The island of O'ahu is home to the biggest population in all of Hawaii and is also the most visited Hawaiian island, which is why it is known as The Gathering Place. This comes as no surprise as O'ahu boasts beautiful beaches, rich marine life, scenic views, and the best nightlife in Hawaii. If you’ve heard of Waikiki Beach and Pearl Harbor, these are just two of the many things that make O'ahu so popular to vacationers from all over the world.
Are you planning to move to O'ahu or take a month-long vacation on this beautiful island? Don’t miss the chance to stay in one of the best vacation homes. Read on and get to know the top monthly rentals in O'ahu, USA.
We handpicked these listings carefully, considering (wherever possible) host status, recent guest reviews, location, accommodation type, prices, decor, availability of dates, and long-term stay rules and regulations. The image galleries get refreshed with the latest updates regularly. They were last updated on April 13, 2024.
1. Pulelehua Point in Kaneohe (from USD 926)
Marvel in the different shades of blue when you stay in this large waterfront home with a private pool and whirlpool spa in Kaneohe. This property can accommodate a group of eight. It has four bedrooms that offer incredible ocean views with the Koʻolau Range as the backdrop. Imagine waking up in the morning and having that as the first thing you see. You’ll truly have a memorable time in O'ahu.
A minimum of a 30-night rental is required to book this property. You’ll automatically get a 35% discount if you stay 30 days or longer.
Top guest reviews
Amenities & Room:
amazing private pool fantastic views of kaneohe bay just a dream come truethe pool and hot tub was great quiet neighborhoodthe pool and hot tub was great quiet neighborhoodRead more reviewsLocation:
conveniently located out of honolulu but close enough to enjoy the sights therewhat a truly unique and wonderful place
2. Chic island home with private pool in Kailua (from USD 522)
If you are taking a long vacation in Hawaii or you plan to move and live the island life for a while, this stylish home might be a perfect fit for you. It is fully furnished with everything you need to live comfortably, including cozy bedrooms, a well-appointed kitchen, high-speed internet, and best of all, a heated saltwater swimming pool. It’s also conveniently located near local shops.
The floor-to-ceiling windows in this house offer pleasant views of the outdoor area, including the pool and the Bali-style pavilion. If you book this property for 30 days or more, you will automatically get a 10% discount on the nightly rate.
Top guest reviews
Amenities & Room:
the furniture and decor was modern and comfortablethe outdoor furniture is equally comfortable and high qualitybeds and linens were excellent and furniture comfortable for loungingspeaking of the pool the outdoor space was amazinga place to do yoga the plants a beautifully heated poolCleanliness:
property was as pictured and immaculately cleanthe house is clean with great facilities and nice little touchesher place is super cute and clean the pool is amazingbeds were comfy decor was stylish the house was spotless and the pool and backyard are awesomethe house is absolutely spotless the heated pool was beautiful and the property well maintainedHost:
jenny is the best host everjenny was responsive and accommodatingjenny and klei were perfect hostsjenny was a fantastic communicative and welcoming hostjenny is a wonderful attentive host and she has an extremely beautiful propertyRead more reviewsLocation:
absolutely amazing spot close to everything you would needit is excellently located near enough (but not too near) to shops restaurants and the beachthe location was perfect and we felt very safeit is a beautiful place
Superhost
3. Beautiful Hawaiian cottage on Manoa Valley (from USD 199)
Situated in the peaceful Manoa Valley, this newly renovated cottage is beautifully decorated to give you resort vibes with the comfort and familiar feeling of home. It is conveniently located near local shops, restaurants, and beaches. The captivating Manoa Falls is also just a short drive from the property. Staying in this vacation home will give you easy access to the many activities in the area.
This property only accepts 30-day minimum rentals. Kindly reach out to the host if you are interested in booking this property for a long-term stay.
Top guest reviews
Amenities & Room:
super happy there was a/c in the bedroomsplus the outdoor shower was phenomenal oh and the view of downtown especially at night was surprisingly peacefulCleanliness:
clean and very comfortablebathroom was very clean and great showervery clean and very comfortable bedsbeautiful clean and privateeverything was clean and in working orderHost:
our host had great recommendations and was very accommodatinghost was very accommodating and had good local tips- friendly and accommodating hostchuck was very friendly and responded to my questions quicklychuck is also very responsive and isn’t a property manager type which is a good thing for hospitalityRead more reviewsLocation:
the location is great near good restaurants and close to waikikiexcellent location and super accommodationsi highly recomend this location and would happily stay here againthe location of chuck's place was perfect and we were able to walk to the campusnice neighborhood good location great place totally 5 stars
4. Tropical home with garden on the North Shore (from USD 110)
This tropical home features minimalist design and decor and 700 square feet (65 square meters) of indoor space, set on a private road with only a few neighboring houses. Surrounded by a vast garden with different kinds of fruit trees offering privacy and serenity, you will experience a relaxing extended vacation on the North Shore in O'ahu.
