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.
Upscale Kailua Getaway: Steps to Swim Beach!
An unforgettable Hawaiian escape awaits at this luxurious 3-bedroom, 2-bathroom Kailua vacation rental home! Sip your coffee on the deck, then walk to Lanikai Beach to enjoy the morning waves. Spend your days relaxing in the private pool, lounging in the hammock, or...
First-floor condo across from Magic Sands with balcony, pool & sauna
White Sands Resort #108Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'The soft, white sand of Magic Sands Beach Park is right across the road from this completely remodeled...
NEW! 3/BR Coffee Estate with Hot Tub and Ocean View in Kona town
Aloha!! We are new to VRBO but have 25+ 5 star reviews on another popular vacation rental platform. This is truly a unique property and I have no doubt that you will enjoy your stay! This Kona coffee estate is located just minutes from downtown Kona. Centrally located,...
Hale Malanai*Stairway to Heaven*Huge Views*Steps to Baby Beach
YouTube Video Presentation - https://youtu.be/p-Z6fAoScHQYou walk up the staircase and are immediately pulled by the huge ocean view onto the lanai. The jungle like foliage, the smell of plumeria, the ocean and the sky enchant you as the tradewinds of this perfect...
Loko Kai Nani - Stunning Lagoon Views, Pool, A/C
Welcome to Loko Kai Nani, the Beautiful Lagoon! Look no further. For the Ultimate Big Island Experience. Beats any Hilo Hotel by a mile (IMHO) Fully Air Conditioned, 24 hour security, Everything is Brand New.First time offered, fully renovated with brand new...
Aloha Condos, Kanaloa at Kona, Condo 1901, Oceanfront, AC
Unit 1901 in Kanaloa at Kona is a beautiful two-bedroom, two bathroom, groundfloor oceanfront condo with a fully equipped kitchen, TV in three rooms, ceiling fans throughout and air conditioning. • Oceanfront Location• Sunset Views Year Round• Quiet, Residential...
New Listing! Waikoloa Fairways 2-bed, 2.5-bath unit with pool, BBQ, and lanai
New Listing! Relax at this two-bedroom, two-and-a-half-bath Waikoloa Fairways unit in the heart of Waikoloa Village. The primary offers a soaking tub. Enjoy the open living layout, outdoor wet bar, and large lanai. Pool, hot tub, and BBQ at the complex.Upon entry, you...
Kamaole Sands 6-110 3 bed 2 bath Luxury Tropical Oasis split AC W/D
***MAUI PROPOSED VACATION RENTAL BAN WILL NOT GO INTO EFFECT UNTIL 2030 IN THE UNLIKELY EVENT IT PASSES- YOUR BOOKING IS SAFE!! Elevate your Maui experience at highly renowned Kamaole Sands resort condo. Lush, tropical grounds, swaying palm trees, waterfalls and ponds...
Ocean front! 20' from water, downstairs unit. True beachfront, Pikake. No fees!
Escape to paradise with our ground floor condo at The Pikake in Maui! Enjoy the ultimate beachfront experience in this one-bedroom, one-bathroom retreat located on the desirable West side of Maui between Lahaina and Kapalua. With no deposits, resort fees, or check-in...
Spacious 2 Bedroom 2 Bathroom City View Condo at the Ilikai Hotel
Experience the beauty of Waikiki with Happy Vacations, a short-term vacation rental company! Our team is excited to offer you a modern condo at the renowned Ilikai. You'll love the open floor plan with lots of natural lighting, a spacious balcony, AC, and thoughtfully...
Paradise on park like estate with beautiful ocean and mountain view
Envision time on 45 acres of a landscaped park-like estate bordered by two streams - one is seasonal with a forty foot waterfall. Imagine picnicking by the stream or going for leisurely walks. The 800 plus square foot guest house provides privacy and space to relax....
Take-it-easy Waikīkī Beach Condo
Stay close to Waikīkī Beach, KūhiŠBeach Park and Kapiʻolani Park. Our newly-renovated 2-bedroom 2-bathroom beach pad is in a secure building with free parking. Highlights include a balcony with dining area, full kitchen, beach gear, kids accessories and a washing...
