Place in Paradise - Kailua Beach Oceanfront Vacation HomeFrom $2,836/night · Sleeps 14
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
Place in Paradise - Kailua Beach Oceanfront Vacation HomeFrom $2,836/night · Sleeps 14
Stunning oceanfront cottageFrom $649/night · Sleeps 2
Walker's Lanikai Beach House – Historic Oceanfront RetreatFrom $2,893/night · Sleeps 14
Koi Palms 1 bedroom Cottage - Great location! 5 Minute Walk to Kailua Beach!From $317/night · Sleeps 2
'Kailua Lani Suite' short walk to Kailua Beach. Air conditioned and private.From $288/night · Sleeps 2
Available and legal for stays less than 30 days.From $269/night · Sleeps 2
From 185 nt Aloha Summer Sizzle 2025 incl AC, 5 Star Luxury on the Big IslandFrom $314/night · Sleeps 5
Tropical & inviting home w/spa, torches, waterfalls & ocean viewFrom $788/night · Sleeps 8
Perfect Kailua Vacation at Ka Hale Lai-House of Serenity-pool and spa.From $1,425/night · Sleeps 8
Beachside Kailua AC 3min walk to beach! Inquire for available dates!From $778/night · Sleeps 8
Oceanfront Luxury Condo Closest to BeachFrom $300/night · Sleeps 6
Kailua Beach "The Pink House" 100 Yards from OceanFrom $645/night · Sleeps 6
Kolea Landing Modern Beach House w/ Double Suite and Third Bedroom OptionFrom $644/night · Sleeps 6
3-Bedroom Available for MAY! 250 Steps to the Beach! MONTHLY DISCOUNT!From $449/night · Sleeps 6
Unique Oceanfront Home in Enclosed AreaFrom $630/night · Sleeps 6
Beach Villas at Kahalu‘u, Sunset/Ocean Views, Prime Snorkel/Surf Beach, Pool/SpaFrom $319/night · Sleeps 4
Hale Lanikai – Classic Hawaiian Style Beach House & Guest CottageFrom $2,250/night · Sleeps 8
Just 40 Feet to Kailua Beach from our Lush Green YardFrom $1,466/night · Sleeps 8
Happy House on Exquisite Kailua Beachside Property!From $467/night · Sleeps 6
Kailua Beachfront Vacation Home with PoolFrom $2,250/night · Sleeps 10
Lanikai Ocean Front Duplex Bungalow. AMAZING Location. Private ocean steps.From $782/night · Sleeps 4
Amazing 🌺 Kailua Beach House 🌺 Pool! Game Room! 1 House from BeachFrom $946/night · Sleeps 10
Gorgeous Lanikai Villa with Access to Secluded White Sand BeachFrom $4,392/night · Sleeps 15
Lovely Private Kailua CottageFrom $391/night · Sleeps 4
Hale Mokulua: Lanikai Multi-Home Estate - Sleeps 14From $993/night · Sleeps 14
Lanikai Cottage: Charming Tropical Oasis with Private PoolFrom $695/night · Sleeps 6
Ocean Front Private Residence at Keauhou BAY with Pool & Private DockFrom $2,940/night · Sleeps 10
La Bella’s Bed & Breakfast-Honu (Turtle) Suite-Walk to beach-In Kailua (O’ahu)From $440/night · Sleeps 4
Kailua Beach/Lanikai LUX apartment w/Ocean Views from Rooftop Sun DeckFrom $161/night · Sleeps 2
Hale Nani Lanikai: Beautiful Tropical Home Close to Beach w/Pool, Yard & ACFrom $654/night · Sleeps 8
Penthouse View in Lanikai LANIKAI NUC 90/BB -0108 Most comfortable for 2 or 3.From $340/night · Sleeps 4
Beach Studio with private yard in Lanikai - 30 day Minimum StayFrom $155/night · Sleeps 2
Beachside 🏖 Family, vacation home with pool 🌺 NO CLEANING FEE!From $1,176/night · Sleeps 10
From $2,836/night
Place in Paradise - Kailua Beach Oceanfront Vacation Home
Kailua, Hawaii
★★★★★ 10.0/10 · 236 reviews
Place in Paradise is a spacious 5-bedroom, 5.5-bath beachfront vacation rental located directly on world-famous Kailua Beach, offering stunning ocean...
From $649/night
Stunning oceanfront cottage
Kailua, Hawaii
★★★★★ 10.0/10 · 184 reviews
This beautifully restored one-of-a-kind oceanfront home has all the charm of yesteryear with the added conveniences and sustainability of today....
From $2,893/night
Walker's Lanikai Beach House – Historic Oceanfront Retreat
Kailua, Hawaii
★★★★★ 10.0/10 · 146 reviews
Walker's Lanikai Beach House is a historic oceanfront retreat on one of Oahu's most beautiful beaches. Originally built in 1934 by Queen...
