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.
Hapuna Beach Luxury - Private Pool, Maid Service, Resort Access!
Introducing bespoke oceanfront living on one of the most pristine beaches in Hawaii! - C24 at the Hapuna Beach Residences is a luxurious 2-bedroom beachfront condominium with a private pool, adjacent to the Westin Hapuna Beach Hotel and within the Mauna Kea Resort....
❤️PiH❤️ Hono Loa ★ Bikes/Beach Toys ★ Private Beach Club ★
Presented by Paradise in Hawaii Luxury HomesWelcome to Hono Loa at the Fairways in Mauna Lani!Hono Loa offers the ultimate backdrop for your Hawaiian getaway. Perfectly designed to accommodate up to 6 guests, it's an inviting, luxurious, and serene retreat for both...
Kaanapali Maui Eldorado H206 Partial Ocean 1 BD
- 2nd floor condo with balcony- Open kitchen layout with granite counters, stainless steel fridge, stove/oven, microwave, dishwasher, cookware and tableware- 2 king beds- 1200 square feet / 111 square meters- Bathroom with walk-in-shower- Air conditioning- Washer/dryer...
Lani Paradise Oceanfront Villa Paia
Discover paradise in our 4-bedroom, two-story Villa overlooking Maui’s North Shore. Featuring a pool surrounded by breathtaking oceanfront scenery.This exclusive property offers waterfront views of the sought-after surf break, Tavares Bay, with sandy beaches within a...
Luxury Ocean View One Bedroom4U! free WIFI-with pool and sauna 5min to the beach
About this spaceThis brand new listing is designed for extended stay, including tax and electricity. If you inquire for weekly, we can come up with some agreement,upgraded unit. Smooth ceiling. Enclosed lanai. One block from Waikiki Beach. Very desirable building is the...
New-*Summer Special Rates* #8-259-Across from Beach! Next to Food/Shops
*New Listing!*-Owner just updated Aug 2025 with new paint, remodeled bathroom, new ceiling fan, new sleeper mattress, new linens and art and added AC in bedroom.-Peaceful Garden Condo | 1BR/1BA | Walk to Kam II Beach + Dining | Sleeps 4Tucked into the lush tropical...
Upgraded Stunning Ocean View Studio w/Kitchenette, WiFi, A/C- Waikīkī Grand #716
Castle at Waikīkī Grand #716 - Charming and inviting are only two of the many words to describe this ocean view studio with a kitchenette! Wake up to the glow over the rim of Diamond Head Crater from your plush bed with two pillows. This studio provides ample space...
Maui Sunset A412 Beach Front Condo
Maui Sunset A412 Beautiful oceanfront property located in the heart of Kihei! Steps away from the beach. Walking distance to shops and restaurants. Easy access to the highway to road to Hana, Haleakala Crater, Maui Ocean Center, Lahaina and to the Airport.Taxi, Uber,...
Upgraded Waikīkī Studio w/ Kitchenette, AC and WiFi - Bamboo Waikīkī Hotel #703
Castle Bamboo Waikīkī Hotel #703 - Set high on the seventh floor of the amenity-rich Bamboo Waikīkī hotel awaits your own sanctuary offering modern convenience and elegant style that will make your Hawaiian escape a memorable one. Floor-to-ceiling glass sliders...
Aloha from Waikiki! 3 Partial Ocean View Units, Steps to Waikiki Beach Walk
Looking for a beachfront getaway in Waikiki? Look no further than this convenient property! Just minutes from the most popular attractions, the excitement of Waikiki is all around you! And with comfortable amenities and authentic Hawaiian hospitality, you'll have...
Charming 2-bedroom condo with AC, WiFi in delightful Princeville
Welcome to our tropical, sunlit family-home in Paradise! Our corner unit with vaulted ceilings offers privacy, safety & serenity. Perfect for families and travelers alike. Walk to Anini Beach, with its calm waters and snorkeling. Or just take a few steps to the pool!...
2 bm 2bth Westin Princeville Resort Villa Available 7/21-27 only
Situated on the bluffs of Kauai's North Shore, guests can indulge in a Two-Bedroom Villa. This accommodation is comprised of a connecting Studio Villa and One Bedroom Villa to create a spacious 1,311-square-foot personal retreat.Inside this spectacular villa, you will...
