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.
Ground-floor, oceanfront condo with amazing views & pool - walk to dining
Kapa'a Sands 14Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'This boutique establishment is right on the ocean, enveloped in lush tropical gardens with everything you need for your...
Beachfront Bliss Awaits! Sugar Beach #125 - Luxury and Comfort at Your Doorstep
SUGAR BEACH RESORT, #125Welcome to Sugar Beach Resort #125, a ground-floor beachfront condo offering the rare convenience of stepping directly from your lanai onto Maui’s golden shoreline. Nestled in North Kihei, this retreat blends comfort with ease of access, making...
Maui Resort Rentals: Honua Kai Hokulani 145 - Spacious Ground Floor Interior 2BR, Steps to Pools/Beach/BBQs!!
Enjoy one of the most convenient ground floor locations at Honua Kai in the interior courtyard of the Hokulani Tower. Hokulani 145 offers a spacious 1100 square feet of living space and convenient interior ground floor access to the pools, beach, and BBQs.The oversized,...
Oceanfront and updated, top floor, perfect for honeymoon
Very private top floor ocean front location. Sealodge E10 is the perfect choice for a honeymoon. All of the north shore's great beaches and attractions are conveniently close, and there's a beach path onsite, but you'll be perfectly happy to stay in too, and enjoy the...
Faces Kamaole Beach Park 3, Ground Floor, Large Lanai, ocean view
Unit 1-103 is on the ground floor of the highly desirable Building 1 at Kamaole Sands Resort. This condo complex faces the beautiful Kamaole Beach Park 3 which is across the street. This beach is well known for boogie boarding, snorkeling, and watching the sunset. Beach...
2/2 BEACH FRONT RESORT w/AC, Poipu Beach, Kiahuna Gardenview -End Unit, Pool/Gym
This condo has air conditioning upstairs and downstairs - only a few 2-bedroom units here have AC. This is also the only condo resort in Poipu on a sandy beach! Other condos are on a rocky shoreline or a long walk or drive to the beach. This beautiful and spacious...
Lush Garden Charmer - Breathtaking Sunsets
You will feel at home in this cozy but spacious one bedroom, one bath, ground floor condo. It is furnished and equipped with all the amenities of home. It has a fully equipped kitchen with microwave, full size stove and refrigerator, drip coffee maker, keurig, rice...
Maui Resort Rentals: Whaler 1002 – Remodeled 10th Floor Oceanfront 2BR w/ Stunning Ocean Views!
Boasting a stunning 10th-floor oceanfront corner location, Suite 1002 delivers panoramic oceanfront vistas that are among the best in the entire state of Hawaii.Take in the incredible views of the blue Pacific and neighboring islands of Lanai and Molokai, or experience...
OCEANFRONT RESORT- $299 through May 15! Kihei Sands Beachfront Condo-B10
Winter has arrived - and so have our exclusive new seasonal rates from November - March 2026. Leave the cold behind & step into the warm embrace of on Maui's Sugar Beach sun-kissed shores! Welcome to Condo B10 in sunny South Maui! This second-story (no elevator) condo...
We are OPEN for our guests Penthouse 938 W/ Panoramic Oceanview Splendor KShores
Welcome to Ka'anapali Shores #938The best vistas are from the top, this is a 9th floor penthouse with panoramic top floor ocean views. Enjoy the splendor of a remodeled penthouse with sweeping ocean views. Located atop fabulous Kaanapali Shores, a AAA, triple diamond...
Fabulous condo with views at Pali Ke Kua, shared hot tub & pool, WiFi, balcony
Pali Ke Kua 113Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'This is what you think of when you think of Kauai: beautiful sunsets over the ocean, twinkling stars in the sky, waves...
ATTRACTIVE & Updated 1 Bed 1 Bath in Kihei Maui!
This adorable and tranquil unit with an open and airy floor-plan, tile and laminate flooring throughout and tasteful Hawaiian décor. Our updated condo is located near the pool and is spacious & tranquil. You will love the fresh, open and airy floor-plan of this unit,...
