Vacation Home Rentals By Owner In Kailua, HI

$892.01

Beachside Kailua Beach House by Gather w/ Pool & Gourmet Kitchen

Kailua, Hawaii, United States

Just a short stroll from the turquoise waters and powder-soft sands of Kailua Beach, Kailua Beach House is a light-filled 4-bedroom, 2.5-bath island retreat designed for laid-back luxury. This single-level residence blends open-concept living with a private outdoor sanctuary, offering 3,700+ square feet of comfort for families, couples, or extended stays.brbrWhat You’ll Love About Kailua Beach Housebr• Sparkling private pool and spa framed by lush palms and tropical bloomsbr• Seamless indoor-outdoor living through sliding glass doors and vaulted ceilingsbr• Two spacious king suites, each with its own ensuite bathbr• Covered lanai with plush seating and al fresco dining areabr• Quiet cul-de-sac setting, just minutes from the beach and Kailua’s charming cafésbrbrLiving & DiningbrInside, sunlight pours through expansive windows, filling the open-concept living room with a breezy, relaxed energy. Comfortable lounge seating faces the pool and garden views, while the dining area easily accommodates eight. A second sitting nook offers a cozy corner for reading or conversation. With high ceilings, natural stone floors, and easy access to the lanai, every gathering feels effortless and inviting.brbrChef-Ready KitchenbrThe modern kitchen combines warmth and function with bar seating, granite counters, and stainless-steel appliances. Ample prep space and a thoughtful layout make cooking a joy—whether you’re preparing family-style breakfasts or unwinding with a late-night snack after the beach.brbrOutdoor OasisbrStep outside to your private Hawaiian haven. The curved-edge pool glimmers under the sun, while the attached spa promises quiet evening soaks beneath swaying palms. The covered lanai features cushioned seating and a dining table for eight, ideal for meals fresh from the grill. A raised deck with loungers invites you to soak up the rays or sip morning coffee surrounded by tropical greenery.brbrSleeping Quartersbr• Primary Bedroom – King bed, ensuite bath, garden view, A/C, ceiling fanbr• Guest Suite 2 – King bed, ensuite bath, garden view, A/C, ceiling fanbr• Guest Bedroom 3 – Queen bed, A/C, ceiling fan, shared bathbr• Guest Bedroom 4 – Queen bed, A/C, ceiling fan, shared bathbr• Powder Room – Half bathbrbrEach bedroom is calm and airy, with large windows framing garden views and soft natural light. Neutral tones, fresh linens, and quiet A/C ensure restful sleep after sun-soaked days.brbrExtrasbrThis home offers thoughtful touches throughout—split A/C, high-speed Wi-Fi, washer and dryer, and a two-car garage. The spacious layout and modern amenities make it an ideal base for both extended vacations and remote work stays.brbrNearbybrWalk to Kailua Beach for morning swims and sunset strolls, or explore the local favorites of Kailua Town just minutes away. Boutique shops, organic markets, and beachside cafés offer everything from fresh poke to island-made gelato. A short drive takes you to Lanikai Beach, Pillbox Trail, and scenic golf courses.brbrGood to Knowbr• This property is offered as a monthly rentalbr• The monthly rate applies in full regardless of the number of nights stayedbr• Minimum 30-day booking period requiredbr• TAT ID: TA-031-662-8992-01br• TMK: 1430830020000brbrReserve your time at Kailua Beach House today and experience relaxed island living in one of Oahu’s most beloved beach communities.

4

Bed

2

Bath

8

Sleeps

Select Dates for Price

Private Vacation Home

Lanikai living . 5 minute walk from Lanikai Beach. Pool, tennis court & hot tub.

Kailua, Hawaii, United States

This 3 bedroom 2 1/2 bath townhouse is located in Lanikai. It is fully furnished and ready for move in. Gated Community with tennis courts , pool , hot tub and BBQ area. Views of the Koolau's and famous pillbox hike. Brazilian Teak flooring throughout, Wrap Around Lanai's with views. Come make exclusive Lanikai your home.brLocated in Lanikai. Voted number one beach in the world by Condé Nast . Very protected and perfect for children . Swim , snorkel or paddle . White sand beach .

3

Bed

2

Bath

6

Sleeps

$545.75

/ Nightly

Private Vacation Home

Hale Alapi'i Lanikai Getaway by Gather: Newly Renovated Near Beach & Hiking

Kailua, Hawaii, United States

Just a short stroll from turquoise water and powder-soft sand, Hale Alapi‘i Lanikai Getaway by Gather is a serene 4-bedroom, 3-bath retreat set in Kailua’s coveted Lanikai neighborhood. Recently renovated interiors meet breezy outdoor living, surrounded by tropical greenery and views of the famous Lanikai Pillbox ridge. Perfect for families and longer stays, the home includes a separate studio for added privacy.brbrWhat You’ll Love About Hale Alapi‘i Lanikai Getawaybr• Three-minute walk to a secluded swimming cove and ten minutes to Lanikai Beachbr• Main house plus an optional private studio, ideal for extended family or couplesbr• Bright open-plan living with modern finishes and abundant natural lightbr• Split A/C cooling all areas of the home for easy comfortbr• Lush yard, furnished lanai seating, and a peaceful residential settingbrbrLiving & DiningbrThe main house gathers everyone in a light-filled, open-concept space. Large windows frame palms and greenery, while comfortable seating invites relaxed conversation after a day on the sand. The adjacent dining area seats the crew for family meals, board games, and planning tomorrow’s adventures.brbrChef-Ready KitchenbrA renovated, fully equipped kitchen keeps cooking simple and social. Stone-look counters, generous storage, and a functional island make prep a breeze, from sunrise smoothies to casual island-style dinners.brbrOutdoor OasisbrStep outside to a private, tropical setting designed for unhurried days. Settle into cushioned lounge seating on the lanai, sip morning coffee as birdsong fills the air, and watch the light change over the Lanikai Pillbox. After the beach, rinse off, grill your favorites, and dine under the palms.brbrSleeping Quartersbr• Primary Bedroom – King bed, ensuite bath, Split A/Cbr• Guest Bedroom 2 – Queen bed, shared bath, Split A/Cbr• Guest Bedroom 3 – Two twin beds, shared bath, Split A/Cbr• Guest Studio – Queen bed, ensuite bath, private entrance, Split A/CbrbrExtrasbrApproximately 1,750 sq ft of interior space across the main house and studio, Smart TV, high-speed Wi-Fi, laptop-friendly setup, washer and dryer, ceiling fans, and free driveway parking. The separate studio adds flexibility for multi-generational travel or guests who want their own quiet space.brbrResort / Community HighlightsbrSet within a peaceful residential neighborhood in Lanikai. Private home, no shared resort amenities, with easy pedestrian access to beaches and the Pillbox Trailhead two blocks away.brbrNearbybrWalk to a calm swimming cove for snorkeling and paddling, or take a ten-minute stroll to world-famous Lanikai Beach. Launch kayaks toward the Mokulua Islets when conditions allow, hike the Lanikai Pillbox Trail for sweeping Windward views, and explore Kailua Town’s cafés, boutiques, and Whole Foods. HNL is the nearest major airport.brbrGood to Knowbr• This property is offered as a monthly rentalbr• The monthly rate applies in full regardless of the number of nights stayedbr• Minimum 30-day booking period requiredbr• Optional studio available for an additional fee, confirm pricing at inquirybr• Free parking in the drivewaybr• Exclusive use for the duration of the rental periodbr• TAT ID: TA-150-218-4960-01br• TMK: 430030350000brbrReserve your dates at Hale Alapi‘i Lanikai Getaway by Gather and enjoy easy island living between the beach, the Pillbox trail, and the relaxed charm of Kailua.

