Hawaii Vacation Rentals – Island Condos, Beachfront Homes & Luxury Villas
Welcome to your guide for Hawaii vacation rentals, where tropical luxury meets everyday comfort. From sunrise-facing lanais on Maui to private bungalows near the lush valleys of Kauai, each rental is handpicked for quality, location, and local charm.
Why Book a Vacation Rental in Hawaii?
Unlike traditional hotels, vacation rentals provide full kitchens, private lanais, and dedicated living space—ideal for families, couples, or long stays. Many homes are steps from the beach, offer high-speed Wi-Fi, and include perks like pools, BBQ areas, or resort access.
Popular Vacation Rental Locations
- Waikiki, Oahu – High-rise condos near beaches, shops & nightlife
- Kihei, Maui – Walkable, affordable, and family-friendly
- Princeville, Kauai – Scenic cliffs, golf, and luxury condos
- Kailua-Kona, Big Island – Oceanfront escapes with sunset views
Rental Types Available
- Beachfront Condos with resort amenities
- Private Beach Homes with full kitchens
- Luxury Villas with pools & panoramic views
- Studios & Bungalows for solo travelers or couples
What Makes To-Hawaii.com Rentals Stand Out?
- Verified properties across all major Hawaiian islands
- Detailed descriptions, amenities, and photo galleries
- Helpful internal links to top Hawaii activities and Hawaii rental cars
- Flexible booking options, from weekend getaways to long-term stays
Plan Your Dream Island Escape
Explore the beauty of the islands with confidence. Whether you're whale watching on Maui, snorkeling on Oahu, or enjoying a peaceful sunrise on Lanai, our vacation rentals offer the perfect base for unforgettable memories. Start planning your Hawaiian adventure today.
The Little Hut at Sealodge is a luxurious, wabi sabi styled, One-Hotel-Comp, with a chef`s kitchen and more expansive view. Truly the newest, nicest, coolest unit in Sealodge. Stunning ocean views from every room, whether waking up to the sun rising over the light house...
Keauhou Surf & Racquet 7-101 - Walk to snorkel
Relaxing Keauhou Condo w/ Golf Course Views | Walk to SnorkelingEscape to paradise at this peaceful 2-bedroom, 2-bath condo in the highly sought-after Keauhou Surf & Racquet Club on the sunny Kona Coast. Nestled on 16 oceanfront acres, this ground-floor unit offers no...
Pristine Retreat at Popular Resort
Keep it simple at this peaceful and centrally-located hotel room at the popular Outrigger Kauai Beach Resort. . Pristine oeanview across a pastoral field from private lanai. Location is a full service resort with many pools, hot tubs, beautiful grounds, a couple of...
Fantastic View, Waikiki DiamondHead
A beautifully remodeled home in the hills of Maunalani Heights, Honolulu. Enjoy amazing views of the iconic Diamond Head, the Pacific Ocean, Kahala and Waikiki.Come enjoy the real Hawaii.. Awaken to the sounds of singing birds, not cars and buses.
New Luxury Penthouse! Sky Ala Moana 2bd/2ba
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 43rd floor of Sky Ala Moana. Get a charming view of the island and take advantage of the convenience of being close to...
Marriott Ko Olina Beach Club - On The Beach- Family Friendly - Mountain View
Come experience Hawaii at this premium level Marriott Resort in Oahu. With luxurious amenities and great family entertainment, your family won't want to leave.This property has everything you need for a tropical vacation. There is a lagoon style family pool with...
Experience Unparalleled Luxury in a Mountain View Studio at Marriott’s Ko Olina!
Indulge in a serene escape at Marriott’s Ko Olina Beach Club, where your villa is surrounded by crystal-clear waters and a breathtaking lagoon. Nestled within a lush, gated community on the stunning island of Oahu, our premium vacation ownership resort offers the...
** Limited Time Special Offer: Reserve any KBM Resorts property in Hawaii with an arrival date between now and December 31, 2026 for 6 nights or more and receive a FREE 4-door rental car from top providers--Hertz, Alamo, Avis, or Budget. Convenient airport pick-up and...
2BR Ocean View at Waiohai Beach Club – Poipu Beach Paradise
Marriott’s Waiohai Beach Club sits directly along Poipu Beach, one of Kauai’s most popular and sunniest coastal areas. The resort features lush tropical landscaping, multiple lagoon-style pools, hot tubs, and direct beach access.Guests can relax in shaded garden...
