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.
Charming 2-bedroom Oceanfront Condo in Kailua-Kona with AC, WiFi
Enjoy a peaceful stay at this charming oceanfront 2-bedroom condo at the Kona Bali Kai in Kailua-Kona. This tremendous property offers all the comforts you need, including AC, in unit washer & dryer, and WiFi. With 2 bathrooms and a cozy atmosphere, it's the perfect...
A/C throughout spacious clean comfortable main floor condo with lush garden view
Waikomo Stream Villas is an intimate 3.9 acre resort consisting of beautiful tropical plants, a pool, and wading pool. Waikomo Stream Villas is located near beaches, dining, shopping and golfing.Our condo has approximately 1000 square feet of living area, plus an...
Ko Olina Kai 1105F: Family-Friendly w/ Pool, Spa, Near Disney Resort
This property is offered as a monthly rental. Although full-month occupancy is not required, the monthly rate remains fixed and applies in full, regardless of the number of nights stayed, as prorated rates are not available.Discover the charm of island living at Ko...
Family Friendly Condo in Princeville with sparkling Pool-Jacuzzi and BBQ's
Reconnect with loved ones in this family-friendly place. This amazing condo, right across the street from the Makai Golf Course, has an adjoining door, one unit has a master bedroom with a king bed, and a loft with 2 full beds plus a sectional couch that is comfortable...
Nalu Bliss- Amazing 2BR Waterfront Location on Alii Dr Close to Town and Beaches
Updated 2 BR 2nd floor Condo in small 16 unit development overlooking the pacific with amazing sunset views!! We purchased the condo in June, and it was a very active VRBO with a 4.8 rating and more than 40 reviews!! We have made a number of upgrades since purchasing...
🏖️Waikoloa Golf Discount | Views of Ocean & Golf Course | vrKCV
vrKCV - Hali'i Kai 8C, Professionally Managed by Kona Coast VacationsHali'i Kai 8C – A Luxurious Ocean View RetreatWelcome to Hali'i Kai 8C, your ultimate getaway on the Big Island of Hawaii! This premium ground-floor condo offers stunning ocean views and an...
Marina Hawaii Vacations - Best Location In Waikiki! Spacious Studio, Full Kitchen!
Construction Notice 2/10/25: Spall repairs are currently underway on the ocean-side units. Please be aware that construction noise may occur between 8 AM and 5 PM. The project is expected to be completed by July 2025.This condo is located at the Ilikai Marina, on the...
Newly Remodeled Ocean View 2 BDRM Condo at the Watermark
Aloha from Waikiki! This property is a 30-day minimum rental at The Watermark. One of the most luxurious buildings in Waikiki! Located near the main Waikiki strip and in one of the most convenient areas of Oahu. It features a fully equipped kitchen ready for you to cook...
Incredible Oceanfront Corner Penthouse, 3B/3Ba, 2700 sq ft, NEW remodel!
Book with confidence- our resort is zoned Hotel/Resort! Luxury and location combined! This 2,700 square foot Direct Oceanfront 3 bedroom, 3 bath corner penthouse condo with central air-conditioning on two levels is a true Hawaiian paradise. Come and enjoy our new...
Beautiful AC Vacation Beach Property, Minutes to Best Snorkeling Beaches in Hi
WHY STAY ANYWHERE ELSE IN HILO BUT CLOSE TO BEACHES WHERE THE WEATHER AND SNORKELING IS BEST!!For guests who want the cool comfort of AC when staying in our islands our beach vacation rental offers just that! While some of our guests prefer the tropical breezes, with...
Oceanfront - Private- Family Friendly He'eia Bay-House and Cottage-
Ocean front- Nestled between Historic He`eia Bay and Keauhou Bay- Kinohi at He`eia Welcome to He`eia Bay Hale. Comfortable and bright, this house and guest cottage has 5 bedrooms and 3 bathrooms in the main house and two queen size sofa beds and bathroom in the guest...
Amaui Island Escape – New 4BR Home with Pool, Spa & Mauna Kea Beach Access
Luxury Hawaiian Retreat – Private Pool, Hot Tub & Exclusive Beach Access!Escape to paradise in this brand-new, 4-bedroom luxury home, just minutes from the world-renowned Hapuna and Mauna Kea beaches. Nestled along the stunning Hapuna Golf Course, this exquisite...
