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.
2BR Ocean View condo resort in Princeville. Private path to walk to the beach!
This condo is located in Hanalei Bay Resort and is available for both Christmas week and New Years weeks this year December 20, 2025 to January 3, 2026. Best price per night is staying all 7 nights each week Saturday to Saturday. If you are looking to stay at a place in...
Lodge at Kukui'ula Villa 2 - 4 Bedroom Villa - Platinum
The four-bedroom villas at The Lodge at Kukui'ula on Kaua'i offer luxurious accommodations and exclusive access to the award-winning private club facilities and amenities of The Club at Kukui'ula, including the 18-hole Tom Weiskopf–designed golf course, sprawling spa...
Oceanview Retreat Walk to Beach & Restaurants
Summary:Prime Location Walk to beach dining shopping Breathtaking Ocean Views Enjoy from private lanai Luxury Memory Foam Bed Sleep like royalty Fully Equipped Kitchen Cook with ease Resort Perks Pool hot tub BBQ grills Exclusive Coupons Save 1000 on Maui activities...
Ocean-City Luxurious Vacation at the Sky Ala Moana with Amazing Amenities
This property requires a minimum 30-day rental. Book with confidence—professionally managed by Ali'i Beach Rentals, an award-winning property management company.The Sky Ala Moana is Honolulu's newest symbol of luxury, featuring two distinct towers: The Residence and The...
Maui Ka’anapali Villas #205: One bedroom ocean view on N. Kaanapali Beach
Maui Ka’anapali Villas #205: One bedroom ocean view on N. Kaanapali Beach with Pool and Beach Access. Maximum occupancy: 2Bed size: King BedAC: Central ACOffice space: Desk and desk chairBright, open and spacious one bedroom condo with ocean views. The expansive shared...
Oceanfront Top Floor - Pools, Hot Tub, Central AC
Welcome to Kauai Beach Resort, the ideal oceanfront hideaway for the vacationer looking for a dream escape to Kauai, The Garden Isle!Highlights: -4 lagoon-style pools, 2 hot tubs & a waterslide-Poolside tiki bar + on-site restaurants-Hawaiian Rainforest Spa, fitness...
Honua Kai Hokulani | 2 Free Rental Cars | KBM Resorts | Large Floorplan | 2 Units, 4 Bedrooms | ML-1790
** 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...
Elegant Waikiki Retreat - Ocean View & Luxe Decor
Experience refined island living in this modern Waikiki condo with an ocean view. Designed for the discerning traveler, the space features SoHa Living décor, Nordstrom and Neiman Marcus-inspired furnishings, and Cozy Earth luxury linens. Enjoy a private lanai, stylish...
Island Comfort: 2BR at Wyndham Kona Coast Resort
Enjoy your Hawaii retreat in this spacious two-bedroom suite at Wyndham Kona Coast Resort, designed to accommodate up to six guests. The villa includes two separate bedrooms, a full kitchen with modern appliances, two bathrooms (one with a whirlpool tub in many suites),...
Breathtaking Ocean Views, You'll Never Want To Leave Waikiki!
Construction Notice 10/20/25: Exterior painting work is currently scheduled from 10/29 - 12/12/2025. During this time, the lanai will be locked and not accessible to guests. For your safety, please do not attempt to use the lanai at any time. You may also hear...
Oceanfront Retreat! Near Waihee Coastal Dunes and Wetlands Preserve, Pool
Our spacious suites with private lanais offer breathtaking views of the pristine shoreline, courtyard, or garden, providing the perfect backdrop for relaxation and adventure. Stay connected with high-speed internet, unwind in our unique whale-shaped outdoor swimming...
The Islands at Mauna Lani M1
Tropical furnishings, island-inspired wall art, and blonde wood flooring combine to make the Islands at Mauna Lani M1 a welcoming and relaxed vacation rental option on the Island of Hawaii. This two-bedroom two and a half bathroom split-level townhouse is perfect for...
Kaanapali Alii Residence 3106
Kaanapali Alii 31062 Bedrooms | 2 Bathrooms | Sleeps 6 | Ocean Front________________________________________Welcome to 3106, a gorgeous condominium in Maui's exclusive Kaanapali Alii Resort. This deluxe residence offers stunning, unobstructed views of the sparkling...
Glamping in Glenwood
This luxurious tent is located in the lush rainforest of Volcano, Hawaii, and provides the perfect setting for a romantic getaway, solo traveller, or just a place to detach from your every day bustle and hustle. Inside, the tent boasts a contemporary interior with a...