Bed

Bath

Sleeps

$312.12

/ Nightly

Private Vacation Home

Kailua Town & Kailua Beach

Kailua, Hawaii, United States

30 day, month to month rental.brbrHome is close to Kailua Beach and Kailua Town-shopping & restaurants. brbrThe home features a large family room and living room. Each bedroom has an AC unit and fans. The floor plan allows for separate spaces for everyone.brbrOffering a comfortable Kailua experience, it is a great place to relax and still close enough for trips to Waikiki and North Shore. brbrWalk to the Kalapawai Market for morning coffee, wind surf or kite board from the best spot on the island, rent a kayak or paddleboard, enjoy views of the Mokuluas, and have shaved ice at Island Snow later in the day.brbrBEDROOMS AND BATHROOMSbr3 bedrooms and 2 full bathrooms. The master suite has a Queen bed, Full bath and 2 closets. Bedroom 2 has a full bed. Bedroom 3 has 2 twin XL beds that you can easily put together into a king if needed. You can also use the queen size air mattress and 2 twin size air mattresses.brbrKITCHENbrThe fully stocked gourmet kitchen has everything you could possibly need to from wine glasses to pots, pans & rice cooker The kitchen opens into the dining area & large family room beyond which you can step into a private yard. An outdoor grill is available.brbrLIVING ROOMbrThere is spacious and bright living room with large sliding doors that open into a private courtyardbrbrEXTRAS:brPretty much everything you need for a memorable Hawaiian vacation are provided, down to the beach towels and boogie boards.brThe home also features: -Free Wi-Fi Connection throughout the property-Office den-HD Cable-Private driveway and Gate-Laundry Room w/ extra-large Washer and Dryer-Dishwasher-Outdoor Shower-Outdoor BBQ Grill-Beach Chairs, Beach Towels, and Snorkels, Free parking- AC: All the bedrooms have AC units and fans. brbrLOCATION AND ATTRACTIONS:brThis home is located just half a mile from the beach and 5 minutes' walk to Kailua Town. A hub for water sports such as windsurf, body board, kayak, paddle boarding and parasail.brPillbox Hike is 2 miles away. It’s a 30-minute climb up to two old military bunkers overlooking the North Shore coastline. The views are amazing.brbrTry the breakfast at Cinnamon’s in downtown Kailua; - Walk to Kapalawai Market to get freshly made sandwich or just off the grill burger before heading to the beach.br- Asian food restaurants include Champa Thai, Miyoshi Ramen, Saigon Noodle, or Tokonoma Sushi;br- Italian or Mexican include Assaggio, Buone Era, California Pizza Kitchen or Cactus;br- Try some fresh poke at Hibachi Grill, Foodland or Wholefoods brbrThis vintage home was built in 1949- one of the first residential neighborhoods in Kailua. It has a long local Kailua history with original antique windows and hardwood floors. It has been tastily renovated with a fully equipped kitchen, classic Hawaii charm and island decor. To make working and learning remotely from paradise more efficient, we have the highest available fiber optic Wi-Fi available on the island. 30 day rental house is on a main road within close proximity to Kailua town & Kailua Beach.brbrComfortable Kailua experience, it is a great place to relax away from the crowds but still close enough for trips to Waikiki and North Shore. brWalk to the Kalapawai Market for morning coffee, wind surf or kite board from the best spot on the island, rent a kayak or paddleboard and head to the Moku islands, and have shaved ice at Island Snow later in the day. Property number one four two zero two zero zero five four zero zero zero zero.

3

Bed

2

Bath

6

Sleeps

$290.84

/ Nightly

Private Vacation Home

Wake to the waves at “The Eddie” - 3 bed/2 bath

Kailua, Hawaii, United States

“The Eddie” - 3 bed/2 bathbr This elevated family living space with local charm and large second-floor lanai is perfectly located just feet from the sand and the vibrant Kailua Beach Park & Lanikai Beach. Whether you're here for a romantic escape, a family getaway, group retreat, or long-term Windward Oahu lifestyle, this unique accommodation offers everything you need for a carefree, oceanside life--however long you choose to stay!brHighlights: brPrime Location: Only a few steps to the Kailua Beach Park with walking paths and picnic spots as well as a stroll to the famous Lanakai Beach. Iconic restaurants and lunch spots are just around the corner. Close proximity and easy commutes to schools, hospitals, bases, airport. (Kaohao Public Charter School, Kailua Intermediate, Kalaheo High) brbrSpacious Comfort: Stylishly designed ~950 sq ft with fresh, crisp bedding with plenty of plush pillows (two queens and two twins). A queen air mattress is available to use for 2 additional sleeping spaces upon request.brPrivate Outdoor Space: Relax on your own 400+ sq ft covered lanai with ocean views and breezes to match or cook up some bbq on the outdoor grill. brFully Equipped: Fridge/Freezer, oven/stove, coffee maker, microwave, air fryer, toaster oven, outdoor grill, and dining essentials. Shared Washer and dryer included. Parking and all utilities included. brModern Amenities: High-speed Wi-Fi, smart TV, and air conditioning. Quiet, efficient appliances.brResort-style perks: Fresh linens, towels, toiletries, and many other thoughtful touches.brFamily fun: Pet-friendly. Heated outdoor beach shower, and stocked with everything from family activities (games, etc.) to complimentary beach gear (boogie boards, chairs, umbrella, sand toys, kayak, snorkels, etc)brScheduled cleaning service available for additional charge. brbr Book your stay now and let the ocean be your backyard! brbrAlso ideal for medium or long stays, work trips, travel nurses, military, or other 30+ day transient accommodation. brbrMinimum rental period: 30 consecutive days or more, as required by law. Discount available for 6 mo+ leases.

Bed

Bath

Sleeps

$1597.23

/ Nightly

Private Vacation Home

Upscale Kailua Getaway: Steps to Swim Beach!

