Family-Friendly Vacation Rentals in Makamakaole Trail, HI: Compare 10+ Sites & Save

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  5.  Kihei
  6.  Makamakaole Trail

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2385 Best Family Vacation Rentals in Makamakaole Trail (Starting from $221)

WBH D225 Aloha Ola - Ocean and Pool View
WBH D225 Aloha Ola - Ocean and Pool View
House
Kihei, HI, USA
0.3k from Makamakaole Trail center

Cheap, Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Beach

1 Bedroom4 Guests
10.0

Exceptional

2 reviews

$331
Average price / night
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 2BR/1BA BEACHFRONT - GREAT LOCATION- EXCEPTIONAL REVIEWS
2BR/1BA BEACHFRONT - GREAT LOCATION- EXCEPTIONAL REVIEWS
Apartment
Kihei, HI, 96753, United States
0.1k from Makamakaole Trail center

AC, Balcony, Barbecue, Crib, Dryer, Free Parking, Internet, Kitchen, Laundry

2 Bedrooms5 Guests
10.0

Exceptional

52 reviews

$504
Average price / night
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WBH D225 Aloha Ola2 - Relax in Oceanfront Paradise
WBH D225 Aloha Ola2 - Relax in Oceanfront Paradise
House
Kihei, HI, USA
0.3k from Makamakaole Trail center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Beach, Places to stay

1 Bedroom4 Guests
10.0

Exceptional

1 reviews

$331
Average price / night
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RARE, GATED, PRIVATE BEACHFRONT HOME! PRIVATE POOL, 6 BEDS  6 BATHS
RARE, GATED, PRIVATE BEACHFRONT HOME! PRIVATE POOL, 6 BEDS 6 BATHS
Villa
Kihei, HI, 96753, United States
0.1k from Makamakaole Trail center

AC, Balcony, Barbecue, Crib, Dryer, Free Parking, Heater, Internet, Kitchen

6 Bedrooms12 Guests
10.0

Exceptional

204 reviews

$3625
Average price / night
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Maalaea Surf A6 · MAS A6 Remodeled Beachfront 2BD w Year Round B
Maalaea Surf A6 · MAS A6 Remodeled Beachfront 2BD w Year Round B
House
Kihei, HI, USA
0.3k from Makamakaole Trail center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay

1 Bedroom6 Guests
8.0

Good

1 reviews

$999
Average price / night
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Paradise Family Rental on Sunny South Shore! Beachfront Charm with Pool!
Paradise Family Rental on Sunny South Shore! Beachfront Charm with Pool!
House
Kihei, HI, 96753, United States
0.2k from Makamakaole Trail center

AC, Balcony, Barbecue, Dryer, Free Parking, Internet, Kitchen, Laundry, Living Area

4 Bedrooms14 Guests
9.8

Exceptional

104 reviews

$2541
Average price / night
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Beautiful 2BR 2BA with Panoramic Ocean Views, Wifi, Free Parking!
Beautiful 2BR 2BA with Panoramic Ocean Views, Wifi, Free Parking!
Apartment
Makamakaole Trail, Kihei, Hawaii, USA
0.3k from Makamakaole Trail center

Apartments, Accommodations, Pools, Parking, Lodgings, Vacation rentals, Beach, Places to stay, Self-catering

2 Bedrooms4 Guests
8.9

Fabulous

21 reviews

$604
Average price / night
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Paradise Found Poolside Bliss Great Rates
Paradise Found Poolside Bliss Great Rates
Condo
Kihei, HI, 96753, United States
0.3k from Makamakaole Trail center

AC, Balcony, Barbecue, Crib, Dryer, Extra Bed, Free Parking, Internet, Kitchen

1 Bedroom4 Guests
9.8

Exceptional

108 reviews

$316
Average price / night
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Beautiful 1 Bedroom Condo with Ocean Views | Oceanfront
Beautiful 1 Bedroom Condo with Ocean Views | Oceanfront
Apartment
Makamakaole Trail, Kihei, Hawaii, USA
0.3k from Makamakaole Trail center

Apartments, Cheap, Accommodations, Pools, Parking, Lodgings, Vacation rentals, Beach, Places to stay

1 Bedroom4 Guests
9.0

Fabulous

23 reviews

$479
Average price / night
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Beautiful Maui Beachfront Townhouse! Great Views! 200+ Five Star Reviews !!!
Beautiful Maui Beachfront Townhouse! Great Views! 200+ Five Star Reviews !!!
House
Kihei, HI, 96753, United States
0.3k from Makamakaole Trail center

AC, Balcony, Barbecue, Dryer, Free Parking, Internet, Kitchen, Laundry, Living Area

