Vacation rentals in Kailua
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Top-rated vacation rentals in Kailua
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Kailua Beach Park - 1 BR Cottage
Kailua Beach was once again been rated as the best beach in the USA for 2019, by Dr. Beach." The cottage is directly across the street from Kailua Beach Park and less than a 2-minute walk to step into the ocean. It is a legal vacation rental, license number 1990/NUC-1758. The property is tucked away one house back from the road into Lanikai, and described by guests as "a little oasis of quiet and calm." The bathroom has been remodeled with a new showers, sinks and plumbing fixtures April 2022!
Secluded White Sandy beach just 30 steps away
Enjoy the 17% discount (as I pay the taxes out of the proceeds of your payment unlike most other listings that add it on) Don’t be fooled by the other smaller studios with just a niche that barely fits a bed. This is the largest true one bedroom model at Pats. This beautiful beachfront condo is the most preferred unit located at the far end on the ground floor just 30 steps to the powdery white sand beach with the only door facing East. Assigned parking close by. Avoid lengthy elevator waits
Honu Suite at La Bella’s-Walk to Beach-Licensed
No detail is overlooked at this charming and luxurious home. La Bella’s Bed and Breakfast is the place to be if you are looking for a short walk to the beach, a beautiful garden to enjoy, great host family that lives onsite and close to amenities. Our luxury bedding and upgraded style makes you feel right at home during your Hawaii vacation. The Honu (Turtle) Suite: -AC -Queen bed -Full kitchen -Private bathroom This suite is extra private -located away from the rest of the living quarters.
Ocean View w/ 2 private balconies; Steps to Beach
BEST LOCATION & OCEAN VIEWS! Steps to Waikiki Beach & all the action! No car needed Newly renovated condo 1/2 block to the beach on 9th floor of Waikiki Grand Hotel. Across from the Zoo in Kapiʻolani Park. Enjoy 2 private balconieswith Ocean/Diamond Head views. 1 Queen bed & 1 Queen Pull Out. Dividers provided to convert into 1 bedroom if needed. See photos of Full Kitchenette & beach gear included LEGAL VACATION RENTAL All taxes/fees included—your family or solo dream vacation starts here!
Kailua Pineapple Studio. Walk to Beach! PERMITTED
Legal, permitted short-term rental (Permit #1990/NUC-1819, Tax map key:43073024) *not impacted by Honolulu ordinances banning Short-term Rentals Hawaiian style, modern appointments. Beautiful 450 sf suite in the one of the most desirable locations in Hawaii, Kailua! An easy 8-10 min. walk to Kailua Beach, top rated in the world. Private residence at the end of a quiet cul-de-sac. Airbnb “Guest Favorite” awardee! Sister Unit: Kailua Palm Studio. Walk to Beach! PERMITTED Managed by Kupono Svcs.
Beachfront Getaway - Hawaiian Princess Condo
Mesmerizing sunset views from this sandy beach front condo. Nothing separates you from sparkling turquoise waters but footprints in the sand. Balcony is ideal height for turtle watching. From Nov- April you may spot a whale. This vibrant land is full of surprises. Even dolphins spin by now and then. Escape the crowds of Waikiki to experience a real Hawaiian lifestyle. Snorkel, boogie board or surf right out your door. Awakening to the rhythm of the ocean can change your life forever.
Amazing Waikiki Beach Views!!
Perfect vacation getaway, with amazing views of Waikiki Beach and Lagoon!! Best location, walking distance to many points of interest, Ala Moana Mall/Designer stores and many restaurants! Enjoy visiting Oahu - there's sightseeing, swimming, hiking, surfing or shopping etc! Enjoy watching the fireworks every Friday nights from the patio, sponsored by Hilton Hawaiian Village! Hotel pool is also available for our guests. Also accepting long term stays at special rates.
Studio at Marriott vacation club ko olina
Feel free to message me a request to book and the times you are looking for. The price shown is for the Mountain View Studio w/kitchenette that sleeps 4, 1 King and a Sofa Bed. Price is over half of the cost if you book direct with the hotel. Also includes FREE parking where hotel charges $45/day. The most beautiful resort and Guest room in Ko Olina right on the beach in a picturesque lagoon. 30 minutes from the airport and Honolulu. * Free WiFi, Free self-parking.
32F-Penthouse Pacific Monarch Studio-Ocean View
Experience the epitome of luxury with this stunning, spacious ocean view studio situated on the 32nd Penthouse floor right in the heart of Waikiki. Boasting breathtaking views of the ocean and Diamond Head, this upscale studio goes above and beyond to exceed all expectations. Indulge in the ultimate comfort and elegance while enjoying the convenience of being in the center of Waikiki, surrounded by the vibrant energy and beauty of this renowned beach destination.
"Coconut Cottage by the Sea" Steps to the beach!
Aloha & Welcome to Punaluu! Enjoy a memorable visit when you stay in this unique sandy beachfront cottage! Important! Please keep reading for information about the renovations going on at the property. Incredible view of the ocean & you will love amazing sunrises right out your window! This special condo has a great little kitchen & new king bed. Perfect for swimming, snorkeling, paddleboarding & just relaxing on the beach! BBQ area, pool, gym & security.
