite bedrooms plus two sofa beds in living room, rooftop with ocean views, fast WiFi, full kitchen, and washer/dryer. Small grocery store and Over the Edge are 1 mile away. Supermarket in Savannah (~20 min). Restaurants & bars @ Kaibo & Rum Point (~15 min). Travel crib and kids’ games available. Self check-in.

KitchenIndoor spacesView

A private pool is framed by a wooden deck, offering views of the Caribbean Ocean. Bright blue lounge chairs are positioned nearby, alongside palm trees swaying in the gentle breeze. The turquoise water of the ocean contrasts with the sandy beach in the background.

5.0 out of 5 average rating, 19 reviews

No Big Ting - Private Beach Home

Entering No Big Ting you're immediately greeted with stunning views of the beautiful Caribbean Ocean. It's all about outdoor living, from the spacious screened porch to the soft sandy beach. Cool off in the private pool or adventure out to the protected reef to snorkel with the abundant sea life. End a perfect day star gazing on the deck listening to the waves under the moonlight. No Big Ting delivers a tranquil ocean vibe and is the ultimate beachfront oasis to relax with family and friends.

Indoor spacesKitchenDecor

4.93 out of 5 average rating, 231 reviews

A screened-in patio features a colorful area rug and seating arrangement with patterned cushions. A ceiling fan is visible above, while views of the lush garden and cove are framed by large glass panels. Kayaks and lounge chairs are positioned outside, enhancing the outdoor atmosphere.

Apartment in Cayman Kai

Rum Cove on the Bioluminescent Bay with Ocean View

Welcome to Rum Cove – your private escape on the bioluminescent bay, just steps from the world-famous Rum Point. This bright & breezy 1-bedroom retreat is part of a charming triplex and offers stunning 360° views. Whether you’re relaxing on the patio, kayaking under the stars, or sipping coffee at sunrise, Rum Cove surrounds you with natural beauty & peace. A perfect space for couples, solo travelers or small families looking for a quiet getaway with the best of Cayman Kai on your doorstep.

KitchenIndoor spacesBeach

4.98 out of 5 average rating, 124 reviews

Cottage in East End

Hidden Gem Cottage on the Beach

Hidden Gem is a Traditional Cayman Style cottage located at Grapetree Cove on a beautiful beach area in sleepy fishing village of East End. The property is filled with trees that gives it a dreamy Island ambiance. The Cottage has been fully renovated with modern amenities that makes is very comfortable and homey. Hidden Gem offers a unique CaymanKind experience from a Caymanian host that knows the area well. Located minutes away from local dinning places and many key attractions in the area.

KitchenFamilyLong stay

4.99 out of 5 average rating, 138 reviews

The entrance features a dark front door framed by two windows with black shutters. Potted plants are positioned on either side of the door, adding greenery to the wooden facade. The porch is supported by two white columns, creating a welcoming appearance.

Apartment in Savannah

Enoe’s Escape

Welcoming 1 bedroom apartment with en-suite bathroom, sitting area, full kitchen, washer, dryer, and outdoor patio. Located in a quiet neighbourhood in close proximity to most things. 2-minute walk to the historic site Pedro St. James Castle, a stunning spot to view sunsets! 3-minute drive from the nearest supermarket and local restaurants. 5-minute drive to the picturesque Spotts Beach. 20-minute drive from other popular destinations, including shopping centres and other local attractions.

Indoor spacesKitchenBeach

4.95 out of 5 average rating, 39 reviews

Whispering Kai: beach home on Bio Bay, Cayman Kai

A quiet oasis with unforgettable views. Located directly on the Bioilluminesce Bay in the wonderful residential area of Cayman Kai is our luxurious yet comfortable 2 bedroom, 2 bathroom secluded beachfront home complete with a spacious screened-in back patio overlooking the water on a white sandy beach with a private boat dock. Check us out on Insta: @whisperingkai Master Bedroom: King Bed Guest Bedroom: King Bed plus two pull-out sofas (twins) Living Room: One pull-out sofa (double)

Indoor spacesKitchenCheckout

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, 171 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!

FamilyKitchenQuiet

4.94 out of 5 average rating, 109 reviews

An outdoor terrace features comfortable wicker seating, complemented by colorful cushions. Lush palm trees frame the view of the tranquil turquoise waters and clear sky, enhancing the inviting coastal atmosphere.