From $317/night
Koi Palms 1 bedroom Cottage - Great location! 5 Minute Walk to Kailua Beach!
Kailua, Hawaii
★★★★★ 10.0/10 · 136 reviews
Come and enjoy our island home with us. Koi Palms Cottage is located within our gated property alongside our lovely Koi pond, in the quaint town of...
From $288/night
'Kailua Lani Suite' short walk to Kailua Beach. Air conditioned and private.
Kailua, Hawaii
★★★★★ 10.0/10 · 120 reviews
"In order to comply with Oahu's 90 day minimum short term rental laws, we may not advertise to rent for a period shorter than 90 days."Come enjoy...
From $269/night
Available and legal for stays less than 30 days.
Kailua, Hawaii
★★★★★ 10.0/10 · 118 reviews
Hawaii Sheffield House has been a legal bed and breakfast for over 35 years. We are available and legal for stays of less than 30 days. We provide a...
From $314/night
From 185 nt Aloha Summer Sizzle 2025 incl AC, 5 Star Luxury on the Big Island
Kailua, Hawaii
★★★★★ 10.0/10 · 113 reviews
Island breezes, fragrant blossoms, privacy - Na Hale O Keauhou, Hawaii's Best Kept Secret. This private 2 bedroom, 2-1/2 bath, 2 story town home is...
From $788/night
Tropical & inviting home w/spa, torches, waterfalls & ocean view
Kailua, Hawaii
★★★★★ 10.0/10 · 111 reviews
From the moment you arrive at Hale Wailele (Waterfall House), tropical scenes take your breath away. Perched above the Kona Coast, this spectacular...
From $1,425/night
Perfect Kailua Vacation at Ka Hale Lai-House of Serenity-pool and spa.
Kailua, Hawaii
★★★★★ 10.0/10 · 100 reviews
Perfect Kailua Home on 18,000 square feet of land all your own!! Lots of room to spread out!! We have a gorgeous newly tiled Swimming Pool and spa!...
From $778/night
Beachside Kailua AC 3min walk to beach! Inquire for available dates!
Kailua, Hawaii
★★★★★ 10.0/10 · 99 reviews
THIS PROPERTY IS A LEGAL SHORT TERM RENTALCONTACT HOST/RESERVATIONS & DETAILSThis airy, spacious four bedroom Kailua beachside vacation rental home...
From $300/night
Oceanfront Luxury Condo Closest to Beach
Kailua, Hawaii
★★★★★ 10.0/10 · 91 reviews
OCEANFRONT LUXURY CONDO CLOSEST TO BEACH 2br/2ba sleeps (4-6) White Sands Village, Kailua-Kona, Kona Coast, Big Island, Hawaii, USA (20 minutes south...
From $645/night
Kailua Beach "The Pink House" 100 Yards from Ocean
Kailua, Hawaii
★★★★★ 10.0/10 · 84 reviews
The Pink House is a charming Hawaiian-style beach retreat just 100 yards from beautiful Kailua Beach. This 3-bedroom, 2-bath home offers an open...
From $644/night
Kolea Landing Modern Beach House w/ Double Suite and Third Bedroom Option
Kailua, Hawaii
★★★★★ 10.0/10 · 76 reviews
Aloha and Welcome to Kolea LandingA short walk (less than 400 steps to be exact) and you will be relaxing at Lanikai Beach! Our 2,200 sf guest house...
From $449/night
3-Bedroom Available for MAY! 250 Steps to the Beach! MONTHLY DISCOUNT!
Kailua, Hawaii
★★★★★ 10.0/10 · 73 reviews
E komo mai to Hale Makai, our piece of island paradise in Kailua. Beachside and just three houses from Kailua Beach - you are going to love it...
From $630/night
Unique Oceanfront Home in Enclosed Area
Kailua, Hawaii
★★★★★ 10.0/10 · 61 reviews
Kona Onenalo is a ONE-OF-A-KIND property on the beautiful Kona Coast. There are 12 identical and individual homes in this quiet, gated community. The...
From $319/night
Beach Villas at Kahalu‘u, Sunset/Ocean Views, Prime Snorkel/Surf Beach, Pool/Spa
Kailua, Hawaii
★★★★★ 10.0/10 · 59 reviews
Welcome to Surfing Turtle Kona where there are ocean and sunset views from every room. Amazing access to the best snorkeling and surfing reef in...
From $2,250/night
Hale Lanikai – Classic Hawaiian Style Beach House & Guest Cottage
Kailua, Hawaii
★★★★★ 10.0/10 · 59 reviews
Hale Lanikai is a newly remodeled beachfront vacation rental offering classic Hawaiian charm with modern comforts, located on the soft sands of...
From $1,466/night
Just 40 Feet to Kailua Beach from our Lush Green Yard
Kailua, Hawaii
★★★★★ 10.0/10 · 47 reviews
Tropical Trade Winds and Unsurpassed Views are from our Beach Front Home. Opens up for full enjoyment of Hawaii's Climate. Our rap-around Lanai...
