Vacation rentals with a pool in Water Island

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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

Villa in Southside

4.96 out of 5 average rating, 46 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!

Jul 26 – Aug 2

G$97,675 GYD per night

Guest favorite

Condo in Northside

4.92 out of 5 average rating, 101 reviews

OCEAN VIEW! Studio near Magen's Bay Beach w/ Pool!

Welcome to your newly remodeled ocean view studio located in Mahogany Run, just 5-mins from Magen's Bay Beach. Enjoy spectacular views of the ocean from the bed or seating area. This bright and airy studio 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.

Apr 25 – May 2

G$35,850 GYD per night

Guest favorite

Apartment in Northside

5.0 out of 5 average rating, 11 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.

Aug 23 – 30

G$59,777 GYD per night

Guest favorite

Home in NorthSide

5.0 out of 5 average rating, 19 reviews

New Build-Heated Pool, Ocean View, Awesome Patio

Welcome to Sunrise Villas by Stacie! Enjoy island living at our newly constructed home offering breathtaking ocean/island views. Enjoy your favorite cocktail in our heated pool with baja sun deck (bubblers/jets/lights). Relax in our spacious indoor/outdoor space with 20 foot sliding door, huge kitchen island, bar, and fireplaces. 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 (send inquiry for link)!

Oct 15 – 22

G$118,895 GYD per night

Superhost

Condo in Southside

4.93 out of 5 average rating, 106 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.

Nov 25 – Dec 2

G$35,044 GYD per night

Guest favorite

Guesthouse in Saint Thomas

5.0 out of 5 average rating, 52 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.

Mar 10 – 17

G$60,044 GYD per night

Guest favorite

Apartment in Saint Thomas

4.97 out of 5 average rating, 153 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.

Oct 4 – 11

G$28,191 GYD per night

Guest favorite

Villa in Northside

5.0 out of 5 average rating, 10 reviews

Private Villa*MagensBay*Ocean views*Private Pool

Villa Del Mar is a luxury vacation rental villa offering two bedroom suites, luxurious great room, three dining areas and five private terraces. Our guests enjoy ocean views from every room including the pool and terraces. The villa sleeps up to four guests within two private suites with king beds, en-suite bath, walk in closets, individual A/C units & private terraces with unobstructed ocean views. Suite One's private outdoor double shower looking over the palm trees is dreamy.

Sep 9 – 16

G$133,909 GYD per night

Guest favorite

Villa in Water Island

4.96 out of 5 average rating, 25 reviews

2 LUX Private Suites HUGE Pool+Beach 5 Star Villa

LUX 3,000 sq. ft. BIG PRIVATE VILLA, HUGE POOL & only a 3 min walk to the BEACH! This 5-Star Dream Vacation Home is one of the finest in the Caribbean💫 And our rates for six are unbeatable! Our ‘bedrooms’ are VERY LARGE individual private suites with mahogany & coral en-suite bathrooms! Nothing compares to watching the cruise ships sail by from our 38’ infinity pool, dining Al fresco on the 60’ long veranda, endless Caribbean views & just steps from gorgeous Honeymoon Beach!

Dec 7 – 14

G$157,795 GYD per night

Guest favorite

Apartment in Charlotte Amalie

5.0 out of 5 average rating, 28 reviews

Chic 1 Bedroom Oasis with Designer Decor & Pool

Welcome to our impeccably designed oversized 1-bedroom apartment (+ queen size Murphy bed) a stylish retreat that promises an unforgettable stay in the heart of the historic district of Charlotte Amalie with its own plunge pool and deck. This apartment boasts a sophisticated ambiance, curated with the finest designer furnishings, decor and lighting as well as a custom kitchen. This is a perfect location to serve as the base to explore St. Thomas and the surrounding islands.

Jul 6 – 13

G$57,224 GYD per night

Guest favorite

Home in Saint Thomas

5.0 out of 5 average rating, 13 reviews

Caribbean Poolside Cottage

Take it easy at this unique and tranquil getaway. Enjoy million-dollar views of the Caribbean while relaxing in your poolside oasis. Nestled atop St. Thomas, this brand new air-conditioned cottage affords breathtaking sunrises and sunsets. Centrally located, you are 5 minutes from world-famous Magens Bay beach, Hull Bay, and downtown Charlotte Amalie. Join the locals at Sib's restaurant and bar, only a two-minute walk away.

Aug 9 – 16

G$38,745 GYD per night

Guest favorite

Condo in Saint Thomas

4.9 out of 5 average rating, 70 reviews

Little Fairway at Mahogany Run, Quiet & Cozy

COMPLETELY RENOVATED IN APRIL 2023! Welcome to Little Fairway, a perfect tiny space for couples or a solo adventurer! A cozy studio condo located in Fairway Village at Mahogany Run. Little Fairway is a small, 500 square foot condo on the north side of St.Thomas. It has a full kitchen and is steps away from the pool! This bright and tiny space close to Magen’s Bay is the perfect location for vacationing on this small island!

Aug 26 – Sep 2

G$24,105 GYD per night