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

AirbnbBooking.comVrboExpediaKayakTripadvisorHotels.comAgoda.com
  1. VBOR
  2. Vacation Rentals with Pool
  3.  USA

  4.  Hawaii

  5.  Kapaa

  6.  Wailua Homesteads

Refine your search

Price per night

Amenity Filter

Rating

527 Best Vacation Rentals with Pool in Wailua Homesteads (Starting from $144)

Worldmark Kapaa Shore
Worldmark Kapaa Shore
Apartment
Kapaa, HI, USA
4.7k from Wailua Homesteads center

Apartments, Accommodations, Pools, Parking, Lodgings, Hot tubs, Places to stay, Self-catering

3 Bedrooms10 Guests
7.4

Good

33 reviews

$188
Average price / night
Check Availability
Sleeping Giant Cottage with Plunge Pool TNVC #1244
Sleeping Giant Cottage with Plunge Pool TNVC #1244
House
Kapaa, HI, 96746, United States
1.5k from Wailua Homesteads center

Barbecue, Dryer, Free Parking, Internet, Kitchen, Laundry, Living Area, Microwave, No Smoking

1 Bedroom4 Guests
9.8

Exceptional

78 reviews

$438
Average price / night
Check Availability
Wailua Bay View 115
Wailua Bay View 115
Apartment
Kapaa, HI, USA
4.7k from Wailua Homesteads center

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

2 Bedrooms4 Guests
8.8

Fabulous

4 reviews

$341
Average price / night
Check Availability
Wailua Bay View 105 Oceanfront Condo
Wailua Bay View 105 Oceanfront Condo
Condo
Kapaʻa, HI, 96746, United States
4.4k from Wailua Homesteads center

AC, Barbecue, Dryer, Free Parking, Internet, Laundry, Microwave, No Smoking, Pool

1 Bedroom2 Guests
10.0

Exceptional

1 reviews

$533
Average price / night
Check Availability
Luxury Oceanfront ground floor condo
Luxury Oceanfront ground floor condo
House
Kapaa, HI, USA
4.8k from Wailua Homesteads center

Luxury, Accommodations, Pools, Villas, Vacation homes, Cottages, Lodgings, Beach, Jacuzzis

2 Bedrooms6 Guests
New to Booking
$1339
Average price / night
Check Availability
Wailua Bay View 215 Oceanfront condo
Wailua Bay View 215 Oceanfront condo
Condo
Kapaʻa, HI, 96746, United States
4.4k from Wailua Homesteads center

AC, Barbecue, Dryer, Fitness Equipment, Free Parking, Internet, Kitchen, Laundry, Microwave

1 Bedroom2 Guests
9.2

Superb

5 reviews

$496
Average price / night
Check Availability
Gardenfront Escape with Ocean Views at Kapa’a Sands 24
Gardenfront Escape with Ocean Views at Kapa’a Sands 24
House
Kapaa, HI, USA
4.8k from Wailua Homesteads center

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

2 Bedrooms4 Guests
8.7

Fabulous

13 reviews

$258
Average price / night
Check Availability
Bamboo Suite - Beachfront Ground Floor Condo - Lae Nani 316
Bamboo Suite - Beachfront Ground Floor Condo - Lae Nani 316
Condo
Kapaʻa, HI, 96746, United States
4.7k from Wailua Homesteads center

Barbecue, Free Parking, Internet, Laundry, Microwave, No Smoking, Outdoor Space, Pool, TV

2 Bedrooms4 Guests
9.4

Superb

20 reviews

$523
Average price / night
Check Availability
"Sea Haven" at the Wailua Bay View 305
"Sea Haven" at the Wailua Bay View 305
Apartment
Kapaa, HI, USA
4.8k from Wailua Homesteads center

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

1 Bedroom2 Guests
8.0

Good

1 reviews

$304
Average price / night
Check Availability
Blue Hawaii - Top Floor Lae Nani 334 - Beachfront Condo with AC & WD
Blue Hawaii - Top Floor Lae Nani 334 - Beachfront Condo with AC & WD
Condo
Kapaʻa, HI, 96746, United States
4.7k from Wailua Homesteads center

