Vacation Rentals near Kailua Beach

'Kailua Lani Suite' short walk to Kailua Beach. Air conditioned and private.

"In order to comply with Oahu's 30 day minimum short term rental laws, we may not advertise to rent for a period shorter than 30 days."

Come enjoy island life while staying in our newly built, 600 sq. ft. upstairs suite. Beautifully ...

  • 1 bedroom
  • 1 bathroom
  • Sleeps 2
Hawaii> Kailua
from $218 
View Property   Book Now

Kailua Beach Vacation Cottage

*Please read full description!

Sleeping 6, our large private garden cottage is located just 50 steps away from Kailua Beach. The lush garden setting offers a large air conditioned bedroom that sleeps 4 (queen size bed and 2 twin beds), ...

  • 2 bedroom
  • 2 bathroom
  • Sleeps 6
Hawaii> Kailua
from $368 
View Property   Book Now

Large Home With Pool Just Steps to Kailua Beach

Set on a private road with private beach access, Kailua Beachside is One-Story Home a 4BD/4BA (over 2,800 square feet) estate home that has been extensively remodeled and well-cared for. Nestled amongst mature landscaping, the property offers ...

  • 4 bedroom
  • 4 bathroom
  • Sleeps 14
Hawaii> Kailua
from $827 
View Property   Book Now

Amazing & Large Kailua Beachfront for up to 14 guests

Place in Paradise - Kailua offers casual oceanfront accommodations on one of the most beautiful beaches in Hawaii. Kailua Beach has been voted "Best Beach in the United States" by a variety of publications. Five bedrooms and five and half ...

  • 5 bedroom
  • 6 bathroom
  • Sleeps 14
Hawaii> Kailua
from $2,551 
View Property   Book Now

Kailua Beach Hideaway TA-189-305-8560-01

Beachfront! The White Sand of Kailua Beach at Your Door!
This 4 bedroom, 4 bath, en suite home is the Perfect Tropical Haven.
Tucked away and private, this home embodies the true island lifestyle.
Walk or jog the long stretch of beach...

  • 4 bedroom
  • 4 bathroom
  • Sleeps 8
Hawaii> Kailua
from $1,180 
View Property   Book Now

Koi Palms 1 bedroom Cottage - Great location! 5 Minute Walk to Kailua Beach!

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 Kailua. The owners live on the property in the main house.
The cottage is a 600 square foot 1 ...

  • 1 bedroom
  • 1 bathroom
  • Sleeps 2
Hawaii> Kailua
from $306 
View Property   Book Now

Steps To Kailua Beach


Our beautiful home has been featured in Hawaii Home Magazine and has received a best in class award from the Hawaii Builders Association. The home is within a 2 minute walk to Kailua Beach Park, the Kalapawai Market and Buzz's Steak ...

  • 4 bedroom
  • 4 bathroom
  • Sleeps 7
Hawaii> Kailua
from $720 
View Property   Book Now

Awesome Beachside Cottage Located Just Steps Away from Kailua Beach

Tropical setting just steps away from beautiful Kailua Beach. Located on a quiet cul-de-sac beachside of Kalaheo Ave. This quiet and private accommodation is ideal for 2 couples or a small family. Aprox 900sq ft of indoor living area, complete ...

  • 2 bedroom
  • 2 bathroom
  • Sleeps 4
Hawaii> kailua
from $351 
View Property   Book Now

Family friendly Quiet Kailua Beachside lane, steps to lane private beach access

Only steps to beach through private street gate, and a short 1.5 mile bike to Kailua town. 2 bedrooms, family room, and kitchen on 2nd floor; laundry, 1 bedroom and bath on 1st floor. Washer/Dryer, Basic Cable, and Wifi includded. Small pets ok....

  • 3 bedroom
  • 2 bathroom
  • Sleeps 4
Hawaii> Kailua
from $340 
View Property   Book Now

Steps to Kailua Beach- Heated Pool- Air Conditioned-CONTACT HOST One Week Stay

VIEW ONLINE CALENDAR
UNBLOCKED DAYS ARE AVAILABLE
CONTACT HOST/RESERVATION REQUEST

Hale Kea is a newly renovated Hawaiian-style home designed for casual living and family entertainment; just steps to beautiful Kailua ...

  • 3 bedroom
  • 3 bathroom
  • Sleeps 5
Hawaii> Kailua
from $494 
View Property   Book Now

Best Price and Location on Beautiful Kailua Beach!

