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.

617 Wailepo St #G
	617 Wailepo St #G Kailua, HI $2,100 Vacation Rentals, Unknown  NEW! Available now! Charming 2 bed, 1 bath renovated unit in Kailua, located in walking distance to a variety of eateries and shopping. This unit is located on the 2nd floor (walk up) and comes with a......

401M Keolu Dr
	401M Keolu Dr Kailua, HI $4,900 Vacation Rentals, Unknown  NEW! 1 st Floor House Attatched; 4BR / 2Ba 2200ft2 House 401 Keolu Dr. House Beautiful 4 Bed 2 bath Excellent Condition Built in; (2015/2016) Big Open flowing floor plan partly furnished Kailua......

930 Kainui Dr
	930 Kainui Dr Kailua, HI $6,000 Vacation Rentals, Unknown  NEW! End your Kailua rental search here. This long-term unfurnished rental offers 4 bedrooms and 2 bathrooms on desirable Kainui Drive (affectionately known as "Duck Lane"). The home boasts an open......

68 Laiki Pl
	68 Laiki Pl Kailua, HI $11 Vacation Rentals, Unknown  NEW! Gorgeous home with gated beach access just 50 yards away. This property is located beachside on a wide, family friendly and quiet dead end street near everything Kailua has to offer. Built in 2016......

1304 Kika St
	1304 Kika St Kailua, HI $3,850 Vacation Rentals, Unknown Highly desirable 4 bdr/2.5 bth home in Kailua. Upgraded home with quartz countertops, new carpet, new vinyl flooring, new fixtures, and newly painted throughout. Nice open layout with a spacious......

330 Lapa Pl
	330 Lapa Pl Kailua, HI $4,200 Vacation Rentals, Unknown Gorgeous views with an ocean breeze! This Lanikai 3 bedroom, 1 bathroom has lots of storage. Private 500 sq. ft. lanai with additional outdoor lanai and storage below for surf boards and bikes.......

335 Oneawa St
	335 Oneawa St Kailua, HI $4,000 Vacation Rentals, Unknown Meticulously maintained 3-bedroom, 2.5-bathroom home with a bonus room, 1-car carport, and gated yard. The house offers a full kitchen, washer & dryer, and split air conditioning. Great location......

450A Hualani St
	450A Hualani St Kailua, HI $5,100 Vacation Rentals, Unknown Single family home with private, fenced in yard. Located on a quiet lane, walking distance to the beach, Whole Foods, Target, restaurants, etc. Easy access to H3 or the Pali. (Also the neighbors......

70 Wilikoki Pl
	70 Wilikoki Pl Kailua, HI $3,650 Vacation Rentals, Unknown Available July 1st 2024 Furnished or Unfurnished $3,650/Month (Includes Taxes/Utilities/Yard Service/ Internet) - 6 Month Minimum New - Completely Remodeled Beachside Cottage This rental is a......

461H Kawailoa Rd
	461H Kawailoa Rd Kailua, HI $6,350 Vacation Rentals, Unknown Exemplifying the essence of a Hawaiian beach abode, this meticulously adorned and fully-equipped turn-key home boasts a contemporary aesthetic with pristine furnishings. Nestled in an ideal spot......

936 Mokapu Blvd #A
	936 Mokapu Blvd #A Kailua, HI $2,000 Vacation Rentals, Unknown Available for immediate occupancy! FOR SHOWINGS, TEXT ONLY: Mari Eagar [R] #RB-23597 Upgraded Studio/1ba/ample street parking triplex unit in the Kailua area is walking distance to Kailua beach......

122 Pukoa St
	122 Pukoa St Kailua, HI $3,750 Vacation Rentals, Unknown One block to the beach. Hardwood floors; two off street parking one covered; large deck; yard; storage; 3 bed 2 bath unit available July 1....

110 Kuulei Rd
	110 Kuulei Rd Kailua, HI $4,950 Vacation Rentals, Unknown Fully Furnished 2br 2 bath with an office. Amazing location. Just a 3 min walk to Kailua Beach and 15 min walk to Whole Foods. Recently renovated with a mix of travertine tile flooring and water......

