Enjoy Oahu South Shore by driving along the island’s southern coast which spans from Hawaii Kai to Moanalua. Formerly the battlegrounds of island chieftains, it became a progressive shipping port in the 1850s. By the 1930s, it became a multiracial Pacific port that covers Honolulu, Pearl Harbor, Waikiki, Ala Moana, Diamond Head, and University of Hawaii & Manoa. Appreciate the breathtaking scenery of sea cliffs and beaches in a background of blue ocean and lush colorful vegetation as you drive from Waikiki and its astounding Kuilei Cliffs then through the high-class neighborhood of Kahala with its manicured gardens, splendid homes, and the fine sands of Waialae Beach known for water sports. Kalanianaole Highway is lined with several beach parks like Hanauma Bay’s calm waters, best for picnics and snorkeling. For a place to stay, check out our list of the best Vrbo accommodations in Oahu South Shore, Hawaii. We’ve listed them below so book them now.
We handpicked these listings carefully, considering (wherever possible) Superhost status, recent guest reviews, location, accommodation type, prices, availability of dates, decor, and amenities. The image galleries get refreshed with the latest updates regularly. They were last updated on July 15, 2022.
1. Lovely oceanfront condo (from USD 729)
This lovely eight-floor condo is in an oceanfront building near the beach, bar, and restaurants. The luxurious interiors are decorated with designer furniture and high-class appliances. It has an elegant dining table for six, an open-plan kitchen with a breakfast counter, a cozy living room with cable TV and free internet, and a furnished balcony overlooking the pool. Three big bedrooms sleep a total of six guests, with enough beds that have thick cushions and silky linens. The three bathrooms have either an enclosed shower or a bathtub with separate toilets and basin sinks. Enjoy laundry facilities, air-conditioning, wheelchair access, and free parking during the required five to seven nights stay.
Top guest reviews
Amenities & Room:
:) - and the kitchen was well-stockedthe kitchen was Anything & everything needed to cook was stocked in that kitchen howeverThe unit itself is amazingtook our luggage to the roomWe had 3 master bedrooms with their own bathroomCleanliness:
All amenities were clean and in great conditionWe like this side of Oahu because it's remote and quiet vsWe highly recommend that others take advantage of your "little piece of paradise" and we hope to return one dayThe beds pillows and linens were soft and comfortableThe view was beautiful and the staff were very helpfulHost:
He met us at the check inShe was always friendly and helpfulThe owner/manager Thu was so helpful and made all transactions so simpleand the owner was the most attentive efficient and gracious owner we have ever worked with on a vacation rentalGreat location beautiful unit friendly staffRead more reviewsLocation:
There are a few places to dine in the area with Roy's being within walking distanceWe loved the lagoons and we enjoyed the ability to walk to different restaurants for dinner and we also enjoyed grilling for ourselves a few nightsKailua beaches are easy drivesFor a lovely Hawaiian experience away from the crowds pumped in music bird noises and pyrotechnics (at the Aulani)It is about 40 minutes from Honolulu
2. Luxurious penthouse villa (from USD 525)
This penthouse villa is in a beachfront resort near the beach, golf greens, outdoor pools, and koi ponds. To access the villa, you have to ride a semi-private elevator to the eleventh floor. The unit has resort-like interiors with relaxing wicker furniture decorating the living room, dining area, and open kitchen. A covered lanai overlooks the lush garden and beach scenery. Two spacious bedrooms furnished with a king bed and two twin beds sleep four guests comfortably. The rooms have air-conditioning, cable TV, iHome, free internet, and wide windows with awesome views. Two ensuite bathrooms have vanity sinks, bathtubs, walk-in shower, and free bath essentials. Stay for six to seven nights with access to the resort facilities like the outdoor pool, gym, and barbecue area.
Top guest reviews
Amenities & Room:
there was a very comfortable bed in the master bedroom which i appreciate since i have back problemsCleanliness:
(though i wasn’t there a family member was)the condo was clean and ready to move insuper clean well appointed and spacious with amaizing sea viewsHost:
staff on site was amazingowners were fantastic and everything was seamlessextremely friendly staff as we walked the grounds and everyone greeted us with alohasfully appointed and equipped and the service manager was attentive and friendlythe host jeff was very hospitable really helpful and quickly responded to my queriesRead more reviewsLocation:
we loved the locationbeautiful location perfect to walk to the coves for swimming and snorkelingfabulous location on the west side of oahuthe villa/condo was great right on the lagoon with only a 5 minute walk standing in betweenwe felt incredibly fortunate to land this place and look forward to many more returns
3. Asian-inspired villa (from USD 485)
The unique Asian-inspired décor and interiors of this villa guarantee a luxurious stay for six guests. The villa has a spacious lanai where guests can enjoy al fresco dining with a feel of the Hawaiian breeze. The fully stocked open kitchen is designed by Roy Yamaguchi, with a breakfast nook and tiny dining table on the side. The two bedrooms have bamboo bedframes with king- and queen-sized beds for cozy sleeping and access to a furnished terrace. The unit has a lounge with satellite TV, free internet, air-conditioning, heating, and two private bathrooms with a tub and shower. The property is near Monkey Pod restaurant and has grill areas, hot tubs, pools, and free parking for guests to enjoy.