2 Bedrooms6 Guests
10.0

Exceptional

170 reviews

$966
Average price / night
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WBH D115 Aloha Kai - Garden View Suite near the Ocean
WBH D115 Aloha Kai - Garden View Suite near the Ocean
Apartment
Makamakaole Trail, Kihei, Hawaii, USA
0.3k from Makamakaole Trail center

Apartments, Accommodations, Pools, Parking, Lodgings, Vacation rentals, Beach, Places to stay, Self-catering

2 Bedrooms4 Guests
9.4

Superb

28 reviews

$253
Average price / night
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Oceanfront - Fantastic View - Affordable: 2 Br + 2 Ba Waiohuli Beach Hale A203
Oceanfront - Fantastic View - Affordable: 2 Br + 2 Ba Waiohuli Beach Hale A203
Condo
Kihei, HI, 96753, United States
0.3k from Makamakaole Trail center

AC, Balcony, Barbecue, Free Parking, Internet, Kitchen, Laundry, Living Area, Microwave

2 Bedrooms6 Guests
9.6

Exceptional

72 reviews

$389
Average price / night
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WBH D115 Aloha Kai2 - Garden View Suite by the Sea
WBH D115 Aloha Kai2 - Garden View Suite by the Sea
Apartment
Makamakaole Trail, Kihei, Hawaii, USA
0.3k from Makamakaole Trail center

Apartments, Accommodations, Pools, Parking, Lodgings, Vacation rentals, Beach, Places to stay, Self-catering

1 Bedroom4 Guests
8.0

Good

2 reviews

$253
Average price / night
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Beachfront 2 BR Ground Floor Condo
Beachfront 2 BR Ground Floor Condo
Condo
Kihei, HI, 96753, United States
0.3k from Makamakaole Trail center

AC, Barbecue, Crib, Dryer, Free Parking, Internet, Kitchen, Laundry, Living Area

2 Bedrooms6 Guests
9.8

Exceptional

115 reviews

$424
Average price / night
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WBH D116 Aloha Wai - Garden Suite Just Steps from the Sea
WBH D116 Aloha Wai - Garden Suite Just Steps from the Sea
Apartment
Kihei, HI, USA
0.3k from Makamakaole Trail center

Apartments, Cheap, Accommodations, Pools, Parking, Lodgings, Vacation rentals, Beach, Places to stay

1 Bedroom4 Guests
9.4

Superb

35 reviews

$301
Average price / night
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 Escape to our Cozy 2 BR/1BA COTTAGE in Kihei!
Escape to our Cozy 2 BR/1BA COTTAGE in Kihei!
Cottage
Kihei, HI, 96753, United States
0.3k from Makamakaole Trail center

AC, Barbecue, Crib, Free Parking, Internet, Kitchen, Laundry, Living Area, Microwave

2 Bedrooms4 Guests
10.0

Exceptional

29 reviews

$457
Average price / night
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WBH D116 Aloha Wai2 - Serene Garden view by the Sea
WBH D116 Aloha Wai2 - Serene Garden view by the Sea
Apartment
Kihei, HI, USA
0.3k from Makamakaole Trail center

Apartments, Accommodations, Pools, Parking, Lodgings, Vacation rentals, Beach, Places to stay, Beach rentals

1 Bedroom4 Guests
New to Booking
$301
Average price / night
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BEST LOCATION IN KIHEI!  Incredible Lani, Pool & beach!  2 bd, 2 bath, grd floor
BEST LOCATION IN KIHEI! Incredible Lani, Pool & beach! 2 bd, 2 bath, grd floor
Condo
Kihei, HI, 96753, United States
0.3k from Makamakaole Trail center

AC, Barbecue, Crib, Dryer, Free Parking, Internet, Kitchen, Laundry, Living Area

2 Bedrooms6 Guests
9.6

Exceptional

64 reviews

$399
Average price / night
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WBH D227 Aloha Lai - Breathtaking Ocean Views
WBH D227 Aloha Lai - Breathtaking Ocean Views
Apartment
Kihei, HI, USA
0.3k from Makamakaole Trail center

Apartments, Cheap, Accommodations, Pools, Parking, Serviced apartments, Lodgings, Vacation rentals, Beach

1 Bedroom4 Guests
9.8

Exceptional

13 reviews

$308
Average price / night
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Perch - Kihei Garden Estates
Perch - Kihei Garden Estates
Condo
Kihei, HI, 96753, United States
0.4k from Makamakaole Trail center