Kailua, Hawaii, United States

An unforgettable Hawaiian escape awaits at this luxurious 3-bedroom, 2-bathroom Kailua vacation rental home! Sip your coffee on the deck, then walk to Lanikai Beach to enjoy the morning waves. Spend your days relaxing in the private pool, lounging in the hammock, or kayaking in Kailua Bay. When you’re ready to explore the island, hike in the Diamond Head State Monument and check out the attractions in Honolulu. In the evening, prepare a meal in the fully equipped kitchen or grab some local eats!brbr-- THE PROPERTY --brbrTAT License No. TA-025-999-1552-01 | GE Tax No. GE-025-999-1552-01 | Private PoolbrbrBedroom 1: King Bed | Bedroom 2: King Bed | Bedroom 3: 2 Twin BedsbrbrINDOOR LIVING: 3 Smart TVs, dining table, laptop-friendly workspace, ceiling fansbrOUTDOOR LIVING: Furnished lanai w/ Smart TV, gas grill, patio w/ dining area & lounge seating, shower, hammock, beach chairs, beach towels, private yardbrKITCHEN: Dishwasher, gas stovetop, double oven, refrigerator, microwave, breakfast bar w/ seating, cooking basics, dishware & flatware, coffee maker, coffee grinder, blender, toaster, toaster oven, Crockpot, spices, trash bags & paper towelsbrGENERAL: Free WiFi, 2 split A/C units (Bedroom 1 & Bedroom 2), complimentary toiletries (starter set of toilet paper, paper towels, hand soaps, dish soap, laundry soap, dishwasher tablets, bath soap, kitchen bags, and a new sponge), linens & towels, in-unit laundry, laundry detergent, hair dryer, hangers, iron & board, keyless entrybrFAQ: 3 exterior stairs for accessbrPARKING: Garage (1 vehicle), driveway (1 vehicle), free street parking (first-come, first-served)brbr-- THE LOCATION --brbrBEACHFRONT FUN: Lanikai Beach (across the street), Kailua Beach Park (1.1 miles), Kalama Beach Park (1.9 miles), swimming, kayakingbrOUTDOOR RECREATION: Pillbox Hike (0.6 miles), Kawainui Marsh Wildlife Sanctuary (4.9 miles), Honolulu Watershed Forest Reserve (7.0 miles), Heʻeia State Park (8.9 miles), Diamond Head State Monument (18.0 miles)brNEARBY SITES: Ho’omaluhia Botanical Garden (8.9 miles), The Byodo-In Temple (10.3 miles), Honolulu (13.5 miles), shopping, historic sites, family-friendly attractionsbrAIRPORT: Daniel K. Inouye International Airport (17.3 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: This property requires 3 exterior stairs for accessbr- NOTE: The complimentary toiletries provided are toilet paper, paper towels, hand soaps, dish soap, laundry soap, dishwasher tablets, bath soap, kitchen bags, and a new sponge. After these run out, any additional toiletries must be purchased by the guest

Bed

Bath

Sleeps

$2633.63

/ Nightly

Private Vacation Home

KAILUA BEACH VILLA - 1990/NUC-1798

Kailua, Hawaii, United States

Additional guest fee of $98 per person per day applies to parties over 10 people. Additional service fee and tax will apply.brA private home with eight bedrooms on Kailua Beach (Voted Number One Beach in America). (Adjacent 2-bedroom Guest Cottage also available to rent)br*There are 2 shopping centers within 10 minutes, and the Ala Moana Shopping Center, the largest shopping center in Hawaii and ranked 7th largest shopping center in the United States, is within 30-45 minutes.br* Ideal for family vacation, family reunion, anniversary br celebration, or corporate retreat.br* Stroll on six miles of white sand beach, surf, swim, and snorkel.br* Two golf courses within ten minutesbr* Go sightseeing, visit busy touristy Waikiki, shop for 'things Hawaiian,' visit Polynesian Cultural Center, then come home to the cabana, swimming pool (not heated), and barbecue.br* Enjoy the morning sunrise peeking over the horizon and glistening ocean waves.br* Visitors have said 'this was the best vacation spot ever.'brbrKeywords: Luxury House & Guest Housebrbr*Visit Property No 64714 on Website for a smaller family group of up to 4 people.

8

Bed

4

Bath

14

Sleeps

$712.32

/ Nightly

Private Vacation Home

Peaceful Oceanfront Home Near Downtown Kailua w/ BBQ & AC: Kai Mele

Kailua, Hawaii, United States

**Welcome to Kai Mele** in Kailua, Hawaii, a delightful retreat perfectly positioned to embrace ocean and garden views within its expansive 1,690 square feet of space. This charming vacation condo offers a harmonious blend of island living and modern convenience, accommodating up to six guests across three beautifully appointed bedrooms.brbr**What You’ll Love About Kai Mele**br• Oceanfront living with panoramic views br• Cozy beach cottage ambiance with modern upgrades br• Spacious lanai ideal for morning coffee or sunset dinners br• Short stroll to the beach, perfect for family outings br• Thoughtful amenities ensure a relaxing stay brbr**Living & Dining** brKai Mele boasts a bright and airy living and dining area, seamlessly integrating comfort and style. Enjoy meals at a dining table that comfortably seats six, all set against the backdrop of stunning ocean views. The cozy living room features new furniture, providing a relaxing spot to unwind after a day of island exploration.brbr**Chef-Ready Kitchen** brCook with ease in the updated, fully-equipped kitchen featuring all the essentials—refrigerator, stove, microwave, dishwasher, and more. Whether you're preparing a simple breakfast or a delicious dinner, you’ll find everything you need right at your fingertips.brbr**Outdoor Oasis** brStep outside to your oceanfront lanai, featuring a brand new lounge setup, perfect for soaking in the gentle island breezes. The expansive private yard invites you to enjoy sunset gatherings or moments of solitude amidst tropical landscaping, offering both shade and sunshine.brbr**Sleeping Quarters** br• Primary Bedroom – King bed, ensuite bath, ocean and garden views br• Guest Bedroom 2 – King bed, split AC br• Guest Bedroom 3 – Queen bed, ocean and garden views, split AC brbr**Extras** brEnjoy thoughtful amenities throughout the property including high-speed Wi-Fi, a safe for your valuables, a washer and dryer, and beach essentials such as chairs and towels. The property also includes air conditioning, a Bluetooth speaker, and essential bathroom amenities to enhance your stay.brbr**Resort / Community Highlights** brWhile this is a private retreat, enjoy access to nearby local attractions offering fishing, watersports, hiking, and shopping. The inviting community atmosphere melds perfectly with the proximity to the beautiful island beach.brbr**Nearby** br• Walk to beautiful beaches for sun and surf br• Short drive to Kailua's vibrant shops and dining options brbr**Good to Know** br• This home is offered as a monthly rental. Full-month occupancy is not required, but rates are fixed and not prorated.br• 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• Standard occupancy is 6 guests, with a maximum of 6. Extra guest fees apply if approved.br• Split A/C units are in the main living area and bedrooms; the kitchen does not have A/C.br• An Electric Security Deposit of $400 is required. This covers potential excess electricity usage. A maximum of $250 in electricity usage is included; unused portions are refunded after check-out.br• The property is exclusively available to renters for a full 30-day rental period. No other occupants are permitted during that time. br• TA-160-294-7072-01br• TMK 430130320000brbrReserve your dates now for a genuine taste of island life at Kai Mele, where relaxation and adventure await in perfect harmony.

Bed

Bath

Sleeps

$494.64

/ Nightly

Private Vacation Home

Happy House on Exquisite Kailua Beachside Property!

