Kailua Vacation Rentals

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Vacation Rentals in Kailua

Maui Schooner Resort
Outdoor pool, pool umbrellas
Maui Schooner Resort
3.5 star property
9.2 out of 10, Wonderful, (422)
"Our stay was wonderful. Beautiful resort and easy access to beach. Location was also good. "
Maui Schooner Resort
Sugar Beach Resort
Outdoor pool
Sugar Beach Resort
3.0 star property
8.6 out of 10, Excellent, (1010)
"Excellent location. Condo was excellent as well"
Sugar Beach Resort
Maui Sunset
View from property
Maui Sunset
3.5 star property
8.8 out of 10, Excellent, (391)
"loved the place and people"
Maui Sunset
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, (676)
"I liked the Price and the Laid Back feel"
Maui Beach Vacation Club
STHA-2017/0002 Across from Hana Bay
Sun loungers, beach towels
STHA-2017/0002 Across from Hana Bay
9.6 out of 10, Exceptional, (314)
"Absolutely loved the property...it was everything I expected."
STHA-2017/0002 Across from Hana Bay
Sugar Beach Resort - Maui Condo & Home
Outdoor pool
Sugar Beach Resort - Maui Condo & Home
3.0 star property
8.4 out of 10, Very Good, (506)
"You can’t have a better view at any other resort with beach access right out the door. Spent our 40th anniversary there and had the best time."
Sugar Beach Resort - Maui Condo & Home
10% Discount 7 Days or more! Kihei Top Floor Studio - AC, Clean, WiFi, Turtles!
Exterior
10% Discount 7 Days or more! Kihei Top Floor Studio - AC, Clean, WiFi, Turtles!
9.8 out of 10, Exceptional, (230)
"Kevin’s condo was the perfect beach getaway! The photos don’t do it justice—it’s even more charming in person. The pool is fantastic, large with a deep end, and immaculately clean. The bed is incredibly comfortable and brand new, ensuring a perfect night’s sleep. The condo is well-appointed, with everything we needed. We didn’t lack for kitchen utensils, beach gear, or towels—and the plush, large beach towels were a real treat. We had coffee every morning on the balcony overlooking an avocado...
The price is ￥14,241
￥55,312 total
includes taxes & fees
Oct 4 - Oct 5
10% Discount 7 Days or more! Kihei Top Floor Studio - AC, Clean, WiFi, Turtles!
Spacious Hawaiian home 50 steps from Sugar Beach!
Sun loungers, beach towels
Spacious Hawaiian home 50 steps from Sugar Beach!
8.8 out of 10, Excellent, (63)
"Fabulous spot for a family with kids (3, in our case). Quiet neighborhood just a few minutes away from great food and stores. Plenty of space in the house and a cute backyard to boot. Incredibly easy to walk to the beach (crosswalk and access path). Good spot for day trips north and west. A+"
Spacious Hawaiian home 50 steps from Sugar Beach!
Maui Vista – Maui Condo & Home
3 outdoor pools
Maui Vista – Maui Condo & Home
4.0 star property
8.6 out of 10, Excellent, (47)
"I enjoy this property because it is walkable to many shops, restaurants and the beach is right across the street. "
Maui Vista – Maui Condo & Home
Oceanside condo, full kitchen, ocean view. Fully renovated 2023
Beach nearby
Oceanside condo, full kitchen, ocean view. Fully renovated 2023
9.4 out of 10, Exceptional, (23)
"Wasn’t the cleanest but was great for us. A little more instruction on check in would have been great especially for initial parking. The beach equipment was an awesome addition."
The price is ￥17,262
￥50,786 total
includes taxes & fees
Oct 5 - Oct 6
Oceanside condo, full kitchen, ocean view. Fully renovated 2023
Groundfloor Beach Chic Condo W/ Lanai, Beach Across The Street! Nearby Dining
Exterior
Groundfloor Beach Chic Condo W/ Lanai, Beach Across The Street! Nearby Dining
10.0 out of 10, Exceptional, (13)
"We have a great time, property amenities, and location make it memorable!"
Groundfloor Beach Chic Condo W/ Lanai, Beach Across The Street! Nearby Dining
Private Cozy Studio walking distance to beaches, shops, restaurants and bars
1 bedroom, iron/ironing board, free WiFi, bed sheets
Private Cozy Studio walking distance to beaches, shops, restaurants and bars
10.0 out of 10, Exceptional, (80)
"This is a great location. The room is clean and the size is appropriate for 1-2 people if you primarily just need a place to sleep."
Private Cozy Studio walking distance to beaches, shops, restaurants and bars
2B/2B across from BEACH, S. Kihei, close dining & shopping, Pacific Shores
Pool
2B/2B across from BEACH, S. Kihei, close dining & shopping, Pacific Shores
9.8 out of 10, Exceptional, (145)
"Beautiful, efficient, well furnished unit. Steps were disappointment but managed for time we were there. Would do this unit again!"
The price is ￥28,914
￥72,634 total
includes taxes & fees
Sep 24 - Sep 25
2B/2B across from BEACH, S. Kihei, close dining & shopping, Pacific Shores
MAUI OCEAN VIEW 2 bed 2 bath with Air Conditioning
Sun loungers, beach towels
MAUI OCEAN VIEW 2 bed 2 bath with Air Conditioning
9.6 out of 10, Exceptional, (183)
"Our stay at Maui Ocean View in Kihei was awesome! The check in process was a breeze. The place had a gorgeous ocean view and was conveniently located. We were close enough to Kihei to walk downtown and enjoy the restaurants and shopping. The place was spotless and the extra beach supplies are a nice bonus. If you stay, make sure you walk across the street to watch the sunset and see the turtles. We would stay here again! "
MAUI OCEAN VIEW 2 bed 2 bath with Air Conditioning
Beautiful South Shore Maui 2B/2B Condo w Ocean Views Next to Pickle Ball Courts
Outdoor pool, a heated pool
Beautiful South Shore Maui 2B/2B Condo w Ocean Views Next to Pickle Ball Courts
9.6 out of 10, Exceptional, (56)
"Great place to stay, great location. Very clean with comfortable beds. Host Trisha is awesome and super helpful. Would stay again "
Beautiful South Shore Maui 2B/2B Condo w Ocean Views Next to Pickle Ball Courts
Great Rates - Clean and Cozy Condo!
Beach
Great Rates - Clean and Cozy Condo!
9.8 out of 10, Exceptional, (136)
"The location was just short enough of a drive from the airport - and close enough to many food locations, gas stations, and grocery stores. Clear check-in and out instructions with quick responses from the hosts."
Great Rates - Clean and Cozy Condo!
Ocean View Condo at Beachfront Resort w/ Lanai, AC, WiFi & Shared Pool/Hot Tub
Pool
Ocean View Condo at Beachfront Resort w/ Lanai, AC, WiFi & Shared Pool/Hot Tub
9.8 out of 10, Exceptional, (135)
"The host has thought of everything in this rental. Perfect beach beautiful pool . Would definitely stay there again A+++++"
Ocean View Condo at Beachfront Resort w/ Lanai, AC, WiFi & Shared Pool/Hot Tub
Evergreen Cottage @ Maui Adventure Villa
Property grounds
Evergreen Cottage @ Maui Adventure Villa
9.8 out of 10, Exceptional, (146)
"During my time in Maui it was a work trip and Johns property was the perfect spot to relax and recharge after a long days of work and adventure. The location was far enough to where there was no noise from the city but close enough to where it wasnt a burden to get to the beaches and stores. Will definitely stay again and recommend."
Evergreen Cottage @ Maui Adventure Villa
Fabulous Beachfront Property - Ground Floor Corner Unit Steps to the Beach!
Property grounds
Fabulous Beachfront Property - Ground Floor Corner Unit Steps to the Beach!
10.0 out of 10, Exceptional, (103)
"Condo was clean, comfortable and had everything we needed. The grill area is terrific and we used it 3 of the 6 nights we were there.The water is really churned up in that area so we never be had clear water. Also, at about 4 feet in the water there were rocks so bring water shoes. Overall I loved the place and would go back"
Fabulous Beachfront Property - Ground Floor Corner Unit Steps to the Beach!
Kihei Bay Surf 144 Tropical Hawaiian Style Condo, Beachy Theme New Split A/C
Fridge, microwave, oven, stovetop
Kihei Bay Surf 144 Tropical Hawaiian Style Condo, Beachy Theme New Split A/C
9.4 out of 10, Exceptional, (171)
"This property was great for us! Excellent location. Right across the street from the beach. Laundry on site. Clean and comfortable! Would definitely recommend staying here and would stay again myself."
Kihei Bay Surf 144 Tropical Hawaiian Style Condo, Beachy Theme New Split A/C
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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.
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Other types of properties in Kailua you may be interested in

