New 3 Bdrm, Large Lanai, Quiet area, Ocean Breezes, Short Walk to the BeachFrom $216/night · Sleeps 6
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
New 3 Bdrm, Large Lanai, Quiet area, Ocean Breezes, Short Walk to the BeachFrom $216/night · Sleeps 6
Kailua Home Pool & Spa with amazing viewsFrom $340/night · Sleeps 7
Sweet Vintage Hawaiian Cottage and Guest House! Great deal in beautiful Lanikai!From $282/night · Sleeps 6
Bright, breezy, upgraded house, near the ocean! Contact for rates/availability!From $409/night · Sleeps 6
Classic Kailua Beach House – Oceanfront Bliss in Windward OahuFrom $2,350/night · Sleeps 10
Viewhouse in Lanikai BEST LOCATION, LANIKAI NUC 90/BB -0108From $357/night · Sleeps 4
Palione Papalani - Tropical Estate with Lagoon Pool on Kailua BeachFrom $3,093/night · Sleeps 16
Huge House Near Kailua Beach, Short Stay AvailableFrom $1,463/night · Sleeps 20
Close to the Beautiful Kailua Beach-A/C's-Full Kitchen-Covered Patio-Pet okFrom $298/night · Sleeps 4
Quaint Tropical Cottage w/Pool, Lanai & AC, Walk to Beach: Lanikai Ohana HaleFrom $678/night · Sleeps 4
Kailuana Beachfront Estate: 5 BR Kailua Oceanfront HomeFrom $2,836/night · Sleeps 12
New Listing: Spacious Suite for 4x with panoramic ocean viewFrom $171/night · Sleeps 4
Kailua Palms Guest House with Pool and Views! Parking and wi-fi includedFrom $591/night · Sleeps 4
1 Bdrm Ocean View walk to Turtle Beach, close to Kona Village&Magic Sands BeachFrom $150/night · Sleeps 2
MINUTES TO KAILUA BEACH-FABULOUS POOL great indoor/ outdoor livingFrom $461/night · Sleeps 4
Absolutely Oceanfront - 60' Waterfall Lap PoolFrom $556/night · Sleeps 2
Ocean View Guest Cottage - 1990/NUC-1797From $499/night · Sleeps 4
'Star of Hawaii' Beachside, Pool, Steps to Beach - Great for FamiliesFrom $670/night · Sleeps 10
Luxury Beach Vacation House in Kailua BeachFrom $1,980/night · Sleeps 14
🏖️Excellent Ocean View | AC | Concierge Included | vrKCVFrom $157/night · Sleeps 4
1 bdrm peakaboo ocean view walk to Turtle Beach, Alii Garden Mkt,Kona Village-1DFrom $125/night · Sleeps 3
Kailua Beach Estate: Historic Property with Large Yard & Ocean ViewFrom $650/night · Sleeps 6
Award Winner - Hawaii's Hidden Hideaway - Bed and BreakfastFrom $295/night · Sleeps 3
RENOVATED Studio By The Ocean!!!From $115/night · Sleeps 2
Steps to beach, pool, garden. April/May Cancellation Special. CALL NOW!From $625/night · Sleeps 6
🏖️Ocean View | Close to Pool & BBQ Area | vrKCVFrom $131/night · Sleeps 4
Open-Plan Lush Garden Home Near Kailua & Lanikai BeachesFrom $372/night · Sleeps 8
Oceanfront Condo Total Remodel 2025 2 Pools Kona Sunsets Private Lanai A/CFrom $293/night · Sleeps 4
Maluhia: Luxurious Kailua Home w/Pool Oasis, A/C, Near Beaches and Shopping!From $1,180/night · Sleeps 9
Aloha Lil Hawaiiana 🌺From $145/night · Sleeps 2
Ohana Rental Cottage Close to BeachFrom $295/night · Sleeps 6
Private Luxury Home, Steps from the Beach w/ AC, Ranch Beach HouseFrom $447/night · Sleeps 4
Cozy Lanikai Cottage Walking Distance to the Beach-Near Shops & RestaurantsFrom $122/night · Sleeps 2
From $216/night
New 3 Bdrm, Large Lanai, Quiet area, Ocean Breezes, Short Walk to the Beach
Kailua, Hawaii
★★★★★ 9.8/10 · 32 reviews
One Rate for 7 up to 30 day stay - A 30 day minimum lease.Hawaii Tax ID # available upon requestMountain View's cooling breezes , easy 5 minute walk...
From $340/night
Kailua Home Pool & Spa with amazing views
Kailua, Hawaii
★★★★★ 9.8/10 · 29 reviews
Two story home in Quiet Kailua neighborhood. Master bedroom is overlooking a beautiful pool and spa with views over the town of Kailua and the ocean....
From $282/night
Sweet Vintage Hawaiian Cottage and Guest House! Great deal in beautiful Lanikai!
