Oahu Vacation Rentals – Explore Condos, Villas & Beachfront Homes

Oahu vacation rentals range from oceanfront condos in Waikiki to luxurious resorts in Ko Olina, surfside escapes on the North Shore, and peaceful retreats in towns like Kailua and Waialua. With options for families, couples, long-term visitors, and remote workers, Oahu offers the perfect stay for every traveler.

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Walk to the beach! North Shore Surf House

Reviews (3)

Step into your newly remodeled condo (one of the largest on property). Walk to the beach, restaurants and more. Indulge in luxury with 2 private pools, tennis and pickleball courts, and 5+ miles of pristine beaches just moments away. Dive into adventure with surfing,...

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 6
📍 Kahuku, Hawaii

Gorgeous Lanikai Villa with Access to Secluded White Sand Beach

Reviews (28)

This gorgeous 5 bedroom, 4.5 bathroom, gated oceanfront villa was built in 1918 and has just been fully remodeled with an open, contemporary beach house feel while still honoring the original architecture of the home. In the renovation we revealed beautiful arches...

🛏 5 Bedrooms
🛁 5 Bathrooms
👤 Sleeps 15
📍 Kailua, Hawaii

5-star and rave reviews. Amazing views. Newly furnished. Specials for April/May!

Reviews (159)

SPECIAL RATES for the 2025 Fall Season! Relax in what feels like your open-air home in paradise! Stunning views. Savor the outside air and breezes on your lanai. Superbly maintained. Consistent rave reviews (for years as we are original proud owners).Discounts for stays...

🛏 3 Bedrooms
🛁 3 Bathrooms
👤 Sleeps 8
📍 Ko Olina, Hawaii

Splendid 2BD w/ One FREE Parking

Reviews (2)

This lovely 2 bedroom unit is a rare find in Waikiki. With 1,000 sq ft of spacious living, 2 bath, 2 balconies, 1 free parking, split AC, 4 beds, 8 guests, this unit is one you can't go wrong with. We are centrally located making restaurants, Friday night fireworks,...

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 8
📍 Honolulu, Hawaii

Fully Remodeled! Amazing OCEAN, Mountain, City Views! 2-Bed/2-Bath Sleeps 6!

Reviews (58)

Waikiki Shore #818 – 2161 Kalia Rd.(ONLINE RESERVATIONS CONSIDERED REQUESTS SUBJECT TO APPROVAL)You'll enjoy spectacular Ocean Views from this luxurious 8th floor beach condo (932 interior sf + 160-sf lanai), recently renovated and impeccably designed with a...

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 6
📍 Honolulu, Hawaii

Lanikai Seashore by Gather: Oceanfront Home w/ Mokulua Views, AC & Lush Yard

Reviews (1)

Lanikai Seashore at 1270 Mokulua Drive is a stunning beachfront sanctuary in Kailua, HI, where you can experience the vivid beauty of Lanikai Beach just beyond your backyard. This luxurious 2,100 square-foot retreat artfully blends comfort and style, featuring exquisite...

🛏 4 Bedrooms
🛁 3 Bathrooms
👤 Sleeps 12
📍 Kailua, Hawaii

Makaha Mountain Hideaway

Reviews (2)

The spacePlenty of drawers and cabinets for ample storage for all your travel items. Walk-in closet with storage. I have provided all the basic necessities to start your vacation comfortably upon arrival.Guest accessThe entire property inside and out are available to...

🛏 3 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 10
📍 Waianae, Hawaii

Brand New! Luxurious Sky Ala Moana 2 Bed 2 Bath

Reviews (1)

Summary:*30 DAY MINIMUM* Discover the lively heart of Honolulu and enjoy leisurely walks along the beach with this 2 bed and 2 bathroom apartment on the 16th floor of Sky Ala Moana. Get a charming view of the city and take advantage of the convenience of being close to...

