Search Vacation Homes in Kailua

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Compare 106 Vacation Homes in Kailua with updated reviews, rates, and availability.

STHA-2017/0002 Across from Hana Bay
Sun loungers, beach towels
STHA-2017/0002 Across from Hana Bay
9.6 out of 10, Exceptional, 290 reviews
"This unit was an oasis away from our home. So well outfitted yet had the charm of a truly Hana home. We especially loved and spent most of our time on the front porch relaxing before and after each day's excursions!"
STHA-2017/0002 Across from Hana Bay
Kaiholo Hale
Beach nearby
Kaiholo Hale
3.0 star property
9.4 out of 10, Exceptional, 179 reviews
"This was an excellent trip. I would recommend this Plato any one! The hosts were very accommodating to our late flight out. "
Kaiholo Hale
Fisher's Hana Bay Hale, Across from Hana Bay
Sun loungers, beach towels
Fisher's Hana Bay Hale, Across from Hana Bay
9.6 out of 10, Exceptional, 308 reviews
"We loved this place! Very homey and cute. Very easy to walk into town with beautiful views. The property has gorgeous landscaping and is well taken care of."
The price is $195
$397 total
includes taxes & fees
Jun 28 - Jun 29
Fisher's Hana Bay Hale, Across from Hana Bay
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Special quiet, romantic, cozy home in a special place, Heavenly Hana. Lucky you!
Smart TV, Netflix, DVD player, books
Special quiet, romantic, cozy home in a special place, Heavenly Hana. Lucky you!
9.8 out of 10, Exceptional, 192 reviews
"This house is even better than the listing makes it look. Clean & comfortable with a huge beautiful yard. The outdoor patio is also great with comfortable furniture & everything you could possibly ask for. We would highly recommend this house to anyone looking for a clean comfortable place to stay near Hana. We were very happy with everything and will definitely book this house again."
The price is $300
$598 total
includes taxes & fees
Jun 2 - Jun 3
Special quiet, romantic, cozy home in a special place, Heavenly Hana. Lucky you!
Spacious Hawaiian home 50 steps from Sugar Beach!
Beach | Sun loungers, beach towels
Spacious Hawaiian home 50 steps from Sugar Beach!
8.8 out of 10, Excellent, 58 reviews
"Thai is a fabulous location. Truth about how close to beach! Our only issue was there was no table to sit at inside. No table for cards or coffee. Outside wasn’t always appropriate. Major construction going on next door was an eyesore…"
Spacious Hawaiian home 50 steps from Sugar Beach!
Private lush 2 Acre Mountain Home Maui Permitted#STMP 2013-0001 many amenities
Exterior
Private lush 2 Acre Mountain Home Maui Permitted#STMP 2013-0001 many amenities
10.0 out of 10, Exceptional, 198 reviews
"We all (8 of us) liked the property. It had everything you need for cooking etc. Very nice appointments. We all enjoyed our stay there."
Private lush 2 Acre Mountain Home Maui Permitted#STMP 2013-0001 many amenities
Beautiful Home in paradise!
Beach
Beautiful Home in paradise!
9.6 out of 10, Exceptional, 149 reviews
"Nice"
Beautiful Home in paradise!
Spacious Maui Beach House, Private Pool, AC, Sleeps 6
Beach nearby, sun loungers, beach towels
Spacious Maui Beach House, Private Pool, AC, Sleeps 6
10.0 out of 10, Exceptional, 37 reviews
"My wife and I just enjoyed our third visit to this property, and once again it is was just perfect. This property is a gem. The hosts are great and we will keep going back. Highly recommended."
Spacious Maui Beach House, Private Pool, AC, Sleeps 6
Maui Sunset Resort A102 - Aloha Mai, Remodel, Ground floor, 1BR/2BA, Sleeps 5, A
Pool
Maui Sunset Resort A102 - Aloha Mai, Remodel, Ground floor, 1BR/2BA, Sleeps 5, A
9.6 out of 10, Exceptional, 84 reviews
"Clean, modern condo on a great location. Beautifully kept grounds. There’s a putting green right outside the back door and it’s only a few more steps to the pool and beach. Easy and open parking. Air conditioners worked great and we were never hot. Everyone we met at the resort was very friendly. Looking forward to returning soon. Highly recommend."
Maui Sunset Resort A102 - Aloha Mai, Remodel, Ground floor, 1BR/2BA, Sleeps 5, A
Stunning Koa Resort 3bd Villa w/ private Jet Spa
TV, offices
Stunning Koa Resort 3bd Villa w/ private Jet Spa
Stunning Koa Resort 3bd Villa w/ private Jet Spa
Tropical Gated Oceanfront Estate, Pool, Privacy, and huge ocean view on 2/3 acre
On the beach, sun loungers, beach towels
Tropical Gated Oceanfront Estate, Pool, Privacy, and huge ocean view on 2/3 acre
9.8 out of 10, Exceptional, 178 reviews
"We loved our stay here! Our family of 17 had plenty of room and the house is very well stocked! We enjoyed being across from a great beach and absolutely loved having our own pool. We would stay here again in a heartbeat!"
Tropical Gated Oceanfront Estate, Pool, Privacy, and huge ocean view on 2/3 acre
Stunning Beach Front Townhouse
Property grounds
Stunning Beach Front Townhouse
10.0 out of 10, Exceptional, 79 reviews
"Property is a little dated but location and view more than make up for that drawback. You'd be hard pressed to get any closer to the water. Pool was an added bonus. Kitchen was well equiped with everything you would need to cook meals. Overall, we really enjoyed our stay here"
