Vacation Rentals in Kailua, HI

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Kailua, HI holiday rentals
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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.

1bd Condo Diamond Head & Ocean View Free Parking Free Amenities Walk To Beach - Kailua, HI
10 1 review

1bd Condo Diamond Head & Ocean View Free Parking Free Amenities Walk To Beach

apartment, Urban Honolulu
This Waikiki condo offers a one-bedroom apartment for four guests, within walking distance of Waikiki Beach and numerous restaurants, shops and parks in Honolulu, Oahu.
The fully furnished flat includes a kitchen with fridge and microwave, air conditioning, a private lanai with Diamond Head and partial ocean views, on-site parking (fee applies for lost fob), a swimming pool, and complimentary coffee, tea, condiments and beach gear.
Waikiki Banyan Ocean & Diamond Head View 19th Fl Free Parking - Kailua, HI
8.4 5 reviews

Waikiki Banyan Ocean & Diamond Head View 19th Fl Free Parking

house, Urban Honolulu
This Waikiki holiday home is conveniently located less than 1.5 kilometres from the Royal Hawaiian Shopping Centre and a 3-minute walk from Saint Augustine by the Sea church.
The 56-square-metre property offers one bedroom, one bathroom, and sleeps up to seven guests, boasting a swimming pool, tennis court, free parking, and free Wi-Fi; enjoy nearby beach access and explore the area's attractions.
Penthouse | 1,700 Sq Ft | 3br/2ba | Parking | Pool - Kailua, HI
9.9 84 reviews

Penthouse | 1,700 Sq Ft | 3br/2ba | Parking | Pool

apartment, Urban Honolulu
This Waikiki penthouse apartment boasts stunning views of Ala Wai Boulevard, the canal, a golf course, Honolulu's cityscape, and Landmark Tower, offering partial ocean views and convenient access to Waikiki Beach.
The three-bedroom, two-bathroom property sleeps up to twelve guests, features a modern kitchen with high-end appliances, a Peloton bike, Nintendo Switch, in-unit laundry, and two secure parking spaces, plus building amenities including a swimming pool and BBQ area.
The Kahala Hotel And Resort - Kailua, HI
9.1 5685 reviews

The Kahala Hotel And Resort

resort, East Honolulu
The Kahala Hotel and Resort is located in East Honolulu, a short distance from the Honolulu Zoo and a 20-minute drive from the airport, offering a tranquil escape from the city buzz. This hotel consistently receives excellent ratings for its location, cleanliness, and overall experience.
The resort boasts a direct beachfront location, providing stunning ocean views and easy access to the sand. It offers a range of amenities and activities, including swimming pools, a spa, a fitness centre, tennis courts, and a variety of dining options, making it an ideal choice for families and couples alike.

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.

Waikiki Banyan Rainbow Suite With Ac & Free Parking - Kailua, HI
No reviews

Waikiki Banyan Rainbow Suite With Ac & Free Parking

apartment, Urban Honolulu
This newly remodelled condominium is situated in Waikiki, a mere 50 metres from Waikiki Beach, offering peaceful mountain views and convenient access to the Royal Hawaiian Centre and Waikiki Beach Walk.
This one-bedroom apartment, ideal for up to six guests, features a private bedroom with two queen-size beds, quiet air conditioning, a fully equipped kitchen, and access to a shared recreation deck with a swimming pool, hot tub, sports court, and playground, plus secure covered parking.
Moana Surfrider, A Westin Resort & Spa, Waikiki Beach - Kailua, HI
9.0 2465 reviews

Moana Surfrider, A Westin Resort & Spa, Waikiki Beach

resort, Urban Honolulu
The Moana Surfrider, A Westin Resort & Spa, Waikiki Beach is located directly on Waikiki Beach in Honolulu, just a short drive from Honolulu City Hall and the University of Hawai’i at Manoa. The hotel is highly rated, with excellent location, very good cleanliness and user reviews.
The hotel offers a range of rooms and suites with balconies boasting stunning ocean or city views. Guests can enjoy a variety of amenities, including a spa, multiple restaurants, a fitness centre, and a swimming pool, as well as activities like surfing lessons, catamaran sails, and canoe rides.
Waikiki Ocean View Studio, Easy Walk To Beach, Shopping, Restaurants - Kailua, HI
9.0 6 reviews

