1 Bdrm w/ocean view in Kona.Walk to Turtle Beach,Ali'i Gardens Mkt&Kona TrolleyFrom $155/night · Sleeps 2
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
1 Bdrm w/ocean view in Kona.Walk to Turtle Beach,Ali'i Gardens Mkt&Kona TrolleyFrom $155/night · Sleeps 2
Short walk to Kailua Beach across the street-Quiet AC's-Lg. Kitchen-Patio-GrillFrom $294/night · Sleeps 4
Lanikai Loop 3-bedroom 2-bath house, with lovely yard, a quiet relaxing getaway.From $376/night · Sleeps 6
Stunning Lanikai Home just steps to the Ocean-Authentic Hawaiian Tropical CharmFrom $788/night · Sleeps 10
Kailua vacation rental wih stunning views - 5 min to beachFrom $136/night · Sleeps 2
Charming 1.5 bedroom cottage, fully furnished in a great location!From $164/night · Sleeps 2
Relaxing 5bd/3ba Kailua Home Just Steps from Kailua Beach with Wifi and A/CFrom $713/night · Sleeps 12
Lanikai Oceanfront Home with Pool and Japanese-Style Hot TubFrom $1,661/night · Sleeps 18
🚐 Skip the hotel — 🏕️ Camping Experience — 🤑 Budget Friendly Vacation! 🏝️From $92/night · Sleeps 2
Charming apartment with AC and WiFi in serene Kailua.From $142/night · Sleeps 4
LANIKAI SUITE - Spacious 1-BR 1-BA; located 3 houses from famous LANIKAI BeachFrom $155/night · Sleeps 2
The Cicak Shack - a perfect beach hideawayFrom $169/night · Sleeps 2
LANIKAI Plantation Cottage located only 3 houses from famous Lanikai BeachFrom $199/night · Sleeps 6
Lanikai Lux LivingFrom $199/night · Sleeps 6
Cozy Apartment In Sought After Neighborhood of Olomana!From $199/night · Sleeps 4
Family cottage available July 17-August 1.From $199/night · Sleeps 7
Casa Luna - Beautiful & Stylish Remodeled 4bd, 3bath, 2 kitchens Home in KailuaFrom $199/night · Sleeps 8
Tropical Haven: 3BR Sanctuary Between Two Famous BeachesFrom $199/night · Sleeps 6
New Listing Keauhou Punahele C202, Ocean Views, PoolFrom $224/night · Sleeps 7
Sunlit Island Escape in KailuaFrom $253/night · Sleeps 6
Wonderful 3-bedroom house with AC in charming KailuaFrom $269/night · Sleeps 6
Cozy 2-bedroom apartment in charming Kailua with AC steps from the beach.From $282/night · Sleeps 3
Luxury Beach Cottage in charming KailuaFrom $285/night · Sleeps 6
Wake to the waves at “The Eddie” - 3 bed/2 bathFrom $291/night · Sleeps 8
Tropical Awakea CottageFrom $291/night · Sleeps 3
Keolu Hills Haven: Renovated 2/2 & Easy ParkingFrom $317/night · Sleeps 4
Steps to Kailua Beach • Relaxing 3BR Oasis • Fenced YardFrom $357/night · Sleeps 6
Spacious & Breezy 3 Bedroom Home with Ko'Olau Views and a PoolFrom $372/night · Sleeps 7
The Modern Kailua Beach HouseFrom $410/night · Sleeps 6
Hoʻonānea I Loko KailuaFrom $521/night · Sleeps 8
“The Reef” - Best beaches steps away- 3 bed/2 bathFrom $565/night · Sleeps 8
Seahorse Beach House: Calm Oasis w/ Private Yard Just Steps from Kailua BeachFrom $588/night · Sleeps 4
Hale Alapi'i Lanikai Getaway: Newly Renovated Near Beach & HikingFrom $615/night · Sleeps 6
From $155/night
1 Bdrm w/ocean view in Kona.Walk to Turtle Beach,Ali'i Gardens Mkt&Kona Trolley
Kailua, Hawaii
★★★★★ 10.0/10 · 2 reviews
Beautiful one bedroom beach side apartment in perfect location, on Ali'i Drive across the street from Turtle Beach. Water and beach access two blocks...