It can comfortably accommodate two to four people and has one bedroom, one bath, and a well-appointed kitchen. From this property, you can easily take a bike ride to some of the most beautiful beaches along the path from Sunset Beach to Waimea Bay.
A minimum of 14 days of rental is required. If you opt for a monthly stay, you will get a 20% discount on the regular nightly rates.
Top guest reviews
Amenities & Room:
there is no a/c but once you get the doors and fans on it get comfortable really fastCleanliness:
it was a great size clean and excellently locatednice and clean exactly what we hoped for and very reasonably pricedthis property is updated clean and it’s nice to have a private backyard to enjoythe unit was clean and comfortable and in a great locationgreat location affordable clean quiet and privateHost:
the hosts are helpful and friendlyRead more reviewsLocation:
nice quiet location perfectly situated a short stroll from sunset beachperfect location very spacious one bedroomgreat location on the north shorethis is in a great location near some of the world's best beacheswe were so thrilled to find this vrbo location
5. Fully furnished beachfront home in Waimanalo (from USD 520)
Live in paradise on earth at this spacious beachfront vacation home in the town of Waimanalo, on the eastern end of O'ahu. One episode of the television drama series Hawaii Five-0 was filmed on this property. It features two bedrooms, two baths, a fully equipped kitchen, a living room, and best of all, direct beach access. Get the charcoal barbecue pit going and enjoy island-style dining on the outdoor deck while enjoying the stunning ocean view.
A minimum of a 29-night rental is required to stay in this property with 20% off the regular nightly rates. Get the best out of your vacation in Hawaii by living just a few steps away from the ocean.
Top guest reviews
Amenities & Room:
the house is cozy and immaculate The outdoor living room is a gorgeous backdrop for meals and relaxingThe small beach with a short stair access was perfect for a private swim Hot outdoor shower and hot tub round out the experiencethe property description says IS TRUEThe house and kitchen were spotless and had everything you could needThe bungalow is very private well-appointed and includes so many little extras that show a high level of hospitality and consideration for guestsHost:
Also the door lock does not automatically lock when closedThe owner took us on his boat for a awesome rideYou can not go wrong with renting this propertyThis house and beach was wonderful for our entire familyHot tub was perfect and crystal cleanRead more reviewsLocation:
Yet another awesome stay at Makapu'u Hale :)The views were great and the location was ideal for the local beachesBeing right on the water so close to snorkeling was a dreamMakapu'u Hale is a secret garden perched over a gentle turqupise slice of the Pacific Ocean Surrounded by a beautifully maintained gardenThis property is one of the best we've ever rented for many reasons
6. Beachfront vacation home on Makaha Beach (from USD 408)
Located on Makaha Beach, one of the most popular beaches on the west side of the island, this two-bedroom beach house boasts proximity to the extremely inviting blue waters of O'ahu. It is also a gateway to some of the most scenic sights underwater, with shallow coral reefs on both sides of the U-shaped bay. This property is perfect for those who love snorkeling. Enjoy swimming with the amazing marine life during your long-term stay at this vacation home.
Moreover, you can book this vacation rental for a minimum of 7 nights, but you’ll get a 10% discount if you opt to stay for 30 nights or longer.
Top guest reviews
Amenities & Room:
the bungalow was very comfortable all necessities were providedCleanliness:
this bungalow was very clean stocked well great communication from the owners and we really enjoyed our staythe property was gorgeous clean everything we needed was there for useverything was clean and lisa has everything in the bungalow that you could ever needthe property was as described the beach was perfect the bungalow was clean and functionalthe bungalows are interestingly unique clean and spacious for a family of 4 even with teenagersHost:
the hosts are greatthe hosts were responsive and helpfulthe hosts ken and lisa are greatjust very friendly and down to earth peopleRead more reviewsLocation:
the location was excellentloved this place so close to the beach spent lots of beach timecheck-in was a breeze and the location is amazingit is a great place and we would do it again thanks lisa and ken
7. Luxury beachfront cottage on ʻEwa Beach (from USD 496)
Experience paradise on earth as you wake up to the sounds of the crashing waves and the cool sea breeze. This clean and spacious beachfront cottage is perfect for families as it can comfortably accommodate four to six people. It features tropical Indonesian furniture in the bedrooms mixed with original Hawaiian art, completing your island living experience.