Maui Beach Hotel
View from property
Maui Beach Hotel
3.0 star property
7.0 out of 10, Good, (1007)
"It was nice and calm. I liked that it was central. We were there to work so didn’t get to enjoy the room totally but very nice."
The price is ￥37,259
￥47,329 total
includes taxes & fees
Sep 24 - Sep 25
Maui Beach Hotel
Maui Seaside Hotel
Outdoor pool, open 9:00 AM to 7:00 PM, pool umbrellas, sun loungers
Maui Seaside Hotel
3.0 star property
8.6 out of 10, Excellent, (1157)
"The staff is always nice and go above and beyond to make our stay enjoyable! "
The price is ￥35,337
￥45,062 total
includes taxes & fees
Oct 22 - Oct 23
Maui Seaside Hotel
Kohea Kai Hotel Maui
Sundeck
Kohea Kai Hotel Maui
3.0 star property
8.6 out of 10, Excellent, (640)
"The room was cute, contemporary and clean. Our room looked out on to the water and mountains and the sunset was spectacular . "
The price is ￥34,848
￥41,107 total
includes taxes & fees
Oct 6 - Oct 7
Kohea Kai Hotel Maui
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.

Frequently asked questions

Can I find a vacation rental in Kailua?

Yes, there are vacation rentals near top sights in Kailua, or you can select a more secluded option if you're looking for relaxation.

What are some of the best vacation home rentals that Kailua has to offer?

STHA-2017/0002 Across from Hana Bay: This vacation home rental near Kailua is located in a rural location and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave. Make the most of the selection of games in this rental home to help you unwind.

What’s there to see and do in Kailua?

While exploring the area, visit family-friendly sights like Waikamoi Preserve, or get outside and enjoy nature at Twin Falls. In the larger area, you’ll find Garden of Eden Arboretum and Maui Garden Of Eden - Botanical Gardens & Arboretum.

What’s a vacation rental in Kailua like?

A vacation rental is a private property where you can stay for a few weeks or just a few days in Kailua. Vacation rentals feature extras such as laundry facilities and kitchens so your stay will be comfortable. If you're concerned about cleanliness, vacation rentals can provide a sense of seclusion away from shared hotel elevators and busy front desks while still allowing you a great travel experience. You'll also get more space in a vacation rental than in a hotel, which makes a vacation rental an attractive option for a small group gathering.