Gorgeous 3 Bedroom Condo as Close to the Beach as You Can Get!! 30 day rental
Perched on the top floor of Foster Tower, this stunning three-bedroom penthouse offers an elevated island living experience with sweeping panoramic views of the Pacific Ocean, Diamond Head, and the Honolulu skyline. Designed for those who appreciate sophisticated...
Gorgeous Keauhou Resort Condo!
**Please note, effective Jan 1st. 2026, Hawaii's Transient Accommodations Tax will increase from 10.25% to 11% for all stays with an arrival in 2026 forward. We may need to collect the tax difference to secure and finalize your booking. We will contact you to confirm...
Dreamy condo near the ocean with pool, hot tub, lanai, fast WiFi & beach toys
Hali'i Kai 8EOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!' When it comes to experiencing the Big Island in style, look no further than this fantastic condo perched in the highly...
Beautiful 3 Bedroom Rainforest Retreat, minutes from HVNP
Come and enjoy our beautiful retreat, just minutes from Volcano Village and the world renowned Hawaii Volcanoes National Park. Designed by renowned local architect, Boone Morrison, this unique property features lots of natural wood and light, providing a wonderful...
Single-level, dog-friendly home with a full kitchen, washer/dryer, patio
Puni Mauka | 31- Day MinimumOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Located less than three miles from the ocean, and just a few miles from the heart of town, this secluded,...
3982S Kalakaua Gorgeous Princevile Studio
Raise your vibes and take in the natural beauty and gorgeous architecture of this Island Style Home, built by a master carpenter.This spacious studio attached to the main home is located in a peaceful cul-de-sac near Queen's Bath, Hanalei Bay, and the forthcoming...
3982 Kalakaua 4br 3ba Home in Princeville
Raise your vibes and take in the natural beauty and gorgeous architecture of this Island Style Home, built by a master carpenter. This spacious property is located in a peaceful cul-de-sac near Queen's Bath, Hanalei Bay, and the forthcoming world-class wellness resort...
3982 Kalakaua 3Br 2Ba Beautiful Princeville Home
Raise your vibes and take in the natural beauty and gorgeous architecture of this Island Style Home, built by a master carpenter.This spacious property is located in a peaceful cul-de-sac near Queen's Bath, Hanalei Bay, and the forthcoming world-class wellness resort...
Sunny Kailua Home w/ Covered Lanai 1 Mi to Beach!
Say aloha to this beautiful vacation rental in east Oahu! This Kailua home features 3 bedrooms, 2 bathrooms, a well-equipped kitchen, and a peaceful yard, making it the perfect home base to explore the island. Whether you're hoping to hike, swim, or learn to hula dance,...
Honua KAI- HK 314-1 BEDRM-1 Bath-⭐️⭐️⭐️⭐️⭐️ 67 Five Star Reviews-Ocean & MNT Views
Aloha, Our condo (Hokulani 314) has just been newly upgraded and remodeled with new furnishings and wall art. Our beautiful one bedroom unit has a king bed and living room with a Queen sofa bed. The condo comfortably sleeps up to 4 guests and is located in the beautiful...
Serene Ocean Vw, Pool, 1Bd/1Bth 20% off Feb - Apr
Keep your eye open for last minute discounts!Kai Moana Hale is a one bedroom one bathroom unit on the second story of a two story building. This is a well appointed and very lovingly updated condo that the owner stays in often. The kitchen is set up for cooking just...
Maui Resort Rentals: Honua Kai - 4 Total Bedrooms, 7th Floor Deluxe Ocean AND West Maui Mountain Views
This tandem one-of-a-kind 4BR offering combines one of Honua Kai's highly sought after deluxe ocean view 2BR corner suites with a neighboring 2BR. Your party will enjoy stunning 7th-floor direct ocean views in addition to views of the majestic West Maui Mountains. The...
Maui Resort Rentals: Honua Kai - 4 Total Bedrooms, Stunning 3rd Floor Ocean Views!
This unique offering combines two neighboring 3rd-floor two-bedroom suites to create an exceptional four-bedroom package that is perfect for large families or groups. Located only one stack back from the oceanfront, Konea 303 provides stunning views of the blue Pacific...
