Find Hotels with Connecting Rooms in Wailea, HI

Pick from 9 Wailea Hotels with Connecting Rooms and compare room rates, reviews, and availability. Most hotels are fully refundable.

Wailea Beach Villas
2 outdoor pools, free cabanas, pool umbrellas
Wailea Beach Villas
4.5 star property
9.8 out of 10, Exceptional, 154 reviews
"Incredible! Excellent from start to finish!"
Wailea Beach Villas
Four Seasons Resort Maui at Wailea
Club Suite, 1 Bedroom | Egyptian cotton sheets, premium bedding, down comforters, pillowtop beds
Four Seasons Resort Maui at Wailea
5.0 star property
9.6 out of 10, Exceptional, 1,001 reviews
"Great service, great place! "
The price is $995
$1,174 total
includes taxes & fees
Jun 7 - Jun 8
Four Seasons Resort Maui at Wailea
Ho‘olei Villas at Grand Wailea
Outdoor pool, sun loungers
Ho‘olei Villas at Grand Wailea
5.0 star property
9.6 out of 10, Exceptional, 36 reviews
"This is an amazing place to stay with a family. Views. Facilities. Local entertainment, dining, shopping, and activities."
The price is $2,155
$2,601 total
includes taxes & fees
Jun 3 - Jun 4
Ho‘olei Villas at Grand Wailea
Fairmont Kea Lani Maui
View from room
Fairmont Kea Lani Maui
4.5 star property
9.4 out of 10, Exceptional, 1,001 reviews
"Easily some of the best service at any resort we’ve ever stayed. Start to finish everyone was fantastic. Front desk. Valet. Pool. Restaurants. Everyone went above and beyond. Will definitely return. "
The price is $807
$1,011 total
includes taxes & fees
Jun 4 - Jun 5
Fairmont Kea Lani Maui
Andaz Maui at Wailea Resort - a concept by Hyatt
5 outdoor pools, cabanas (surcharge), pool umbrellas
Andaz Maui at Wailea Resort - a concept by Hyatt
4.5 star property
9.2 out of 10, Wonderful, 1,001 reviews
"Absolutely loved our stay at the Andaz!!! One thing we did not enjoy was that it was $50/day for parking which we were not expecting. Breakfast was also $50/day (per person) along with a $50/day resort fee. Seemed like there wasn't much included in the price of the hotel. Overall, a stunning hotel and great service but we will these prices were a little more clear when booking."
The price is $854
$1,066 total
includes taxes & fees
Jun 2 - Jun 3
Andaz Maui at Wailea Resort - a concept by Hyatt
Residence Inn by Marriott Maui Wailea
Property amenity
Residence Inn by Marriott Maui Wailea
3.5 star property
9.2 out of 10, Wonderful, 927 reviews
"Great place to stay! It exceeded our expectations! We will definitely be coming back!"
The price is $519
$612 total
includes taxes & fees
Jun 15 - Jun 16
Residence Inn by Marriott Maui Wailea
Grand Wailea Maui, A Waldorf Astoria Resort
2 bars/lounges, 2 poolside bars, swim-up bar
Grand Wailea Maui, A Waldorf Astoria Resort
5.0 star property
9.0 out of 10, Wonderful, 1,001 reviews
"Best resort in Maui. Views everywhere that are spectacular. Amazing guest experience with fantastic rooms. Pool area was lots of fun and adjacent to the best beach in Wailea! Unbelievable resort. "
The price is $824
$1,030 total
includes taxes & fees
Jun 7 - Jun 8
Grand Wailea Maui, A Waldorf Astoria Resort
Wailea Beach Resort - Marriott, Maui
4 outdoor pools, pool umbrellas, sun loungers
Wailea Beach Resort - Marriott, Maui
4.5 star property
9.0 out of 10, Wonderful, 829 reviews
"The hotel was above expectation. "
The price is $809
$1,019 total
includes taxes & fees
Jun 2 - Jun 3
Wailea Beach Resort - Marriott, Maui
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See all available properties in Wailea
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Price trends for hotels in Wailea

Less expensive
More expensive
This month
Next month
August
January
$349
$375
Month
Price
January
$755
February
$491
March
$440
April
$449
May
$399
June
$349
July
$375
August
$345
September
$367
October
$401
November
$486
December
$425
Price trend information excludes taxes and fees and is based on base rates for a nightly stay for 2 adults found in the last 7 days on our site and averaged for commonly viewed hotels in Wailea. Select dates and complete search for nightly totals inclusive of taxes and fees.

Wailea Hotels with Connecting Rooms information

 

Hotels with Connecting Rooms in Wailea

9

Highest price
$2,155
Cheapest price
$519
Number of guest reviews
5,941
Total number of hotels in Wailea
1,150

 

Frequently asked questions

How much do hotels with connecting rooms in Wailea cost?
You’ll pay from $519 to $2,155 per night for hotels with connecting rooms in Wailea. Whatever your budget, you’ll find the perfect stay on Expedia. This price was available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many hotels with adjoining rooms are there in Wailea?
Wailea has 9 hotels with adjoining rooms. To help you book the perfect digs, use our handy filters to search for other amenities or perks you want.
Are there any family-friendly hotels with connecting rooms in Wailea?
Spend your family vacay at Wailea Beach Villas, A Destination By Hyatt Residence, a 4.5-star option just a quick drive from downtown. Conveniences here include a children’s pool and childcare services. Another family-friendly hotel with connecting rooms is Four Seasons Resort Maui at Wailea. A swimming pool and a nearby beach help make this 5-star stay a traveler favorite. After checking in and chilling out in your comfy digs, it’s time to visit some of the local sights. Hawaiian Islands Humpback Whale Sanctuary Visitor Center and Maui Fish Pipe are among the family-friendly attractions in Wailea.
Why book your hotel with connecting rooms in Wailea with Expedia?
Vacationing with the family should be hassle-free, so if you’re on the lookout for hotels with connecting rooms at a competitive price, Expedia has got your back. Keep costs down and select an all-inclusive resort with connecting rooms, or book a 5-star hotel and pamper your loved ones. Use our convenient search filters to find a stay in Wailea that fits your needs.
How can I find cheap hotels with connecting rooms in Wailea?
Expedia is here to help you search for cheap hotels with connecting rooms in Wailea. To find a superb stay in just a few clicks, simply use our convenient filter tool to refine your search results by star rating, amenities and budget.
What is there to do in Wailea near my hotel with connecting rooms?
Wailea has enough sights and activities to keep you entertained for weeks (or months!), beginning with Wailea Beach. Keawakapu Beach, Makena State Park Beach and Kamaole Beach Park are other terrific attractions. If you’re sticking around a while, Maluaka Beach and Ulua Beach are great additions to your itinerary.

Recent reviews of Wailea hotels
Expedia verified reviews

Wailea Beach Resort - Marriott, Maui

Wailea Beach Resort - Marriott, Maui

5/5 Excellent
"The hotel was above expectation. "
A verified traveler stayed at Wailea Beach Resort - Marriott, Maui
Posted 2 days ago
Wailea Beach Resort - Marriott, Maui