Pali Ke Kua 9 - 2Br Townhouse - Mountain Views, Pool, Hot Tub
Beautiful Hawaiian Condo with Mountain Views, Pool, & Hot Tub - Steps to BeachNestled in the picturesque town of Princeville, Hawaii, and a short drive to the world famous Hanalei Bay, this charming 2-bedroom, 2-bathroom townhouse-style condo at Pali Ke Kua offers a...
Kai Lani Luxury 6D by Gather: Ground-Level 3BR w/ Ocean View Lanai
Set within Ko Olina’s premier oceanfront community, Kai Lani Luxury 6D by Gather offers a serene single-level retreat where tropical landscapes, gentle ocean breezes, and modern comforts blend seamlessly. This three-bedroom, two-bathroom villa spans 1,320 sq. ft. and...
Aqua Aloha Surf Waikiki 301 Moderate Studio with Partial City Views, Sleeps 2
Aqua Aloha Surf Waikiki 301 Moderate Studio with Partial City Views located just 2 Blocks to Waikiki Beach, (2) Twin beds, Sleeps 2, 222 Sq FtAqua Aloha Surf Waikiki brimming with island personality offers a range of accommodations that are perfect for couples and solo...
Honua Kai Hokulani | 2 Free Rental Cars | KBM Resorts | Family Friendly | 2 Units, 3 Bedrooms | ML-1355
** 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...
NEW! KBM Resorts | Ocean Views | FREE CAR | Wailea Ekahi | 1-Bedroom Condo with Luxury Amenities! WKV-45C
** 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...
Beachfront, spacious, absolutely stunning Oceanfront Condo with FREE Parking
Aloha! Our spacious Fourth floor 1 bed 1 bath condo with spectacular views of the beach, ocean and Molokai & Lanai islands awaits your Hawaiian adventure. Enjoy the sights and sounds & breeze of the Pacific Ocean from the living room & kitchen! You can't miss watching...
Poipu Beach• AC• Walk Out• 3-Min to Beach • Pool • Surf School• Snorkel• Turtle
Welcome to your peaceful Poipu Beach retreat — a perfectly located, ground-floor walkout condo just a short 3-minute stroll through lush, tropical gardens to the shoreline. Set in one of the most walkable and convenient areas of Poipu, this home offers a calm, breezy...
Beachfront is set amid palm trees on 6 acres of beautifully landscaped gardens!!
Situated on eastern Kauai's Coconut Coast. This beachfront property is set amid palm trees on 6 acres (2.4 hectares) of beautifully landscaped gardens. The guest rooms are designed in island-inspired decor. On-site amenities include a pool, jet spa, poolside bar, and...
Grand Opening Prices! Ocean Views! Steps 2 Beach!nEntire condo in Kihei, Hawaii!
Welcome to our slice of heaven - Pineapple Paradise! Our recently remodeled condo boasts a peaceful, laid back vibe, making it the perfect choice for a relaxing getaway to escape all your cares.This gem—steps from the beach—is tucked away from the hustle and bustle of...
Elegant luxurious hillside retreat with awe inspiring panoramic ocean and mountain views. 90 day minimum rental.
Nestled on the tranquil hillside of the distinguished Mahinui neighborhood, Hale Kalia is nothing short of a refined sanctuary where modern luxury meets island serenity.Nestled along the tranquil windward coast of O‘ahu, the Mahinui neighborhood in Kāne‘ohe offers a...
Lodge at Kukui'ula Villa 3 - 4 Bedroom Villa - Platinum
Vacationing in Villa 3 at The Lodge at Kukui'ula offers a luxurious experience nestled in the heart of Kaua'i's stunning South Shore. This exceptional accommodation provides guests with an authentic Hawaiian retreat featuring sophisticated plantation-style architecture...
Waikiki Shore 518 Partial Ocean View 2 Bedroom
Located in the only condominium building on Waikiki Beach, this two bedroom, two bath condo offers partial ocean views and all the comforts of home. Perfect for families or couples traveling together, it’s just steps from the shoreline, shops, and dining.Unit 518 Ocean...
Sands of Katana Vacation Club, Hot Tub, Pool!
Midway between the world famous Kaanapali and Kapalua beaches lies the Sands of Kahana Vacation Club. The perfect laid-back retreat, this resort is equipped with everything you need to experience a true picture-perfect vacation. Spend mornings walking on the beautiful...