Kailua, Hawaii, United States

Kailua Beachside: Charming beach house steps from the white sands of beautiful Kailua Beach. Nestled in a large, private garden property, enclosed by stone walls with palms, banana trees and beautiful tropical gardens. Very safe and fun for kids, great for families, with lots of room to roam and hang out. The large private outdoor shower is everyone’s favorite.brbr3 bedrooms and 2.5 baths make it comfortable for 6 people. Living room, TV/reading den and laundry. Outdoor patio with table, chairs for 8 and large umbrella right outside living and dining. Fully equipped for cooking if you want to do your own, and minutes from Kailua Town if you want to eat out. It’s a short walk to the local favorite Kalapawai Market for coffee, or Buzz’s steak house. Or leave your car behind and explore Lanikai on the bikes.brbrWake up to gentle tradewinds in the red bedroom, with corner windows and stunning views of the sunrise through towering coconut palms. Enjoy the charm of the blue room with traditional Hawaiian vaulted ceilings, ceiling fan and large windows. Tucked away on its own with a full bathroom, a private patio, a/c and glimpses of the Ko’olau Mountains, the mango room is the largest bedroom, with both a king and a twin bed.brbrEvery room has views to the garden and windows that open to tradewind breezes. Comfortable tropical-themed furnishings and art are tasteful and cool. Treat yourself to your own piece of paradise near one of the best beaches in Hawaii. brbrNon-smoking, children are very welcome!br brThis property is rented for periods of 30 consecutive days or more at any one time. The property will be made exclusively available to the renter for a full period of 30-days, regardless of length of actual stay. The 30-day rental period will be communicated to guest upon booking. For questions, please contact us. Aloha!brbrHawai`i Tax I.D. No. 201-396-2240-01br brbr brbrbrKeywords: Beachside House

Bed

Bath

Sleeps

$373.15

/ Nightly

Private Vacation Home

Close to Kailua Beach-AC's-Renovated/Upgraded-Fenced Backyard-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. brbrThis is a fully furnished & renovated/updated 3/2 rental with a big, fenced & shady yard with tropical trees and plants, including mango, breadfruit, lemon, lime, coconut, avocado, tangerine, lychee & dragon fruit. You'll love cooking in this newly upgraded kitchen with lots of storage and counter space, there's even a gas cooktop. Large dining table, patio and gas grill on the backyard patio. Split AC's keep the entire house cool when needed. A well-behaved & quiet pet would be considered. Two car garage with workbench and lots of driveway parking. A 10-minute walk to the closest Kailua Beach access, Nico's restaurant and the Aikahi Park Shopping Center. Centrally located to reach other areas of the island quickly, near the H-3 highway & Marine Corp Base Hawaii.

3

Bed

2

Bath

7

Sleeps

$959.39

/ Nightly

Private Vacation Home

4BR Mokulua Seaside w/ Private Studio, Steps to the Beach

Kailua, Hawaii, United States

Mokulua Seaside by Gather is a refined oceanside escape that brings together luxury, space, and the beauty of Lanikai. Just one house from the sand on Kailua’s coveted Mokulua Drive, this four-bedroom, four-bathroom retreat spans 3,316 square feet of interior living and accommodates up to ten guests in style. With indoor-outdoor flow, a separate studio suite, and direct access to world-class waters, this monthly rental offers a front-row seat to the Lanikai lifestyle.brbrWhat You’ll Love About Mokulua Seasidebr* Just 30 feet from beach access on the east end of Mokulua Drivebr* Expansive upstairs primary suite with ocean-view lanaibr* Separate studio suite above garage with full bath and kitchenbr* Covered lanai, gazebo, and lawn for outdoor dining and lounging* Open-concept living with vaulted ceilings and sliding glass doorsbr* Perfect launch point for snorkeling, kayaking, and paddle adventuresbrbrLiving & DiningbrA double-door entry welcomes cool ocean breezes into the high-ceilinged living room. Designed for gathering, the lounge opens to a back deck and lawn via sliding doors, blending island air with comfortable interiors. The dining area for eight and a rustic breakfast bar make mealtimes effortless, while the gazebo in the garden provides a shaded retreat for coffee or cocktails.brbrChef-Ready KitchenbrAt the heart of the home, the kitchen is equipped with expansive counters, premium appliances, and ample prep space. Its central location keeps the cook connected with the flow of the home, indoors and out.brbrOutdoor OasisbrFrom morning swims to evening Mai Tais, the outdoors is integral here. The covered lanai invites alfresco dining, the lawn connects the main house and studio, and the gazebo offers garden serenity. Rinse off after the beach in the outdoor shower, or simply watch the palms sway from a shaded swing.brbrSleeping Quartersbr* Primary Suite – Cal King, ensuite bath with soaking tub and walk-in shower, partial ocean view, private lanai, garden view, central A/Cbr* Guest Bedroom 2 – Queen, ensuite bath, garden view, ceiling fan, central A/Cbr* Guest Bedroom 3 – Queen, ensuite bath, garden view, balcony/deck, ceiling fan, central A/Cbr* Guest Bedroom 4 – Two Queens, ensuite bath, garden view, balcony/deck, lounge area with TV and kitchenette, split A/CbrbrExtrasbrHigh ceilings, luxury bathrooms, smart TVs, furnished interiors, washer/dryer, and a fully equipped studio suite above the garage extend flexibility and comfort for larger groups.brbrNearbybrWalk: Lanikai Beach, Mokulua Islands outlook, Pillbox Trail, kayaking and SUP launchbrShort Drive: Kailua Beach Park, Kailua town shops and dining, golf, and additional hikesbrbrGood to Knowbr* Interior: 3,316 sq. ft.br* Monthly rental only; fixed 30-day rate (no prorating)br* Exclusive to one renter per 30-day periodbr* Transient Accommodations ID: TA-013-318-7072-01 br* TMK: 430040990000brbrWith its prime location and thoughtful design, Mokulua Seaside by Gather is more than a home—it’s an invitation to embrace the rhythm of Lanikai. Reserve your 30-day stay and experience Kailua’s coastal beauty at its finest.

Bed

Bath

Sleeps

$4253.84

/ Nightly

Private Vacation Home

Luxury beachfront villa on a world class beach in Kailua, HI

Kailua, Hawaii, United States

As you enter the electric remote gate into this luxurious villa you will feel this sense of peace and calmness come over you.brThis luxurious Kailua Villa is located on the ocean which is hidden in the best part of Kailua. Wake up every day to the most amazing sunrises and step onto the beach from your very private and modest oceanfront estate. This Beachside Villa is the perfect estate whether you are a small family wanting total privacy while having an intimate vacation or a larger group looking for a large and open space with full suite sleeping quarters. brThis property captures the calmness of Beachside in Kailua along with the outdoor beauty as there are tons of large windows and doors creating endless ocean and mountain views. This amazing spacious luxury villa is surrounded by the beauty of the Pacific Ocean and white sandy beaches where Kailua Beach has year after year been named one of the top beaches in the world.brThis one-of-a-kind elegant beachfront villa is complemented by a lovely interior designed grand entertaining room with full A/C and huge windows with large sliding glass doors that lend to the indoor-outdoor living. Your private chef will create the perfect meal for you and your family and friends in this gourmet kitchen outfitted with subzero and wolf appliances.brEvery Bedroom has full en-suite bathrooms along with luxurious mattresses for that perfect night’s sleep. Each room affords its very own level of comfort and privacy with amazing views throughout. The upstairs primary room has vaulted ceilings, 2 lanais, and a spa-like bathroom with floor-to-ceiling windows overlooking the ocean and Mokes with a vessel tub and a very expansive walk-in shower. brThe palatial villa offers a total of 6 bedrooms, 5.5 Bathrooms with the capability to sleep 18 people. This home comes with luxurious linens, bathing towels, and a starter set of toiletries including lotions, shampoo, and conditioner. This kitchen has more than anything you or your private chef could want. All you need to bring is your swimsuit and toothbrush. For your daily fun at the beach, we have included Beach Chairs, Umbrellas, Beach Towels, Boogey Boards, SUP Boards, and Kayaks.brThe monthly rent includes water/sewage, gas, internet w/ WIFI, monthly gardening service, jacuzzi, and weekly maid service. To see the video go to 25 Wilikoki dot com.brNot included in rent are any electric bills over $450/month, GET and TAT (Taxes) charges along with required renters insurance which we can help you acquire if needed. There is also a vehicle available for rent if needed. Any utilities over $450/mo. will be taken out of the security deposit and proof of expenses will be provided.br90 -Day Rentalbrbr***This vacation home has been registered as a Transient Accommodation with the State of Hawaii - HAWAII TAX ID TA- TA- TA-048-077-3632-01

