Holiday Homes in South Maui

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Check prices for these dates

Next weekend
28 Feb - 2 Mar
In two weeks
7 Mar - 9 Mar
In one month
21 Mar - 23 Mar
In two months
18 Apr - 20 Apr

Featured Holiday Homes in South Maui

Maui Sunset Resort A102 - Aloha Mai, Remodel, Ground floor, 1BR/2BA, Sleeps 5, A
Pool

Maui Sunset Resort A102 - Aloha Mai, Remodel, Ground floor, 1BR/2BA, Sleeps 5, A

9.6 out of 10, Exceptional, (93)
"Had a wonderful 7 days in Kihei - this place was great. Loved that you could walk the beautiful beach, the grounds were very well maintained, the pool was delightful and my husband was able to walk to the city park and play pickleball every morning. "
Maui Sunset Resort A102 - Aloha Mai, Remodel, Ground floor, 1BR/2BA, Sleeps 5, A
Spacious Family Beach House with Large Heated Pool; walk to Beach 🏖
Outdoor dining

Spacious Family Beach House with Large Heated Pool; walk to Beach 🏖

10.0 out of 10, Exceptional, (127)
"Had a blast. "
Spacious Family Beach House with Large Heated Pool; walk to Beach 🏖
Stunning Beachfront Private Home! Perfect for Families, Great Location!
On the beach

Stunning Beachfront Private Home! Perfect for Families, Great Location!

9.8 out of 10, Exceptional, (93)
"11 family members stayed at this property. Beautiful yard, view of ocean, access to beach, great location."
Stunning Beachfront Private Home! Perfect for Families, Great Location!
Tropical Gated Oceanfront Estate, Pool, Privacy, and huge ocean view on 2/3 acre
On the beach, sun-loungers, beach towels

Tropical Gated Oceanfront Estate, Pool, Privacy, and huge ocean view on 2/3 acre

9.8 out of 10, Exceptional, (192)
"We were a family of eight adults and six children ages seven and under. The pool and yard were amazing. We used all of the open areas inside and out but really loved the huge covered lanai. We also rented the Ohana unit for one of our little families. They appreciated the quiet down there. Note that you must go outside to reach it, but we didn’t mind. House was very well stocked with beach towels/regular towels and paper products. The beach is so convenient and undeveloped. We rented wagons and...
Tropical Gated Oceanfront Estate, Pool, Privacy, and huge ocean view on 2/3 acre
Island Retreat Spacious 3B/3B Wailea Home Ocean View Private Pool & Hot Tub!
Pool

Island Retreat Spacious 3B/3B Wailea Home Ocean View Private Pool & Hot Tub!

9.8 out of 10, Exceptional, (138)
"We had an amazing time at this vacation rental! Right from the start, we were blown away by how clean, spacious, and well-equipped the house was. It looked just like the photos and description on VRBO. The kitchen had everything we needed to whip up our meals, and the living areas were perfect for the whole family. The deck with the hot tub was a fantastic way to unwind after a long day at the beach, and the sunset views were just incredible. We even caught some fireworks from the Grand Wailea...
Island Retreat Spacious 3B/3B Wailea Home Ocean View Private Pool & Hot Tub!
Blue Sky Escapes Vacation Home w/ big Oceanviews, Pool, Jacuzzi, 5min to beach
Property grounds

Blue Sky Escapes Vacation Home w/ big Oceanviews, Pool, Jacuzzi, 5min to beach

9.8 out of 10, Exceptional, (79)
"The front door was almost impossible to unlock. WE had to have the owner come twice to try to fix it. He decided that we should leave it unlocked when we were away since the key wouldn't work. It caused a lot of stress."
Blue Sky Escapes Vacation Home w/ big Oceanviews, Pool, Jacuzzi, 5min to beach
4-bedroom mini-splits AC vacation home just 5 minutes drive to Wailea Beach