The Gardens at West Maui 1BR Suite
Located in breathtaking West Maui, within close proximity to wonderful beaches, quaint shops, and fine restaurants, The Gardens at West Maui offers delightful accommodations in a gorgeous tropical setting. Our 33 guest units are spacious, comfortable, and come with...
Kapalua Bay Villas | Panoramic Ocean Views 2-bedroom Luxury Maui Villa | 2 Units, 3 Bedrooms | KBM Resorts | KBV ML-2005
** 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...
Kapalua Bay Villa 19G5 Gold Oceanfront 1 Bedroom
- Villa closest to Oneloa Beach- Split level condo with 19 stairs between the driveway and front door- Tile entry, kitchen and bathrooms, carpet in living area, dining room and bedroom- Living room, kitchen and ½ bath on first floor; bedroom, full bathroom and laundry...
2-Bedroom Condo near Downtown Kona | Close to Beaches & Dining
This bright and breezy 2-bedroom, 2-bath condo is perfectly located in the heart of Kailua-Kona. Located on Ali‘i Drive, you`re just minutes from beaches, shops, and restaurants, it’s the ideal spot to relax after a day of island adventures.Features:- A/C- Full kitchen...
34th FL Allure Waikiki | Parking | Pool | City & Mtn Views
The Space: This beautifully appointed 2-bedroom, 2-bathroom suite features floor-to-ceiling windows throughout and a curved lanai with incredible panoramic views. Located on the 34th floor of the luxury Allure Waikiki tower.Master Suite: King bed, ocean views, walk-in...
Waikiki Ocean City View 2 Bedroom 2 Bath
Summary:Newly Renovated Waikiki Split 2BR/2BA Efficiency Unit. Free garage parking.The Space:Reconnect with loved ones in this family-friendly place. Situated at the entrance of Waikiki, our delightful split 2Br 2BA efficiency unit in the Hawaiian Monarch building...
Island Living w/Ocean Views, Wi-Fi and Pools-G510A
Your Hawaiian dream vacation becomes a reality when staying at this tropical oasis set within walking distance to the iconic Maui shores. The Maui Banyan resort is sprawling with lush flora and top-notch amenities including two swimming pools, jacuzzis, tennis courts,...
Walk to Beach | Updated Condo w/ AC + Pool | Prime Kihei Location
Large two-bedroom condo with a loft with ocean views. This vacation rental features a queen bed in the master bedroom, two twins in the loft bedroom, and a pull-out sofa bed in the living room. This unit looks out over the pool. Relax on the lanai and enjoy paradise....
Vacation at Ko Olina Hillside Villa 1528-4
Resort in Kapolei with a water park and a fitness centerA water park, a fitness center, and a hot tub are available at this smoke-free resort. Other amenities include laundry facilities. Limited housekeeping is available. Air-conditioned accommodations at this resort...
Diamond Head 1 Bedroom Condo Queen Bed & Bunkbed
Legal Vacation Rental - This beautifully furnished 1 bedroom suite with Queen bed & with separate living room offering twin bunkbeds.The full kitchen is bright spacious and well equipped. Condo has awesome views out over the Ocean and also Kapiolani Park - Includes flat...
Fabulous 7 bedrooms for 16 above famous Anini Beach!
Listing provided by "The Vacation Rental Experts". Contact directly for more options!This fabulous 7 bedrooms and 5 baths for 14 to 16 people, is situated right above famous Anini Beach, with an 8-10 minute walk down the Anini Beach trail just steps away from the...
Kaanapali Alii Residence 264
Kaanapali Alii 2642 Bedroom | 2 Bathrooms | Sleeps 6 | Mountain ViewKaanapali Alii 264 is an elegant one-bedroom mountain view condo with a fully enclosed den that comfortably serves as a second bedroom. This deluxe residence offers sweeping views of the West Maui...
Sea Village 4113 Oceanfront Condo Kailua-Kona, HI
Our privately owned unit is within Sea Village, a Condominium complex less than 1 mile from downtown Kailua-Kona. We love this location because it's in between the great surfing and snorkeling to the south, and the white sand beaches to the north. This unit has the most...
Mauna Kea Ocean House
Step into island luxury at Mauna Kea Ocean House, a breathtaking estate tucked within the exclusive community of Hapuna Estates at Mauna Kea on Hawaii's Big Island. This spacious home sits on over an acre of beautifully landscaped land with panoramic ocean views,...
