Holiday rentals with a pool in Charlotte Amalie

A sandy beach offers a serene view featuring clusters of leafy trees providing shade. The calm turquoise waters are visible in the background under a clear blue sky. Beach seating is scattered along the shoreline, inviting relaxation and enjoyment of the landscape.

5 out of 5 average rating, 189 reviews

"H2Oh What a Beach!" condo: Walk-out Beach Access!

"H2Oh What a Beach!" condo Building A of Sapphire Beach Resort & Marina: ground floor unit with direct access to one of the most beautiful beaches in the Caribbean. Steps away from Sea Salt fine dining restaurant, Sapphire Beach Bar, Paradise Pie pizza, and Beach Buzz coffee shop. A mile from Red Hook featuring many restaurants & island ferries. Great beach, swimming, snorkeling, parasailing, and relaxing right outside your door. Be among the many visitors who LOVE this totally renovated condo.

4.93 out of 5 average rating, 122 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 spacious bedroom is furnished with a large bed featuring a woven headboard. Light blue and white palm-patterned wallpaper adds a serene touch. A seating area with two chairs and a coffee table is visible, and sliding glass doors lead to a balcony overlooking the beach.

4.85 out of 5 average rating, 209 reviews

Charming Beach Condo w/ Balcony- 2 Pools and Beach

Located at Sapphire Village. Amazing balcony and views of Sapphire Beach and its turquoise waters. Short walk to the beach and beach bar! Completely renovated with new furniture- 1 KING bed, and one queen sleeper sofa. Property has hotel amenities including 2 pools, great snorkeling off of the beach, 3 restaurants, beach bar, coffee shop & deli! Secure safe location. Taxis are readily available for rides to grocery stores, Red Hook for dinner, St. John Ferry, beaches. 25 min from airport!

Apartment in Saint Thomas

A cozy living area is equipped with a dark blue sofa, a stylish lamp, and a wooden TV stand. A vibrant rug is placed on the floor, and natural light filters through the white window curtains. A decorative plant adds a touch of greenery to the space.

4.98 out of 5 average rating, 200 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.

4.96 out of 5 average rating, 208 reviews

HarborHouse-PRIME OCEANFRONT VILLA SAPPHIRE BEACH

Two story oceanfront VILLA with PRIME views of the marina and St. John at SAPPHIRE BEACH RESORT. This 1200 square ft. newly furnished, two story villa sleeps 6. It offers robes, outdoor couch and dining, grill, cable, upstairs and downstairs TV, two bathrooms, washer, dishwasher, and wifi. Relax in the large upstairs bedroom with cathedral wood planked ceilings and plush KING SIZE BED or enjoy lounging outside at one of TWO BALCONIES that offer the best views at Sapphire Beach Resort!

4.96 out of 5 average rating, 114 reviews

A spacious pool area is highlighted by a refreshing private pool, surrounded by a wooden deck. Two black loungers provide comfortable seating, while colorful inflatables add a playful touch to the clear water. The setting is brightened by large glass doors and subtle outdoor lighting.

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, 146 reviews

The living area features a spacious sofa and a patterned armchair arranged around a coffee table. Large sliding glass doors provide a view of the ocean and access to the balcony. A dining table with chairs is positioned near the window, allowing for bright natural light.

Condo in St. 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 beach, 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! 🌴

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.

5 out of 5 average rating, 106 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.

4.79 out of 5 average rating, 292 reviews

A spacious white villa with multiple arched windows is situated on a hillside, providing impressive views of the sea and surrounding islands. A large outdoor area features a pool, patio furniture, and a beautifully manicured garden, enhancing the inviting atmosphere of the property.

Island in St. Thomas

Sleek & Sunny Island Studio | Kitchenette

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.*

4.94 out of 5 average rating, 101 reviews

A serene pool area is depicted with a clear turquoise pool reflecting the sky. A graceful statue stands nearby, enhancing the tranquil setting. The distant view of the harbor is visible under a partly cloudy sky, framed by a decorative railing and outdoor seating.

