Vacation Home Rentals By Owner In Kailua, HI

Live the beach life! An opportunity to live across the street from Kailua Beach Park, with the perfect combination of sandy beach, large grassy areas, tall ironwood trees, and turquoise-blue waters. You will love this generous ground-level one-bedroom, one-bathroom home. Private and separate from the main house with ample living area, bathroom, large kitchen area & outdoor patio, for indoor-outdoor living. The quiet split AC's, tile flooring and covered parking make this a comfortable beach rental.brThere are two split A/C units, double-paned windows, an outdoor grill area and covered parking. Easy walk to Buzz’s Restaurant or Kalapawai Market.brbrAmenities at Kailua Beach Parkbr• Parkingbr• Public bathroomsbr• Beach showersbr• Picnic tables and picnic sheltersbr• Volleyball courtsbr• BBQ pitsbr• Lifeguardsbr• Boat rampbrGuest accessbrGuests will have use of half the carport. There's a shared outdoor grill and outdoor shower for rinsing off after a day at the beach.brbrThis property is a legally established dwelling that is rented for periods of 30 consecutive days or more at any one time. There will be a $50 change fee for any changes made to a reservation that's initiated by the guest after booking.

Short walk to Kailua Beach across the street-Quiet AC's-Lg. Kitchen-Patio-Grill

Kailua, Hawaii, United States

Bed

Bath

Sleeps

$3168.79

This property is professionally managed by Private Homes Hawaii, LLC, a licensed brokerage in the State of Hawaii (RB-21170). It is licensed as a short term vacation rental, Non-Conforming Use Permit Numbers 1990/NUC-1777/1778 and is compliant with Hawaii State Legislation (HB2078) for vacation rental accommodations, brLic#TA-137-826-1504-01. TMK.brbrThis spectacular beachfront home offers two living spaces on the best part of Kailua Beach - known throughout the State as one of the most pristine white sand beaches - the perfect beach home for accommodating groups large and small. Both the main house (5 bedrooms) and the cottage (1 bedroom) have been extensively renovated by professional designers bringing new comforts to even the most discriminating travelers. Open living rooms invite natural light into the house, illuminating the rich wood furnishings and sleek granite countertops. The large, open kitchen and dining area are a chef's delight - with large bar counters and a variety of dining areas - indoors and out. With floor-to-ceiling windows in multiple rooms, and the sounds of the waves hitting the shoreline, the experience is like no other. brbrThe Bedroom Configurations Are As Follows:brBedroom 1 - (Primary Bedroom) King Bed, ensuite bathroom with shower and free-standing soaking tub, TV, split ACbrBedroom 2 - Queen Bed, ensuite bathroom with shower, TV, split ACbrBedroom 3 - King Bed, TV, split ACbrBedroom 4 - King Bed, TV, split ACbrBedroom 5 - Two Twin Beds, TV, split ACbrbrBedroom 6 (Cottage) - Queen Bed and pull out couch in living room, TV, split ACbrbrSmart TV located in Main House Living RoombrbrThis fully air-conditioned home is well equipped with barbecues, sunning lanai, private parking, double washing machines and dryers, beach towels, beach chairs, outdoor showers and more. brbrYour visit to Kailua offers something for everyone:brEnjoy Kailua Beach Park, rent kayaks or stand up paddleboards from Kailua Beach Adventures, take a kite-surfing lesson, sip morning coffee from Kalapawai Market, feast on lunch or dinner at Buzz's Original Steakhouse, explore a variety of nearby hiking trails, and visit the many restaurants and retail shops of Kailua Town, just a mile away. Or tour the island to see famous surfing spots from Waikiki to Waimea Bay and the Banzai Pipeline. Cultural sites, Pearl Harbor, Punchbowl National Cemetery and Diamond Head Crater are all a short drive from this part of the island. And the exciting nightlife of Honolulu is also just 35 minutes away.brbrNote; this property is for quiet residential vacation accommodations only. Parties, weddings, receptions, Luaus, events and gatherings of any kind are prohibited. Please inquire further with our agents.

Hale Oahu Estate Lic. #1990/NUC-1777 BEACHFRONT KAILUA

Kailua, Hawaii, United States

Bed

Bath

Sleeps

$775.37

Live your best life! An opportunity for beach living in this renovated and updated luxury rental with views of Kailua Beach and Kailua Beach Park - it's brilliant turquoise blue ocean, sandy beach, large grassy areas and tall ironwood trees. Fine craftsmanship abounds with attention to detail throughout the rental. The elegant kitchen has mahogany cabinetry, Travertine flooring, Thermador appliances and a huge granite island.brThis rental is directly across the street from Kailua Beach Park and a very short walk, 60 seconds, to the beach. Each of the 3 bedrooms has its own en-suite bathroom. There are two central a/c units, double-paned windows, an outdoor grill area, an outdoor shower and covered parking. Easy walk to Buzz’s Restaurant or Kalapawai Market.brbrAmenities at Kailua Beach Parkbr• Public Free Parkingbr• Public Bathroomsbr• Beach Showersbr• Picnic Tables and Picnic Sheltersbr• Sand Volleyball Courtbr• BBQ charcoal pitsbr• Lifeguardsbr• Boat rampbrThis property is a legally established dwelling that is rented for periods of 30 consecutive days or more at any one time. There will be a $50 change fee for any changes made to a reservation that's initiated by the guest after booking.