Kilipue Retreat by Gather | Luxe 3BR Home w/ Fenced Yard Near Ko Olina
Kilipue Retreat places you at the quiet end of a Kapolei cul-de-sac, minutes from beaches and big-city conveniences yet wrapped in the calm of a residential neighborhood. Newly refreshed and fully furnished, this 3-bedroom holiday home welcomes corporate guests,...
Hale Pau Hana #707 Ocean Front, Central AC, Oceanfront Complex
Hale Pau Hana #707 is a 2 bedroom, 2 bath unit on the 7th floor with a panoramic ocean view and central A/C throughout. It provides a fully-equipped kitchen, 2 flat-screen TVs, and free WIFI. Go to sleep in your comfortable cal king bed as you enjoy the sound of the...
Indulge in Home-Like Comfort Rooftop Swimming Pool and Hot Tub!
Family-friendly property located just steps from the beachThis listing is for a room within a hotel.✦ Your room is 443 sq. ft, equipped with complimentary toiletries, kitchen with basic amenities, high definition 32-inch TV, available with Premium cable, ensuring...
2bd/2Bath condo Sleeps 6 in Kailua-Kona with central AC across Magic Sands Beach
Escape to this condo in picturesque Kailua-Kona. Guests enjoy two comfortable bedrooms, featuring one queen bed and one twin bed, plus a cozy living room with a sofa bed for extra space. The two bathrooms offer both a bathtub and a shower, perfect for relaxing after a...
Gorgeous Beachfront Nanea Resort+Amenities. 3BR Suite
𝐕𝐢𝐬𝐢𝐭 𝐅𝐢𝐧𝐝𝐢𝐧𝐠 𝐌𝐞𝐢𝐥𝐢 to enjoy 𝐄𝐱𝐜𝐥𝐮𝐬𝐢𝐯𝐞 𝐒𝐚𝐯𝐢𝐧𝐠𝐬 on this elegant, 𝐬𝐩𝐚𝐜𝐢𝐨𝐮𝐬 3-𝐁𝐞𝐝𝐫𝐨𝐨𝐦 𝐎𝐜𝐞𝐚𝐧𝐅𝐫𝐨𝐧𝐭 𝐕𝐢𝐥𝐥𝐚 at one of Maui’s most exclusive 𝐁𝐞𝐚𝐜𝐡𝐟𝐫𝐨𝐧𝐭 𝐑𝐞𝐬𝐨𝐫𝐭𝐬 — 𝐓𝐡𝐞 𝐖𝐞𝐬𝐭𝐢𝐧 𝐍𝐚𝐧𝐞𝐚 𝐎𝐜𝐞𝐚𝐧 𝐕𝐢𝐥𝐥𝐚𝐬.Unlock 𝐌𝐞𝐢𝐥𝐢 𝐌𝐞𝐦𝐛𝐞𝐫-𝐎𝐧𝐥𝐲 𝐑𝐚𝐭𝐞𝐬 & 𝐔𝐩𝐠𝐫𝐚𝐝𝐞𝐬Guests booking through 𝐅𝐢𝐧𝐝𝐢𝐧𝐠 𝐌𝐞𝐢𝐥𝐢...
Waikiki 2 Bedroom w/ Covered Parking, Family Condo
2 bedroom, 1 bath, with your assigned gated parking in Waikiki!! Royal Aloha, 625 sqft w/50 sqft Lanai located on the 3rd floor condo with cityscape views. Short stroll to beach, dining, and shopping. Fast internet. Washer/dryer on every floor.Royal Aloha building is...
Charming Palm Suite at The Imperial Hawaii Resort
Honolulu is waiting for you at this enchanting 1-bedroom apartment. The cozy bedroom features a queen bed, perfect for a good night's sleep after a day of exploring. With 2 bathrooms and a living room with a murphy bed and sofa bed, there's plenty of space for guests to...
Hotel Room Partial Ocean View w/ WiFi and AC - Bamboo Waikīkī Hotel #1101
Castle Bamboo Waikīkī Hotel #1101 - Get the most from your magical Hawaiian experience in this cozy eleventh-floor unit located just blocks from the iconic shores of Waikīkī. With resort-style amenities and a prime location at the Bamboo Waikīkī, you’ll have everything...
Maui Banyan T105 Garden View Condo in Kihei Close to Kamaole Beach II with AC
Welcome to Maui Banyan T105, a serene 1-bedroom, 2-bathroom condo in the heart of Kihei, Maui. Perfect for up to four guests, this bright and comfortable retreat offers a relaxing island escape just across the street from Kamaole Beach II.• Spacious 1-bedroom,...