By the Where to Stay in Hawaii editorial team · Updated November 5, 2026
How to Plan Where to Stay
Plan on one base for every four or five nights. Each island change costs about half a day: checking out, returning a car, flying and picking up another car. Where the flights allow, arrive on one island and leave from another, so you don't have to backtrack.
- Two islands: Oʻahu plus one neighbor island, or two neighbor islands such as Maui and the Big Island.
- Two bases on one island: on Maui, the Big Island and Kauaʻi, split your nights between two sides of the island instead of driving back and forth.
7 Days: One Island, Two Bases
- Maui: 4 nights in Kāʻanapali and 3 in Wailea or Kīhei, or the whole week in one of them. Add a night in Hāna if you want to drive the Road to Hāna slowly.
- Big Island: 5 nights on the Kohala Coast or in Kona and 2 in Volcano. Fly into Kona and out of Hilo if the flights work.
- Kauaʻi: 4 nights in Poʻipū and 3 in Princeville, or the week in Kapaʻa.
- Oʻahu: the whole week in Waikīkī, or 5 nights there and 2 on the North Shore.
10 Days: Two Islands
- Oʻahu and Maui (the classic first trip): 3–4 nights in Waikīkī, then 6–7 on Maui, split between West and South Maui if you like. The flight takes about 40 minutes.
- Maui and the Big Island (beaches and the volcano): 5 nights on Maui, 3 on the Kohala Coast or in Kona, and 2 in Volcano.
- Oʻahu and Kauaʻi (city, then hikes and scenery): 3–4 nights in Waikīkī, then 6–7 on Kauaʻi, split between Poʻipū and Princeville. The flight takes 30–45 minutes.
14 Days: Two or Three Islands
- Oʻahu, Maui and Kauaʻi: 3 nights in Waikīkī, 5–6 on Maui and 5 on Kauaʻi.
- Maui and the Big Island, slowly: 7 nights on Maui (two bases plus a night in Hāna), 5 on the Big Island's west coast and 2 in Volcano.
- Oʻahu and the Big Island: 4 nights in Waikīkī, 6 on the Kohala Coast or in Kona and 2–3 split between Volcano and Hilo.
Which Islands to Pair
| Pair | Best for | Flight from Honolulu | Nights |
|---|---|---|---|
| Oʻahu + Maui | First trips: city, then resorts | About 40 min | 3–4 + 6–7 |
| Oʻahu + Kauaʻi | City, then hikes and scenery | 30–45 min | 3–4 + 6–7 |
| Oʻahu + Big Island | City, then the volcano | 45 min–1 hr | 3–4 + 6–7 |
| Maui + Big Island | Beaches and the volcano | Check schedules | 5 + 5 |
One Hotel for Each Stop
One reliable choice per base. Each area guide has splurge and budget alternatives.
Halepuna Waikiki by Halekulani
Helumoa Rd, behind Halekulani, Waikīkī
Our top pick: a calm, polished first stop in Waikīkī, a block from the beach.
Best for: Style without the splurge
- Sister hotel to Halekulani
- Infinity pool with hot tub and cabanas
- Halekulani Bakery on site
More about this hotel
Halekulani's sister hotel stands a block back from the beach, with an infinity pool, hot tub and cabanas and the Halekulani Bakery on site. You get much of the Halekulani polish at a mid-range level, minus the beachfront.
Opens Booking.com with prices for your dates
Photo: Peaceray, CC BY-SA 3.0
Four Seasons Resort Oahu at Ko Olina
Ko ʻOlina, west Oʻahu
Oʻahu alternative: a Ko ʻOlina resort for families who want a resort, not a city.
Best for: Families and couples
- Adults-only pool and quiet beach
- Free kids' club for ages 5–12
- Naupaka Spa & Wellness
More about this hotel
A calm, upscale resort on a Ko ʻOlina lagoon that splits neatly between families and couples: two family pools step down to the beach, and there is a separate adults-only beach area and pool. The kids' club is free for ages 5 to 12.
Opens Booking.com with prices for your dates
Photo: Farragutful, CC BY-SA 4.0
Hyatt Regency Maui Resort & Spa
Kāʻanapali Beach, south end, West Maui
West Maui stop: the big family resort on Kāʻanapali Beach.