Cool retreat at the entrance to Lanikai-Very Close to Beach-3 Primary Bedrooms

Kailua, Hawaii, United States

Bed

Bath

Sleeps

$459.52

Two bedroom, two bath private residence at the top of Lanikai with spectacular, panoramic views of the Kailua coastline. Feel on top of the world in this truly unique hilltop bungalow. Nestled just beneath the Lanikai Pillboxes, a popular hiking trail, Ko’oho’o provides unobstructed views of the Mokulua Islands and the deep blue Pacific beyond. A large lanai provides the perfect outdoor space to soak in colorful sunrises and to entertain your guests. Enjoy the fragrant plumeria trees and tropical foliage just off your lanai. brbrThe lower living area features a fully-equipped kitchen, walk-in pantry, dining nook, living room, laundry room, full bathroom with deep-soaking ‘clawfoot' tub, and guest room with two extra-long twin beds. brbrUpstairs, the luxurious primary suite includes a walk-in closet and wet bar, an updated spa-like bathroom with walk-in shower, copper-wrapped soaking tub, double sinks, and a magnificent, unobstructed view of the ocean. This 400 sq ft suite also includes a large desk space with endless views - ideal for those who must check in with the office. The home is equipped with complimentary high-speed internet access and a large flat-screen Smart TV.brbrThe Bedroom configurations are as follows:brUpper Floor:brBedroom 1 ( 400 sq ft primary suite) - King bed, ensuite bathroom, office space, AC and ceiling fan, with ocean viewsbrbrLower Floor:brBedroom 2 - Two extra-long Twin beds, AC and Ceiling fan, with ocean viewsbrLiving Room - Queen sofa bed, AC and Ceiling fan, TV, with ocean viewsbrbrNearby the property, you will find Lanikai Park and easy access to Lanikai Beach - featured in many publications as one of the best beaches in the world and just a block and a half away. Stroll down 1/2 mile to the sugary-white sand beach and take a dip in the warm, calm, aqua-blue waters of this idyllic setting. brbrYour visit to Lanikai offers something for everyone:brEnjoy Kailua Beach Park, rent kayaks or stand-up paddleboards from Kailua Beach Adventures, take a kite-surfing lesson, sip morning coffee from Kalapawai Market, feast on lunch or dinner at Buzz's Original Steakhouse, explore a variety of nearby hiking trails, and visit the many restaurants and retail shops of Kailua Town, approximately 2 miles away. brbrNOTE: pets will be considered with certain restrictions including a mandatory pet deposit. Please inquire further with our reservations team.brbrThis Property is professionally managed by Private Homes Hawaii, LLC, a licensed brokerage in the State of Hawaii (RB-21170). It is an accommodation that is rented for periods of 90 consecutive days or more at any one time. It is compliant with Hawaii State Legislation (HB2078) and is available to lease from 90-days to 6 months: Lic#TA-073-725-6960-01. TMK.

Koohoo Place - Lanikai, Oahu. From here, you can see forever! NEW LISTING.

Kailua, Hawaii, United States

Bed

Bath

Sleeps

$1187.12

Beachfront! The White Sand of Kailua Beach at Your Door!brThis 4 bedroom, 4 bath, en suite home is the Perfect Tropical Haven.brTucked away and private, this home embodies the true island lifestyle.brWalk or jog the long stretch of beach or lounge by the pool, with greatbrrestaurants and shopping just a mile away, like living at a mini-resort!brFully furnished and equipped, in very tropical Baliesque style...all you need are your personal favorite swim suits and a good book.brThree Bedrooms have air conditioning, the rest of the house is dependent on tropical breeze and the hot tub in the pool does not function as a hot tub with jets, so the new heater ended up being a pool heater...Bonus!brbrPlease Be Aware that this platform does Not charge a Security Deposit or a Cleaning Fee. These will be addressed with the agent prior to Confirming a Stay and there will be a fee for these outside of the VRBO platform.brbrThis property may not be rented for less than 30 consecutive days. Rental prices will not be reduced or adjusted based on the number of days the rental is actually used or occupied. TMK: 43017075br

