Luxury Vacation Rentals with a Private Pool in Charlotte Amalie

Never book a bad vacation home again. Every Wander comes with hotel-grade amenities, inspiring views, pristine cleaning and 24/7 concierge service.

We found 25 private pool vacation rentals – enter your dates for availability.

Top-rated private pool vacation rentals in Charlotte Amalie

Luxury

Ruby Ridge

4 bedrooms•4 baths

•

~$350 less than other sites

Skyline Sunshine

3 bedrooms•3 baths

•

~$210 less than other sites

CalypsoBlu

3 bedrooms•3 baths

•

~$235 less than other sites

Luxury

Bellevue Estate

9 bedrooms•8 baths

•

New

~$1,550 less than other sites

Bella Vida

3 bedrooms•3 baths

•

~$135 less than other sites

Luxury

Sunset Sanctuary

5 bedrooms•5 baths

•

~$415 less than other sites

Villa Mas

4 bedrooms•4 baths

•

~$545 less than other sites

Island Paradise Getaway

5 bedrooms•3 baths

•

~$290 less than other sites

Welcome to private poolside luxury in Charlotte Amalie

Set your trip on island time with Wander’s luxury private pool vacation rentals in Charlotte Amalie. Each home pairs the polish of a five-star hotel with the comfort of a private residence, so you can settle in the moment you arrive.

Swim at your pace in your own pool, then stretch out on generous sun decks framed by sweeping Caribbean views. Expect pristine cleaning, ultra fast WiFi, thoughtfully equipped kitchens, spacious living areas, and serene bedrooms designed for deep rest, plus 24/7 concierge support. Whether you are balancing meetings and ocean breezes or simply unwinding, our Charlotte Amalie homes make every detail effortless.

Available soon in Charlotte Amalie

Luxury

Ruby Ridge

4 bedrooms•4 baths

•

~$350 less than other sites

CalypsoBlu

3 bedrooms•3 baths

•

~$235 less than other sites

Luxury

Sunset Sanctuary

5 bedrooms•5 baths

•

~$415 less than other sites

Island Paradise Getaway

5 bedrooms•3 baths

•

~$290 less than other sites

Luxury

Calypso Delight

5 bedrooms•5 baths

•

~$330 less than other sites

Bellevue Estate

2 bedrooms•2 baths

•

New

~$585 less than other sites

Salt & Sage

6 bedrooms•6 baths

•

~$260 less than other sites

Luxury

Bellevue Estate

6 bedrooms•6 baths

•

New

~$870 less than other sites

Featured private pool vacation rentals in Charlotte Amalie

Luxury

Bellevue Estate

9 bedrooms•8 baths

•

New

~$1,550 less than other sites

Luxury

Sunset Sanctuary

5 bedrooms•5 baths

•

~$415 less than other sites

Villa Mas

4 bedrooms•4 baths

•

~$545 less than other sites

Luxury

One Perfect Day

9 bedrooms•9 baths

•

~$2,780 less than other sites

Bellevue Estate

2 bedrooms•2 baths

•

New

~$585 less than other sites

Luxury

Bellevue Estate

6 bedrooms•6 baths

•

New

~$870 less than other sites

St. Sheridan Island

5 bedrooms•5 baths

•

~$520 less than other sites

Luxury

Windsong

6 bedrooms•6 baths

•

~$1,000 less than other sites

Highlights in Charlotte Amalie

Discover a vibrant Caribbean capital rich in Danish colonial history, world-class duty-free shopping, and breathtaking white-sand beaches.

Fort Christian

99 Steps

Magens Bay

Skyride to Paradise Point

St. Thomas Synagogue

Drake's Seat

IT'S A VACATION HOME, BUT BETTER

The Wander difference

Wander is different because we combine the quality of a luxury hotel with the comfort of a private vacation home. Your best trip ever is just a few clicks away.

Only the best homes

We’ll never not look like the pictures. Every Wander is beautiful and expertly operated, so you can leave any stress at the door.

