Vacation rentals with a pool in Water Island

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Water Island

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

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Guest favorite

Home in NorthSide

5 out of 5 average rating, 28 reviews

Heated Pool, OceanView, Generator, Local Discounts

Welcome to Sunrise Villas by Stacie! Enjoy island living at our newly constructed home offering breathtaking ocean/island views. Enjoy the heated pool with baja sun deck, bubblers/jets/lights. Relax in our spacious indoor/outdoor space with 20 foot sliding door, huge kitchen, bar, and fireplaces. No worries about island power with our whole home generator. Perfect escape for families with older children, couples, or a group of friends - book with our home right next door for up to 6 more guests!

Guest favorite

Villa in Southside

4.96 out of 5 average rating, 56 reviews

Frenchman's View Villa 2 BD/2.5 BA w/ Pool

NEW LISTING! Breathtaking sunset and ocean views from this gorgeous villa nestled among the trees in paradise. A generous living space with oversized sectional effortlessly flows into the outdoor patio and pool area, perfect for sunbathing, a BBQ with friends and family, or a cocktail under the shaded cabana area. 2 fully air-conditioned bedrooms and 2.5 baths round out this fabulous property! Minutes to Havensight, Yacht Haven Grande, Charlotte Amalie, and a variety of shops and restaurants!

Guest favorite

Home in Southside

4.95 out of 5 average rating, 101 reviews

Sunset Terrace – Perfect home for your vacation!

Sunset Terrace Villa offers a private and accommodating home for your Caribbean vacation! This fully air-conditioned home offers a private pool, new renovations, furnishing and spectacular views of the water and surrounding islands. Beautiful sunsets are an everyday experience and can be enjoyed inside or from the covered, outdoor patio space. Centrally-located in a safe and scenic neighborhood. Nearest beach is only a 5 minute drive. Concierge service included. Designed by Ashley-Interiors

Guest favorite

Villa in Water Island

4.92 out of 5 average rating, 36 reviews

5 Star LUXE VACAY Designer Villa 38’POOL w BEACH!

LUX 3,000 sq. ft. BIG PRIVATE VILLA, HUGE POOL & only a 3 min walk to the BEACH! Want one of the finest beach homes in the Caribbean with all new furnishings? Our rates for six (6) are unbeatable!🥂🥂🥂 Our ‘bedrooms’ are VERY LARGE individual private suites with mahogany & coral en-suite bathrooms! Nothing compares to ‘Happy Hour in the comfort of a chic, newly furnished designer beach house, a huge 38’ infinity pool with a 60’ long gorgeous veranda—just steps from gorgeous Honeymoon Beach

Guest favorite

Condo in St. Thomas

4.97 out of 5 average rating, 112 reviews

Oceanfront Condo Perfect Sunsets Backup Generator!

Our completely renovated one bedroom, one bathroom condo is PERFECT for couples, small families or a friends getaway. See the ocean and hear the waves from every room. Beautiful views, sounds, and location with private balcony. Centrally located, in a gated community, to some of the best beaches in the world and only 10 minutes from Red Hook (Ferries to St. John & BVI), Havensight (Cruise ship docks) and about 20 minutes from the airport. Steps to the oceanside pool, beach, and seaside dining.

Guest favorite

Condo in Northside

4.98 out of 5 average rating, 114 reviews

OCEAN VIEW! Condo near Magen's Bay Beach w/ POOL!

Welcome to your retreat with panoramic ocean views located in Mahogany Run, 5 minutes from Magen's Bay Beach. Enjoy spectacular views of the ocean from every room of the condo. This bright and airy condo is equipped with a plush king-size bed, a fully equipped kitchen, and a bathroom featuring a walk-in shower. Spend the days at one of the island's beaches, snorkeling, hanging out by the pool, or exploring downtown Charlotte Amalie! We HIGHLY recommend renting a car to get around the island.

Guest favorite

Rental unit in Northside

5 out of 5 average rating, 19 reviews

Ocean views from every room!

Relax and enjoy peaceful moments from this large one bedroom condo. Open the expansive windows and enjoy taking in the ocean breeze and amazing views. Serene and private while only being minutes away from Magen’s Bay. Watch the beautiful sunrises in the morning from the large balcony overlooking the Ocean and the nearby islands. Located across from the community pool for those days when you don’t feel like going to the beach. This unit can also be rented as a 2 bed/2 bath by special request.

Guest favorite

Guesthouse in Saint Thomas

5 out of 5 average rating, 62 reviews

Sunrise Cottage - Secluded, Romantic, Private

Sunrise cottage is located on the cool & breezy north side of St. Thomas. A relaxing 1 bedroom cottage with a full kitchen & living area. You can soak up the sun on the sundeck or hang out in your private soaking pool, while appreciating the breath taking view during the day & the abundance of stars at night. When venturing out you are 20 mins to Magen’s Bay Beach, 15 mins to Town, 30 mins to Red Hook. Note: The hosts live on property with 2 dogs and this cottage is adult only 18 or older.

Guest favorite

Condo in Southside

4.94 out of 5 average rating, 115 reviews

Stay in style right on the ocean -Simply the BEST!

Take a look at the fabulous view from our unit, you will hear the waves every minute of every day. Your patio is so close to the ocean that you can actually throw a coconut and hit the water. I have done it! This is the PERFECT location for your stay in America's Tropical Paradise. We just finished updating this unit in April ‘21 with new kitchen tile, new fridge, new cookware, dishware and kitchen utensils, Smart TV. You will NOT find a nicer condo for this price anywhere on the island.

Guest favorite

Rental unit in Saint Thomas

4.98 out of 5 average rating, 164 reviews

Hillside Hideaway

Perfect getaway for island romance, business, or solo adventuring. This well appointed one bedroom apartment is nestled in a quiet central hillside neighborhood with views of Hans Lollik, Jost Van Dyke, and Tortola islands. Conveniently located one mile from Magen's Bay and ten minutes to downtown Charlotte Amalie by car. Rental car is a must! Come enjoy the tranquil views, take a dip in the pool, and experience St. Thomas like a local. Please read all listing details and house rules.

Superhost

Condo in Southside

4.86 out of 5 average rating, 63 reviews

Ocean view condo - southside

This apartment offers floor-to-ceiling views of the majestic Caribbean Sea from its south-facing windows. The condo has a full kitchen, a ocean faced balcony and a cozy beachy vibe. Enjoy the warmth of glorious sunrises and sunsets, watching the amazing cruise ships pass by right outside the windows. Enjoy one of the three pools, the tennis court or the beach within walking distance! Centrally located on the island. Easy to take a taxi only 10-15 minutes to downtown or to redhook!

Superhost

Island in St. Thomas

4.8 out of 5 average rating, 268 reviews

Island Efficiency Escape

This unit is very small and cozy with great views of the seaports, airport, and downtown. Escape to your own oasis on the beautiful island of St. Tomas! This beautiful home features the following: *Pool *Free WiFi *Fully stocked kitchen *5 minutes to St. Thomas Airport *Coffee station *5-10 minutes from restaurants This unit is great for active solo adventurers or business travelers that are capable of using stairs. *This unit requires the use of stairs.*