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

Kailua, Hawaii, United States

Bed

Bath

Sleeps

$240.1

For questions, to verify availability dates or to check the availability of other furnished rentals we manage, please contact the owner.br brThis 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, a fully upgraded kitchen with solid surface countertops, custom cabinetry, stainless steel fridge, range/oven, mircohood & dishwasher plus a covered patio with a table and chairs with ceiling fans throughout the rental, free parking right out front along with free laundry and WiFi. This large vacation rental is in a quiet residential neighborhood just a half-mile from an access to the beautiful sandy 2 mile stretch of Kailua Beach. This duplex is close to Kailua Town and the neighborhood Aikahi Park Shopping Center with restaurants, hair/nail, liquor/poke store, coffee shop, bank, gas station and a grocery store all within walking distance. brbrKailua is a friendly town of about 38,000 located on the beautiful northeast shore of Oahu. I love Kailua for its many beaches and accessible off-shore islands. The beautiful two-mile stretch of sparkling Kailua Beach and adjoining Lanikai have been rated tops among America’s best beaches. Surf shorebreak, kayak, swim with the green sea turtles, or sail to one of the secluded offshore islands and maybe spot the whales breech offshore. It does not get any better than this!brbrIt is only a 20-25 minute scenic drive to the airport, Honolulu, and Waikiki. Nearby sites include Kailua Beach Park, Kailua Farmers Market, Lanikai Pillbox hike, Maunawili Falls, Sea Life Park, Sandy Beach, Waimanalo, Hanauma Bay, and the North Shore. brbrKailua town offers many diverse restaurants and shopping locations. There are businesses that offer kayaks, kite surfing, and wind surfing lessons and rentals. There are wonderful hiking trails nearby and waterfalls. brbrKailua offers a completely different atmosphere from the hustle and bustle of Waikiki. Many of our guests enjoy the laid back atmosphere, sense of community, and Aloha Spirit we all share. Also, enjoy making your own meals in the full kitchen, even firing up the stainless gas grill to cook up some special dinners. brbrThis rental is smoke free and we ask that our smoking guests smoke beyond the property lines only in the street.brbrA $50 reservation change fee will apply to any changes to an existing reservation initiated by guests.

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

Kailua, Hawaii, United States

Bed

Bath

Sleeps

$666.0

Located just steps from the best part of Kailua Beach. The beach is a short walk through Kailua Beach Park where the waves are the most gentle, the sand is wide, and there are plenty of trees for shade, so you and the kids can play and relax at the beach all day. brbrThis home was thoughtfully designed to meet the needs of families. It has a large great room where all can congregate for meals, plan the day, wind down after a full day of activities or just relax. A delicious breeze will soothe your soul as you open the large glass sliders, revealing lush gardens and the pool. brbrThe two master suites are at opposite ends of the home and on separate floors, so that two families can enjoy each other's company, yet still have their own private retreat.brbrThe bathrooms are finished with hand cut stone, oil rubbed bronze fixtures, and frameless glass shower doors in a style reminiscent of a natural Hawaiian spa.br brThe home has a monitored security system and is a legal dwelling rented for a period of 30 days; ask owner for additional available dates.brbrbrbr

Kahela - Paradise for Rent

Kailua, Hawaii, United States

Bed

Bath

Sleeps

$1208.49

Nestled in the coveted Lanikai community of Kailua, Hale Nani Lanikai invites you to experience authentic island living in a refined, serene setting. This modern retreat accommodates up to eight guests across three spacious bedrooms—each with its own ensuite bathroom—ensuring comfort, privacy, and effortless relaxation. Whether you're enjoying a refreshing dip in the heated pool or savoring morning coffee on the covered lanai, this home offers an idyllic escape just minutes from world-famous Lanikai Beach.brbrWhat You’ll Love About Hale Nani Lanikaibr• Expansive private heated pool for sun-soaked afternoonsbr• Elegant open floor plan providing seamless indoor/outdoor livingbr• Beautiful granite kitchen with generous seating for gatheringsbr• Covered lanai ideal for sunrise rituals and evening unwindingbr• Lush garden views and glimpses of the dramatic Kaʻiwi Ridge LinebrbrLiving & DiningbrNatural light fills the open living areas, creating a vibrant, connected space for families and friends to gather. The family room features custom monkeypod wood furnishings and inviting garden views, offering a peaceful setting for conversations, reading, or movie nights.brbrChef-Ready KitchenbrPrepare meals with ease in the fully equipped kitchen, showcasing granite countertops, stainless steel appliances, and everything from a coffee maker to a blender. Whether you're crafting a sit-down dinner or a post-beach brunch, this kitchen makes cooking a pleasure.brbrOutdoor OasisbrThe covered lanai extends your living space and offers a breezy sanctuary surrounded by tropical landscape. Enjoy outdoor dining, lounge between pool dips, or simply relax as soft ocean breezes accompany the views of Kailua’s natural beauty.brbrSleeping Quartersbr• Primary Suite – King bed, ensuite bath with deep soaking tub + walk-in shower, garden viewsbr• Guest Bedroom 2 – Double bed, ensuite bathbr• Guest Bedroom 3 – King bed, ensuite bathbrbrExtrasbrEnhance your stay with thoughtful amenities including split air conditioning throughout, high-speed Wi-Fi, a washer and dryer, and beach gear (chairs, umbrellas, boogie boards) to support your island adventures.brbrResort / Community HighlightsbrLocated just moments from some of Oahu’s best beaches and outdoor attractions, Hale Nani Lanikai is surrounded by opportunities for hiking, snorkeling, kayaking, and exploring Kailua’s charming local shops and eateries.br brNearby – Walk:br• Kailua Beachbr• Local cafés, markets, and shopsbrNearby – Short Drive:br• Iconic Lanikai Beachbr• Pillbox hiking trail with unforgettable sunrise viewsbrbrGood to Knowbr• Rates and fees are subject to change. Minimum stay requirements may apply. Inquire for possible discounts.br• Online bookings are subject to manager or owner approval.br• A/C Notes: Split AC in each bedroom & common living area of the home.br• The property will be made exclusively available to the renter for a full period of 30-days and no one else may occupy the property during that period.br• Max Included Electric Charge: $400/month (This is very reasonable because the home has photovoltaic)br• Tax ID: TA-209-884-5696-01br• TMK 430050050000brbrReserve your dates now while your preferred month at Hale Nani Lanikai is still available. Discover the perfect balance of luxury, comfort, and authentic island living—your Hawaiian retreat awaits.

