Vacation rentals with a pool in Charlotte Amalie

4.93 out of 5 average rating, 113 reviews

Condo

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!

Apartment in Saint Thomas

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.

4.98 out of 5 average rating, 220 reviews

Guesthouse in Saint Thomas

A private infinity pool is situated on a terrace, overlooking lush greenery and a panoramic ocean view. A vibrant rainbow arcs across the horizon, while gentle waves suggest a tranquil atmosphere. The pool's edge blends seamlessly with the surrounding landscape.

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.

5.0 out of 5 average rating, 118 reviews

4.94 out of 5 average rating, 140 reviews

The living room features vaulted ceilings with wooden beams, large windows providing views of the water, and comfortable seating arrangements. A neutral color palette is complemented by decorative plants and light fabrics. Natural light fills the space, enhancing the open layout.

Villa in Southside

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.

A wooden bench with a sign reading 'SAIL AWAY' is positioned on a patio, overlooking the vibrant blue waters of a beach. Lush green foliage and palm trees frame the view, with rolling hills visible in the distance under a partly cloudy sky.

4.95 out of 5 average rating, 144 reviews

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.

5.0 out of 5 average rating, 104 reviews

An outdoor infinity pool is shown with tranquil waters extending towards the Caribbean Sea. Lush greenery and palm trees surround the area, with views of the coastline and sailboats on the horizon. The sky is partly cloudy, enhancing the serene atmosphere of the setting.

Home in Southside

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.

4.97 out of 5 average rating, 157 reviews

A serene beach scene captures clear turquoise waters gently lapping against the shore. Lush greenery cliffs rise in the background, adding natural beauty to the landscape. A small boat and a few swimmers can be seen enjoying the calm sea, enhancing the tranquil atmosphere.

Home in East End

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.

4.96 out of 5 average rating, 169 reviews

A balcony table is set with two plates of breakfast, accompanied by cups, overlooking the tranquil blue waters of the Caribbean Sea. The rhythmic sound of waves enhances the serene dining experience, with a clear sky and fluffy clouds visible in the background.

Condo in Saint Thomas

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! 🌴

Vacation home in Saint Thomas

A light-filled living area features a spacious white sofa paired with a geometric wooden coffee table. An open dining space with a wooden table and chairs can be seen in the background, while large sliding doors invite natural light and offer easy access to the outdoors.

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. 🐕

4.93 out of 5 average rating, 202 reviews

Apartment in Charlotte Amalie

The spacious living area features two light-toned sofas arranged around a glass coffee table, with a cozy bean bag on the floor. Natural light enters through two well-sized windows, creating an airy ambiance complemented by a modern floor lamp and a potted plant.

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.

4.99 out of 5 average rating, 156 reviews

4.91 out of 5 average rating, 98 reviews

A covered balcony showcases two rattan chairs and a small table, complemented by a potted plant. The view features vibrant blue waters, lush greenery, and distant hills under a clear sky, creating a relaxing outdoor space.

Apartment in East End

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.

Villa in Charlotte Amalie

An aerial view of a contemporary home reveals a red roof and an infinity pool lined with lounge chairs. Surrounding greenery enhances the sense of privacy, while a spacious driveway provides easy access. Large windows allow for plenty of natural light to enter the interior.

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.

4.99 out of 5 average rating, 104 reviews

Popular amenities for Charlotte Amalie rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.89 out of 5 average rating, 101 reviews

A private pool is highlighted in the foreground, with steps leading into the water. A spacious deck offers lounge chairs and a shaded dining area under a pergola. Clear blue skies and distant islands create a stunning coastal backdrop.

Home in Cruz Bay

Mar de Amores - October special!

4.99 out of 5 average rating, 100 reviews

A vibrant red ginger flower stands tall amidst lush green foliage, showcasing intricate layers of petal-like bracts. The natural lighting enhances its striking color, creating a vivid focal point within the tranquil garden setting.

Home in Cruz Bay

Wild Ginger at Casa Tre Fiori

Superhost

Home in Charlotte Amalie

Bellavista Grand Historic Villa | 6BR with Pool

4.9 out of 5 average rating, 10 reviews

5.0 out of 5 average rating, 84 reviews

A clear view of the pool surrounded by lush greenery, with a spacious deck offering seating options. The ocean is visible in the background, featuring varying shades of blue. The semi-open cottage can be seen adjacent to the pool, blending harmoniously with the natural landscape.

Home in Saint Thomas

Caribbean Poolside Cottage

4.9 out of 5 average rating, 51 reviews

An outdoor pool area presents inviting turquoise water surrounded by light-colored stone tiles. Lounge chairs are positioned beside the pool, with a palm tree casting gentle shadows. The expansive ocean view is framed by bright blue skies and fluffy clouds, creating a serene backdrop.

