Luxury Vacation Rentals in Hawaii

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 221 vacation rentals – enter your dates for availability.

Top-rated vacation rentals in Hawaii

Hale Maluhia Lanikai — Private Pool, Three En-Suite Bedrooms

3 bedrooms•3 baths

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~$1,790 less than other sites

Iconic

Kailua Beach Escape

5 bedrooms•5.5 baths

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New

~$7,660 less than other sites

KP228 Garden View, Beach, Pool, Turtle, AC

1 bedroom•1 bath

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New

~$85 less than other sites

Luxury

Estate Home at Puako Bay (74)

4 bedrooms•4.5 baths

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New

~$815 less than other sites

Iconic

Puako’s Ocean Edge Modern Estate

4 bedrooms•5.5 baths

New

Iconic

Kona Bay Shores

5 bedrooms•6 baths

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~$985 less than other sites

Luxury

HaleGator

3 bedrooms•1.5 baths

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New

~$1,260 less than other sites

Luxury

Wailupe Seaside

4 bedrooms•4 baths

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~$1,405 less than other sites

Welcome to Hawaii

Experience the best of island living with Wander’s luxury vacation rentals in Hawaii. Our handpicked homes in Waimea, Koloa, Kailua-Kona, Kihei, and Princeville bring hotel-level consistency to the most coveted coastlines and upland settings.

Each residence pairs striking design with hotel-grade comforts like chef-ready kitchens, private pools or hot tubs, dedicated work zones, and ultra fast WiFi. Expect pristine housekeeping, plush linens, and 24/7 concierge support so your time on the islands feels effortless.

Whether you are planning a restorative escape or a productive workcation, a Wander makes it simple.

Destinations in Hawaii

Available soon in Hawaii

KP212 Ocean View, AC, Pool, Gym, Two Lanais

2 bedrooms•2 baths

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New

~$150 less than other sites

KP241 Ground & 2nd FL Lanai, Beach, Pool, Gym

2 bedrooms•2 baths

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New

~$140 less than other sites

Beach Walk

2 bedrooms•2 baths

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~$145 less than other sites

Blue Hawaii

3 bedrooms•3.5 baths

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New

~$175 less than other sites

Oceanview Retreat, Walk to Beach & Restaurants

1 bedroom•1 bath

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~$55 less than other sites

KP40 Walk to Beach Top Corner Unit, A/C, Pool, Gym

1 bedroom•1 bath

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New

~$75 less than other sites

Luxe Maui Beach Retreat, Walk to Kamaole Beach

1 bedroom•1 bath

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~$45 less than other sites

Hihimanu House

4 bedrooms•3.5 baths

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~$200 less than other sites

Featured vacation rentals in Hawaii

Iconic

Kailua Beach Escape

5 bedrooms•5.5 baths

•

New

~$7,660 less than other sites

Luxury

Estate Home at Puako Bay (74)

4 bedrooms•4.5 baths

•

New

~$815 less than other sites

Iconic

Puako’s Ocean Edge Modern Estate

4 bedrooms•5.5 baths

New

Iconic

Kona Bay Shores

5 bedrooms•6 baths

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~$985 less than other sites

Luxury

Haena Beach House TVNC#1258

5 bedrooms•5 baths

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~$465 less than other sites

Luxury

Pakui Street Estate (149) at Hualalai Resort

3 bedrooms•3.5 baths

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New

~$930 less than other sites

Luxury

Makani Kai

5 bedrooms•5.5 baths

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New

~$970 less than other sites

Luxury

Mauna Lani Lux Golf Estate (6) at One Ocean

6 bedrooms•6.5 baths

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New

~$890 less than other sites

Highlights in Hawaii

Explore a vibrant Pacific paradise of active volcanoes, legendary surf breaks, lush rainforests, and profound Polynesian cultural heritage across the islands.

Hawaiʻi Volcanoes National Park

Pearl Harbor National Memorial

Waikīkī Beach

Nā Pali Coast State Wilderness Park

Haleakalā National Park

Road to Hāna

Waimea Canyon State Park

Mauna Kea Summit

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 Hawaii

Hale Maluhia Lanikai — Private Pool, Three En-Suite Bedrooms

3 bedrooms•3 baths

•

~$1,790 less than other sites

Iconic

Kailua Beach Escape

5 bedrooms•5.5 baths

•

New

~$7,660 less than other sites

KP228 Garden View, Beach, Pool, Turtle, AC

1 bedroom•1 bath

•

New

~$85 less than other sites

Luxury

Estate Home at Puako Bay (74)

4 bedrooms•4.5 baths

•

New

~$815 less than other sites

Iconic

Puako’s Ocean Edge Modern Estate

4 bedrooms•5.5 baths

New

Iconic

Kona Bay Shores

5 bedrooms•6 baths

•

~$985 less than other sites

Luxury

HaleGator

3 bedrooms•1.5 baths

•

New

~$1,260 less than other sites

Luxury

Wailupe Seaside

4 bedrooms•4 baths

•

~$1,405 less than other sites

View all homes

Most popular amenities for vacation rentals in Hawaii

More popular destinations in Hawaii

Other popular amenities & vacation types in Hawaii

Family vacation rentals in Hawaii

Large group vacation rentals in Hawaii

Beachfront vacation rentals in Hawaii

Hot tub vacation rentals in Hawaii

Private pool vacation rentals in Hawaii

Discover more of Hawaii

Hawaii rewards discerning travelers with distinct landscapes and microclimates across Kauai, Maui, and the Island of Hawaii. Princeville and Koloa reveal Kauai’s dramatic North and South Shores, from emerald ridgelines to calm coves perfect for unhurried days by the water.

On Maui, Kihei brings warm, dry weather and easy access to coastal adventures. On Hawai‘i Island, Kailua-Kona blends oceanfront buzz with coffee country, while Waimea offers cooler highland vistas and brilliant night skies.

With such variety in scenery, climate, and pace, this is why Wander's luxury vacation rentals in Hawaii are the perfect choice, whether you're traveling for work or leisure.

FAQs: Vacation Rentals in Hawaii

Why should I book a Wander in Hawaii over other vacation rentals?

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

Every home in Hawaii 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 vacation rentals in Hawaii?

Some of our most popular vacation rentals in Hawaii include Hale Maluhia Lanikai — Private Pool, Three En-Suite Bedrooms, Kailua Beach Escape, and KP228 Garden View | Beach•Pool•Turtle•AC. 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 vacation rentals does Wander have available in Hawaii?

Wander offers 221 vacation rentals in Hawaii, 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 vacation rentals in Hawaii?

You can check-in to Wander vacation rentals in Hawaii after 4.00pm and check-out before 10.00am.

Do Wander’s vacation rentals in Hawaii have WiFi access?

Yes. Every Wander home in Hawaii 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.