Top guest reviews
Amenities & Room:
The condo looks just like the pictures postedand I thought the master bedroom was a nice size and was very comfortable to sleep inwater toys - to the community potIt does overlook the parking lotso basically the whole glass wall of the kitchen and part of the sitting room open up to the outsideCleanliness:
The villa was beautiful and very neatWe loved both bathrooms which had very deep bath tubs perfect for soaking the day awayThe lanai is super relaxing and enjoyableHost:
Lisa gave us so much helpful information about the areaShe sent me a very detailed list of all attractions and places to eatThe owner was great to work with and very helpfulshe provided some very detailed infoLisa was very helpful with helping me plan the tripRead more reviewsLocation:
Its in a very nice locationThere are plenty of places within walking distance to get in some beach timeEntire process was incredibly easyThe best luau was a few blocks away which is a must see if you're visiting the island of Oahu for the first timeWe would not want to stay anywhere else
4. Gorgeous penthouse with panoramic views (from USD 500)
Have a most pleasant stay in this ninth-floor penthouse in a beach resort in Kapolei, for at least six nights! The spacious unit sleeps eight guests with three huge bedrooms with a king, queen, and two single beds. The rooms are equipped with air-conditioning, free internet, and cable TV. The master suite has a balcony with breathtaking views. The living room is cozy for watching TV, with sliding doors that open to a furnished lanai with sweeping ocean views. The six-seater table is for casual dining and the kitchen island works as a breakfast nook. The fully equipped kitchen has impressive stainless steel appliances. The two private bathrooms have bathtubs, vanity sinks, and a separate toilet and shower. Pool access, elevator access, and free parking are provided.
Top guest reviews
Amenities & Room:
The kitchen has everything you need and the beds are very comfortableHad a great time Resort staff and amenities were outstanding Loved the view from the condo although we felt the living room and bedroom furniture could use some updatingThe condo is everything that was promised and so much moreThe pictures DO NOT do itBeds and pillows were comfortableCleanliness:
The whole resort was kept very cleanThe room was clean when we arrived and the staff was friendlyThe pools and beach are very lovelyHost:
Nice property very accommodating for all of us Very clean and spaciousWe were definitely sad to leave but excited to hopefully be visiting again soonMike was easy and great to work with and was very quick to respond to any questions We would highly recommend and would definitely stay again Thanks for a wonderful experienceMike the owner is very responsive and is gunuine in his desire to make your stay enjoyableVilla was well stocked with essentials as well as necessary items for beachRead more reviewsLocation:
The location could not have been any better - close to restaurants shops seemingly private (yet public) lagoon and beach areaAnd we are looking forward to returning soonTo wake up to this gorgeous view each morning and enjoy the convenience of being on the beach within minutes offers the best of life in HawaiiWe highly recommend this property and location to anyone looking for the best that Hawaii has to offerThe views from the villa were amazing
5. Beautiful villa with a view (from USD 649)
This charming villa is in an exclusive beachside resort a 10-minute drive from Target store and across the street to restaurants. The unit belongs to a smaller and quieter building in the compound, but with its own lagoon. The well-planned open layout features a professional open kitchen with an island; a round dining table for six, and a living room with a sleeper sofa good for two guests. Sliding doors open to a covered lanai with wicker furniture ideal for entertaining, with wonderful ocean views. The two-bedroom suites contain a king bed and two single beds that sleep, four guests. To sleep two more, the living room sofa spreads out into a bed to sleep two more. There are two luxurious bathrooms with a basin sink, toilet, and bathtub. Guests are required to stay for seven nights with air-conditioning, heating, free internet, cable TV, and washing facilities provided with access to the resort’s amenities.