Hale Nani Lanikai: Beautiful Tropical Home Close to Beach w/Pool, Yard & AC

Kailua, Hawaii, United States

Bed

Bath

Sleeps

$1021.49

Discover your private island retreat at Charming Cottage in Lanikai by Gather, a beautifully renovated 1-bedroom, 1-bath home surrounded by lush tropical gardens. Fully remodeled in 2021, this peaceful hideaway blends modern comfort with the timeless charm of Lanikai’s coastal lifestyle—just a short stroll from one of Oahu’s most beautiful beaches.brbrWhat You’ll Love About This Lanikai Cottagebr• Newly renovated in 2021 with brand-new furnishings and appliancesbr• Peaceful tropical setting with privacy and lush garden viewsbr• Bright and airy interior with an open-concept living space and efficiency kitchenbr• Expansive lanai for outdoor dining, lounging, and barbecuesbr• Small pool with a gentle waterfallbr• Outdoor shower for rinsing off after the beachbr• Split A/C unit for quick and quiet coolingbr• Washer and dryer located just outside the cottage for your conveniencebrbrLiving & DiningbrStep into a bright, welcoming space designed with island-inspired decor and contemporary finishes. The open floor plan connects the cozy living area to the efficiency kitchen, offering everything you need for simple meal preparation. Large sliding doors open onto the lanai, where you can dine al fresco or relax with a cool drink amid the tropical breeze.brbrEfficiency KitchenbrCompact yet thoughtfully designed, the efficiency kitchen includes a 2-burner induction hotplate, microwave, multi-function toaster oven, mini refrigerator and freezer, and essential cookware. An outdoor gas grill expands your cooking options, making it easy to enjoy casual island-style meals at home.brbrOutdoor OasisbrThe expansive lanai extends your living area into the island’s natural beauty, perfect for barbecues, morning coffee, or sunset relaxation. A small pool with a gentle waterfall invites you to unwind after a day at the beach, while the outdoor shower provides the perfect refresh under Hawaii’s warm skies.brbrSleeping Quartersbr• Primary Bedroom – Queen bed, ceiling fan, ensuite bath with walk-in showerbrbrGood to Knowbr• Important Note: Main House on Property (Occasional Family Use)Please note that there is a main house on the property that is sometimes used by the owner/family. During your stay, you may see the owner/family present on the property at times. If you have any privacy-related questions before booking, please reach out—we’re happy to clarify.br• Ideal for 2 adults (maximum 3 adults, or 2 adults and 2 children)br• Small pool (10x20 ft, 6 ft deep) with waterfall featurebr• Quiet residential neighborhood—please respect community serenitybr• Short walk to Lanikai Beach and the famous Mokulua Island viewbr• Licensed short-term vacation rental – Non-Conforming Use Permit NUC# 90/TVU-0325br• Hawaii Tax ID: TA-006-174-7200-01br• TMK: 430040610000brbrWhether you’re basking in the sun on Lanikai’s powdery sands, cooling off in your pool, or dining on the lanai surrounded by tropical greenery, Charming Cottage in Lanikai by Gather offers an unforgettable blend of comfort, privacy, and island tranquility. Relax, unwind, and experience the true spirit of Hawaii in your own serene coastal retreat.