Maui Resort Rentals: Honua Kai - 9 Total Bedrooms, Over 6000 Combined Sq. Ft., Gorgeous Oceanfront Views!
This remarkable nine-bedroom offering brings together four neighboring suites to offer a total sleeping capacity of up to 28 guests. Perfect for large groups or families, this premier offering allows guests to enjoy the space of a luxury home with all the advantages of...
Oceanfront Condo- Gorgeous Ocean Views! Sleeps 4
Aloha and welcome to Hale Ono Loa 303! Hale ono loa means "house of good living" in the Hawaiian language, and that's exactly what you'll find in our condo! Between breathtaking views, a comfortable king sized bed, and a communal pool amongst countless other amenities,...
Two Adjoining Luxury Homes in Mauna Lani - 12 bdr, 2 heated pools, 16,000 sqft
Blue Lagoon (7 bedrooms) and Blue Oasis (5 bedrooms) share a property line and a private putting course with gated paths connecting the two homes.With 12 bedrooms, 13 bathrooms, 2 heated pools and 2 hot tubs, these homes are dream setup for a large gathering, a wedding...
Luxury Villa: Hilton Pool Passes, Renovated, Private Beach Club, Sunset Views
Enjoy staying at the best location at Golf Villas, featuring ultimate privacy with breathtaking sunset views and unlimited access to a private beach club and unlimited access to the Hilton Pool for 6 people. Our well-appointed and recently renovated villa is located in...
2 Bedroom Condo On Hawaiian Beach - Family Friendly - 7 nights
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,...
15 Steps to the Beach! Ground Floor Completely Renovated on the North Shore
Escape to our brand-new, ground-floor North Shore condo, just 15 steps from the sand! This beautifully renovated beachfront unit sleeps 4 and offers direct access to a pristine, turtle-populated beach from your private lanai. Enjoy modern amenities, ocean sounds, and...
Maui Resort Rentals: Honua Kai - 4 Total Bedrooms, Stunning 3rd Floor Interior Courtyard Ocean Views!
This premier tandem offering encompasses two expansive 3rd-floor interior courtyard two-bedroom suites situated directly next door to each other and are the perfect place for your group to gather, reconnect, and celebrate. Occupying a fantastic interior courtyard...
The Wave at Kapalua, Ocean10th Hole Golf Course Views NEW Full Remodel late 2022
3 years in the making completely remodeled top to bottom, new everything as of Aug 2022, "The Wave At Kapalua" is your perfect Maui vacation condo with an ocean view! Designed with an elegant tropical whimsey, bright, and colorful, with accents and attention to detail...
Hawaiian condo next to the Kaanapali Golf Course
Ka'anapali Plantation 54 is a 2-bedroom, 2-bathroom unit that offers split A/C in every bedroom and a main living area spanning out to the kitchen and ocean views from this 2nd-floor unit. Unit 54 can accommodate up to 5 guests. The master bedroom features ocean views,...
Lani Paradise Oceanfront Retreat with Private Pool
Discover paradise with a private pool, surrounded by natural oceanfront scenery. Revel in the charm of this tastefully decorated 4-bedroom, two-story Villa and romantic 2-bedroom Cottage overlooking Maui's North Shore.This exclusive property offers private waterfront...
Aloha Condos, Na Hale O Keauhou, Townhome E-2, Ocean View, AC
Located in the highly desirable Na Hale Community, this beautiful well-appointed 2-bedroom, 2.5-bathroomtownhome offers spectacular ocean views and breathtaking sunsets. Bothbedrooms feature private, ensuite bathrooms. Additional in-home conveniences includea washer and...
Hapuna Beach Residence B25 at Mauna Kea Resort
Enjoy unobstructed beachfront views in this modern, luxurious two-bedroom unit decorated with Restoration Hardware furniture throughout. Overlooking the white sandy beach, the living and master bedrooms feature floor-to-ceiling sliding glass walls that open to create an...
Hapuna Beach Residence A34 at Mauna Kea Resort
This newly-constructed oceanfront masterpiece sleeps 6. It features sliding window walls that open to an unobstructed view of the ocean, a chef's kitchen with top-of-the-line appliances, and dual guest suites with luxurious baths. Additional features include a den/bonus...
