Search for vacation rentals in Kailua.

Whether it's vacation home rentals, apartments, condos, or cabins/cottages, we have you covered -- search for rental properties in the entire Kailua area to find the perfect spot for your vacay.

523 Iliaina St
	523 Iliaina St Kailua, HI $4,400 Vacation Rentals, Unknown  NEW! Comfortable and quiet home in desirable Kailua neighborhood near best beaches, convenient shopping, excellent schools, Kaneohe Bay, H-3 and Pali highways, and bus routes. Spacious house with 3 air......

1435 Auauki St
	1435 Auauki St Kailua, HI $4,300 Vacation Rentals, Unknown  NEW! Bright and welcoming 3-bedroom, 2.5 bath home in the beautiful neighborhood of Hillcrest, Kailua. Panoramic mountain, lake and ocean views with high vaulted ceiling and large, private swimming......

885 Akalei Pl
	885 Akalei Pl Kailua, HI $5,950 Vacation Rentals, Unknown  NEW! This beautiful lake front home is situated on a quiet cul de sac at the entrance to the lake with access to the lake and the canal which connects to the ocean. It has a newly renovated dock, great......

549 Kawainui St
	549 Kawainui St Kailua, HI $3,500 Vacation Rentals, Unknown  NEW! Gorgeous Hawaiian plantation-style home with a large fenced-in back yard. 2 bedrooms, a den, and a small loft! Yard has mature tropical fruit trees and lots of native plants/grass. Private parking......

73 Aalapapa Pl
	73 Aalapapa Pl Kailua, HI $5,000 Vacation Rentals, Unknown  NEW! With one of Oahu's best views, The Lanikai Luxury View home brings a breath of relaxation that keeps on giving. the hillside location makes for some very rewarding views. Be it the Beautiful,......

Paokano Pl
	Paokano Pl Kailua, HI $7,500 Vacation Rentals, Unknown  NEW! This renovated 3200 sq.ft. luxury executive home (4 bedrooms, 3 bathrooms) located in one of the most highly desired neighborhoods in Kailua sits in a very quiet, breezy, and quaint cul-de-sac on......

1060 Alahaki St
	1060 Alahaki St Kailua, HI $4,500 Vacation Rentals, Unknown  NEW! Beautifully remodeled 3bdr., 2bth. detached single family home in Enchanted Lake. All the bedrooms have split ACs and ceiling fans. The open kitchen area, with seating around the island, is perfect......

1366 Nanawale Pl
	1366 Nanawale Pl Kailua, HI $3,350 Vacation Rentals, Unknown DRIVE BY take a look at the neighborhood & location, if still interested EMAIL to schedule viewing. 3 bedroom / 2 bath single family house w/ carport - includes refer, range, DW, granite counters.......

1448 Auauki St
	1448 Auauki St Kailua, HI $5,950 Vacation Rentals, Unknown Brand new modern house in Enchanted Lake, quiet neighborhood in a cup-de-sac. 4 Bed 3 Bath 2 Garage parking...

610 Auwai St
	610 Auwai St Kailua, HI $4,500 Vacation Rentals, Unknown Available June 1. Beautiful property in wonderful coconut grove neighborhood. 3/2 and two car garage. Split A/C in every room. Outdoor shower and surf racks. Landlord pays internet, tenant pays......

551 Olomana St
	551 Olomana St Kailua, HI $4,300 Vacation Rentals, Unknown This single family home is ready to move in on 5/7/2024. This is a 3 bedroom/ 2 bathroom home down a col-da-sac in the heart of Kailua just blocks from the beach, shopping and MCBH-Kaneohe! This......

701 Kihapai St
	701 Kihapai St Kailua, HI $5,400 Vacation Rentals, Unknown Step into comfort with this well-maintained, single-level family home nestled in the heart of Kailua. Boasting a spacious 1,554 sqft of living space, this property features 3 bedrooms and 2......

Kihapai St
	Kihapai St Kailua, HI $4,100 Vacation Rentals, Unknown Kailua 3 bedrooms/2 baths home available after June1, 2024. Utilities, wifi, laundry included in rent. 2 carport parking spaces on premise and gated yard. Laundry unit is shared with other tenants......