4-bedroom mini-splits AC vacation home just 5 minutes drive to Wailea Beach

10.0 out of 10, Exceptional, (56)
"This was our first trip to Maui. Linda was very attentive and sent us multiple recommendations so that we could have an idea of things we wanted to do prior to our stay. Having access to the pool was very nice as well for the evenings we wanted to continue relaxing in the water without the beach. We highly recommend this property and would love to rent it again in the future!! "
4-bedroom mini-splits AC vacation home just 5 minutes drive to Wailea Beach
Spacious Maui Beach House, Private Pool, AC, Sleeps 6
Beach nearby, sun-loungers, beach towels

Spacious Maui Beach House, Private Pool, AC, Sleeps 6

10.0 out of 10, Exceptional, (45)
"Wonderful, clean accommodations with everything you need. Amber and Jeremy were wonderful hosts—ready and willing to help if needed. Very close to the beach in a wonderful location. Couldn’t be happier. "
Spacious Maui Beach House, Private Pool, AC, Sleeps 6
PRIVATE HOME OASIS-3 BEDROOM-OCEAN VIEWS-POOL-HOT TUB-METICULOUS CLEANING

PRIVATE HOME OASIS-3 BEDROOM-OCEAN VIEWS-POOL-HOT TUB-METICULOUS CLEANING

9.8 out of 10, Exceptional, (70)
"Home exceeded our expectations. Private beautiful backyard and clean home. Quick access to everywhere we needed to go and had chairs and towels for the beach. Highly recommend this property! "
PRIVATE HOME OASIS-3 BEDROOM-OCEAN VIEWS-POOL-HOT TUB-METICULOUS CLEANING
PRIVATE HOME-NEWLY REMODELED-AC-HOT TUB-METICULOUS CLEANING

PRIVATE HOME-NEWLY REMODELED-AC-HOT TUB-METICULOUS CLEANING

9.8 out of 10, Exceptional, (58)
"The house was perfect, plenty of space, very nice amenities. Thank you very much!"
PRIVATE HOME-NEWLY REMODELED-AC-HOT TUB-METICULOUS CLEANING
Sugar Beach Resort condo with ocean view, AC - surf, bike & golf
Pool

Sugar Beach Resort condo with ocean view, AC - surf, bike & golf

8.8 out of 10, Excellent, (48)
"Beautiful sunsets, beach just off patio, and easy parking by door. Furniture needs updating and could be a little cleaner but rarely inside anyway. Small price to pay for view and price. Full kitchen and bath adequate. Towels, cooler, and beach chair available for use. Washer and dryer in room. Patio seats 4. Great place for breakfast. You can rent snorkel equip and life vests at shop on site. Gift bag upon arrival."
Sugar Beach Resort condo with ocean view, AC - surf, bike & golf
BEACHFRONT HOUSE KIHEI, MAUI..TRUE HAWAIIAN HOME 1960's
Property grounds

BEACHFRONT HOUSE KIHEI, MAUI..TRUE HAWAIIAN HOME 1960's

9.8 out of 10, Exceptional, (97)
"We truly enjoyed the beach house! The sunsets were amazing! "
BEACHFRONT HOUSE KIHEI, MAUI..TRUE HAWAIIAN HOME 1960's
Stunning Beach Front Townhouse
Interior

Stunning Beach Front Townhouse

10.0 out of 10, Exceptional, (87)
"Stunning is the right word for the location and view. The evening sunsets were beautiful.The condo has everything you need for a week of staying in or going out. Kitchen is well equipped, plenty of towels, and lots of beach gear.Couldn't ask for a better spot. We would definitley stay again!"
Stunning Beach Front Townhouse
BEACHFRONT MAUI KIHEI HOUSE
Fridge, microwave, oven, stovetop

BEACHFRONT MAUI KIHEI HOUSE

9.8 out of 10, Exceptional, (156)
"We were a multigenerational family with ages from 5 to 76 spending quality time together from 2 different parts of Canada. The house more than adequately suited our needs..the lanai was great for dinners, the yard was great for games, the beach was great for watching beautiful sunsets. Our host, Brian, was most accommodating and responded to our needs quickly. I would not hesitate to recommend this house for your family gathering…you will not regret it. Thank you, Brian, for sharing your...
BEACHFRONT MAUI KIHEI HOUSE
Spacious Hawaiian home 50 steps from Sugar Beach!
Sun-loungers, beach towels

Spacious Hawaiian home 50 steps from Sugar Beach!

