Vacation rentals with a pool in Waianae

A bright living area features large sliding glass doors offering unobstructed views of the ocean. Comfortable seating is arranged around a coffee table, with a TV mounted nearby. Tropical decor and tile flooring create a relaxing atmosphere, inviting guests to enjoy the coastal scenery.

4.95 out of 5 average rating, 123 reviews

9K Hawaiian Princess - Alii Hale Aina

Beautiful remodeled Hawaiian Princess unit on one of the best beaches on Oahu. The view is nothing less than spectacular. The condo has been remodeled with the best of everything. You will not find a better place on the island if you are looking for a beach vacation away from the crowds of Waikiki. This unit has an NUC and is permitted rental Feel free to message me (scroll to the bottom) if you cannot find availability on the calendar. I have other listings on island that may be available

The living area is characterized by high ceilings and natural light streaming through large windows. A comfortable gray sofa is accompanied by wooden chairs and tables, creating a welcoming gathering space. A neutral rug adds warmth, while tropical plants contribute to the serene atmosphere.

4.97 out of 5 average rating, 114 reviews

Makaha Hale - Serene 3 BR Home

Escape to the beautiful Makaha Valley in Hawaii and experience a truly unforgettable stay at our 3-bed 2.5-bath house. This enchanting Airbnb, nestled within a secure gated community offers a getaway for those seeking tranquility amidst the breathtaking beauty of the island. Enjoy breathtaking views of the Makaha Valley mountainside, modern amenities, and a serene ambiance. Indulge in nearby pristine beaches and immerse yourself in the beauty of the island. Your dream Hawaiian getaway awaits!

4.97 out of 5 average rating, 344 reviews

A scenic sunset view highlights the horizon over calm waters, with soft waves lapping against the sandy beach. In the foreground, a decorative dolphin sculpture adds a touch of charm to the balcony railing, while lush greenery frames the view.

Condo in Makaha

Beachfront Getaway - Hawaiian Princess Condo

Mesmerizing sunset views from this sandy beach front condo. Nothing separates you from sparkling turquoise waters but footprints in the sand. Balcony is ideal height for turtle watching. From Nov- April you may spot a whale. This vibrant land is full of surprises. Even dolphins spin by now and then. Escape the crowds of Waikiki to experience a real Hawaiian lifestyle. Snorkel, boogie board or surf right out your door. Awakening to the rhythm of the ocean can change your life forever.

4.98 out of 5 average rating, 121 reviews

The exterior of the cottage showcases a modern design with a welcoming front entrance and large windows. A two-car garage is visible on the right, while stunning mountain scenery frames the background. The sky is adorned with soft hues of pink and orange as the sun sets.

Cottage in Waianae

Cottage Nene - Luxury Home by Beaches & Mountains

Modern luxury meets valley tranquility. Built in 2022, this spacious 3-bed, 2.5-bath cottage hosts up to 8. Enjoy an airy living room with 14ft ceilings, premium furniture, and smart TVs. Step outside to a fully landscaped tropical yard with the best mountain views in the community, perfect for morning coffee or evening stargazing. Enjoy community pool, jacuzzi, and gym, all while being minutes away from world-class west-side beaches and hiking trails. Guaranteed cancellation in 48 hrs.

4.9 out of 5 average rating, 119 reviews

Guesthouse in Waianae

Private Studio no shared spaces with own entry

Escape to this cozy, intimate studio in Makaha Valley’s exclusive gated resort community The Cottages at Mauna’Olu Surrounded by lush, tropical landscapes, this private retreat offers the perfect blend of comfort and tranquility your area is not shared with the main house it’s private and fenced away from each other. Unwind on famous Makaha Beach, just 4 minutes away, explore nearby hiking trails, or simply relax to the soothing sounds of the mountains. With thoughtful amenities 🌿

4.95 out of 5 average rating, 149 reviews

Oahu Ocean View • Sleeps 14, Pool, Hot Tub, Beach!

Why guests love our cozy Makaha Valley home: Our home is right next to the resort-style pool, spa, and fitness center. Free parking for up to 4 cars (hotels charge $40–$100 per car) Full kitchen—cook your own meals and save on dining out 4-stage reverse osmosis drinking water—no need to buy bottled water Private backyard with a BBQ grill—perfect for outdoor dinners Washer and dryer in the garage—travel light! Gated community with pool, hot tub, gym, and scenic mountain views

A sweeping view of the ocean is enhanced by a vibrant rainbow arching across the sky. Waves gently lap the shore, while a distant mountain creates a picturesque backdrop. The sandy beach is bordered by lush greenery, embodying a serene coastal landscape.

4.85 out of 5 average rating, 234 reviews

Beach Beauty and Comfort in remote Oahu Paradise

This is among the nicest locations in all Hawaii. You are literally over a quiet, beautiful pristine beach. Beautiful valley views East. Sparsely populated beach below. Excellent sand and swimming. Beach amenities on hand. The condo is beautiful, comfortable, and nicely updated. Great local swimming, snorkeling, surfing, hiking, dolphins, turtles. Personally, I do not know a better place in Hawaii to visit if you do not need bars and shopping. Nice facility amenities below.