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 5
📍 Honolulu, Hawaii

House close to beach, North Shore, Oahu

Reviews (31)

Located on the countryside of Oahu between the ocean & the mountains, you will be in the perfect spot to experience what Oahu has to offer.Close to world famous North Shore, Turtle Bay Resort, popular surf breaks, snorkeling spots, sea turtles, & much more!Only 2 min....

🛏 3 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 5
📍 Hauula, Hawaii

Charming 2-Bedroom Townhouse Close to the Beach in enchanting KoOlina

Reviews (1)

Book your perfect KoOlina getaway! Stay in a freshly remodeled, resort-style townhome just 1 mile from KoOlina’s famous lagoons and steps from world-class hotels, dining, and shopping. This bright and welcoming Townhouse Kapolei retreat is designed for comfort and...

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 4
📍 Kapolei, Hawaii

Ko Olina Beach Vacation Home

Reviews (1)

Luxurious three bedroom Ko Olina Resort villa located in west Oahu. Enjoy the calm ocean lagoons. In short walking distance to Four Seasons, Marriott Beach Club, Ko Olina Golf and Ko Olina center (restaurants & shops).State of Hawaii requires us to collect 17.75% tax on...

🛏 3 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 6
📍 Kapolei, Hawaii

Hale Kuilima: Condo on the Golf Course at Turtle Bay

Reviews (24)

Our bright and breezy Kuilima West condo is located steps away from Turtle Bay Resort, Lei Lei's restaurant, walking trails, golf, and the beautiful beaches of Oahu's North Shore. With two Tempur-Pedic king beds and AC in all bedrooms and the living room, you can enjoy...

🛏 3 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 10
📍 Kahuku, Hawaii

Luxury Ko'Olina Coconut Plantation Oahu, 2-Story, 5 min to beach

Reviews (45)

Dream-like comfort awaits you and your family in this beautifully appointed 2-story, 1,700-square foot, 3 bedrooms, 2.5 bath townhouse vacation rental condominium in an award-winning residential resort community that offers privacy, relaxation, entertainment, and...

🛏 3 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 8
📍 Kapolei, Hawaii

3-bedroom townhome in peaceful Ewa Beach with AC

Reviews (2)

Enjoy a peaceful stay at this charming 3-bedroom townhome in Ewa Beach. This terrific property features 2 queen beds, 1 twin bed, and a cozy office space with a futon. With amenities like AC, iron, and a hair dryer, guests can relax and escape close to the ocean in this...

🛏 3 Bedrooms
🛁 1 Bathroom
👤 Sleeps 5
📍 Ewa Beach, Hawaii

4-bedroom condo- Tropical luxury Villa in Ko Olina- Sleeps 10

Reviews (1)

Welcome to your private oasis in paradise! Nestled within the exclusive Coconut Plantation community in Ko Olina, Oahu, this luxurious villa offers the perfect blend of opulence, tranquility, and island living. With 4 bedrooms and 3 full bathrooms, this is the largest...

🛏 4 Bedrooms
🛁 3 Bathrooms
👤 Sleeps 12
📍 Kapolei, Hawaii

Available and legal for stays less than 30 days.

Reviews (108)

Hawaii Sheffield House has been a legal bed and breakfast for over 35 years. We are available and legal for stays of less than 30 days. We provide a unique neighborhood stay in Kailua Hawaii that is just down the street from Kailua Beach.The Hawaii Sheffield House...

🛏 1 Bedroom
🛁 1 Bathroom
👤 Sleeps 2
📍 Kailua, Hawaii

Pili Pono: Elegant Honolulu Retreat with Pool & Private Oasis

Reviews (2)

Welcome to Pili Pono, a show-stopping 5-bedroom, 6.5-bath luxury estate set within Honolulu’s prestigious Black Point enclave. Spanning 7,470 sq ft of indoor–outdoor living space on a fully enclosed, gated 0.33-acre lot, this custom-designed retreat blends architectural...

