Waimanalo Beach Cottages & Rentals - Quiet Escapes on Oahu's Windward Coast

Waimanalo vacation rentals offer peaceful beachfront cottages and homes on Oahu's windward coast. Enjoy tranquil stays with direct beach access and scenic island charm.

Located on Oahu's serene windward shore, Waimanalo Beach is one of the island's most picturesque coastal stretches - renowned for its powdery white sand, turquoise waters, and uncrowded atmosphere. Unlike the busier resort areas, Waimanalo remains a peaceful residential community where guests can immerse themselves in authentic Hawaiian surroundings.

Our curated collection of Waimanalo Beach rentals provides a luxurious alternative to hotel stays. These upscale cottages range from cozy retreats for couples to spacious homes ideal for families and small groups. Many feature direct beach access, lush private gardens, full kitchens, outdoor lanais, and modern island-inspired interiors - all just steps from the shoreline.

Staying in Waimanalo allows easy access to nearby attractions such as Makapu'u Lighthouse Trail, Sea Life Park, and the beaches of Kailua and Lanikai. Whether you're seeking a romantic getaway or a quiet family vacation, Waimanalo rentals offer a truly relaxing base to experience the beauty and tranquility of Oahu's windward coast. Browse our Waimanalo listings and find your perfect beach escape today.

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$Makapu’u Hale, Literally oceanfront! VIEWS! A\/C, 2 bedroom\/2 bath$

Makapu’u Hale, Literally oceanfront! VIEWS! A/C, 2 bedroom/2 bath

We are literally oceanfront!

E Komo Mai (Welcome) to Paradise!

30 Day minimum stay required by Oahu Ordinance

Our homes are fully furnished with everything you need for an ideal Hawaiian vacation!

Makapu'u Hale is 2 bedrooms, 2 baths, newly decorated with comfortable & charming beach decor with ocean breezes and split A/C units.
Registration Number: GE-174-700-7488-01, TA-174-700-7488-01

3 bedroom
2 bathroom
Sleeps 6

from $625

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Hale Waimanalo Beachfront Home

Commonly known as the Paniolo countryside, you could pass right through the small town of rural Waimanalo on the southeastern corner of O’ahu and never realize what you missed. Nestled in this quaint village is a hidden gem, Hale Waimanalo, where you will wake up every morning to a sunrise over a perfectly turquoise shoreline.
Registration Number: 410060870000, TA-214-325-5040-01, GE-214-325-5040-01

4 bedroom
4 bathroom
Sleeps 12

from $961

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$Beach Front Waimanalo - Licensed Rental: #1990\/NUC-1689 - White Sand Beach!$

Beach Front Waimanalo - Licensed Rental: #1990/NUC-1689 - White Sand Beach!

"Hale Pohaku" - Waimanalo is a beautiful beachfront home on one of Oahu's most spectacular beaches; Waimanalo. Listed on the Register of Hawaii's Historic Homes this classic restored beach house was built of lava rock during the reign of King Kalakaua.
Registration Number: TA-059-395-6864-01, 410040420000, GE-059-395-6864-01

3 bedroom
3 bathroom
Sleeps 8

from $1,320

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Royal Hawaiian Estate – Oceanfront Luxury in Waimanalo

Royal Hawaiian Estate – Oceanfront Luxury in Waimanalo

00 Admin Fee is for our Damage Protection Policy. , Hawaii 5-0, & Lost). Waimanalo's small town doesn't allow hotels, making it the perfect getaway from the busy tourist spots, yet still close to so many great activities and attractions! The countryside of Waimanalo is slow moving and filled with Aloha, beauty, and authentic Hawaiian experiences.

Registration Number: GE-063-319-9104-01, TA-063-319-9104-01, 141002002000

9 bedroom
7 bathroom
Sleeps 20

from $10,723

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$4 Bedroom\/ 3 Bathroom Private Home$

4 Bedroom/ 3 Bathroom Private Home

This home includes ocean views, a rooftop deck, and a heated pool. Enjoy breathtaking views of the majestic lava-formed Ko'olau mountain range and only steps to the # 1 rated beach In the world (2015), Waimanalo Beach, famous for the filming of Magnum PI, Baywatch, Hawaii 5-0 and Lost!
Registration Number: TA-106-722-5088-01, 410060570000, GE-106-722-5088-01

4 bedroom
3 bathroom
Sleeps 10

from $820

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Hale Pahonu – Secluded Polynesian Beachfront Estate in Waimanalo

Hale Pahonu – Secluded Polynesian Beachfront Estate in Waimanalo

Make unforgettable memories in this secluded, polynesian-styled beachfront estate situated on the eastern side of Oahu next door to the famous Magnum PI Robin's nest. Flanked by the majestic Ko’olau mountains on one side and a reef-protected lagoon and beach on the other, enjoy your vacation in island style and comfort.

Registration Number: GE-082-372-8128-01, TA-082-372-8128-01, 410020090000

3 bedroom
3 bathroom
Sleeps 8

from $1,455

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Spacious Home Near a Quiet Beach

Nestled in Waimanalo, this 2-bedroom, 1-bathroom vacation home brings it all within your reach. Fans of nature and the outdoors will love being within a 5-minute walk of Waimanalo Beach and 8 minutes by car from Bellows Field Beach Park. If you'd like to explore the area, you can make the 16-minute drive to Kailua Beach or the 14-minute drive to Hanauma Bay Nature Preserve.
Registration Number: 410050460000, TA-076-575-7440-01, GE-076-575-7440-01

2 bedroom
1 bathroom
Sleeps 5

from $189

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Just a couple houses away from the nicest beach on the island.

