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Holiday rentals in Kailua

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Top-rated holiday rentals in Kailua

Guests agree: these stays are highly rated for location, cleanliness, and more.

Superhost
Guest house in Kailua
Koolau Loft
Koolau Loft is our guesthouse with beautiful mountain views located in the heart of Kailua. The home has its own private entrance and is located up one flight of stairs. There is one covered parking spot reserved for our guests and more parking located on the street. The home is about a 15 minute walk to Kalama's beach park and a 5 minute walk to the center of Kailua Town, where there is a WholeFoods, Target, and multiple bars and restaurants. Note: there is no laundry on site for our guests.
Superhost
Guest suite in Kailua
Kailua Cottage
Charming attached cottage 2.5 blocks from famous Kailua beach. Totally private with own entrance, kitchen, bathroom, bedroom and living area. TV, WiFi and DVD player available to make your stay comfortable. Reserved parking for one car and access to your own private washer and dryer. Super comfy and cleaned using recommended COVID-19 guidelines. Beach towels, umbrella, and cooler for trips to the beach and an outdoor shower to rinse off when you return. Feel free to message with inquiries.
Individual Host
Superhost
Guest house in Kailua
Kailua Palm Studio. Walk to Beach! PERMITTED
Licensed, legal 90/BB-0002 short term rental. *not impacted by Bill 41 (2022) **NEWLY RENOVATED BATHROOM AND KITCHENETTE (at end of June 2023)** Peaceful retreat in desirable Kailua! An easy 8-10 minute walk to Kailua Beach. Private residence at the end of a quiet cul-de-sac with friendly neighbors. Rated #1 on Trip Advisor the past 10 years. Sister Unit: Kailua Pineapple Studio. Walk to Beach! PERMITTED. Property managed by Cynthia Rubinstein Real Estate, Inc. (License #RB-16858)
Individual Host

Stay near Kailua's top sights

Kailua Beach Park200 locals recommend
Boots & Kimo's Homestyle Kitchen51 locals recommend
Whole Foods Market370 locals recommend
Kailua Beach Adventures40 locals recommend
Buzz's Steakhouse136 locals recommend
Pillbox Hike178 locals recommend

Other great holiday rentals in Kailua

Superhost
Home in Kailua
The Red Ginger: Large 1 Bedroom
Individual Host
Superhost
Home in Kailua
Kailua Beach Park - 1 BR Cottage
Superhost
Guest house in Kailua
5 min Walk to famous Kailua Beach
Individual Host
Superhost
Guest suite in Kailua
The Perfect Escape
Individual Host
Superhost
Flat in Kailua
Beautiful Kailua Studio Near Beach
Individual Host
Superhost
Guest house in Kailua
Karibu Cottage in Beautiful Lanikai
Superhost
Flat in Kailua
Last-Minute Getaway Charming Studio in Prime
Professional Host
Superhost
Guest suite in Kailua
Quiet, Comfortable Home in Beautiful Kailua, HI
Individual Host
Superhost
Home in Kailua
Cozy Kailua Cottage
Superhost
Guest suite in Kailua
Modern studio, walk to the beach🌊
Superhost
Home in Kailua
The Pool House in Kailua with 3,200 sf, 6bed/4bath
Superhost
Guest house in Kailua
Beach Town Bungalow, Short Walk to Stunning Beach
Individual Host

Destinations to explore

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  2. United States
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  4. Honolulu County
  5. Kailua