Luxury Ocean View 4 Bedroom Home
This home is set in the prestigious Kukuiula neighborhood. It is a single-story home offering a spacious floor plan. The gourmet kitchen flows seamlessly into the living area making it the perfect place for the cook in your group to serve pupus while you sip wine and...
Beautiful Island Style Home with A/C, Ocean Views and Lots of Space!
Hale 'O Malina is located in beautiful Waikoloa Village. The "Village" as it's affectionately referred to is located just up the road from world class golf courses, pristine beaches, stunning resorts, amazing restaurants and so much more!This home has vaulted ceilings...
Maui Resort Rentals: Honua Kai Hokulani 437 - Spacious 4th Floor Partial Ocean View Studio!
This spacious studio provides partial ocean views of the Pacific and Maui's neighbor island Lanai from a desirable 4th-floor vantage point nestled in the Hokulani interior courtyard.Relax and reconnect in the ample living space, recently updated with new flooring, a...
Newly Renovated Stunning Beachfront 5 Bed, 6.5 Bath Estate with Pool, Spa & AC
One of the most stunning homes and locations in Maui. The beachfront home is 'U' shaped, with a spacious lanai area which includes a pool and spa and which overlooks the beach, ocean, and the island of Lanai. Located on a private palm tree lined lane with gated entry,...
Kolea 2C offers a nice ocean view in a peaceful location within Kolea.
Enjoy an amazing ocean view from this three bedroom Kolea penthouse. Overlooking the deep blue waters of the Pacific, you are sure to enjoy whale sightings during the winter months!Just through the large wood front doors is the great room. Located here is the spacious...
Private, ocean front home with private pool, Amazing place!
Rick’s PlaceDiscover how to REALLY relax!Would you like to relax in your own peaceful pool that you share with no one, listening to your favorite tunes, while enjoying the vast expanse of the ocean right in front of you - amazing whales, spinner dolphins and colorful...
Beautifully Furnished-Great for families 3 Bed, 2 1/2 Bath Nihilani, Princeville
PLEASE MAKE AN INQUIRY BEFORE BOOKING.Aloha and welcome to Eddie’s Hula Hut! Don’t let the name fool you. Our spacious condo is fully furnished for your vacationing pleasure. You will quickly get yourself into vacation mode in our newly decorated condo which has a...
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...
Hale Mauka Volcano Village Hawaii Volcanoes National Park
Volcano Hale Mauka welcomes you to a lovely private cottage nestled in the middle of the rainforest! Our house is very clean and well appointed. Hale Mauka offers you a place to come home and relax after a long day out exploring and playing. Rates are for up to 4...
Until you experience it you don't know it exist... Exceeded our expectations
Thank you for showing interest in Kohala Lodge. This Beautiful 2400 square ft craftsman-style Paniolo (cowboy) retreat is your's for you and your guest only. The retreat sets on 3.5 acres located at the Northwest coast of the Big Island above Historic town of Hawi. When...
Rejuvenate in comfortable luxury
Kulalani 2202 is the perfect home base for your Big Island vacation. The model is floorplan A2 which is the largest townhome floorplan in the Kulalani community. With its large master suite on the ground floor and two guest bedrooms upstairs, this spacious abode...
Wailea Ekolu 1207 2 Bedroom 2 Bath Condo
Relax at our quiet 2 bedroom /2 bath condo with stunning views overlooking the Wailea Blue golf course all the way to the ocean. Guests can enjoy amenities like a washing machine, AC, and WiFi during their stay. We hope you'll enjoy your stay at our condo.
Spacious Oceanfront Hideaway – Ground-Level Boho Zen Paradise with Stunning Lana
The Space:Welcome to your dream getaway at our spacious 1 Bedroom / 2 Bathroom, (sleeps 4) oceanfront ground level condo located at the prime location in the heart of West Maui!Wake up to breathtaking panoramic views of the Pacific where whales (seasonally), sea turtles...
Boutique Oceanfront Vistas
Summary:Elegantly remodeled oceanfront studio with fantastic ocean views. Located in the sunny and vibrant beach town of Kihei. Beach chairs, umbrellas, luxury beach towels and a cooler are all provided to enjoy your day at the beach! We strive to achieve a welcoming...