4.81 out of 5 average rating, 129 reviews

A private balcony is showcased with two light blue chairs positioned around a small table. The view highlights ocean waves and lush palm trees, creating a serene backdrop. The indoor-outdoor space invites relaxation with clear skies and gentle breezes.

Condo in Waianae

*Serendipity on the Moana! - Legal & Beachfront!*

Gorgeous, Fully Furnished, Beachfront, legal one-bedroom condo with over 740 square feet in Maili on Oahu. Maili Cove is a hidden gem and has easy access to golf courses, amusement parks, restaurants, shopping centers, financial and medical facilities and other services located on the west side of the island. Just 15 minutes down the road is the Disney Resort & Ko Olina. Owner a licensed real estate agent. State #1990/NUC-2309. TMK870280170031.

The exterior of a modern home is highlighted at sunset, showcasing large windows that emit a warm glow. Lush tropical plants frame the entrance, while mountain scenery provides a dramatic backdrop. A well-maintained lawn complements the inviting appearance of the house.

4.96 out of 5 average rating, 114 reviews

Ocean+Mountain View|Beach 5 Min|BBQ|Gated|Parking

Set inside Mauna Olu Estates, a gated retreat in Makaha Valley, this 4-bedroom Airbnb Guest Favorite pairs ocean and mountain views with a private backyard hot tub and a string-lit gazebo for evening lounging. Sleeps 9 across a first-floor king master, two queen bedrooms, and a bunk room, with a shared community pool and gym just steps from the door. A quiet, family-friendly base minutes from Makaha Beach and a short walk to the golf course.

An open dining area is highlighted by a large wooden table with seating for six, complemented by natural light from sliding glass doors. The adjacent kitchen features modern appliances and a spacious island with bar seating, creating a welcoming atmosphere for gatherings.

4.96 out of 5 average rating, 138 reviews

Hawaiian Pakele (escape)

Aloha and welcome to our home!! Newly built and luxuriously appointed, this beautiful 3 bedroom and 2.5 bathroom house is the ideal spot on the west side of Oahu. Located in the private gated community, with breath taking views of ocean and mountains and only a 3-min drive to the world famous Makaha beach. This is the most desirable location for families, friends and couples to escape, relax and enjoy a rejuvenating and memorable vacation!

4.94 out of 5 average rating, 196 reviews

An aerial view captures the sandy beach stretching along the coastline, bordered by lush green hills. Crystal-clear turquoise waters gently lap the shore, with a few beachgoers enjoying the day. Colorful umbrellas are dotted along the beach, creating a vibrant contrast against the natural surroundings.

Guest suite in Waianae

Slice of Paradise-Studio-Sleeps 4-Same$ for 4 as 2

Enjoy this beautiful, private, brand new studio nestled in the mountains of Makaha Valley. This is located in a gated community with 24 hour security. Minutes from year round surfing and golfing. This is a LEGAL vacation rental. Private yard on a perimeter lot with unobstructed ocean and mountain views and just a few minutes drive to many clean, sand bottom beaches. Any combination of 4 guests is okay as long as there is a max of 2 adults.

4.94 out of 5 average rating, 155 reviews

Private SPA, Sleep 12, Beach 5 min

Why do guests LOVE our home? Whole house in Makaha Valley, Oahu's West Side, Leeward Coast — sleeps 12, private hot tub, backyard pool, mountain and ocean views, Makaha Beach 5 minutes away. All for under $100 per person per night. The less-touristed, more-local Hawaii. Perfect for multi-generational families and friend groups who want the whole house, not adjacent hotel rooms. Pets welcome. Top Airbnb 5% Guest Favorite homes.

Popular amenities for Waianae rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.81 out of 5 average rating, 192 reviews

Home in Kawela Bay

Townhome w/Turtle Bay, pool & beach access

4.97 out of 5 average rating, 148 reviews

A serene bedroom features a spacious bed with crisp white linens, complemented by soft, natural textures. Large windows showcase ocean views, while two woven light fixtures add warmth. A dresser provides additional storage, and a neutral rug enhances the calming atmosphere.

Home in Waikiki

Waikiki Gem, Stunning Ocean View, Parking Included

5.0 out of 5 average rating, 25 reviews

Lani Kai Ocean View Villa Sleeps 12 Pool + Hot Tub

Aerial view of a spacious villa nestled in a gated community, surrounded by lush greenery. The property features a well-maintained yard and a garage, with a scenic backdrop of mountains and the ocean visible in the distance.

5.0 out of 5 average rating, 10 reviews

Ocean-Sunset Views Home in Gated Makaha Community

An aerial view captures the spacious homes of the secure gated community, featuring individual yards and driveways. The ocean sparkles in the background, framed by lush green hills and the outline of distant buildings, showcasing the peaceful beauty of the Makaha Valley.

4.92 out of 5 average rating, 50 reviews

Ocean View Exquisite Home at Cottages at Mauna Olu

4.98 out of 5 average rating, 40 reviews

Mystic Mermaid Island Retreat

The exterior of a modern two-story home is depicted, featuring a welcoming porch and a well-maintained driveway. Lush green landscaping complements the home, with a backdrop of majestic mountains partially shrouded in mist, adding to the serene environment.