Cottage in Northside

Caribia Cottage-Elegant Villa w/Private Pool

Caribia Cottage is located in a private Estate with access only through an electronic gate. The spectacular panoramic view of the St. Thomas Harbor is unforgettable and one which many a famous star toasted to when the property was formerly owned by a celebrated Broadway Producer. Walk just two steps from the Cottage into the spacious swimming pool. Enjoy gazing at the busiest Harbor in the Caribbean, as the mega yachts, seaplanes and cruise ships come and go.

4.92 out of 5 average rating, 165 reviews

A bright seating area features two modern white armchairs positioned near large windows, offering unobstructed views of the ocean and sky. A wooden side table with a lamp and decorative elements complements the room's light colors and contemporary design.

Condo in Northside

Ocean View Studio • Near Magens • Pool & Generator

Wake up to sweeping ocean vistas just 5 min from iconic Magen's Bay Beach. This remodeled studio seats you on the hillside with ocean views. • Shared pool • Back-up generator & fast Wi-Fi • King bed • Full kitchen & beach gear (snorkels, chairs, umbrella) Minutes to restaurants, Red Hook ferries and island adventures. Book your carefree St. Thomas escape today! We highly recommend renting a car to get around the island.

4.87 out of 5 average rating, 109 reviews

A sunlit deck features a private pool surrounded by a wooden railing, offering sweeping views of the ocean and lush hills. Palm trees sway gently in the breeze, completing the serene landscape under a clear blue sky dotted with fluffy white clouds.

Home in Saint Thomas

Villa Beso Del Sol - Three Bedroom Cozy Oasis

Villa Beso Del Sol is a three bedroom, three bath beach oasis nestled into the hills above the historic town of Charlotte Amalie. We are located in estate Solberg, once you arrive you may not want to leave, the pool is partially covered so you have the option of soaking in the shade or soaking in ALL the sun. Morning coffee or afternoon cocktails, the outdoor pool area is where you'll want to be your entire vacation.

Popular amenities for Charlotte Amalie rentals with a pool

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

A spacious outdoor area features a private pool surrounded by sun loungers. A large palm tree provides shade, while vibrant greenery frames the scene. Scenic views of the Caribbean Sea and harbor are visible in the background, enhancing the inviting atmosphere.

4.95 out of 5 average rating, 65 reviews

Private Saltwater Poolside Cottage w/View and Gate

4.98 out of 5 average rating, 54 reviews

An outdoor infinity pool offers serene views of the ocean and surrounding greenery. Four blue lounge chairs are positioned near the water's edge, providing a perfect spot for relaxation. Bright blue skies and distant islands complete the picturesque landscape.

Home in NorthSide

Ocean View Retreat- 2BR/2BA Heated Pool, Generator

A bright living area features two round woven coffee tables and two accent chairs with soft cushions. Artistic prints of herons are displayed on the wall, while large glass doors offer a view of the private plunge pool and outdoor space filled with greenery.

5 out of 5 average rating, 8 reviews

NEW Villa La Brisa Luxe Hideaway

A private pool area is surrounded by loungers and shaded by large umbrellas. The pool features clear waters and is bordered by a brick patio. Lush greenery and the home's exterior can be seen in the background, illustrating a tranquil, tropical environment.

5 out of 5 average rating, 21 reviews

The Caribbean Farmhouse/Ocean Views, Solar Power

5 out of 5 average rating, 10 reviews

A large private pool is framed by a spacious deck, offering stunning views of the turquoise Caribbean waters. Comfortable loungers are positioned nearby, inviting relaxation. The clear sky above enhances the serene atmosphere, making it ideal for enjoying the surrounding natural beauty.

Home in Saint Thomas

Villa Paradis II! Private Pool! Amazing Views!

A private deck features two woven lounge chairs facing the ocean, offering expansive views of the sparkling blue water and distant islands. Lush greenery is visible at the edge of the deck, complementing the serene atmosphere under a clear sky with scattered clouds.

5 out of 5 average rating, 37 reviews

Oceanfront Private Caribbean Resort!

5 out of 5 average rating, 56 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

4.73 out of 5 average rating, 11 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 marina scene is displayed, featuring a variety of sailboats and yachts moored alongside a serene blue waterway. Lush green palm trees frame the view, while distant islands are visible against a clear sky with a few fluffy white clouds.