Waikiki Ocean View Studio, Easy Walk To Beach, Shopping, Restaurants

studio, Urban Honolulu
This Waikiki studio apartment enjoys a central location, offering easy access to Waikiki Beach and Ala Moana Center, with Honolulu Zoo and the Hawaii Children's Discovery Centre within a short drive.
The self-catering apartment sleeps six guests, features a fully equipped kitchen including a dishwasher, and boasts a terrace, swimming pool, and air conditioning, alongside Wi-Fi and bathroom essentials.
Waikiki Escape W/ Pool & Free Parking - Kailua, HI
9.7 81 reviews

Waikiki Escape W/ Pool & Free Parking

apartment, Urban Honolulu
This Waikiki condo is located a short walk from Waikiki Beach and close to attractions such as the International Market Place, within 1.6km of the Royal Hawaiian Centre and Waikiki Beach Walk, and under 1km from St. Augustine by-the-Sea Catholic Church.
The 56 square metre apartment features one bedroom, one bathroom, sleeps four guests, and includes a balcony, swimming pool, jacuzzi, and free WiFi in public areas; on-site amenities include a water park and spa tub.

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.

Beautiful Honolulu Waikiki Ocean View Condo - Kailua, HI
10 1 review

Beautiful Honolulu Waikiki Ocean View Condo

apartment, Urban Honolulu
This beachfront flat in Waikiki, Honolulu, is situated 300 metres from Ala Wai Harbour and 800 metres from Ala Moana Centre.
This 60 square metre apartment accommodates up to eight guests, featuring one bedroom, two bathrooms, air conditioning, Wi-Fi, and a full kitchen, with on-site parking available.
Less Than A One Minute Walk To Kailua Beach, Pool, Bikes, Bbq, A/c, And More - Kailua, HI
9.6 164 reviews

Less Than A One Minute Walk To Kailua Beach, Pool, Bikes, Bbq, A/c, And More

apartment, Kailua
This Kailua flat is situated near the coast, within a 2.4km walk of Kailua and Lanikai Beaches and under 3.2km from Kailua Bay Beach and Kalama Beach Park.
The self-catering apartment offers a one-bedroom, one-bathroom layout sleeping two, boasting a kitchenette, balcony, swimming pool, jacuzzi, spa, and parking, with easy access to nearby beaches and barbecue grills.
Wyndham Vacation Resorts Royal Garden At Waikiki - Kailua, HI
9.1 1533 reviews

Wyndham Vacation Resorts Royal Garden At Waikiki

resort, Urban Honolulu
The Wyndham Vacation Resorts Royal Garden At Waikiki is a 3-star hotel in Waikiki, Honolulu, a short walk from Waikiki Beach, Kahanamoku Beach, and the Royal Hawaiian Theater. It enjoys a great location with excellent user ratings for location, cleanliness and overall experience.
The hotel features a range of amenities for a comfortable stay, including a swimming pool, jacuzzi, terrace, garden, sauna, spa, restaurant, bar, fitness centre, tennis court, and valet parking. Guests can also enjoy the convenience of internet access, air conditioning, and a concierge service.
Kailani Loft, Kailua Coconut Grove 1-bedroom - Kailua, HI
8.5 55 reviews

Kailani Loft, Kailua Coconut Grove 1-bedroom

apartment, Kailua
The Kailani Loft is a one-bedroom apartment in Kailua, conveniently located an 18-minute walk (approximately 1.45 km) from Kailua Beach and within 13-21 km of Nuʻuanu Valley Rain Forest, Foster Botanical Garden, and the Honolulu Museum of Art.
This 60 square metre self-catering flat offers a spacious layout with a separate bedroom and living room, accommodating up to five guests and boasting a balcony with mountain views, private parking, complimentary Wi-Fi, and air conditioning.

Best Kailua, HI holiday rentals with parking

37th Flr Elegant Ocean View Studio|king Bed|waikiki - Kailua, HI
9.9 73 reviews

37th Flr Elegant Ocean View Studio|king Bed|waikiki

studio, Urban Honolulu
This luxurious Waikiki condo, situated on the 37th floor, offers spectacular ocean, golf course, and city views and is steps from Waikiki Beach and the International Market Place.
The 37-square-metre apartment sleeps two, features a king-size bed, a fully equipped kitchen with dishwasher, a private lanai, and access to a swimming pool, jacuzzi, sauna, and fitness centre; beach chairs and towels are provided.
Ocean-view Escape With Pool, Hot Tub & Parking - Kailua, HI
9.3 52 reviews