Home in West End

Secluded Paradise with Stunning Views & Pool

4.91 out of 5 average rating, 87 reviews

Home in Northside

4 King En-Suites • Ocean Views• Pool • Open living

4.99 out of 5 average rating, 72 reviews

Home in Northside

Island Retreat - Generator/Ocean View/Heated Pool

4.91 out of 5 average rating, 35 reviews

A modern building is surrounded by lush greenery and features a landscaped pathway leading to a spacious deck. Cozy seating areas are arranged around a jetted swim spa, creating an inviting outdoor space overlooking the scenic hills.

Home in Southside

Private Pickleball Court - 5 min walk to Beach

Condo rentals with a pool

A spacious balcony offers a relaxing seating area with comfortable chairs and a table, overlooking the scenic Sapphire Beach. Lush palm trees sway in the gentle breeze, framing views of the turquoise waters and distant mountains under a partly cloudy sky.

4.89 out of 5 average rating, 188 reviews

Seaside Escape at Sapphire Beach Resort

4.97 out of 5 average rating, 117 reviews

An outdoor balcony offers expansive ocean views, featuring a comfortable lounge chair and a dining set with cushioned seating. The blue waters of the Atlantic extend towards distant islands, framed by bright blue skies and white clouds, enhancing the serene atmosphere.

Condo in Lovenlund Gns

2 Bed Ocean Views, Gated Community & Backup Power

A modern living area is showcased with a light-colored sofa and a decorative rug. A flat-screen television is mounted on the wall opposite. The spacious layout connects to the bedroom area, where a king-size bed and soft linens are visible in the background.

4.97 out of 5 average rating, 108 reviews

HarborView @ Sapphire Beach *NEW Condo Listing*

4.95 out of 5 average rating, 130 reviews

An open-concept living area features high wooden ceilings and large sliding glass doors, providing unobstructed views of the ocean and surrounding islands. A dining table and chairs are visible alongside a turquoise cabinet, with a ceiling fan above for comfort.

Condo in Saint Thomas

Wrap Around Balcony~Views~Pack your Bathing Suit!

4.99 out of 5 average rating, 172 reviews

A spacious outdoor patio is featured with a dining table and colorful chairs, offering unobstructed ocean views. Large sliding glass doors lead to the living area, allowing natural light to fill the space. A gentle breeze and serene scenery are prominent.

Condo in Northside

Ocean Views | Near Magen’s Bay w/ Pool & Generator

4.85 out of 5 average rating, 163 reviews

Seas The Day

A covered balcony features two comfortable rattan chairs and a sofa, providing a cozy seating area. The view includes sandy beach and turquoise waters, with lush greenery in the background. Soft overhead lighting enhances the serene atmosphere.

4.97 out of 5 average rating, 201 reviews

Beachfront • King • W/D • By RH • Pool • Marina

4.94 out of 5 average rating, 139 reviews

A private balcony features two wicker chairs and a round table, providing an inviting space to enjoy the ocean view. The turquoise waters and gentle waves are visible in the distance, complemented by a clear blue sky.

Condo in Southside

So close you can taste the ocean - PRIME Location

Other vacation rentals with a pool

Superhost

Apartment in Saint Thomas

The Grande Escape in Yacht Haven Grand

5.0 out of 5 average rating, 4 reviews

A modern living area features a large flat-screen TV mounted above a stylish wooden media console. A light-colored sofa and accent chairs are arranged around a circular coffee table, with large windows offering views of the ocean and islands beyond. Natural light fills the space.

5.0 out of 5 average rating, 64 reviews

5 Star NEW Luxury Fully Remodeled 1x2 Pool & Beach

4.98 out of 5 average rating, 100 reviews

Villa in Anna's Retreat

Good Vibes Only Ocean Villa-Views/Pool/Sundeck/Fun

Apartment in Charlotte Amalie

Paradise at Luxurious Bluebeards Castle Resort

4.93 out of 5 average rating, 44 reviews

Superhost

A private balcony features a lounge chair and a small table adorned with tropical foliage. The expansive view reveals the ocean stretching towards distant islands, accompanied by a bright sky dotted with clouds.

Condo in Northside

Ocean View Condo Near Magen's Bay Beach!

4.85 out of 5 average rating, 96 reviews

4.96 out of 5 average rating, 77 reviews

Villa in Southside

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

5.0 out of 5 average rating, 24 reviews

A private infinity pool is surrounded by several lounge chairs, each featuring soft blue towels. Lush tropical vegetation frames the area, while unobstructed ocean views stretch into the distance, capturing serene coastal hues under a clear blue sky.

Villa in Northside

Private Villa*MagensBay *Ocean front* Private Pool