Lanikai Ola Nani: Majestic Retreat, Close to Beach, Designer Details, Views!From $699/night · Sleeps 8
Windward Beach Town
Kailua Vacation Rentals
Island Living on Oahu's Windward Side
Kailua offers one of Oahu's most peaceful and picturesque vacation settings. Located just 30 minutes from Honolulu, this seaside town is known for its soft white sands, turquoise waters, and small-town charm. With no high-rises in sight, Kailua maintains a residential, beach-friendly vibe ideal for extended stays, family retreats, and romantic escapes.
Popular Activities in Kailua
From your vacation rental, enjoy quick access to outdoor adventures like:
- Kayaking to the Mokulua Islands
- Hiking the scenic Lanikai Pillbox Trail
- Swimming and sunbathing at Kailua Beach Park
- Shopping local boutiques and farmers markets
Key Features of Kailua Vacation Rentals
- Steps from Kailua or Lanikai Beach
- Private lanais, gardens, and outdoor showers
- Beach gear often included (chairs, boogie boards, bikes)
- Quiet neighborhoods right for remote work or extended stays
- Local eateries, cafés, and groceries within walking distance
Right For:
- Families needing space and beach access
- Couples seeking a romantic, secluded getaway
- Remote workers looking for inspiration and tranquility
- Visitors planning longer-term stays in a residential setting
Kailua is more than a beach destination-it's a lifestyle. Book a stay in one of our handpicked Kailua vacation homes and find why travelers return to this corner of Oahu year after year.
Rental Listings
Kailua Vacation Rentals Listings
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Kailua Vacation Rentals Map
Lanikai Ola Nani: Majestic Retreat, Close to Beach, Designer Details, Views!From $699/night · Sleeps 8
Lanikai Monthly Home, Private Guest Suite, 2 Parking, and Walk to BeachFrom $724/night · Sleeps 8
Waterfront Lanikai Beach CompoundFrom $724/night · Sleeps 20
Bright Kai Nalu w/ Ocean Views, Lanai + Open LivingFrom $798/night · Sleeps 6
Private Luxury Home, Steps from the Beach w/ AC: Ranch Beach House EstateFrom $863/night · Sleeps 8
Beachside Kailua Beach House by Gather w/ Pool & Gourmet KitchenFrom $901/night · Sleeps 8
Kailua Hale Kahakai by Gather: Lux Oceanview Villa w/ Beach, Walk to AttractionsFrom $937/night · Sleeps 12
4BR Mokulua Seaside w/ Private Studio, Steps to the BeachFrom $989/night · Sleeps 10
Private, Chic, Beach Retreat, 4BR in Kailua, poolFrom $1,012/night · Sleeps 10
Leaf House: Lux Retreat w/ Pool, Ocean Views & Outdoor Living Near LanikaiFrom $1,650/night · Sleeps 10
Luxury Lanikai Oceanfront Home – Secluded Beachside EleganceFrom $2,022/night · Sleeps 6
Kailua Beachside: Lux Beachfront Villa w/ Heated Pool, Ocean Views & Modern AmenFrom $2,243/night · Sleeps 10
Kailua Luxury Beachfront HouseFrom $2,402/night · Sleeps 11
Kailua Beach Escape by Gather: Luxury Beachfront Estate w/ Pool, Hot Tub & ViewsFrom $3,617/night · Sleeps 12
Kailua Beachfront Estate by Gather: Beachfront Luxury w/ Pool, Spa & Guest HouseFrom $3,692/night · Sleeps 14
Lanikai Hillside Estate – Panoramic Luxury Above the SeaFrom $4,149/night · Sleeps 10
Hale Lanikai | Ko Olina |Penthouse Ko Olina VillaFrom $1,124/night · Sleeps 4
1000 steps from famous Lanikai beachFrom $199/night · Sleeps 7
Barefoot-Beach-Retreat, 2BR, Newly Furn. WALK-2-BEACH/BUZZ'S=2 MIN, Kaʻohao SCH.From $345/night · Sleeps 4
@ Marbella Lane - Sunshine Seascape | Ocean ViewFrom $480/night · Sleeps 8
From $699/night
Lanikai Ola Nani: Majestic Retreat, Close to Beach, Designer Details, Views!
Kailua, Hawaii
Lanikai Ola Nani is a luxury 4-bedroom island retreat just steps from the powdery sands of beautiful Lanikai Beach. Ideal for monthly stays, this...
From $724/night
Lanikai Monthly Home, Private Guest Suite, 2 Parking, and Walk to Beach
Kailua, Hawaii
Steps away from the shoreline, this Lanikai home invites you to settle into island living with the space, privacy, and flexibility to truly feel at...
From $724/night
Waterfront Lanikai Beach Compound
Kailua, Hawaii
This Lanikai oceanfront compound is a sprawling 5-bedroom, 5-bath retreat just steps from Lanikai Beach and a short walk to Kailua Beach Park....
