Hand-picked Hawaii vacation rentals & condosEvery view checked
Breakfast on a lanai overlooking the ocean in Hawaii
The HawaiiGaga island guide

Which Hawaiian island is best? Start with where you'll wake up.

Your accommodation choice shapes your entire vacation. It's where you spend most of your time: coffee on the lanai, the walk to the beach, sunset from the balcony, afternoons at the pool. Below, we compare the twelve places where almost every visitor stays. Find the morning you want, and the island chooses itself.

Will the weather decide it for you?

Probably not. Hawaii arguably has the best weather in the world. It's in the low 80s by day and around 70 at night almost everywhere, all year. What changes from place to place is rain, and that is predictable: the trade winds drop it on the mountains on north and east-facing shores.

Most places to stay are on the dry, sunny coasts. Weather only really matters if you're going to Kauai in winter (choose Poipu) or you want the surest sunshine (the Kohala Coast, Kona, Kaanapali, Ko Olina, Wailea and Kihei).

Our numbers count only the best

When this guide says Kaanapali has 768 condos, it means 768 that made our list: well reviewed by real guests, properly licensed, and with every ocean view and beachfront label checked by us. Hawaii has many more vacation rentals - the counts and prices below come from the ones that made the grade.

Maui
Island 1 of 4

Maui

The island people fall for first

Maui has, by far, the most beachfront accommodations of any Hawaiian island, all situated along its sunny west and south shores. Combine that with its diverse landscapes - Haleakala and the Hana region, and plenty of activities, and you have a perfect vacation destination. West Maui is greener and more dramatic. South Maui is drier, sunnier and closer to the airport.

4,482 hand-picked places to stayFour areas on two sunny coastsHumpback whales December to April

Lahaina town is still rebuilding after the 2023 fire. Kaanapali and Kapalua, just up the coast, were not damaged.

Where you'll stay on Maui: Kaanapali, Kapalua and Napili, Kihei, Wailea
Our full guide to where to stay in Maui →
Kaanapali from the air
Maui

Kaanapali

The classic Hawaii resort beach, with everything a stroll away.

A day in Kaanapali

Morning coffee on the lanai, with the beach already glowing below. You swim before breakfast, then follow the beachfront path to Whalers Village for lunch. In the afternoon, snorkel at Black Rock and look for sea turtles. At sunset a cliff diver lights the torches on the rock and leaps into the sea, and dinner is a short walk away.

Black Rock, on Kaanapali Beach
Black Rock, on Kaanapali Beach
Next door, for less: Honokowai and Kahana

Just north of Kaanapali, 27 oceanfront condo complexes line the same coast, with 75% featuring oceanviews. Most nights cost $340 to $570. Guests here mention whales in 1 in 8 reviews and sea turtles in 1 in 6.

See West Maui rentals →
Kapalua and Napili from the air
Maui

Kapalua and Napili

Sheltered bays, snorkeling from the sand and a slower pace.

A day in Kapalua and Napili

You wake to birdsong and the rustle of palms. Mornings are spent walking the lovely costal trail, with a snorkel at Kapalua Bay or swim at Napili Bay. Spend the evening on the lanai, watching the sun sink beside the island of Molokai.

Napili Bay
Napili Bay
Kihei from the air
Maui

Kihei

Sunny, easygoing and the best value on Maui.

A day in Kihei

Sunshine is almost a given. Cross the road to the Kamaole beaches for a morning swim, then grab fish tacos from a food truck. Trade winds pick up in the afternoons but you're exploring the island's attractions - 'Iao Valley, Haleakala, Pa'ia town and Twin Falls. Evenings are relaxed: a beach-bar sunset with Kahoolawe and Lanai on the horizon.

Kamaole Beach Park I
Kamaole Beach Park I
Wailea from the air
Maui

Wailea

Polished, peaceful and made for long, slow days.

A day in Wailea

Wailea runs on a gentle rhythm. Swim at Ulua Beach while the water is still glassy, then walk the coastal path that links five crescent beaches. Spend the afternoon by the pool, or play a round of golf. At sunset, the Shops at Wailea and some of Maui's best restaurants are minutes away.

Ulua Beach
Ulua Beach

Beyond your door on Maui

The big days out, wherever you stay.

Haleakala: above the clouds

Haleakala: above the clouds

Watch the sun rise over a sea of clouds from 10,000 feet, or skip the 3 a.m. alarm and go for sunset.

About 1.5 hours from Wailea and Kihei, 2 from Kaanapali. Sunrise needs a park reservation.

The Road to Hana

The Road to Hana

A full day of waterfalls, bamboo forest and black-sand beaches, around some 600 curves. The Pipiwai Trail's bamboo forest is a highlight.

Leave early, and book Waianapanapa State Park ahead.

Molokini Crater

Molokini Crater

Snorkel inside a sunken volcanic crater, where the water is famously clear.

Morning boats leave from Maalaea and Kihei.

Whale season

Whale season

Thousands of humpbacks spend the winter in Maui's warm, shallow waters. You'll see them from boats, beaches and probably your lanai.

December to April, best January to March.

