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.

Part Ocean View, Beach Theme 23rd Fl, Free Parking With Wifi, Ac - Kailua, HI
10 3 reviews

Part Ocean View, Beach Theme 23rd Fl, Free Parking With Wifi, Ac

apartment, Urban Honolulu
This Waikiki apartment is located steps from Waikiki Beach, a short walk from the International Market Place and Royal Hawaiian Centre.
The 56 square metre (603 square foot) self-catering flat offers one bedroom, one bathroom, and sleeps up to five guests, boasting a private lanai, free Wi-Fi, parking, and access to a swimming pool, jacuzzi, sauna, and garden.
@ Marbella Lane Mountain View Studio, Steps From Wakiki Beach - Kailua, HI
9.1 414 reviews

@ Marbella Lane Mountain View Studio, Steps From Wakiki Beach

studio, Urban Honolulu
This studio apartment is located in Waikiki, Honolulu, just 15 steps from the beach and 11 minutes (8km) from the airport, offering a prime beachfront location in the heart of this vibrant area. It has consistently received excellent ratings for its location, cleanliness, and overall user experience.
The apartment features a comfortable bedroom and bathroom, along with a fully equipped kitchen and a balcony. Guests can enjoy access to a swimming pool, a tennis court, a garden, and a bar, as well as a range of activities, including water sports, diving, fishing, and bicycle and car rentals.
1107 Waikiki 6 Beds Free Parking Floor 11 - Kailua, HI
9.5 123 reviews

1107 Waikiki 6 Beds Free Parking Floor 11

apartment, Urban Honolulu
This Waikiki condo is situated near the Ala Wai Canal, approximately 1.6km from Waikiki Beach and its attractions.
The fully renovated apartment offers an open-plan layout, sleeping up to eight guests in six beds, with free on-site parking, a swimming pool, and BBQ area, plus beach essentials provided.
Ocean Canal Mountain View Steps From Waikiki Beach 6person - Kailua, HI
8.0 50 reviews

Ocean Canal Mountain View Steps From Waikiki Beach 6person

studio, Urban Honolulu
This Waikiki studio apartment is situated a short distance from Waikiki Beach, a 12-minute walk from the Royal Hawaiian Shopping Center and 0.5km from the Hawaii Convention Center.
The 300 square metre self-catering apartment sleeps up to 11 guests and features a fully equipped kitchen, swimming pool access, free Wi-Fi, and on-site parking.

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.

Modern Ilikai 16th Floor Harbor Studio - Surfing, Sunset & & Yacht Views! - Kailua, HI
9.2 302 reviews

Modern Ilikai 16th Floor Harbor Studio - Surfing, Sunset & & Yacht Views!

studio, Urban Honolulu
This apartment is conveniently located in Waikiki, just a 15-minute walk from both Duke Kahanamoku Beach and Waikiki Beach Walk, putting you right in the heart of Honolulu's bustling tourist scene. It has received very good user ratings and excellent ratings for location and cleanliness.
The 46 square metre flat has one bedroom and one bathroom, offering a comfortable space for a couple or small family. You will enjoy a range of amenities including a private pool, a balcony, and a fully equipped kitchen with a fridge, freezer, and microwave, as well as internet access and a washing machine.
Aqua Aloha Surf Waikiki 908 | Downtown City Views  Pool & Bbq - Kailua, HI
9.0 2 reviews

Aqua Aloha Surf Waikiki 908 | Downtown City Views Pool & Bbq

apartment, Urban Honolulu
This Waikiki condo is situated a short walk from Waikiki Beach and International Market Place, with the Royal Hawaiian Centre and Waikiki Beach Walk within a 1.6km radius.
This 34 square metre apartment offers one bedroom, one bathroom, sleeps four guests, and includes a balcony, washing machine, and access to an on-site water park and barbecue grills.
Luana 502 -Breathtaking Waikiki Studio Sleeps 4 - Kailua, HI
9.5 22 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 & Iconic Waikiki Views From The Marine Surf By The Beach W/full Kitchen - Kailua, HI
9.8 22 reviews