♥ North Shore Paradise at Turtle Bay ♥
For the discerning traveler, a designer curated space with every luxury detail thought of. When you step inside, you can feel the love poured into this space, and the exquisite detailed craftsmanship throughout. Nestled on the 3rd green of the famous Georgia Fazio course at Turtle Bay Kuilima Estates West on the North Shore of Oahu. A perfect spot to vacation, honeymoon, or spend some quality relaxation time. This magical space welcomes you with aloha.
Kailua Beach Cottage - 1990/NUC-1797
WE HAVE PERMIT - 90/TVU-0287 FROM THE CITY & COUNTY WE WERE RATED BY AIRBNB AS A SUPERHOST. KAILUA BEACH RATED #1 BEACH IN AMERICA! This place is good for couples, business travelers, and families. (On the 2nd floor - upstairs) *Additional guest fee of $90 per person per day applies to parties over 4 people. Additional service fee and tax will apply. Visit the 8 Bdrm Villa website for a larger family group.
Popular amenities for Kailua vacation rentals
Stay near Kailua's top sights
Kailua beachfront vacation rentals
*Remodeled Oceanfront in Waikiki - Ilikai Marina
Waikiki Shore - Beachfront
1280 Ilikai Marina • 1BD – Ocean & Fireworks View
★Panoramic OCEAN VIEW Studio Suite + FREE Parking
Beach Beauty and Comfort in remote Oahu Paradise
Beautiful Oceanfront Paradise Condo
*Serendipity on the Moana! - Legal & Beachfront!*
Dreamy Beachfront Cottage with Breathtaking Views
Kailua home rentals
Haleiwa Waterfront House
Waikiki Gem, Stunning Ocean View, Parking Included
Large family home 5 min from beach- with pool
North shore Studio with sauna! - Walk to beach!
Makaha Hale - Serene 3 BR Home
Slice of Paradise-3BR- Sleeps10-Same$ for 10 as 2
Beautiful 4-BR Home| Near Beach| Mountain View
3BR New Construction w/Mt views, Close to Beach
Beachfront home rentals in Kailua
Orchid Paradise- AC, Close to beach
Summer Starts Here! Turtle Bay’s Kuilima West #104
Newly Renovated Villa Walk to Beach + Pool
Waikiki Close To Ala Moana, Pool and Parking!
Honolulu Oasis for your Hawaiian retreat
"HALE HONU" North Shore Beach House
Cozy Beachfront Unit
Serenity Beachfront Cottage- NUC No 90/TVU-0326
When is the best time to visit Kailua?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | R3,638 ZAR | R3,704 ZAR | R3,721 ZAR | R3,704 ZAR | R3,902 ZAR | R3,902 ZAR | R3,902 ZAR | R3,787 ZAR | R3,523 ZAR | R3,342 ZAR | R3,622 ZAR | R3,556 ZAR |
| Avg. temp | 22°C | 22°C | 23°C | 24°C | 24°C | 26°C | 26°C | 27°C | 26°C | 26°C | 24°C | 23°C |
Frequently Asked Questions
What are the best places to stay in Kailua?
Stays in central Kailua let you explore vibrant shops and restaurants, while accommodations near Lanikai offer relaxed beach access. Both areas are frequently suggested for those looking for a local experience.
What are the best things to do in Kailua with kids?
Kailua Beach Park has gentle waves for swimming, and the Kalapawai Market is known for casual snacks and treats. Kayaking on the bay and exploring nearby nature trails are also frequently suggested for families.
What are some of the best things to do in Kailua?
Explore kayaking or paddleboarding in the calm bay, hike up to the Lanikai Pillboxes, and unwind at Kailua Beach Park. Kailua’s farmers' markets, local eateries, and bike paths are also frequently suggested.
How is the weather in Kailua?
Kailua has warm temperatures throughout the year, ranging from about 65–85°F (18–30°C). Rain is more frequent in winter and early spring, while summers are sunnier with less rainfall.
When is the best time to visit Kailua?
May through September has warmer temperatures around 70–85°F (21–30°C) and less rainfall, making it a popular time for beach outings. Late spring and early fall are often enjoyed for smaller crowds and local festivals.
What are the best places to visit in Kailua?
Frequently suggested spots in Kailua include the white sands of Kailua Beach Park, the scenic Lanikai Beach, and the Pillbox Hike for panoramic coastal views. The neighborhood also has inviting local markets and art galleries.
What are some hiking trails in Kailua?
The Lanikai Pillbox Hike is frequently suggested for its scenic coastal views and moderate climb. Locals also explore forested paths in nearby natural reserves, where you can experience native plants and ocean breezes.
What are some family activities we can do in Kailua?
Families can explore calm swimming beaches, rent bikes for easy paths, or visit local playgrounds in Kailua. Kayaking, visiting markets, or observing wildlife at Kawainui Marsh are also popular choices among visitors with children.
What are some of the best day trip ideas from Kailua?
Day trips around Kailua can include exploring lush botanical gardens, visiting the North Shore’s surf spots, or hiking in forested preserves. The area also has popular historic sites and cultural centers within easy reach.