🛏 5 Bedrooms
🛁 6 Bathrooms
👤 Sleeps 12
📍 Honolulu, Hawaii

Ko Olina Beach Villas B301: Serene Beachfront Luxury w/ Pool Views

Reviews (20)

Ko Olina Beach Villas B301 welcomes you to a serene coastal escape on the sun-kissed shores of Kapolei, HI. This beautifully designed three-bedroom, three-bathroom villa spans 1,750 square feet and accommodates up to eight guests. With sweeping ocean and pool views,...

🛏 3 Bedrooms
🛁 3 Bathrooms
👤 Sleeps 8
📍 Kapolei, Hawaii

Ko Olina Kai Estate #20: Elegant Fairway Retreat with Luxe Amenities

Reviews (2)

Bordering the signature 18th fairway of the Ko Olina Golf Course, Ko Olina Kai Estate #20 by Gather offers peaceful resort living framed by sweeping green views, gentle trade winds, and warm island light. This spacious two-story home features over 2,200 square feet of...

🛏 3 Bedrooms
🛁 3 Bathrooms
👤 Sleeps 6
📍 Kapolei, Hawaii

Stunning Kaikea 4Br/4Ba Estate: Luxurious and Private - 5 min from Lanikai Beach

Reviews (1)

Welcome to Kaikea - a tropical oasis nestled just a short walk away from the pristine white sand and turquoise waters of Lanikai Beach, offering an unparalleled experience of luxury and relaxation. Comprised of two separate structures- one newly built in 2018, along...

🛏 4 Bedrooms
🛁 4 Bathrooms
👤 Sleeps 8
📍 Kailua, Hawaii

Beachfront Paradise North Shore, 4BD, King Beds, AC, Parking.

Reviews (11)

Aloha, please send an inquiry first to check dates and availability. Escape to paradise in this newly remodeled beach house with panoramic ocean views. Step from the back lanai directly onto the sand. In the summer months, enjoy a private stretch of beach right out...

🛏 4 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 8
📍 Waialua, Hawaii

Watermark Waikiki Unit 901: Luxe Condo w/ Pool, Resort Amenities & Oceanviews

Reviews (2)

Step into refined island living at Watermark Waikiki Unit 901, a spacious two-bedroom, two-bathroom corner residence in Honolulu’s iconic resort district. From the ninth floor, your lanai frames sweeping views of the ocean, marina, city, mountains, and fiery sunsets—a...

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 4
📍 Honolulu, Hawaii

Spacious Modern 2Bdrm Condo, Free Parking in Bldg., Full Kitchen, Sleeps 6.

Reviews (28)

Renovations were completed in March 2024. Everything is new. 6 can sleep comfortably, 7 when 1 or more are children.This condo is tastefully decorated and features a spacious living room with a comfortable sofa that opens to a full-sized bed, and a flat-screen TV. The...

🛏 2 Bedrooms
🛁 1 Bathroom
👤 Sleeps 6
📍 Honolulu, Hawaii

Spacious 4-bedroom house 5 minutes from beach

Reviews (1)

A true taste of Hawaii - You'll find a coastline of endless beaches, limited crowds, and amazing sea life. Makaha beach can be seen from the windows of this new four bedroom home (5 mi drive), providing plenty of room for large families to come together and relax after...

🛏 4 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 12
📍 waianae, Hawaii

Makaha's Hidden Gem by Kalo Homes

Reviews (21)

Escape to paradise in this beautiful vacation home located in Makaha Valley. Enjoy stunning panoramic ocean views and relax in the tropical backyard. Inside, you`ll find a fully equipped kitchen, comfortable furnishings, and ample space for your group. Take a short...

🛏 3 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 9
📍 Waianae, Hawaii

Completely upgraded, Beach Tower 3 Bedroom. Last minute discounts 4/19-5/21/25.