Quaint Tropical Cottage w/Pool, Lanai & AC, Walk to Beach: Lanikai Ohana Hale

Kailua, Hawaii, United States

Bed

Bath

Sleeps

$186.4

Attractive, ground floor, 2 bedroom 1 bathroom unit with a separate living room and private entry. Located on the island of O’ahu, you'll find comfort and relaxation here while on vacation. A 6-8 minute walk to the world famous Kailua Beach. The exciting night life of Waikiki is a short 25 minute drive away. The Tradewind Bungalow is the ideal location while vacationing in Hawaii. All the rooms have been repainted and feature newer wood laminate flooring throughout. The large kitchenette is brand new as of August 2024.brbrThe first bedroom is 11 by 12 sq. ft. and has a queen size bed, a dresser, a window AC and a large closet This bedroom also accesses the outside lanai. This bedroom is also the most private and quiet of the two bedrooms. A sliding glass door allows access to a private patio with a umbrella table, chairs and a gas barbecue.brbrThe second front bedroom is 12 by 15 sq. ft. and has a queen size bed, two side by side closets and a large dresser. brbrThe front room is 13 by 15 sq. ft. This room is furnished with a three person queen size Italian leather sofa bed couch, a 55 inch OLED SMART TV complete with a Spectrum cable box., a four person dining table expandable to six persons and a built in kitchen. brbrHigh speed Internet access available. Boogie boards, 4 beach chairs, beach towels and a cooler are available for a fun day on the beach. There is a full kitchenette with a quartz countertop with a drop in sink, a full size wall mounted microwave unit, a toaster oven, a toaster, a coffee maker, a two burner hot plate, and assorted cooking utensils plus a large breakfast griddle. There is also a full size refrigerator.brbrWashroom/bathroom/shower combination. The split bathroom has a privacy door separating the shower and toilet from the double sink cabinet. There are also two hallway privacy doors separating the bathroom from each bedroom. Washer and dryer available. Air conditioning in only the back bedroom.brbrConvenient street parking. Whenever I have four or more adult guests booked, I make a second full private bathroom available at no additional charge.brbrThe queen size Italian leather sofa bed is of top quality and is very comfortable. It pulls out easily and can be retracted with minimal effort.brbrThe unit is best suited for no more than 5 adults or 4 adults and 2 children. How ever the three queen size beds can sleep 6 adults.brbrPlease e-mail me for any special requests as I try to be as accommodating as possible. Baby playpen available.brbrLocated in the beach town of Kailua which has a great assortment of restaurants and shops. The vacation unit is on Kakahiaka Street which, in my opinion, is one of the nicest residential streets in all of Kailua. Close to both the beach and Kailua Town with minimal traffic.brbrGuests have free use of a large quality LG washer and dryer located conveniently outside the front door.brbrThe City & County of Honolulu now requires stays of 29 days or longer as per local laws and regulations. The C&C also imposes an 17.96% tax on all vacation rentals and hotel rooms on the island. No exceptions.brbrDOGS ARE WELCOME!! Small to medium size. 1-2 dogsbrbrKeywords: Single family home. One level, no stairs or steps inside or outside.brMinimum 29 Day Stay Due to City & Counter Regulations.

Tradewind Bungalow, in Kailua on Oahu

Kailua, Hawaii, United States

Bed

Bath

6

Sleeps

$943.83

This property is offered as a monthly rental. Although full-month occupancy is not required, the monthly rate remains fixed and applies in full, regardless of the number of nights stayed, as prorated rates are not available.brbrRanch Beach Estate 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’ markets. A well-manicured grass driveway welcomes you with a salty breeze and fragrant plumeria, hinting at the luxurious and easy-going lifestyle this Hawaiian home-away-from-home provides.br brThe private gated entrance leads you to a tropical landscaped and fully-fenced yard that grants you complete privacy. The home itself is elevated and provides the perfect perch to enjoy the ocean views, both from within the home and from the spacious wrap-around deck. The deck features multiple seating areas as well as an umbrella table and matching chaise lounges offering a tranquil place for you and your guests to dine and relax outdoors. Just inside the sliding glass doors, you’ll find your newly-constructed Oahu luxury rental home offering you every delight and amenity you could dream of including beautiful ocean views from both the living and dining room.br brRanch Beach Estate features 4 bedrooms and 3.5 baths between the main house and guest house. In the main house, you’ll find 2 bedrooms. The Primary Bedroom is extremely spacious and boasts a king bed, direct access to the private deck, partial ocean views, a ceiling fan and a split A/C unit. Plus, a workspace with a desk for those who need to keep in touch with work while on vacation. There is also an ensuite full bath attached with a stand-alone tub, shower, and large walk- in closet. In the main house Guest Bedroom, you’ll find a queen bed, a workspace with a desk, and floor-to-ceiling windows with views of the expansive private deck. There is a shared full bath directly across the hall.brbrThe Guest House is a completely separate and private space that can be accessed directly through the yard or through its separate driveway entrance. The bedrooms can both be found on the first level. To the right, the spacious Primary Bedroom has a beautiful garden view, split air conditioning, and its own private entrance to the outdoor deck. A hallway bathroom is around the corner and offers double sinks, a shower with tub, and a door leading to a private outdoor shower. The secondary guest bedroom features an ensuite half bath, split air conditioning, and its own access to the outdoor lanai. brbrThe open-concept floor plan in both the main and guest houses allows one to seamlessly traverse and entertain from the living, dining and kitchen areas. The wraparound deck on the main house boasts shaded seating around the perimeter, a high-top outdoor dining set with umbrella, and chaise lounges to soak up the beautiful ocean views and island sun. The guest house features a private lanai off the living room creating an intimate space to relax or retreat to while the large deck off of the kitchen makes for a perfect gathering place to lounge or dine alfresco.br brQuite possibly the most exciting aspect about Ranch Beach Estate is its ocean views and its location just steps away from Kailua Beach. Across the private lane, you’ll be delighted to find access to the most desirable area of the beach where daily walks, swims, surfs or paddles are simply too convenient to pass up. The ocean is truly your playground!br brKnown for its gorgeous stretch of white sand beaches and kid-friendly waters, Kailua Beach is 2.5 miles of crescent white sand beaches, turquoise waters and picturesque islands that are scattered along the horizon. Kailua Town is a quaint, yet lively beach town on Oahu's east shore. While the town itself is small, it’s home to numerous thriving cafes, bustling boutiques and highly-rated restaurants. It’s no wonder that this location is perfect for families who enjoy outdoor ocean sports, bike riding, exploring and healthy living.brbrPlease note, a Utility Fee of $750 per month will be charged for all stays of 21 days or more.br brThe property will be made exclusively available to the renter for a full period of 30-days and no one else may occupy the property during that period. Rates based on a 30 day rental period. Please inquire.brbrTA-129-806-1824-01brTMK 430130190000

