Kailua Vacation Rentals – Beachfront Homes and Island Cottages
Kailua vacation rentals deliver an authentic island experience on Oahu's scenic windward coast. Stay steps from world-famous beaches like Kailua Beach and Lanikai, with cozy cottages, modern family homes, and tropical escapes perfect for kayaking, hiking, and relaxing in paradise.
Island Living on Oahu's Windward Side
Kailua offers one of Oahu's most peaceful and picturesque vacation settings. Located just 30 minutes from Honolulu, this seaside town is known for its soft white sands, turquoise waters, and small-town charm. With no high-rises in sight, Kailua maintains a residential, beach-friendly vibe ideal for extended stays, family retreats, and romantic escapes.
Popular Activities in Kailua
From your vacation rental, enjoy quick access to outdoor adventures like:
- Kayaking to the Mokulua Islands
- Hiking the scenic Lanikai Pillbox Trail
- Swimming and sunbathing at Kailua Beach Park
- Shopping local boutiques and farmers markets
Key Features of Kailua Vacation Rentals
- Steps from Kailua or Lanikai Beach
- Private lanais, gardens, and outdoor showers
- Beach gear often included (chairs, boogie boards, bikes)
- Quiet neighborhoods perfect for remote work or extended stays
- Local eateries, cafés, and groceries within walking distance
Perfect For:
- Families needing space and beach access
- Couples seeking a romantic, secluded getaway
- Remote workers looking for inspiration and tranquility
- Visitors planning longer-term stays in a residential setting
Kailua is more than a beach destination-it's a lifestyle. Book a stay in one of our handpicked Kailua vacation homes and discover why travelers return to this corner of Oahu year after year.
Cozy Apartment In Sought After Neighborhood of Olomana!
NEW PHOTOS! One bedroom, one bath apartment in the quite neighborhood of Olomana. This cute apartment comes complete with a split system Split System AC unit, full bath and kitchenette. Rent is $2,000.00 and an additional $400.00 for All utilities including Cable,...
Leaf House: Lux Retreat w/ Pool, Ocean Views & Outdoor Living Near Lanikai
VIP Luxury Villas welcomes you to Leaf House, a serene three-story sanctuary set above Lanikai’s turquoise shoreline. Sophisticated architecture, panoramic Mokulua Island and mountain views, and over 7,000 combined square feet of indoor and outdoor living create an...
This 3 bedroom 2 1/2 bath townhouse is located in Lanikai. It is fully furnished and ready for move in. Gated Community with tennis courts , pool , hot tub and BBQ area. Views of the Koolau's and famous pillbox hike. Brazilian Teak flooring throughout, Wrap Around...
LANIKAI Plantation Cottage located only 3 houses from famous Lanikai Beach
This fully furnished 2-bedroom, 2-bath 2-story cottage is part of a private, gated, rambling plantation-style property. The 2nd level unit (not equipped for handicapped) catches the ocean breezes and comes with window A/Cs in all bedrooms, a living area, dining area,...
Lanikai Hillside Estate – Panoramic Luxury Above the Sea
Perched above the crystalline waters of Lanikai Beach, Lanikai Hillside Estate by Gather is a newly designed 5-bedroom, 5.5-bath luxury retreat with 6,295 sq ft of interior living plus expansive lanai spaces. Floor-to-ceiling glass, an infinity-edge pool, and panoramic...
LANIKAI SUITE - Spacious 1-BR 1-BA; located 3 houses from famous LANIKAI Beach
This fully furnished, turn-key, spacious 1-bedroom, 1-bath, is part of a private, gated, rambling plantation-style property. The 2nd LEVEL apartment catches the ocean breezes and comes with a window A/C in the bedroom, large living area and dining area. Street parking,...
Lanikai Oceanfront Home with Pool and Japanese-Style Hot Tub
Six bedroom ocean front home with pool and Japanese-style onsen (hot tub) is ideally suited for multi-family or multi-generational accommodation. Recent renovations and 2021 upgrades include split-air conditioning throughout the home, updated landscaping, new...
Suite By the Sea - a bright and sparkling Apartment
Welcome to our new private studio apartment, where comfort and convenience await you. This hidden gem boasts a well-equipped kitchenette, perfect for preparing your favorite meals. Nestled just a short stroll away from the breathtaking Kailua Beach, you'll find yourself...