Stunning Beach Front Townhouse
Hana Bay Oceanfront Cottage
Aerial view
Hana Bay Oceanfront Cottage
10.0 out of 10, Exceptional, 6 reviews
"My husband and I spent two weeks in Maui for his birthday and to get some R&R. Staying in Hana was at the top of our vacation list, and we spent quite a bit of time looking for top-notch lodging. This cottage was absolutely spectacular! The unobstructed views of the beach, the sounds of the surf, and the quiet neighborhood were beyond our expectations! We spent a lot of time on the lanai just watching the waves crash on the beach, reading our books, eating homemage meals.... it was so...
Hana Bay Oceanfront Cottage
PRIVATE RESORT near Cove Park in Kihei. Sleeps up to 18 in TWO separate houses!
Beach nearby
PRIVATE RESORT near Cove Park in Kihei. Sleeps up to 18 in TWO separate houses!
9.8 out of 10, Exceptional, 14 reviews
"This place was perfect for our family of 13. Kihei was the perfect place to stay at on Maui - it was close to everything, and Kihei itself was beautiful and had plenty of amazing food options. Our host was so friendly and accommodating. We didn’t need much from him because we had everything we could possibly need when we arrived. I wish we didn’t have to leave we could have stayed there forever!"
PRIVATE RESORT near Cove Park in Kihei. Sleeps up to 18 in TWO separate houses!
Haiku Hale - 3 Bedroom Maui Getaway!
3 bedrooms, free WiFi, bed sheets
Haiku Hale - 3 Bedroom Maui Getaway!
10.0 out of 10, Exceptional, 3 reviews
"Our family of five (all adults) couldn't have been more pleased with this property! The house was clean, well supplied/equipped, and very comfortable. The landscaping was beautiful. Having the grill available made for great outdoor meals. We took advantage of the short walk into town at least a couple times daily, and the distance to beaches and other activities was quite convenient. We're hoping this property will be available for our next trip to Maui! Thank you, Jorma, for helping us to...
The price is $495
$990 total
includes taxes & fees
Jun 3 - Jun 4
Haiku Hale - 3 Bedroom Maui Getaway!
HOUSE.. ON THE BEACH MAUI
Fridge, microwave, oven, stovetop
HOUSE.. ON THE BEACH MAUI
9.8 out of 10, Exceptional, 140 reviews
"This property was just as listed and even better! Great communication with our host Brian, great location to access community and restaurants and even greater natural environment! One night we counted 36 turtles on the beach...mornings on the deck were glorious. The house is stocked with more than we expected and plenty of room for all of us. We couldn't have picked a better place."
HOUSE.. ON THE BEACH MAUI
Modern 3 Bedroom Tropical Kihei Home Near Beach
Beach nearby
Modern 3 Bedroom Tropical Kihei Home Near Beach
9.8 out of 10, Exceptional, 133 reviews
"Lovely home in Kihei, well appointed, modern and comfortable. Easy walking distance to beaches, restaurants and the food trucks at South Maui Gardens!"
Modern 3 Bedroom Tropical Kihei Home Near Beach
Sugar Beach Resort Condo w/ A/C, Shared Pool/Hot tub-Surf, Bike, Golf, More
Pool
Sugar Beach Resort Condo w/ A/C, Shared Pool/Hot tub-Surf, Bike, Golf, More
9.0 out of 10, Wonderful, 33 reviews
"Excellent condo with all necessary amenities for our stay. Very nice location, and on a quiet beach."
Sugar Beach Resort Condo w/ A/C, Shared Pool/Hot tub-Surf, Bike, Golf, More
Sugar Beach Resort condo with ocean view, AC - surf, bike & golf
Pool
Sugar Beach Resort condo with ocean view, AC - surf, bike & golf
8.8 out of 10, Excellent, 37 reviews
"Things we really enjoyed: fantastic location only 15 mins from airport; ocean view from our patio door; literally steps from the beach (loved our walks on the beach in the early morning ); updated kitchen with large island, nice parking spot , air conditioning and very quiet area. Things to improve the stay: screen door would not fully close and because of the little flies we always had to keep patio door always closed; need for a dresser or luggage rack to place suitcase. Didn’t mind the bed or...
Sugar Beach Resort condo with ocean view, AC - surf, bike & golf
Hale Kai O Kihei Condo w/ Shared Pool, Ocean View-Beaches and Beyond
Property grounds
Hale Kai O Kihei Condo w/ Shared Pool, Ocean View-Beaches and Beyond
9.0 out of 10, Wonderful, 76 reviews
"This condo was amazing, and just the right size for my friend and I. The view is amazing, we watched whales breech each morning from the balcony. The amenities in the condo made it feel like home, and the location was quiet, but still close to shops and dining. The pool is lovely, and the property is very clean and well maintained. The beach was not crowded and it was nice to be able to relax, while being steps from the condo. I would stay at this condo again and hope to return soon! Thank you!"
Hale Kai O Kihei Condo w/ Shared Pool, Ocean View-Beaches and Beyond
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See all available properties in Kailua
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Other property types in Kailua

