Pet-friendly holiday rentals in Kailua

Waikiki Living

King Size 4 Post Bed, Sunrise on the surf, sunset on the beach, dinner at the top of Waikiki! Enjoy views of Ala Wai canal, Ko'olau mountains and the park on Aloha Drive from spacious lanais, including your own private one. Equipped with A/C, smart TV, microwave and a full kitchen to help make your stay in Waikiki magical! Gaming Chair with adjustable height desk, diffuser. Limited Parking sometimes available at the building for an additional $20/night. Inquire with me for availability!

Aloha Surf Condo - Private Deck - Pool - E-Bikes

Welcome to the Aloha Surf Condo at Kuilima Estates East, located within the Ritz-Carlton Turtle Bay Resort on Oʻahu’s North Shore. Our family uses the space ourselves, so we’ve furnished it with high-end pieces and thoughtful details that make every stay feel personal, comfortable, and cared for. Wake up to palm trees and golf course views, then walk or ride two RadRunner Premium E-Bikes to iconic surf breaks, beaches, resort restaurants, the pool bar, and Turtle Bay’s scenic trails.

Oahu Ocean View • Sleeps 14, Pool, Hot Tub, Beach!

Why guests love our cozy Makaha Valley home: Our home is right next to the resort-style pool, spa, and fitness center. Free parking for up to 4 cars (hotels charge $40–$100 per car) Full kitchen—cook your own meals and save on dining out 4-stage reverse osmosis drinking water—no need to buy bottled water Private backyard with a BBQ grill—perfect for outdoor dinners Washer and dryer in the garage—travel light! Gated community with pool, hot tub, gym, and scenic mountain views

Waikiki studio with balcony block from the beach

Value-packed studio with lots of amenities in this well-maintained and secure building in Waikiki. Centrally located in popular Waikiki--a short 5-minute walk to the best beaches and the upscale Ala Moana Shopping Mall and Kakaako districts and then come home and relax on your private lanai. Lots to do within easy walking distance from this studio, including many free tourist attractions, popular sightseeing tours, dining, theaters, beaches, and shopping galore.

Lani Kai Ocean View Villa Sleeps 12 Pool + Hot Tub

Welcome to Lani Kai Villa, your serene sanctuary in the heart of Mākaha Valley! This spacious retreat offers breathtaking mountain and ocean views from every room, blending luxury with serenity. Whether you're prepping local catches in the stylish chef’s kitchen or relaxing in the breezy, open-plan lounge, the home is designed for effortless social connection. Enjoy world-class beaches just minutes away and return to your private oasis to watch the sunset.

Paradise Found Makaha Valley Comfy Condo

MY CONDO IS NOT CLOSE TO Noisy/crowded downtown Honolulu!! , Roomy 2 bedroom Condo 1 min drive, 10 min walk from beautiful famous Waianae Surfing Beach. You can see the ocean from the lanai. Entire west side of condo has amazing views. The grounds are beautiful with lots great plants and animals to admire. There are 2 pools, 2 hot tubs, tennis courts, basketball court, and lots of walking/jogging trails. The unit has A/C and full size washer/dryer.

Tropical Kailua Retreat | Walk to Beach + Gym

Walk to one of Hawaii’s most beautiful beaches, explore Kailua by kayak or bike, and relax in your own tropical retreat. The Honu (Turtle) Suite at La Bella’s Bed & Breakfast offers privacy, comfort, and island charm just minutes from the beach. Enjoy a queen bed with luxury linens, air conditioning, a full kitchen, private bathroom, private entrance, and outdoor seating area surrounded by tropical gardens on Oʻahu’s beautiful Windward Coast.

Amazing Lanikai Beachfront Guest House!!

Bordering on Lanikai beach this Beautiful two story, three bedroom home has plenty of room to spread out. Panoramic view from Mokulua Islands to Kailua Bay, with breath taking Sun Rises. Taxes are included in the Daily Rate, Weekly Rate and Monthly Rates. There is a 30 day minimum stay. GE Tax 4.712% and Transient Tax 14.25% these are local and state taxes. TA# (PHONE NUMBER HIDDEN) (URL HIDDEN) GE# (PHONE NUMBER HIDDEN)

Private SPA, Sleep 12, Beach 5 min

Why guests LOVE our home? Whole house in Makaha Valley, Oahu's West Side, Leeward Coast — sleeps 12, private hot tub, backyard pool, mountain and ocean views, Makaha Beach 5 minutes away. All for under $100 per person per night. The less-touristed, more-local Hawaii. Perfect for multi-generational families and friend groups who want the whole house, not adjacent hotel rooms. Pets welcome. Top Airbnb 5% Guest Favorite home

DIAMOND ON DIAMOND HEAD

Located on the slope of Diamond Head, our apartment is at a walking distance of Waikiki beach, restaurants, nightlife, public transport. You’ll love my place because of the coziness, the location. I put a special attention on having the mattress spray monthly for bugs and also the apartment for insects. It is very important for me to offer a super clean, cozy, comfy and secure apartment. TA-182-790-8096-01

Newly Renovated * Waikiki Beachside Retreat

Aloha!! Your Newly Renovated Waikiki Retreat! Just steps from the vibrant Kūhiō Beach, this modern 1BR gem offers a serene escape for up to 4 guests. Dive into relaxation with nearby dining, shopping, and beach adventures. Perfect for those seeking a blend of comfort and Hawaiian excitement. Book your unforgettable getaway now!

60 second walk to Lanikai Beach. 2 Bedrooms w/ AC

Just a 60 second walk from world-famous Lanikai Beach, this unique 2-bedroom setup offers two private 1-bedroom studios. Each studio features its own kitchenette, dining area, sofa, private balcony, and full bathroom. Enjoy cool A/C, fast Wi-Fi, and thoughtful touches throughout. Relax, explore, and soak in the best of Lanikai.