From $294/night
Short walk to Kailua Beach across the street-Quiet AC's-Lg. Kitchen-Patio-Grill
Kailua, Hawaii
★★★★★ 2 reviews
Live the beach life! An opportunity to live across the street from Kailua Beach Park, with the perfect combination of sandy beach, large grassy...
From $376/night
Lanikai Loop 3-bedroom 2-bath house, with lovely yard, a quiet relaxing getaway.
Kailua, Hawaii
★★★★★ 2 reviews
Free standing house with a big green yard. You can rest well to awaken and enjoy the soothing trade winds, in your home away from home in the Lanikai...
From $788/night
Stunning Lanikai Home just steps to the Ocean-Authentic Hawaiian Tropical Charm
Kailua, Hawaii
★★★★★ 2 reviews
Wake up to ocean breezes, tropical gardens, and the quiet magic of Lanikai. This authentic Hawaii home--rich with soul and character-- is located...
From $136/night
Kailua vacation rental wih stunning views - 5 min to beach
Kailua, Hawaii
★★★★★ 1 reviews
The studio is an overlooking Mid Pac country club, and has 180* views of the Ko'olau mountains and also the popular Pill Box hike peak which has...
From $164/night
Charming 1.5 bedroom cottage, fully furnished in a great location!
Kailua, Hawaii
★★★★★ 1 reviews
Welcome to this marvelous apartment in Kailua. This cozy space features 1 bedroom with a comfortable queen bed with mountain views, plus a separate...
From $713/night
Relaxing 5bd/3ba Kailua Home Just Steps from Kailua Beach with Wifi and A/C
Kailua, Hawaii
★★★★★ 1 reviews
Just four homes away from the Kailua Beach pristine white sands, this spacious retreat combines a stunning 4-bedroom home with a separate private...
From $1,661/night
Lanikai Oceanfront Home with Pool and Japanese-Style Hot Tub
Kailua, Hawaii
★★★★★ 1 reviews
This Lanikai vacation home is a spacious 6-bedroom oceanfront retreat featuring a private pool, Japanese-style onsen, and split A/C throughout -...
From $92/night
🚐 Skip the hotel — 🏕️ Camping Experience — 🤑 Budget Friendly Vacation! 🏝️
Kailua, Hawaii
Embark on a camping experience in Hawaii with our minivan camper perfect for individuals or couples.**Located in Kailua!! It's a 25 minute Uber/Lyft...
From $142/night
Charming apartment with AC and WiFi in serene Kailua.
Kailua, Hawaii
New charming studio rental located on the owner's property in beautiful Kailua, Hawaii. Perfectly situated just moments away from stunning beaches,...
From $155/night
LANIKAI SUITE - Spacious 1-BR 1-BA; located 3 houses from famous LANIKAI Beach
Kailua, Hawaii
This fully furnished, turn-key, spacious 1-bedroom, 1-bath, is part of a private, gated, rambling plantation-style property. The 2nd LEVEL apartment...
From $169/night
The Cicak Shack - a perfect beach hideaway
Kailua, Hawaii
Wake up to the sound of gentle waves and the scent of fresh ocean air in our Cicak Shack (pronounced ChEE-Chak, an Indonesian word for gecko). This...
From $199/night
LANIKAI Plantation Cottage located only 3 houses from famous Lanikai Beach
Kailua, Hawaii
This fully furnished 2-bedroom, 2-bath 2-story cottage is part of a private, gated, rambling plantation-style property. The 2nd level unit (not...
From $199/night
Lanikai Lux Living
Kailua, Hawaii
This 3 bedroom 2 1/2 bath townhouse is located in Lanikai. It is fully furnished and ready for move in. Gated Community with tennis courts , pool ,...
From $199/night
Cozy Apartment In Sought After Neighborhood of Olomana!
Kailua, Hawaii
NEW PHOTOS! One bedroom, one bath apartment in the quite neighborhood of Olomana. This cute apartment comes complete with a split system Split System...
From $199/night
Family cottage available July 17-August 1.
Kailua, Hawaii
Our spacious, clean 3 bedroom, 2 bath house has lots to offer for your stay. Just 7 mins walk to the beach, 30 mins drive to the airport, 20 mins...