Perfect unit for a romantic getaway! Kapalua Bay Villa #12B4
Kapalua Bay Villa 12B4 is a serene one-bedroom, one-bathroom oceanview retreat nestled in one of Maui's most prestigious coastal communities. This elegant villa offers a seamless blend of comfort and luxury, featuring central air conditioning, a gourmet kitchen with...
Oceanfront Condo at the Mana Kai Maui, Luxurious, Designer Remodeled
Hawaii Tax ID: TA-127-536-5376-01TMK: 390040230081Mana Kai 711 is situated on one of the most prestigious beaches in all of Hawaii and spares no expense when it comes to luxury and unobstructed ocean views. Mana Kai is situated on the famous Keawakapu beach of...
Oceanfront Penthouse with Loft!
Everything you'd ever want in a tropical getaway! With the ocean just feet from your private lanai, your family will be close to everything Kona has to offer when you stay at this centrally-located place. Enjoy the immaculate grounds of the Kona Makai with two tennis...
Stunning waterfront condo with WiFi, shared pool/hot tub, & amazing ocean views
Pali Ke Kua 224Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Enjoy the awe-inspiring views of the Pacific Ocean and the north end of Hanalei Bay with Mt. Makana in the background....
Stunning Private North Shore Oceanfront Retreat!
Prime oceanfront location in the illustrious Pali Ke Kua condominiums. This modern condo features cascading views of Hanalei Bay and beyond! Situated in the Princeville community, this retreat is located near all the north shore has to offer. Enjoy the pool, take a...
Remodeled Ocean View Condo with Beach Access, Resort Pool & Hot Tub
Kahana Villa E610Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Stay in this recently-remodeled, family-friendly, air-conditioned condo with ocean views and enjoy shared on-site...
Halii Kai 15D True Ocean Front. Watch Dolphins and Whales (in season) from your Very Private Lanai
This highly desirable upper floor, corner unit is in one of only three buildings at top-rated Hali'i Kai resort that are directly on the oceanfront. This top level corner unit is located near the Ke Kailani grotto, avoiding some of the noise and activity from the...
Perfect Maui Beach Home: Penthouse, Great Views, From $195
This is our Maui home, a 4th floor penthouse. We recently put in new furniture, carpet and paint. This condo has been a part of our family since it was new in 1974 and we have carefully remodeled it for maximum comfort and enjoyment. There is a new flat screen (4K, HDR)...
Stunning Ocean and Mountain View | Kauai North Shore
Hanalei Bay Resort, #3105Spacious studio unit with stunning ocean and mountain views of Kauai's north shore. This is a fully air-conditioned, ground floor condo that overlooks Hanalei Bay, Bali Hai, and is located at the beautiful Hanalei Bay Resort. The spaceStudio...
Explore Kauai & Relax in Luxury - Pool - Grills
Adventure & Luxury Awaits You - Explore the Island of Kauai: Swim, Snorkel, Hike, Surf or Read Under a Shade Tree. Then return to this High-End Luxury Suite with a Resort Pool, Jacuzzi and BBQ grills just steps away. This well appointed suite is Ideal for Special...
Classic Kailua Beach House – Oceanfront Bliss in Windward Oahu
This property is professionally managed by Private Homes Hawaii, LLC and is licensed as a short term vacation rental, 1990/NUC-1780 and is compliant with Hawaii State Legislation (HB2078) for vacation rental accommodations, TA-179-906-2528-01. TMK.Welcome to "Kailua...
Beautiful - Palms at Wailea 1802
Located in the Kihei/Wailea area, in the world-famous Wailea Resort community, The Palms at Wailea complex boasts a beautiful pool, hot tub and is conveniently located close to the Shops of Wailea, luxury hotels, stylish boutiques, great restaurants, tennis, the Wailea...
Beautiful penthouse suite with stunning ocean view, pool, hot tub & beach access
Sugar Beach Resort PH05Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Treat yourself to the unmatched beauty of Maalaea Bay from Sugar Beach Penthouse 5. You'll be situated mere...