Top guest reviews
Amenities & Room:
the kitchen is well equipped and the balcony is perfect for relaxingThe beautiful view from the lanai to the comfortable bedsWe had cocktails at the pool barThe views from the balcony were gorgeous and we had views of two lagoons One detail that was a nice surpriseIt has everything you need to feel at homeCleanliness:
Condo was clean and had everything we neededThe property was just as listed Clean and in beautiful conditionLoved hanging out on the Lanai and watching the sunsets Beautiful views and very clean and comfortable placeThe room was clean and very well maintainedHost:
(he is so nice )Place was beautiful Owner responded quickly with any questionsShe answered any questions we had and gave us contact numbers for her and housekeeping for anything we neededThe staff was very friendly and helpful including Sharmaine who helped us with inside information as to various activitiesJust make sure you get notice of any projects going on during your visitRead more reviewsLocation:
Location was great many restaurants within walking distancea cove to swim in that has far less waves than the other beachesWe enjoyed everything about this condo and locationSpacious lanai offered a beautiful view of the resort and beaches--Nice walkway which provided easy access to local hotel restaurants--Enhanced security measures for entering and exiting the buildi...It is located on the beach with walking paths north and south and close walking distance to shops restaurants and a grocery store
6. Top-floor unit with sunset views (from USD 563)
This 11th-floor condo is in the Beach Tower of Ko Olina Resort. It’s closest to the beach, a few miles away from Costco in Kapolei and 21 miles (33.79km) to Honolulu Airport by the freeway. The unit is spacious enough to admit six guests, with its two bedrooms containing a king and two twin beds. From the bedrooms, you have a spectacular view of the ocean. The ensuite master’s bathroom has a separate shower, tub, and toilet with vanity sinks. The second bathroom has a combination shower and tub. Enjoy panoramic ocean views from the master bedroom mini balcony and the covered lanai accessible through the living room. Enjoy family meals in the dining area set for six or on the kitchen island with a breakfast bar. Relax in the cozy living room while watching cable TV or sleep an extra guest on the sofa bed. Air-conditioning, heating, free internet, free parking, laundry facilities, and pool access are provided during the mandatory week-long stay.
Top guest reviews
Amenities & Room:
the guest room was a little tightThe kitchen is fully stocked with pots pansIt has state-of-the-art appliances a fully-equipped kitchen 3 flat-screen TVs and luxurious beds and bedding everything one might need for a comfortable resort vacationYou have your own private beachWe spent most of our time on the expansive balcony eating all of our meals there and enjoying the lovely viewCleanliness:
The accommodations were clean and readyShe's a pleasure to work with and B1103 can't be beat Very private location in the building and perfect for honeymoonit's in pristine condition and has everything your heart could desirewere dirty- maybe done by previous tenant?so don't bother bringing those down to the beachHost:
Seiko responded quickly and was helpful when making the decision and throughout the process Gordon (the host that greated us) was pleasant and helpful when we arrivedThey have a couple of really nice sand umbrellasso that was really niceSeiko was quick to accommodate usWe love how close we were to the ocean and could even leave a door open and hear the waves while falling asleepRead more reviewsLocation:
Very secure building convenient locationThe location was great in a quieter part of OahuSteps away to a beach in a lagoon which was never crowdedIt was really convenient to have an ABC Store and several good restaurants within walking distanceAlthough sometimes it felt out of the way from some of the sights being outside of the busy city made up for the distance
7. Cozy condo in a quiet corner (from USD 975)
This condo is in a secluded area of the Ko’ Olina Beach Resort at Lagoon 2. The interior decor is made of African mahogany wood exuding a masculine touch. The open layout features a cozy lounge with cable TV, a kitchen with restaurant grade equipment and an island, and a six-seater adjustable dining table. Sliding doors open to a furnished lanai where you can lounge with a view of the lush greenery. For sleeping arrangements, the sofa bed in the living room sleeps two guests, a king bed in the master suite sleeps two more, and a queen bed in the second bedroom is for another two. The two bathrooms have toilets, large oversized tubs, basin sinks, and showers. Free internet, air-conditioning, laundry facilities, free parking, and access to the resort’s facilities are provided for at least seven nights.
Top guest reviews
Amenities & Room:
The kitchen was great for making dinners inThe beach /lagoon in front of the condo was way less crowded than any of the othersThe 2 bedroom 2-bathroom room is very clean and comfortableperfect apartment size perfect service:)the condo was very comfortable and suited our group perfectlyCleanliness:
and it is great to be able to allow them to swim in the ocean without fear of big waveswell maintained and the owners (and on-site staff) are very responsiveIt is well maintained and clean resortHost:
The owner was so accommodating to all our needs and made our stay perfectThe property is great owner was greatProperty was well maintained Friendly staffHaving the threat of Hurricane Lane upon our arrival Ray was super responsive and more than accommodatingbeach supplies spices and condimentsRead more reviewsLocation:
The best Luau on the island (Paradise Cove) is only a few blocks away Close driving distance to shopping and restaurantsmany local restaurants all within 10-15 min driveThe local area is very convenient - there's a Target Costco Foodlandsnorkeling gear and boogie boards are providedI have never seen a more beautiful place
8. Lavish condo with panoramic views (from USD 645)
From this seventh-floor unit, guests enjoy picturesque beach views from the lanai. Sliding doors open to a cozy living room, high-class kitchen, and dining area sharing the open space. Of the three bedrooms, the master suite has access to a balcony with a view of the golf course, a king bed, and an ensuite bathroom with vanity sinks, tub, and shower. The two other bedrooms are furnished with a king and two twin beds sharing one-and-a-half bathrooms. Eight guests will enjoy their seven-night stay provided with luxuries like cable TV, air-conditioning, heating, free internet, parking, and pool access.
