Paia Holiday Rentals

  • Plan, book, stay with confidence
    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Holiday Rentals in Paia

Aston Kaanapali Shores
Exterior

Aston Kaanapali Shores

3.5 star property
8.6 out of 10, Excellent, (3350)
"We had an excellent time staying three nights at the Aston! We ate at the restaurant and it was great. The amenities are great and the staff went above and beyond our expectations. We used the concierge for booking a luau and it was fantastic. Five stars all around! "
The price is HK$2,522
HK$3,204 total
includes taxes & fees
24 Nov - 25 Nov
Aston Kaanapali Shores
OUTRIGGER Honua Kai Resort & Spa
4 outdoor pools, open 8:00 AM to 10:00 PM, pool cabanas (surcharge)

OUTRIGGER Honua Kai Resort & Spa

4.0 star property
8.8 out of 10, Excellent, (2627)
"Nice and smooth experience. I recommend it!"
The price is HK$1,713
HK$6,143 total
includes taxes & fees
8 Dec - 9 Dec
OUTRIGGER Honua Kai Resort & Spa
The Westin Ka'anapali Ocean Resort Villas
2 outdoor pools, pool umbrellas

The Westin Ka'anapali Ocean Resort Villas

4.0 star property
8.6 out of 10, Excellent, (1080)
"Loved the shuttle to whalers village. Had to request housekeeping service twice during our stay as our room was missed ?"
The price is HK$3,728
HK$4,398 total
includes taxes & fees
29 Nov - 30 Nov
The Westin Ka'anapali Ocean Resort Villas
Aston Maui Kaanapali Villas
Exterior

Aston Maui Kaanapali Villas

3.0 star property
8.6 out of 10, Excellent, (2300)
"The Exterior property was A little dated. But the interior rooms were Updated and very clean. The garden area with plants and adorable little cats running around, making sure there were no “pests” around was beautifully manicured. We had a wonderful time. Would visit and stay there again."
The price is HK$2,421
HK$3,452 total
includes taxes & fees
24 Nov - 25 Nov
Aston Maui Kaanapali Villas
Kaanapali Alii
3 outdoor pools, pool loungers

Kaanapali Alii

4.0 star property
9.6 out of 10, Exceptional, (838)
"It needs a bar"
Kaanapali Alii
Aston Mahana at Kaanapali
Outdoor pool

Aston Mahana at Kaanapali

3.5 star property
9.0 out of 10, Wonderful, (1574)
"We love this place. We stay here to relax and enjoy the view. Also the staff is wonderful!"
Aston Mahana at Kaanapali
The Whaler Resort Kaanapali Beach
Exterior

The Whaler Resort Kaanapali Beach

4.0 star property
9.4 out of 10, Exceptional, (118)
"Would recommend this location to anyone reading this"
The Whaler Resort Kaanapali Beach
Sugar Beach Resort
Outdoor pool

Sugar Beach Resort

3.0 star property
8.6 out of 10, Excellent, (1022)
"The beach was in your backyard. I’ve seen multiple turtles. There’s a cute delicious deli on the property. Away from the busy areas but close enough for a short drive. Just a perfect getaway "
Sugar Beach Resort
Napili Shores Maui by OUTRIGGER
On the beach

Napili Shores Maui by OUTRIGGER

3.0 star property
8.8 out of 10, Excellent, (1533)
"Can’t say enough good things about Napili Shores to stay will definitely be back"
Napili Shores Maui by OUTRIGGER
Maui Beach Vacation Club
Living area

Maui Beach Vacation Club

2.5 star property
8.2 out of 10, Very good, (699)
"Great!"
Maui Beach Vacation Club
Aston Maui Hill
Outdoor pool, open 8:00 AM to 9:30 PM, pool loungers

Aston Maui Hill

3.0 star property
9.0 out of 10, Wonderful, (752)
"The apartment was beautifully decorated. Very clean. The grounds lovely, and a short distance to a strip of beach. The pool was closed for renovation, which was disappointing, as it looked beautiful and to be a respectable size. Monday night happy hour with all residents was a wonderful. treat. Drinks and food! We were the youngest in the crowd at 30's and 50's.The beds were comfortable. The kitchen has no oven and was not well equipped; we figured it out. Truly a nice place. This is located at...
Aston Maui Hill
Castle Napili Surf Beach Resort
On the beach, white sand

Castle Napili Surf Beach Resort

3.5 star property
10.0 out of 10, Exceptional, (78)
"We had a great stay at the Napili Surf Resort. We travel with seniors and kid. The staff are helping and welcolmeing. Everybody is happy. The full kitchen gave us additional option for food. There are 2 restaurants on the beach and Napili market is around the corner. And the resort was very quiet after 8 or 9pm. There are not so many people crowed down on the beach so we enjoyed a calm and relaxed time on the beach either. We will definitely come back. "
Castle Napili Surf Beach Resort
Aston at The Whaler on Kaanapali Beach
Outdoor pool, open 8:00 AM to 10:00 PM, pool cabanas (surcharge)

Aston at The Whaler on Kaanapali Beach

4.0 star property
9.2 out of 10, Wonderful, (1447)
"We loved our time at the Whaler however our room needed an upgrade as it looked like it was from the 80’s. Everything else perfect. Staff wonderful!!"
The price is HK$1,792
HK$5,053 total
includes taxes & fees
29 Nov - 30 Nov
Aston at The Whaler on Kaanapali Beach
Napili Sunset on the Beach
Sun deck