AC, Balcony, Barbecue, Dryer, Free Parking, Hot Tub, Internet, Kitchen, Laundry

2 Bedrooms6 Guests
10.0

Exceptional

2 reviews

$550
Average price / night
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WBH D227 Aloha Lai2 - Unwind in a Peaceful Oceanfront Suite
WBH D227 Aloha Lai2 - Unwind in a Peaceful Oceanfront Suite
Apartment
Kihei, HI, USA
0.3k from Makamakaole Trail center

Apartments, Cheap, Accommodations, Pools, Parking, Lodgings, Vacation rentals, Beach, Places to stay

1 Bedroom4 Guests
9.3

Superb

3 reviews

$271
Average price / night
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Charming Tropical Kihei Gardens 2-Bed Suite
Charming Tropical Kihei Gardens 2-Bed Suite
Condo
Kihei, HI, 96753, United States
0.4k from Makamakaole Trail center

AC, Balcony, Barbecue, Dryer, Free Parking, Hot Tub, Internet, Kitchen, Laundry

2 Bedrooms4 Guests
6.0

Review score

1 reviews

$286
Average price / night
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Lush Garden Charmer - Breathtaking Sunsets
Lush Garden Charmer - Breathtaking Sunsets
Condo
Kihei, HI, 96753, United States
0.4k from Makamakaole Trail center

AC, Barbecue, Crib, Dryer, Free Parking, Hot Tub, Internet, Kitchen, Laundry

1 Bedroom4 Guests
9.6

Exceptional

134 reviews

$221
Average price / night
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BEST LOCATION in Kihei! 1BD/1BA by the BEACH! A/C, Clean, Cozy, Wifi, Beach Gear
BEST LOCATION in Kihei! 1BD/1BA by the BEACH! A/C, Clean, Cozy, Wifi, Beach Gear
Condo
Kihei, HI, 96753, United States
0.4k from Makamakaole Trail center

AC, Barbecue, Dryer, Extra Bed, Free Parking, Hot Tub, Internet, Kitchen, Laundry

1 Bedroom5 Guests
9.2

Superb

113 reviews

$504
Average price / night
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Great Location- Quiet Beach, Small Complex, Walk to Bars & Restaurants
Great Location- Quiet Beach, Small Complex, Walk to Bars & Restaurants
Condo
Kihei, HI, 96753, United States
0.4k from Makamakaole Trail center

AC, Barbecue, Dryer, Free Parking, Hot Tub, Internet, Kitchen, Laundry, Living Area

2 Bedrooms4 Guests
9.8

Exceptional

196 reviews

$253
Average price / night
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Aloha Villas # 2, Steps to Beach, Close to Golf &
Aloha Villas # 2, Steps to Beach, Close to Golf &
Condo
Kihei, HI, 96753, United States
0.4k from Makamakaole Trail center

AC, Balcony, Barbecue, Dryer, Internet, Kitchen, Laundry, Living Area, Microwave

3 Bedrooms8 Guests
9.8

Exceptional

48 reviews

$1873
Average price / night
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200ft from the Beach & Restaurants - King & Twin Beds Pool WIFI
200ft from the Beach & Restaurants - King & Twin Beds Pool WIFI
Condo
Kihei, HI, 96753, United States
0.4k from Makamakaole Trail center

AC, Balcony, Barbecue, Breakfast Available, Crib, Dryer, Free Parking, Hot Tub, Internet

2 Bedrooms4 Guests
9.2

Superb

21 reviews

$660
Average price / night
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Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Family Vacation Rentals in Makamakaole Trail.

Where to stay in Makamakaole Trail? Best neighborhoods & areas

Makamakaole Trail Family Vacation Rentals on the Map

Frequently Asked Questions

You can explore 2385 verified family-friendly vacation rentals in Makamakaole Trail. These include spacious homes, villas, and condos designed to accommodate families of different sizes.

Prices for family-friendly rentals in Makamakaole Trail vary depending on the season, number of bedrooms, and included amenities. Rates typically start from around $221 per night, with larger homes and peak travel periods often costing more.

Many family-friendly rentals in Makamakaole Trail offer baby-friendly items such as high chairs, cribs, or pack-and-play options. Availability can vary, so it’s helpful to check the listing details before booking.

Yes, some rentals in Makamakaole Trail are well suited for multi-generational stays, offering multiple bedrooms, separate living areas, and enough space for larger groups to stay comfortably together.

For busy travel periods such as school holidays or summer breaks, booking 90 to 120 days in advance is recommended to secure the best options. Availability may be more flexible during quieter times of the year.

Family-friendly rentals in Makamakaole Trail often include amenities such as Child Friendly, View, and Ocean View. These features help make stays more convenient and enjoyable for both adults and children.

You can use search filters to find rentals that offer features like game rooms, playgrounds, or entertainment areas. Checking property descriptions can also help you identify homes that are well suited for families with children.