Home in George Town

Paradise Beach House in South Sound, George Town

Paradise Beach House in South Sound, George Town Paradise Beach House is a beautiful vacation rental property located in South Sound, George Town, Grand Cayman. The house offers a spacious and luxurious living experience with its very own paradise beach and a view of the reef and famous wreck of South Sound! Please note the "Resort Fee" is the Government Tourist Tax that is charged to all international guests staying in the Cayman Islands.

FamilyKitchenDecor

5.0 out of 5 average rating, 18 reviews

Waterfront 2BR with private screened pool

Unwind in this renovated waterfront 2BR at Pools of the Kai, featuring a private screened pool and two king suites with water views. The upper suite has a private balcony, while the lower opens directly onto the pool deck. A sofa bed accommodates 2 additional guests. Walk to Kaibo, kayak to Starfish Point or explore Bioluminescent Bay. Fast Wi-Fi and peaceful Cayman Kai surroundings make it ideal for couples, families and groups of up to 6.

Indoor spacesFamilyValue

4.97 out of 5 average rating, 119 reviews

An airy living area is depicted with a spacious couch, a coffee table, and a dining area featuring light-colored chairs. Large windows offer views of palm trees and the beach, while natural light brightens the room, creating a fresh and inviting atmosphere.

Condo

Oceanview 2BR Condo w/ Big Balcony on 7 Mile Beach

Stylish, spacious, and steps from the sea—Cocoplum 10 is a renovated 2-bedroom, 2-bath condo with ocean views, coastal-modern interiors, and a large private balcony overlooking the Pool and Ocean. Located on the quieter end of Seven Mile Beach, you’ll enjoy calm waters for snorkeling and paddleboarding, a beachfront pool, and easy walks to local restaurants and shops. One of the most popular 2BR condos on the island—book early!

Indoor spacesKitchenSleep quality

4.98 out of 5 average rating, 141 reviews

A round dining table is set for four, surrounded by light-colored chairs. The space features large glass windows that offer views of palm trees and neighboring outdoor seating. Natural light illuminates the interior, enhancing the serene setting.

Apartment

Rum Haven villa on Bioluminescent Bay & Ocean view

Welcome to Rum Haven - a 1-bedroom, 1-bath peaceful hideaway perfectly situated on the bioluminescent bay and directly across from the iconic Rum Point Club. This charming unit is ideal for couples seeking a relaxing island getaway. Unwind in the hammock, paddle along the Bio Bay in our complimentary kayak, or simply enjoy the views from your private porch. Maid service is included for stays over 7 nights.

FamilyIndoor spacesQuiet

Popular amenities for Rum Point family-friendly rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.88 out of 5 average rating, 183 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.

Condo in George Town

Grandview condominium directly on 7-mile beach

KitchenIndoor spacesView

4.9 out of 5 average rating, 111 reviews

A spacious living area is furnished with a light grey sectional sofa and a circular coffee table. A large flat-screen television is positioned on a wooden media console. Natural light floods in through glass doors, which lead to a balcony with views of greenery, enhancing the inviting ambience.

Apartment in George Town

2 Bedroom 2 Bathroom Condo 7 Mile Beach

Indoor spacesKitchenWalkability

Guesthouse in Grand Harbour

A vibrant outdoor area surrounds the unit, featuring a patio with a blue umbrella over a black dining table. Lush greenery and flowering plants enhance the space. A seating area offers relaxation options, with decorative stones leading to a grassy area, providing a serene atmosphere.

Heavenly Suite 1 - The M @ the Edge

Indoor spacesFamilyCleanliness

4.99 out of 5 average rating, 152 reviews

4.92 out of 5 average rating, 300 reviews

Condo in Grand Harbour

Waterfront Sanctuary | King Suite | Pool + Porch

Indoor spacesFamilyLayout

4.97 out of 5 average rating, 181 reviews

A spacious living area features a light-colored sectional sofa and a large area rug. Wooden beams line the ceiling, reflecting natural light. A dining table is visible, accompanied by modern lighting fixtures. The open layout connects to the kitchen area, enhancing the inviting ambiance.

Condo

2 BR beach condo resort with pool and ocean views

KitchenFamilyCleanliness

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.

Yippee Kai Yay Beachfront oasis

Indoor spacesFamilyWalkability

4.97 out of 5 average rating, 38 reviews

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.

4.96 out of 5 average rating, 49 reviews

"Mai Kai" Recently renovated Oceanfront Condo

FamilyKitchenTV

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.