This remodeled condo earned "Best in Kihei" 4 times and “#1 in Maui” Ocean View!
Aloha from MauiBreaking News! Iconic, cultural, beautiful Maui is back in business. We are proud to be welcoming guests to our award winning, legal vacation rental. This ocean view condo is remodeled & includes a kitchen with full size appliances. Our condo will be your...
Tracy's Tropical Treasures earned "Best in Kihei" four times and “#1 in Maui”
Aloha from Maui…Breaking News! Iconic, cultural, beautiful Maui is back in business. We are proud to be welcoming guests to our award winning, legal vacation rental. This corner penthouse is remodeled & includes a kitchen with full size appliances. Our condo will be...
Cozy Cottage in a quiet neighborhood.
Charming cottage converted from a detached garage. Full bathroom and full kitchen and combined living/bedroom space.Located in Kohala Estates not far from the resorts. Great space for stargazing in this quiet community.
Smoking Deal! Beautiful Renovated Unit, Partial Ocean View! Walk to beach 🤙🏽
Beautiful 1 bedroom, 1 bath condo completely renovated with A/C! You will love relaxing and enjoying this unit on your next vacation :)Come enjoy the beautiful island of Maui and stay in this private, modern, and comfortable unit. Kahana Beach is right across the street...
1BEDROOM/2BATH Downstairs Condo in Wailea Ekahi Village #46A -- Locally Owned
Retreat and relax in this comfortable, serene, light and airy, completely remodeled unit. This ground floor unit in the quiet, beachfront Wailea Ekahi Village won't ask you to carry your bags up a single step, while still providing a private and open environment....
Laid back cozy bungalow two bed air conditioning
Welcome to Hale Kai Hideaways, Bungalow D. This gently restored stand-alone vacation rental built in 1955, has two cozy bedrooms, a living room, kitchen and outdoor space and parking. Smack in the middle of Alii Drive, you can bike to town or walk across the street to...
Hale Alaula, Elegant Hawaiian Home at exclusive Sunset Drive
Hale Alaula, Princeville Welcome to Hale Alaula, a stunning high-end plantation style home located on golf course greens in Sunset Drive, Princeville. Alaula, meaning "Sunset Glow" in Hawaiian, is just that. Hale Alaula is situated in the exclusive Sunset Drive...
Spacious OCEAN FRONT 2Bd/2Ba Condo with AC - Sands Of Kahana 315
Oceanfront Sands of Kahana Resort- beautiful, remodeled 2 bedroom, 2 bathroom condoOceanfront Pool and second poolRestaurant and BBQ areasFitness CenterTennisACWalking distance to restaurants, stores and shoppingThis exquisite 1880 square foot condo is beautifully...
Hale Ohia – Private Gated Luxury Estate with Panoramic Ocean Views
Kauai's Premiere Vacation Rental - "Hale Ohia" This private and gated custom estate is like no other. Four suites with private baths lends this home to have constant ocean views. The exceptional out door living area - "Pai Pai" has 2 large drop down TV's for watching...
Pineapple House: Ocean View Home in Keauhou Estates w/ Private Hot Tub, BBQ & AC
This elegant 3-bedroom, 2-bath home in the gated Keauhou Estates blends spacious island living with serene privacy. Set on the ground level with tropical gardens, city views, and a glimpse of the Pacific, it offers a refined retreat just minutes from downtown...
Waikoloa Colony Villas 301 - Waikoloa Golf Kings Membership till April 2025!
Welcome to our brand-new vacation rental home. We have a 2 bedroom 2 bath end unit at the Waikoloa Colony Villas located in the Waikoloa Beach Resort. Come and explore our Island of Hawaii, from Mauna Kea snow-capped mountain to Hawaii Volcanoes National Park where you...
Hale Maluhia ~ Peaceful home
Experience the ultimate North Shore getaway at Hale Maluhia, a serene retreat nestled in Turtle Bay. This cozy 1-bedroom unit features a queen bed, a twin daybed, and a fully equipped kitchen. Enjoy the convenience of air conditioning, free Wi-Fi, and resort style...