Vacation rentals in Wailea

4.72 out of 5 average rating, 107 reviews

Home in Waikoloa Village

Wonderful Community Home Close to Famous Beaches

PeteRating, 5 stars2 months ago

Fantastic stay for our first time on big island. Keoni’s place was awesome. Updated everything,Tons of space, ac was great. Nice outdoor spaces for morning and evening. Also close 5-10 drive to shopping, grocery and restaurants. 15-20 minutes to best beaches on island. And honestly Spencer beach park was our favorite. 20 minutes, soft sand, small waves, tons of shade. Would stay at Keoni’s place again in a heartbeat. Mahalo for a great stay Keoni.

4.78 out of 5 average rating, 69 reviews

Home in Hilo

Ocean Front-Best Hilo Swim Lagoons. Sleeps 12.

KyleRating, 5 stars1 month ago

We really enjoyed our time in Hilo. Richard's house was a great space for our family. Definitely a chill, summer house vibe. It had everything we needed, and the view out the picture windows was stunning. We loved the huge tree in the front yard. We spent a lot of time at Richardson Beach. Snorkeling was really great. We would love to return.

4.95 out of 5 average rating, 131 reviews

Casa Chilin 2bd/2bth@Waikoloa Resort Walk To Beach

CathleenRating, 5 stars1 week ago

We had a wonderful stay! The accommodations were clean and comfortable, with everything we needed. The location was convenient to shops, restaurants, and groceries, and the view over the golf course was both lovely and serene. We would gladly stay again.

5 out of 5 average rating, 58 reviews

Villa in Waimea

Relaxing getaway at Golf Villas Mauna Lani Beach

CatherineRating, 5 stars2 weeks ago

We loved our stay! The condo was super clean, comfy, and had everything we could possibly need. The host was so friendly and easy to communicate with, which made everything even better. The amenities were awesome, and the grounds were beautiful — it really felt like a home away from home. The snorkeling at the beach club was one of our favorite activities - you just can’t beat swimming with sea turtles, octopus, and so many humuhumunukunukuāpuaʻa! We’d definitely stay here again and recommend it to anyone visiting Hawaii!

4.95 out of 5 average rating, 129 reviews

Newer Luxury Townhouse - Exceptional Value

RobRating, 5 stars1 month ago

Had our family of six stay for 11 nights during spring break. Lisa’s place is nicely decorated in the Hawaiian theme.The unit is located in the Hali’i Kai resort, an upscale community in Waikoloa area. The condo was exactly as described, and we were more than comfortable there. Quick walk to the beautiful pool and right next to the pickleball/tennis/basketball courts. We saw whales from the pool deck, and the location is a great launching place to explore Hawaii. Had beach chairs and umbrellas for the great beaches in the area. Anything you need and Lisa will have her designate help you. Would definitely recommend this condo, and would return in a heartbeat!

5 out of 5 average rating, 10 reviews

Apartment in Waimea

Serene Fairways @ Mauna Lani, Private Beach Club

CherylRating, 5 stars3 weeks ago

We loved our stay at the Fairways at Mauna Lani. The grounds were immacuately kept and we never had to worry about a thing. All of the items to use at the beach (cooler, umbrella, beach chairs, snorkels)were there and the pool is only a two minute walk away. We never had difficulty getting a spot at the pool for 4 of us. Everything was laid out for us and we had a preview of the guide that was left for us in the suite. It was very quiet in our unit and we felt like we had privacy but also were centrally located so that it wasn't a pain to get to anywhere else. Allyson was prompt to respond when we had any questions and was very accomodating. We would defintely recommend!

4.96 out of 5 average rating, 24 reviews

Home in Captain Cook

Kona Ocean Paradise with Pool

PatriciaRating, 5 stars1 week ago

We had a wonderful time during our stay. Ariya was super responsive and friendly. The house was clean and well equipped. Views are beautiful. The only drawback for us was that the pool was too deep to let the kids totally loose in as they couldn’t touch the bottom even in the shallow end. I will admit this is unlikely to be a problem for adults. The house is a bit of a drive from stores and towns/ some sites of interest, this was known to us and not an issue. Definitely need a car to get around, and a good idea to have groceries stocked!

Condo in Waikoloa Beach Resort

4.96 out of 5 average rating, 139 reviews

Enjoy lush tropical lifestyle in Waikoloa Resort

NatalieRating, 5 stars2 weeks ago

This was our favourite place that we’ve ever stayed in Hawaii! The condo was private and located in a great spot within the gated community. The lanai was a beautiful place to enjoy our meals, and had an excellent and private view of the pond and grounds outside. Inside was very clean and well stocked with all the cookware, toiletries, and beach supplies that we needed for our vacation. Our host even left us a very nice bottle of wine to welcome us on our first day. The pool and hot tub were clean and quiet, an excellent way to end the day. Sandy beaches including Hapuna, Kua Bay, and Mauna Kea were all located within a 10-20 minute drive from the door. The closest beach, A-Bay, was a 10-15 minute walk away and a great place to watch the sunset and see the turtles come up the beach to sleep for the night. Overall we would highly recommend this condo to anyone looking to visit Hawaii, and we would definitely stay here again on our next visit.

