Vacation Rentals By Owner In Kailua, HI

$111.5

Budget Friendly Camping Experience

Kailua, Hawaii, United States

Embark on a camping experience in Hawaii with our minivan camper perfect for individuals or couples.brbr**Located in Kailua!! It's a 25 minute Uber/Lyft from the airport.brbrCAMPING GEAR INCLUDED:br► 8 Memory Foam Mattress with CLEAN FRESH sheets br► Solar Powered Rechargeable Battery with 120 volts AC and plenty of USB ports br► Extra USB C and Lightning Cables br► Mobile Wifi Internet Hotspot br► Sink with Running Water br► Propane Gas Grill with 2 Burners br► Metal Pot and Frying Pan br► Coffee Maker and 2 Metal Mugs br► Cooking and Eating Utensils br► Plates, Bowels and Cupsbr► Refrigerator / Freezer Adjustable br► Beach Chairs br► Beach Towels br► Hammock br► Clothes Line br► Portable Flashlights brbrImmerse yourself in the beauty of Hawaii in luxury with our specially customized minivan camper designed for solo travelers or couples looking for an exceptional camping adventure. Our converted van offers all the conveniences of home whether you're parked by the ocean, mountainside or exploring Waikiki. Experience a way to explore Oahu by blending comfort and nature for an unforgettable Hawaiian retreat.brbrStep inside your mobile abode featuring a plush 8 inch memory foam bed ensuring you get a good nights sleep after your day of island exploration. The vans kitchenette comes fully stocked with everything needed to whip up meals, on the go. Including a two burner gas stove, mini fridge/freezer combo, utensils, cookware and running water.brKeep in touch. Keep your devices charged with our solar powered battery system perfect for powering up when you're off the grid.brbrWe've taken care of every thing to ensure your stay is extraordinary. Enjoy adventure essentials like a hammock beach towels, beach chairs and more—ideal for enriching your island getaway. For your convenience we offer linens, storage bags, a vacuum cleaner and sanitizing wipes to maintain a neat space. Safety comes first with a fire extinguisher, first aid kit, car emergency kit and a standalone battery jumper provided.brbrEnjoy privacy at its finest with our ventilating pop out windows and exclusive fit window shades that can be reversed as needed. You can admire the Hawaiian landscapes while staying comfortable.brbrStay connected with Wi Fi for entertainment or work purposes or to plan your next escapade.brbrDiscover Oahu like a local. We give you insider tips on recommended parking spots and camping sites on the island so you can explore Oahu with insights. Whether you're looking for beaches or picturesque mountain views our van offers you an authentic local experience.brbrEmbark on a one of a kind adventure on the island of Oahu, with our minivan camper.brYour well being, security and enjoyment are our concerns ensuring that your stay is exceptional.brbrThank you for selecting our minivan camper for your escapade!

1

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2

Sleeps

$166.91

/ Nightly

Apartment

Suite By the Sea - a bright and sparkling Apartment

Kailua, Hawaii, United States

Welcome to our new private studio apartment, where comfort and convenience await you. This hidden gem boasts a well-equipped kitchenette, perfect for preparing your favorite meals. Nestled just a short stroll away from the breathtaking Kailua Beach, you'll find yourself in a paradise of your own.brbrAs you step through your private entrance, the tranquil ambiance of the studio embraces you. With modern amenities including air conditioning, your comfort is our top priority.brbrThe apartment is located very close to Kailua Beach and minutes from Lanikai Beach. At roughly 550 sq ft, the studio suite is spacious, modern and clean, with lots of windows offering sunrise and mountain views.brbrThe all new construction features bamboo floors, quartz countertops and a river rock shower floor to massage your feet. The kitchenette has a full size refrigerator, sink, microwave, two burner induction cook top, rice cooker, toaster, dishes and cutlery. There is a Queen size bed and a Full size futon couch. We also offer a gas grill for cooking outside.brbrOur tropical breezes are cool and refreshing, but for those who prefer air conditioning, that's also available.brbrWe provide coffee and tea for your first morning, but you may want to stock up on fresh produce at the local farmers market (offered 3 times per week).brbrTropical outdoor sitting area with BBQ and outdoor shower.brbrHelp yourself to a beach chair and towel and take a short stroll to Kailua Beach. Stop off at the famous Kalapawai Market where they can make you a delicious deli sandwich for a picnic lunch or serve up a latte just the way you like it.brbrOnce you return to your home away from home, rinse off in the hot outdoor shower, hang your wet things out to dry and perhaps take a nice nap before heading out to the charming town of Kailua. You'll find many restaurants to choose from in all price ranges.brbrIf you choose to venture out to explore, Kailua is the perfect get-anywhere location. The island of Oahu is only 40 miles tip-to-tip, so you can explore it all quite easily. Honolulu and Waikiki are just a half-hour away. As your on-site hosts, we will help you discover and enjoy our beautiful island.brbrOwners live on site and we are happy to help you with any questions and to provide you with our local knowledge. We have a friendly dog on-site. She does not have access to your space.brbrWe welcome you to come stay and enjoy all the wonderful delights that Hawaii and Kailua have to offer!brbrHigh speed wireless Internet and basic cable TV are provided. There is a laundry center exclusively for guest use. Detergent is provided as well. Outside on your private lanai there is a gas BBQ and a hot outdoor shower.brbrThis property is a legally established dwelling that is rented for periods of 180 consecutive days or more at any one time regardless of actual occupancy.

