Vacation Rentals in Kailua, HI

481 available vacation rental offers

7 nights
2
1
  • airbnb
  • booking
  • stayz
  • expedia
  • hotelscom
  • tripadvisor
  • tripcom
  • agoda
  • homestay
  • tuivillas
  • hostelworld
  • hotelopia
Kailua, HI holiday rentals
Choose the perfect holiday accommodation
Price per night
Accommodation type
Rating

481 Holiday rentals and Airbnb in Kailua, HI

Highly-Rated Holiday Rentals for Families in Kailua, HI

Give the kids instant backyard beach fun and plenty of room to unwind at spacious family holiday rentals in Kailua, HI.

Newly Innovated Oceanview Beach Condo - Sauna Pool - Kailua, HI
No reviews

Newly Innovated Oceanview Beach Condo - Sauna Pool

apartment, Urban Honolulu
This Waikiki apartment, a short walk from Waikiki Beach and near Kapiolani Park, offers easy access to attractions such as the US Army Museum of Hawaii (approximately 1.6km away).
The 125 square metre self-catering flat, sleeping up to seven guests, features a private balcony with sea views, a well-equipped kitchen, and access to the Pacific Monarch Hotel's swimming pool, garden, and sun terrace; free Wi-Fi is provided.
Waikiki Banyan Ocean View Remodeled - "Ohana Suite" , Free Parking, Lots Of Amenities! - Kailua, HI
9.8 114 reviews

Waikiki Banyan Ocean View Remodeled - "Ohana Suite" , Free Parking, Lots Of Amenities!

apartment, Urban Honolulu
This Waikiki apartment, situated in Tower 1 of the Waikiki Banyan, is located just 0.16 km from Waikiki Beach and Honolulu Zoo, offering easy access to Kalakaua Avenue and other attractions.
The 56 square metre flat features one bedroom, one bathroom, two queen beds and a queen-size sofa bed, sleeping up to six, and includes a fully equipped kitchen, free parking, and access to a heated pool, spas, and beach gear.
King Bed/renovated/canal& Mountain View/walk Beach - Kailua, HI
9.6 64 reviews

King Bed/renovated/canal& Mountain View/walk Beach

apartment, Urban Honolulu
This Waikiki studio apartment, situated in the Hawaiian Monarch building, is conveniently located near Ala Moana Center and 0.8 kilometres from Kahanamoku Beach, offering easy access to downtown Waikiki and other attractions.
The 22-square-metre self-catering unit sleeps two guests, featuring a split king bed (convertible to two twin XLs) and an ottoman bed, plus a swimming pool, jacuzzi and parking (charges apply), alongside building amenities.
Great Resort Living In A Luxury 2 Bed Corner Unit In Waikiki - Kailua, HI
10 3 reviews

Great Resort Living In A Luxury 2 Bed Corner Unit In Waikiki

apartment, Urban Honolulu
This Waikiki apartment, offered as 'Great Resort Living In A Luxury 2 Bed Corner Unit In Waikiki', is conveniently located within a 2.4km walk of the Hawaii Convention Centre, Waikiki Beach Walk, and Ala Moana Centre, with Royal Hawaiian Centre and International Market Place also nearby.
The 113 square metre, two-bedroom, two-bathroom condo sleeps four and boasts a fully equipped kitchen, in-unit laundry, a swimming pool, fitness centre, tennis court, and concierge service.

Find the Best Holiday Rentals with a Swimming Pool in Kailua, HI

Walk right out of your kitchen and jump into a crystal-clear swimming pool at island holiday rentals in Kailua, HI.

Free Parking, Ocean Views, High Floor - Kailua, HI
9.9 65 reviews

Free Parking, Ocean Views, High Floor

apartment, Urban Honolulu
This studio flat is situated in the Waikiki district of Urban Honolulu, offering excellent access to world-class beaches such as Waikiki Beach, which is less than 500 meters away, as well as shops and restaurants.
This apartment provides accommodation for two guests and features a fully equipped kitchen with a fridge, freezer, and microwave, air conditioning, complimentary Wi-Fi, and access to a communal swimming pool and on-site laundry facilities, with included parking for added convenience.
Luana 502 -Breathtaking Waikiki Studio Sleeps 4 - Kailua, HI
9.4 19 reviews