Reviews (4)

Upgraded 3-Bedroom Beach Villa | Premier Lagoon & Ocean View LocationWelcome to your luxury island retreat at the Beach Villas at Ko Olina. This elegantly upgraded 3-bedroom, 3-bath villa is located on the 4th floor of the Beach Tower, just one building back from direct...

🛏 3 Bedrooms
🛁 3 Bathrooms
👤 Sleeps 8
📍 Kapolei, Hawaii

Oceanfront Island Living at its Finest! Unbeatable Panoramic Ocean Views!

Reviews (27)

Waikiki Shore #1400 – 2161 Kalia Rd.TRUE direct beachfront unit overlooking the sandy Waikiki shoreline with breathtaking panoramic ocean views! Full kitchen, free Wi-Fi, free parking for 1 vehicle. This 1-bedroom condo's generous 1,188 sqft of interior living space...

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 6
📍 Honolulu, Hawaii

Hale Lanikai – Classic Hawaiian Style Beach House & Guest Cottage

Reviews (52)

HALE LANIKAILic# TA-161-257-7280-01Non-Conforming Use Permit Number 90/TVU-0031and is compliant with Hawaii State Legislation (HB2078) for vacation rental accommodations.Hale Lanikai is BACK! Better than ever!!All new furnishings throughout the property.Original Koa...

🛏 4 Bedrooms
🛁 4 Bathrooms
👤 Sleeps 8
📍 Kailua, Hawaii

Fairways Ko Olina 27H: Your Ultimate 3BR Retreat in Hawaii with Resort Access

Reviews (2)

Welcome to Fairways at Ko Olina 27H, a spacious three-bedroom, two-and-a-half-bath townhouse offered exclusively as a monthly vacation rental within the gated Fairways community on Oahu’s sunny west coast. This comfortable home blends open living spaces with serene...

🛏 3 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 8
📍 Kapolei, Hawaii

Resort Style with Hula Show, Fireworks and even Tiki Torches!

Reviews (111)

The Ilikai is the first hotel-resort condominium developed in Hawaii and is one of the original landmarks of Waikiki. It is best known for being featured in the Hawaii 50 TV series and is loved by tourist and locals alike. Conveniently located in Waikiki next to the...

🛏 1 Bedroom
🛁 1 Bathroom
👤 Sleeps 4
📍 Honolulu, Hawaii

Walker's Lanikai Beach House – Historic Oceanfront Retreat

Reviews (132)

This property is professionally-managed by Private Homes Hawaii, LLC and is licensed as a short term vacation rental, Non-Conforming Use Permit Number 1990/NUC-1757. It is compliant with Hawaii State Legislation (HB2078) for vacation rental accommodations,...

🛏 5 Bedrooms
🛁 4 Bathrooms
👤 Sleeps 14
📍 Kailua, Hawaii

Turtle Bay Fairway Condo - Kuilima Estates East

Reviews (4)

Welcome to your North Shore paradise! Step into our fully remodeled Turtle bay condo, boasting breathtaking views of the 18th hole through wall-to-wall windows. Outside, Indulge in luxury with 2 private pools, tennis and pickleball courts, and 5+ miles of pristine...

🛏 3 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 8
📍 Kahuku, Hawaii

1BR/1BA/2 Parking Condo: Fully Renovated at Ritz Carton Turtle Bay

Reviews (2)

*Gutted to Gorgeous: everything new* - JAN 2025: FULL Renovation - *Professionally Sanitized: always glistening clean* - New kid on the TBR block - you’ll feel the Aloha - TBR: 1 Bedroom/1 Full Bathroom/ 2 Guest Parking - Perfect get-a-way w/ sandy beach cove - Immersed...

🛏 1 Bedroom
🛁 1 Bathroom
👤 Sleeps 4
📍 Kahuku, Hawaii

Professionally Decorated, Beachfront, Double Unit on the 18th floor.

Reviews (17)

Famed COLONY SURF condo on Oahu's 'Gold Coast' on the Diamond Head end of Waikiki. This romantic get-a-way is perfect for an unforgettable Hawaiian vacation. An extra large DIRECT OCEANFRONT 1,440 sq' condo with a 25' long panel of windows in the living room and 12' of...