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$453.6

/ Nightly

Private Vacation Home

Luxury Coconut Grove, Kailua Vacation Home

Kailua, Hawaii, United States

Bright and airy home with ample large windows to let in the fresh ocean breeze. Brand new built in 2021! Spacious rooms with a beautiful kitchen to prepare your favorite island dishes. Downstairs 3 bedroom 1 bath lockout unit also available. They can be connected as one space with 7 bedrooms and 3 baths. Rent both for larger families or groups traveling together. Nice, quiet neighborhood location with no through traffic. Close to quaint Kailua Town shopping and eateries and walking distance to Kalama Beach Park and Kailua Beach. Only 25 minutes to world class shopping, dining and entertainment in Waikiki, but insulated from the traffic and noise of Waikiki. Come find your island vibe here in Kailua!

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$294.79

/ Nightly

Private Vacation Home

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

Kailua, Hawaii, United States

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.

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Sleeps

$366.9

/ Nightly

Cottage

Beautiful Beachside Bungalow

Kailua, Hawaii, United States

LOCATION LOCATION LOCATION.....brEnter ParadisebrRelax and Enjoy the Gentle Breezes of Kailua…brThe Original Kailua Beach Bungalow is elegantly renovated with a spacious open floor plan. Modern design mingles with Hawaiian tradition - Furnished with comfort and ease - thoughtfully designed with all the modern necessities including high speed fiber optic internet, private laundry, large walk in closet with lots of storage, fully equipped kitchenette with induction cooktops, full size refrigerator, etc. The bungalow is fully air-conditioned should the need arise. Large outdoor private enclosed patio with hot and cold running shower. Elegance, Comfort and Island Style at it’s best.brThe Original Kailua Beach Bungalow offers the utmost relaxation and tranquility - feel the white powdery sand between your toes ~ bask in the warm Hawaiian Island sun & dive into the crystal clear aqua waters. brIt’s been said that this Bungalow is “One of the best kept secrets in the world” and it is…..brOur Original Kailua Beach Bungalow is spacious, newly renovated and beautifully furnished. We go to every length to covid clean and keep you safe and healthy.brThe Bungalow provides everything you will need for an unforgettable vacation..brAmenities Include…..Wireless Fiberoptic Internet, Air Conditioning, Open Beam Ceilings, walls of windows that offer an indoor / outdoor living experience, Washer & Dryer, Iron and Ironing Board, blow dryer, beach towels and shower towels, boogie boards, beach chairs, beach umbrella, chaise lounges, equipped kitchen, 300 sq. ft. private enclosed patio, Outdoor Dining, Windows from floor to ceiling, Just step’s to Kailua Beach. brEnjoy your morning coffee or tea on Kailua beach watching the morning sunrise’s - - - enjoy long walks on the powdery soft sand and swim in it’s the crystal aqua blue Hawaii ocean - - - enjoy fabulous snorkeling - - - kayaking to the island’s just off shore - Walk or drive to spectacular shops and restaurants in Kailua Town Kayaking, Hiking, Bike Rentals, Stand Up Paddle Boards Available in walking distance, etc. Beautiful Beachside Bungalow - Steps to Famous Kailua beach - Home is located on beachside and within walking distance to town as well just steps to the beach.brOpen Airy Bright Beautiful One Bedroom and One Bath with it's own entrance, private spacious patio and privacy. brAlso walking to Lanikai Beach - Biking - boating - kayaking - etc. brCome experience the world renowned beautiful beaches of Kailua - just steps from your door. brPlease inquire about availability, as it may differ from what is shown on calendar.brIn compliance with the revised ordinances of the City and County of Honolulu, the minimum advertised rental period for this property is 30 consecutive days per the Kokua Stipulation as agreed by the City and County of Honolulu. This property is a legally established dwelling. brPlease inquire about availability, Inquire and let us know your requested dates so we can accommodate you !!!brIn consideration of COVID-19 we are cleaning and sanitizing thoroughly between guests, including sanitizing all touched surfaces, and laundering all bedding, linens and couch covers.brRecently remodeled and refurnished from the ground up. Everything is fresh, new, clean, and modern. brPer Hawaii law we need to add on the required GET & TAT Tax Hawaii RequiresbrCheck in is 3:00 PM but earlier check in might be arranged.brCheck out is10:00 AMbrFeel free to reach out even if the calendar shows not available as well as with any questions regarding available dates and booking availability.brThis property has been registered as a Transient Accommodation with the State of HawaiibrState of Hawaii Transient Registration Licensebr # TA-064-669-6960-02 / GE-064-669-6960-02brHawaiianislandbeachbungalows.combr Also Inquire about special monthly discounts brContact us for great reduced rates depending upon season and availability! Don't see your dates Email or text to check! Not all my available dates are listed on this calendar br808-600-9731 vickisummerland@me.combr