Just a couple houses away from the nicest beach on the island.

This rental is across the street from one of the nicest beaches on the island. Don't take our word for it check out the pictures of Waimanalo Beach and Bellows Beach.

Kitchen has everything you need and opens up to a dinning table to enjoy your meals or you can take them outside to the patio.
Registration Number: TA-002-351-5136-01, GE-002-351-5136-01, 410070130000

1 bedroom
1 bathroom
Sleeps 5

from $221

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If You Like Crowds, Don't Stay Here !..Sleeps 2 - Walk to Beach!!

If You Like Crowds, Don't Stay Here !..Sleeps 2 - Walk to Beach!!

Aloha, this Premier Partner property is exclusively available for periods of thirty (30)-days or more. ).

This charming Hawaiiana style studio is perfect for two. Located on a larger corner lot just 5 miles from the bustling town of Kailua and just a short stroll to the 5 mile stretch of white sandy beach in Waimanalo.
Registration Number: TA-120-590-3360-01, GE-120-590-3360-01, 410700023000

1 bedroom
1 bathroom
Sleeps 2

from $179

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Family fun or just relax and say aaah! Max 6, 5 minute walk to Beach !

Family fun or just relax and say aaah! Max 6, 5 minute walk to Beach !

Aloha, this unique Premier Partner property is exclusively available for periods of thirty (30) days or more. )

You will feel right at home in our renovated Hawaiian style family home. Open and spacious this house sits on a large corner lot just a 5 minute stroll to the beautiful safe uncrowded white sandy beach on the Windward side of the island, known as Waimanalo Beach.
Registration Number: TA-120-590-3360-01, GE-120-590-3360-01, 410700023000

2 bedroom
1 bathroom
Sleeps 6

from $334

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Honu Cottage: Quiet, Oceanfront Comfort + EPIC VIEWS!

Honu Cottage: Quiet, Oceanfront Comfort + EPIC VIEWS!

WE ARE LITERALLY ON THE WATER!

E Komo Mai (Welcome) to Paradise!

one rental per 30 day period as required by city & county law

Honu Hale is a charming island-style cottage that sleeps 3 adults or 2 adults and 2 children.
Registration Number: GE-174-700-7488-01, TA-174-700-7488-01

1 bedroom
1 bathroom
Sleeps 4

from $296

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$BEACH FRONT HOME \/5 MASTER SUITES\/LANAI \/7 BATHROOMS\/CENTRAL AIR CONDITIONING$

BEACH FRONT HOME /5 MASTER SUITES/LANAI /7 BATHROOMS/CENTRAL AIR CONDITIONING

This spectacular property is located beach front and has the most amazing ocean views, lots of room to enjoy this pristine beach environment and an ultimate decor with a french touch. All the bedrooms enjoy a private, en-suite bath and all have ocean views except one.
Registration Number: TA-199-621-0176-01, GE-199-621-0176-01

5 bedroom
4 bathroom
Sleeps 10

from $1,160

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House that has it all, Hot Tub, Kayaks, Surf Boards, Snorkeling gear & more

House that has it all, Hot Tub, Kayaks, Surf Boards, Snorkeling gear & more

Located in the Waimanalo Beach Lots, which is only 25 minutes from Honolulu and Waikiki. Waimanalo Beach is one of the largest, cleanest, and most private beaches on Oahu. This white sand beach is very safe (referring to the ocean/surf) so you can relax and not have to worry as your family enjoys the ocean.
Registration Number: 410070800000, TA-002-351-5136-01, GE-002-351-5136-01

2 bedroom
1 bathroom
Sleeps 9

from $357

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2 Bedroom Cottage With Hot Tub

This incredibly located and luxurious ocean-view Hawaiian beach cottage is just steps to 2015's # 1 rated beach in the USA, Waimanalo Beach. In a quiet Hawaiian village, you'll awaken to the sounds of birds, the fragrance of flowers, and waves gently crashing on the beach.
Registration Number: TA-106-722-5088-01, 410060570000, GE-106-722-5088-01

2 bedroom
1 bathroom
Sleeps 5

from $317

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$Mana Kai at Waimanalo: Beachfront Luxury & Tranquility w\/ Stunning Ocean Views$

Mana Kai at Waimanalo: Beachfront Luxury & Tranquility w/ Stunning Ocean Views

This property is offered as a monthly rental. Although full-month occupancy is not required, the monthly rate remains fixed and applies in full, regardless of the number of nights stayed, as prorated rates are not available.

Welcome to Mana Kai at Waimanalo by Gather, your ultimate beachfront escape nestled along the pristine shores of Hawaii’s East Coast.
Registration Number: 410020180000, GE-164-021-9648-01, TA-164-021-9648-01

4 bedroom
5 bathroom
Sleeps 10

from $648

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Bright 3-bedroom tropical house in Waimanalo Beach Lots

Bright 3-bedroom tropical house in Waimanalo Beach Lots

Welcome to our tropical home, a bright and breezy retreat just one block from Oahu's most beautiful beach: four miles of soft sand and gentle waves await you! From the house and patio, you’ll enjoy breathtaking sunset views over the Ko’olau mountains.
Registration Number: TA-125-245-1840-01, 410070830000, GE-125-245-1840-01

3 bedroom
1 bathroom
Sleeps 6

from $302

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