Aloha casa kona heavenly retreat
Best house for a lovely vacation in kona.Situated above the highway on a cool elevation with a cool breeze coming in from the ocean.This peppery is perfect for a family or travel companions. It features 3 bedrooms and 3 bathrooms.
Beachfront Studio in North Shore - Lower Unit
Discover a surfer's paradise at this beachfront studio located in Haleiwa, Oahu. With private access to the beach, this idyllic location is in front of a popular surf spot. Lounge comfortably on the porch and have lunch at the outdoor dining area right outside the...
A charming, secluded, off-grid, quiet and a 180 degree view of the ocean.
This delightful studio in Southpoint of Naalehu is a charming retreat for guests looking to unwind and relax. Situated on a 23 acres of rolling grass lands with no neighbors, no cocky frogs, no roosters to disturb one’s well being and is a smoke free environment. This...
Puamana 254-2 3BD Gated Oceanfront Townhome w/ 2 Lanais, Lawn & Sunset Views
Puamana 254-2 Breathtaking Oceanfront Views form this Lahaina Townhome Incredible Sunsets Steps from the SandWelcome to your Maui Retreat: Puamana 254-2 is a rare ocean-front 3-bedroom, 3-bath townhome that sleeps up to 8 guests and holds a coveted front-row perch to...
Ocean & Diamond Head-view studio in Waikiki
Enjoy stunning ocean and Diamond Head views from your private lanai in the heart of Waikiki. This modern studio is just a short walk to Waikiki Beach, Fort DeRussy Park, world-class Ala Moana shopping center and endless dining. Perfect for couples, friends, business...
Overlook World-Class Golf & Ocean
Welcome to Mauna Lani Point B101, your serene escape where you can unwind with stunning ocean views and enjoy direct access to the world-class Mauna Lani Golf South Course, just steps away. This beautifully renovated residence boasts an open floor plan that seamlessly...
KBM Resorts | 2 Free Cars | Mahana | Whale Watching | 2 Units, 4 Bedrooms | MAH ML-3747
** Limited Time Special Offer: Reserve any KBM Resorts property in Hawaii with an arrival date between now and December 31, 2026 for 6 nights or more and receive a FREE 4-door rental car from top providers--Hertz, Alamo, Avis, or Budget. Convenient airport pick-up and...
Makaha, or “fierce,” is the name of one of the largest valleys on the O’ahu’s leeward coast where our unit is located. Makaha Beach Park, a narrow 21-acre park, lies on the shore of the valley just down the road. The park and its sand beach are bordered on the west by...
A wonderful property for 2 person
Beautiful spacious studio with private entry. Step out into a beautiful terrace of green grass, coconut tree, flowers and fruit trees. One block from the ocean; where during winter time its a Whales and dolphins` hang out. Sea turtle can be spotted all year round. A...
New Listing, Colony Villas 1704, Sleeps 6, WIFI, AC by Coldwell Banker
Tropical Comfort, Luxury at Colony Villas 1704 Welcome to your Big Island getaway at Colony Villas 1704, a beautifully appointed 2 bedroom, 2.5-bathroom townhome nestled within the prestigious Waikoloa Beach Resort. This spacious villa offers the perfect blend of...
Sunset in the Sky | 38th-Floor Waikiki Penthouse
Welcome to your 38th-floor penthouse escape at the Waikiki Sunset Hotel, where island living meets sky-high views. Perched high above Waikiki, this rare penthouse offers sweeping panoramas, cool ocean breezes, and a front-row seat to Hawaii’s most iconic sunsets.Step...
** Limited Time Special Offer: Reserve any KBM Resorts property in Hawaii with an arrival date between now and December 31, 2026 for 6 nights or more and receive a FREE 4-door rental car from top providers--Hertz, Alamo, Avis, or Budget. Convenient airport pick-up and...
Beautiful Waikiki Room w/ Rooftop Pool, 2 Blocks from the Beach - Pets Welcome
Prime Waikīkī Beach location with easy access to shopping, dining and attractions. Relax in contemporary rooms featuring island charm, plus enjoy a rooftop pool and 24-hour fitness center.This listing is for a room within a hotel.✦ Your room is 270 sq. ft, equipped with...
Beachside Kailua Beach House by Gather w/ Pool & Gourmet Kitchen
Just a short stroll from the turquoise waters and powder-soft sands of Kailua Beach, Kailua Beach House is a light-filled 4-bedroom, 2.5-bath island retreat designed for laid-back luxury. This single-level residence blends open-concept living with a private outdoor...