Luana 502 -Breathtaking Waikiki Studio Sleeps 4

apartment, Urban Honolulu
This studio flat is located in the nightly rental zone of Waikiki, a mere 100 metres from the famous Waikiki Beach, offering immediate access to numerous restaurants and shops.
This well-appointed flat accommodates up to four guests with two double beds, featuring a kitchenette with a fridge and microwave, air conditioning, complimentary high-speed internet, a private balcony with views, and access to a communal swimming pool, fitness centre, and parking.
Ocean View Waikiki Studio, Private Lanai, King - Kailua, HI
9.9 74 reviews

Ocean View Waikiki Studio, Private Lanai, King

apartment, Urban Honolulu
This Waikiki studio apartment is located minutes from Waikiki Beach and upscale shopping and dining, offering easy access to Honolulu's attractions.
The newly remodelled, luxurious studio sleeps three, features a king-size bed and a twin sleeper sofa, a fully equipped kitchen, and access to a swimming pool, jacuzzi, and BBQ grills; a pack 'n play crib is available on request.
Aloha Living At Waikiki Lanais - Kailua, HI
No reviews

Aloha Living At Waikiki Lanais

apartment, Urban Honolulu
This Waikiki condo is situated a six-minute walk from Kuhio Beach, close to Saint Augustine by the Sea church, the Royal Hawaiian Shopping Center, and the Royal Hawaiian Theater Legends in Concert Waikiki, approximately 16 kilometres from Honolulu International Airport.
This self-catering apartment offers 558 square metres of space, comprising one bedroom, one bathroom, and a living room, accommodating up to seven guests and including a fully equipped kitchen, swimming pool, jacuzzi, sauna, parking, and free Wi-Fi.

Frequently asked questions about holiday rentals in Kailua, HI

  • What should a first-time visitor not miss in Kailua, HI?

    The iconic Kailua Beach is a must-visit, known for its soft white sand and calm turquoise waters. You can't go wrong with a stroll along the beach, or even try out some paddleboarding or kayaking. And if you're feeling adventurous, you can take a hike up to the top of the nearby Lanikai Pillbox for stunning views of the coastline.
  • What are the best Airbnb and holiday rentals in Kailua, HI?

  • Which neighborhood in Kailua, HI should you consider for a vacation rental?

    Kailua town is a great choice, offering a mix of restaurants, shops, and cafes within walking distance of the beach. If you're looking for something quieter, consider renting in the Lanikai area, which is known for its beautiful beaches and more relaxed atmosphere.
  • What are the most popular Airbnbs in Kailua, HI?

  • What are the top family-friendly attractions in Kailua, HI?

    The Kailua Beach Park is a great spot for families, with a playground, picnic tables, and restrooms. The nearby Kailua Town is also a fun place to wander around with kids, with shops and restaurants. For a more adventurous outing, take a trip to the Ho'omaluhia Botanical Garden, which is a beautiful park with walking trails and a variety of plants and flowers.
  • What are the best holiday rentals with a pool in Kailua, HI?

  • When is the best time to book a vacation rental in Kailua, HI?

    The best time to book a vacation rental in Kailua is during the shoulder seasons, from April to May and September to October. You'll find fewer crowds and more affordable prices during these months, although the weather is still pleasant.
  • What are the best rentals for families and kids in Kailua, HI?

  • What are the best budget-friendly activities in Kailua, HI?

    Kailua Beach is free to access and a fantastic way to spend the day. The Kailua Town Farmers Market is also free to attend, and you can enjoy the atmosphere, browse the stalls, and even grab a bite to eat. For a scenic hike, check out the Lanikai Pillbox Trail, which offers stunning views of the coastline and is free to access.
  • What are the best rentals or Airbnbs with a jacuzzi in Kailua, HI?

  • What are the best restaurants with local dishes in Kailua, HI?

    For authentic Hawaiian cuisine, try the Kailua Fish Market for fresh seafood. The Buzz's Steak House is a local favourite, known for its juicy steaks and laid-back atmosphere. If you're looking for something a little more casual, try the Kailua Beachside Grill for classic Hawaiian dishes and stunning ocean views.
  • What are the best walking or cycling routes in Kailua, HI?

    The Kailua Beach Path is a popular walking and cycling route that stretches along the coastline for several kilometres. For a more challenging ride, try the Kualoa Ranch Loop, which takes you through scenic countryside and offers stunning views of the mountains.
  • Are there pet-friendly attractions in Kailua, HI?

    Kailua Beach Park welcomes dogs on leash, making it a great spot to enjoy the beach with your furry friend. The Kailua Town Farmers Market is also pet-friendly, so you can bring your dog along to browse the stalls and enjoy the atmosphere.
  • What are the benefits of choosing a vacation rental in Kailua, HI?

