Vacation Rentals in Kailua, HI

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Kailua, HI vacation rentals
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481 Vacation rentals and Airbnb in Kailua, HI

Best family friendly Kailua, HI vacation rentals

Among the 481 accommodations in Kailua, HI, here are the 4 best family friendly rentals

Elegant Waikiki Apt 3b/2b, Free Parking - Kailua, HI
9.3 97 reviews

Elegant Waikiki Apt 3b/2b, Free Parking

apartment, Urban Honolulu
This Waikiki apartment, near the Hilton Hawaiian Village and Honolulu Convention Center, offers convenient access to Waikiki Beach and other attractions.
Sleeping up to 10 guests, this spacious three-bedroom, two-bathroom property features two fully equipped kitchens, free on-site parking (rare in Waikiki), and shared laundry facilities; a recent 2022 renovation ensures modern comfort.
8 Guests! Side-by-side Units+2 Free Parking Stalls - Kailua, HI
9.8 273 reviews

8 Guests! Side-by-side Units+2 Free Parking Stalls

apartment, Urban Honolulu
This Waikiki apartment, ideally located in a prime area of Honolulu, offers easy access to Waikiki Beach and its numerous attractions.
Two side-by-side renovated studio units provide comfortable accommodation for groups of up to four, boasting two full kitchens, two bathrooms, two parking spaces, fast WiFi, and two 50" Smart TVs, plus access to a building swimming pool.
Waikiki Banyan, Ocean-view 1br Apt: Full Kitchen, Free Parking, No Resort Fees. - Kailua, HI
9.6 193 reviews

Waikiki Banyan, Ocean-view 1br Apt: Full Kitchen, Free Parking, No Resort Fees.

apartment, Urban Honolulu
This apartment is situated just 0.8 kilometres from Waikiki Beach, in the heart of Honolulu, close to the zoo, aquarium and numerous shops and restaurants. It has received excellent ratings from previous guests.
The apartment is a one-bedroom flat with a floor area of 56 square metres, suitable for up to 4 guests. It comes with a fully equipped kitchen, air conditioning, a terrace, a swimming pool, a jacuzzi, a sauna, parking, and free Wi-Fi.
Beautiful Ocean Views!  A/c, Wi-fi, Washlet, Pool! - Kailua, HI
9.4 120 reviews

Beautiful Ocean Views! A/c, Wi-fi, Washlet, Pool!

apartment, Urban Honolulu
This apartment is conveniently located in Waikiki, just a 10-minute walk from St. Augustine by-the-sea Catholic Church and Waikiki Beach. The property has received excellent ratings for its location, cleanliness, and overall user experience.
This one-bedroom apartment has a floor area of 52 square metres and comfortably accommodates up to four guests. The apartment boasts a fully equipped kitchen, a swimming pool, a garden, and parking, ensuring a comfortable and enjoyable stay.

Best Kailua, HI vacation rentals with a pool

Among the 481 accommodations in Kailua, HI, here are the 4 best rentals with a pool

Golf Course-mountain Views Condo At Waikiki Sunset Half A Block To The Beach - Kailua, HI
9.7 98 reviews

Golf Course-mountain Views Condo At Waikiki Sunset Half A Block To The Beach

apartment, Urban Honolulu
This Waikiki apartment is a short walk (under 1.6km) from Waikiki Beach, Honolulu Zoo, and St. Augustine by-the-Sea Catholic Church, and within 1.6km of the International Market Place and Royal Hawaiian Centre.
The self-catering flat offers one bedroom, one bathroom, sleeps four guests, and includes a kitchen, air conditioning, a swimming pool, fitness centre, tennis court, and parking, plus BBQ facilities and proximity to numerous attractions.
Comfy Modern Waikiki Studio Next To Hilton Village - Kailua, HI
9.7 132 reviews

Comfy Modern Waikiki Studio Next To Hilton Village

apartment, Urban Honolulu
This Waikiki studio apartment is situated on the Waikiki Strip, next to Hilton Village, a short 0.8 km walk from Waikiki Beach and 1.9 km from Ala Moana Shopping Centre, offering easy access to Friday night fireworks at Duke's Lagoon.
The fully renovated (2021) self-catering unit sleeps two, features a king-size bed, Wi-Fi, and access to hotel amenities including a swimming pool, fitness centre, and BBQ area.
Vacation Rental Studios At Royal Garden Waikiki - Kailua, HI
9.3 640 reviews