Ocean & Iconic Waikiki Views From The Marine Surf By The Beach W/full Kitchen

apartment, Urban Honolulu
This apartment is situated in the heart of Waikiki, just a kilometre from the beach and within a 10-minute walk of the International Market Place, Royal Hawaiian Center, and Waikiki Beach Walk. It has received excellent ratings for location, cleanliness, and user experience.
This two-person flat features a fully equipped kitchen, a washing machine, a sofa bed, and free Wi-Fi. Guests can enjoy the convenience of a private balcony, a swimming pool, a garden, and parking, all within a smoke-free environment.

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.

Jenny's Pineapple Cottage - Kailua, HI
9.5 345 reviews

Jenny's Pineapple Cottage

apartment, Urban Honolulu
Jenny's Cottage Waikiki is a short walk from Saint Augustine by-the-Sea, Kuhio Beach, and Waikiki Beach, offering a convenient location in the heart of Honolulu's bustling tourist district. The property consistently receives excellent ratings for location, cleanliness, and overall user experience.
This one-bedroom apartment features a private lanai with stunning ocean views, perfect for relaxing and enjoying the Hawaiian breeze. Guests can enjoy a range of amenities, including a swimming pool, tennis court, and free luggage storage, as well as a kitchenette with an oven, microwave, and toaster.
Steps From The Beach Family Retreat W/free Parking In Boutique Style Building - Kailua, HI
9.0 738 reviews

Steps From The Beach Family Retreat W/free Parking In Boutique Style Building

apartment, Urban Honolulu
This apartment is located in Waikiki, just 1 kilometre from Honolulu Zoo and Waikiki Beach, with International Market Place and Kaimana Beach within a 1.5 kilometre radius. The apartment has excellent user, location, and cleanliness ratings.
The apartment has one bedroom and one bathroom, covering 34 square metres. The apartment offers a range of amenities including a swimming pool, a tennis court, a garden, a terrace, parking, and a fully equipped kitchen.
Hyatt Regency Waikiki Beach Resort & Spa - Kailua, HI
8.9 6825 reviews

Hyatt Regency Waikiki Beach Resort & Spa

resort, Urban Honolulu
The Hyatt Regency Waikiki Beach Resort & Spa is directly on Waikiki Beach, putting you right in the heart of this famous Honolulu district. The hotel has excellent user ratings for its location, cleanliness, and overall experience.
The hotel offers a range of modern rooms with balconies and ocean views. Guests can enjoy a variety of amenities, including multiple restaurants, a spa, a fitness centre, a swimming pool, and a bar.
Studio Unit At The Royal Garden, In Waikiki ワイキキ・ロイヤルガーデン - Kailua, HI
8.9 70 reviews

Studio Unit At The Royal Garden, In Waikiki ワイキキ・ロイヤルガーデン

studio, Urban Honolulu
This Waikiki studio apartment boasts a prime location, close to Waikiki Beach, Kahanamoku Beach, and a 1.6km stroll from Fort DeRussy Beach, offering easy access to major attractions such as the Royal Hawaiian Theatre Legends in Concert Waikiki and the Royal Hawaiian Shopping Centre.
The self-catering unit features a kitchenette with a fridge and microwave, a private balcony with seasonal barbecue facilities, complimentary Wi-Fi, and access to a swimming pool, jacuzzi, fitness centre, sauna, and valet parking; sleeping one guest comfortably.