🛏 1 Bedroom
🛁 2 Bathrooms
👤 Sleeps 4
📍 Honolulu, Hawaii

Luxury 2 bedroom in Waikiki!

Reviews (1)

Welcome! We hope you enjoy the newly renovated and spacious 2 bedroom/2 bathroom. This high-floor unit has an amazing wrap-up lanai deck featuring 180 views of Diamond Head, the ocean, the mountains, the sunrise, sunset, and metro Honolulu. You’ll be a 10-minute walk to...

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 4
📍 Honolulu, Hawaii

2 Bedroom Condo On Hawaiian Beach - Family Friendly - 7 nights

Reviews (4)

Treat your family to the tropical vacation of a lifetime at this luxurious Marriott beachfront resort on the island of Oahu. Nestled along the sparkling Pacific Ocean and surrounded by palm-lined lagoons, this premium retreat offers the perfect mix of adventure,...

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 8
📍 Kapolei, Hawaii

Newly Renovated Waikiki 2BD 2BA Ocean City View

Reviews (1)

Summary:Aloha! Experience the best of Honolulu in this fully renovated apartment at 444 Niu Street. Enjoy the convenience of a full kitchen, partial ocean views, and free garage parking. With two bedrooms and two bathrooms, this apartment is perfect for a relaxing...

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 7
📍 Honolulu, Hawaii

Beachside 🏖 Family, vacation home with pool 🌺 NO CLEANING FEE!

Reviews (9)

This Kailua, beachside, pool (heated) home was completely remodeled in 2019 with all new kitchen, bathrooms, pool house, pool surround, landscaping, TV's, furnishings, etc. And NO CLEANING FEE on 30 day bookings!Each room has an individually controlled AC system. The...

🛏 5 Bedrooms
🛁 1 Bathroom
👤 Sleeps 10
📍 Kailua, Hawaii

Diamond Head Surf House: Gold Coast Oceanfront Home w/AC & Gorgeous Views

Reviews (1)

Completely immerse yourself in oceanfront island living at the stunning three-level retreat known as the HLH Team, a spacious 3BR luxury home positioned along Oahu’s coveted Gold Coast between Diamond Head and Waikiki. This monthly rental delivers panoramic shoreline...

🛏 3 Bedrooms
🛁 3 Bathrooms
👤 Sleeps 8
📍 Honolulu, Hawaii

Monthly Discovery Bay 1713 Ocean/City Views 1 Bd 1Ba

Reviews (1)

WAIKIKI / OCEAN VIEWS, 5 Minute Walk to Beach, Remodeled, Furnished and Fully Appointed. No smoking condo. Parking, Pool, Utilities, WIFI, BBQ, Gym, Sauna, Security, Washer/Dryer Included. Monthly.Excellent Views from Breezy Lanai, Tasteful and Clean. Monthly / contact...

🛏 1 Bedroom
🛁 1 Bathroom
👤 Sleeps 4
📍 Honolulu, Hawaii

Koi Palms 1 bedroom Cottage - Great location! 5 Minute Walk to Kailua Beach!

Reviews (136)

Come and enjoy our island home with us. Koi Palms Cottage is located within our gated property alongside our lovely Koi pond, in the quaint town of Kailua. The owners live on the property in the main house.The cottage is a 600 square foot 1 bedroom unit. The kitchen is...

🛏 1 Bedroom
🛁 1 Bathroom
👤 Sleeps 2
📍 Kailua, Hawaii

Ohana Kai: Modern Water Front Condo w/Gorgeous Views, A/C, Yard, & Shared Pool

Reviews (1)

Ohana Kai offers the rare chance to stay directly along the tranquil waters of Hawaii Kai’s marina, blending the ease of island living with the comforts of a contemporary home. Set within a private gated community on Oahu’s south shore, this two-story corner condo...