5.0 out of 5 average rating, 47 reviews

Westside Hawaiian Sanctuary-New Home w/ 24hr Gated

The home features a spacious layout with a large backyard, showcasing stunning mountain views. An outdoor seating area is visible, and the surrounding landscape includes well-maintained lawns and neighboring houses. Clear skies and lush greenery enhance the tranquil setting.

4.86 out of 5 average rating, 49 reviews

Makaha Hideaway by AvantStay | 10 Minutes to Beach

Condo rentals with a pool

Condo in Downtown Honolulu

Modern 1 Bedroom Condo in Downtown Honolulu

4.98 out of 5 average rating, 284 reviews

4.76 out of 5 average rating, 170 reviews

A private lanai is seen through sliding glass doors, featuring two chairs and a small table overlooking the ocean. Lush palm trees are visible, with water glistening under the clear sky. The space has green turf flooring, providing a vibrant touch.

Condo in Punaluu

"Endless Summer" Beachfront Condo w/ Full Kitchen!

4.97 out of 5 average rating, 177 reviews

A spacious lanai provides breathtaking ocean views, featuring comfortable seating with striped cushions. A round table sits at the center, suggesting a perfect spot for outdoor relaxation. The backdrop includes lush greenery and a distant resort, embodying a serene coastal ambiance.

Condo in Kapolei

Ko Olina Beach Villas Ocean View 2BR 10th Fl B1003

4.95 out of 5 average rating, 176 reviews

A tranquil outdoor seating area features a cozy hanging chair beside a round dining table. The expansive balcony overlooks city views and distant mountains, with soft clouds enhancing the bright sky. Green plants add a touch of nature to the serene space.

Condo in Waikiki

38th FLR- Luxe King Boutique Studio 1000 Cranes

4.94 out of 5 average rating, 101 reviews

An open studio layout showcases a spacious bedroom area with a king-size bed and a cozy seating arrangement featuring a dark sofa. Large glass doors frame stunning ocean and harbor views, while a TV is positioned for easy viewing from the living area.

Condo in Waikiki

Beautiful OceanView&Sunset @IlikaiResort w/Parking

4.94 out of 5 average rating, 250 reviews

A modern kitchen is featured with light wood cabinetry and natural stone countertops. Three rattan bar stools are positioned at the breakfast bar. Pendant lights with woven shades hang above. Fresh greenery is placed on the counter, enhancing the spacious and airy feel of the room.

Condo in Kawela Bay

♥ North Shore Paradise at Turtle Bay ♥

4.86 out of 5 average rating, 470 reviews

Condo in Kawela Bay

North Shore Oahu Getaway at Turtle Bay Resort

Condo in Downtown Honolulu

A spacious room features a large window showcasing expansive views of the ocean and harbor. A work desk and chair are positioned near the glass, while a cozy bed is visible in the foreground. Natural light enhances the modern decor and serene atmosphere.

Luxury Condo with Ocean Views & FREE Parking!

4.96 out of 5 average rating, 182 reviews

Other vacation rentals with a pool

4.98 out of 5 average rating, 117 reviews

Apartment in Kawela Bay

37 West 1 Bedroom + Murphy Bed TA-104-613-6320-01

4.88 out of 5 average rating, 275 reviews

A two-story building is framed by lush greenery and large windows. A white staircase leads to the upper level, while balconies are visible. The exterior showcases a light-colored facade that blends with the natural surroundings, creating a serene residential setting.

Apartment in Kawela Bay

Turtle Bay Corner Condo With A Fairway View!

4.88 out of 5 average rating, 164 reviews

The image captures a sunset view over the ocean, framed by palm trees and a neighboring cottage's overhang. A grassy area leads to the water’s edge, where calm waves meet the shore. Light reflects off the water, creating a serene ambiance.

Cottage in North Shore

Best Kept Secret on Oahu! and WE ARE LICENSED!!!

4.95 out of 5 average rating, 21 reviews

Beachfront Condo at Makaha

An outdoor balcony features a table and two chairs with a view of the horizon. The sun sets over the calm ocean waters, creating a gradient of colors in the sky, ranging from deep orange to soft pink, reflecting on the water's surface.

4.95 out of 5 average rating, 95 reviews

Make your next vacation, Paradise! Free Parking!

4.71 out of 5 average rating, 7 reviews

A sandy beach is framed by palm trees and rocky formations. The calm turquoise water gently laps against the shore, while fluffy clouds drift across a bright blue sky. The tranquil atmosphere highlights the natural beauty of the coastal landscape.

Home in Kapolei

New Listing! Ko Olina 3BD Steps from the Ocean

4.88 out of 5 average rating, 86 reviews

A private lanai offers a table and several lounge chairs with ocean views. The tropical landscape includes a palm tree, and the vibrant blue ocean extends seamlessly to the horizon. Natural light illuminates the space, enhancing the outdoor atmosphere.

Condo in Makaha

Beachfront Condo-Legal-Free Pkg/Wifi-Pool, HotTub2