Get away for a special time of romance when you book a trip to the tropical island of Oahu. Oahu boasts a combination of options that will balance your stay between enjoying island activities and finding quality alone time spent together. The postcard-perfect white sand beaches, blue-green sea, and upscale romantic places to stay in Hawaii offer the perfect romantic getaway for you and your loved one.

Book Our Romantic Places to Stay in Hawaii Below

49-60 of 102 results
4 Beds 3.5 Baths 8 Guests
From $329.00/night
4 Beds 3 Baths 8 Guests
From $310.00/night
6 Beds 3.5 Baths 12 Guests
From $267.00/night
4 Beds 3 Baths 8 Guests
From $252.00/night
3 Beds 3 Baths 6 Guests
From $240.00/night
3 Beds 2 Baths 6 Guests
From $225.00/night
3 Beds 2.5 Baths 6 Guests
From $213.00/night
3 Beds 3 Baths 8 Guests
From $202.00/night
4 Beds 3 Baths 8 Guests
From $200.00/night
3 Beds 2.5 Baths 6 Guests
From $199.00/night
2 Beds 2.5 Baths 4 Guests
From $187.00/night
3 Beds 2 Baths 6 Guests
From $180.00/night

Romance on the Sunset Coast

The Oahu vacation rental you choose sets the tone for the entirety of your trip, so be sure to put some time and thought into choosing the perfect romantic rental. The attention to detail and extra touches in our romantic Oahu vacation condos for rent will set your time apart and make this a memorable getaway for all the right reasons. Many of our Oahu vacation villas boast ocean views, allowing you to wake and sleep to the soothing sight of the sea. The tropical weather of Oahu allows for the enjoyment of indoor-outdoor living, so morning coffee and evening cocktails on the lanai can become a part of your daily rhythm. Lavish master suites with spacious king beds and fine linens and en suite bathrooms with oversized soaking tubs and separate spacious showers are features in many of our romantic rentals, allowing you to feel pampered during your couples getaway in Hawaii.

Activities to Enjoy During a Couples Getaway in Hawaii

If the time spent in the car doesn’t mesh well with your vision for a romantic getaway, you’ll enjoy the conveniences onsite at our Ko Olina rentals. This highly desirable resort community offers amenities such as swimming pools, ocean lagoons, spa services, restaurants, and shopping all within its grounds, making it easy to enjoy your time together without sitting in traffic. Activities such as romantic sunset sails can even be booked on-site and enjoyed from the Ko Olina Marina. Further up the sunset coast, we also offer beach homes for rent in Oahu at the oceanfront town of Makaha, which is located near the end of Farrington Highway before the road comes to a halt at the dramatic sea cliffs of Ka’ena Point State Park. Exploring the island will add a sense of adventure to your romantic getaway, and Oahu is home a host of dramatic waterfalls, scenic trails, and beautiful beaches that will forever be engraved into your memories.

Book a Romantic Dinner on Oahu

Oahu’s melting pot of Asian cultures along with the local Hawaiian culture results in a wide variety of cuisines on offer. With access to fresh seafood as well as the dining variety that comes with city life, you are sure to find a restaurant that will set the mood for a romantic evening out as well as satisfy your taste buds. On your romantic getaway to Hawaii, be sure to set aside at least a couple of evenings for enjoying a special night out over good food and drinks.

Nothing says romance like fine dining right along the scenic oceanfront, and as you can imagine, Oahu has plentiful options for seaside dining. Azure offers a table that hovers right over a large swath of sand leading down to the turquoise ocean, with nothing there to obstruct your sea view. Twinkling city lights across the water add to the ambiance in the evenings. This seafood restaurant in Waikiki serves up fine dining options such as lobster and steak. Let your conversation linger over drinks as you spend a special evening together right along the beachfront at Azure!

Another great eatery offering stunning ocean views is Hau Tree Lanai, which boasts an open-air terrace tucked behind the restaurant and only visible from the shoreline. You can’t get much closer to the beach than at Hau Tree Lanai, and the unique outdoor eating area has been built around age-old hau trees, with twisting branches that extend overhead, adding to the ambiance of a backyard patio. More steak and lobster are the mains that you’ll find most popular at Hau Tree Lanai!

From the mountains to the sea, Oahu offers nostalgic scenery at every turn. Try out a different view by heading away from the sea to the mauka (mountains) for dramatic green landscapes. Haleiwa Joe’s Haiku faces the Koolau Mountain Range and is set amid beautifully landscaped koi ponds and botanical gardens. Whether the sun is shining and the sky is blue or wisps of clouds hang over the mountains adding a bit of mystery to the landscape, Haleiwa Joe’s Haiku on Oahu’s North Shore offers a tropical hideaway dining experience. This eatery is known for its excellent prime rib and seafood dishes.

Oahu is filled with opportunities to find romance over a plate of steaming food or a tall glass of wine!

Book One of our Romantic Places to Stay in Hawaii!

When you book your stay with Ola Properties, you can enjoy the peace of mind that your accommodations have been thoroughly vetted by a team of professionals! Whether you’re planning a holiday trip, a summer getaway, or a short-term stay, we have the vacation rental you need. Browse our romantic places to stay in Hawaii today!