Private Luxury Home, Steps from the Beach w/ AC: Ranch Beach House Estate

Kailua, Hawaii, United States

Bed

Bath

Sleeps

$777.76

THIS PROPERTY IS A LEGAL SHORT TERM RENTALbrCONTACT HOST/RESERVATIONS & DETAILSbrbrThis airy, spacious four bedroom Kailua beachside vacation rental home with AC provides the essence of tropical Hawaiian living. Remodeled kitchen and bath(s) finish off this stunning home. Whether you prefer lounging in the sun alongside the very private and enclosed swimming pool, relaxing in the heated spa or watching the sunrise from beautiful Kailua Beach, all are there for your personal enjoyment. This home is located just steps from Kailua Beach on a quiet street. Wonderful restaurants, shops, and water sport rentals are just a few blocks away in Kailua town. br br4 Bedrooms - Two Cal Kings, Queen and two Twin beds. 3 Bathrooms - Master bath includes tub and shower. Spacious living and dining area. AC in living/dining room and 3 bedrooms. Ceiling fans in every room. Driveway and street parking available. Fully fenced and enclosed yard and pool/spa area with outdoor shower for rinsing off sand. Boogie Boards & beach chairs available for use. Beachside with private beach access. 3 minute walk to beach. 30 day rental period.

Beachside Kailua AC - DATES AVAIL incl Christmas! Min Stay 7 Nights-CONTACT HOST

Kailua, Hawaii, United States

Bed

Bath

Sleeps

$253.72

Say aloha to this beautiful vacation rental in east Oahu! This Kailua home features 3 bedrooms, 2 bathrooms, a well-equipped kitchen, and a peaceful yard, making it the perfect home base to explore the island. Whether you're hoping to hike, swim, or learn to hula dance, you won't have to travel far to enjoy your favorite activities! The property is centrally located 12 miles from Honolulu, with so much to discover nearby. Ideal for families or friends, this home has something for everyone!brbr-- THE PROPERTY --brbrTA-045-647-8720-01 | GE-045-647-8720-01 | 430650420000 | Family Friendly | Central LocationbrbrBedroom 1: King Bed | Bedroom 2: Queen Bed | Bedroom 3: King Bed | Living Room: Twin Daybed | Additional Sleeping: Pack ‘n PlaybrbrOUTDOOR LIVING: Dining table, gas grill (propane provided), landscaped yard, beach chairs, boogie boards, cooler, beach towelsbrINDOOR LIVING: Open floor plan, 2 Smart TVs, ceiling fans, dining table, coastal decor, eat-in kitchenbrKITCHEN: Dishwasher, electric stove top, microwave, drip coffee maker, blender, toaster, Crockpot, cooking basicsbrGENERAL: Free WiFi, washer & dryer, mini-split A/C units, keyless entry, linens, towels, complimentary toiletries, hair dryer, high chair, paper products & trash bags (starter supply)brFAQ: Homeowner on-site (main house), 3 external security cameras (facing out), quiet hours (9:00 PM - 8:00 AM)brSUITABILITY: Step-free access, single-story homebrPARKING: Shared driveway (2 vehicles)brbr-- THE LOCATION --brbrOUTDOOR FUN: Kailua Beach (1.0 miles), Kawainui Marsh Wildlife Sanctuary (2.5 miles), Lanikai Beach (2.9 miles), Lanikai Pillbox Hike (3.0 miles), Maunawili Falls (4.1 miles), Waimanalo Bay (6.8 miles)brNEARBY SITES: Ulupō Heiau State Historic Site (2.1 miles), The Byodo-In Temple (7.8 miles), Nu‘uanu Pali Lookout (7.9 miles), Halona Blowhole Lookout (13.1 miles)brHONOLULU HOT SPOTS: Aloha Tower (12.3 miles), Iolani Palace (12.4 miles), Honolulu Zoo (16.2 miles), Lyon Arboretum (16.7 miles), Diamond Head State Monument (18.0 miles)brAIRPORT: Daniel K. Inouye International Airport (16.0 miles)brbr-- REST EASY WITH US --brbrEvolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.brbr-- POLICIES --brbr- No smokingbr- No pets allowedbr- No events, parties, or large gatheringsbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbr- NOTE: The homeowner lives on-site, in a completely separate unit, and may be present during your staybr- NOTE: Please observe quiet hours from 9:00 PM to 8:00 AMbr- NOTE: The owner provides a starter set of paper supplies, toilet paper, paper towels, soap, and trash bagsbr- NOTE: Your safety matters. This property features 3 exterior security cameras. Cameras 1 and 2 are located on the exterior wall facing the driveway, and there is a Ring doorbell device with an exterior security camera facing the main entry. All cameras are outward facing and do not look into any interior spaces. The cameras record video and sound when activated by motion

Sunny Kailua Home w/ Covered Lanai 1 Mi to Beach!