Ocean-view Escape With Pool, Hot Tub & Parking

apartment, Urban Honolulu
This one-bedroom apartment is located in Waikiki, just 800 metres from Queen's Surf Beach and Kuhio Beach, offering easy access to the vibrant beach scene and the heart of Honolulu. It has received excellent ratings for its location, cleanliness, and overall experience.
The 56 square metre apartment comfortably accommodates four guests and features a well-equipped kitchen, a balcony with ocean views, a rooftop pool, a sauna, a hot tub, and private parking. Guests can enjoy the convenience of a fully equipped kitchen, a rooftop pool, and a range of wellness amenities.
Marine Surf Waikiki 2108 - Parking Included - Kailua, HI
9.7 452 reviews

Marine Surf Waikiki 2108 - Parking Included

apartment, Urban Honolulu
This apartment is situated in the Waikiki district of Honolulu, just a short walk from Waikiki Beach, the Royal Hawaiian Shopping Center and the Royal Hawaiian Theater Legends in Concert Waikiki. It has consistently received excellent ratings for its location, cleanliness and overall experience, making it a great choice for travellers.
The apartment offers one bedroom and one bathroom, covering 36 square metres. You'll enjoy access to a range of amenities including a swimming pool, Jacuzzi, fitness centre, tennis court and parking, as well as a terrace, garden, air conditioning, internet and a kitchen with a fridge and microwave oven.
Condotel Quiet With High Ceiling Free Parking And Wifi - Kailua, HI
8.7 7 reviews

Condotel Quiet With High Ceiling Free Parking And Wifi

apartment, Urban Honolulu
Holiday rental listing with an excellent rating of 87% based on 7 reviews. Your accommodation will be based in Urban Honolulu.
Facilities and services include an iron, a swimming pool and an elevator. Enjoy free parking with this accommodation in Urban Honolulu!

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.

Waikikihawaii Ocean View! Renovated Clean Studio - Kailua, HI
9.8 63 reviews

Waikikihawaii Ocean View! Renovated Clean Studio

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
Home Sweet Home-minutes To Kailua Town And Beach - Kailua, HI
9.8 9 reviews

Home Sweet Home-minutes To Kailua Town And Beach

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

Private 1 Bedroom Cottage

house, Kailua
Kailua Hale 1 Bedroom - Kailua, HI
10 27 reviews

Kailua Hale 1 Bedroom

apartment, 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.

Wg 705 Cozy Queen-bed Studio Steps To Waikiki Beach & Zoo W/ac, Pool, & Kitchen - Kailua, HI
9.6 5 reviews

Wg 705 Cozy Queen-bed Studio Steps To Waikiki Beach & Zoo W/ac, Pool, & Kitchen

studio, Urban Honolulu
Comfortable King Bed Waikiki Studio 2 Mins Walk To Beach With Wifi & Ac - Kailua, HI
8.6 10 reviews

Comfortable King Bed Waikiki Studio 2 Mins Walk To Beach With Wifi & Ac

studio, Urban Honolulu
Waikiki Spacious One Bedroom Ocean View - Kailua, HI
9.8 131 reviews

Waikiki Spacious One Bedroom Ocean View

apartment, Urban Honolulu
City-view Ilikai Hotel One-bedroom Condo On The 10th Floor - Kailua, HI
9.5 14 reviews

City-view Ilikai Hotel One-bedroom Condo On The 10th Floor

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.

Awesome View. Walking Distance To Beach, Restaurants, Shopping - Kailua, HI
9.4 30 reviews

Awesome View. Walking Distance To Beach, Restaurants, Shopping

apartment, Urban Honolulu
Hilton Waikiki Beach Resort & Spa - Kailua, HI
8.4 4150 reviews

Hilton Waikiki Beach Resort & Spa

resort, Urban Honolulu
Downtown Honolulu Condo With Free Parking! - Kailua, HI
9.8 68 reviews

Downtown Honolulu Condo With Free Parking!

apartment, Urban Honolulu
Pool & Jacuzzis, Free Parking, Wifi, Ac, Comfy Beds, Bbq, And Great View - Kailua, HI
9.4 183 reviews

Pool & Jacuzzis, Free Parking, Wifi, Ac, Comfy Beds, Bbq, And Great View

apartment, Urban Honolulu
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