Best for: Families and first-timers
- 150-foot lava-tube waterslide
- Sand-bottom keiki lagoon
- Drums of the Pacific lūʻau
More about this hotel
A big resort on 40 acres at the south end of Kāʻanapali Beach, with a half-acre pool, waterfalls, a 150-foot lava-tube slide and a sand-bottom lagoon for small kids. The Drums of the Pacific lūʻau and eight places to eat mean you rarely need the car.
Opens Booking.com with prices for your dates
Photo: Forest and Kim Starr, CC BY 3.0 US
Maui Coast Hotel
South Kīhei Rd, Kamaʻole I, Wailea & Kīhei
South Maui stop: good value across from a Kīhei beach park.
Best for: Value in South Maui
- Across from Kamaʻole Beach Park I
- Pool with free cabanas
- Free shuttle within 3 miles
More about this hotel
A friendly mid-range hotel across the road from Kamaʻole Beach Park I in Kīhei, with free poolside cabanas and a new tower that opened in 2024. A free shuttle covers places within 3 miles.
Opens Booking.com with prices for your dates
Photo: Forest and Kim Starr, CC BY 2.0
Fairmont Orchid
Pauoa Bay, Mauna Lani, Kohala Coast
Big Island west coast stop: a Kohala Coast resort with a snorkeling lagoon.
Best for: An all-round resort base
- 10,000 sq ft oceanfront pool
- Snorkeling lagoon in Pauoa Bay
- Spa Without Walls
More about this hotel
A large resort on the Mauna Lani coast with a 10,000-square-foot oceanfront pool, a protected snorkeling lagoon and the open-air Spa Without Walls. It is about 30 minutes from Kona airport; expect a resort fee and paid parking.
Opens Booking.com with prices for your dates
Photo: Alan Light, CC BY 2.0
Courtyard by Marriott King Kamehameha's Kona Beach Hotel
Kamakahonu Bay, by Kailua Pier, Kona
Big Island value stop: on the beach in Kailua-Kona.
Best for: A walkable town base
- On a small, calm sand beach
- Pool with Billfish Bar & Grille
- Lūʻau on site
More about this hotel
The best-placed hotel in Kailua-Kona town, on the small, swimmable sand beach at Kamakahonu Bay next to the pier. You can walk to Aliʻi Drive restaurants, and there is a pool bar and a lūʻau on site.
Opens Booking.com with prices for your dates
Kilauea Lodge
Old Volcano Rd, Volcano Village
Volcano stop: a night or two near the national park.
Best for: Couples near the volcano
- About a mile from the park entrance
- Fireplaces in several rooms
- Restaurant and covered hot tub
More about this hotel
A cozy 12-room inn in the rainforest about a mile from the park entrance, with gas fireplaces in several rooms, a covered hot tub and its own restaurant. There are no TVs in the rooms and no elevator.
Opens Booking.com with prices for your dates
Photo: Larry D. Moore, CC BY 4.0
Ko'a Kea Resort on Po'ipū Beach
Poʻipū Beach, west end
Kauaʻi south shore stop: right on Poʻipū Beach.
Best for: Couples on the sunny south shore
- Direct access to Poʻipū Beach
- Red Salt restaurant and sushi bar
- Pool with daybeds and spa
More about this hotel
A boutique resort with direct access to Poʻipū Beach, a popular swimming and snorkeling beach, plus the Red Salt restaurant and a spa. Guests must be 21 to check in, though children can stay.
Opens Booking.com with prices for your dates
Photo: E bailey, CC BY-SA 3.0
1 Hotel Hanalei Bay
Puʻu Poʻa point, Princeville, Princeville & Hanalei
Kauaʻi north shore stop: above Hanalei Bay.
Best for: North-shore splurges
- Views over Hanalei Bay
- Three heated pools and Bamford spa
- Seedlings kids' club
More about this hotel
The north shore's big luxury hotel, on Puʻu Poʻa point above Hanalei Bay, with three heated pools, the Bamford Wellness Spa and a kids' club. It reopened on September 28, 2026 after a brief closure for Hurricane Lowell.
Opens Booking.com with prices for your dates
Photo: Tony Webster, CC BY 2.0
Sheraton Kauai Coconut Beach Resort
Coconut Coast, Kapaʻa, Līhuʻe & Kapaʻa
Kauaʻi central stop: a beachfront base between the two shores.
Best for: A central Kauaʻi base
- On the sand
- Infinity pool and kids' splash pad
- Lūʻau on site
More about this hotel
A modern beachfront resort on the Coconut Coast, 10 to 15 minutes from Līhuʻe airport, with an infinity-edge pool, a kids' splash pad and a lūʻau. Its central location makes it easy to reach both Poʻipū and the north shore.