Hotel-grade amenities

We’ll never leave you with nothing to do. From ultra fast WiFi to gyms and pools, our homes make it easy to blend work and play.

24/7 concierge service

We’ll never leave you hanging. Our chat-based Concierge is always available to help – from trip questions to special requests.

Inspiring and stunning views

We’ll never leave you uninspired. Every Wander has stunning views to refresh and inspire your soul. Adventure awaits.

Meticulous cleaning

We’ll never have you check in to a dirty house. Our cleaning teams are meticulous, and there are no chores at checkout.

Safety and security

We’ll never pass you off to a stranger. Every Wander location meets our industry-leading safety standards to give you peace of mind.

All homes in Charlotte Amalie

Luxury

Ruby Ridge

4 bedrooms•4 baths

•

~$350 less than other sites

Skyline Sunshine

3 bedrooms•3 baths

•

~$210 less than other sites

CalypsoBlu

3 bedrooms•3 baths

•

~$235 less than other sites

Luxury

Bellevue Estate

9 bedrooms•8 baths

•

New

~$1,550 less than other sites

Bella Vida

3 bedrooms•3 baths

•

~$135 less than other sites

Luxury

Sunset Sanctuary

5 bedrooms•5 baths

•

~$415 less than other sites

Villa Mas

4 bedrooms•4 baths

•

~$545 less than other sites

Island Paradise Getaway

5 bedrooms•3 baths

•

~$290 less than other sites

View all homes

Most popular amenities for private pool vacation rentals in Charlotte Amalie

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Discover more beyond the pool in Charlotte Amalie

Charlotte Amalie is the storied heart of the US Virgin Islands, where terraced hills cascade to a yacht-filled harbor and sunset colors linger over the water. Cobbled lanes and coral-hued fortifications reflect Danish heritage, while lively waterfront energy sets an unmistakable island rhythm.

Days drift between calm coves, sailboat charters, and panoramic lookouts that sweep toward neighboring isles. Evenings arrive with soft trade winds and starry skies that invite slow, unhurried nights. This is why Wander’s luxury vacation rentals in Charlotte Amalie are the perfect choice, whether you are traveling for work or leisure.

FAQs: Vacation Rentals in Charlotte Amalie

Why should I book a Wander in Charlotte Amalie over other private pool vacation rentals?

Wander offers a level of consistency and quality you won’t find with most private pool vacation rentals.

Every home in Charlotte Amalie delivers the quality of a luxury hotel, paired with the comfort and space of a private vacation home. You get hotel-grade amenities, meticulous cleaning, stunning views, and 24/7 concierge support in every stay. Why would you want to stay anywhere else?

Which are Wander’s most popular private pool vacation rentals in Charlotte Amalie?

Some of our most popular private pool vacation rentals in Charlotte Amalie include Ruby Ridge, Skyline Sunshine 3BR, and CalypsoBlu. Guests love the quality of a luxury hotel, the comfort of a private vacation home, and the consistently exceptional experience Wander is known for. Explore the full collection to find the perfect home for your next stay.

How many different private pool vacation rentals does Wander have available in Charlotte Amalie?

Wander offers 25 private pool vacation rentals in Charlotte Amalie, each carefully designed and expertly operated. Browse the full collection to see what’s available for your trip.

What time is check-in and check-out at Wander’s private pool vacation rentals in Charlotte Amalie?

You can check-in to Wander private pool vacation rentals in Charlotte Amalie after 4.00pm and check-out before 10.00am.

Do Wander’s private pool vacation rentals in Charlotte Amalie have WiFi access?

Yes. Every Wander home in Charlotte Amalie has ultra fast, reliable WiFi so you can stay connected throughout your stay.

What is Wander’s cancellation policy?

You can cancel your reservation within 24 hours of booking for a full refund.

For stays of less than 15 nights, you can cancel or reschedule up to 14 days before check-in for a full refund. For stays of 15 nights or longer, the cancellation window is 60 days.

For some homes, a 30-day deadline applies; this will be clearly shown before you book.