Vacation Rentals with Pool in Wailea, HI: Compare 10+ Sites & Save

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  2. Vacation Rentals with Pool
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2364 Best Vacation Rentals with Pool in Wailea (Starting from $734)

MAKENA SURF #B304 condo
MAKENA SURF #B304 condo
Apartment
Wailea, HI, USA
1.3k from Wailea center

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

2 Bedrooms4 Guests
New to Booking
$1311
Average price / night
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Large 2BDR/2BA 3rd floor condo overlooking a private snorkel beach
Large 2BDR/2BA 3rd floor condo overlooking a private snorkel beach
Condo
Kihei, HI, 96753, United States
1.3k from Wailea center

AC, Balcony, Barbecue, Dryer, Elevator, Free Parking, Heater, Hot Tub, Internet

2 Bedrooms6 Guests
9.0

Fabulous

4 reviews

$966
Average price / night
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MAKENA SURF #F-102 condo
MAKENA SURF #F-102 condo
Apartment
Wailea, HI, USA
1.3k from Wailea center

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

2 Bedrooms6 Guests
New to Booking
$996
Average price / night
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Ultimate Beachfront Retreat: Makena Surf E204 - Prime Location & Amazing Views!
Ultimate Beachfront Retreat: Makena Surf E204 - Prime Location & Amazing Views!
Condo
Makena, Maui, HI, 96753, United States
1.3k from Wailea center

AC, Balcony, Dryer, Fitness Equipment, Free Parking, Hot Tub, Internet, Kitchen, Laundry

2 Bedrooms6 Guests
10.0

Exceptional

3 reviews

$1073
Average price / night
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MAKENA SURF, #C-205 condo
MAKENA SURF, #C-205 condo
Apartment
Wailea, HI, USA
1.3k from Wailea center

Apartments, Accommodations, Pools, Parking, Lodgings, Jacuzzis, Places to stay, Condos

2 Bedrooms4 Guests
New to Booking
$1258
Average price / night
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Luxurious Beachfront Condo with Modern Amenities - Makena Surf Resort #E-203
Luxurious Beachfront Condo with Modern Amenities - Makena Surf Resort #E-203
Condo
Makena, Maui, HI, 96753, United States
1.3k from Wailea center

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

2 Bedrooms6 Guests
10.0

Exceptional

3 reviews

$1124
Average price / night
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MAKENA SURF, #G-304 condo
MAKENA SURF, #G-304 condo
Apartment
Wailea, HI, USA
1.3k from Wailea center

Apartments, Accommodations, Pools, Parking, Lodgings, Jacuzzis, Places to stay, Condos

3 Bedrooms8 Guests
New to Booking
$1131
Average price / night
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Stunning Ground-Floor Retreat with Breathtaking Views! -Makena Surf #G-103:
Stunning Ground-Floor Retreat with Breathtaking Views! -Makena Surf #G-103:
Condo
Makena, Maui, HI, 96753, United States
1.3k from Wailea center

AC, Balcony, Barbecue, Dryer, Fitness Equipment, Free Parking, Hot Tub, Internet, Kitchen

2 Bedrooms6 Guests
New to Booking
$997
Average price / night
Check Availability
MAKENA SURF, #C-103 condo
MAKENA SURF, #C-103 condo
Apartment
Wailea, HI, USA
1.3k from Wailea center

Apartments, Accommodations, Pools, Parking, Lodgings, Jacuzzis, Places to stay, Condos

2 Bedrooms6 Guests
New to Booking
$959
Average price / night
Check Availability
Makena Surf F104 - Oceanfront 3BR w/ AC, Panoramic Views & Beach Access
Makena Surf F104 - Oceanfront 3BR w/ AC, Panoramic Views & Beach Access
Condo
Makena, Maui, HI, 96753, United States
1.3k from Wailea center

AC, Balcony, Barbecue, Dryer, Fitness Equipment, Free Parking, Hot Tub, Internet, Kitchen

3 Bedrooms6 Guests
New to Booking
$1372
Average price / night
Check Availability
MAKENA SURF #C102 condo
MAKENA SURF #C102 condo
Apartment
Wailea, HI, USA
1.3k from Wailea center

Apartments, Accommodations, Pools, Parking, Lodgings, Beach, Jacuzzis, Places to stay, Condos