Spacious 2BR Ocean View Condo With ALL Amenities!
Spacious recently renovated FULLY FURNISHED 2br 1.25 ba condo with all amenities located on the Diamond Head side of Waikiki.Breezy 840 SF corner unit on a high floor so you have gorgeous Diamond Head, Ocean, panoramic Ala Wai canal, golf course and mountain views - all...
Maui Resort Rentals: Kaanapali Alii 352/3 - 5th-Floor 4BR Retreat with Ocean and Mountain Views!
This one-of-a-kind 4BR/4BA offering at the acclaimed Kaanapali Alii, set in the heart of Kaanapali Beach, pairs two luxurious neighboring suites into one spacious island retreat. Together, they create an exceptional Maui getaway designed for relaxing, unwinding, and...
Comfy studio in Heart of Waikiki! Quick walk to beach, close to Ala Moana!
Ilikai Marina #1191 – 1765 Ala Moana Blvd.This bright, beautifully updated studio vacation rental is located at the gateway to Waikiki, near Hilton Hawaiian Village. Set in one of Honolulu's most desirable oceanfront locations, this inviting condo offers the perfect...
4BR I Kii Hale at Kukui ula Signature Retreat
Summary:Kii Hale at Kukuiula is a contemporary 4BR, 3BA residence offering a peaceful escape in one of Kauai’s most prestigious neighborhoods. With golf course vistas, a private heated pool, and open-air living spaces, this home invites relaxation in every corner. All...
Wyndham Waikiki Marina | 2 Studio Suites
Summary:Live like a super star when you stay at this resort, which has hosted celebrities, presidents, and jetsetters. You get easy access to Waikiki Beach, the most famous stretch of sand in the Pacific. Surf’s up.Wyndham Waikiki Marina | 2 Studio SuitesEach suite...
Gorgeous Ocean View 3BR 2BA Home, Wailuku, 6 Mo. Min priced below vacation rates
This single family home is being rented out for six months while we travel. Inquiries for less than six months will not be accepted. A home of this size, quality, location, and ocean view would conservatively rent for $350 per night but we're discounting it to $289 per...
** Limited Time Special Offer: Reserve any KBM Resorts property in Hawaii with an arrival date between now and December 31, 2026 for 6 nights or more and receive a FREE 4-door rental car from top providers--Hertz, Alamo, Avis, or Budget. Convenient airport pick-up and...
** Limited Time Special Offer: Reserve any KBM Resorts property in Hawaii with an arrival date between now and December 31, 2026 for 6 nights or more and receive a FREE 4-door rental car from top providers--Hertz, Alamo, Avis, or Budget. Convenient airport pick-up and...
** Limited Time Special Offer: Reserve any KBM Resorts property in Hawaii with an arrival date between now and December 31, 2026 for 6 nights or more and receive a FREE 4-door rental car from top providers--Hertz, Alamo, Avis, or Budget. Convenient airport pick-up and...
Cozy studio- 5 min away from shopping center
Come and stay in a cozy studio located in a quiet suburb of Oahu. You can walk a minute away from the community pool area where you can swim around or just lay down and relax while soaking in all of Hawaii’s sunshine. Drive for 5 minutes to one of Oahu’s popular...
Direct Oceanfront! Sugar Beach Resort, Penthouse in paradise, AC, TV, WIFI, POOL
Welcome to Sugar Beach - the longest white sand beach on Maui! This fully remodeled OCEANFRONT condominium is a Penthouse unit at Sugar Beach Resort (6 floors total) in Kihei, Maui. All new flooring, kitchen, bathroom and appliances!Our condo is one bedroom, one bath...
Honua Kai | 3 FREE CARS | KBM Resorts | Front Alii Suite | 3 Units, 6 Bedrooms | HK ML-3170
** Limited Time Special Offer: Reserve any KBM Resorts property in Hawaii with an arrival date between now and December 31, 2026 for 6 nights or more and receive a FREE 4-door rental car from top providers--Hertz, Alamo, Avis, or Budget. Convenient airport pick-up and...
Newly built 3-bedroom house in beautiful Hilo perfect for a relaxing stay.