Kailua, Hawaii
★★★★★ 9.8/10 · 25 reviews
At Old Hawaii Beach House and Guest Cottage in Lanikai, we extend to all our guests the old-fashioned Hawaiian Hospitality, and the famous Spirit of...
From $409/night
Bright, breezy, upgraded house, near the ocean! Contact for rates/availability!
Kailua, Hawaii
★★★★★ 9.8/10 · 21 reviews
This is a short-term vacation rental. Welcome to Hale Alapi'i, our home in fabulous Lanikai!This is a 3b/2b ~1,400 sq. ft. main house that sleeps 4...
From $2,350/night
Classic Kailua Beach House – Oceanfront Bliss in Windward Oahu
Kailua, Hawaii
★★★★★ 9.6/10 · 144 reviews
This Kailua Beachfront Home is a relaxed oceanfront retreat offering panoramic views of Kailua Bay and the Ko'olau Mountains. Located just minutes...
From $357/night
Viewhouse in Lanikai BEST LOCATION, LANIKAI NUC 90/BB -0108
Kailua, Hawaii
★★★★★ 9.6/10 · 99 reviews
Only a 5-minute walk to world-famous Lanikai Beach! One of the few legal nightly rentalsWelcome to the Viewhouse in Lanikai. Our family has owned,...
From $3,093/night
Palione Papalani - Tropical Estate with Lagoon Pool on Kailua Beach
Kailua, Hawaii
★★★★★ 9.6/10 · 88 reviews
Palione Papalani - meaning "Heavenly Sands" - is a newly renovated 6-bedroom luxury vacation rental just steps from Kailua Beach, offering the...
From $1,463/night
Huge House Near Kailua Beach, Short Stay Available
Kailua, Hawaii
★★★★★ 9.6/10 · 84 reviews
Summary:Inquire about short stays – we accommodate them when possible. This spacious, resort-style residence is located just 100 yards from Kailua...
From $298/night
Close to the Beautiful Kailua Beach-A/C's-Full Kitchen-Covered Patio-Pet ok
Kailua, Hawaii
★★★★★ 9.6/10 · 76 reviews
For questions, to verify availability dates or to check the availability of other furnished rentals we manage, please contact the owner. This large...
From $678/night
Quaint Tropical Cottage w/Pool, Lanai & AC, Walk to Beach: Lanikai Ohana Hale
Kailua, Hawaii
★★★★★ 9.6/10 · 45 reviews
Discover your private island retreat at Charming Cottage in Lanikai by Gather, a beautifully renovated 1-bedroom, 1-bath home surrounded by lush...
From $2,836/night
Kailuana Beachfront Estate: 5 BR Kailua Oceanfront Home
Kailua, Hawaii
★★★★★ 9.6/10 · 41 reviews
Kailuana Beachfront Estate is a fully remodeled luxury retreat on nearly an acre of prime Kailua Beach oceanfront land. Featuring a main home with 3...
From $171/night
New Listing: Spacious Suite for 4x with panoramic ocean view
Kailua, Hawaii
★★★★★ 9.6/10 · 13 reviews
Our Tropical Treasure is situated at a cool 1300' elevation with a "million dollar view" over looking the ocean. The climate is perfect all year...
From $591/night
Kailua Palms Guest House with Pool and Views! Parking and wi-fi included
Kailua, Hawaii
★★★★★ 9.6/10 · 13 reviews
Come bask in the gentle trades of the windward side at the Kailua Palms Estate Guest House, a fabulous two bedroom, two bath vacation guest house...
From $150/night
1 Bdrm Ocean View walk to Turtle Beach, close to Kona Village&Magic Sands Beach
Kailua, Hawaii
★★★★★ 9.6/10 · 11 reviews
Cute one bedroom beach side apartment with ocean view in perfect location, on Ali'i Drive across the street from Turtle Beach. Turtle Beach access 2...
From $461/night
MINUTES TO KAILUA BEACH-FABULOUS POOL great indoor/ outdoor living
Kailua, Hawaii
★★★★★ 9.6/10 · 8 reviews
ABSOLUTELY FABULOUS very large two bedroom two bath house or more.... if you rent the loft which has another HUGE bedroom bath and kitchenette....
From $556/night
Absolutely Oceanfront - 60' Waterfall Lap Pool
Kailua, Hawaii
★★★★★ 9.4/10 · 176 reviews
Kailua Absolutely Oceanfront Deluxe Legal Vacation RentalThe closest house to the Ocean in KailuaLocated in a quiet upscale neighborhood away from...
From $499/night
Ocean View Guest Cottage - 1990/NUC-1797
Kailua, Hawaii
★★★★★ 9.4/10 · 105 reviews
Additional guest fee of $90 per person per day applies to parties over 4 people. Additional service fee and tax will apply.A two-bedroom, one-bath,...
From $670/night
'Star of Hawaii' Beachside, Pool, Steps to Beach - Great for Families
Kailua, Hawaii
★★★★★ 9.4/10 · 99 reviews
To comply with Honolulu vacation rental rules, we only rent once in a 30-day period. You may inquire about a shorter stay if our calendar is open for...