🏝️SUMMER-Booking Now Beautiful Oceanview, Great Location Across the Beach🏝️
This beautifully renovated condo boasts a stunning ocean view and is situated across one of the best beaches in Kihei, Kamaole 3 Beach Park. Enjoy the daily sunset from the lanai, whale-watching from December to April while sipping coffee, cocktails, and savoring...
Couples Retreat: Romantic Room with Seafront Sunrise
Discover Waikiki’s charms from our doorstep—steps to Kuhio Beach and Diamond Head. Explore local cuisine, shopping, and vibrant nightlife all within reach.Wake up to mesmerizing ocean views and let the day unfold with vibrant Hawaiian adventures at our beachfront...
Royal Kahana Maui 917 Ocean View Studio
- 9th floor condo with balcony- Updated kitchen with granite counters and stainless steel appliances includes stove, oven, refrigerator, microwave, coffeemaker, toaster, coffee starter kit, blender, tea kettle and complimentary tea- Tile floors in entry, kitchen and...
Royal Kahana Maui 1008 Oceanfront 1 Bedroom
- 10th floor condo with balcony- Updated open kitchen with granite counters and stainless steel appliances includes stove, oven, refrigerator, microwave, coffeemaker, toaster, coffee starter kit, blender, tea kettle and complimentary tea- Tiled entry, dining room,...
Cozy Aloha Suite with AC in charming Kailua
Welcome to our home! We are a legal vacation rental (TA-188-004-1472-01, 90/BB-0102) hosting guests for more than 30 years. We are an environmentally-conscious family doing our share to "Live Lightly" so our natural resources are protected.**PLEASE NOTE: As of November...
Lani Paradise Oceanfront Cottage
Discover paradise in our 2 bedroom cottage overlooking Maui’s North Shore, featuring a pool surrounded by breathtaking oceanfront scenery.This exclusive property offers waterfront views of the sought-after surf break, Tavares Bay, with sandy beaches within a 3 minute...
Hilo Lagoon Retreat – 2BR w/View, A/C, Pool
Relax and Unwind at Hilo Lagoon CenterWelcome to your home away from home in the heart of Hilo! This spacious 2-bedroom, 2-bathroom condo offers comfort, convenience, and beautiful views of the peaceful waters at Wailoa River State Park.The spaceInside, you’ll...
North Shore Oahu | Turtle Bay - Hale Kahakai
Welcome to Hale Kahakai, located in the gated Turtle Bay community in North Shore. You're just a 5 minute walk to a beautiful white sand beach in a cove protected by a natural reef- perfect for children. Arnold Palmer Golf Course, Turtle Bay Resort, and Roy's Beach...
Maui Eldorado C203 Peaceful Paradise Adjacent to C202
Step into your own slice of paradise at Maui Eldorado C203, a spacious one-bedroom, two-bathroom condo surrounded by tropical gardens and island serenity. Recently updated and thoughtfully appointed, this relaxing retreat offers sweeping views of the island of Lanai,...
Kanaloa at Kona Oceanfront 2 Bedroom + Loft
- Oceanfront condos with loft located on 2nd floor- Kitchen features stovetop, oven, refrigerator, microwave, dishwasher, coffeemaker, blender, disposal, cookware and tableware- Private balcony with wet bar- Master bedroom with 1 king bed or 1 queen bed and private...
New Listing, Beach Villas Kahaluu, 4ppl OceanView
Beach Villas at Kahaluu – Ocean-View Retreat Across from Snorkeler’s Paradise Aloha and welcome to your Big Island getaway! Nestled right on iconic Alii Drive, this 1-bedroom, 1-bathroom ocean-view villa offers the perfect blend of comfort, location, and tropical...
Awesome access to Beach 1min!Studio in Hotel&Condo
【Basic Info】This is a private studio unit in Waikiki!!You can enjoy your stay by yourself, friend or partner. The condominium is located east area in Waikiki.This area is really closed to the Diamond Head, Kapi olani Park.You can enjoy a walk while feeling the...