🛏 3 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 8
📍 Honolulu, Hawaii

Beachfront Paradise/Ocean Views & 5 Star Reviews/ Shared pool. Steps to the Sea!

Reviews (13)

paradisesandshawaiirentals.com8083828016E komo mai — welcome to our Turtle Bay Ocean Villa! Nestled within the iconic Turtle Bay Resort, this newly updated and beautifully redecorated 1,700 sq. ft. villa is designed to make your Hawaii vacation dreams come true. Located...

🛏 3 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 8
📍 Kahuku, Hawaii

Modern Luxury Suite at Waikiki Beach Tower w/ Ocean View

Reviews (10)

Relax in this beautifully renovated unit with ocean views at Waikiki’s finest oceanfront condo building. Wake up to the crystal blue ocean from the luxurious king bed in the master bedroom, entertain family and friends in the open kitchen and living room, and enjoy a...

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 6
📍 Honolulu, Hawaii

LUXURY 2-Bed Condo, Kitchen, Wi-Fi, Parking, W/D, AC, LEGAL Monthly Rental!

Reviews (3)

Allure Waikiki #804 – 1837 Kalakaua Ave.(LEGAL 30-Night Minimum Rental in the Resort Zone! Max Stay 3 Months. ALL MONTHLY RESERVATIONS ARE SUBJECT TO APPROVAL.)Experience luxury Waikiki living at its finest! This 2-bedroom, 2-bath condominium with high-end touches...

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 4
📍 Honolulu, Hawaii

Luxurious Two bedroom Unit with Panoramic Ocean View in ONE Ala Moana

Reviews (2)

This luxury corner unit has an epic panorama ocean view with floor-to-ceiling windows on 2 sides of the unit for a spacious feel. ONE Ala Moana is the pinnacle of world-class living. This unit has 2 bedrooms, 2 baths, and 2 parking stalls directly in front of the...

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 4
📍 Honolulu, Hawaii

Corner Unit Beachfront Condo with Wrap-around Lanai at Makaha

Reviews (64)

30 day minimum, contact owner for additional details. Secluded beach, the Pacific surf, beautiful sunsets, mountains, whales, turtles... Enjoy them all from your spacious (nearly 400 sf) covered lanai. Swim in the salt water pool, soak in the hot tub, lounge on the...

🛏 1 Bedroom
🛁 1 Bathroom
👤 Sleeps 4
📍 Waianae, Hawaii

Largest Ocean Villa at Turtle Bay! Fully Renovated 4BR w/ beach, pool & hot tub

Reviews (21)

Ocean Villa G218 is the largest and most luxurious 4BR/3BA unit at the gated Ocean Villas at Turtle Bay. With ocean-facing views, spacious interiors, and elegant design, it offers privacy and comfort just steps from the beach, pool, dining, golf, and hiking trails....

🛏 4 Bedrooms
🛁 3 Bathrooms
👤 Sleeps 12
📍 Kahuku, Hawaii

Coconut Villa Entire home in Koolina Walking distance to the shops and beaches

Reviews (5)

Enjoy your morning coffee or evening cocktails out on our lush tropical lanai with the tranquil backdrop of the Ko Olina golf course. Take in the stunning sunsets from this perfect vantage point.Our villa is located in an ideal location; everything is within walking...

🛏 3 Bedrooms
🛁 3 Bathrooms
👤 Sleeps 6
📍 Kapolei, Hawaii

Kailua Condo / Townhouse on Oahu 7 day per 30 day period

Reviews (3)

”Aloha and Welcome Home" message me on availability as it can only be rented once in a 30 day period. Ordinance 19-18 does not require a renter to physically occupy a rental property for any minimum length of time. Remodeled 2x bedroom 2x bathroom condo / townhouse. It...

🛏 2 Bedrooms
🛁 1 Bathroom
👤 Sleeps 5
📍 Kailua, Hawaii

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