Vacation rentals with a pool in Charlotte Amalie

4.96 out of 5 average rating, 146 reviews

An inviting ocean-side pool is surrounded by a spacious deck with several lounge chairs and tables. Clear blue water reflects the sunlight, while the vast ocean extends beyond the pool area, providing a stunning backdrop.

Condo in St. Thomas

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 15 minutes from the airport. Steps to the oceanside pool, beach, and seaside dining.

4.85 out of 5 average rating, 204 reviews

Condo in East End

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 serene pool area is framed by natural rock formations and tropical greenery. The clear water reflects the surrounding landscape, and a tiled border enhances the pool's inviting appearance. A wooden deck provides ample space for relaxation, creating a peaceful outdoor setting.

4.98 out of 5 average rating, 199 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.

4.99 out of 5 average rating, 144 reviews

Condo in Northside

VIEWS! Condo by Magen's Beach w/ POOL & generator!

Welcome to your retreat with panoramic ocean views located in Mahogany Run, 5 mins 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

4.96 out of 5 average rating, 109 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.

Apartment in Charlotte Amalie

An inviting plunge pool is set against a backdrop of lush hills and rooftops. The pool's clear water reflects the serene surroundings, while the elegant stone deck provides a welcoming space for relaxation. The view captures the essence of the tropical landscape.

5 out of 5 average rating, 104 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.

4.95 out of 5 average rating, 108 reviews

A clear blue pool is framed by palm trees and tropical plants, with sun loungers arranged around its perimeter. The expansive ocean view is visible in the background, under a vibrant sky. The surrounding patio is paved with natural stone.

Condo in Southside

Sea Dreams at Regatta Point Villas

Regatta Point Villas is located in Bolongo Bay, St. Thomas. This spacious condo (2 full baths and 1 bedroom) features 1000sq.ft. of living space and is located steps away from the pool. It has beautiful ocean views from each room. Bolongo beach is a short walk and has great snorkeling. 2 Tennis Courts, basketball hoop, and 3 pools are all accessible and steps away from the ocean. A short drive to Havensight and Redhook with many beaches and restaurants to choose from.

4.79 out of 5 average rating, 290 reviews

A clear swimming pool is framed by light-colored concrete and illuminated by sunlight. Two lounge chairs sit beside the pool, offering a place to relax. In the background, views of the ocean and islands are visible under a partly cloudy sky.

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.*

4.89 out of 5 average rating, 114 reviews

The image captures a serene view of a multi-level pool surrounded by lush greenery and palm trees. The expansive blue ocean glimmers in the background under a clear sky, while sun loungers are positioned around the pool, inviting relaxation.

Condo in Southside

Sunshine Daydream - Our little piece of paradise!

Spend your days between at Sunshine Daydream with its beautiful ocean views. Rise up to paradise enjoying the gorgeous sunrises and sunsets from the private rooftop deck. This rental offers a fully equipped kitchen, 3 different pools, one of which is steps from the condo. There is easy beach access and we are centrally located between Charlotte Amalie and Red Hook. To top it off there are 2 restaurants and a bar within walking distance from the unit.

Apartment in Charlotte Amalie

A private balcony features a round table set for two, adorned with a vase of yellow flowers. Two turquoise chairs are positioned around the table, overlooking a scenic view of the turquoise waters and lush hills of St. Thomas, creating a welcoming outdoor dining space.

4.92 out of 5 average rating, 172 reviews

St. Thomas Studio w/ Balcony & Pool

Experience your island escape at this charming studio villa, offering stunning balcony views over St. Thomas from Bluebeard’s Hilltop Villas. Guests enjoy tennis courts, a poolside spa, dining options, and concierge services, all within a lively resort atmosphere. Ideally located minutes from Charlotte Amalie’s shopping, beaches, and excursions, this villa is your ideal Virgin Islands retreat for both relaxation and adventure.

4.88 out of 5 average rating, 107 reviews

An inviting outdoor pool area is framed by a wooden deck, providing shaded seating under a pergola. Two loungers are positioned next to the pool, with lush greenery surrounding the space. The exterior showcases a blend of stone and white walls, offering a comfortable retreat.

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.