8.8 out of 10, Excellent, (66)
"It was a great location and convenient to lots of things. More neighborhood and not resorty."
Spacious Hawaiian home 50 steps from Sugar Beach!
Amazing House with Pool, Spa, Cabana & More Kihei Wailea Area
Outdoor pool, a heated pool

Amazing House with Pool, Spa, Cabana & More Kihei Wailea Area

10.0 out of 10, Exceptional, (80)
"Great location, clean, comfortable and well maintained. The owner was easy to work with and truly provided everything that you need for a great vacation."
Amazing House with Pool, Spa, Cabana & More Kihei Wailea Area
Maui 🌺 Private Home in Wailea Kihei with 3 bed 2 bath Best Beaches on Maui
Beach nearby, beach towels

Maui 🌺 Private Home in Wailea Kihei with 3 bed 2 bath Best Beaches on Maui

10.0 out of 10, Exceptional, (82)
"Kelly and Dan are great hosts, super nice and very attentive. Their home is very clean and well stocked, conveniently located in a quiet neighborhood. I highly recommend booking with them!"
Maui 🌺 Private Home in Wailea Kihei with 3 bed 2 bath Best Beaches on Maui
Wailea Townhome, Perfect for Families! Wailea Ekahi 25B
A heated pool

Wailea Townhome, Perfect for Families! Wailea Ekahi 25B

6.6 out of 10, (47)
"Great spot!"
Wailea Townhome, Perfect for Families! Wailea Ekahi 25B
Gorgeous 2 Story Townhouse on The Blue Golf Course in Wailea with Ocean View
Beach nearby, sun-loungers, beach towels

Gorgeous 2 Story Townhouse on The Blue Golf Course in Wailea with Ocean View

10.0 out of 10, Exceptional, (66)
"stayed for one week with family and enjoyed the place very much. The host is very attentive and quick to respond to all questions/requests. We will come back."
Gorgeous 2 Story Townhouse on The Blue Golf Course in Wailea with Ocean View
Kihei Ocean Front Hale - Private Home w/ Dramatic Ocean Views on famed Halama St
Aerial view

Kihei Ocean Front Hale - Private Home w/ Dramatic Ocean Views on famed Halama St

2.0 star property
9.6 out of 10, Exceptional, (69)
"We enjoyed the ocean view and having a small beach a minute away. The house is beautiful. It lacked a few things and needed some minor repairs. We told the management company and they said they'll address them."
Kihei Ocean Front Hale - Private Home w/ Dramatic Ocean Views on famed Halama St
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.
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Other property types in South Maui

Snorkeling, Swimming and Sunsets! Steps from the beach!
On the beach, sun-loungers, beach towels

Snorkeling, Swimming and Sunsets! Steps from the beach!

10.0 out of 10, Exceptional, (131)
"Great place and stay!"
Snorkeling, Swimming and Sunsets! Steps from the beach!
Beachfront Condo B303 April 14-22 still available
TV, DVD player

Beachfront Condo B303 April 14-22 still available

10.0 out of 10, Exceptional, (86)
"Makena is a world class destination and the Makena Surf is a first class location. Located directly on one of the most beautiful beaches, this unit is in the best building and is impeccably maintained. This is not a rental unit but like the home of a close friend. Everything you would expect at home is there. We highly recommend it!"
Beachfront Condo B303 April 14-22 still available
Makena Surf C-107: Premier Luxury Condo • Local Art • 2 New Pools • Pickleball
On the beach, sun-loungers, beach towels

Makena Surf C-107: Premier Luxury Condo • Local Art • 2 New Pools • Pickleball

10.0 out of 10, Exceptional, (83)
"We enjoyed a week at this unit. Its a very nice condo that was clean and well stocked. The unit has a great view of the ocean and a peak view of the sunset. Its close walk to the beach or two pools. The pools were a little.cold while we were there. The one downside is the road noise in the morning. The unit is very close to the road"
Makena Surf C-107: Premier Luxury Condo • Local Art • 2 New Pools • Pickleball
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.