Discover a selection of vacation rentals in Downtown Kailua that are perfect for your trip. Whether you're staying in a vacation rental with family or friends, you'll find the amenities you need and want, such as WiFi and cable TV. What you'll find is a rental to meet everyone's needs, including options that are accessible or non-smoking.
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Loading More information about Luxurious five-bedroom modern retreat, opens in a new tab More information about Award Winner - Hawaii's Hidden Hideaway - Bed and Breakfast, opens in a new tab More information about Less than 1 min walk to Kailua Beach- NUC#1990/NUC-1760, opens in a new tab More information about PRIVATE BEACHFRONT RENTAL, opens in a new tab More information about Kailua Town & Kailua Beach, opens in a new tab More information about Just steps from the sand—enjoy a pool, hot tub, bikes, beach gear & more!, opens in a new tab
Find the best place to stay - Downtown Kailua
Luxurious five-bedroom modern retreat
Sleeps 18 · 5 bedrooms · 4 bathrooms
8.88.8 out of 10
Excellentexcellent
5 reviews(5 reviews)
Award Winner - Hawaii's Hidden Hideaway - Bed and Breakfast
Sleeps 3 · 2 bedrooms · 3 bathrooms
9.29.2 out of 10
Wonderfulwonderful
113 reviews(113 reviews)
Less than 1 min walk to Kailua Beach- NUC#1990/NUC-1760
Sleeps 5 · 2 bedrooms · 2 bathrooms
9.29.2 out of 10
Wonderfulwonderful
168 reviews(168 reviews)
PRIVATE BEACHFRONT RENTAL
Sleeps 2 · 1 bedroom
1010 out of 10
Exceptionalexceptional
185 reviews(185 reviews)
Kailua Town & Kailua Beach
Sleeps 6 · 3 bedrooms · 2 bathrooms
9.69.6 out of 10
Exceptionalexceptional
53 reviews(53 reviews)
Just steps from the sand—enjoy a pool, hot tub, bikes, beach gear & more!
Sleeps 5 · 2 bedrooms · 2 bathrooms
9.69.6 out of 10
Exceptionalexceptional
229 reviews(229 reviews)
Top rated rentals - Downtown Kailua

Kailua Cottage
Kailua Cottage
10.0 out of 10, Exceptional, 1 review
10
Exceptional
1 review
"The Kailua Cottage was exactly as described. Located blocks from the beach with a ton of amenities. It felt like a home away from home. My favorite part was morning coffee on the patio. Christine and Steven were top notch hosts. Both helpful and responsive without being intrusive. I would highly recommend for a vacation stay or a longer stay for a military PCS. "
"The Kailua Cottage was exactly as described. Located blocks from the beach with a ton of amenities. It felt like a home away from home. My favorite part was morning coffee on the patio. Christine and Steven were top notch hosts. Both helpful and responsive without being intrusive. I would highly recommend for a vacation stay or a longer stay for a military PCS. "
sean d.

Premier Host
LOVE this place!
LOVE this place!
10.0 out of 10, Exceptional, 26 reviews
10
Exceptional
26 reviews
"Bright, clean, and comfy! We loved this Bungalow on so many levels. (Yes, it is up a flight of stairs, a treehouse for certain!) The Banyan Tree is epic! This location was perfect for our daily beach visits and perfect sunrise views from the gorgeous, steps away, Kailua Beach! The Host made our visit here effortless and we would highly recommend staying here. We appreciated the relaxed local vibe experience, the nearby Thursday Farmers Market and the Saturday Outrigger Canoe Club races at...
"Bright, clean, and comfy! We loved this Bungalow on so many levels. (Yes, it is up a flight of stairs, a treehouse for certain!) The Banyan Tree is epic! This location was perfect for our daily beach visits and perfect sunrise views from the gorgeous, steps away, Kailua Beach! The Host made our visit here effortless and we would highly recommend staying here. We appreciated the relaxed local vibe experience, the nearby Thursday Farmers Market and the Saturday Outrigger Canoe Club races at...
Pam R.