6

Bed

5

Bath

18

Sleeps

$365.55

/ Nightly

Private Vacation Home

Available and legal for stays less than 30 days

Kailua, Hawaii, United States

Yes, we are a legal, licensed bed and breakfast. We are available and legal for stays of less than 30 days. We are not effected by the recent controversy which effect unlicensed bnbs in Honolulu. See license numbers below.brbr Walk to beach from Hawaii Sheffield House. Located just 10 houses from Kailua Beach the Garden Suite has a queen bed and single bed sized day bed/with trundle and a delightful window seat which is also the size of a single bed. It has a private entrance and a private bath. brbrThe Garden Suite is a ground floor unit and has a one step entrance. There are ceiling fans in all of the rooms as well as quiet split system air conditioning. Yes, we are in the tropics. Yes, there are geckos , anoles and chameleons and insects. Yes, we use pesticides.brbrSheffield House is located in a neighborhood only a short walk (10 houses) from secluded Kailua Beach - one of the best beaches on Oahu. Sunbathe or swim in the cool water or just walk on the white sandy beach. On breezy days watch the windsurfers, or look for sea turtles between Flat Island and Kailua Beach Park. brbrTake advantage of waking up early from the time zone change and walk down to the beach to watch the sun rise out of the ocean over the Mokulua Islands. Or once a month check out the full moon rise out of the ocean. Bird watching is superior over the canal at Kailua Beach park or in Kawainui Marsh. See stilts, herons, or iwa birds. br. br A parking space for this unit is in the driveway just steps from the entry to this unit.brbr It rents from $259-$325 per night for a party of two. A $30 extra per person charge. At this time we are not taking children under the age of 3 in this unit . We only take small children when 30018 is rented together with VRBO 572484 as a two bedroom two bath unit..brbrIt has Mexican tile floors and Hawaiian quilts on the beds.brbrThe kitchenette in the Garden Suite has kitchen cabinets with granite counter tops, a half size refrigerator, hot plate, toaster, microwave, electric frying pay, and coffeemaker. It has an outdoor garden area with umbrella, table and 4 chairs . Towels, beach towels and paper towels are provided. Yes, we provide a hair dryer. A charcoal grill is provided upon request for your use in the garden area.brbr We offer internet and high definition cable TV.brbrIt has off street parking, phone, tv, and wifi. A complimentary breakfast or snacks of: Hawaiian juice, fruit and coffee or tea, is provided for your first morning. Upon arrival or while you are here you will meet Paul or Rachel Sheffield. Yes, we need to know your arrival timebrbrCheck in is 3 p.m. and check out is at 10 a.m. There is a $30 per person extra person charge. No refunds will be given . Due to our residential area we have a quiet time between 10 p.m. and 6:30 a.m. Also note that there is a community pool only 13 houses up the street. Also, there are 2 coin operated laundromats 1/3 of a mile away.brNote we are a non smoking property and this a NON SMOKING UNIT. br br We love sharing our corner of paradise with our guests.brbrWe have offered hospitality for over 30 years in Kailua, HawaiibrYes, we have a minimum night stay. However, always inquire to Hawaii Sheffield House as we will take shorter stays if it is between longer stays or last minute if the room is available! Hawaii Sheffield Housebrhas been in business over 25 years. ( Yes, we have been in business so long we are older than the internet! We are still listed in guidebooks such as the Lonely Planet , Frommers, and Foders. We have been listed in the magazine Coastal Living and the Los Angeles Times ! ) brbrWe have recently become interested in astronomy. Ask about upcoming events at the Windward Community College observatory.brbrbrHawaii Sheffield HousebrKailua , Oahu Hawaii 96734brbrHawaii License Number - HI TA137-360-9984-01brCity and County of Honolulu -License No. 90/BB-0077brbrThe Ginger Studio VRBO 572484 also has a queen bed. Rented together both can sleep a total of 4 people in beds, plus 1 on the single daybed (with trundle) couch or a small child in the single bed sized window seat.brbr:Kailua, Vacation Rental, Suite , Studio, Walk to Beach, Walk to Kailua town. Bed and Breakfast, Kailua Hotel, Kailua Motel, Oahu Motel, Oahu Hotel, Kailua Home, Kailua House, Hawaii Near Beach, Convenient to Kailua Whole Foods. Can Sleep 5 when rented with adjoining VRBO 572484.brVideo here:brhttps://tours.360aaa.net/public/vtour/display/906421#!/

Bed

Bath

Sleeps

Select Dates for Price

Private Vacation Home

Kailua Oceanfront Villa with Heated Pool & Spa

Kailua, Hawaii, United States

Relax in the beautiful three-bedroom seaside villa in Kailua, where soothing sea waves and soft breezes carry you off. Indulge in the outdoor pool, where you can soak up the sun and relax and end a day of hiking or golf with a massage in the oceanside hot tub. Stay connected with the high-speed WiFi, and enjoy the convenience of the in-unit washer and dryer. Curl up on the couch and stream your favorite shows on the smart TV. In the cool evenings, there's a firepit on the ocean deck to relax at the end of a day while listening to the sounds of the ocean waves. The deck has cafe lights to provide just the right amount of light to enjoy the evenings. brbrVenture out and explore the top nearby attractions, including the vibrant Honolulu Harbor, the bustling Ala Moana Center, and the lively Waikiki Beach Walk, all within a short drive. Back at the property, you'll find a fully stocked kitchen, perfect for whipping up delicious meals. Savor your culinary creations at the dining table, or step outside and fire up the grill for an al fresco dining experience. brbrUnwind in the comfortable bedrooms, each with its own bathroom, and enjoy the luxurious amenities, including air conditioning, linens, and a hair dryer. Venture out to the balcony and soak in the breathtaking ocean views, or relax on the beach loungers with a good book. With games, a stereo, and toys for the kids, there's something for everyone to enjoy at this enchanting beachfront retreat.brbrThis house has never been listed on Craigslist. Any listing besides VRBO is a scam and should be avoided. The owner will not honor any rental from Craigslist.

Bed

Bath

Sleeps

$1026.97

/ Nightly

Private Vacation Home

Breathtaking Kona Estate. Panoramic Ocean Views, Waterfalls, Pool and Spa.

