
Holiday rentals with a pool in Charlotte Amalie
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Top-rated rentals with a pool in Charlotte Amalie
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Book Now! Caribbean Sunshine! Amazing Views!
Book Now! Down Island Dream is a 1BR/1BA luxury villa @Point Pleasant Villas on the East End of St Thomas. 2 Restaurants, 3 pools, nature trail & a 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!

The Green Goat Waterfront | Pool & Magens Views
Wake up to breathtaking waterfront views of Magens Bay in this serene St. Thomas, USVI villa, designed for effortless Caribbean island living. The interior offers single-level living with no interior steps; pool just below. Enjoy premium bedding & a complimentary Cruzan cocktail at our welcome bar. A 4x4 is needed to access this stunning oceanfront retreat near Magens Bay, Hull Bay & Charlotte Amalie. Snorkel, swim & explore St. John by ferry. Perfect USVI vacation rental for couples & families.

"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. Check out our reviews - there's a reason why we're always full!

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.

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.

Ocean View Condo near Magen’s Bay - 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

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.

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! 🌴

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.

Tranquil Getaway with Jeep
Immerse yourself in the beauty of this island and experience ultimate relaxation in this contemporary modern and elegant apartment. Indulge in the beauty of nature while soaking in breathtaking views of the historic waterfront/downtown Charlotte Amalie, French Town, Yacht Haven Grand, St Croix, Hassel Island, Water Island and so much more. Unwind in the infinity pool and relish the secluded paradise. Jeep is included with this home to ensure a remarkable experience!

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.*

Caribe Blue Tropical Paradise-Modern, Heated Pool
Sweeping views of Magens Bay, a lagoon pool (heated to a comfortable 85 degrees), and lush tropical gardens surround this stunning two bedroom, two bathroom villa. The villa has all the modern amenities to ensure you have a relaxing tropical vacation and is a 5 minute drive to Magens Bay beach and even less to dining options. Caribe Blue is newly renovated and re-decorated, so experience the new lagoon pool and cool contemporary design yourself!
Popular amenities for Charlotte Amalie rentals with a pool
House rentals with a pool

Villa Bliss - 3 Bedroom Island Oasis

Island Retreat - Generator/Ocean View/Heated Pool

Regatta Point! Ocean View Condo!

Tropical Shores a Waterfront Villa

Caribbean Poolside Cottage

Private Pickleball Court - 5 min walk to Beach

3 BR Villa with Stunning Harbor Views

Honeycomb Hideaway
Apartment rentals with a pool

Rockroom One Bedroom Condo at The Hills Saint John

BEST REVIEWS on the East End - HANDS DOWN!

Sunrise Sapphire West-A Building-NEW AC-

Sail Away II-WOW Beachfront to Paradise Remodeled

Romantic Private Pool Villa@Sapphire. Generator.

Wrap Around Balcony~Views~Pack your Bathing Suit!

Stay in Style right on the Ocean -Simply the BEST!

Seas The Day
Other holiday rentals with a pool

Eclectic Vibes/Epic Views & Seriously Great Pool!

Villa View Caribe

Exquisite Hillside Condo 2 - St. Thomas, U.S.V.I.

Condo with Northside Views & Back-Up Generator

Paradise Retreat | Oceanview | Balcony | 3 Pools

Amazing Ocean View 2BR/2BA Condo Near Magens Bay

Seaside Blue

Sapphire C-Scape:WALKOUT ON SAPPHlRE W/ Generator
When is the best time to visit Charlotte Amalie?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $565 SGD | $506 SGD | $510 SGD | $492 SGD | $498 SGD | $397 SGD | $416 SGD | $355 SGD | $382 SGD | $382 SGD | $498 SGD | $460 SGD |
| Avg. temp | 26°C | 26°C | 26°C | 27°C | 28°C | 29°C | 29°C | 29°C | 29°C | 29°C | 28°C | 27°C |
Quick stats about holiday rentals with a pool in Charlotte Amalie

Total holiday rentals
Explore 50 holiday rentals in Charlotte Amalie

Nightly prices starting at
Charlotte Amalie holiday rentals start at $115 SGD per night before taxes and fees

Verified guest reviews
Over 620 verified reviews to help you choose

Family-friendly holiday rentals
10 properties offer extra space & child-friendly amenities

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wifi availability
50 of Charlotte Amalie holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Charlotte Amalie rentals

4.7 Average rating
Charlotte Amalie stays receive an average rating of 4.7 out of 5 from guests
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- Flamenco Beach
- Limetree Beach
- Magens Bay Beach
- Honeymoon Beach
- Coki Beach
- Secret Harbor Beach
- Cane Garden Beach
- Cinnamon Bay Beach
- Cane Bay Beach
- Virgin Islands National Park
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- The Baths
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