14 Aulike St #401
	14 Aulike St #401 Kailua, HI $2,550 Vacation Rentals, Unknown Fully furnished two bedroom condo in the middle of Kailua Town! Don't miss your chance to rent this remodeled 2 bedroom / 1.5 bathroom unit in Meridian East. Upgraded bathrooms, new paint. Laundry......

1005 Keolu Dr
	1005 Keolu Dr Kailua, HI $2,900 Vacation Rentals, Unknown New 2BR/1BA unfurnished home with small yard in Enchanted Lake. All new appliances and tiled floors. Vinyl fencing ensures privacy. Quiet neighborhood, Shared driveway (one assigned parking space).......

612 Ulumalu St
	612 Ulumalu St Kailua, HI $3,900 Vacation Rentals, Unknown Available on May 13th, 2024. This is a recently renovated 3 bedroom and 1.5 bathroom house with luxury vinyl plank floors and quartz kitchen countertops. Located in a peaceful Kailua location and......

327 Manae St
	327 Manae St Kailua, HI $4,500 Vacation Rentals, Unknown Available APPROXIMATELY May 1, 2024 This property is UNFURNISHED. Perfect Location for Oahu living! Walk to world famous Kailua and Lanikai Beaches, walk to Kailua town, and have an easy,......

596 Iana St
	596 Iana St Kailua, HI $7,995 Vacation Rentals, Unknown Welcome to this renovated home on the water with a sparkling pool! The Chef's kitchen has plenty of cabinet space, modern appliances, quartz countertops and a huge eat in bar! The open concept......

916 Maluniu Ave
	916 Maluniu Ave Kailua, HI $2,800 Vacation Rentals, Unknown Available now with showings by appointment only starting Saturday April 13. Please message via Zillow to schedule. Beautiful, newly-built & spacious accessory dwelling unit (ADU) with a private......

1024 Hoolea Pl
	1024 Hoolea Pl Kailua, HI $3,000 Vacation Rentals, Unknown Furnished 2 bedroom/1 bathroom with open air living space for cool Hawaii nights! This property is in a quiet circle with 1 other home. Gas stove top, oven, refrigerator, full bathroom with tub,......

288 Kahako St
	288 Kahako St Kailua, HI $5,400 Vacation Rentals, Unknown Private 2,090 sq ft unfurnished 4-bedroom, 2.5-bath house located in a quiet neighborhood of Keolu Hills, Kailua, tucked right off of Kalanianaole Highway. Boasting views of Mount Olomana, this......

726B Kalolina Pl
	726B Kalolina Pl Kailua, HI $1,500 Vacation Rentals, Unknown Private room and bathroom with separate entrance from the house. Large glass sliding security door outlooking the Koolau mountains....

Kaipii St
	Kaipii St Kailua, HI $1,950 Vacation Rentals, Unknown Imagine coming home to your spacious room that includes an attached renovated bathroom, private patio to read or relax and amenities including a refrigerator/freezer, microwave, k-cup maker, A/C,......

202 S Kalaheo Ave
	202 S Kalaheo Ave Kailua, HI $4,000 Vacation Rentals, Unknown Welcome to Avendaro, "The Dream Place", a historic 1921 Hawaiian Plantation style home. Our private beach path leads to uncrowded Kailua beach and is noted for its soft white sand, ideal for......

116 Kuulei Rd
	116 Kuulei Rd Kailua, HI $2,975 Vacation Rentals, Unknown Avail May 1st, Air conditioned, Fully furnished, private and comfortable, 3 mins walk to Kailua Beach, washer and dryer, storage, Please no Dogs. Open to flexible lease options. Minimum 3 months....

365 Kalama St
	365 Kalama St Kailua, HI $4,500 Vacation Rentals, Unknown Beautiful, spacious, 3 Bdr / 3 Ba Kailua main home with central A/C, down the street from Kailua's world famous sandy beaches, shops, restaurants and more. Live your best life in this highly sought......

1361 Aupapaohe St
	1361 Aupapaohe St Kailua, HI (Contact seller for price) Vacation Rentals, Unknown Discover a captivating 3-story single-family residence nestled in the charming Hillcrest neighborhood of Kailua. The home offers a unique kitchen with a sub-zero refrigerator, gas range, double......