332 Kuukama St
	332 Kuukama St Kailua, HI $7,500 Vacation Rentals, Unknown Discover the perfect blend of comfort and convenience at this charming one-level single-family home located at 332 Kuukama St, Kailua. Boasting five spacious bedrooms and three well-appointed......

461H Kawailoa Rd
	461H Kawailoa Rd Kailua, HI $6,350 Vacation Rentals, Unknown Exemplifying the essence of a Hawaiian beach abode, this meticulously adorned and fully equipped home boasts a contemporary aesthetic with pristine furnishings. Nestled in an ideal spot just before......

418 Ulupaina St
	418 Ulupaina St Kailua, HI $4,350 Vacation Rentals, Unknown Attached home with exclusive large gated backyard. This 3 bedroom home with Bonus Room, perfect for office or home schooling. The property is located about 5 minutes from the Kaneohe Marine base,......

Uluniu St
	Uluniu St Kailua, HI $2,200 Vacation Rentals, Unknown Large studio with full kitchen centrally located in Kailua town (walking distance to Kailua Beach) $2200 monthly Utilities included (electric & water) 6 month lease, security deposit equivalent......

205 Kailua Rd
	205 Kailua Rd Kailua, HI $6,800 Vacation Rentals, Unknown This plantation style 3 bedroom, 3 bath home is just one block to Kailua Beach and available unfurnished. The property offers a fully fenced yard and a large detached two car garage, with an......

1066 Koohoo Pl
	1066 Koohoo Pl Kailua, HI $2,400 Vacation Rentals, Unknown TITLE: 1 Bed/1 Bath Lanikai Cottage RENTAL TERMS: Rent: $2400 + 4.712% GET Tax = $2,513.09 Non-Refundable Rental Application Fee: $45 (Only one applicant needed per household) Security Deposit:......

354A Keolu Dr
	354A Keolu Dr Kailua, HI $2,850 Vacation Rentals, Unknown **NEWLY RENOVATED** **AVAILABLE JUNE 1ST** Enchanted Lake large 1 bedroom apartment with FULL kitchen, all new appliances. Private, spacious, very breezy and cool, with mountain views, and a lot of......

354B Keolu Dr
	354B Keolu Dr Kailua, HI $2,550 Vacation Rentals, Unknown **Available July 1st** Spacious updated semi-furnished Kailua / Enchanted Lake studio with large, beautiful quartz counter top and stainless steel appliance gourmet full kitchen. The place really......

1319 Mokolea Dr
	1319 Mokolea Dr Kailua, HI $6,000 Vacation Rentals, Unknown Spacious FURNISHED 2Bedroom/1Bath plus Lanai in desirable and secluded Lanikai. Boho styled furnished home in the desirable Lanikai neighborhood with panoramic views of the ocean & the splendor of......

431A Kalama St
	431A Kalama St Kailua, HI $3,500 Vacation Rentals, Unknown Charming 2 bedroom, 1 bath 1,100 square foot house in the heart of Coconut Grove area of Kailua. The home features a full kitchen with a dishwasher, washer and dryer, outdoor shower, light and airy......

452 Dune Cir
	452 Dune Cir Kailua, HI $2,500 Vacation Rentals, Unknown Welcome to Dune Circle! This renovated one bedroom, one bath unit is located in the highly desirable Beachside neighborhood of Kailua. One bedroom, one bath unit with large storage space. New vinyl......

1445 Auwaiku St
	1445 Auwaiku St Kailua, HI $6,000 Vacation Rentals, Unknown Paradise Awaits: 4 Bedroom Kailua Home with Pool and Ocean Views Immerse yourself in island living in this captivating 4-bedroom, 2-bathroom home in Kailua. Enjoy stunning ocean views, a refreshing......

933 Kaipii St
	933 Kaipii St Kailua, HI $1,850 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,......

347 Hualani St
	347 Hualani St Kailua, HI $1,950 Vacation Rentals, Unknown 1 Parking Stall is included with this spacious 1 bedroom 1 bathroom rental space. A shared washer/dryer downstairs on the property. This is a non-smoking, No-pet, 1 Year lease only. Showings are......

