Vacation rentals with a pool in Cayman Islands

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.

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.

Just Chillin in Little Cayman

Just Chillin is a new 2 bedroom house that connects to a semi private pool, with queen size bed in both bedrooms, it is close to the airport, store and restaurants, the true Island life. Little Cayman is One mile wide and 10 miles long, we also provide bikes if you’re adventurous, our waters are blue and crystal clear for the divers and People that like to snorkel, it is Paradise, and tranquility for the people that just want to chill!

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.

2 BR beach condo resort with pool and ocean views

This luxury penthouse condo has everything for your perfect vacation. Enjoy stunning views of the sun setting over the Caribbean Sea from your private balcony. Located in a resort style complex with a great amenities. This includes bike use, large pool with swim up bar, kiddie pool and hot tub. Great snorkeling off our beach.