5.0 out of 5 average rating, 43 reviews

Beachfront Kaibo Condo

FamilyIndoor spacesDecor

Family- and pet-friendly home rentals

4.94 out of 5 average rating, 186 reviews

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.

Condo in George Town

Seven Mile Beach with Soul

Indoor spacesKitchenQuiet

5.0 out of 5 average rating, 43 reviews

A private swimming pool is set within a tiled outdoor area, surrounded by lounge chairs and tropical plants. The ocean sparkles in the background, with gentle waves under a clear blue sky. A wooden railing marks the edge of the pool area, offering unobstructed sea views.

Home in West Bay

Oceanfront Oasis: Turquoise Views, Pool & Cottage

KitchenFamilyCleanliness

5.0 out of 5 average rating, 37 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

FamilyKitchenCondition

4.97 out of 5 average rating, 58 reviews

The entrance of Savhaven is framed by tropical plants, featuring vibrant foliage. Steps lead up to a set of double doors, highlighted by an arched window above. A decorative wreath hangs on the door, inviting guests into the property.

Home in Savannah

Savhaven - 4 Bed 4 Bath w/ Pool (2 mins to Beach)

KitchenFamilySleep quality

Superhost

Tall palm trees sway gently by a sandy beach, framing a view of the North Sound. The manicured lawn is dotted with smooth stones, and lounge chairs are positioned along the shoreline. A building with balconies overlooks this serene coastal setting.

Condo in Grand Cayman

1BR King Suite w/ Kitchen, Patio & Living Area

Indoor spacesFamilyAmenities

4.78 out of 5 average rating, 65 reviews

4.94 out of 5 average rating, 16 reviews

A modern single-story home is framed by lush palm trees, featuring a white exterior and a welcoming entrance. A gated pathway leads to the front door, while a manicured yard offers an open view, inviting guests to explore the surrounding landscape.

Home in West Bay

West Bay Dream

Indoor spacesKitchenLocation

4.99 out of 5 average rating, 81 reviews

A graphic featuring green leaves creates a natural backdrop for the text 'Nim's Retreat,' which is displayed in a soft blue font. The overall design emphasizes a connection to nature, indicative of the serene environment surrounding the property.

Apartment in George Town

~Nim's Retreat~ Grand Cayman BWI

KitchenIndoor spacesAir conditioning

Apartment in Seven Mile Beach

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.

Steps to Seven Mile Beach | 1-Bed at The Grove

KitchenIndoor spacesAccess

4.99 out of 5 average rating, 77 reviews

Family-friendly home rentals with a pool

Holiday home in Bodden Town

A serene view of the turquoise ocean stretches beyond a well-maintained pool area. Lush palm trees and vibrant greenery frame the space, with a sandy beach visible nearby. The outdoor seating area is partially shaded, creating a relaxing atmosphere for guests.

Art Beach House, boutique style luxury.

FamilyIndoor spacesBathroom

5.0 out of 5 average rating, 114 reviews

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.

Paradise Escape-Charming Oceanfront Guest Suite

Indoor spacesKitchenComfort

4.97 out of 5 average rating, 304 reviews

4.95 out of 5 average rating, 110 reviews

A serene ocean view captures calm turquoise waters meeting the sky, dotted with fluffy white clouds. The image features a rocky shoreline with a concrete dock extending into the water, surrounded by lush greenery and picturesque coastal scenery.

Condo in West Bay

Oceanfront- Restaurant,Diving & Snorkeling on site

FamilyKitchenTV

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, 64 reviews

Beachfront Bliss 7th Night Free @ Rum & Kai

FamilyKitchenComfort

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.

4.98 out of 5 average rating, 60 reviews

Private Beachfront Retreat, Pool/Snorkel, 16 Guest

FamilyKitchenCheckout

4.96 out of 5 average rating, 26 reviews

The exterior of the townhouse showcases a sandy pathway leading to a shared outdoor space. Seating options include colorful lounge chairs arranged under palm trees, with the two-story structure visible in the background. Sunlight illuminates the area, creating a vibrant yet relaxing atmosphere.

Townhouse in Rum Point

Dream Kai Island House #15

KitchenFamilyQuiet

Apartment in Rum Point Beach

A serene beach scene is captured at sunset, showcasing white lounge chairs positioned on soft sand. A glass filled with a beverage rests on a nearby table, while vibrant hues of orange and blue fill the sky and reflect off the calm water.

Caribbean Marine Park Retreat, Beachfront Bliss

FamilyKitchenSleep quality

4.97 out of 5 average rating, 29 reviews