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

Epic 3BR - all Ensuite, On-site Diving, Pool/Spa
Welcome to Coconut Bay #126 — a stunning 2,333 sq ft oceanfront townhome in Grand Cayman's quiet North West Point. This end-unit, 3-bedroom, 3.5-bath retreat offers unbeatable access to world-class shore diving, incredible sea views, and island adventures. Dive straight into the Caribbean from your private ladder, relax by two community pools, or stroll to Macabuca, one of the island’s favorite tiki bars. Perfect for families, groups, or dive enthusiasts looking for comfort, style, and location.

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!

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.

Modern Penthouse Oceanfront 1 Bdr Condo /w Pool
Welcome to this stunning, newly built oceanfront condo that boasts breathtaking and uninterrupted views of the sea from the living room, kitchen, and bedroom. Whether you choose to admire the scenery from the stylish and modern interior or step outside onto the expansive patio area, you'll be captivated by the beauty that surrounds you. This spacious one-bedroom, one-bathroom condo featuring sleek and modern accents and furnishings offers ample comfort and convenience for your stay.

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.

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!

Sunset Point Oceanfront Luxury
Bask in panoramic Caribbean views from this brand-new 3-bedroom, 3-bathroom waterfront condo in Grand Cayman. This luxury retreat blends modern design with effortless island living. Floor-to-ceiling glass doors open onto a 35-foot oceanfront balcony, blurring the lines between indoors and out. Whether you’re sipping morning coffee listening to the waves or toasting with sunset cocktails on the terrace, this condo promises a clean, inviting, and luxurious Caribbean escape.

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 West Bay rentals with a pool
House rentals with a pool

Beachfront Retreat w/ Pool – Rum Point Paradise

Gorgeous 3 Bed Brand New by 7 Mile Beach

Oceanfront Oasis Home with cottage & private pool

3 Bedroom Beach House with Pools

Luxury Beachview Retreat, Cayman Island.

Island Oasis

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

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

Oceanfront rooftop luxury2B2B Residency pool beach

The Grove Residences 2Bed/2Bath Apartment

SeaDreams #1 by Grand Cayman Villas

Beautiful Modern Condo on 7 Mile Beach

Cayman Reef Resort 1 - Beach Haven

2 BR beach condo resort with pool and ocean views

"Mai Kai" Recently renovated Oceanfront Condo

Beautiful oceanfront condo in peaceful North Side
Other holiday rentals with a pool

Yippee Kai Yay Beachfront oasis

Classy Studio with pool, near beach!

Luxury 1 bed apt near Seven Mile Beach, The Grove

Spectacular Beachfront! Discovery Point Club #42

Look No Further! Outdoor Pool and Pets Allowed

Beachfront walkout with amazing patio & view

New Oversize Luxury 1 Bd |Turtle Center |Macabuca

Scenic & Stylish Gardenview 3BR Condo wPool Access
Quick stats about holiday rentals with a pool in West Bay
Total holiday rentals
Explore 150 holiday rentals in West Bay
Nightly prices starting at
West Bay holiday rentals start at $108 AUD per night before taxes and fees
Verified guest reviews
Over 2,530 verified reviews to help you choose
Family-friendly holiday rentals
90 properties offer extra space and kid-friendly amenities
Pet-friendly accommodation
Find 10 rentals that welcome pets
Rentals with dedicated workspaces
70 properties have a dedicated workspace
Wi-Fi availability
150 of West Bay holiday rentals include Wi-Fi access
Popular amenities for guests
Guests love Kitchen, Wi-Fi and Pool across West Bay rentals
4.9 Average rating
West Bay stays are highly rated by guests—averaging 4.9 out of 5!
Destinations to explore
- Havana Holiday rentals
- Varadero Holiday rentals
- Montego Bay Holiday rentals
- Ocho Rios Holiday rentals
- Trinidad Holiday rentals
- Negril Holiday rentals
- Viñales Holiday rentals
- Playa de Guanabo Holiday rentals
- Mandeville Holiday rentals
- Treasure Beach Holiday rentals
- Discovery Bay Holiday rentals
- Old Harbour Holiday rentals
- Rentals with outdoor seating West Bay
- Rentals with a patio West Bay
- Apartment rentals West Bay
- Villa rentals West Bay
- Rentals with beach access West Bay
- Rentals with a hot tub West Bay
- Pet-friendly rentals West Bay
- Family-friendly rentals West Bay
- Condo rentals West Bay
- Beachfront rentals West Bay
- House rentals West Bay
- Waterfront rentals West Bay
- Fitness-friendly rentals West Bay
- Rentals with a washing machine and dryer West Bay
- Luxury rentals West Bay
- Rentals with pools West Bay
- Rentals with pools Cayman Islands