Kailua, Hawaii, United States

From the moment you arrive at Hale Wailele (Waterfall House), tropical scenes take your breath away. Perched above the Kona Coast, this spectacular home invites you to unwind in complete comfort. Enjoy expansive ocean views, indoor-outdoor living, and evenings spent watching the sky melt into the sea. This spacious home with floor to ceiling windows in the great room looking out onto fountains in the pool with an incredible ocean view beyond the palm trees and torches connects you to the ocean, to nature, and to each other. The architecture of the home highlights open spaces, cooling breezes and peaceful privacy. Hale Wailele surrounds you with beautiful architecture and artistic touches such as arches, niches, cathedral ceilings, gorgeous paintings, music and sculptures throughout.brbrOur home is in a quiet neighborhood where most people live with open windows. Therefore, we do not offer it for weddings, meetings, or parties. The use and enjoyment of the house, pool, etc. is limited to the individuals listed on the rental agreement. We will only confirm reservations that give details about the group, purpose of the trip, and reassurances about being respectful and keeping noise at normal conversation levels. Disruptive behavior and excessive noise are not permitted.brbrThe primary bedroom is furnished with a king bed, TV, garden tub with separate shower, Toto bidet commode, and infra-red sauna. brbrBedroom two has a king and a queen bed, and full guest bath. brbrBedroom three has a king bed, and sitting area and full guest bathbrbrThe den has a TV, recliner, and a pullout sofa. It opens to a side yard perfect for game of croquet or bocce. The den and bedroom three share the full guest bath.brbrThe loft looks over the great room, has a computer desk, foosball table, 2 queen futons and 1 double futon.br The gourmet kitchen features stainless appliances and two adjoining dining areas with ocean views. There are also two bar areas- all focused on the gorgeous view and pool area.brbrIf you prefer to cook and dine on the lanai, we have a large stainless gas grill, and an Evo grill. There is plenty of seating at two lanai tables.brbrTropical gardens surround the home on the spacious one acre lot. Outdoor enthusiasts will love the orchid garden, herb garden and extensive assortment of flowers and fruit trees including, papaya, lemon, lime. apple-banana, avocado, fig, and mango. brbrThere are 3 smart-home features installed. 2 Nest doorbells, one at the front door and one at the side door (both facing parking areas); and a smart lock, that will be programmed with a code to unlock the door, for your convenience. brbrAlso a quick note about our animal friends :)brbrGeckos: Because of the tropical climate and vegetation in Hawaii you are likely to see our friends the geckos. They are a beautiful bright green with a few magenta spots. They have no teeth, are harmless, and considered good luck on the islands because they eat harmful insects. They are most easily spotted outside by lights waiting for dinner, but can fit through the smallest openings and are sometimes seen inside as well. If you see one inside and prefer not to have its company, please just toss a hand towel over it and release it into the gardens. brbrBirds: There are many birds around the house and throughout the neighborhood including Brazilian cardinals, finches, doves, exotic pheasants, chickens, and others. While they are fabulous to watch and a favorite part of the tropics, they can also be noisy for light sleepers. We recommend adding a sleep app to any smart phone or bringing earplugs if you think you might be bothered. brbrPlease include the correct number of guests, information about your group, and purpose of your trip with your inquiry. Mahalo!

Bed

Bath

Sleeps

$1002.11

/ Nightly

Private Vacation Home

Hale Ohana: Kailua Retreat w/hot tub, Tropical Pool, Walk to Beach

Kailua, Hawaii, United States

Set along Kailuana Loop on Oahu’s beautiful windward coastline, Hale Ohana by Gather offers a spacious, family-friendly retreat designed for easy island living. With nearly 3,000 square feet of indoor-outdoor space, a private pool and hot tub, and a dedicated guest wing and game room, this home brings comfort, fun, and connection together in one inviting place.brbrWhat You’ll Love About Hale Ohanabr• Private pool, hot tub, upper deck BBQ, and rooftop deck with peekaboo ocean viewsbr• Game room with ping pong and classic Spider-Man pinballbr• Spacious floor plan with seamless indoor-outdoor livingbr• Gourmet kitchen with premium appliances and two islandsbr• Split A/C throughout, plus ceiling fans in all bedroomsbr• Multiple indoor and outdoor lounge areas designed for families and groupsbrbrLiving & DiningbrLarge sliding doors open the main living areas to the outdoors, creating a bright and welcoming place to gather. Relax in the comfortable seating areas or enjoy meals in the spacious dining room overlooking the garden. With several lounges throughout the home, everyone can find space to unwind.brbrChef-Ready KitchenbrWith two islands, top-tier appliances, warm wood cabinetry, and generous prep space, the renovated kitchen is ideal for everything from casual breakfasts to full family dinners. Steps away, the upper deck offers a built-in BBQ with pool and treetop views.brbrOutdoor OasisbrDays move easily between the covered lanai, sun patio, and private pool. A tranquil waterfall feature sets a relaxing tone while the hot tub invites evening soaks. The rooftop deck is the perfect place to enjoy soft trade winds and peekaboo ocean views. Outdoor seating and dining spaces make al fresco living effortless.brbrSleeping Quartersbr• Primary Bedroom – King bed, ensuite bath with shower and double sink, garden and pool views, split A/C, ceiling fanbr• Guest Bedroom 2 – Queen bed, garden view, split A/C, ceiling fan, loveseat, shared bathbr• Guest Bedroom 3 – Double bed, split A/C, ceiling fan, shared bathbr• Guest Bedroom 4 (Guest Wing) – Queen bed, split A/C, ceiling fan, located beside the game room; full bath nearby with exterior accessbrbrExtrasbr• Game room with Spider-Man pinball, ping pong table, and lounge spacebr• High-speed Wi-Fibr• Split A/C throughoutbr• Washer and dryerbr• Beach gear including chairs and umbrellasbr• Multiple lanais and outdoor seating areasbrbrCommunity HighlightsbrExplore the nearby coastline with ease. Public beach access is a short walk from the home, while iconic spots such as Waimanalo Beach, Makapu’u Point Lighthouse, and the Pali Lookout are just minutes away. Kailua’s dining, shopping, and golf courses are close by, and Nico’s restaurant is within walking distance.brbrNearbybrNearby – Walk:br• Public beach access (5–7 minutes)br• Nico’s restaurantbr• Local shops and cafésbrbrNearby – Short Drive:br• Kailua Town dining and shoppingbr• Hiking at Makapu’u Lighthouse and Pillbox trailsbr• Waimanalo Beach and water activitiesbrbrGood to Knowbr• This home is offered as a monthly rental; the full monthly rate applies regardless of nights stayedbr• The property will be made exclusively available to the renter for a full period of 30 days, and no one else may occupy the home during that timebr• Rates based on a 30-day rental period; rates and fees are subject to change, and minimum stay requirements may applybr• Inquire for possible discountsbr• Standard occupancy is 8; maximum occupancy is 10 with additional guest feesbr• Max included electricity usage is 350 dollars; excess usage is subject to additional chargesbr• This property requires a 500-dollar Electric Security Deposit, refunded after checkout if usage remains within the allowable limit and no additional charges applybr• Split A/C throughoutbr• Online bookings are subject to manager or owner approvalbr• Neighborhood beach access is available only for stays of six months or longer; all other guests may use the nearby public beach access point (5–7 minute walk)br• TA-139-302-3488-01br• TMK 430830350000brbrLet Hale Ohana by Gather be your home base for slow mornings, relaxed afternoons, and unforgettable days on Oahu’s beautiful windward shore.