5 out of 5 average rating, 11 reviews

Home in Waikoloa Village

Lua Hoana - 3-BD Home with Ocean Views and Hot Tub

HeavenRating, 5 stars2 weeks ago

Our stay in Waikoloa Village was nothing short of magical! From the moment we arrived, we felt so welcomed and at home. The thoughtful touch of a welcome fruit basket and a handwritten note truly set the tone for a warm, personalized experience. One of the absolute highlights was meeting the resident guest Sweetie the black cat, what a delightful addition to the stay! Sweetie brought such charm and joy to our visit, making the whole experience even more memorable. The location is perfect, peaceful, beautiful, and close to everything we wanted to explore. But honestly, we could’ve stayed on the property the whole time and still felt like we were in paradise. The view from the master bedroom’s balcony was absolutely breathtaking, waking up to that each morning was a dream come true. We can’t recommend this place enough. Every little detail was perfect. We left relaxed, refreshed, and already talking about coming back. Thank you for such a wonderful experience!

4.81 out of 5 average rating, 423 reviews

Home in Keaau

HUGE! remodeled 270* view w/ocean sleeps 6!

Crystal TRating, 5 stars2 weeks ago

Mahalo Daryl: We had a wonderful time. Very comfortable. We wanted to bring to your attention the faucet in the shower is very loose, you may want to check on that. Also the main door they punched in the code and for some reason it didn't want to open. Eventually it did. I don't know if it runs on batteries but just wanted to share. Thanks have a wonderful week. Crystal

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Other great vacation rentals in Wailea

5 out of 5 average rating, 10 reviews

Home in Naalehu

EARLY check in and LATE checkout, WALLS OF GLASS

MunkhchimegRating, 5 stars1 month ago

I had a great stay at Mark’s place! He was very responsive and helpful throughout my visit. The space itself is beautiful—high ceilings, very spacious, and thoughtfully prepared. Everything was set up to make me feel right at home. I’d definitely stay here again and highly recommend it to others! Also, we stayed 4 nights and found local hidden gem places that we could enjoy. Location is very private and quiet which is loved it.

4.77 out of 5 average rating, 31 reviews

Home in Hilo

Hilo Paradise Home that has AC

Senthil RajaRating, 5 stars4 months ago

We felt like home. Adrianne was proactive in her communication and quick to respond. There were notes inside the house to ensure the guest uses the facilities correctly, I am ok with it. All the items shown in photos matches with what we got. It would be good, if part of the garage will be allowed to use by the guest. If I get a change, we will book it again and will recommend to friends.

Apartment in Waikoloa Village

4.71 out of 5 average rating, 7 reviews

NEW! Big Island Stay w Golf, Pickleball, Views!

KathyRating, 5 stars5 months ago

This condo is very quiet, overlooking the golf course and ocean. Nice sunsets. We really enjoyed the golfing (reasonable rate with the member's pass), and pickleball/tennis is very close ...beside the pool. Close by is a gym - which had a big workout area and daily cardo classes. Also - a very good grocery store nearby. The condo was well set-up for the two of us. particularly helpful were the beach chairs, umbrellas, etc. We spent many afternoons visiting different beaches along the Waikoloa coast. Some were a few miles away, others about 15 min drive. The guidebook in the condo was very helpful.

5 out of 5 average rating, 24 reviews

Home in Captain Cook

2bd Mt. Hideout Near Big Is. Treasures +Disc Golf!

KobbiRating, 5 stars2 months ago

we spent a week in Matthew's place and would be happy to come back on a future trip. The house is large and full of good stuff - games, kitchen stuff, and more. The immediate surroundings are beautiful as is the view from the porch. Matthew is extremelya helpful and thoughtful. He really cared that we will enjoy our stay. Indeed a five star host. Ocean view is about 90 mins from Kona airport. I suggest not arriving at dark the first time - the area is dark and following the maps app we entered one driveway too early - backing up at darkness was scary. Make sure to follow Matthew's instructions and not just the app. The driveway to the house is not fully paved. However, after you see the way once at daylight it becomes easier. overall, we could use the place as a most comfortable place from which we could reach volcano national park several times and many beaches. it was good to be back to a cosy place at night. We would be happy to do this again!

4.93 out of 5 average rating, 100 reviews

Spectacular Ground Floor Condo Sleeps 5

AngelaRating, 5 stars1 month ago

We had a very nice stay at Martin's place. Home was clean and spacious, we had everything we needed as if we were at our own house. The location was great, close to the beach, shopping and restaurants. We are so glad we chose this over the hotels. Thank you for sharing your lovely home.

4.95 out of 5 average rating, 83 reviews

Fabulous Waikoloa Beach Resort 3BR Colony Villas

AustinRating, 5 stars3 months ago

Great communication, very comfortable accommodations and in a great spot for all the things you would want to do on the big island.

4.98 out of 5 average rating, 57 reviews

Condo in Waimea

Exquisite Sunsets and Beaches at Mauna Lani Resort

SaraRating, 5 stars1 week ago

My husband and I just returned from a 5 week stay in this 3 bedroom condo. It was perfect from start to finish. Allyson was the best host we have ever worked with. Her ease of communication and her response time is amazing. The condo is exactly like described. Every room felt fresh, free of clutter, clean and with great furnishings. The back patio is a dream - we spend mornings out there with coffee and almost every evening meal was at the back table just before sunset. The condo pool area during our 5 weeks was relatively quiet every day. We were always able to find lounge chairs and the surroundings were immaculate. We hope to return again next year!