Are there any pet friendly accommodations available in Kailua?
Many accommodations in Kailua are pet friendly, especially around central neighborhoods and residential areas. Parks and outdoor cafes make it convenient for guests traveling with pets.
What are some local tips for visiting Kailua?
Weekdays generally feel quieter at popular beaches, and early mornings are good for catching sunrise views from Lanikai. Remember to respect local customs, pack out what you bring, and use reef-safe sunscreen to protect marine life.
What is Kailua known for?
Kailua is known for its wide, sandy beaches, calm turquoise waters, and relaxed community vibe. The area has scenic hiking, local food spots, and opportunities to experience traditional Hawaiian culture.
What are the best hidden gems to explore in Kailua?
Kailua has quiet local beaches, shaded marsh trails for birdwatching, and small independent shops where you can explore local crafts. Consider wandering untouristed sections of Kailua Beach or the nearby Kawainui Marsh trail for a more laid-back experience.
What are the best foods to try in Kailua?
Kailua has fresh poke bowls, local plate lunches, and tropical fruit smoothies that are often recommended. Shave ice and pastries from neighborhood bakeries add to the area’s favorite flavors.
What should I bring for a trip to Kailua?
Pack light, breathable clothing, swimwear, reef-safe sunscreen, and a sun hat for comfort in Kailua's warm weather. If you plan to hike or explore nature, closed-toe shoes and a reusable water bottle are often recommended.
What is the nightlife in Kailua like?
Kailua has a relaxed nightlife scene with welcoming bars, laid-back dining spots, and venues that occasionally feature live music. Most nightlife is concentrated in town, and evenings often center around enjoying local flavors in a casual atmosphere.
What are the most popular events or festivals in Kailua?
Kailua frequently hosts street fairs, annual parade celebrations around holidays, and open-air art markets. Late spring and holiday weekends are often filled with local music, food, and craft events.
Are there family friendly vacation rentals in Kailua?
Kailua has many family-friendly rentals, often located near beaches or local parks. These options typically include amenities like kitchens, outdoor space, and easy access to nearby attractions.
All about Kailua
With stretches of powdery white sand beaches, two reef-protected lagoons, and temperatures kept on the comfortable side of cool by ever-present trade winds, it’s no surprise Kailua is no longer the secret destination guarded by seasoned island vacationers that it once was. Located on the windward side of Oahu on a peninsula overlooking the crescent-shaped Kailua Bay and the Koolau Mountain range, Kailua is beloved for its small beach town vibe — a mellow yin to Honolulu’s metropolitan yang, with only a 25-minute drive separating the destinations.
There’s also an increasing possibility of rubbing well-tanned shoulders with vacationing celebrities drawn to the same soft sand beaches and tranquil aquamarine waters delivering on the promise of paradise. In Kailua you can revel in a variety of water sports. Hikers have a range of challenging trails to choose from, some leading to breathtaking mountaintop views, others to such secluded mountain-fed pools as Maunawili Falls, along with a network of leisurely footpaths awaiting within the 830 acres of Kawainui Marsh.
What are the top things to do in Kailua?
Lanikai Beach
Lanikai Beach is often described as one of the world’s greatest beaches, and it’s easy to see why, with its breathtaking stretches of sand and ocean overlooking two nearby islets, the Na Mokulua. The waters here are typically calm, with a protected coastline buffered from windpowered waves thanks to a sizable reef offshore, making it one of the more swimmable spots on Oahu. These placid coastal waters are hard to beat — especially for kayaking and paddleboarding — tempting the more adventurous to paddle around those two offshore islands colloquially referred to as the Mokes.
Kawainui Marsh
Binoculars and a camera are a must while visiting Kawainui Marsh, the state’s largest protected wetlands, a sanctuary where many of Oʻahu’s endemic, endangered, and migratory birds, fish, and other aquatic life can be observed in their natural habitat. Travel by foot or by bike along a paved three-mile round path in a watershed that fed ancient Hawaiians with its abundance.
BookEnds
If you identify as a bibliophile and/or a lover of Hawaiian history, you might lose yourself once entering the door of this small neighborhood bookstore. BookEnds is filled with an extensive collection of Hawaiiana reflecting the islands’ history through photography, arts and crafts, architecture, and music.
Quick stats about vacation rentals in Kailua
Total vacation rentals
Explore 320 vacation rentals in Kailua
Nightly prices starting at
Kailua vacation rentals start at R659 ZAR per night before taxes and fees
Verified guest reviews
Over 10,690 verified reviews to help you choose
Family-friendly vacation rentals
190 properties offer extra space & kid-friendly amenities
Pet-friendly vacation rentals
Find 50 rentals that welcome pets
Vacation rentals with a pool
90 properties feature pools
Rentals with dedicated workspaces
160 properties have a dedicated workspace
Wi-Fi availability
320 of Kailua vacation rentals include wi-fi access
Popular amenities for guests
Guests love Self check-in, Beachfront, and Gym across Kailua rentals
4.9 Average rating
Kailua stays are highly rated by guests—averaging 4.9 out of 5!
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