Holiday rentals with a pool in George Town

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

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!

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

This family friendly condo is close to restaurants and dining, the beach, family-friendly activities, nightlife, and public transport. You’ll love this place because of the location, the people, the ambiance, the outdoors space, and the neighborhood. My place is good for couples, solo adventurers, business travelers as well as families with children. The property has biggest pool on Seven Mile Beach and hot tub overlooking beach with best sunsets. It also offers tennis courts and Basketball.

A modern living area features large windows offering expansive ocean views. A light-colored sectional sofa is paired with a round woven coffee table, while a neutral rug anchors the space. A wooden sideboard and stylish armchair complement the airy atmosphere.

5 out of 5 average rating, 21 reviews

3-Bedroom Condo with ocean view

Experience luxury at its best with this beautiful new condo on Seven Mile. Featuring stunning ocean views, sunsets, spacious living spaces. This charming property features 3 bedrooms with 1 king bed and 2 queen beds, perfect for a group of friends or family, living areas with large windows to take in the natural beauty of the Caribbean. Amenities include a swimming pool, hot tub, fitness center, parking, rooftop lounge. Ideal for vacation or year-round living. Book your dream vacation today!

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.

4.84 out of 5 average rating, 134 reviews

Cozy Condo near Seven Mile Beach!

Welcome to the Cozy Condo, the spot for everyone coming to Grand Cayman for work, play, or a little bit of both—all at a budget-friendly price! You’ll love our prime location, just minutes from the George Town, the lively Camana Bay, and the beautiful Seven Mile Beach. Plus, you’ll find two convenient supermarkets and pharmacy within easy walking distance or a quick drive which has everything you could want, from shopping and dining to entertainment and drinks. We can’t wait to to host you!

5 out of 5 average rating, 5 reviews

Flat in West Bay

Oceanfront Sunset Patio w/ BBQ + Pool, Gym & Spa

Welcome to Sunset Point #29 — a brand-new 1-bedroom, 1.5-bath oceanfront condo in Grand Cayman’s quiet North West Point. This 1,016 sq ft ground-floor retreat features floor-to-ceiling windows, a private patio with Weber grill, and the island’s best sunset views. Relax by the oversized pool and spa, work out in the fully equipped gym, or stroll 2 minutes to Macabuca for world-class diving, cocktails, and Cayman sunsets. Perfect for couples or small families seeking style and serenity.

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.

4.94 out of 5 average rating, 34 reviews

Seaside Serenity at Allure

Affectionately dubbed the Seaside Chateau by owner and local fragrance designer Ted Green, Seaside Serenity at Allure is less Chateau and more contemporary island retreat that just happens to be nestled at the sea's edge of the North Sound (Caribbean Sea). A perfectly appointed and centrally located retreat. You will feel nestled away from it all, but in actuality, you're no farther than 5-10 mins from your favorite spots in South Sound, George Town, or Seven Mile Beach.

A view of a sandy beach along the ocean with gentle waves lapping at the shore. People can be seen enjoying the water and walking along the beach. A rocky barrier is visible in the distance, complementing the vibrant blue sky and fluffy clouds above.

5 out of 5 average rating, 15 reviews

Beachfront - Sunset Cove Resort

Enjoy our new unit at special reduced prices which offers lounging on 7 Mile Beach or relaxing at the largest pool on island, complete with a swim-up bar, whirlpool, and a shallow wading pool for children. Dine at the Lazy Lizard Restaurant on site, serving delicious meals and refreshing drinks. This oceanfront unit features a private patio. Relax by the pool, snorkel, explore the reef, or unwind in your luxurious, resort-style condo for an unforgettable vacation.

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!

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.

4.85 out of 5 average rating, 178 reviews

Beautiful Modern Condo on 7 Mile Beach

Welcome to our beautiful second floor condo on the world renowned Seven Mile Beach. Sunset Cove is a beachfront resort minutes from George Town. It has a stunning beach lagoon and amazing pool with a kiddies pool, hot tub and swim-up bar. Our “beach chic” condo has just been fully renovated. We stripped it back to the bare concrete floor and walls and everything is brand new. We hope you like it and look forward to welcoming you to our little island paradise!

An aerial view showcases the oceanfront complex surrounded by lush greenery and a spacious lawn. A sparkling pool is centered among the buildings, with lounge chairs arranged nearby. The turquoise waters and sandy beach are visible, highlighting the inviting coastal location.

5 out of 5 average rating, 23 reviews

Luxury Ocean View Oasis on 7 Mile Beach

This luxury oceanfront apartment sits on Seven Mile Beach, within a 4-acre complex offering a spacious vacation oasis. Walk to nearby restaurants, shops, and amenities. Steps away, snorkel in turquoise waters teeming with vibrant sea life. Complex features: - Ocean-view pool - Outdoor BBQ area - Lit tennis/pickleball court - Playground Experience Cayman's beauty, tranquility, and adventure from this luxurious oceanfront retreat. Book now!

Popular amenities for George Town rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

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

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

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

4.88 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

5 out of 5 average rating, 8 reviews

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

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

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

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

An aerial view showcases the resort's lush, landscaped grounds, featuring a large swimming pool surrounded by sun loungers and umbrellas. The turquoise ocean and sandy beach are visible in the background, highlighting the property's beachfront location. Palm trees add to the tropical ambiance.

4.97 out of 5 average rating, 36 reviews

Be where the cruise ship crowds cannot go!

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 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.

5 out of 5 average rating, 48 reviews

Fall Into Paradise Sale-Regal Beach 233 Seven Mile

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

5 out of 5 average rating, 9 reviews

A clear view showcases a tranquil pool with in-water bar stools, framed by swaying palm trees. The ocean stretches beyond the sandy beach, with gentle waves lapping at the shore. Bright blue skies and vibrant hues of teal and turquoise enhance the coastal scene.

Apartment in Bodden Town

Magnificent Ocean Front Sea Palm Villa #11

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!

4.94 out of 5 average rating, 98 reviews

Access to a private beach is visible through a white gate, framed by lush green shrubs and sandy paths. The ocean stretches out to the horizon, reflecting clear blue skies and soft clouds, inviting a serene coastal experience.

Apartment

Oceanfront 2bed 2bath Condo Seven Mile Beach

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.

4.81 out of 5 average rating, 27 reviews

The living area features a comfortable blue sofa with decorative pillows, paired with a glass coffee table atop a patterned rug. A functional kitchen is visible, equipped with modern appliances, including a refrigerator and a washer-dryer. Natural light enters through nearby windows.

Flat in Grand Harbour

Elegant One-Bedroom Apartment in Grand Harbour

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

4.88 out of 5 average rating, 91 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

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

Luxury 1 bed apt near Seven Mile Beach, The Grove

Superhost

A modern living area features large glass sliding doors that open to a balcony, allowing natural light to fill the space. A sectional sofa is arranged around a low coffee table, with a textured area rug beneath. A plant adds a touch of greenery to the room.

Flat in Seven Mile Beach Corridor

5 out of 5 average rating, 4 reviews

ONE Canal Point - 2 Bedroom Deluxe Family Condo

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.