Situated in a quiet neighborhood, you’ll enjoy peace and privacy during your stay. There is also an outdoor deck that is perfect for relaxation and sipping cocktails while enjoying the view of the ocean.
If you book this property for more than 29 days, you will automatically get 25% off the nightly rate.
Top guest reviews
Amenities & Room:
the a/c units were fantastic and individually controlled in every roomlarge deck was perfect for enjoying breakfast lunch and dinner outdoorsthe beds were super comfortablewe stayed with our four adult children and the rooms were a perfect fitHost:
john and linda were superb hostsjohn and linda were very friendly welcoming us to their propertythe host was very helpful and accommodating at all timesjohn and linda (our hosts) are amazingRead more reviewsLocation:
we enjoyed the location so much and it is so close to everywhere we wanted to gothere are gas stations grocery stores and restaurants super closewhen you walk into the house it is just breathtakinglocated in a good place between the tourist trap on waikiki and easy to get to north shore
8. Mountain top house with panoramic views in Maunalani Heights (from USD 210)
Situated on a mountain, this house boasts breathtaking panoramic views. From this property, you can see the vast Pacific Ocean and whales passing by, the Diamond Head volcanic cone, the neighborhood of Waikiki, spectacular sunsets, and so much more. On special occasions, it is also the perfect spot to watch fireworks.
This property can accommodate up to seven people, perfect for taking your family on your dream vacation in Hawaii. If you book at least 30 nights, you will automatically get a 25% discount on the nightly rates.
Top guest reviews
Amenities & Room:
it would've been nice to have air conditioningCleanliness:
very clean and very comfortableHost:
cristin was an amazing host as she was very accommodatingand our host was the best i hope we can return sooncristin was very responsive and helpful we had a great stay at her houseRead more reviewsLocation:
the location was perfect for our vacationgreat location in older honolulu area with many nearby multi-cultural restaurantsabsolutely amazing place to stay the house is in a perfect location for branching out and exploring the islandwe explored the island so the location was great to access all the different parts of the islandthis home is in an amazing location - close drive to all parts of the island
9. Large, fully furnished beachfront home in Laie (from USD 316)
Nestled in Laie, a laid-back coastal area in O'ahu, this large beachfront vacation home is fully furnished and well equipped with amenities to ensure comfortable and convenient long-term stays for its guests. One of the many features you will love about this place is that it offers ocean views from the dining room, living area, kitchen, and especially the deck. On the other hand, the bedrooms will give you stunning mountain views.
This property is located near local shops and restaurants, making it convenient for guests to dine out or stock up on essentials for long-term stays. Enjoy a 20% discount on the nightly rates when you stay in this property for 30 days or longer.
Top guest reviews
Amenities & Room:
no air conditioning which is normal for the area; some nights were more comfortable than othersthe beds were comfortable and the kitchen had everything we neededCleanliness:
this was the perfect beach house very clean and no bugsthe house was clean bright with plenty of spacethe home itself is clean and the beds were comfortableHost:
the owner and managment company were easy to deal withthe owner was a tremendous host and the property is perfect for a hawaii retreat in the perfect locationRead more reviewsLocation:
the location is fantasticthe location is absolutely amazingwould definitely stay again for the locationthe location is great if you're looking for a good beach area and driveabilitythe house was as pictured and the location was awesome
10. Bali-inspired home with ocean view in Waialua (from USD 550)
Located in a secluded area in Waialua, this lovely home offers comfort and privacy with touches of Balinese style incorporated into its design and decor. It also boasts a stunning view of the ocean, which can be enjoyed right on the deck. Sip cocktails while looking out onto the ocean. You might spot some whales too.
With three spacious bedrooms, this rental can accommodate up to eight people, making it ideal for a big family vacation. If you are booking this property for 30 days or more, you’ll enjoy huge discounts on the nightly rates. Note that discount rates may vary per month.
Top guest reviews
Amenities & Room:
there was plenty of space for everybody and it was quite comfortablethe house was quite comfortable and spacious for our adult family of fiveCleanliness:
the house is very clean and cutethis house is very nice well-kept clean with plenty of roomHost:
they were very responsive and kindthe hosts were courteous and very responsivekind honest and a pleasure to interact withclem and terrie were wonderful hostscheck in was super easy and hosts were very responsiveRead more reviewsLocation:
the location was ideal for usright on the water close to everything and absolutely gorgeousloved the location and clem and terrie’s beach housequiet and safe neighborhoodalso we were still being cognizant of covid so this was a perfect private location
Your dream vacation awaits you in O'ahu
One must not let a year pass without a vacation by the sea. Hawaii is one of the best places in the world to do so. Stay in one of the top monthly rentals in O‘ahu, USA, and experience the best of island life in Hawaii.
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