Maui is for you if…

  • you want the classic Hawaii beach vacation, with water calm enough to swim
  • it's your first trip and you want a little of everything
  • you're coming in winter and want to see whales

Stay in Kaanapali for convenience, Kapalua for quiet, Wailea for polish, or Kihei for value.

Kauai
Island 2 of 4

Kauai

The Garden Isle, wild and green

Kauai is the island that makes people go quiet. Waterfalls stream down green cliffs, chickens wander the roadsides, and nothing is built taller than a palm tree. There's no city and no rush, and the Napali Coast is so wild that no road goes around the island. It rains more here than on the other islands, which is exactly why Kauai looks the way it does.

1,686 hand-picked places to stay340 vacation homes, the most in HawaiiNo road around the island
Where you'll stay on Kauai: Princeville and Hanalei, Kapaa and Wailua, Poipu
Our full guide to where to stay in Kauai →
Princeville and Hanalei from the air
Kauai

Princeville and Hanalei

Mountains, waterfalls and Hawaii's most dramatic views.

A day in Princeville and Hanalei

From your clifftop lanai, the peak called Bali Hai rises across Hanalei Bay, and after a night shower waterfalls thread down the mountains. Have breakfast in Hanalei town and a swim in the bay, then drive over one-lane bridges to the end of the road. Get back in time for the sunset that made Princeville famous.

Hanalei Pier
Hanalei Pier
Kapaa and Wailua from the air
Kauai

Kapaa and Wailua

Sunrises over the ocean, a seaside bike path and the middle of everything.

A day in Kapaa and Wailua

Set an alarm you'll be glad about: the sun rises straight out of the ocean in front of you. Rent a bike and ride the coastal path past quiet coves, then browse Old Kapaa town and its food trucks. In the afternoon, kayak the Wailua River to a waterfall. Both ends of the island are about an hour away.

Lydgate Beach Park
Lydgate Beach Park
Poipu from the air
Kauai

Poipu

Kauai's sunny side, with calm water and sea turtles.

A day in Poipu

Poipu is where Kauai relaxes. Sea turtles graze in the shallows, and a Hawaiian monk seal may be napping on the sand at Poipu Beach Park. Snorkel in the calm, reef-protected water, walk the sea cliffs of the Mahaulepu trail, then watch Spouting Horn blow on your way to dinner.

Poipu Beach Park
Poipu Beach Park

Beyond your door on Kauai

The big days out, wherever you stay.

The Napali Coast

The Napali Coast

See 17 miles of sea cliffs from a boat, or fly over the waterfalls that only birds usually see.

Boats sail all year, and the sea is calmest in summer.

Waimea Canyon

Waimea Canyon

A red-and-green canyon more than 3,000 feet deep, with lookouts you can drive right up to.

About an hour from Poipu, two hours from Princeville.

The Kalalau Trail

The Kalalau Trail

Hawaii's most famous hike climbs the Napali cliffs to a hidden beach two miles in.

Book a Haena State Park reservation first. Spots go fast.

Waterfalls near Wailua

Waterfalls near Wailua

Kayak up the Wailua River and hike to a waterfall, or drive to Wailua and Opaekaa Falls in minutes.

Ten minutes from Kapaa.

Kauai is for you if…

  • scenery matters more to you than nightlife
  • you love hiking, waterfalls and being outdoors
  • you'd like a whole house rather than a condo

Stay in Princeville and Hanalei for summer drama, in Poipu for sun and swimming, or in Kapaa for value and sunrises.

Oahu
Island 3 of 4

Oahu

Three trips on one island

Oahu is the easy island, with the most flights, the most to do and the best food. Most people think only of Waikiki, but Oahu's places to stay are three very different trips: city life in Waikiki, calm resort lagoons at Ko Olina, and the wild North Shore at Turtle Bay. Vacation rentals are only allowed in a few resort areas here, so these three are your choices.

1,163 hand-picked places to stayNo car needed in WaikikiPearl Harbor 30 minutes from Waikiki
Where you'll stay on Oahu: Waikiki, Ko Olina, Turtle Bay
Waikiki from the air
Oahu

Waikiki

The world's most famous beach, with the city at your door.

A day in Waikiki

Step out the door and you're in it: a surf lesson on gentle waves, the walk up Diamond Head, and shave ice on Kalakaua Avenue. Lunch can be anything from a poke bowl to a chef's tasting menu. After sunset there's live music, rooftop bars and the city lights shining along the shore.

Waikiki Beach
Waikiki Beach
Ko Olina from the air
Oahu

Ko Olina

Four calm lagoons and easy resort living on Oahu's sunny west side.

A day in Ko Olina

The lagoons are the magic here: four sheltered, sandy coves where the water barely ripples. Kids paddle while you read in the shade. Walk the path from lagoon to lagoon, snorkel the rocks for turtles, then watch a sunset that turns the whole sky orange. Honolulu is 40 minutes away when you want the city.

One of Ko Olina's four lagoons
One of Ko Olina's four lagoons
Turtle Bay from the air
Oahu

Turtle Bay

Big waves, sea turtles and the slow pace of the North Shore.