2 Bedrooms6 Guests
New to Booking
$959
Average price / night
Check Availability
Fantastic Location - Beautiful Beach Front Condo -Makena Surf # B-208
Fantastic Location - Beautiful Beach Front Condo -Makena Surf # B-208
Condo
Makena, Maui, HI, 96753, United States
1.3k from Wailea center

AC, Balcony, Barbecue, Dryer, Fitness Equipment, Free Parking, Hot Tub, Internet, Kitchen

2 Bedrooms5 Guests
New to Booking
$1023
Average price / night
Check Availability
MAKENA SURF, #G-301-302 condo
MAKENA SURF, #G-301-302 condo
Apartment
Wailea, HI, USA
1.3k from Wailea center

Apartments, Accommodations, Pools, Parking, Lodgings, Beach, Jacuzzis, Places to stay, Condos

4 Bedrooms8 Guests
New to Booking
$2308
Average price / night
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Fully Remodeled Oceanfront Condo MAKENA SURF RESORT, #F-206
Fully Remodeled Oceanfront Condo MAKENA SURF RESORT, #F-206
Condo
Makena, Maui, HI, 96753, United States
1.3k from Wailea center

AC, Balcony, Barbecue, Dryer, Fitness Equipment, Free Parking, Hot Tub, Internet, Kitchen

2 Bedrooms4 Guests
New to Booking
$990
Average price / night
Check Availability
Makena Surf G303, Maui on the Beach
Makena Surf G303, Maui on the Beach
Apartment
Wailea, HI, USA
1.3k from Wailea center

Apartments, Cheap, Accommodations, Pools, Parking, Lodgings, Beach, Hot tubs, Places to stay

2 Bedrooms6 Guests
9.8

Exceptional

6 reviews

$1035
Average price / night
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Upgraded Unit w/ Beautiful Ocean Views -MAKENA SURF RESORT, #F-109
Upgraded Unit w/ Beautiful Ocean Views -MAKENA SURF RESORT, #F-109
Condo
Makena, Maui, HI, 96753, United States
1.3k from Wailea center

AC, Balcony, Barbecue, Dryer, Fitness Equipment, Free Parking, Hot Tub, Internet, Kitchen

2 Bedrooms6 Guests
New to Booking
$1069
Average price / night
Check Availability
MAKENA SURF, #E-303 condo
MAKENA SURF, #E-303 condo
Apartment
Wailea, HI, USA
1.3k from Wailea center

Apartments, Accommodations, Pools, Parking, Lodgings, Beach, Places to stay, Condos

2 Bedrooms6 Guests
New to Booking
$734
Average price / night
Check Availability
Breathtaking Views -Remodeled Ocean Front Condo - Makena Surf Resort F-111
Breathtaking Views -Remodeled Ocean Front Condo - Makena Surf Resort F-111
Condo
Makena, Maui, HI, 96753, United States
1.3k from Wailea center

AC, Balcony, Barbecue, Dryer, Fitness Equipment, Free Parking, Hot Tub, Internet, Kitchen

2 Bedrooms6 Guests
New to Booking
$1065
Average price / night
Check Availability
MAKENA SURF, #G-103 condo
MAKENA SURF, #G-103 condo
Apartment
HI, USA
1.3k from Wailea center

Apartments, Accommodations, Pools, Parking, Lodgings, Beach, Places to stay, Condos

2 Bedrooms6 Guests
New to Booking
$849
Average price / night
Check Availability
Stunning Beachfront Condo at Makena Surf Resort #E104 with Panoramic Ocean Views
Stunning Beachfront Condo at Makena Surf Resort #E104 with Panoramic Ocean Views
Condo
Makena, Maui, HI, 96753, United States
1.3k from Wailea center

AC, Balcony, Dryer, Fitness Equipment, Free Parking, Hot Tub, Internet, Kitchen, Laundry

2 Bedrooms4 Guests
New to Booking
$1259
Average price / night
Check Availability
MAKENA SURF, #E-203 condo
MAKENA SURF, #E-203 condo
Apartment
HI, USA
1.3k from Wailea center

Apartments, Accommodations, Pools, Lodgings, Beach, Places to stay, Condos

2 Bedrooms6 Guests
New to Booking
$1452
Average price / night
Check Availability
Gorgeous Oceanfront Sanctuary – Makena Surf #G-204 - Breathtaking Views!
Gorgeous Oceanfront Sanctuary – Makena Surf #G-204 - Breathtaking Views!
Condo
Makena, Maui, HI, 96753, United States
1.3k from Wailea center