Opens Booking.com with prices for your dates
Photo: Bob Linsdell, CC BY 3.0
Itinerary Hotels at a Glance
Prices change by date and room type, so check your own dates on Booking.com before you decide.
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Halepuna Waikiki by HalekulaniHelumoa Rd, behind Halekulani, Waikīkī · Mid-rangeStyle without the splurgeCheck prices -
Four Seasons Resort Oahu at Ko OlinaKo ʻOlina, west Oʻahu · SplurgeFamilies and couplesCheck prices -
Hyatt Regency Maui Resort & SpaKāʻanapali Beach, south end, West Maui · SplurgeFamilies and first-timersCheck prices -
Maui Coast HotelSouth Kīhei Rd, Kamaʻole I, Wailea & Kīhei · Mid-rangeValue in South MauiCheck prices -
-
Courtyard by Marriott King Kamehameha's Kona Beach HotelKamakahonu Bay, by Kailua Pier, Kona · Mid-rangeA walkable town baseCheck prices -
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Ko'a Kea Resort on Po'ipū BeachPoʻipū Beach, west end · SplurgeCouples on the sunny south shoreCheck prices -
1 Hotel Hanalei BayPuʻu Poʻa point, Princeville, Princeville & Hanalei · SplurgeNorth-shore splurgesCheck prices -
Sheraton Kauai Coconut Beach ResortCoconut Coast, Kapaʻa, Līhuʻe & Kapaʻa · Mid-rangeA central Kauaʻi baseCheck prices
| Hotel | Location | Price level | Best for | Prices | |
|---|---|---|---|---|---|
|
|
Halepuna Waikiki by Halekulani
Boutique hotel
|
Helumoa Rd, behind Halekulani, Waikīkī | Mid-range | Style without the splurge | Check prices |
|
|
Four Seasons Resort Oahu at Ko Olina
Beachfront resort
|
Ko ʻOlina, west Oʻahu | Splurge | Families and couples | Check prices |
|
|
Hyatt Regency Maui Resort & Spa
Beachfront resort
|
Kāʻanapali Beach, south end, West Maui | Splurge | Families and first-timers | Check prices |
|
|
Maui Coast Hotel
Hotel
|
South Kīhei Rd, Kamaʻole I, Wailea & Kīhei | Mid-range | Value in South Maui | Check prices |
|
|
Fairmont Orchid
Beachfront resort
|
Pauoa Bay, Mauna Lani, Kohala Coast | Splurge | An all-round resort base | Check prices |
|
|
Courtyard by Marriott King Kamehameha's Kona Beach Hotel
Beachfront hotel
|
Kamakahonu Bay, by Kailua Pier, Kona | Mid-range | A walkable town base | Check prices |
|
|
Kilauea Lodge
Country inn
|
Old Volcano Rd, Volcano Village | Mid-range | Couples near the volcano | Check prices |
|
|
Ko'a Kea Resort on Po'ipū Beach
Boutique beach resort
|
Poʻipū Beach, west end | Splurge | Couples on the sunny south shore | Check prices |
|
|
1 Hotel Hanalei Bay
Luxury resort
|
Puʻu Poʻa point, Princeville, Princeville & Hanalei | Splurge | North-shore splurges | Check prices |
|
|
Sheraton Kauai Coconut Beach Resort
Beachfront resort
|
Coconut Coast, Kapaʻa, Līhuʻe & Kapaʻa | Mid-range | A central Kauaʻi base | Check prices |
Hotel details checked on November 5, 2026.
Flights Between Islands
There are no passenger ferries between Oʻahu, Maui, the Big Island and Kauaʻi (the only regular ferry links Maui and Lānaʻi), so you fly. From Honolulu (HNL), flights take about 40 minutes to Kahului on Maui, 30–45 minutes to Līhuʻe on Kauaʻi, 45 minutes to an hour to Kona and about an hour to Hilo.
Pick the airport closest to your base: Kona (KOA) for the Big Island's west coast, Hilo (ITO) for Volcano, Kahului (OGG) for Maui and Līhuʻe (LIH) for Kauaʻi. Allow time to return your rental car, and remember that the drive from the airport to your hotel adds 15 minutes to an hour at each end.
Frequently Asked Questions
Quick answers to help you choose where to stay.