Best Kailua, HI holiday rentals with parking

Ilikai Marina 480 - Kailua, HI
8.9 11 reviews

Ilikai Marina 480

house, Urban Honolulu
This one-bedroom flat is located in the Waikiki district of Honolulu, just a six-minute walk from Kahanamoku Beach and less than a mile from Fort DeRussy Beach, putting you right in the heart of the action. The apartment has received very good user ratings, an excellent location rating and a good cleanliness rating.
The 64 square metre flat comfortably sleeps four guests and includes a fully equipped kitchen with a fridge, microwave, and dishwasher. You’ll also find air conditioning, free Wi-Fi, a TV, parking, and a bathroom with a hairdryer.
Upgraded 1br Condo Ocean View - Kitchen, Free Parking, Wifi - Kailua, HI
8.9 148 reviews

Upgraded 1br Condo Ocean View - Kitchen, Free Parking, Wifi

apartment, Urban Honolulu
This Waikiki apartment, situated on the 14th floor of Tower I, offers expansive views and is conveniently located near Waikiki Beach.
The 55-square-metre (592-square-foot) flat features a separate kitchen and dining area, sleeps up to six guests, and includes a private terrace, swimming pool, jacuzzi, and free covered parking.
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
This Waikiki apartment, a 46 square metre flat, is excellently located less than 1.6km from the Royal Hawaiian Centre and International Market Place, and a 15-minute walk from Duke Kahanamoku Beach and Waikiki Beach Walk.
The self-catering property boasts a private patio, a swimming pool, free Wi-Fi, and can comfortably accommodate four guests, with all the amenities of a fully equipped kitchen and one bathroom.
Waikiki Surfer Studio | Modern | Ocean Views - Kailua, HI
9.7 109 reviews

Waikiki Surfer Studio | Modern | Ocean Views

apartment, Urban Honolulu
This Waikiki studio apartment is centrally located near Ala Wai Boulevard, less than 0.8 kilometres from Waikiki Beach and within walking distance of Ala Moana Center and Honolulu Zoo.
The self-catering unit, sleeping two guests, boasts a fully equipped kitchenette, a swimming pool, jacuzzi, fitness centre, and secure parking, all within a building offering 24/7 security and self check-in.

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.

@ Marbella Lane - Marina Studio | Near The Beach - Kailua, HI
9.3 123 reviews

@ Marbella Lane - Marina Studio | Near The Beach

studio, 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.

Disconnect Off Grid - Kailua, HI
10 1 review

Disconnect Off Grid

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

Kailua Hale 1 Bedroom

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

Paradise Under The Plumeria Tree

apartment, Kailua
Kailua Beach Villa - 1990/nuc-1798 - Kailua, HI
9.4 149 reviews

Kailua Beach Villa - 1990/nuc-1798

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.

Deluxe Mountain View Unit At The Waikiki Banyan - Kailua, HI
10 1 review

Deluxe Mountain View Unit At The Waikiki Banyan

apartment, Urban Honolulu
Modern 1-bedroom Condo In Lovely Honolulu With Wifi, Ac, Parking - Kailua, HI
10 3 reviews

Modern 1-bedroom Condo In Lovely Honolulu With Wifi, Ac, Parking

apartment, Urban Honolulu
Oahu Dream! 3 Amazing Units, Minutes To Waikiki Aquarium, Waikiki Beach Walk - Kailua, HI
No reviews

Oahu Dream! 3 Amazing Units, Minutes To Waikiki Aquarium, Waikiki Beach Walk

apartment, Urban Honolulu
Top Remodel Of A Gorgeous Diamond Head Oceanfront Lanai Condo - Sleeps 4 - Kailua, HI
9.7 53 reviews

Top Remodel Of A Gorgeous Diamond Head Oceanfront Lanai Condo - Sleeps 4

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.

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
Stunning 15th Floor Luana King Bed Condo Sleeps 4 Guests - Kailua, HI
9.4 50 reviews

Stunning 15th Floor Luana King Bed Condo Sleeps 4 Guests

apartment, Urban Honolulu
Waikiki Sunsets & Summer Memories| 3 Studios - Kailua, HI
8.0 8 reviews

Waikiki Sunsets & Summer Memories| 3 Studios

apartment, Urban Honolulu
Hilton Grand Vacations Club Grand Waikikian Honolulu - Kailua, HI
8.8 1109 reviews

Hilton Grand Vacations Club Grand Waikikian Honolulu

resort, Urban Honolulu
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