Luxury Condo in Wailea with sweeping views
2 large master ensuite bedrooms with Cal King beds. Sweeping views of Kaho'olawe, Molokini, and Lanai islands and spectacular sunsets. Beaches, restaurants, and Shops of Wailea all within walking distance. Fully equipped kitchen, with plenty of dining wear and cooking...
Only Steps to Ulua Beach and the main Wailea Ekahi Pool/Pavilion -1 Bd+2Ba
New A/C system, new bed and mattress, new furniture, new electronics. Professional Photos Pending - Wailea Rentals presents: Wailea Ekahi Village 8E - Ekahi means #1 in Hawaiian and that is exactly what Ekahi Village is - 1 of Wailea's top luxury beachfront condominium...
Spectacular Kapalua Golf Villas Unit!
Enjoy the luxury of this spectacular Kapalua Golf Villas unit located in the world renowned Kapalua Resort. This two-bedroom, two-bath unit is the perfect getaway for all vacationers. The property is located near stunning beaches, hiking, golf, surfing, and many more...
Gorgeous Oceanfront Estate, Steps From Beach w/AC & Puako Bay Views: 10D
Welcome to 3BD Estate Home at Puako Bay (10D), a luxurious oceanfront sanctuary on Hawai‘i Island’s sun-drenched Kohala Coast. Set along the sands of Puako Bay, this 2,520-square-foot residence captures breathtaking panoramic views of the Pacific and offers the...
Ocean Views, Great Sunsets, large private lanai
Welcome to your Kona home-away-from-home, a beautiful and inviting, two-story property featuring a spacious, 950+ sq. ft. two-bedroom, one-bath apartment that takes full advantage of its peaceful, elevated setting and stunning sunsets. The apartment occupies the entire...
Poipu Kai 3 Bedroom with Pool and Spa steps to Shipwreck Beach
Brand New Listing Located in the upscale Poipu Kai neighborhood this new home embodies pure enjoyment and relaxation. The layout of this three bedroom single level home offers all the room and privacy for a trip of a lifetime. The large pool and spa will keep you...
DISCOUNTED RATES! 202 Quaint 2nd floor with private lanai
You can enjoy your coffee on the private lanai while watching turtles (honu) and whales, during the winter season. Sunsets are amazing every single day. Every night at sunset, Kulakane tradition is to blow the conch shells at sunset. You will find a conch shell in your...
Hale Ohana: Kailua Retreat w/hot tub, Tropical Pool, Walk to Beach
This property is offered as a monthly rental. Although full-month occupancy is not required, the monthly rate remains fixed and applies in full, regardless of the number of nights stayed, as prorated rates are not available.Hale Ohana meaning Family House is just that!...
Wailea Grand Champions 183 - 2 Bedroom Garden View Condo
Welcome to Wailea Grand Champions 183, a luxurious vacation rental that perfectly blends comfort and style in the heart of Maui\'s paradise. This stunning two-bedroom, two-bathroom retreat offers an exceptional experience for discerning travelers seeking a memorable...
WOW - DIRECT OCEANFRONT - AC - SANDS OF KAHANA - SLEEPS 4 - n2 BEDROOM - 2 BATH
***WOW - DIRECT OCEANFRONT - AC***SANDS OF KAHANA Hotel Zoned - Short-Term Rental/Transient Vacation Rental allowedThe Aloha Spirit invites you to come and experience firsthand the many activities and beautiful sunsets that await you in this privately-owned condo at the...
New opening Apr22-Apr28,2025. Spectacular 6Th floor view.Prime location,unit662.
Condo Amenities:Right on the beach studio condo with tennis courts, large pool,jacuzzi,and sauna with plenty of lounge chairs. Built-in barbecues with tables located on the lawn. An unforgettable ocean and sunset view, indoor nautilus gym,Restrooms in the basement in...
CheCa Hale: Gorgeous Top Floor Corner Unit, With AC
Hopu i ka la ("catch the sun") at CheCa Hale! This airy, air conditioned, two-bedroom, two-bathroom corner penthouse is the perfect choice for family and friends traveling together. The home was beautifully and fully updated in 2022. Located in the beautiful Keauhou...