From $1,980/night
Luxury Beach Vacation House in Kailua Beach
Kailua, Hawaii
★★★★★ 9.4/10 · 93 reviews
Additional guest fee of $98 per person per day applies to parties over 10 people. Additional service fee and tax will apply.A private home with eight...
From $157/night
🏖️Excellent Ocean View | AC | Concierge Included | vrKCV
Kailua, Hawaii
★★★★★ 9.4/10 · 85 reviews
vrKCV - Kona Makai 6204, Professionally Managed by Kona Coast Vacations.Experience Oceanfront Living at Kona MakaiNestled along the lava rock shores...
From $125/night
1 bdrm peakaboo ocean view walk to Turtle Beach, Alii Garden Mkt,Kona Village-1D
Kailua, Hawaii
★★★★★ 9.4/10 · 12 reviews
Cute one bedroom beach side apartment with peak-a-boo ocean view in perfect location, on Ali'i Drive across the street from Turtle Beach. We are...
From $650/night
Kailua Beach Estate: Historic Property with Large Yard & Ocean View
Kailua, Hawaii
★★★★★ 9.2/10 · 160 reviews
This Kailua beach estate is a 3-bedroom vacation home on over an acre of land, just one house back from world-famous Kailua Beach. Offering 2,200...
From $295/night
Award Winner - Hawaii's Hidden Hideaway - Bed and Breakfast
Kailua, Hawaii
★★★★★ 9.2/10 · 111 reviews
Hawaii's Hidden Hideaway is an AWARD-WINNING Bed and Breakfast. Recipient for two years in a row the MOST ROMANTIC HIDEAWAY AWARD, voted by its...
From $115/night
RENOVATED Studio By The Ocean!!!
Kailua, Hawaii
★★★★★ 9.2/10 · 64 reviews
Aloha Kakou! Thank you for checking out my unit near the beach. I have a kitchen to test out your cooking skills and a balcony overlooking the pool...
From $625/night
Steps to beach, pool, garden. April/May Cancellation Special. CALL NOW!
Kailua, Hawaii
★★★★★ 9.2/10 · 20 reviews
Minimum 30 day rental, this 3 bedroom, 3 bath with a private pool is the perfect location to relax and unwind. The entire property is surrounded by...
From $131/night
🏖️Ocean View | Close to Pool & BBQ Area | vrKCV
Kailua, Hawaii
★★★★★ 9.0/10 · 105 reviews
vrKCV - Sea Village 2102, Professionally Managed by Kona Coast VacationsOcean View Ground Floor Kona Condo | Walk to Honl'sOcean views, sunset skies,...
From $372/night
Open-Plan Lush Garden Home Near Kailua & Lanikai Beaches
Kailua, Hawaii
★★★★★ 9.0/10 · 89 reviews
Min 30 days requiredLush tropical gardens make this private home into a quiet, comfortable retreat. Large enough for six adults, plus a couple of...
From $293/night
Oceanfront Condo Total Remodel 2025 2 Pools Kona Sunsets Private Lanai A/C
Kailua, Hawaii
★★★★★ 9.0/10 · 71 reviews
TOTALLY REMODELED COMPLETED January 2025!!* New Italian ceramic tile floors & showers.* Solid Bamboo Cabinetry throughout. * Complete new bathrooms...
From $1,180/night
Maluhia: Luxurious Kailua Home w/Pool Oasis, A/C, Near Beaches and Shopping!
Kailua, Hawaii
★★★★★ 9.0/10 · 2 reviews
Let the serene energy of Maluhia draw you into effortless island living. Nestled in the heart of Kailua, Oahu, this two-level private villa blends...
From $145/night
Aloha Lil Hawaiiana 🌺
Kailua, Hawaii
★★★★★ 8.8/10 · 5 reviews
Aloha, a small 400 sq ft studio condo unit is centrally located at the beautiful Kona Islander Inn off Ali'i Drive and Kaukini Highway. Just a few...
From $295/night
Ohana Rental Cottage Close to Beach
Kailua, Hawaii
★★★★★ 8.0/10 · 4 reviews
We live onsite and the house was built as a rental in mind. When facing the building from the street, we are on the left side. You have your own...
From $447/night
Private Luxury Home, Steps from the Beach w/ AC, Ranch Beach House
Kailua, Hawaii
★★★★★ 8.0/10 · 1 reviews
Just steps from the white sand shoreline of Kailua Beach, Ranch Beach House offers a private, garden-surrounded setting designed for relaxed island...
From $122/night
Cozy Lanikai Cottage Walking Distance to the Beach-Near Shops & Restaurants
Kailua, Hawaii
★★★★★ 7.0/10 · 2 reviews
This property requires a minimum 30-day rental. Book with confidence—professionally managed by Ali'i Beach Rentals, an award-winning property...