COZY CONDO, JUST STEPS FROM THE OCEAN, LOW DENSITY PROPERTY!
MAUI SANDS SEASIDE IS A SMALL COMPLEX WITH LESS DENSITY FOR THOSE WHO WISH TO PRACTICE SOCIAL DISTANCING OR JUST PREFER TO BE AWAY FROM LARGE CROWDS IN GENERAL. THIS IS A GREAT LOCATION FOR A FAMILY VACATION OR FOR A COUPLE'S RETREAT. THIS IS THE PERFECT LOCATION TO...
❤️PiH❤️ Seashell Villa ★ Bikes ★Free Hilton Resort Passes ★Free Private Beach Club
Brought to you by Paradise in Hawaii Luxury Homes.Welcome to the newest home in our Hawaiian Luxury Collection. Seashell Villa is a wonderful almost new exquisite 3 bedroom home in the gated Kulalani community with high end finishes with pool and recreation center...
Oceanfront Condo with 180-degree penthouse views
Sealodge G9Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Perched atop the oceanfront cliffs in the community of Princeville, this unit offers unbelievable views from every room....
Kona Condo White Sands Village Beach View / Ocean View #215
Stay 70 yards from famous Magic Sands Beach (White Sands Beach). Its Time to come on over and Holo Holo (vacation) with us here in beautiful, sunny, HAWAII. Your unit is located on the Big Island's famous Alii Drive directly a cross the street from Magic Sands Beach...
Modern Ocean View Studio - Waikiki Paradise!
Thoughtfully appointed studio with modern decor. Fully renovated in February 2022! Includes FREE high speed Wi-Fi, cable TV, and various TV apps for streaming services.Check in and out at your convenience with a lock box. Check in after 3pm and check out before 11am....
Poipu Koloa - 2 br unit Ocean/Garden view in Kauai
We can book Ocean Front/OV/Garden view unit if they are available.Price from the system is for Garden View unit. If you like OV, please request it.This is timeshare resort, per policy, unit number floating. Don't know exact unit be assigned until check in, but the view...
Palm-lined condo with easy beach access, pools, hot tubs, & tennis courts
Tropical Oasis at Poipu Kai 514Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Say aloha to your next favorite vacation when you book a stay at this newly remodeled first-floor Poipu...
Views! Beaches and Shopping Right Next Door! A308
Discover your perfect Maui escape at Kihei Alii Kai A308, a stunning 2-bedroom, 2-bathroom oceanview condo that seamlessly blends comfort and tropical luxury. Recently refreshed with fresh paint, new living room furnishings and crisp white linens, this spacious retreat...
Daydream Believer, House, 4 bed, 3 bath, sleeps 13
Summary:Spacious 4-bedroom, 3-bath home sleeping up to 13, just a short walk to Shipwreck Beach, Poipu Beach Park, and the community pool. Enjoy two living rooms, a game/lounge area, mountain views, a fully equipped kitchen, and plenty of space for the whole ohana....
Private Waterfront House AC & Fast Wi-Fi 30 Day
This house is all about being right on the water. A seawall provides protection from waves at high tide. A North Shore Beach House with the comforts of a nice home ideal for long term stays. Local pickle ball played right down the street. 30 Day Minimum ContractIncluded...
Spectacular Views 1 BR / 1 BA condo in Poipu
A lovely condo overlooking the blue Pacific. Fully equipped and furnished by the owners with much attention to detail. The fully equipped kitchen is both lovely and very convenient for preparing meals and snacks. You will want to visit the local Sunshine Markets for...
TCNC # 1161 All Cedar Home - Breathtaking Hanalei Bay and Mountain Views
TVNC # 1161 Waterfall laced mountains and Hanalei Bay views through a tropical prism. These will be your first impressions and lasting memories of this welcoming home. The Hanalei Vista House is an all cedar home built 15 feet off the ground to enhance the spectacular...
Naia Hale, Spacious A/C home for a relaxing visit
Spacious A/C two-story home, perfect for families and friends to spend quality time together. Have a wonderful family reunion here, come during the holidays for a relaxing visit with loved ones, or celebrate a special occasion at this elegant home. You will create...
