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.

3 Puukani Pl
	3 Puukani Pl Kailua, HI $23 Vacation Rentals, Unknown  NEW! Brand New Remodeled Home, available starting Feb 1, 2025. Photos are prior to remodel, all new chefs kitchen and 5 star bathrooms, Exclusive private 8 home community on a private lane, Steps to......

1129 Koohoo Pl
	1129 Koohoo Pl Kailua, HI $139 Vacation Rentals, Unknown  NEW! A serene haven where heaven meets the ocean. This elegant and contemporary home boasts 2 bedrooms and 2 bathrooms. Offering stunning panoramic views of the ocean and Mokulua Islands, this......

318A Manono St
	318A Manono St Kailua, HI $4,100 Vacation Rentals, Unknown  NEW! COMING SOON AVAILABLE JULY 1st. Welcome home to this Newly remodeled 3 bedroom 2 bathroom beach house duplex. Nestled down a Private Lane, this house is just 2 short blocks to Famous Kailua/Kalama......

244 Kihapai St
	244 Kihapai St Kailua, HI $3,850 Vacation Rentals, Unknown  NEW! 3BR/2 BA single family home in excellent condition with huge fenced-in yard and terrific sunset views. Close to everything. Walk to Kailua town and Kawainui Trail, bike to Kalama and Kailua Beach......

572 Keolu Dr
	572 Keolu Dr Kailua, HI $6,500 Vacation Rentals, Unknown FOR RENT Welcome home to this extra spacious 4 bed/3 bath single-level home. Over 2700 sq ft! $6500/month. Laundry room with Washer/Dryer in unit, multiple living areas, high ceiling, outdoor......

521 Kawailoa Rd
	521 Kawailoa Rd Kailua, HI $15 Vacation Rentals, Unknown Exclusive gated community. Steps to Kailua Beach. Air Conditoned. Heated Pool. This home is rented on a seasonal basis and has a seven night minimum stay. Contact the owner for additional details......

1123 Puwa Pl #303
	1123 Puwa Pl #303 Kailua, HI $3,600 Vacation Rentals, Unknown Available now! 1048 sqft 2 bed, 1.5 bath pet-friendly townhome at Aikahi Gardens in beautiful Kailua. This unit offers a spacious, functional layout, upgraded interior, full kitchen with ample......

228 Mookua St
	228 Mookua St Kailua, HI $4,820 Vacation Rentals, Unknown Cozy, clean, gated and safe Hawaiian style home in great location close to famous Kalama Beach, 3 min away from Kailua/Lanikai beach. 3 bedrooms accommodate 6 people, additional sofa bed in the......

316 Manae St
	316 Manae St Kailua, HI $3,695 Vacation Rentals, Unknown Recently renovated 4/2 1344 sq.ft downstairs unit in a Kailua duplex house. New kitchen, new bathroom, appliances, and flooring. Separate entrances and unit has own washer and dryer. Small garden......

1447 Humuula St
	1447 Humuula St Kailua, HI $2,995 Vacation Rentals, Unknown Available Date: 6/3/24 Amazing 3 bedroom, 1 bathroom house in Enchanted Lake neighborhood. 3 car park carport, more parking available on street in front of house. Renovated bathroom, new flooring,......

568D Kawailoa Rd
	568D Kawailoa Rd Kailua, HI $9,750 Vacation Rentals, Unknown Beautiful, 4 bedroom, 4 bath modern home only three houses from the beach in Kailua, on the edge of Lanikai. Living room, family room, wet bar, enclosed garage. Close to restaurants, shopping,......

1214 Kupau St
	1214 Kupau St Kailua, HI $4,200 Vacation Rentals, Unknown Available July 1st 2024. Located on the top of Kupau Street, this is a family centered home with laminate floors, updated kitchen, bath, and large covered outdoor patio area for dining and......

716 Keolu Dr
	716 Keolu Dr Kailua, HI $5,100 Vacation Rentals, Unknown Welcome to this charming home perfect for your time here on O'ahu in the highly desirable and family friendly Enchanted Lake neighborhood! You will enjoy this safe neighborhood and picturesque......

305 Ulupaina St
	305 Ulupaina St Kailua, HI $3,800 Vacation Rentals, Unknown 4 Bedroom 2 full bath, 3 car parking fenced in yard, split AC in living area. Freshly painted, new flooring centrally located in Kailua Town. 1 year lease offered (no extensions at this point) No......

1209 Mokapu Blvd
	1209 Mokapu Blvd Kailua, HI $5,800 Vacation Rentals, Unknown Be the first to rent this fantastic Kailua home! Available starting June 15th, this conveniently located home, has a large living area, with open concept kitchen and high-end stainless steel......

503 Kawailoa Rd
	503 Kawailoa Rd Kailua, HI $7,995 Vacation Rentals, Unknown Practically Beachfront, Dolphin Manor is an amazing house and will be the perfect place for you to relax and live the Hawaiian lifestyle. It is a spacious 3 bedroom, 4 bath home located less than a......

451 Aulima Loop
	451 Aulima Loop Kailua, HI $6,950 Vacation Rentals, Unknown Rare find on quiet, coveted Aulima Loop! Wonderful, light-filled single family home in quiet neighborhood, walking distance to a top Hawaii school (Ka'elepulu Elementary). Five-minute drive to......

1181 Lauloa St
	1181 Lauloa St Kailua, HI $3,000 Vacation Rentals, Unknown Available now! This is a spacious unit with 2 bedrooms and 1 bathroom in a very quiet Neighborhood. This home features an open kitchen with stainless steel appliances, plenty of storage space and a......

1238 Keolu Dr
	1238 Keolu Dr Kailua, HI $7,900 Vacation Rentals, Unknown This Is A Fully Furnished Rental Wifi Included TV With Amazon Prime Video Washer & Dryer Free Parking On Premises Keep it simple at this peaceful and centrally-located place. This modern home just......

340 Ilihau St
	340 Ilihau St Kailua, HI $3,500 Vacation Rentals, Unknown $3500 / month. 2 Bed / 1 Bath. Ocean View, Split A/C, 2x Parking, Lots of Storage. Available now. Wake up to a breathtaking view of Kailua Bay and Lanikai Point in this sunny, newly renovated two......

617 Wailepo St #G
	617 Wailepo St #G Kailua, HI $2,100 Vacation Rentals, Unknown 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 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 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 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......