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

1 Bedroom2 Guests
10.0

Exceptional

80 reviews

$478
Average price / night
Check Availability
Stunning Oceanfront Condo - The Seashore Hideaway, Wailua Bay View, Unit 208, Kapaa
Stunning Oceanfront Condo - The Seashore Hideaway, Wailua Bay View, Unit 208, Kapaa
Apartment
HI, USA
4.8k from Wailua Homesteads center

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

1 Bedroom2 Guests
New to Booking
$280
Average price / night
Check Availability
Luxury Gated Oceanfront Condo on Ground Floor
Luxury Gated Oceanfront Condo on Ground Floor
Condo
Kauai County, HI, 96746, United States
4.8k from Wailua Homesteads center

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

2 Bedrooms6 Guests
10.0

Exceptional

9 reviews

$1040
Average price / night
Check Availability
"Picture Perfect" Oceanfront Beauty Top Floor at Wailua Bay View!
"Picture Perfect" Oceanfront Beauty Top Floor at Wailua Bay View!
House
HI, USA
4.8k from Wailua Homesteads center

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

1 Bedroom4 Guests
8.0

Good

1 reviews

$326
Average price / night
Check Availability
Terrific 2-bedroom condo in Kapaʻa
Terrific 2-bedroom condo in Kapaʻa
Condo
Kapaʻa, HI, 96746, United States
4.8k from Wailua Homesteads center

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

2 Bedrooms6 Guests
New to Booking
$463
Average price / night
Check Availability
Stunning Oceanfront View Top Floor Condo at Wailua Bay View
Stunning Oceanfront View Top Floor Condo at Wailua Bay View
House
HI, USA
4.8k from Wailua Homesteads center

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

1 Bedroom2 Guests
9.7

Exceptional

3 reviews

$326
Average price / night
Check Availability
Spectacular Oceanfront Corner Condo with Expansive Top Floor Views at Wailua Bay View!
Spectacular Oceanfront Corner Condo with Expansive Top Floor Views at Wailua Bay View!
Condo
Kapaa, HI, 96746, United States
4.8k from Wailua Homesteads center

Dryer, Free Parking, Internet, Kitchen, Laundry, Living Area, Microwave, No Smoking, Outdoor Space

1 Bedroom2 Guests
9.6

Exceptional

127 reviews

$347
Average price / night
Check Availability
Wailua Bay View 103
Wailua Bay View 103
Apartment
Kapaa, HI, USA
4.8k from Wailua Homesteads center

Apartments, Cheap, Accommodations, Pools, Serviced apartments, 3-star, Lodgings, Vacation rentals, Beach

3 Bedrooms10 Guests
8.3

Very Good

16 reviews

$240
Average price / night
Check Availability
\"Picture Perfect\" Oceanfront on the Top Floor at Wailua Bay View!
\"Picture Perfect\" Oceanfront on the Top Floor at Wailua Bay View!
Condo
Kapaa, HI, 96746, United States
4.8k from Wailua Homesteads center

Dryer, Free Parking, Internet, Kitchen, Laundry, Living Area, Microwave, No Smoking, Outdoor Space

1 Bedroom2 Guests
9.2

Superb

135 reviews

$352
Average price / night
Check Availability
Wailua Bay View
Wailua Bay View
Apartment
Wailua Homesteads, Kapaa, Hawaii, USA
4.8k from Wailua Homesteads center

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

1 Bedroom4 Guests
9.0

Fabulous

2 reviews

$144
Average price / night
Check Availability
Breathtaking Oceanfront Views from Top Floor Condo at Wailua Bay View – A Coastal Paradise!
Breathtaking Oceanfront Views from Top Floor Condo at Wailua Bay View – A Coastal Paradise!
Condo
Kapaa, HI, 96746, United States
4.8k from Wailua Homesteads center