The upstairs and downstairs beach front studios..My beach front studios for 2 guests are located right on beautiful sandy Kailua Beach. they are quiet with private entrances and private bathrooms, modern, spacious and tastefully furnished. The ...

  • 2 bedroom
  • 1 bathroom
  • Sleeps 2
Hawaii> Kailua
from $317 
View Property   Book Now

Ohana Beach House - 5 Bedrooms - Steps Away from Kailua Beach

Just steps from one of the most beautiful tourist-free beaches on the island of Oahu, this Hawaiian style home is a perfect peaceful getaway for your extended family. Listen to the waves crashing as you relax on the lanai, or barbeque for your ...

  • 5 bedroom
  • 3 bathroom
  • Sleeps 10
Hawaii> Kailua
from $1,142 
View Property   Book Now

Fabulous Luxury Kailua Beachfront Private pool and Hot Tub

VIEWS!! Absolutely beautiful right on Kailua beach with pool and spa .

Six bedrooms of beach-front paradise in Kailua. Swimming pool, hot tub, game and TV room make this property an ideal vacation recreation ...

  • 5 bedroom
  • 5 bathroom
  • Sleeps 12
Hawaii> Kailua
from $1,829 
View Property   Book Now

Quiet, Private, Beachy 2-bedroom, Walk to Kailua Beach, A/C

Pacheco's Hale is a beautiful two-bedroom, second-floor unit - nice and breezy with a private entrance. We have been renting our property since the 1980s and this unit since 2014. This clean, quiet unit is completely furnished and updated ...

  • 2 bedroom
  • 2 bathroom
  • Sleeps 4
Hawaii> Kailua
from $271 
View Property   Book Now

World Famous Kailua Beach Charming Cottage

Studio Cottage near Kailua Beach and Beach Park! Large, 200 square foot lanai, fully furnished. Nice neighborhood setting. You won't believe how close this is to the beach! Also close to Kalapawai Market and other Beach Shops & Food. All ...

  • 1 bedroom
  • 1 bathroom
  • Sleeps 2
Hawaii> Kailua
from $103 
View Property   Book Now

🌺 Charming Apartment in Prime Location – Steps from Kailua Beach & Town 🌺

500 square feet Apartment with 10 foot ceilings, comes with queen bed in separate bedroom, queen size pull out sofa bed in living room with memory foam mattress, washer dryer, full equipped kitchenette, free parking and free Wifi. We offer a ...

  • 2 bedroom
  • 1 bathroom
  • Sleeps 3
Hawaii> Kailua
from $136 
View Property   Book Now

Amazing 🌺 Kailua Beach House 🌺 Pool! Game Room! 1 House from Beach

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 house from the white sands of Kailua beach (Private beach gate is located adjacent to our ...

  • 5 bedroom
  • 4 bathroom
  • Sleeps 10
Hawaii> Kailua
from $1,071 
View Property   Book Now

Spectacular Kailua Beachfront w/Heated Pool/Spa~ THANKSGIVING OPEN!

Recently updated with stylish contemporary design, this spacious Kailua home sits on Kailua Beach with nearly 100 linear feet of beach frontage. The home features direct and private access to the white sands with over 2 miles of beach walking ...

  • 6 bedroom
  • 7 bathroom
  • Sleeps 14
Hawaii> Kailua
from $2,566 
View Property   Book Now

Kailua Beach Cottage with A/C

100% Kailua Lifestyle.

In Jan 2022, we resumed renting this cottage as a vacation rental. (We stopped in March 2020 due to COVID).

Previously, this property was listed on another vacation rental platform. We achieved ...

  • 2 bedroom
  • 1 bathroom
  • Sleeps 2
Hawaii> Kailua
from $292 
View Property   Book Now

Kailua Beach Lofty Bungalow - A premier luxury beachside bungalow

Kailua's Lofty Bungalow is a premier private luxury bungalow getaway - Modern design mingles with traditional elegance in this newly built bungalow. Beautifully furnished with comfort and ease. Open floor plan that features floor to ceiling ...

  • 1 bedroom
  • 1 bathroom
  • Sleeps 2
Hawaii> Kailua
from $513 
View Property   Book Now

Custom, Renovated Kailua Beach Front w/pool - Best Location on the Bay!