From $798/night
Bright Kai Nalu w/ Ocean Views, Lanai + Open Living
Kailua, Hawaii
Wake up at Kai Nalu to wide ocean views, soft morning light, and the quiet rhythm of Kailua living. This thoughtfully designed 3-bedroom holiday home...
From $863/night
Private Luxury Home, Steps from the Beach w/ AC: Ranch Beach House Estate
Kailua, Hawaii
Ranch Beach Estate is a hidden gem just steps from Kailua's world-famous white sand beach, offering a private gated retreat with ocean views and two...
From $901/night
Beachside Kailua Beach House by Gather w/ Pool & Gourmet Kitchen
Kailua, Hawaii
Just a short stroll from the turquoise waters and powder-soft sands of Kailua Beach, Kailua Beach House is a light-filled 4-bedroom, 2.5-bath island...
From $937/night
Kailua Hale Kahakai by Gather: Lux Oceanview Villa w/ Beach, Walk to Attractions
Kailua, Hawaii
Welcome to Kailua Hale Kahakai, a serene beachfront estate set along one of the most breathtaking stretches of Kailua Beach. With six bedrooms, five...
From $989/night
4BR Mokulua Seaside w/ Private Studio, Steps to the Beach
Kailua, Hawaii
Mokulua Seaside is a luxurious oceanside retreat in Lanikai featuring a 3-bedroom main home plus a separate studio suite above the garage. Just steps...
From $1,012/night
Private, Chic, Beach Retreat, 4BR in Kailua, pool
Kailua, Hawaii
Welcome to your Kailua beach retreat! Just steps from the sand, our bright and private 4-bedroom house offers a gated beach house with private beach...
From $1,650/night
Leaf House: Lux Retreat w/ Pool, Ocean Views & Outdoor Living Near Lanikai
Kailua, Hawaii
Leaf House is a serene Lanikai vacation rental designed for ultimate relaxation and connection with nature. Perched on a peaceful hillside with...
From $2,022/night
Luxury Lanikai Oceanfront Home – Secluded Beachside Elegance
Kailua, Hawaii
This Lanikai Oceanfront Home is a luxurious retreat blending old Hawaii charm with modern comfort, featuring spacious concrete-floored interiors,...
From $2,243/night
Kailua Beachside: Lux Beachfront Villa w/ Heated Pool, Ocean Views & Modern Amen
Kailua, Hawaii
Welcome to Kailua Beachside, a five-bedroom, five-bath beachfront villa where modern design meets the relaxed rhythm of island life. Located on the...
From $2,402/night
Kailua Luxury Beachfront House
Kailua, Hawaii
Kailua Beach Villa is a luxurious 5-bedroom oceanfront retreat set on the world-famous sands of Kailua Beach on Oahu's windward coast. With over...
From $3,617/night
Kailua Beach Escape by Gather: Luxury Beachfront Estate w/ Pool, Hot Tub & Views
Kailua, Hawaii
Kailua Beach Escape is a newly renovated oceanfront estate set directly on the white sands of Kailua Beach. Following an extensive property-wide...
From $3,692/night
Kailua Beachfront Estate by Gather: Beachfront Luxury w/ Pool, Spa & Guest House
Kailua, Hawaii
Welcome to Kailua Beachfront Estate, an exceptional 7-bedroom, 6.5-bath sanctuary that sleeps up to 14 guests on O'ahu’s most exclusive stretch of...
From $4,149/night
Lanikai Hillside Estate – Panoramic Luxury Above the Sea
Kailua, Hawaii
Lanikai Hillside Estate is a stunning 7-bedroom luxury vacation home perched above the turquoise shores of Lanikai, offering over 8,400 sq. ft. of...
From $1,124/night
Hale Lanikai | Ko Olina |Penthouse Ko Olina Villa
Kapolei, Hawaii
★★★★★ 9.0/10 · 31 reviews
Summary:Welcome to Hale Lanikai in Ko Olina! With a private balcony, this space offers an unrivaled view of the lush gardens, serene lap pool, and...
From $199/night
1000 steps from famous Lanikai beach
lanikai, Hawaii
Welcome to your island sanctuary in one of Oahu’s most coveted gated communities—where privacy, luxury, and lifestyle come together in perfect...
From $345/night
Barefoot-Beach-Retreat, 2BR, Newly Furn. WALK-2-BEACH/BUZZ'S=2 MIN, Kaʻohao SCH.
Honolulu, Hawaii
★★★★★ 1 reviews
PEACEFUL BAREFOOT BEACH RETREAT in Kailua-Lanikai – Level easy walking path to walk to Kailua Beach, Buzz's Steak House and Kalapawai MarketWelcome...
From $480/night
@ Marbella Lane - Sunshine Seascape | Ocean View
Kaneohe, Hawaii
★★★★★ 8.0/10 · 5 reviews
Summary:Embark on a retreat to our contemporary haven boasting tranquil ocean views. This getaway offers all the essentials for a perfect stay....