Holiday rentals with a pool in Cayman Islands

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Cayman Islands

Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

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Guest favourite

Cottage

4.98 out of 5 average rating, 238 reviews

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

Guest favourite

Holiday home

4.93 out of 5 average rating, 60 reviews

Ground Suite 2b2b Ocean Side in 7 Mile w/ Pools

Experience a resort nestled in quiet area at the start of Cayman's famous Seven Mile. Walking distance to water, bars, beach and restaurants. Great for two or three singles, two couples or a family with 2 bedrooms with ensuite bathrooms and on-site pools and minimalistic beach. Centrally AC’ed 2-bedroom & 2-ensuite bathroom villa with a fully equipped kitchen, private screened patio, with WiFi 100Mbps. On bus route. Choice of two pools, tennis court, BBQ, SUPs, kayaks, and beachfront access.

Guest favourite

Home

5 out of 5 average rating, 16 reviews

Oceanfront Oasis Home with cottage & pool

Relax in paradise with the family at this peaceful home in Spanish Bay. With miles of incredible cresting waves and turquoise ocean, this is a tranquil and secluded property. The main home has 3 bedrooms & 3 bathrooms and the adjoining cottage is equipped with a bed, bathroom & kitchenette. On calm days, you can swim off the end of the garden into the sea, or swim in your private swimming pool with plenty of outdoor space for entertaining. 25 minutes to the airport; 10 minutes to 7 mile beach.

Guest favourite

Flat

5 out of 5 average rating, 30 reviews

NEW! Modern Beach/Oceanfront Condo - WOW!

PARADISE is what you will find when you enter Villa #5. This 2-story condo is located on the beach with the most incredible views of Cayman’s crystal blue water. The entire unit has been meticulously renovated by an award-winning design firm, complete with high-end finishes and furnishings. This will have you feeling like you are staying at a five-star resort, but at a fraction of the price. It is a true oasis, with all the luxuries and amenities of home. People from all backgrounds welcome!

Guest favourite

Home

4.94 out of 5 average rating, 16 reviews

POOL, sandy beach w/cabana, wi-fi, a/c, sunsets

Truly Amazing Tropical Beach Paradise on the Water w/Pool. Prop has private entrances, full kitchen (with everything), dining, living, full bathroom, beach cabana, hammocks, bikes available, grill, kayaks, fire pit. WiFi. Great snorkeling right out front. Great sunsets! One of the few rental places on the island with a sandy beach. Leeward side of the island so many days with calm waters. Local cell phone provided. Washer and Dryer, TV, Linens, beach and bath towels & more. 1 of only 3 units.

Superhost

Apartment

5 out of 5 average rating, 3 reviews

Dreamy Ocean Front Sea Palm Villa #10

Oceanfront Caribbean Style Villa that is centrally located in Bodden Town for a laid-back experience in tranquility. All 12 villas in complex are oceanfront with views of the sea. We have 6 villas on main floor and 6 villas on second floor. You can enjoy the pool with in-water bar stools or sit on a private beach near the ocean. We have a stretch of beach that allows you to walk for miles. We are surrounded by a coral reef giving our guests access to some of the best snorkeling on the island.

Guest favourite

Apartment

4.93 out of 5 average rating, 125 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!

Guest favourite

Home

5 out of 5 average rating, 8 reviews

Beautiful 4 BR/3 BA South Sound Home w/pool.

Beautiful 4 Bedroom Home w/pool. Close to Beach, George Town, Park, Tourist Center Step away from the busy resort area! This 4 BR home is located in a quiet area in South Sound. and perfect for your family's vacation. Enjoy a fun filled at the beach and relax by the pool later in the day. This home has 4 BR, 3 BA and sleeps 8-10. Full kitchen/outdoor grill. A screened porch and spacious veranda overlooking the pool is a perfect spot for breakfast or evening dinners.

Guest favourite

Flat

5 out of 5 average rating, 12 reviews

Resort Make 2br/2ba Condo on SMB

This newly renovated condo is centrally located on Seven Mile Beach and will provide you with the ultimate family getaway. You will be steps away from the pool, kiddie pool, hot tub, swim up restaurant/bar and best of all, beach. Located at the pool and beach are chairs and umbrellas, exclusively for Sunset Cove guests. Grocery stores, restaurants, and other stores are a short walk away. Enjoy the beautiful garden view from the patio, and experience a true tropical paradise.

Superhost

Home

4.86 out of 5 average rating, 7 reviews

Entire Home on SMB Corridor - Family friendly

Luxurious, spacious home in the heart of Cayman, nestled in a private, serene neighbourhood, perfect for families and friends. Explore the stunning Seven Mile Beach just a 10 to 15 minute walk away and enjoy modern comforts including a fully equipped kitchen, air conditioning, & high-speed Wi-Fi. Preferred max. # of guests 7: 4 adults and 3 children One extra guest can be accommodated for a fee. Includes Ring Video door bell at front door entrance

Guest favourite

Home

5 out of 5 average rating, 20 reviews

Seabreezes-Your Oceanside Escape

Kick back and relax in this calm, stylish loft situated in an oceanfront community- a perfect Caribbean get away for a short break or longer holiday. The central location allows for easy access by car to all the areas of this lovely holiday Island. The property offers open spaces, 5 pools, an oceanfront walkway and a Cabana. Step outside to enjoy a morning swim in the pool; a glass of wine on the porch, or a romantic evening stroll by the boardwalk.

Guest favourite

Home

4.9 out of 5 average rating, 10 reviews

Casa de Bells Deluxe

You'll have a great time at this comfortable place to stay. Peaceful, family-friendly, and private with all the amenities that you need. Relax after a day at the beach or touring the beautiful island in the luxurious pool. With this deluxe booking, no other guest will be on the property therefore you will have exclusive access to the pool, gazebo, and all outdoor spaces.