One of the few Licensed Short-Term Vacation Rentals on the Windward side of Oahu, this three bedroom, three bath home with large swimming pool sits on .9 acres of Kailua Beachfront. The home has been recently refurbished with new furnishings, ...

  • 3 bedroom
  • 3 bathroom
  • Sleeps 10
Hawaii> Kailua
from $2,880 
View Property   Book Now

Beachfront spectacular Kailua beach

Aloha from Kailua; we must do a 30-day minimum on our rental home until otherwise noted. Please don’t let this affect where you wish to vacation. Although I have to rent in a 30-day minimum this is not normally 1st through the 30th. Calendar ...

  • 4 bedroom
  • 2 bathroom
  • Sleeps 8
Hawaii> Kailua
from $2,037 
View Property   Book Now

Kailua Beach/Lanikai LUX apartment w/Ocean Views from Rooftop Sun Deck

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 private lane. Ocean, park and Mountain view’s are captured from the rooftop sun deck. ...

  • 1 bedroom
  • 1 bathroom
  • Sleeps 2
Hawaii> Kailua
from $156 
View Property   Book Now

Steps from Kailua Beach, heated pool, gazebo, AC, NO CLEANING FEE!

This stylish, designer decorated, 4 bed, 4 Bath home is just across the street from Kailua Beach. We call her Coastal Soul. Lounge in the beach chic living room, cook in the gourmet, fully equipped kitchen, or swim in the heated lagoon pool. ...

  • 4 bedroom
  • 4 bathroom
  • Sleeps 8
Hawaii> Kailua
from $1,155 
View Property   Book Now

Hale Aloha: Luxe Waterfront Home, Island Vibe, Private Pool, Near Kailua Beach

Unwind at Hale Aloha by Gather, your tranquil retreat just minutes from Kailua’s famous shores. This 4-bedroom, waterfront sanctuary on a sprawling 12,000 SF combines contemporary ease with island living, presenting a lush oasis, ample spaces ...

  • 5 bedroom
  • 2 bathroom
  • Sleeps 10
Hawaii> Kailua
from $1,324 
View Property   Book Now

New Discounted Rates for Apirl & May ! Steps to Kailua beach!

This is a legally established property, please read more below...

Our Hawaiian-style 3 bedroom 3 bath vacation home is just steps from the sand of beautiful Kailua Beach on the island of Oahu. Hear the sounds of the surf at night and the ...

  • 3 bedroom
  • 3 bathroom
  • Sleeps 8
Hawaii> Kailua
from $558 
View Property   Book Now

Kailua Beachside Studio - Tropical Breeze

This is a legally established property, please read more below

Serene tropical comfort in your own private studio, just steps away from 1 of the top 5 best beaches in the world. Here you can walk for miles on a white, sandy beach or go ...

  • 1 bedroom
  • 1 bathroom
  • Sleeps 2
Hawaii> Kailua
from $372 
View Property   Book Now

Just steps to Kailua Beach with private pool

With access to the world-famous Kailua Beach and its turquoise waters being just four houses away and shops, restaurants and grocery nearby, the location of Helen's Beach House could not be more ideal. The exterior maintains a modest aesthetic, ...

  • 5 bedroom
  • 5 bathroom
  • Sleeps 12
Hawaii> Kailua
from $572 
View Property   Book Now

Zen Home with AC, Pool, Near Kailua Beach

Spend your vacation in our Hawaiian style 4 bedroom, 4 bathroom home a 3 minute walk from Kailua Beach. Our home features a balance of indoor and outdoor living. There is a zen like courtyard and inviting navy blue mosaic swimming pool in the ...

  • 4 bedroom
  • 4 bathroom
  • Sleeps 12
Hawaii> Kailua
from $1,007 
View Property   Book Now

Secluded Home w/ Pool in Gated Community, Steps From Beautiful Kailua Beach

Our 2,600+ square foot home is the perfect balance between luxury and laid-back comfort. The property has marble floors, tall ceilings, brand new appliances and stylish furnishings. The two master bedrooms (one upstairs, one downstairs) are ...

  • 4 bedroom
  • 4 bathroom
  • Sleeps 8
Hawaii> Kailua
from $911 
View Property   Book Now

Kailua Beach "The Pink House" 100 Yards from Ocean

The Pink House is a perfect beach house set 100 yards from beautiful Kailua Beach. This Hawaiian Style Home has an open floor plan that includes a combination living/dining area with a galley kitchen with stainless steel appliances. Recently ...