Bed

Bath

Sleeps

$592.57

/ Nightly

Private Vacation Home

Resort-like, Kailua Beach, Lanikai Beach, Private Pool, AC, Tropical Retreat

Kailua, Hawaii, United States

brWe offer a solar-heated Pool, AC , WIFI, Kayaks, and up to 50% Discounts on monthly rentals. This property is a 2 1/2 to 3 min walk from the sandy beach of Lanikai (the property marker shows the property location incorrectly).brWalk through the entry gate, and find yourself in the middle of your own personal resort. A lush tropical yard greets you as you walk to the front door of this unique traditional beach-side cottage in the up-scale Lanikai neighborhood. The professionally landscaped property creates a welcoming and cool setting even on hot summer days. You just might have trouble pulling yourself (and the kids) away from our beach-entry pool to get over to Lanikai beach with its powder-soft sand, 200 meters away. The pool is always a great hit with young and old with its lagoon feeling. This combined with this property's beach-side location, makes enjoying the unique feel of Lanikai a highlight. brWe are looking forward to sharing our little piece of paradise with you!brbrWindward beaches with their powdery soft sand and gentle protected waters are among the best swimming beaches in the world. The Mokulua Islands off shore have been included in numerous advertisements and movies. brThis home is one of the last few remaining Hawaiian-style beach cottages offering its renters an exceptional tropical setting and truly unique Hawaiian experience. The house has an open floor-plan with an extensive patio deck, which is ideal for island-style indoor-outdoor living and delights with a casual elegance. It even boasts a rare fireplace (for Hawaii). brIt is updated to today's standards, and tastefully decorated, while maintaining its traditional charm. There are two master bedroom suites and one bedroom with an adjoining bathroom off the hallway. All of the bedrooms have wall-unit air conditioning. The 'great room' containing the kitchen, living room, den, and dining area has central air conditioning. The kitchen has marble counters and modern appliances. Hardwood floors throughout are easy on your barefoot feet. brWe welcome families with children. Our typical group is 4 adults plus 2 children. Our max. is 6 adults at any time. We welcome children two-yrs and above. If you have other needs, please inquire.brbrADDITIONAL INFORMATION:brbr1. The rental will be exclusively reserved for one rental party for 30 consecutive days, even if the rental party occupies late or vacates early, and only uses a portion of the time booked. We require a 30-day rental contract.brbr2. Rates and fees are subject to seasonal change, special discounts, how many bedrooms are rented, and if shared property use is available or requested. We give up to 50% discounts. Please inquire. brbr3. If you are unsure about your guest list, or your guest list changes, please contact the owner before making final arrangements with your guests. Occupancy is limited to the maximum number of occupants on the rental contract for each 30-day consecutive booking period. Guest names and ages must be the same as on the rental contract. We require the main renter, who signs the rental contract, to be physically present throughout the rental period. The house rules listed in the rental contract forms part of the VRBO accepted house rules signed by renter. brbr4. Your safety matters. This property features an exterior security camera which provides a driveway view and a street-side view of the front gate. The camera does not look into the yard or any interior spaces. brbr5. We strive to provide guests with prompt attention when issues arise. Therefore we have engaged an owner representative to help us out in addition to our caretaker services. brPlease see the glowing reviews of previous guests about our representative/caretaker services. brThe owner representative will maintain guests privacy at all times and not enter the main property unless invited or needed. You are on a holiday... we (owner and service providers) are here to make your stay perfect! To accommodate this, we have a fenced-off, detached, and completely separate functioning caretaker house with its own entrance and amenities privately situated on the other end from the main house of our 16'000 sqft property.

Bed

Bath

Sleeps

$1412.63

/ Nightly

Private Vacation Home

Gorgeous Oceanfront Home w/Mokulua Isle Views, Yard & AC: Lanikai Oceanside

Kailua, Hawaii, United States

Wake up to panoramic views of the Mokulua Islands at Lanikai Oceanside 5 Bedroom, a rare oceanfront retreat blending historic charm with modern coastal design. Once the summer home of Princess Abigail Kawānanakoa, this expansive estate offers direct access to world-famous Lanikai Beach, tropical gardens across more than half an acre, and bright interiors designed for gathering with family and friends.brbrWhat You’ll Love About Lanikai Oceanside 5 Bedroom br* Oceanfront location with sweeping views of Lanikai Beach and Mokulua Islandsbr* Direct beach access just steps from your back lawnbr* 4BR/3BA main house + detached 1BR guest house with full kitchenbr* Historic significance as the former summer home of Princess Kawānanakoabr* Recently renovated with mid-century modern coastal designbr* Expansive yard and gardens with postcard-worthy oceanfront seatingbrbrLiving & DiningbrInside, vaulted ceilings, walls of glass, and tropical-chic accents create a breezy setting that flows seamlessly to the outdoors. Two living areas offer space to gather: one more formal, one casual and cozy for movie nights. The dining space is designed for long, relaxed meals with ocean views just beyond the windows.brbrChef-Ready KitchenbrThe sleek, updated kitchen features ocean-view counters, stainless appliances, and everything you need to prepare island-inspired meals. A separate full kitchen in the guest house ensures added convenience for multi-family groups.brbrOutdoor OasisbrSettle into a lounge chair on the oceanfront lawn as kayakers paddle toward the Mokuluas. Expansive gardens, swaying palms, and multiple lanais offer both sunny and shaded escapes. A large backyard with direct beach access means the sand and sea are always just steps away.brbrSleeping Quartersbr* Primary Suite – Cal King bed, ensuite full bath with dual vanities, lanai, split A/C, ocean viewsbr* Guest Bedroom 2 – Cal King bed, shared full bath, lanai, split A/C, ocean viewsbr* Guest Bedroom 3 – Queen bed, shared full bath, lanai, split A/C, ocean viewsbr* Guest Bedroom 4 – Queen bed, shared full bath, lanai, split A/C, ocean viewsbr* Guest House Suite – Queen bed, ensuite full bath, private lanai, split A/C, full kitchen and living areabrbrExtrasbr* High-speed Wi-Fi and multiple smart TVsbr* Washer/dryer, beach gear, and parkingbr* Expansive property on 25,000+ sq. ft. lotbr* Historic mid-century design details and tropical art throughoutbrbrNearbybr* Walk: Pristine Lanikai Beach and the Lanikai Pillbox Trail for iconic sunrise viewsbr* Short Drive: Kailua town (5 minutes) for cafés, boutiques, and local markets; Waikiki (30 minutes) for shopping, dining, and nightlifebrbrGood to Knowbr* Minimum 30-day rental; full exclusive use of the propertybr* Utility fee of $1,000/month applies to stays of 21 days or longerbr* Standard occupancy is 10 guests (max occupancy 10)br* Pets not allowed; no smoking permittedbr* Hawaii Tax ID: TA-141-510-3488-01br* TMK: 430030630000brbrReserve your stay at Lanikai Oceanside 5 Bedroom and experience oceanfront living with a sense of place, history, and effortless island style.

