Luxury Vacation Rentals with a Private Pool in Red Hook

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 Red Hook

Turquoise Dreams (WG1722)

2 bedrooms•2 baths

•

~$110 less than other sites

Luxury

Ruby Ridge

4 bedrooms•4 baths

•

~$350 less than other sites

Skyline Sunshine

3 bedrooms•3 baths

•

~$210 less than other sites

Pineapple Village 3208

2 bedrooms•3 baths

•

~$105 less than other sites

Villa Harmony

5 bedrooms•3 baths

•

~$360 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

Almost Heaven (WG1422)

2 bedrooms•2 baths

•

~$80 less than other sites

Welcome to private poolside luxury in Red Hook

Choose luxury private-pool vacation rentals in Red Hook, VI that pair hotel-grade polish with the privacy of a stunning home. Wander selects only standout residences with inspired design, panoramic seascapes, and immaculate operations, so your arrival matches the photos every time.

Swim in your own pool from sunrise to starlight, recharge in plush bedrooms, and cook in sleek, fully equipped kitchens. Expect ultra fast WiFi, dedicated spaces for work and wellness, smart home controls, pristine cleaning, and 24/7 concierge service. From contemporary coastal villas to serene hillside escapes, every detail is optimized for effortless living and elevated moments.

Available soon in Red Hook

Turquoise Dreams (WG1722)

2 bedrooms•2 baths

•

~$110 less than other sites

Luxury

Ruby Ridge

4 bedrooms•4 baths

•

~$350 less than other sites

Pineapple Village 3208

2 bedrooms•3 baths

•

~$105 less than other sites

Villa Harmony

5 bedrooms•3 baths

•

~$360 less than other sites

CalypsoBlu

3 bedrooms•3 baths

•

~$235 less than other sites

Almost Heaven (WG1422)

2 bedrooms•2 baths

•

~$80 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

Featured private pool vacation rentals in Red Hook

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

St. Sheridan Island

5 bedrooms•5 baths

•

~$520 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

Luxury

Windsong

6 bedrooms•6 baths

•

~$1,000 less than other sites

Highlights in Red Hook

Discover Red Hook, a vibrant coastal hub offering bustling marinas, pristine white-sand beaches, and seamless ferry access to nearby islands.

American Yacht Harbor

Red Hook Ferry Terminal

Sapphire Beach

Lindquist Beach (Smith Bay Park)

Coral World Ocean Park

Coki Beach

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 Red Hook

Turquoise Dreams (WG1722)

2 bedrooms•2 baths

•

~$110 less than other sites

Luxury

Ruby Ridge

4 bedrooms•4 baths

•

~$350 less than other sites

Skyline Sunshine

3 bedrooms•3 baths

•

~$210 less than other sites

Pineapple Village 3208

2 bedrooms•3 baths

•

~$105 less than other sites

Villa Harmony

5 bedrooms•3 baths

•

~$360 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

Almost Heaven (WG1422)

2 bedrooms•2 baths

•

~$80 less than other sites

View all homes

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Discover more beyond the pool in Red Hook

Set on the east end of St. Thomas, Red Hook blends marina-town buzz with postcard-blue bays. Mornings bring rose-gold sunrises over Pillsbury Sound and St. John; days flow from powdery stretches like Sapphire, Lindquist, and Secret Harbour to charters that skim across protected cays.

With the ferry close, island hopping is easy, and evenings hum with waterfront wine bars, live music, and an effortless energy. Whether your rhythm is reef snorkeling, boutique browsing, or watching yachts glide into American Yacht Harbor, Red Hook keeps everything within reach yet never routine. This is why Wander's luxury private-pool vacation rentals in Red Hook, VI are the perfect choice, whether you're traveling for work or leisure.

FAQs: Vacation Rentals in Red Hook

Why should I book a Wander in Red Hook 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 Red Hook 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 Red Hook?

Some of our most popular private pool vacation rentals in Red Hook include Turquoise Dreams (WG1722), Ruby Ridge, and Skyline Sunshine 3BR. 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 Red Hook?

Wander offers 25 private pool vacation rentals in Red Hook, 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 Red Hook?

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

Do Wander’s private pool vacation rentals in Red Hook have WiFi access?

Yes. Every Wander home in Red Hook 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.