Kailua Vacation Rentals

<p>Kailua is located on Oahu's east or "windward" shore and is home to two spectacular beaches as well as a lovely town with nice places to eat and shop. Kailua Beach and nearby Lanikai Beach are two of the finest beaches in Hawaii offering clear blue waters lined with white sand and typically enjoying calm conditions and pleasant onshore tropical trade winds.</p><p><b><br></b></p><p><b>Things To Do</b><br>Kailua Beach Park is an excellent place for ocean activities including swimming, bodyboarding, kayaking, surfing and more. Join a guided kayak tour to paddle out to one of the offshore islands, go snorkeling or take a surfing or stand up paddle boarding lesson from a local. Kailua is also quite bike friendly with miles of bike paths along the beach as well as in wetland areas where you can see native waterbirds. Mountain bikers will enjoy the Maunwaili bike trail at the base of the Koolau mountains which is popular for its stunning scenery and lush rainforest areas along a 20-mile route. A relatively easy yet rewarding hike in this area is the Kaiwa Ridge Trail leading up to the "pillboxes" which were shelter bunkers for soldiers guarding the area during World War II. This hike provides great views of Lanikai Beach, Kailua and the Mokulua Islands offshore. A more strenuous hike ascends Mount Olomana providing sweeping views of the windward coast. Another fun hike is the Maunawili Falls trail which leads to a nice waterfall and swimming hole. At Kawai Nui Marsh you can walk a path through wetlands to see native Hawaiian birds in their natural habitat. Golfers can choose from several exceptional courses on Oahu's windward side, all with impressive views of the Koolau mountain range. The scenic Koolau Golf Club is one of Hawaii's toughest courses, and the Olomana Golf Course is considered President Obama's favorite course with great views and memorable signature holes. The municipal Pali Golf Course extends along the foothills of the Koolau range with stunning mount…

39 vacation rentals found. Page 1 of 4 shows 10 properties (10 per page, same as the live site).

Kailua Vacation Rentals

Page 1 of 439 properties total — 10 per page (matches site listing view).

75-877 Lokahi Orchards

Holualoa, HI, US
  • 5 Bed
  • 6 Full Baths

From $4963.40 / night — Total price: $14890.20

Kona Mountain Retreat - Big Island of Hawaii

75-877 Lokahi Orchards

77-6386 Hale Alii Honu Kai

Kailua Kona, HI, US
  • 3 Bed
  • 3.5 Full Baths

From $4025.00 / night — Total price: $12075.00

Luxury Oceanfront Stay in Kona

77-6386 Hale Alii Honu Kai

BVH4 Leilani Kai

Waikoloa, HI, US
  • 3 Bed
  • 3 Full Baths

From $400.20 / night — Total price: $1200.60

Beach Villas in Waikoloa Beach Resort - Resort Townhome, Close to Shops, Restaurants & Beach

BVH4 Leilani Kai

CV402 Hale 'Olu'Olu

Waikoloa, HI, US
  • 3 Bed
  • 2.5 Full Baths

From $382.57 / night — Total price: $1147.71

Waikoloa Townhome, Close to Shopping & the Beach w/ AC

CV402 Hale 'Olu'Olu

FWN1 Hale 'O Ka La

Kamuela, HI, US
  • 5 Bed
  • 6.5 Full Baths

From $9282.80 / night — Total price: $27848.40

Hale ‘O Ka La, a Luxury Mauna Kea Home

FWN1 Hale 'O Ka La

FWV A22 Hale Okakopa

Waikoloa, HI, US
  • 2 Bed
  • 2 Full Baths

From $284.82 / night — Total price: $854.46

Fairway Villas Retreat – Waikoloa Beach Resort

FWV A22 Hale Okakopa

GVO3 Hale Maluhia

Kamuela, HI, US
  • 2 Bed
  • 2 Full Baths

From $414.00 / night — Total price: $1242.00

Hale Maluhia: Cozy 2BR condo in Mauna Lani, perfect for a serene getaway.

GVO3 Hale Maluhia

HK22E Hale Kailani

Waikoloa, HI, US
  • 3 Bed
  • 2 Full Baths

From $534.75 / night — Total price: $1604.25

Halii Kai 22E – Enjoy Luxury and Ocean Breezes in Waikoloa Beach Resort

HK22E Hale Kailani