Top guest reviews
Amenities & Room:
It has 2 bedrooms with 2 King size beds and 1 bedroom with 2 twinssnorkeling in front of the condoThe view from the balcony was perfect as we enjoyed the sunset each nightThe staff was excellent the pools and hot tubsThe suite is furnished to a very high standard with a fully stocked kitchen and all of the ammenities you could ever need on your vacationCleanliness:
The bedrooms are large and the unit is very clean with a beautiful lanaiThe facilities are impeccably maintained and the staff friendly and very helpfulThe lagoons are fantastic and we took advantage of the pools and 3 hot tubs (one with a gravel bottom that was very cool)Host:
We hope to return soon Owner was so helpfulvery responsive Shane was also there to greet us when we arrived and helped us move our luggage upstairs to the unitCQ is very helpful and responsive to emailsHaving rented homes before and been somewhat dissapointed with what we were actually gettingthe dirty towel return the short walk to the deserted beachRead more reviewsLocation:
and there were lots of amenities within walking distance of the villaThis is by far the best luxury condo I have rented from VRBOIn terms of luxury and accommodations the Villa's are levels above the nearby propertiesAnd a short drive up to the north shore for a change of pacehowever we found it to be well situated when we did take the time to get out and explore the island a little
9. Plush villa with a view (from USD 1404)
Watch Hawaii’s famous sunsets over the mountains, from the balcony of this 16th-floor villa of Nai’a building in Marriott Beach Resort. Near the lagoon and the beach, it is also surrounded by outdoor pools, lush tropical gardens, and barbeque grill areas. The unit offers a comfortable stay for eight guests, with its two spacious bedrooms each with a king-sized bed plus two sofa beds, one in the living room and another in one of the bedrooms. Two ensuite bathrooms each have luxurious bathtubs, basin sinks, and toilets. There’s a cozy lounge with cable TV for entertaining, a dining table, and a fully equipped kitchen for cooking family meals. Guests have access to the on-site spa, golf course, pool, and dining establishments.
10. Exclusive villa in high-class resort (from USD 439)
This luxurious villa is in the Ko Olina Resort and Marina near the lagoon and it’s surrounded by pools and spas. It has an Indonesian motif with hand-carved exotic furniture and home accents. To sleep six guests, there are two capacious bedrooms with a king bed and two twin beds with a baby crib available upon request. The master suite has an ensuite bathroom with a spa tub and a private balcony with awesome views. The open-plan space is shared by a cozy living room, an open kitchen with a breakfast nook, and a dining set made of Bali wood, good for six. Luxuries like air-conditioning, heating, cable TV, washing facilities, wheelchair access, free parking, and pool access are available during the required six-night stay.
Top guest reviews
Amenities & Room:
you have to go down 3 floors to the main level and then walk across the resort and past the front desk to the other tower and then go down 2 levels to your carBoth bedrooms are located at the opposite sides of the unit with the kitchen and living room in betweenAnother review mentions the master bedroom mattress being old or lumpyWe loved swimming in the lagoon and the pools and soaking in the hot tubsI kept in contact with DesireeCleanliness:
The best part of the unit was the lanaiWe used them almost everyday and they are smaller in size and it took about 3 hours to dry our clothesHost:
The owner was a great hostessSome reviews mention the washer/dryer not workingWe have contacted the "emergency maintenance" number the owner providedthe owner before and during our stayGreat hospitality and beautiful villaRead more reviewsLocation:
The pools were beautiful and we also used the bbq's on the grounds a few timeswe enjoyed every minute of our staywe enjoyed every minute of our stayThe condo is equally beautiful (and a great backdrop for "getting ready" shots during our wedding day)The villa had everything we needed and we enjoyed every minute
Beautiful beachfront villas
Renting beachfront villas seems to be the best option for shelter when visiting Oahu South Shore. Not only do you have luxurious accommodations, but you also have beautiful views of the sea and mountains with lush surroundings of landscaped tropical gardens, relaxing outdoor pools and other resort standard facilities. These complete your exotic island experience to Hawaii, the kind that will have you coming back for more.
History
Get Trip101 in your inbox
Unsubscribe in one click. See our Privacy Policy for more information on how we use your data
Create an account to