Vacation Rental Studios At Royal Garden Waikiki

studio, Urban Honolulu
This studio apartment is situated in Waikiki, just under 1 kilometre from Waikiki Beach and 1.6 kilometres from Ala Moana Center, offering easy access to Honolulu's most popular attractions. Guests have consistently rated this accommodation as very good for cleanliness and location, with excellent overall feedback.
The studio features a self-catering kitchenette, perfect for preparing light meals, and a comfortable living space. It also boasts a range of on-site amenities including a swimming pool, fitness centre, sauna, and a guest laundry, ensuring a relaxing and enjoyable stay.
Luxury Ilikai Condo Awesome Sunset And Ocean Views No Resort Fees! Free Wifi - Kailua, HI
9.4 96 reviews

Luxury Ilikai Condo Awesome Sunset And Ocean Views No Resort Fees! Free Wifi

apartment, Urban Honolulu
This luxury apartment is located in Waikiki, just a short walk from Ala Wai Yacht Harbor and Ala Moana Center, and within a 1.5 kilometre walk of Waikiki Beach Walk and the Hawaii Convention Center. The apartment has excellent user ratings and is a great option for travellers looking for a convenient and comfortable stay.
The apartment is a one-bedroom property with one bathroom, suitable for up to five guests. Guests can enjoy a range of amenities including a swimming pool, terrace, and free Wi-Fi, as well as a fully equipped kitchen and a comfortable living area.

Frequently asked questions about holiday rentals in Kailua, HI

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

    You absolutely must spend some time at Kailua Beach Park. It's known for its stunning turquoise waters and powdery white sand. And don't forget to take a walk along the Lanikai Pillbox Hike for breathtaking views of the Mokulua Islands.
  • What are the best Airbnb and vacation rentals in Kailua, HI?

    Absolutely Oceanfront - 60' Waterfall Lap Pool, Private Beachfront Rental and Kailua Beach Park Cottage - 1br are the most popular Airbnb and vacation rentals in Kailua, HI among travelers.

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

    Kailua town is a great option for a vacation rental, as it's close to the beach, shops, and restaurants. It's a lively area with a good mix of local businesses and tourist attractions.
  • 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 fantastic spot for families, with its shallow waters and calm waves. You can also visit the Mokulua Islands for a fun day of snorkeling or kayaking. The nearby Windward Mall offers a variety of shops and restaurants for a family-friendly outing.
  • What are the best vacation 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 usually during the shoulder seasons, from April to May or September to October. You'll find fewer crowds and slightly lower prices compared to the peak season.
  • What are the best rentals for families and kids in Kailua, HI?

  • What events or festivals should visitors check out in and around Kailua, HI?

    The Kailua Town Farmers Market is a popular event held every Saturday morning, featuring local produce, crafts, and live music. The annual Kailua Beach Festival in September is a great way to experience the local culture and enjoy live entertainment, food stalls, and beach activities.
  • What are the best rentals or Airbnbs with a jacuzzi in Kailua, HI?

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

    Kailua Beach Park is free to access, and there are plenty of free things to do there, like swimming, sunbathing, and picnicking. You can also go for a walk or bike ride along the scenic coastline without spending anything.
  • What are the best restaurants with local dishes in Kailua, HI?

    For authentic Hawaiian cuisine, try the popular restaurant, Buzz's Steak House. They're known for their delicious kalua pig and fresh seafood. You can also grab a plate lunch at the local favourite, Kailua Town Tavern, which offers a taste of traditional Hawaiian dishes.
  • What are the best walking or cycling routes in Kailua, HI?

    The Kailua Beach Walk is a beautiful 3.2 km paved path that runs along the coastline, offering stunning views of the ocean and the Mokulua Islands. It's a great option for both walking and cycling.
  • Are there pet-friendly attractions in Kailua, HI?

    Kailua Beach Park is generally dog-friendly, but it's important to check the specific rules and regulations for leash requirements and designated areas. You can also enjoy a walk with your furry friend along the Kailua Beach Walk.
  • What are the benefits of choosing a vacation rental in Kailua, HI?

    Vacation rentals in Kailua offer more space and privacy compared to hotels. You can often find rentals with unique features like private pools or hot tubs, providing a more comfortable and personalized experience.
  • What are the top sports attractions and facilities in Kailua, HI?

    Kailua is a great spot for watersports, with calm waters perfect for stand-up paddleboarding, kayaking, and windsurfing. You can find several rental shops and tour operators in town.

