
Holiday rentals with a pool in George Town
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in George Town
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

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

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!

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.

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!

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!

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!

Paradise Escape-Charming Oceanfront Guest Suite
A tranquil oceanfront escape for couples and solo adventurers... Ours is a unique community with quaint freehold condo cottages on a vast tract of oceanfront land. 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.

Coastal Hideaway
This charming 1-bedroom retreat is in a convenient neighborhood, minutes from beaches, restaurants, and attractions. Bright and inviting, it features a comfy queen bed, a beautifully decorated living area, and a fully-equipped kitchen. Enjoy your private patio for morning coffee or an evening drink, plus a shared pool and lush gardens. With Wi-Fi, TV streaming, and air conditioning, it’s all set for a comfortable stay. Perfect for exploring and unwinding in the Cayman Islands.

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.

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!

Beachfront 2BR Seven Mile | Beach, Pool & BBQ
Wake up to sweeping ocean views in this 2BR Seven Mile Beach apartment. Enjoy sea views from the balcony and master bedroom, with snorkeling just steps away. With beach access, pool, and BBQ area, the complex offers both relaxation and adventure. Walk to shops, dining, and Camana Bay, then return to your private retreat—perfect for families, couples, or friends.

Island Pine Villa Ocean View
Watch beautiful sunsets every night from the balcony, overlooking ocean, or take a short walk to Camana Bay center with lots of restaurants, cinema, great happy hours and lots of room for children to run around! And of course large supermarket Foster's with all your needs is located at short walking distance at Caymana Bay as well.
Popular amenities for George Town rentals with a pool
House rentals with a pool

Beachfront Retreat w/ Pool – Rum Point Paradise

Parrot-ise 4 Bedroom Oceanfront Villa in Cayman Ka

Oceanfront Oasis Home with cottage & private pool

Gorgeous 3 Bed Brand New by 7 Mile Beach

Luxury Beachview Retreat, Cayman Island.

Island Oasis

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

Hidden Hideaway House -7 mile -2King/1Queen- Pool
Apartment rentals with a pool

Oceanfront: 2 pools, diving & snorkeling on-site

Enjoy Sunsets at Cayman Reef Resort - 7 Mile Beach

Seven Mile Beach-2nd Floor BeachView at SunsetCove

Fall Into Paradise Sale-Regal Beach 233 Seven Mile

Resort Style 2br/2ba Condo on Seven Mile Beach

Sunset Cove Condo on Seven Mile Beach - 2bed/2bath

Modern 7Mile Beach Condo - Heated Pool-Pickleball

Cayman Reef Resort 1 - Beach Haven
Other holiday rentals with a pool

Art Beach House, boutique style luxury.

West Bay Oasis: 2BR Condo w/Pool

Where Retreat

Luxury 1 bed apt near Seven Mile Beach, The Grove

Beach front condo, Seven Mile Beach Cayman Islands

Ocean Club Oasis

Beachfront walkout with amazing patio & view

Resort style condo steps away from the beach
Quick stats about holiday rentals with a pool in George Town

Total holiday rentals
Explore 180 holiday rentals in George Town

Nightly prices starting at
George Town holiday rentals start at $65 SGD per night before taxes and fees

Verified guest reviews
Over 4,540 verified reviews to help you choose

Family-friendly holiday rentals
150 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
90 properties have a dedicated workspace

Wifi availability
180 of George Town holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across George Town rentals

4.9 Average rating
George Town stays are highly rated by guests – averaging 4.9 out of 5!
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