Kailua Vacation Rentals

Welcome to the charming tropical community if Kailua. Kailua is in Hawaii County, Hawaii on the island of Hawaii. This tropical paradise is home to more fun and exciting activities then anyone could participate in during one vacation! Once you are settled into your vacation rental property consider charting yourself and your fellow vacationers a private helicopter tour of the island. Imagine soaring through the sky with just your friends and family as the pilot tours you around the breathtaking tropical wonderland below. Not a bad way to get the lay of land down for your vacation! Have you ever kayak on a river or stream? If so, elevate your kayaking game in Kailua by renting a kayak and take it into the ocean. Ride waves and explore the vast water for a day of fun! Do you or your fellow vacationers enjoy golf? Head to one of the local golf courses and play around of eighteen. Hitting the links while being surrounded by tropical beauty of the area is truly a great experience! The local beaches are another great place to spend some time while vacationing in Kailua. Swim, surf, tan and explore the various beaches for tons of fun in the sun! Guests that are new to surfing are strongly encouraged to take a local surf class before hitting the waves. When your ready to get an up-close look at the marine life in area, sign up and join a snorkeling or scuba diving guided tour. With so much fun to be had in the area, guests vacationing in Kailua are sure to have an unforgettable vacation experience!

Compare Airbnb, VRBO and direct by owner prices and get the best deal

Search for your Kailua vacation rental in HiChee and compare prices between Airbnb, VRBO and direct by owner for the same rental. See our live price comparison and take a look at how much you can save by getting the best deal.

Kailua vacation rental direct by owner

We not only offer a wide selection of Airbnb and VRBO vacation rentals on Kailua but also the possibility of direct communication with the owner.

Activities in Kailua

• Helicopter tour
• Ocean kayaking
• Golf
• Explore and have fun on beaches
• Take a surf class
• Snorkel or Scuba Dive
• Much more!!

With the vast amount of ways to have fun and explore Kailua that guests are offered, we are sure they will work up an appetite. The dining in this area is the perfect mixture of local Hawaiian foods and staple American cuisine that we all know in love. Start your morning of right with a cup of Hawaiian coffee and various Hawaiian breakfast items at Cinnamon’s Restaurant. With a delicious Hawaii breakfast and coffee in your belly you will be fueled up and ready for a day of fun in the sun! If you want to sample some of the local Hawaiian dishes served for lunch and dinner, we highly recommend a visit to Uahi Island Grill. This fine local eatery offers a variety of local dishes and is a great place to try new and exciting dishes. Craving a mouthwatering steak after a day of fun and adventure? Head to Buzz’s Original Steak House a devour a juicy bone-in ribeye! If you are looking for quick casual American food or a way to treat yourself after a day of exercise be sure to visit either Bob’s Boston Pizza or Teddy’s Bigger Burgers. With a great mix of local cuisine and standard American cuisine, everyone vacationing with you will find a restaurant in Kailua that they will love!

Restaurants in Kailua

• Uahi Island Grill
• Cinnamon’s Restaurant
• Buzz’s Original Steak House
• Bob’s Boston Pizza
• Teddy’s Bigger Burgers
• Many more!!

The shopping scene in Kailua perfectly personifies the general vibe of the local population in Kailua. Visit Kailua Farmers Market and try a variety of the fresh local produce grown in the area. Visit Oeno Winemaking and learn to make your own wine just like the master growers on the island. Stop into Manoa Chocolate Hawaii and indulge in a variety of hand crafted chocolates created by local chocolatiers. Looking for a new book to read on the beach? Head to Book Ends and peruse their fine selection of elegant literature. Don’t forget to make time while in the area to check out the glass artwork at Island Glasswork. Most of the retail locations in this area sell products that are created by locals and sold by locals. This small-town community vibe is clearly tangible as you spend time shopping in the area.

Shopping in Kailua

• Kailua Farmers Market
• Manoa Chocolate Hawaii
• Oeno Winemaking
• Book Ends
• Island Glassworks
• Many more!!

HiChee.com is the best and most efficient place for finding, planning, and booking your Hawaiian vacation. From the beautiful scenery and beaches located all over the islands to the unique small-town surf vibes and truly unparalleled shopping, guests of all ages are sure to have an unforgettable time. HiChee.com aims to take the hassle and stress out of booking your vacation rental property, so all you must do is decide if you would rather hit the beach or head into town first. Book now, the experience of a lifetime awaits!