1

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1

Bath

2

Sleeps

$3168.79

/ Nightly

Private Vacation Home

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

Kailua, Hawaii, United States

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.

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$775.37

/ Nightly

Private Vacation Home

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

Kailua, Hawaii, United States

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.

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$459.52

/ Nightly

Private Vacation Home

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

Kailua, Hawaii, United States

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.

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$1187.12

/ Nightly

Private Vacation Home

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

Kailua, Hawaii, United States

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

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$383.35

/ Nightly

Apartment

Kailua Condo / Townhouse on Oahu 30 day period 7 day min

Kailua, Hawaii, United States

”Aloha and Welcome Home message me on availability as it can only be rented once in a 30 day period. Ordinance 19-18 does not require a renter to physically occupy a rental property for any minimum length of time. Remodeled 2x bedroom 2x bathroom condo / townhouse. It is idea for a single family. There are 2x parking spots available. Close to Castles beach, Safeway Shopping Center and K bay Main Gate. There is a BBQ on the Lani right outside the kitchen. Located in Aikahi Gardens with a community Pool and Spa. We also have 2x e bikes available. I will happily offer discounts for extended stays. @stayinkailua

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$240.1

/ Nightly

Private Vacation Home

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

Kailua, Hawaii, United States

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.

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$666.0

/ Nightly

Private Vacation Home

Kahela - Paradise for Rent

Kailua, Hawaii, United States

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

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$350.59

/ Nightly

Cottage

BEACHFRONT! Barefoot living on the best spot on Lanikai Beach!

Kailua, Hawaii, United States

BEACH FRONT property. Step from the property onto World famous Lanikai Beach....soft white sand and clear green water awaits you each morning. brbrFOR QUESTIONS AND TO CONFIRM AVAILABILITY AND LENGTH OF STAY please email us at PaddlersDreamLanikai@gmail.com. brbrHow to pass your day Walking barefoot in the soft sand, snorkeling in our clear protected waters observing the colorful reef fish and turtles, paddling a kayak out to the Mokulua Islands less than a mile off shore, hiking up to the pill boxes for unbelievable panoramic views.brbrEnjoy an evening beverage as the sun sets behind you . . . Beachfront table for enjoying the ocean views . . . Relax in the hammock under the coconut palms feet from the beach.brbrPrivate back yard gazebo if it is too breezy up on the oceanbrbrQueen bed for 2 adults. Double bed for up to 2 children/plus additional twin bed (in separate room). [No children under 5 years old.]brFull kitchen with pantry. Fabulous and private outdoor shower. Washer/Dryer. High speed Internet and 43 Smart TV w/cable, Netflix and more.brbrAir conditioning for the occasional muggy summer afternoonbrbrGATED, COVERED AND SECURE OFF STREET PARKING!!! Never fight to park on the streets of Lanikai and never worry about your car being broken into! Automatic gate with remote.brbrKid friendly safe swimming -- protected from surf by Lanikai reef.brbrThis is a street side cottage on an beachfront lot. Owners live in the other cottage.brbrNon-Smokers only please.brbr*** Ordinance 22-7, Section 10(c)(2)(B), effective October 23, 2022, requires that ads state: This property may not be rented for less than 90 consecutive days. Rental prices will not be reduced or adjusted based on the number of days the rental is actually used or occupied. brNOTE: a federal judge has enjoined enforcement of Ordinance 22-7 against properties previously rented for 30 to 89 day rental periods.brbrPlease feel free to contact us at PaddlersDreamLanikai@gmail.com.brbr[This listing is exempt from the advertising requirements of ROH 21-5(c). ROH 21-5(c)(3)(C)]brbrThis Property has a General Excise Tax License and is registered as a Transient Accommodation with the State of Hawaii and Oahu. brHawaii Tax ID Number: GE-154-795-6224-01brTransient Accommodations Tax No: TA-154-795-6224-01brTMK: 430050520000