Not Like the Rest- Immaculate Remodeled Luxury Golf Villa-See Our Photos
Book this luxury golf villa on the Big Island for your next Hawaii vacation! Celebrate in the relaxed luxury provided at this recently remodeled Tommy Bahama designer-decorated townhome at the Golf Villas at the world-renowned Mauna Lani Resort on the Kohala Coast...
Makaha-465 Farrington: Spacious 4BR Oceanfront Haven with Modern Amenities
Set your sights on paradise at Makaha – 465 Farrington Hwy by Gather, a timeless beachfront retreat on Oahu’s serene west shore. Once a cherished family getaway and now lovingly reimagined for modern comfort, this four-bedroom, three-and-a-half-bath home offers a...
Charming Beach Cottage by Mama's Beach
Grom's Hideaway is a charming cottage nestled in the heart of Kuau Point, the last little neighborhood 1 mile outside Paia(a 5 min drive), as you head out on Hana Highway. Grom's has 3 bedrooms (king, queen and two twins) and 1 Bath with an indoor and a Very Private...
Kona Reef F2 – Charming Oceanfront Condo for 4!
Summary:The mesmerizing gem of Kailua-Kona is something that truly has to be seen to be believed, offering an unforgettable tropical escape for visitors from around the globe.The Space:Margo and Frank first came to the big island some 10 years ago. They came to Kona...
❤️PiH❤️ Island View ★ Ocean & Mountain Views ★ Hilton Pool Passes
Brought to you by Paradise in Hawaii Luxury HomesWelcome to Island View at KaMilo, a wonderful 4 bedroom home that sleep 10.We pride ourselves on providing some of the most sought after homes on the Kohala Coast and are thrilled to add Island View to our...
Perfect location in Kihei! 5 minutes to the beach!
If you want to be close to it all - best beaches, best snorkeling, only surf spot in Kihei, SUP, kayaking, snorkel tours, dinner cruises, shopping, restaurants, nightlife - our recently updated, owner-managed (no dealing with unresponsive property managers) condo is the...
Oceanfront: Amazing Location, Steps to the Beach! Split AC, Pool, King Bed
Aloha from Sea Breeze at Menehune Shores! This remodeled 2 bedroom and 2 bath oceanfront condo in South Kihei’s Hotel Zone offers breathtaking ocean views from the 4th floor. Enjoy direct beach access, a pool, and a kid-friendly lagoon perfect for swimming. The condo...
Home away from home in 1 bedroom condo with A/C and pools in central Kapaʻa
Discover this 1-bedroom gem in Kapaʻa with a fantastic location! Less than 5 min walk to the beach, shops, restaurants, weekly farmer's markets and Kapa'a's walking/bike path. This charming and clean condo is fully furnished on the 2nd floor with staircase access only....
Family-Eco Friendly House🌺Walk to beach,dining,park,shops,hot tub,AC
Beautifully remodeled house with ultra-quiet split AC systems in every room, fun for everyone with the new Infinity game table, whole house water filtration system, ceiling fans, resort-style landscaping and lighting.Within a 10 to 15-minute walk of 40 restaurants,...
Napili Point A10 - A Piece of Paradise - Swim With Turtles Just Steps Away
Do you want to enjoy paradise? Make memories as beautiful as the sunsets? Enjoy beautiful sunsets, walking on the beach, smelling tropical flowers, looking at breathtaking scenery, being one with nature? If so, you will want to book this fully equipped one bedroom Point...
Cottage on a 3 acre estate, spa, fireplace, cozy, park like setting, fruit trees
Hale O' Makani, is located in upper Paauilo cool temperatures for a comfortable nights sleep, lots of mature trees, including fruit trees, vegetable garden,surround this property, very cozy cedar cottage ,with 1 bedroom, queen size bed, full kitchen, bathroom with tub...
Kaanapali Alii | 433
Welcome to Kaanapali Alii 433, your perfect luxury vacation rental for a memorable stay on the stunning island of Maui. This spacious one-bedroom plus den garden view condo, covering an impressive 1,553 square feet, offers a comfortable and relaxing retreat for families...