Vacation rentals with a pool in Charlotte Amalie

Wrap Around Balcony w/Amazing Views! Remodeled!

Book Now! Down Island Dream is a 1BR/1BA luxury villa located @Point Pleasant on the East End of St Thomas. 2 Restaurants, 3 pools, nature trail & small intimate beach to enjoy. Your vacation home/5 minutes to Red Hook w/shops, bars, restaurants & the ferry to St John where you can explore, hike & enjoy our National Park Beaches! 3 mins to Lindquist & Coki beaches. Amazing views & refreshing breezes await you at Down Island Dream! Try our home away from home for the week & fall in love!

Location · Value · Bathroom

Hillside Hideaway

Perfect getaway for an island getaway, 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.

Family · Value · Condition

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 21 or older.

Location · Value · Parking

Sunset Terrace | Epic Views, Pool, & Family Fun!

Sunset Terrace offers panoramic views of the Caribbean Sea and surrounding islands from nearly every room. This fully air-conditioned villa features a private saltwater pool, four en-suite bedrooms, and spacious living and dining areas. . Relax on the covered patio, grill outdoors, or lounge poolside. Just a 5-minute drive to beaches, restaurants, and shopping. Perfect for families or groups, with kid-friendly amenities, backup generator, and concierge support for a seamless St. Thomas stay.

Family · Location · TV

Sail Away II-WOW Beachfront to Paradise Remodeled

Full property generator. Sail Away II at Sapphire Beach Resort and Marina is located on the beachfront just steps away from the sparkling Sapphire Beach. The patio leads you to a dazzling infinity pool and the option of 2 immaculate beaches. Caribbean water and amenities galore await you. No need to leave the tranquility of your room thanks to the many home furnishings within your vacation paradise. Beach level, beachfront & lush surroundings is yours to escape the hub of city life.

Value · Location · Getting around

Entire villa with beautiful views! Amazing

Overlooking Bolongo beach. Perfect for couples traveling together but want plenty of privacy as well. 1200 sf covered patio to enjoy sunning, relaxing, dinners with family and friends while being soothed by waves and wonderful breezes. Two bedrooms, each with full baths in main house AND two private apartments below each having the same wonderful views! Perfectly located between Red Hook for ferry to St. John and Havensight for shopping. Catch the beautiful sunrises and sunsets.

Location · Value · Pool

Private Pool in Paradise! Ocean View Steps 2 Beach

Come enjoy the island life at this tranquil villa with private pool...only steps from the beach! Cooler, snorkeling gear, and beach chairs INCLUDED! The entire home has been remodeled. The pool has been fully updated as well as the deck area, which includes brand new furniture and high-end loungers. A new gas grill has also been added for your outdoor grilling pleasure. Stream all your favorites with our strong Wi-Fi. Upscale restaurant, Pangea, is just steps away. Free parking.

Family · Location · Walkability

Oceanfront Bliss & Perfect Sunsets + Backup Power

Our fully renovated 1BR/1BA condo is PERFECT for couples, small families or a friends getaway. Enjoy stunning ocean views and the sound of waves from every room or your private balcony. Watch breathtaking sunsets and cool off in one of three crystal-clear pools. Located in a gated community, just steps from the ocean, oceanside pool, and seaside dining. Only 10 min to Red Hook (ferries to St. John & BVI) and Havensight, and 15 min from the airport—your perfect island escape! 🌴

Location · Family · Laundry

Villa La Realeza - Award Winning Design - VIEWS!

Welcome to Villa LaRealeza inside Point Plesent. This Villa is the perfect island vacation rental in St Thomas, and is located inside the guard gated community. The Villa offers the perfect blend of relaxation & adventure. Relax by the pools or simply enjoy amazing views from the private wrap around patio with views of St John & Tortola islands. When you rent with us directly here on airbnb you save $! Unfortunately, the community does not allow renters pets on site. 🐕

Location · Value · Air conditioning

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.

Location · Value · Amenities

Gigi’s Luxury Beach Hideaway | Pool & Beach

Have fun with the whole family at our stunning and recently renovated 3-bedroom, 2-bathroom condo, located East End at the highly sought after gated property of Cowpet Bay West. This luxurious retreat comfortably accommodates up to 6 guests and offers breathtaking views, stylish furnishings, and resort amentities including a pool, hot tub, beach, watersport rentals, and two restaurants on property. Back-up generator on property for any island wide power outages.

Location · Family · Condition

Hilltop Paradise Vacation Package with Jeep

Start your next adventure and step into this brand new contemporary modern home hidden in the hills of St. Thomas. Here, you will be greeted with incredible, breathtaking views and an infinity pool overlooking the beautiful Charlotte Amalie. This carefully designed retreat sets the tone for a perfect adventure getaway for a group of friends/couples, or the perfect relaxation stop for a family. Whatever you choose, this home will not disappoint.

Location · Family · TV