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1

Bath

4

Sleeps

$135.63

/ Nightly

Apartment

Stunning Views: 5 min to beach and you will be amazed by the mountain views !

Kailua, Hawaii, United States

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 views of the coast line. From the studio you may feel like you are in a birds nest , since there are birds singing ,and the Tradewinds bring the breeze and fragrances of Hawaii. The studio is an 8-10 minute walk from 2 mile long Kailua Beach, and just a few minutes further to world famous Lanikai beach, rated one of the 10 best beaches. The studio is private, shares no walls with the owners, and has a separate entrance and outside private yard area separate from the owner's use area. In the studio, there is a queen bed and also a futon that folds open for extra guest. One wall is windows with the stunning Mountain View. There is a galley kitchen, a large walk in closet and bathroom with shower, tub and double sinks. There is access to deck and which has chairs and table, and hammocks are available. Bbq and laundry facilities are in and near the garage which is downstairs from the studio.brKailua beach is renowned for kite surfing, kayaking and SUP rentals, snorkeling, surfing and hiking. Ideal for remote working or a complete get away ! The neighborhood is safe and mainly occupied by residents who are professionals as well as having a definite beach and outdoor adventure vibe with all that is accessible in scenic Hawaii. There are miles of beaches within walking distance, as well as hikes with panoramic views within minutes of the studio. Kailua town with all its conveniences and restaurants is a 5 minute drive, and also ideal for walking or bike riding. The cultural, historic, and entertainment is available in Honolulu, just a 35 minute drive from Kailua. Come visit the big surf at the north shore within 11/2 hours drive, and the historic Pearl Harbor museum which is a 45 minute drive.

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$1208.49

/ Nightly

Private Vacation Home

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

Kailua, Hawaii, United States

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.

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Sleeps

$591.26

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Cottage

Kailua Palms Guest House with Pool and Views! Parking and wi-fi included

Kailua, Hawaii, United States

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 located in sleepy Kailua Town near Kailua Beach. brbrThe two bedrooms are spacious and comfortable. You will like the relaxed and casual indoor/outdoor living with lanais, patios and gardens. Free parking and wi-fi are included. brbrThere is a beautiful tiled swimming pool (with 50 foot lap section) on the property, barbecue grill and washer and dryer.brbrLocated on the canal, the Kailua Palms Estate Guesthouse is minutes from world famous Kailua Beach. Just a short 10 minute walk.brbrA beautiful balinese style cottage ...absolutely perfect for you!brCome and enjoy the beauty of Kailua town and kailua beach...all minutes away.brAikahi park shopping center directly across the street for immediate access to shop at Safeway and a little strip mall for gas, restaurants and great coffee.brbrPlease note In order to remain compliant with city and county zoning regulations this property is only rented for periods of 30 days or more to one party. This property is a legally established dwelling that is rented for periods of 30 consecutive days or more at any one time. Feel free to contact us with any questions.brbrSee you soon!brbrbrbrKeywords: private balinese style cottage, pool, brgarden, yard

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$1021.49

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Private Vacation Home

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

Kailua, Hawaii, United States

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.

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$186.4

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Private Vacation Home

Tradewind Bungalow, in Kailua on Oahu

Kailua, Hawaii, United States

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.

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$342.09

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Apartment

Available and legal for stays less than 30 days.