Royal Kahana Maui 215 Ocean View 1 Bedroom
- 2nd floor condo with balcony- Tile & Vinyl plank flooring throughout- Fully equipped kitchen with– fridge, stove/oven, microwave, cookware, tableware- Tiled bathroom with walk-in pebble shower with grab bar- Queen sofa bed in living area- Central Air Conditioning-...
Makaha Vista Villa - Pool, Amazing Views
Welcome to your private Hawaiian escape on the beautiful west side of Oahu—a stunning 4-bedroom, 3.5-bath estate offering 4,000 square feet of beautifully designed living space. Set in a quiet, upscale neighborhood where homes are generously spaced for maximum...
Kapalua Bay Villa 36B4 Oceanfront 1 Bedroom
- Villa closest to Oneloa Beach- One level condo with no stairs between parking and the front door- Travertine tile floors in living room, dining room, kitchen; porcelain tile in bathroom and carpet in bedroom- Updated white kitchen with granite counters includes...
Sunset/Ocean Views, Two pools, BBQ, Golf, Quiet
Welcome to your Waikoloa escape - a peaceful condo retreat w/ ocean views, modern comforts & resort-style amenities just minutes from Hawaii’s best beaches:• Sleeps 2 | 1 bedroom | 1 bed | 1 bath• Pools & hot tub year-round w/ tropical garden setting• Private...
Pacific+Pool+Palms! Luxe w/Chic Kitchen, Lanai, Den, WiFi–Kauai Kailani K303
You may never want to leave the oceanfront lanai of this 864 sq ft Kauai vacation home! Prepare meals in the upgraded kitchen with dishwasher, and then relax with WiFi and a flat screen TV. Other conveniences include a private den and ceiling fans. Sleeps 4 guests in...
Hana Hou Hale Pacific Ocean Front Villa and Guest House
Poipu Hana Hou Hale & Ohana is THE vacation home of your dreams. Situated in sunny Poipu, with first-class views of the sparkling Pacific, this picturesque home is equipped with everything you need for an unforgettable stay on Kauai. Enjoy uninterrupted sunrise and...
Marriott Maui Ocean Club - 2 Bedroom/2Bath Ocean Front in Lahaina Tower
Welcome to this charming condo in Lahaina with private lanai's at the luxurious, five star Marriott's Maui Ocean Club Resort. This amazing property features 2 bedrooms with a king bed and a full bed, along with 2 bathrooms equipped with a jetted bathtub in the master...
Kihei Maui, 2 Br, Unit#2n
Your family will be close to everything when you stay at this centrally-located place....................................................................................................................
Stunning Lanikai studio - 5 min walk to Kailua and Lanikai Beach!
Beautiful hillside studio with breathtaking ocean views. Wake up to spectacular sunrises, watch the whales play, and enjoy the ocean breeze as you live the Lanikai lifestyle. Complies with Hawaii law.
NEW LISTING! Offering limited time introductory rates! Luxury Remodeled Townhouse with Breathtaking Golf, Mountain & Partial Ocean Views
NEW LISTING! Offering limited time introductory rates! Enjoy the 5th Night Free for stays between now and December 15, 2025. Reservations must be made by August 31, 2025. *Applies to new reservations only. Property Highlights • Luxury remodeled townhouse offering...
Your Hawaiian Escape Awaits – The Grand Waikikian - 2 Bedroom Partial Ocean View
Welcome to The Grand Waikikian by Hilton Grand Vacations Club, where your Hawaiian dream vacation comes to life! Located within the famous Hilton Hawaiian Village® Waikiki Beach Resort, this upscale paradise is the ultimate destination for families looking to...
Royal Kahana Maui 912 Oceanfront 1 Bedroom
- 11th floor condo with balcony- Vinyl plank flooring throughout- Fully equipped kitchen with– fridge, stove/oven, microwave, dishwasher, cookware, tableware- Tiled bathroom with walk-in tiled shower- 1 king bed and twin sofabed- Washer/dryer in unit- Central air...
'Olina NEW (PKC 106) ~ 3 BR ~ Ground Floor ~ Pool
Summary:'OLINA, Puako Condo 106 is a ground floor unit that was designed with great attention to detail for a clean modern style and high quality feel throughout. The unit stays cool with two A/C units (one in the main bedroom and one for the living room kitchen) and...