    Vacation rentals offer more space and privacy than hotels, often with full kitchens and living areas. They can also be more affordable, especially for families or groups. Many rentals also have unique features, such as ocean views or private pools.
  • What are the top sports attractions and facilities in Kailua, HI?

    Kailua Beach is a popular spot for swimming, surfing, paddleboarding, and kayaking. The nearby Kailua Bay is also a great place to go sailing or windsurfing. For a more organised activity, you can check out the Kailua Canoe Club, which offers lessons and races.

Popular destinations

Find Holiday Rentals with Balconies in Kailua, HI

Wake up to the soothing sight of the blue horizon right from your private rental balcony in Kailua, HI.

Aqua Aloha Surf Waikiki 410 | Sparkling City Views  Pool & Bbq - Kailua, HI
8.5 11 reviews

Aqua Aloha Surf Waikiki 410 | Sparkling City Views Pool & Bbq

apartment, Urban Honolulu
This Waikiki condo is a short walk (less than 1 km) from Waikiki Beach and International Market Place, with Royal Hawaiian Center and Waikiki Beach Walk also within a 1.5 km radius.
The 31-square-metre apartment sleeps two, features a balcony, a fully equipped kitchen including a microwave and fridge, a washing machine, and access to a swimming pool, barbecue grills, and a water park.
Serene Ala Wai Palms 2-bedroom | Newly Renovated - Kailua, HI
No reviews

Serene Ala Wai Palms 2-bedroom | Newly Renovated

apartment, Urban Honolulu
This two-bedroom flat offers a prime location in Waikiki, Honolulu, within a short walk to the Royal Hawaiian Shopping Centre, International Market Place, and Waikiki Beach, with spectacular views of the Ala Wai Canal.
This 97 square metre residence, accommodating up to four guests, features two ensuite bathrooms, a remodelled kitchen with a breakfast bar, air conditioning, a balcony, and access to a communal swimming pool and allocated parking.
Aqua Aloha Surf Waikiki 1501 | Downtown City Views  Pool & Bbq - Kailua, HI
8.5 13 reviews

Aqua Aloha Surf Waikiki 1501 | Downtown City Views Pool & Bbq

apartment, Urban Honolulu
This Waikiki apartment, a short walk (approx. 1.6km) from Waikiki Beach and within 1.6-2.4km of the International Market Place, Royal Hawaiian Center, and Waikiki Beach Walk, offers easy access to Honolulu's main attractions.
The 33-square-metre self-catering flat features one bedroom, one bathroom, sleeps four (including a sofa bed), and includes a balcony, swimming pool access, and parking; a water park and barbecue facilities are also available within the smoke-free condo building.
Monthly- Discovery Bay 2203 Ocean/sunset/marina/city Views - Q Bed/twin Sofabed - Kailua, HI
9.4 38 reviews

Monthly- Discovery Bay 2203 Ocean/sunset/marina/city Views - Q Bed/twin Sofabed

apartment, Urban Honolulu
Discovery Bay 1902 is a house in Waikiki, a short walk from Kahanamoku Beach and within 2km of Fort DeRussy Beach. It has consistently received excellent user and location ratings and a very good cleanliness rating.
The house has two separate bedrooms, providing privacy and comfort. The property offers a range of amenities including a fully equipped kitchen, air conditioning, a swimming pool, a jacuzzi, a terrace, a garden, a sauna, a spa, a concierge, a fitness centre, and parking.

Best Kailua, HI holiday rentals with parking

Halekulani - No Resort Fee - Kailua, HI
9.3 5482 reviews

Halekulani - No Resort Fee

resort, Urban Honolulu
Halekulani is a luxurious hotel situated on Waikiki Beach, offering stunning views of Diamond Head and easy access to the bustling city centre. The resort has consistently received excellent ratings for its location, cleanliness, and overall experience.
The hotel offers spacious rooms with private balconies and luxurious bathrooms. Guests can enjoy a range of amenities, including a swimming pool, spa, fitness centre, and multiple restaurants serving international cuisine.
Waimānalo Beach Bungalow - Kailua, HI
10 3 reviews

Waimānalo Beach Bungalow

apartment, Waimanalo Beach
This Waimanalo Beach cottage offers direct beach access, situated just steps from the sand in the tranquil Waimanalo district of Oahu.
Sleeping up to five guests, this single-bathroom bungalow features a kitchenette, private courtyard, and ocean views, requiring a minimum 30-night stay as per Honolulu County regulations.
Tropical Kailua Retreat | Walk To Beach + Gym - Kailua, HI
9.9 131 reviews