From $199/night
Casa Luna - Beautiful & Stylish Remodeled 4bd, 3bath, 2 kitchens Home in Kailua
Kailua, Hawaii
This is a newly custom designed and remodeled 4 bdr - 3 bath - 2 kitchens home in one of the best neighborhoods of Oahu and Kailua. I designed this...
From $199/night
Tropical Haven: 3BR Sanctuary Between Two Famous Beaches
Kailua, Hawaii
-This Is A Fully Furnished Rental-Wifi Included-TV With Amazon Prime Video-Washer & Dryer -Free Parking On PremisesKeep it simple at this peaceful...
From $224/night
New Listing Keauhou Punahele C202, Ocean Views, Pool
Kailua, Hawaii
Welcome to Big Island Keauhou Punahele C202, your ideal Hawaiian escape nestled in the heart of Kailua-Kona on the stunning Big Island. This...
From $253/night
Sunlit Island Escape in Kailua
Kailua, Hawaii
Welcome to your island getaway! Nestled in the heart of Kailua, this bright and inviting home is perfectly located just minutes from Kailua Beach,...
From $269/night
Wonderful 3-bedroom house with AC in charming Kailua
Kailua, Hawaii
Located in Kailua, this lovely house offers a tranquil retreat for guests seeking comfort and space. With three queen bedrooms and two bathrooms...
From $282/night
Cozy 2-bedroom apartment in charming Kailua with AC steps from the beach.
Kailua, Hawaii
Kick back and relax in this calm, stylish beach getaway. This recently updated apartment features a living space with an ocean view from the balcony....
From $285/night
Luxury Beach Cottage in charming Kailua
Kailua, Hawaii
Experience Kailua like a local in this delightful 1-bedroom cottage. The bedroom features a comfy king bed, while the living room offers an...
From $291/night
Wake to the waves at “The Eddie” - 3 bed/2 bath
Kailua, Hawaii
“The Eddie” - 3 bed/2 bath This elevated family living space with local charm and large second-floor lanai is perfectly located just feet from the...
From $291/night
Tropical Awakea Cottage
Kailua, Hawaii
Experience comfort and tranquility in our newly built Hawaiian-style Cottage, perfect for temporary housing. This fully furnished retreat boasts its...
From $317/night
Keolu Hills Haven: Renovated 2/2 & Easy Parking
Kailua, Hawaii
This 2-bed/2-bath home with central air conditioning offers two queen beds (one ensuite), a work desk, and ample street parking next to the...
From $357/night
Steps to Kailua Beach • Relaxing 3BR Oasis • Fenced Yard
Kailua, Hawaii
TLA Approved! Walk to Kailua Beach • Fenced Yard • Updated 3BR/2BAEnjoy relaxed island living in this updated, fully furnished 3-bedroom, 2-bath home...
From $372/night
Spacious & Breezy 3 Bedroom Home with Ko'Olau Views and a Pool
Kailua, Hawaii
Nestled in a quiet neighborhood, this charming home is located just one mile from the heart of Kailua town's shopping and resturants. It is also just...
From $410/night
The Modern Kailua Beach House
Kailua, Hawaii
Relax in this Modern vacation retreat located right across the street from Kailua beach park. Just steps from the white sand beaches of...
From $521/night
Hoʻonānea I Loko Kailua
Kailua, Hawaii
If you're looking to work remotely, travel for work, remodel your home & have a place to live while it's worked on then this is the perfect home....
From $565/night
“The Reef” - Best beaches steps away- 3 bed/2 bath
Kailua, Hawaii
Wake up to the sound of waves and the scent of fresh ocean air in our ground floor 3 bed/2 bath beach unit. This family living space with local charm...
From $588/night
Seahorse Beach House: Calm Oasis w/ Private Yard Just Steps from Kailua Beach
Kailua, Hawaii
Experience relaxed coastal living at Seahorse Beach House by Gather, a serene monthly rental perched just steps from the soft white sands of Kailua...
From $615/night
Hale Alapi'i Lanikai Getaway: Newly Renovated Near Beach & Hiking
Kailua, Hawaii
Just a short stroll from turquoise water and powder-soft sand, Hale Alapi‘i Lanikai Getaway by Gather is a serene 4-bedroom, 3-bath retreat set in...