Dryer, Free Parking, Internet, Kitchen, Laundry, Living Area, Microwave, No Smoking, Outdoor Space

1 Bedroom2 Guests
9.2

Superb

55 reviews

$344
Average price / night
Check Availability
Luxury 2-Story Oceanfront Condo w/Views & Pool
Luxury 2-Story Oceanfront Condo w/Views & Pool
Apartment
Wailua, HI, USA
4.8k from Wailua Homesteads center

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

3 Bedrooms8 Guests
7.6

Good

9 reviews

$837
Average price / night
Check Availability
Charming Oceanfront Top Floor Condo at Wailua Bay with Stunning Views and Local Fisherman Sightings!
Charming Oceanfront Top Floor Condo at Wailua Bay with Stunning Views and Local Fisherman Sightings!
Condo
Kapaa, HI, 96746, United States
4.8k from Wailua Homesteads center

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

1 Bedroom2 Guests
9.0

Fabulous

88 reviews

$349
Average price / night
Check Availability
Breathtaking Sunrise View Oasis 3 Bedroom Sleeps 6, Oceanfront Luxury, Pool & AC
Breathtaking Sunrise View Oasis 3 Bedroom Sleeps 6, Oceanfront Luxury, Pool & AC
Condo
Kapaa, HI, 96746, United States
4.8k from Wailua Homesteads center

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

3 Bedrooms6 Guests
9.6

Exceptional

87 reviews

$1309
Average price / night
Check Availability
Wailua Bay View 108 Oceanfront, Ground floor condo centrally located
Wailua Bay View 108 Oceanfront, Ground floor condo centrally located
Condo
Wailua, HI, 96746, United States
4.8k from Wailua Homesteads center

Barbecue, Dryer, Free Parking, Internet, Kitchen, Laundry, Living Area, Microwave, No Smoking

1 Bedroom2 Guests
9.6

Exceptional

71 reviews

$306
Average price / night
Check Availability
Oceanfront!  Watch the surf from your private lanai! No hidden fees.  Book now!
Oceanfront! Watch the surf from your private lanai! No hidden fees. Book now!
Condo
Kapaa, HI, 96746, United States
4.8k from Wailua Homesteads center

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

1 Bedroom2 Guests
9.4

Superb

183 reviews

$286
Average price / night
Check Availability
Sunrise Oceanfront Luxury - 3BR Sleeps 6 - AC, 180° Ocean Views, Steps to Ocean!
Sunrise Oceanfront Luxury - 3BR Sleeps 6 - AC, 180° Ocean Views, Steps to Ocean!
Condo
Kapaa, HI, 96746, United States
4.8k from Wailua Homesteads center

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

3 Bedrooms6 Guests
9.0

Fabulous

57 reviews

$745
Average price / night
Check Availability
Just finished complete renovation in March, 2025
Just finished complete renovation in March, 2025
Condo
Kapaa, HI, 96746, United States
4.8k from Wailua Homesteads center

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

1 Bedroom4 Guests
9.4

Superb

120 reviews

$428
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 Wailua Homesteads.

Stay Near Wailua Homesteads's Top Attractions

VacationByOwnerRentals can help you find hotels, resorts, and rentals near many of 's top attractions, neighborhoods, and points of interest.

Wailua Homesteads Vacation Rentals with Pool on the Map

Frequently Asked Questions

You can explore 527 verified vacation rentals with a pool in Wailua Homesteads. 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 Wailua Homesteads vary depending on the season, property size, and whether the pool is private or shared. Rates typically start from around $144 per night, with private pool homes and peak travel periods often costing more.

Many rentals in Wailua Homesteads 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 Wailua Homesteads welcome pets. Currently, 1 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 Wailua Homesteads often include additional outdoor features such as Pool, View, and Ocean View. These amenities enhance comfort and make it easier to enjoy outdoor living during your stay.

Some vacation rentals in Wailua Homesteads 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.