Tropical Kailua Retreat | Walk To Beach + Gym

apartment, Kailua
La Bella's Bed and Breakfast, a self-catering property in Kailua, Oahu, is located within walking distance of Castle Beach and a short drive (approximately 1.6 to 3.2 km) from Kailua and Lanikai Beaches.
This one-bedroom apartment, sleeping up to three guests, offers two suites with kitchenettes, a daily healthy breakfast, extensive beach equipment (including kayaks and surfboards), an on-site fitness centre, and parking; the property is a grandfathered legal bed and breakfast, avoiding standard rental restrictions.
Gigi's Retreat-kailua Beach Front + Pool - Lic.1990/nuc-1783 - Kailua, HI
9.9 58 reviews

Gigi's Retreat-kailua Beach Front + Pool - Lic.1990/nuc-1783

apartment, Kailua
This Kalama Tract beachfront property offers direct beach access, a 2.4km walk from Kalama Beach Park and Kailua Beach, and within 3.2km of Lanikai Beach and Kailua Bay Beach.
This three-bedroom, three-bathroom Kailua holiday home boasts 186 square metres of living space, sleeps up to 10 guests with a sofa bed, features a private pool, fully equipped kitchen, and outdoor patio with ocean views.

Your Pick of Premium Coastal Stays in Kailua, HI

Live the ultimate tropical fantasy in properties boasting high-end coastal architecture and absolute privacy at luxury holiday rentals in Kailua, HI.

Wg 411 | ½Block To Beach, Diamond Head & Zoo View - Kailua, HI
9.0 100 reviews

Wg 411 | ½Block To Beach, Diamond Head & Zoo View

apartment, Urban Honolulu

Find Holiday Rentals in the CBD of Kailua, HI

Stay steps away from local fish markets, surf shops, and seashore bars at holiday rentals in the heart of Kailua, HI.

Coconut Grove Cottage, Walk To Beach And Downtown - Kailua, HI
10 17 reviews

Coconut Grove Cottage, Walk To Beach And Downtown

apartment, Kailua
Paradise Under The Plumeria Tree - Kailua, HI
9.7 117 reviews

Paradise Under The Plumeria Tree

apartment, Kailua
Beautiful Kailua Hale 1 Bedroom - Kailua, HI
9.8 29 reviews

Beautiful Kailua Hale 1 Bedroom

apartment, Kailua
Private 1 Bedroom Cottage - Kailua, HI
9.9 33 reviews

Private 1 Bedroom Cottage

house, Kailua

Find Holiday Rentals by the Sea in Kailua, HI

Walk directly out of your living room straight onto the soft sand at seashore holiday rentals in Kailua, HI.

111 M² Condo ∙ 2 Bedrooms ∙ 6 Guests - Kailua, HI
9.8 7 reviews

111 M² Condo ∙ 2 Bedrooms ∙ 6 Guests

apartment, Urban Honolulu
Steps To Beach! Gorgeous Partial Ocean View! Ws314 - Kailua, HI
9.9 20 reviews

Steps To Beach! Gorgeous Partial Ocean View! Ws314

apartment, Urban Honolulu
Lanikai Star Guest Studio - Kailua, HI
9.6 124 reviews

Lanikai Star Guest Studio

apartment, Kailua
Gorgeous Beachfront Condo With Fabulous Ocean Views! Fully Renovated! - Kailua, HI
9.9 106 reviews

Gorgeous Beachfront Condo With Fabulous Ocean Views! Fully Renovated!

apartment, Urban Honolulu

Find Holiday Rentals with a Jacuzzi in Kailua, HI

Soak under a canopy of stars just steps from the ocean waves at holiday rentals with a hot tub in Kailua, HI.

39f-high-fl Studio W/ Diamond Head & Ocean Views! - Kailua, HI
9.9 147 reviews

39f-high-fl Studio W/ Diamond Head & Ocean Views!

apartment, Urban Honolulu
Makani Moana - Lanikai, Oahu - Kailua, HI
No reviews

Makani Moana - Lanikai, Oahu

apartment, Kailua
35fl-newly Renovated Hidden Gem 1br / Waikiki - Kailua, HI
9.9 109 reviews

35fl-newly Renovated Hidden Gem 1br / Waikiki

apartment, Urban Honolulu
31fl Newly Renovated With Diamond Head View, Steps To Beach - Kailua, HI
9.0 22 reviews

31fl Newly Renovated With Diamond Head View, Steps To Beach

apartment, Urban Honolulu
©2026 cozycozy.com