Great spot for downtime in Kailua
Great spot for downtime in Kailua
10.0 out of 10, Exceptional, 118 reviews
10
Exceptional
118 reviews
"Very pleasant room and the property is beautiful. Having beach towels, chairs, and boards was a great plus with Kailua beach a ten minute walk away. Hosts were very friendly and helpful, immediately fixed a small issue that came up. We’ll definitely stay here again if we get the chance to visit this wonderful town again."
"Very pleasant room and the property is beautiful. Having beach towels, chairs, and boards was a great plus with Kailua beach a ten minute walk away. Hosts were very friendly and helpful, immediately fixed a small issue that came up. We’ll definitely stay here again if we get the chance to visit this wonderful town again."
Mike S.

Kailua's key to a perfect vacation!
Kailua's key to a perfect vacation!
10.0 out of 10, Exceptional, 46 reviews
10
Exceptional
46 reviews
"We had an amazing stay in Kailua. We loved the area that had a beautiful beach nearby (walking distance), many shopping and food options with a small town feel, and very responsive and helpful hosts. Driving to all the other attractions on the island were only 30 minutes to an hour away. The lanai was a favorite spot to sit and relax enjoying the plumeria and other beautiful plants and birds. Rick and Nancy provided beach chairs, bicycles, cooler, and a grill in addition to a well furnished home...
"We had an amazing stay in Kailua. We loved the area that had a beautiful beach nearby (walking distance), many shopping and food options with a small town feel, and very responsive and helpful hosts. Driving to all the other attractions on the island were only 30 minutes to an hour away. The lanai was a favorite spot to sit and relax enjoying the plumeria and other beautiful plants and birds. Rick and Nancy provided beach chairs, bicycles, cooler, and a grill in addition to a well furnished home...
Norma P.

Premier Host
Best vacation rental
Best vacation rental
10.0 out of 10, Exceptional, 23 reviews
10
Exceptional
23 reviews
"Tobi and Yvonne the rental hosts were great! To start we were traveling with an infant and they let us check in early so we could get her situated. The cottage was very clean, updated and comfortable with all the amenities and more. Great location and very welcoming couple. We definitely will be back."
"Tobi and Yvonne the rental hosts were great! To start we were traveling with an infant and they let us check in early so we could get her situated. The cottage was very clean, updated and comfortable with all the amenities and more. Great location and very welcoming couple. We definitely will be back."
debra p.

Premier Host
Paradise Found
Paradise Found
10.0 out of 10, Exceptional, 29 reviews
10
Exceptional
29 reviews
"Having vacationed on other islands in years past, we decided to visit Oahu without the congestion of Honolulu and Waikiki, while still maintaining a beautiful beachfront locale. Our Kailua Beach Lofty Bungalow did not disappoint! Vicki and her husband were wonderful hosts, and provided my wife and I a beautifully designed bungalow, complete with a private patio, an outdoor shower (which we used exclusively), in an intimate setting canopied under a 300 year old Banyan Tree! The accommodations...
"Having vacationed on other islands in years past, we decided to visit Oahu without the congestion of Honolulu and Waikiki, while still maintaining a beautiful beachfront locale. Our Kailua Beach Lofty Bungalow did not disappoint! Vicki and her husband were wonderful hosts, and provided my wife and I a beautifully designed bungalow, complete with a private patio, an outdoor shower (which we used exclusively), in an intimate setting canopied under a 300 year old Banyan Tree! The accommodations...
Todd W.

Fantastic stay at Enchanted Lake in Kailua!
Fantastic stay at Enchanted Lake in Kailua!
10.0 out of 10, Exceptional, 101 reviews
10
Exceptional
101 reviews
"Marcie’s apartment is absolutely perfect for a stay in Kailua and Kailua is a perfect place for a stay in Oahu (opposed to the hustle and bustle of the Honolulu’s surroundings). Its view is spectacular and neighborhood very familiar and quiet. The kitchen is very well equipped and we used a lot! It’s very close to Kailua and Lanikai beaches, Kailua center, grocery stores and half way to the North Shore and Honolulu! Perfect in all aspects, would love to come back!"
"Marcie’s apartment is absolutely perfect for a stay in Kailua and Kailua is a perfect place for a stay in Oahu (opposed to the hustle and bustle of the Honolulu’s surroundings). Its view is spectacular and neighborhood very familiar and quiet. The kitchen is very well equipped and we used a lot! It’s very close to Kailua and Lanikai beaches, Kailua center, grocery stores and half way to the North Shore and Honolulu! Perfect in all aspects, would love to come back!"
Adriana C.
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