Luxury Vacation Rentals with a Private Pool in Charlotte Amalie East

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 East

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 East

Elevate your island stay with Wander’s luxury private pool vacation rentals in Charlotte Amalie East, VI. We pair the polish of a luxury hotel with the privacy of a beautifully designed home, so every moment feels effortless.

Our collection features sunlit living spaces, chef-ready kitchens, premium linens, and ultra fast WiFi. Each home presents a sparkling private pool beside generous terraces and sweeping sea or harbor views, all cared for with pristine cleaning and supported by 24/7 concierge.

With thoughtful layouts, indoor-outdoor living, quiet work nooks, and fitness options, every detail is considered. What you see in the photos is exactly what you’ll experience, and it is all yours.

Available soon in Charlotte Amalie East

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 East

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 East

Discover a tropical paradise of pristine white-sand beaches, historic Danish fortresses, and breathtaking hilltop vistas in Charlotte Amalie East.

Skyride to Paradise Point

Magens Bay Beach

Fort Christian

Coral World Ocean Park

Drake's Seat

Yacht Haven Grande

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 East

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 East

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Discover more beyond the pool in Charlotte Amalie East

Set between emerald hills and a yacht-dotted harbor, Charlotte Amalie East blends Danish-era charm with a lively Caribbean rhythm. Historic streets step up the hillside, pastel facades frame the waterfront, and boutique shopping adds a refined edge to days in town.

From soft trade winds to glowing sunsets over the bay, the atmosphere is both energizing and serene. Its central setting makes it easy to balance leisurely hours and light workdays without losing the island vibe. This is why Wander’s luxury private pool vacation rentals in Charlotte Amalie East, VI are the perfect choice, whether you’re traveling for work or leisure.

FAQs: Vacation Rentals in Charlotte Amalie East

Why should I book a Wander in Charlotte Amalie East 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 East 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 East?

Some of our most popular private pool vacation rentals in Charlotte Amalie East 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 East?

Wander offers 25 private pool vacation rentals in Charlotte Amalie East, 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 East?

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

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

Yes. Every Wander home in Charlotte Amalie East 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.