Kailua, Hawaii, United States

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 unique neighborhood stay in Kailua Hawaii that is just down the street from Kailua Beach.brbrThe Hawaii Sheffield House Ginger Studio has a 'Secret Garden. The night lighting is enchanting. We are Located at 131 Kuulei Road in Kailua . It has a private entrance and is on the ground floor with windows opening to a tropical bank of Areca palms. The Ginger Studio has a private entrance and a private bath that has a huge walk-in shower . A breakfast bar with toaster oven and coffeemaker and under counter refrigerator is provided in the room. Check the calendar for last minute vacations or specials.brbrJust outside the door in the garden, is a bubbling fountain in a Chinese steamer pot. There is a comfortable queen size bed. The beach is calling and there are activities galore, a perfect Hawaii vacation. Take a beach chair and a boogie board located by the entry door and walk to Kailua Beach and enjoy some beach time.brbrThere is an Olympic size community swimming pool and tennis courts 13 houses up the street toward Kailua Town. In the other direction is our beach access to Kailua Bay . Hike the Lanikai pillboxes, Visit our wetland, Kawainui marsh. Kailua Beach by Sheffield House is a perfect boogie board spot. Watch the kite surfers or join in. Plan an early morning walk to watch the sunrise.brbrThe Ginger Studio and the Garden Suite 30018 can be combined to make a two bedroom two bath unit and sleep a party of five.brbrThe Ginger Studio has a queen-sized bed with Hawaiian applique quilts and a newly remodeled private bath with a Breccia marble counter top. It has a large shower -big enough for two (no tub). It is equipped with a breakfast bar or kitchenette (No kitchen sink) with a microwave, toaster oven, coffee maker, and under counter refrigerator and a table for two.brbrWhile it is air conditioned, ceiling fans are usually all that is needed. Evenings on the beach you will need a light sweater or jacket all year round. The Ginger Studio has an iron, ironing board, hair dryer, cable TV and wifi. There is an indoor rattan table for two as well as an outdoor table for two/three. Towels, beach towels, and paper towels are provided. At this time we are not accepting reservations which include children under the age of three in this room. . brbrWe only accept reservations with small children when this unit is rented together with VRBO 30018. It is possible to sleep a party of 5 with adjoining VRBO 30018brbrYes, we are in the tropics so you may see geckos, anoles, chameleons and flying insects. Yes, we do use pesticides.brbrNote that there are two coin operated laundromats within 1/3 of a mile away.brbrHawaii Sheffield House is a non smoking property. The Ginger Studio is a self contained vacation rental with everything there that you might need. There is one free parking space in the driveway of Hawaii Sheffield House just steps from the entrance the Ginger Studio.br(Note: You do not have to circle the block or parking garage looking for parking.)brbrSadly, at this time our street can be busier than normal. It is from time to time being used as a detour for the construction at the roundabout at the entry of Lanikai. Hopefully, by the time you read this the detour will be removed.brbrContact us regarding specials brearly December and early MaybrbrLocation:brHawaii Sheffield HousebrKailua Oahu Hawaii 96734brbrState of Hawaii License Number -HI TA137-360-9984-01 brCity and County of Honolulu -License No. 90/BB-0077brbrAkamai or smart travelers brThe best travel rates are the first three weeks of May. Last three weeks of September, and First three weeks of December.brAlways inquire about last minute openings! brbrYes, check the calendar . We will take one or two night stays if it fits between other bookings or if it is done within a month or so of travel.brHawaii Sheffield House has been in business for over 35 years.brbrWalk to Kailua Beach, Walk to Kailua town, Minutes to beach, Relaxing near beach, 5 minutes to beach, sandy Kailua beach, Walk to Kailua Starbucks, Walk to Kailua Whole Foods,

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$328.38

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Apartment

NUC 90/BB-0069, GE-014-134-8864-01, TA-014-134-8864-01

Kailua, Hawaii, United States

Start your day with a stroll on one of the most beautiful beaches in the world. Enjoy the sunrise in Kailua where your Hawaiian holiday truly begins. Kailua Beach is a perfect place to go to 'get-away-from-it-all.' Swim, boogie board, surf, kayak, sail, or windsurf in the warm ocean waters. brbrVisit beautiful Kailua at an affordable price. Our studio is spacious, clean, and provides many amenities. This Hawaiian theme studio is a permitted short term rental unit located a short block from world famous Kailua Bay. Less than two miles to charming Kailua Town with boutique shops, cafes, restaurants, bars, breweries. Whole Foods, Japan Express and much more.brbrOur accommodation has all the modern comfort features such as Split System A/C, 42” TV, Washer/Dryer, Apartment Size Refrigerator, Coffee Maker, Toaster, and Microwave. Super Comfortable King Size Bed with memory foam topper. Extremely Clean (Our crew launders the pillows between each rental). Beach chairs, towels, and boogie boards are provided. The unit has a private yard with patio table, umbrella, and a gas grill. We work hard to think of all the details to make your stay wonderful and comfortable. Hawaii has been our home for more than 50 years and we have lived in Kailua for most of that time. Our wish is that you have a wonderful vacation in Beautiful Kailua!brbrKeywords: Studio

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