Maui Beach Vacation Club
Suite, 2 Bedrooms | Living area | TV
Maui Beach Vacation Club
2.5 star property
8.2 out of 10, Very Good, 622 reviews
"Loved this place"
Maui Beach Vacation Club
Sugar Beach Resort
Outdoor pool
Sugar Beach Resort
3.0 star property
8.6 out of 10, Excellent, 984 reviews
"Nice and clean. I don’t like the shower."
Sugar Beach Resort
Maui Schooner Resort
Outdoor pool, pool umbrellas
Maui Schooner Resort
3.5 star property
9.2 out of 10, Wonderful, 360 reviews
"Good place"
Maui Schooner Resort
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Kailua Vacation Homes information

Number of reviews
1,914
Accommodation
106 Vacation Homes
Lowest Price
$195
Highest Price
$495

Recent reviews of Kailua hotels
Expedia verified reviews

Maui Sunset

Maui Sunset

5/5 Excellent
"The access to the beach was wonderful! We watched the gorgeous Maui Sunset every night we were there from the edge of the beach in the beach chairs provided by the unit. The balcony was roomy and also had magnificent views of the bay. There was plenty of space for the 5 of us! Easy access to food, shopping, and other beaches and activities! The concierge at the pristine pool was super helpful and booked us a very memorable snorkeling tour. Really was all you could ask for at a very affordable price! It was perfect for our family and budget. We highly recommend Maui Sunset! "
A verified traveler stayed at Maui Sunset
Posted 1 day ago
Maui Sunset