  • 4 bedroom
  • 2 bathroom
  • Sleeps 6
Hawaii> Kailua
from $761 
View Property   Book Now

Huge House, Heated Pool, AC, Steps to Kailua Beach

Spacious, resort-style residence located within 100 yards of Kailua Beach. Featuring a private courtyard and pool, this indoor/outdoor floor plan is ideal for family gatherings. The extensive renovation features an expansive master suite, a ...

  • 8 bedroom
  • 5 bathroom
  • Sleeps 20
Hawaii> Kailua
from $1,394 
View Property   Book Now

Close to the Beautiful Kailua Beach-A/C's-Full Kitchen-Covered Patio-Pet ok

This large 700 square foot rental unit called the 'Coconut Corner' is one of the nicest rentals you will find on the Windward side of Oahu — a king size bed, full split A/C in every room and Smart TV's in both the bedroom and the living room, ...

  • 2 bedroom
  • 1 bathroom
  • Sleeps 4
Hawaii> Kailua
from $285 
View Property   Book Now

Experience the Beauty of Paradise, Stunning Gardens, Steps from Kailua Beach

Welcome to Alohawaii Properties by the Sea, a registered legal transient accommodations operator with license 90/BB-0013 and registration number GE-039-001-2928-01, TA-039-001-2928-01. We are delighted to share that we have been named the winner...

  • 2 bedroom
  • 2 bathroom
  • Sleeps 5
Hawaii> Kailua
from $643 
View Property   Book Now

Less than a one minute walk to Kailua Beach, Pool, Bikes, BBQ, A/C, and more

Welcome to Alohawaii Properties by the Sea, a registered legal transient accommodations operator with license 90/BB-0013 and registration number GE-039-001-2928-01, TA-039-001-2928-01. We are delighted to share that we have been named the winner...

  • 1 bedroom
  • 1 bathroom
  • Sleeps 2
Hawaii> Kailua
from $375 
View Property   Book Now

MINUTES TO KAILUA BEACH-FABULOUS POOL great indoor/ outdoor living

ABSOLUTELY FABULOUS very large two bedroom two bath house or more.... if you rent the loft which has another HUGE bedroom bath and kitchenette. .
Sparkling pool in a private courtyard in the back yard VERY PRIVATE.
Asian inspired ...

  • 2 bedroom
  • 2 bathroom
  • Sleeps 4
Hawaii> Kailua
from $414 
View Property   Book Now

Perfect Location on Kailua Beach - Licensed Short Term Rental

Island living at its finest, this casual Kailua beachfront home is located on the Windward side of Oahu, 30 minutes from Honolulu and approximately 1 mile from the center of Kailua Town. Enjoy spectacular sunrises over Kailua Bay, the scenic ...

  • 5 bedroom
  • 4 bathroom
  • Sleeps 10
Hawaii> Kailua
from $2,516 
View Property   Book Now

Tropical Studio w/ pool, spa, a/c, WFH, walk to Kailua Beach (30 day Discount!)

Final Bookings must be 30 consecutive days or more. Send us a message to inquire about rates!

Stroll along the white sandy beaches of Lanikai Beach, named one of the top 10 beaches in the world by 2014 Travelers Choice! Only a 5 minute ...

  • 1 bedroom
  • 1 bathroom
  • Sleeps 2
Hawaii> Kailua
from $219 
View Property   Book Now

Less than 1 min walk to Kailua Beach- NUC#90/BB -0013

Welcome to Alohawaii Properties by the Sea, a registered legal transient accommodations operator with license 90/BB-0013 and registration number GE-039-001-2928-01, TA-039-001-2928-01. We are delighted to share that we have been named the winner...

  • 2 bedroom
  • 2 bathroom
  • Sleeps 5
Hawaii> Kailua
from $622 
View Property   Book Now

KAILUA BEACH VILLA - 1990/NUC-1798

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 bedrooms on Kailua Beach (Voted Number One Beach in America). (Adjacent 2-bedroom Guest ...

  • 8 bedroom
  • 5 bathroom
  • Sleeps 14
Hawaii> Kailua
from $2,464 
View Property   Book Now

Beachfront Plantation Cottage - 3sqm / 2sqm House - Kailua Beach

Within half an hour of Honolulu International Airport and Waikiki, this quaint beach house sits on one of the most beautiful beaches in the state of Hawaii - Kailua- miles of white sand, with water sports, dining, sunrise and sunset beach walks,...