Popular destinations

Best Kailua, HI holiday rentals with a balcony

Iconic Ilikai Hotel #1004. Newly Renovated One Bedroom Unit! - Kailua, HI
9.0 90 reviews

Iconic Ilikai Hotel #1004. Newly Renovated One Bedroom Unit!

apartment, Urban Honolulu
This Waikiki apartment, a 46-square-metre (495 sq ft) flat, is ideally located less than 2km from Ala Moana Centre and the Hawaii Convention Centre, and within a 15-minute walk of Duke Kahanamoku Beach and Waikiki Beach Walk.
Sleeping four guests across two bedrooms and one bathroom, this self-catering property boasts a fully equipped kitchen, private balcony, free Wi-Fi, on-site parking, a swimming pool, and tennis court access.
Waikiki Escape With Lanai, Pool & Beach Access - Kailua, HI
9.6 712 reviews

Waikiki Escape With Lanai, Pool & Beach Access

apartment, Urban Honolulu
This apartment is located in Waikiki, just 800 metres from Kuhio Beach and 450 metres from Queen's Surf Beach, making it a perfect base for exploring this lively area. The property has excellent user, location and cleanliness ratings, ensuring a comfortable and enjoyable stay.
The apartment has one bedroom and one bathroom, covering 56 square metres. It offers a range of amenities, including a swimming pool, tennis court, sauna, hot tub, children's playground, and free parking.
Ocean-view Retreat With Lanai & Free Parking - Kailua, HI
9.7 187 reviews

Ocean-view Retreat With Lanai & Free Parking

apartment, Urban Honolulu
This Waikiki apartment is a short 0.8km stroll from Kuhio Beach and the Royal Hawaiian Shopping Centre, offering easy access to Waikiki's main attractions.
The one-bedroom, one-bathroom flat features a fully equipped kitchen, free parking, a balcony with Diamond Head and ocean views, and access to a swimming pool, jacuzzi, sauna, and garden within the complex.
Ilikai Marina #0788 1 Bedroom 1 Queen 1 Sofa Bed - Kailua, HI
9.2 96 reviews

Ilikai Marina #0788 1 Bedroom 1 Queen 1 Sofa Bed

apartment, Urban Honolulu
This Ilikai Marina condo, situated on the 7th floor and centrally located between Waikiki and Ala Moana shopping districts, offers stunning harbour, Magic Island, and Pacific Ocean views, being steps from Duke Kahanamoku Lagoon and the beach.
This renovated one-bedroom apartment boasts a 60 square metre floor area, sleeps three guests, includes a full kitchen, free Wi-Fi, and access to a coin-operated laundry on the 8th floor, with nearby dining options such as the Chart House and Outback Steakhouse.

Best Kailua, HI holiday rentals with parking

Oceanfront Sunsets! Free Parking Included - Kailua, HI
9.9 60 reviews

Oceanfront Sunsets! Free Parking Included

apartment, Urban Honolulu
This studio flat is located directly on Waikiki Beach, a mere 50 metres from the sand, and within a short walk of numerous local eateries, bars, and shops in Urban Honolulu.
This apartment sleeps four and offers complimentary parking, two swimming pools, a private balcony with ocean views, a new king-size bed, and a queen-size sofa bed, all equipped with air conditioning and Wi-Fi.
Rare Find, Actual 3 Bdrm/2 Bath With Ocean View - Kailua, HI
9.7 174 reviews

Rare Find, Actual 3 Bdrm/2 Bath With Ocean View

apartment, Urban Honolulu
This spacious apartment is located in Waikiki, just a short walk from public transport and the best part of Waikiki beach, offering easy access to the area's attractions and amenities. The apartment has received excellent ratings for location, cleanliness, and overall user experience.
This apartment is a combined 2-bedroom unit and a studio, creating a large 1450+ square foot space. Guests can enjoy a range of amenities including a swimming pool, sauna, fitness centre, and free laundry facilities, all within the building.
Waikiki  Legal  Apt  3b+2b-1 Free Parking - Kailua, HI
9.6 55 reviews

Waikiki Legal Apt 3b+2b-1 Free Parking

apartment, Urban Honolulu
This Waikiki apartment, near Waikiki Beach and the Honolulu Convention Center, offers easy walking access to both.
Sleeping up to 10 guests, this two-unit property features three bedrooms (one king, three queen-size beds), two bathrooms, fully equipped kitchens in each unit, free parking (up to Toyota Sienna size), and paid on-site laundry facilities; an optional second parking space is available for £20 per day.
Waikiki Banyan 3411 Ocean View - Free Parking - Kailua, HI
9.2 71 reviews

Waikiki Banyan 3411 Ocean View - Free Parking

apartment, Urban Honolulu
This one-bedroom apartment is situated in Waikiki, just a 0.8 kilometre walk from Kuhio Beach and 450 metres from Queen's Surf Beach. The apartment offers free private parking, a swimming pool, a Jacuzzi, a terrace, a garden, a fitness centre, and free Wi-Fi, as well as a fully equipped kitchen with a fridge and microwave oven.
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