A day in Turtle Bay

Wake up to the sound of the North Shore. In winter, watch the world's best surfers ride giant waves a few miles down the coast. In summer the sea turns calm and clear. Swim with turtles in the cove, ride horses along the beach, then stop at the Kahuku shrimp trucks on the way to Haleiwa for shave ice.

Turtle Bay
Turtle Bay

Beyond your door on Oahu

The big days out, wherever you stay.

Pearl Harbor

Pearl Harbor

Stand above the USS Arizona, then walk the decks of the battleship Missouri.

Memorial tickets are free but go fast, so book ahead. 30 minutes from Waikiki.

Diamond Head

Diamond Head

A short, steep climb to the crater rim, with the best view of Waikiki.

1.6 miles round trip. Visitors need a reservation.

The North Shore

The North Shore

From November to February, giant swells roll in and the pros surf Waimea Bay and Pipeline. In summer the same beaches are calm enough to swim.

About an hour from Waikiki, minutes from Turtle Bay.

Hanauma Bay

Hanauma Bay

Snorkel a sheltered bay inside an old volcanic crater, full of reef fish.

20 minutes from Waikiki. Reservations required.

Oahu is for you if…

  • you want lots to see and do, and great food
  • you'd rather not rent a car
  • you want the best value in Hawaii

Stay in Waikiki for the city, Ko Olina for calm lagoons, or Turtle Bay for the North Shore.

Big Island
Island 4 of 4

Big Island

Sunshine, lava and room to roam

The Big Island is bigger than all the other Hawaiian islands put together, and it feels like it: black lava fields, snow on the summits in winter, rainforest valleys and an active volcano. Both places to stay sit on its sunny west coast, the driest in Hawaii. Come for sunshine you can count on, and for adventures you can't have anywhere else.

1,767 hand-picked places to stayThe sunniest coast in HawaiiAn active volcano
Where you'll stay on Big Island: Kona, Kohala Coast
Kona from the air
Big Island

Kona

Oceanfront sunsets, coffee farms and the best snorkeling in Hawaii.

A day in Kona

Your lanai sits right above the waves, and spinner dolphins sometimes pass by in the morning. Snorkel with turtles at Kahaluu Bay, taste coffee on a farm up the hill, then stroll the seawall along Alii Drive. After dark, take a boat out to snorkel with giant manta rays.

Kahaluu Bay
Kahaluu Bay
Kohala Coast from the air
Big Island

Kohala Coast

White-sand beaches in a sea of black lava, and sun almost every day.

A day in Kohala Coast

It hardly ever rains here. Spend the morning on Hapuna or Mauna Kea Beach, two of the finest in Hawaii, then laze by a resort-style pool. Walk among ancient petroglyphs, tee off on a golf course framed by lava, and end the day with a sunset dinner and a sky full of stars.

Mauna Kea Beach
Mauna Kea Beach

Beyond your door on the Big Island

The big days out, wherever you stay.

Hawaii Volcanoes National Park

Hawaii Volcanoes National Park

Since December 2024, Kilauea has erupted in bursts, sometimes with lava fountains you can see from the overlooks. Hike across the floor of Kilauea Iki crater.

About 2.5 hours from Kona. Check the park's eruption updates before you go.

Snorkel with manta rays

Snorkel with manta rays

After dark, boats from Kona take you out where giant manta rays glide and somersault beneath you.

Night tours leave from the Kona coast.

Mauna Kea at sunset

Mauna Kea at sunset

Tours drive you to 13,800 feet for sunset, then stop lower down for some of the clearest stargazing on Earth.

Tours run from Kona and the Kohala Coast.

Pololu Valley

Pololu Valley

Drive north past horse ranches to a lookout over sea cliffs, then hike down to a black-sand beach.

About an hour from the Kohala Coast.

Big Island is for you if…

  • you want sunshine you can count on
  • you love snorkeling, and nature on a grand scale
  • you're curious to see a volcano for yourself

Stay on the Kohala Coast for beaches and sun, or in Kona for snorkeling, value and town life.

Still torn? Start with what matters most

One island or two?

We recommend one island and one location if you're staying for just a week. With two weeks you can either split your stay on the same island, or do two islands. There are no ferries between the islands and you lose a full day when island hopping.

Featured

Special offers on places to stay

Beachfront Condo
Privacy and Seclusion

Beachfront Condo

Unparalleled views with a top notch beach steps away

South Kihei Condo
Ocean View Suite

South Kihei Condo

Special rates - fully renovated 1 bedroom condo.

Steps From Poipu Beach
Beach Getaway

Steps From Poipu Beach

Romantic 1 Bedroom Condo at Manualoha at Poipu Kai.

Found your place?

Every place to stay we list is hand-picked: well reviewed, licensed, and with its ocean view checked by us.

About these numbers: places to stay and nightly prices are counted from the vacation rentals we list (October 2026); the price range covers the middle half of nightly rates. Rainfall is the annual average from our weather guide. Review comparisons look at guest reviews since 2019 across all twelve areas. Molokai and Lanai are lovely and quiet, but have few places to stay and are usually a second trip.