5

Bed

4

Bath

10

Sleeps

$991.01

/ Nightly

Private Vacation Home

BEACH FRONT KAILUA ESTATE, OCEAN VIEWS, HUGE LUSH PRIVATE HISTORIC PROPERTY

Kailua, Hawaii, United States

Recent Updates: Newly constructed upstairs deck, Brand new window ac unit in master bedroom, new patio furniture, new sectional couch in living room. brbrOur beach estate is located on over an acre of land, just one house back (a quick 30 second walk down a sandy beach path) to one of the best white sand beaches in Hawaii. This is the only beach in Hawaii to consistently show up as one of the top ten beaches in the world lists. Unlike most beaches in Hawaii our beach is mostly free of tourists so you can actually have space and relax. On weekdays you will virtually have the entire beach to yourself!brbrOur 2200 sq foot home neighbors some of the finest properties on Oahu, just doors down from where the Obama family stays when they come to Hawaii. One of the very few properties that is actually a LEGAL vacation rental and has been since the early 90's, so you can be assured that your rental will be available when you arrive! brbrOur property offers the utmost relaxation and tranquility. Feel the white sand between your toes, bask in the warm Hawaiian sun, dive into the crystal clear aqua waters, and be glad you've made the best choice for your Hawaiian vacation! brbrOur two story house offers Ocean and Mountain Views, one house back from Kailua beach, 30 second walk down a sandy beach path. We are also just about a 5 mine drive to the famous Lanikai Beach. Escape to Kailua, a small beach town located just 20 minutes from Honolulu and Waikiki, truly away from it all! brbrOur home features high speed wireless internet, two flat screen tvs, Hawaiian koa wood cabinets, marble, and crown molding, modeled after the historic residence next door. There is a NEW window A/C unit in the master bedroom (it's the only bedroom that has ac as it doesn't face the ocean) and screens on all windows and fans throughout the house. brbrThere are two large lanais one upstairs (with ocean and mountain views) and one downstairs. Brand new deck as of October 2024. The house is situated on an acre of land with lush landscaping, allowing ample room to lay out in the Hawaiian sun or let the kids play. The yard has beautiful plumeria trees, red hibiscus bushes, orchids, and of course, a coconut grove. brbrThe house has one King bed, two queen beds and two twin beds. We also provide a pack n play if needed. It has two full bathrooms, one with a tub/shower combo the other with a walk in shower. The master bedroom (king bed and a twin) and one full bathroom are located upstairs where the kitchen, dining room and living room are. The other two bedrooms and second bathroom are located on the first floor. The second bedroom has a queen bed and the third bedroom has a queen and a twin. brbrThe kitchen is stocked with everything you need to cook. It has a full sized oven, four burner cooktop, refrigerator/freezer, microwave, dishwasher, toaster and coffee maker. The kitchen has four barstools, perfect for hanging out while meals are prepared or for casual breakfasts. The dining room table seats six and there is also an outdoor patio set complete with tables and chairs with an ocean view. New sectional couch in living room. brbrA full sized washer and dryer are located inside the house for your convenience as well.brbrWe have one security camera located outside to the left of the front door that monitors the driveway to ensure guest and property safety. brbr1990/NUC -1795brTax Map Key No. 430180450002brbrKeywords: House, Kailua, Lanikai, Beach, Watersports, View, Private, Ocean, Hawaii, Relax, Mountain, legal, sand, vacation, estate

Bed

Bath

Sleeps

$833.36

/ Nightly

Private Vacation Home

Lanikai Cottage: Charming Tropical Oasis w/Private Pool & A/C, Walk to Beach

Kailua, Hawaii, United States

Just steps from the turquoise shoreline of Lanikai Beach, Lanikai Cottage by Gather is a beach-chic 3-bedroom, 2-bath retreat with two separate dwellings on one property and a brand-new private pool. Ideal for families or couples traveling together, this island holiday home blends coastal charm with modern comforts in one of Oahu’s most beloved neighborhoods.brbrWhat You’ll Love About Lanikai Cottage by Gatherbr• Two private dwellings: main house with 2 bedrooms and 1 bath, plus guest studio with bath, kitchenette, and lanaibr• New pool & fenced backyard with sun loungers, covered seating, BBQ, and outdoor diningbr• Two-minute stroll to Lanikai Beach via Pokele Beach Accessbr• Adventure gear included: two kayaks, stand-up paddleboard, bikes, snorkel sets, and boogie boardsbr• Split A/C and high-speed Wi-Fi for easy, comfortable livingbrbrLiving & DiningbrThe main house welcomes you with bright, breezy interiors that open to the front lanai and the backyard. A comfortable lounge anchors the space for relaxed movie nights and post-beach downtime, while the adjacent dining area seats the crew for family meals or game night.brbrChef-Ready KitchenbrCook with ease in the well-equipped main-house kitchen featuring stainless appliances, ample counter space, and convenient flow to indoor dining and the outdoor grill. In the guest studio, a handy kitchenette supports light bites and morning coffee on the lanai.brbrOutdoor OasisbrLinger in the private, fenced backyard where the new in-ground pool glimmers beside swaying palms. Settle into loungers for lazy afternoons, gather beneath the covered seating area, and fire up the BBQ for al fresco dinners. Rinse, repeat, and wander back to the beach for sunrise or a golden-hour stroll.brbrSleeping Quartersbr• Primary Bedroom (Main House) – King bed, Split A/C, ceiling fan, shared bathbr• Guest Bedroom 2 (Main House) – Two twin beds, Split A/C, ceiling fan, shared bathbr• Guest Studio – King bed and sofa bed (sleeps 2 adults + 2 children or 3 adults), ensuite bath with tub/shower combo, kitchenette, living area with TV, Split A/C, ceiling fan, balcony with partial ocean viewbrbrExtrasbr1,469 sq ft of interior living across both dwellings, washer and dryer, flat-screen TVs, high-speed Wi-Fi, and complimentary adventure gear make this vacation rental as practical as it is inviting. It’s an effortless base for families, couples, and digital nomads alike.brbrNearbybrReach Lanikai Beach in minutes via Pokele Beach Access, or launch kayaks to the Mokulua Islets when conditions allow. Kailua Town is a short drive for cafés, boutiques, and Whole Foods. HNL is the nearest major airport for easy arrivals.brbrGood to Knowbr• This property is offered as a monthly rentalbr• The monthly rate applies in full regardless of number of nights stayedbr• Minimum 30-day booking period requiredbr• Standard occupancy 6 guests; max 8 with prior approval and additional feesbr• Online bookings subject to owner or manager approvalbr• Electric Security Deposit: $1,000; refundable after checkout if usage is within limitsbr• Electric allowance: $300 includedbr• Split A/C in main-house bedrooms and guest studiobr• Rates and fees are subject to change; minimum stay requirements may applybr• TAT ID: TA-111-603-0976-01br• TMK: 430040320000brbrReserve your dates at Lanikai Cottage by Gather and enjoy effortless days between the pool, the sand, and the laid-back charm of Kailua.

3

Bed

2

Bath

6

Sleeps

Vacation Home Rentals By Owner In Kailua, HI

$892.01

$545.75

$312.12

$290.84

$1597.23

$2633.63

$712.32

$494.64

$373.15

$959.39

$4253.84

$365.55

$1026.97

$1002.11

$592.57

$1412.63

$991.01

$833.36

Rent a place that suits your needs

Most popular vacation rentals in Kailua

$1597.23

$1243.99

$1270.98

$1279.74

$1354.55

$1403.34

$1412.63

$1466.09

$4288.97

$4253.84

Most Popular Cities in Hawaii