4.99 out of 5 average rating, 216 reviews

Stunning Ocean View w/Balcony~Shades of Sapphire~

A spacious sleeping area features a large bed with soft linens, complemented by a cozy seating arrangement nearby. Floor-to-ceiling glass doors offer stunning views of the ocean and outdoor seating. A modern entertainment unit provides convenience with a flat-screen TV.

4.93 out of 5 average rating, 101 reviews

Seas The View-Updated & Oceanview @ Sapphire Beach

4.84 out of 5 average rating, 271 reviews

A sunset casts warm hues across the sky, with a golden sun partially hidden behind distant hills. Silhouetted palm trees frame the scene, standing against the tranquil ocean waters reflecting the colorful sky.

Condo in St. Thomas

REGATTA R&R

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.

4.94 out of 5 average rating, 123 reviews

Sail Away II-WOW Beachfront to Paradise Remodeled

4.83 out of 5 average rating, 269 reviews

A serene outdoor space features a private pool surrounded by a sun-soaked patio. Lounge chairs are positioned comfortably nearby, with large sliding glass doors revealing an inviting interior. Lush greenery frames the area, enhancing the sense of seclusion and tranquility.

Condo in Smith Bay

Romantic Private Pool Villa@Sapphire. Generator.

4.96 out of 5 average rating, 208 reviews

Clear turquoise waters are framed by smooth, large boulders, with a view of boats floating nearby. Fluffy white clouds drift over a serene sky, while distant islands are visible on the horizon, enhancing the tranquil beach atmosphere.

Condo in Sapphire Beach

Salt Life at Sapphire Beach

4.94 out of 5 average rating, 125 reviews

A beachfront view captures the clear turquoise waters lapping against a rocky shore. Lush palm trees sway gently in the foreground while various buildings line the beach. Rolling green hills rise in the background under a bright blue sky with scattered clouds.

Condo in Southside

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

4.83 out of 5 average rating, 350 reviews

A private balcony overlooks clear turquoise waters and distant hills. A potted palm tree adds greenery, while a pathway leads to seating areas. Sailboats float gently in the bay, creating a serene coastal view, with bright blue skies and fluffy white clouds enhancing the scene.

Condo in Smith Bay

Oceanfront Apt with Panoramic Views

Other holiday rentals with a pool

4.9 out of 5 average rating, 30 reviews

A serene beachfront is captured at sunset, featuring soft sandy shores that gently meet the calm water. Lush palm trees frame the scene, while rocky formations are visible along the shoreline, enhancing the natural coastal beauty.

Apartment in Southside

Frenchmans Limetree USVI Studio

5 out of 5 average rating, 4 reviews

An expansive infinity pool is framed by palm trees, with steps leading into the crystal-clear water. In the background, a serene view of the ocean and hills can be seen, complemented by a shaded seating area under a blue umbrella.

Villa in Southside

Christmas Week at Marriott's Frenchman's Cove!

5 out of 5 average rating, 20 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

4.98 out of 5 average rating, 80 reviews

Villa in Anna's Retreat

Good Vibes Only Ocean Villa-Private Pool-Views!

4.99 out of 5 average rating, 69 reviews

A private plunge pool is positioned on a spacious wooden deck, complemented by vibrant lounge chairs and surrounded by lush tropical foliage. The stunning blue waters of the ocean create a captivating backdrop, enhancing the serene atmosphere of the outdoor space.

Villa in West End

Villa Morning Glory - Private Pool - Amazing Views

5 out of 5 average rating, 17 reviews

A serene pool area features clear blue water surrounded by lush greenery and palm trees. Sun loungers in light green are positioned nearby, with a thatched-roof structure in the background offering shaded seating and colorfully upholstered chairs.

Condo in St. Thomas

*Margarita-ville Resort* Studio Suite (Sleeps 2)

4.95 out of 5 average rating, 22 reviews

A sweeping view of a tranquil bay is captured, showcasing turquoise waters meeting the skyline. Sailboats are anchored in the harbor, while a sandy beach curves along the shore. Lush green hills frame the scene, leading to distant mountainous landscapes under a clear blue sky.

Condo in Northside

Unplug & Unwind