Kailua, Hawaii, United States

Bed

Bath

Sleeps

$919.0

Just a 60 second walk from world-famous Lanikai Beach, this unique 2-bedroom setup offers two private 1-bedroom studios. Each studio features its own kitchenette, dining area, sofa, private balcony, and full bathroom. Enjoy cool A/C, fast Wi-Fi, and thoughtful touches throughout. Relax, explore, and soak in the best of Lanikai. - Two Separate Private Studios with a small private hallway attaching the two Studios. - 2 Bedrooms | 2 Bathrooms - King sized beds in each studio - Air Conditioning in Every Room - Blazing-Fast Wi-Fi - Parking for 2 cars - Kitchenette in each studio - Dining table in each studio - Sofa in each studio with TV - Two separate outdoor patios A private entrance leads to a staircase where, at the top, you'll find a small hallway with two separate lockable doors—each opening to its own studio. Whole Foods, Target, Shopping, and Dining are just minutes away! There is reserved parking for 2 cars. All bedrooms and bathrooms are stocked with towels, linens, blow dryers, shampoo, conditioner, soap, and toilet paper. Each kitchenette has a mini fridge, microwave, sink, countertop space, utensils, plates, cups, cookware, coffee maker, and toaster. There is a property manager who lives on property in a private section with her own entrance. The property manager is meant to assist with emergencies and to help with any questions. You will not know that the property manager exists because she does not share any common areas with you and she has her own private entrance separate from the house entrance. If you need anything additional, please don't hesitate to ask! TMK: 4-3-008:030 License Number: 1990/NUC-1752 General Excise: GE-015-067-6992-01 Transient Accommodations: TA-015-067-6992-01

60 second walk to Lanikai Beach. 2 Bedrooms w/ AC

Kailua, Hawaii, United States

Bed

Bath

Sleeps

$491.7

Just steps from the white sand shoreline of Kailua Beach, Ranch Beach House offers a private, garden-surrounded setting designed for relaxed island living and effortless indoor outdoor flow.brbrSet along one of Kailua’s most desirable residential loops, this single-level home sits behind a gated entrance and fully fenced tropical landscaping. The result is a calm, secluded retreat that feels tucked away while remaining close to cafés, boutiques, and farmers’ markets. Inside, vaulted ceilings, skylights, and an open layout bring in natural light and gentle breezes throughout the day.brbrWhat You’ll Love About Ranch Beach Housebr• Just steps to Kailua Beach across a quiet private lanebr• Fully fenced yard with spacious deck and multiple lanaisbr• Vaulted ceilings with skylights and bright interiorsbr• Private outdoor shower surrounded by lush greenerybr• Ideal monthly rental for couples or small familiesbrbrLiving & DiningbrThe open-concept living area connects seamlessly to both the garden lanai and the main deck, creating an easy flow between indoor and outdoor spaces. Comfortable seating, split air conditioning, and a large Smart TV make this a welcoming place to unwind after beach days. The dining area sits just off the kitchen and opens directly to the outdoor deck for relaxed meals at home.brbrChef-Ready KitchenbrThe kitchen is well equipped for everyday cooking during longer stays, featuring modern appliances, generous counter space, and essential cookware. Whether preparing simple breakfasts or casual dinners, the layout supports easy, functional use.brbrOutdoor OasisbrOutdoor living is central to the Ranch Beach House experience. The main deck features an umbrella dining table and chaise lounges, while a secondary lanai off the living room provides a quieter retreat. A private outdoor shower offers a refreshing rinse after time at the beach, tucked into tropical landscaping for privacy.brbrSleeping Quartersbr• Primary Bedroom: Queen bed, garden view, split A/C, private access to the deck and yardbr• Guest Bedroom: Queen bed, split A/C, ensuite half bathroombrbrA hallway bathroom includes a double vanity, full bathtub, and shower.brbrExtrasbr• High-speed Wi-Fibr• Smart TV with cablebr• Washer and dryerbr• Beach towelsbr• Private entrance with keypad accessbr• One dedicated parking spacebr• Outdoor lighting and in-room safebrbrNearbybrWalk:br• Kailua Beachbr• Local cafés and coffee shopsbr• Boutiques and neighborhood marketsbr• Farmers’ marketsbrbrShort Drive:br• Kailua Town dining and shopping districtbr• Golf coursesbr• Hiking trails and coastal lookoutsbr• Wellness studios and spasbrbrGood to Knowbr• This property is offered as a monthly rental. The monthly rate applies in full regardless of length of stay.br• The home is reserved exclusively for the renter for a full 30-day period.br• Utility fee of $500 per month applies to stays of 21 days or more.br• No pets permitted.br• Smoking is not allowed.br• Free on-site parking for one vehicle.br• Tax ID: TA-129-806-1824-01br• TMK: 430130190000brbrReserve your dates at Ranch Beach House and settle into the rhythm of Kailua life. From morning walks along the shoreline to quiet evenings on the lanai, this private beachside retreat offers a comfortable, well-located home base for an extended island stay.