Your Hilo adventure begins at this 3-bedroom house. Newly built. Inside, guests find two queen beds and one full bed, perfect for a restful night. With three bathrooms featuring refreshing showers, everyone enjoys plenty of space and privacy. Air fryer oven for crispy...
Aston Maui Kaanapali Villas 110 | Garden View Haven – Pool, Hot Tub & Spa
Maui Kaanapali Villas 110: This sprawling ground-floor condo awaits at the heart of Maui Kaanapali Villas Resort. It boasts spacious rooms with high ceilings and tropical furnishings. This suite can accommodate up to six (6) people. There is a King bed in the primary...
Cozy studio in wonderful Waikiki with refreshing AC breeze
Consider this studio your home away from home while you visit Waikiki. This terrific space features one bathroom and keeps you comfortable with air conditioning. Guests will appreciate thoughtful touches like a hair dryer and iron, making packing light a breeze. Whether...
** Limited Time Special Offer: Reserve any KBM Resorts property in Hawaii with an arrival date between now and December 31, 2026 for 6 nights or more and receive a FREE 4-door rental car from top providers--Hertz, Alamo, Avis, or Budget. Convenient airport pick-up and...
** Limited Time Special Offer: Reserve any KBM Resorts property in Hawaii with an arrival date between now and December 31, 2026 for 6 nights or more and receive a FREE 4-door rental car from top providers--Hertz, Alamo, Avis, or Budget. Convenient airport pick-up and...
Private Paradises, 4BR, Studio, 2 Kitchens
Welcome to Kona in a furnished main house, with an attached studio that elegantly decorated with crafted arts made by my wife, cater for large groups. An unmatched treasure, tropical vibes, 5 minutes from KOA airport:✔ Spacious Three Comfortable Bedrooms – 3 Beds + 2...
One of the absolute best values available at Honua Kai, Hokulani 634 is a full two-bedroom suite with an upgraded interior and panoramic views of the lush West Maui Mountains from its fantastic corner location.When nightfall comes, and it is time to rest and recharge...
🏖️Ocean Front | Fantastic Location - Walk To Kona Town
Oceanfront Ali'i Drive Condo | Walk to Dining & Shops | Kona Ali'i 504Wake up to panoramic ocean views and step into the heart of Kailua-Kona at this fifth-floor oceanfront condo on iconic Ali'i Drive. Watch dolphins, surfers, and unforgettable sunsets from your private...
Kapalua Bay Villa 19G2 Gold Oceanfront 2 Bedroom
- Villa closest to Oneloa Beach- 1st floor villa accessible by 16 stairs from parking lot- Travertine tile floors throughout- Updated open kitchen with granite counters and stainless steel appliances – fridge with ice maker, stove/oven, microwave, dishwasher, cookware,...
** Limited Time Special Offer: Reserve any KBM Resorts property in Hawaii with an arrival date between now and December 31, 2026 for 6 nights or more and receive a FREE 4-door rental car from top providers--Hertz, Alamo, Avis, or Budget. Convenient airport pick-up and...
Charming studio w/ country views!
Beautifully located on half an acre with gated secure entrance. Enjoy a lanai, lots of orchids and peaceful surroundings. Situated on a hill above the street w/views to beautiful vistas, native vegetation and colorful birds. Suitable for 2-3 people.
Idyllic 90 Day North Shore Getaway!
Our hisorical Hale (ha-lei: Hawaiian word meaning home) is a plantation style paradise! Many of the homes in our neighborhood are the original houses for the Kahuku sugar plantation/mill workers. The area is rich in tradition and history. Many of the families have been...
Maui 3 Bedroom Kapalua Retreat Home
Please Send An Inquiry Before Requesting To Book By Clicking The Contact Host Tab.Step through stunning custom wood-and-glass front doors and let your eyes travel straight through the home to the Pacific beyond. Inside, the open-concept living, dining, and primary...
Kuleana Club #615 Oceanfront - 1 bd&1 ba - Gated
Summary:Located on Maui's tropical west coast, the Kuleana Club has a panoramic view of the Pacific and the lovely offshore islands of Molokai and Lanai. This unit is a 2nd floor oceanfront condo, only steps to the ocean, and surrounded by a plush Hawaiian garden. Enjoy...
** Limited Time Special Offer: Reserve any KBM Resorts property in Hawaii with an arrival date between now and December 31, 2026 for 6 nights or more and receive a FREE 4-door rental car from top providers--Hertz, Alamo, Avis, or Budget. Convenient airport pick-up and...