Pacific Ocean views & newly renovated kitchen
For the same price as a typical hotel room, you could be staying in a spacious, beautifully renovated home that accommodates up to 6 guests, with sweeping ocean views and a large kitchen that’s perfect for family meals and group gatherings.This bright and airy...
Weneki's Island Paradise; Oceanfront complex, Updated, Wi-Fi, Unit 103
Weneki's Island Paradise is an oceanfront complex, ground floor condo with a garden/pool view and just steps from access to the ocean. Located in Honokowai, just 5 minutes from Lahaina. It is a 1 bedroom without A/C, fully furnished with a Cal-King bed, 1 bath with...
Kailua Kona HI Deluxe Condo Discount - booked for a week - Flex Cancellation
Beautiful authentic Hawaiian Pleasure is truly yours when you stay at Wyndham Kona Hawaiian Resort anytime! Every detail is designed to re-create the charming island ambiance found back in the ’30s, while still assuring you all the comfortable amenities and activities...
🏖️Spacious Property! | Tranquil Location | Concierge Included | vrKCV
vrKCV - Mauna Lani Islands M3, Professionally Managed by Kona Coast VacationsWelcome to Mauna Lani Islands M3—your home away from home on Hawaii's stunning Kohala Coast.Located within the prestigious Mauna Lani Resort and Golf Course, this beautifully appointed townhome...
Pali Ke Kua #110 Paradise! Panoramic Ocean and Bali Hai Views!
This beautiful ground floor condo has undergone a COMPLETE REMODEL! The beautiful remodel features Quartzite counters. All new cabinets, Kitchen Aid stainless steel oven and dishwasher, along with a Café refrigerator. Beautiful new tile flooring, all new furniture, and...
Tropical Tree Guest House near Pahoa, Hawaii
Welcome! The Tropical Tree Guest House has a clean rustic lodge feel and is easy to settle into. Enjoy the full vintage kitchen and bathhouse. One mile to Kehena Black Sands Beach, 8 miles from the 2018 Leilani lava flow coastal trail head to Po'hoiki Surf Beach and 4...
Breathtaking Anini home with guesthouse & steps away from beach
Ka Hale Olu at Anini Beach TVNC#4218Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Find a true escape in the luxe comfort of this exclusive property steps away from Anini Beach and...
Hibiscus Hale in the Heart of Downtown Kona
1 Bedroom, 1 Bath, kitchen, bottom level town house. We have a BBQ area and a laundry room for you as well. This is a vacation you will never forget! The house is located just minutes walking distance to all restaurants, sports bars, shops and beautiful beaches in the...
"Island Time" at Plantation Hale D4* New to our Management**Special Rate**
"Island Time", a freshly updated, ground-level condo at Plantation Hale, offering comfort, style, and space just steps from Kauai's Coconut Coastline. With two full size beds in the bedroom and a full size sofa sleeper, this unit is perfect for families or friend groups...
Car Available! 180 degree Ocean Front Unobstructed View. Sleeps 8
OCEAN VIEWS! OCEAN frontage FAMILY GETAWAY!4 bedroom/4 full baths SLEEPS 8Live the true Hawaiian experience of peace, beauty and relaxation. Sleep with the gentle sound of the ocean and cool breeze. This ocean bluff condo offers it all! Why go to Kauai and not stay on...
Beautiful 1BR, Steps to Waikiki Beach + Parking
Aloha from Midway Vacations! Our team of local hospitality experts is dedicated to turning your Hawaiian getaway into a reality. When you stay at one of our properties, you can count on a professionally cleaned and meticulously maintained experience. We're even...
150-3 Superior Oceanfront Gold Coast Location.
This beautifully appointed 3-bedroom, 2-bath oceanfront unit on Puamana’s “Gold Coast” remains a peaceful retreat amidst the recovery efforts following the Lahaina fire. Located in a tropical oasis at the south end of Lahaina, this luxurious townhome offers the best of...