Private Luxury Home, Steps from the Beach w/ AC, Ranch Beach House

Kailua, Hawaii, United States

Bed

Bath

Sleeps

$480.12

**Please note--beginning Sept. 25, 2025 only 90 Day rentals and longer will be accepted.brbrWelcome to paradise! Discover this adorable 4-bedroom gem in Kailua only 4 houses from magnificent Kailua beach. We are on a private lane with path to beach.brbrThis charming house has been completely renovated with new kitchen and bathrooms, hardwood floors throughout main house and all brand new furniture and bedding. Private yard with outside seating and dining. There are 3 bedrooms and one bath in the main house and an attached bedroom with bath and loft area that are accessed from a separate entrance. Fully stocked kitchen. washer/dryer, AC, Smart TV and WiFi. Double Kayak, 3 bikes, snorkels, boogie boards, beach chairs.brPlease Note--Beginning in 2026, there will be an additional bathroom creating a true primary suite--so 3 total.brbrThe house is a 2 min WALK to Kailua beach down a private lane (ignore the VRBO map and stances). Kailua Beach is often rated one of the best beaches in the world. The house is a 15 min. walk or 5 min. drive from Kailua Town. Kailua is a charming town with many delicious restaurants and shopping for everyone including:brIsland Snow, Lanikai Juice, Kalapawai Market, Kailua Beach Adventures, Mahina and so much more! Additionally, there is a Target and Whole Foods in town for your convenience.brbrThe house is close to many great hikes including the Lanikai Pillbox hike--a great way to watch the sunrise! Or you can just walk to the end of our lane and watch the beautiful sunrise over the ocean, then walk down the beach to Kalapawai Market for their amazing Kona coffee--our favorite way to start the day. Come experience the phenomenal comfort and convenience this property has to offer. We look forward to welcoming you to our place.brbrbrThe property will be exclusively available to the renter for a total of 90 days, and no one else may occupy it during that period, even if you leave early. Rates are based on a 90-day rental period. Ask about possible longer-term discounts. Hawaii GET TAT and OTAT are charged. TA-100-709-7344-01 TMK143015028000brbrbrIf the rental period is confusing, please send a message with questions before submitting a booking request. Additionally, we offer a multi-month discount. All bookings are subject to approval.

Steps to beach! Beachside 4-bedroom house in Kailua with AC & WiFi

Kailua, Hawaii, United States

Bed

Bath

6

Sleeps

$1686.55

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! You are invited to rest and relax in “Ka Hale Lai” , Kailua’s House of Serenity, 5 minutes to the beach, and a short drive to the heart of Kailua town. This is a Legal, licensed vacation rentalNUC#90/BB0034. You will feel like you are visiting old Hawaii in this classic home. Enjoy modern conveniences like AC in every room and new kitchen and bathrooms. brWe invite you to experience the beauty of Kailua!!brWe are located in a quiet Kailua neighborhood called Kaimalino—a short walk away from Turtle Beach. We are walking distance from a grocery store and restaurants but away from the busier Kailua town. We are close to the H-3 on ramp which can get you to the airport in 25 minutes. Sand bar and fishing charters available for additional fee if available.brbrThe State of Hawaii is welcoming visitors with negative COVID tests and allowing legal vacation rentals starting this week! We are so excited to welcome you back to Ka Hale Lai!!brSorry no discounts or extended term rates!

Perfect Kailua Vacation at Ka Hale Lai-House of Serenity-pool and spa.

Kailua, Hawaii, United States

Bed

3

Bath

8

Sleeps

Select Dates for Price

This cozy, beachy bungalow is right across from the manicured and security patrolled Kalama beach Park entry onto the world-famous Kailua Beach. Listen to the sounds of the waves at night as you relax after your long work and/or fun-filled beach day. The studio is bright and clean with air conditioning, a full kitchenette, futon or twin bed, clean bathroom, with separate large shower and full bathtub. Garbage disposal in enlarged bath sink, individual lanai, shared outdoor laundry/drier. Carport hosts shared and separate living and parking spaces on the property's private gated entrance. Home has two small breed dogs and a cat now, all very friendly, so pets based on my discretion with additional $500 non-refundable pet-deposit upon move in date. Non-smoking on the property grounds. No tolerance regarding illicit/illegally obtained Rx or non- drugs /paraphernalia/discussion/guests invited or within visibility of the property.brbrThis is our family home, and we are fortunate, with more space than we need. brbrWe are in the perfect location! Why 5–10-minute commute to either MCBH gate in Kaneohe, or bike to PT! Heading the other direction, Kailua attracts millions of people a year and parking is hard to come by! You don’t need to drive to the beach or stores if you don’t want too! We are one street over from the pathway to Kailua Beach! We are within a mile to bike, windsurfing and kayaking rentals. We are also a mile to Whole Foods, cute shopping boutiques and restaurants. We are about a 25-minute drive to Waikiki, 50 minutes to the North Shore but just a few minutes' walk to one of the best beaches in the world without the hassle of parking. The space has a wall unit air conditioner and a ceiling fan. The kitchen has an air fryer, coffee maker, microwave, toaster oven, refrigerator and pots and pans. The studio is attached to our home, and we are a family, but we do our very best to keep quiet. But please keep this in mind if you are looking for super quiet. Free washer and dryer for guests.

Kalama Beach Studio

Kailua, Hawaii, United States

Bed

Bath

Sleeps

$772.69