  • 3 bedroom
  • 2 bathroom
  • Sleeps 7
Hawaii> Kailua
from $646 
View Property   Book Now

🌴Exquisite Studio in Best Location 🌴 Steps from Kailua Beach 🌴

Your Tropical Oasis Steps from the Beach

Escape to our large, peaceful studio with cathedral ceilings and a private yard, just steps away from the beach on a private lane. Accommodating up to 2 guests, the room features a king-size bed ...

  • 1 bedroom
  • 1 bathroom
  • Sleeps 2
Hawaii> Kailua
from $146 
View Property   Book Now

Close to Kailua Beach-AC's-Renovated/Upgraded-Fenced Backyard-Patio-Pet ok

This is a fully furnished & renovated/updated 3/2 rental with a big, fenced & shady yard with tropical trees and plants, including mango, breadfruit, lemon, lime, coconut, avocado, tangerine, lychee & dragon fruit. You'll love cooking in this ...

  • 3 bedroom
  • 2 bathroom
  • Sleeps 7
Hawaii> Kailua
from $810 
View Property   Book Now

Kailua Beachside - 5-Bedroom/6-Bath (Sleeps 10) - 5,000 sft., Steps to Beach

E Komo Mai! Welcome to our newer 5-bedroom/6-bath private home, located in the desirable windward town of Kailua, Oahu. This beachside residence is within close walking distance to a 3-mile stretch of one of the best swimming beaches on Oahu....

  • 5 bedroom
  • 6 bathroom
  • Sleeps 10
Hawaii> Kailua
from $375 
View Property   Book Now

Luxury Home in Gated Community Steps from Kailua Beach

This spacious and elegant home is the perfect balance between luxury and laid-back comfort. The way it transitions from indoor to outdoor provides the best setting in which to enjoy Hawaii's serene environment. Not to mention it's convenient ...

  • 4 bedroom
  • 4 bathroom
  • Sleeps 10
Hawaii> Kailua
from $840 
View Property   Book Now

Loft In Kailua - Spacious with Parking, Internet and minutes to Kailua Beach!

MINUTES TO KAILUA BEACH AND TOWN!!

This well appointed one bedroom split level loft apartment is beautifully furnished with high ceilings and open floor plan. The upstairs has a shuttered master suite with queen bed, a huge en-suite full...

  • 1 bedroom
  • 2 bathroom
  • Sleeps 1
Hawaii> Kailua
from $337 
View Property   Book Now

Beach House steps from Kailua Beach

Enjoy the close proximity to Kailua Beach/Beach Park and Lanikai in this spacious, well-appointed beach house, steps from the sand, beach toys included! Kayak or paddle board out to The Mokes or Flat Island, boogie board or relax in the sand on...

  • 2 bedroom
  • 3 bathroom
  • Sleeps 5
Hawaii> Kailua
from $325 
View Property   Book Now

Kailua Beach Villa: Stunning Beachfront Estate Private Pool/Spa, Ocean View & AC

Prices start at $45,000/month and will not be pro-rated based on length of stay. Please inquire to get an accurate quote.

Welcome to Kailua Beach Villa, the perfect luxury Hawaiian home for your next beachfront getaway. This large, ...

  • 5 bedroom
  • 5 bathroom
  • Sleeps 12
Hawaii> Kailua
from $2,901 
View Property   Book Now

Kailua Beach Getaway

One bedroom one bath apartment with separate entrance in coconut grove. Walking distance to everything. Quiet neighborhood with free parking in the driveway. 500 square feet of space with full kitchen and bathroom. Shared laundry, gym, and ...

  • 1 bedroom
  • 0 bathroom
  • Sleeps 4
Hawaii> Kailua
from $200 
View Property   Book Now

Seahorse Beach House: Calm Oasis w/ Private Yard Just Steps from Kailua Beach

Seahorse Beach House is a hidden Hawaiian gem, just steps away from Kailua’s powder white sand beaches. Located on one of Kailua’s most coveted loops, you will find its location ideally accessible to numerous cafés, boutiques and farmers’...

  • 2 bedroom
  • 2 bathroom
  • Sleeps 4
Hawaii> Kailua
from $638 
View Property   Book Now

Showing 1 of 2 pages.