1508 Aalapapa Dr
	1508 Aalapapa Dr Kailua, HI $4,600 Vacation Rentals, Unknown Island style living, walking to beach access is 5 minutes away. Kayak, swim or just enjoy the beauty of this tranquil beach in Lanikai. Beautiful open specious yard ....

737 Maluniu Ave
	737 Maluniu Ave Kailua, HI $3,250 Vacation Rentals, Unknown Adorable beach cottage 3 blocks from world famous Kailua Beach, minutes to town, MCBH and H3. 3 bed/1 bath, open living/dining/kitchen, huge fenced yard, quiet Kailua neighborhood. Elevated above......

345B Kalama St
	345B Kalama St Kailua, HI $5,000 Vacation Rentals, Unknown Embrace Island Living in this Upgraded Kailua Oasis Everything you need to fully embrace Kailua (96734). Island style living is at your fingertips, nestled within the welcoming and sought after,......

1435 Akiikii Pl
	1435 Akiikii Pl Kailua, HI $1,800 Vacation Rentals, Unknown Great Kailua Enchanted Lake neighborhood 1/1. Unit includes kitchenette with a microwave and hot plate. There is no washer and dryer available on the property and one off-street parking for a small......

613 Oneawa St
	613 Oneawa St Kailua, HI $3,300 Vacation Rentals, Unknown Description, *613 Oneawa St* Charming Clean Single family Renovated Three bedroom one bathroom. Home has secured chain link , gates and CMU fenced yard wall, and is Partly furnished with New 30"......

515 Ilimano St
	515 Ilimano St Kailua, HI $5,050 Vacation Rentals, Unknown Welcome to your slice of paradise at 515 Ilimano Street in the serene coastal town of Kailua, Hawaii. Just 2 miles away from the world-renowned Kailua Beach, this exquisite rental property offers......

1308 Kuuna St
	1308 Kuuna St Kailua, HI $3,980 Vacation Rentals, Unknown Desirable 3 bdr/2.5 bth home featuring a spacious living room, dining area, and huge covered lanai. Remodeled kitchen with upgraded countertops, cabinets, and appliances. Updated bathrooms and wood......

633 Hanale Pl
	633 Hanale Pl Kailua, HI $5,950 Vacation Rentals, Unknown Excellent condition home in a well-maintained and quiet 16 home cul-de-sac neighborhood consisting of retired and professional families. A couple of minutes out of Kailua town with access to......

333 Wanaao Rd
	333 Wanaao Rd Kailua, HI $6,750 Vacation Rentals, Unknown Kailua furnished home with a pool and private gated yard. Available July 1, 2024. 3-6 month lease available. 3 bedroom/ 2 bathroom, All appliances and washer/dryer included. Split A/C units in each......

669 Kihapai St
	669 Kihapai St Kailua, HI $4,400 Vacation Rentals, Unknown "This lovely property is situated in a quiet area just a short walk away from the beach, making it an ideal location for anyone who loves the ocean. With three spacious bedrooms and two bathrooms,......

748 Oneawa St
	748 Oneawa St Kailua, HI $3,600 Vacation Rentals, Unknown 3 bedroom 1 bath home located in the Coconut Grove area of Kailua. Excellent schools. Walking distance to Kailua beach and Kaha park (marsh path). Close to H3, and KMCB, Kailua recreation center......

346 Ilimalia Loop
	346 Ilimalia Loop Kailua, HI $6,000 Vacation Rentals, Unknown Please note lease must end no later than 12/31/2024. Recently remodeled four-bedroom, two-bathroom home backs to a canal and offers laminate flooring throughout, large kitchen with stainless steel......

1271 Auwaiku St
	1271 Auwaiku St Kailua, HI $5,500 Vacation Rentals, Unknown Welcome home! Spacious 3 bed, 2 bath Kailua home with a great open floor plan! Inside you'll find vaulted ceilings, an open kitchen with walk in pantry, large dining with breakfast bar, and a......