From $467/night
Happy House on Exquisite Kailua Beachside Property!
Kailua, Hawaii
★★★★★ 10.0/10 · 42 reviews
Kailua Beachside: Charming beach house steps from the white sands of beautiful Kailua Beach. Nestled in a large, private garden property, enclosed by...
From $2,250/night
Kailua Beachfront Vacation Home with Pool
Kailua, Hawaii
★★★★★ 10.0/10 · 41 reviews
Set on nearly an acre of prime Kailua Beach frontage, this newly refurbished 3-bedroom, 3-bath home features a large private swimming pool, flexible...
From $782/night
Lanikai Ocean Front Duplex Bungalow. AMAZING Location. Private ocean steps.
Kailua, Hawaii
★★★★★ 10.0/10 · 34 reviews
Location Location Location! Our Lanikai ocean front location exactly in front of the twin Mokulua Islands provides endless hours of outstanding views...
From $946/night
Amazing 🌺 Kailua Beach House 🌺 Pool! Game Room! 1 House from Beach
Kailua, Hawaii
★★★★★ 10.0/10 · 34 reviews
ALOHA! The Kailua Bliss Beach House is a casual and relaxed beach house in the quiet Beachside neighborhood in Kailua, located on a private street, 1...
From $4,392/night
Gorgeous Lanikai Villa with Access to Secluded White Sand Beach
Kailua, Hawaii
★★★★★ 10.0/10 · 28 reviews
This Lanikai oceanfront villa is a fully remodeled 5-bedroom, 4.5-bath gated estate blending 1918 architecture with a modern beach house design....
From $391/night
Lovely Private Kailua Cottage
Kailua, Hawaii
★★★★★ 10.0/10 · 23 reviews
Welcome to our newly renovated 1-bedroom spacious and private cottage that is super centrally located in the heart of Kailua. Our cottage is situated...
From $993/night
Hale Mokulua: Lanikai Multi-Home Estate - Sleeps 14
Kailua, Hawaii
★★★★★ 10.0/10 · 22 reviews
Hale Mokulua is a beautifully remodeled multi-home estate just steps from the white sands of Lanikai Beach. Perfect for multi-family or group...
From $695/night
Lanikai Cottage: Charming Tropical Oasis with Private Pool
Kailua, Hawaii
★★★★★ 10.0/10 · 17 reviews
Lanikai Cottage is a charming retreat just steps from Oahu's famous Lanikai Beach. Featuring two separate dwellings on one property, this cozy...
From $2,940/night
Ocean Front Private Residence at Keauhou BAY with Pool & Private Dock
Kailua, Hawaii
★★★★★ 10.0/10 · 17 reviews
Enjoy everything Hawaii has to offer in a very private three-acre estate on the shore of historic Keauhou Bay, six miles south of Kailua Kona on the...
From $440/night
La Bella’s Bed & Breakfast-Honu (Turtle) Suite-Walk to beach-In Kailua (O’ahu)
Kailua, Hawaii
★★★★★ 10.0/10 · 15 reviews
No detail is overlooked at this charming and luxurious home. La Bella’s Bed and Breakfast is the place to be if you are looking for a short walk to...
From $161/night
Kailua Beach/Lanikai LUX apartment w/Ocean Views from Rooftop Sun Deck
Kailua, Hawaii
★★★★★ 10.0/10 · 13 reviews
Tastefully remastered, 1937 cottage + rooftop lanai and BBQ area. The Kailua Beach Hideaway is tucked up on the hillside above the beach park, on a...
From $654/night
Hale Nani Lanikai: Beautiful Tropical Home Close to Beach w/Pool, Yard & AC
Kailua, Hawaii
★★★★★ 10.0/10 · 12 reviews
Nestled in the coveted Lanikai community of Kailua, Hale Nani Lanikai invites you to experience authentic island living in a refined, serene setting....
From $340/night
Penthouse View in Lanikai LANIKAI NUC 90/BB -0108 Most comfortable for 2 or 3.
Kailua, Hawaii
★★★★★ 10.0/10 · 11 reviews
THE PENTHOUSE IN LANIKAI – PRIVATE TOP-FLOOR RETREAT WITH SPECTACULAR OCEAN VIEWS30+ DAY RENTALWelcome to the Penthouse in Lanikai, our private...
From $155/night
Beach Studio with private yard in Lanikai - 30 day Minimum Stay
Kailua, Hawaii
★★★★★ 10.0/10 · 10 reviews
Escape to your beachside retreat with this beautifully renovated studio located just a block from the pristine sands of Lanikai Beach on the east...
From $1,176/night
Beachside 🏖 Family, vacation home with pool 🌺 NO CLEANING FEE!
Kailua, Hawaii
★★★★★ 10.0/10 · 9 reviews
This Kailua beachside haven is a newly remodeled luxury home just one block from beautiful Kailua Beach on Oahu's Windward Coast. Completely...