Royal Kahana Maui 606 Ocean View 1 Bedroom
- 6th floor condo with balcony on the north side of the building- Updated open kitchen with granite counters includes stove, oven, refrigerator, microwave, coffeemaker, toaster, coffee starter kit, blender, tea kettle and complimentary tea- Tile flooring throughout-...
Royal Kuhio 1707 - Spacious Studio w/ Diamond Head and City Views in Waikiki
Heart of Waikiki - Royal Kuhio (17th Floor)Address: 2240 Kuhio Ave., #1707, Honolulu, HI 968151 Bed | 1 Bath | Sleeps 4Beds: 2 Full-size beds + 1 Queen sofa bedSize: 436 sq ft + 80 sq ft lanaiKitchen: Fully equipped with oven, microwave, modern appliances, cookware, and...
Raintree Kona Reef, Hawaii Timeshare Rental Second
This is a highly rated resort on Kona, the Big Island in Hawaii. Kona Reef is an oceanfront resort with a private beach and is rated 8.4 by Bookings.com and 8.6 by Expedia, because of its beautiful ocean setting and surroundings . The resort also has a central pool with...
Poolside Paradise: with Double Bay View Rooms (Unit C)n
The newly renovated multi-level luxury estate between Kaneohe and Kailua offers a shared living experience that is second to none. With its location overlooking the Kaneohe Bay Yacht Club and easy access to the H3 freeway, this fully furnished 5,400 sq. ft. home...
Kaanapali Alii | 333
Located on the third floor and in the building on property closest to the ocean, you will be able to hear the sounds of the waves crashing on Kaanapali Beach just outside your vacation rental. Engage more of your senses and head out to your private lanai where you can...
Wailea Ekahi Village | 52D
Wailea Ekahi 52 is a luxurious vacation rental property located in the heart of the idyllic Wailea resort community on the southern shores of Maui. This spacious, one-bedroom, one-bathroom condominium offers guests a serene and indulgent island getaway, with all the...
Waterfront studio with mountain view, rooftop pool, hot tub, sauna & central AC
Honolulu Horizon Haven-30 night minimumOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Perched high above the bustling city of Honolulu in Waikiki, this stunning condo offers a...
Sunset Shores - UNIT B Kauipoho
Summary:Relax with the Escape to serenity in this shared Kailua Kona space. Embrace the tranquil island ambiance and inviting interiors.With convenient beach access, this is an ideal location for a peaceful coastal getaway. Immerse yourself in the beauty of Hawaii and...
Just Listed! Top Notch Rental Experience Awaits!
Experience breathtaking sunsets every evening from your private lanai and immerse yourself in the fresh ocean air at Kaleialoha 213. This West Maui vacation condo is perched right on the water's edge, offering unparalleled proximity to the ocean. The property boasts a...
Views on the Kaanapali Coast!
Prepare to be completely swept away by the breathtaking beauty and boundless excitement that awaits you on the island of Maui, your best vacation yet! At the beachfront retreat of Paki Maui, the azure waters of the Pacific Ocean gently caress the golden sands just steps...
Hale O Ka La – Luxury Villa at Mauna Kea Resort
MEET THE VILLAHale 'O Ka La on the Big Island defines Hawaiian luxury. Developed by Laurance S. Rockefeller in the 1960s, Mauna Kea Resort was the Kohala Coast's first luxury destination and remains an icon of island elegance.This stunning 5,358 sq. ft. estate features...
Kapalua Ridge Villa 124 Gold Ocean View 1 Bedroom
- Villa is closest to Oneloa Beach- Second floor unit with 15 stairs from parking to the villa- Tile flooring in kitchen, bathroom and carpeted in living room and bedroom- Fully equipped kitchen with stainless steel appliances includes stovetop/oven, microwave, and...
Quiet Condo, Gorgeous Views, Golf Course, 2 Pools
Welcome to your island retreat in Waikoloa Village - a bright, airy condo w/ ocean views, resort-style amenities & a prime location near beaches & shops:• Sleeps 4 | 2 bedrooms | 2 beds | 2 baths• Shared pools, hot tubs & tennis courts• Private lanai w/ sunset &...