AC, Balcony, Barbecue, Dryer, Fitness Equipment, Free Parking, Hot Tub, Internet, Kitchen

2 Bedrooms5 Guests
9.4

Superb

10 reviews

$956
Average price / night
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Beachfront Bliss: Makena Surf Resort B304 - Lovely Ocean Views & Lush Landscapes
Beachfront Bliss: Makena Surf Resort B304 - Lovely Ocean Views & Lush Landscapes
Condo
Makena, Maui, HI, 96753, United States
1.3k from Wailea center

AC, Balcony, Barbecue, Dryer, Fitness Equipment, Free Parking, Hot Tub, Internet, Kitchen

2 Bedrooms4 Guests
9.0

Fabulous

15 reviews

$1023
Average price / night
Check Availability
Luxurious Ground Level Haven - Stunning Inside & Out - Makena Surf Resort C102
Luxurious Ground Level Haven - Stunning Inside & Out - Makena Surf Resort C102
Condo
Makena, Maui, HI, 96753, United States
1.3k from Wailea center

AC, Balcony, Barbecue, Dryer, Fitness Equipment, Free Parking, Hot Tub, Internet, Kitchen

2 Bedrooms6 Guests
9.8

Exceptional

12 reviews

$870
Average price / night
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Stunning Beachfront Luxurious Corner Condo - Makena Surf E206 Enchanting Grounds
Stunning Beachfront Luxurious Corner Condo - Makena Surf E206 Enchanting Grounds
Condo
Kihei, HI, 96753, United States
1.3k from Wailea center

AC, Balcony, Barbecue, Dryer, Fitness Equipment, Free Parking, Hot Tub, Internet, Kitchen

2 Bedrooms6 Guests
10.0

Exceptional

13 reviews

$1207
Average price / night
Check Availability
Amazing Remodeled Oceanfront Escape – Makena Surf F-202 with Spectacular Views!
Amazing Remodeled Oceanfront Escape – Makena Surf F-202 with Spectacular Views!
Condo
Makena, Maui, HI, 96753, United States
1.3k from Wailea center

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

2 Bedrooms6 Guests
9.8

Exceptional

25 reviews

$882
Average price / night
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Gorgeous Ground-Floor Oasis – Makena Surf G-104 W/ Stunning Oceanfront Views!
Gorgeous Ground-Floor Oasis – Makena Surf G-104 W/ Stunning Oceanfront Views!
Condo
Wailea-Makena, HI, 96753, United States
1.3k from Wailea center

AC, Balcony, Barbecue, Dryer, Fitness Equipment, Free Parking, Hot Tub, Internet, Kitchen

2 Bedrooms6 Guests
10.0

Exceptional

13 reviews

$935
Average price / night
Check Availability

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 Vacation Rentals with Pool in Wailea.

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Wailea Vacation Rentals with Pool on the Map

Frequently Asked Questions

You can explore 2364 verified vacation rentals with a pool in Wailea. These include a wide range of private homes, villas, and condos that offer on-site swimming facilities for a more relaxing stay.

Prices for vacation rentals with a pool in Wailea vary depending on the season, property size, and whether the pool is private or shared. Rates typically start from around $734 per night, with private pool homes and peak travel periods often costing more.

Many rentals in Wailea offer private pools for exclusive use, while others provide access to shared or community pools. You can use filters to specifically find properties with private pools if that is your preference.

Yes, some vacation rentals with pools in Wailea welcome pets. Currently, 4 listings allow pets, although policies may vary by property. It’s a good idea to review any rules related to pets around pool areas before booking.

Properties with pools are often in high demand, especially during warmer months and holidays, so booking 90 to 120 days in advance is recommended for the best selection. During off-peak seasons, you may still find availability closer to your travel dates.

Vacation rentals with pools in Wailea often include additional outdoor features such as Pool, Guest Services, and Sports/Activities. These amenities enhance comfort and make it easier to enjoy outdoor living during your stay.

Some vacation rentals in Wailea offer heated pools, which can be especially useful during cooler months. In certain cases, pool heating may be available for an additional fee, so it’s best to check the property details before booking.