Napili Sunset on the Beach

2.5 star property
9.2 out of 10, Wonderful, (600)
"Very Nice Soot! Cozy!"
The price is HK$1,776
HK$2,095 total
includes taxes & fees
24 Nov - 25 Nov
Napili Sunset on the Beach
Aston at Papakea Resort
Outdoor pool

Aston at Papakea Resort

3.0 star property
8.2 out of 10, Very good, (1353)
"Originally we were checked into a smaller 3rd story room when we believed we were supposed to have a different ground floor. We advised them at check in, and though we would have still had a great vacation in this room, the management quickly remedied the situation and made our stay so much more pleasant. Everyone was so kind and gracious. The property and stay were perfect!"
Aston at Papakea Resort
Maui Sunset
View from property

Maui Sunset

3.5 star property
8.8 out of 10, Excellent, (403)
"The pool and the location of the proximity to the rims was very good also the proximity to Beach and the view of the ocean was very nice and the proximity to shopping and dining was very good also the only thing we did not really like is the size of the restrooms and the updating of the restrooms were not very good and they should be renovated "
Maui Sunset
Wailea Ekahi - CoralTree Residence Collection
Exterior

Wailea Ekahi - CoralTree Residence Collection

3.0 star property
9.2 out of 10, Wonderful, (494)
"Beautiful condo"
Wailea Ekahi - CoralTree Residence Collection
Kapalua Villas Maui
In-room safe, individually decorated, individually furnished

Kapalua Villas Maui

4.0 star property
8.6 out of 10, Excellent, (910)
"Loved the property and location. Only issue is that eating establishments are somewhat limited in variety and price and most require advance reservations. I found I would drive to kanapali for more options"
The price is HK$1,590
HK$6,067 total
includes taxes & fees
12 Dec - 13 Dec
Kapalua Villas Maui
Maui Kamaole
Exterior

Maui Kamaole

3.5 star property
8.8 out of 10, Excellent, (819)
"Beautiful time as usual…"
Maui Kamaole
The Gardens at West Maui
Iron/ironing board, free WiFi

The Gardens at West Maui

3.0 star property
8.4 out of 10, Very good, (436)
"Lisa at the front desk was so friendly, helpful and a delight, really enjoyed this property. Would recommend it too others."
The Gardens at West Maui
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.
Don't see what you're looking for?
See all available properties in Paia
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other types of properties in Paia you may be interested in

Paia Inn
Exterior

Paia Inn

3.5 star property
9.0 out of 10, Wonderful, (276)
"Place was great. In the center of Paia"
The price is HK$2,327
HK$3,098 total
includes taxes & fees
27 Nov - 28 Nov
Paia Inn
Fairmont Kea Lani Maui
View from room

Fairmont Kea Lani Maui

4.5 star property
9.4 out of 10, Exceptional, (1010)
"Everything was excellent. The people are incredibly friendly, and the ambiance is outstanding. The location is also conveniently close to shopping and dining areas in Wailea. However, the pool and resort were a bit too quiet—I would have enjoyed some lively music by the pool."
The price is HK$4,426
HK$5,680 total
includes taxes & fees
1 Dec - 2 Dec
Fairmont Kea Lani Maui
Aston Kaanapali Shores
Exterior

Aston Kaanapali Shores

3.5 star property
8.6 out of 10, Excellent, (3350)
"We had an excellent time staying three nights at the Aston! We ate at the restaurant and it was great. The amenities are great and the staff went above and beyond our expectations. We used the concierge for booking a luau and it was fantastic. Five stars all around! "
The price is HK$2,522
HK$3,204 total
includes taxes & fees
24 Nov - 25 Nov
Aston Kaanapali Shores
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.
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until December 4 with our Black Friday deals. Stay by December 15, 2025.
Unlock Black Friday deals

Frequently asked questions

Can I find a holiday rental in Paia?

Yes, there are holiday rentals close to the most popular sights in Paia, or you can select a more secluded option if you're looking for a relaxing stay. Visitors to Paia speak positively about the beaches and seafood restaurants in this destination. Make sure you have time to check out the live music and theatres during your trip.

What are some of the best holiday rentals that Paia has to offer?

The #1 Luxury OCEAN FRONT Mansion! Sleeps 32: This holiday home rental outside of Paia is located on the beach, and has an outdoor pool, a balcony and a BBQ to put you at ease in your new surroundings. It has 11 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games.

How many holiday rentals are there in Paia?

With 25 Expedia holiday rentals, you're guaranteed to find just the right place for your Paia stay.

What’s there to see and do in Paia?

H.A. Baldwin Beach State Park and Paia Bay are a couple of lovely local spots to get outside and enjoy nature. While here, Kuau Bay Beach and Hookipa Beach Park are other places worth a visit.

What’s a holiday rental in Paia like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Paia. Holiday rentals provide amenities such as hot tubs, fire pits and patios so you'll have a home away from home. If you're concerned about cleanliness, holiday rentals can provide a sense of safety away from shared hotel lifts and bustling concierge desks while still allowing you the excitement and enjoyment of travel. You'll also have more space in a holiday rental than in a standard hotel, which makes a holiday rental a great option for a family trip.