151 Hauoli St
	151 Hauoli St Kailua, HI $5,500 Vacation Rentals, Unknown This quaint Beach home, tucked away down a private flag lot, is steps away to beautiful Kailua beach and Kalama beach park. The house boasts some very nice features such as hard wood and tile......

649A Oneawa St
	649A Oneawa St Kailua, HI $1,900 Vacation Rentals, Unknown Location: The unit is conveniently situated just a 2-minute drive away from both Kailua Town, the H-3, and the beach. 5 minutes from the MCBH back gate. Military personnel are welcomed! Parking:......

S Kalaheo Ave
	S Kalaheo Ave Kailua, HI $6,500 Vacation Rentals, Unknown Beachside property steps to beautiful Kailua beach - 5 miles of white sand beach right outside your back gate. True island living, with established tropical landscaping and gated enclosed back......

402 Hualani St
	402 Hualani St Kailua, HI $4,800 Vacation Rentals, Unknown Open House: Saturday, April 6, 10am - 12pm. Please be respectful of neighbors when parking along the street. 3 bedroom 2 bath home with fenced yard in Coconut Grove area; 5-minute walk to beach and......

158A Makawao St
	158A Makawao St Kailua, HI $4,200 Vacation Rentals, Unknown Great Location! Less than 2 blocks to world famous Kailua Beach and short walk/bike ride to Kailua Town. No one below you or above you. Available June 25, 2024. $4,200 rent includes 1 small pet.......

101 N Kainalu Dr
	101 N Kainalu Dr Kailua, HI $5,500 Vacation Rentals, Unknown This home is a special gem down a quaint private side lane and located just one large block from Kailua Beach. Walking distance (10 mins) to downtown Kailua which includes; schools, dining, Whole......

249 N Kainalu Dr
	249 N Kainalu Dr Kailua, HI $6,995 Vacation Rentals, Unknown Welcome to this beautifully fully furnished 3 bdrm 2 bath plantation style home with a large covered lanai and pool! This gated property is enclosed by a gorgeous rock wall and tropical......

1194B Kamahele St
	1194B Kamahele St Kailua, HI $4,500 Vacation Rentals, Unknown Rarely available 3 bedroom/2.5 bathroom tri-level town-home, completely upgraded in exclusive Bluestone. Mohagany wood and Quarts touches. All newer appliances in Chef's kitchen. Master suite on......

891 Kainui Dr
	891 Kainui Dr Kailua, HI $4,350 Vacation Rentals, Unknown KEY FEATURES Year Built: 2019 Sq. Footage: 1366 Sq. Ft. + 200 Sq Ft. covered Lanai Bedrooms: 3 Bathrooms: 2.5 Parking: 2 car enclosed Garage 420 Sq Ft Lease Duration: 1 Year Security Deposit:......

616 Maluniu Ave
	616 Maluniu Ave Kailua, HI $6,000 Vacation Rentals, Unknown Charming, tropical and creative fully furnished cottage near Kailua Beach. Single story, two bedroom and two bath. Located down a private lane. Includes living room, kitchen, office, covered lanai......

420A Oneawa St
	420A Oneawa St Kailua, HI $4,000 Vacation Rentals, Unknown For any questions or to schedule a showing please email us your availability. AVAILABLE NOW -- HI Roots realty presents this breezy 3 BR, 2 BA, with 2-car carport parking detached single family......

1132 Akumu St
	1132 Akumu St Kailua, HI $3,500 Vacation Rentals, Unknown Quaint Kailua! Entire 2 bedroom guesthouse on 2nd story (no home below) with gorgeous mountain and lake views. Minutes to everything Kailua has to offer. Near 4 of the country's best beaches, 5......

861 Aalapapa Dr
	861 Aalapapa Dr Kailua, HI $9,000 Vacation Rentals, Unknown Mid-century modern beach house in Lanikai, Oahu's most coveted beach community! Views of the ocean, mountains, and Mokulua Islands. Conveniently situated just a short stroll from beach, the main......