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.
Huge Home with Pool, Jacuzzi & Water Slide! Sleeps 18!
Affectionately named “The Pool House” by our 4 little ones, this house is above and beyond its typical name sake. This sprawling 3,000 sq.ft. home boasts 5 bedrooms and 5.5 bathrooms, with room to sleep at least 18 comfortably. A sleek modern kitchen, outdoor grill, 2...
Luxe Golf Estate w/ Hilton Pool passes - Sleeps 10
Luxury Meets Paradise: Nohea Hale in Waikoloa Beach Resort – Top 5% Airbnb Guest Favorite!Welcome to Nohea Hale, a luxury 4-bedroom, 4-bathroom Five-Star estate located in the prestigious Ainamalu community at Waikoloa Beach Resort. Ranked in the top 5% of Airbnb guest...
Na Hale Keauhou M5: Your Coastal Villa Awaits
Welcome to the Seaswept Mermaid Villa, a stunning ocean-view condo located in the beautiful Keauhou area of Kailua Kona. This inviting two-bedroom, two-bathroom retreat is perfect for families or groups of up to six guests, offering a serene ambiance that captures the...
Elegant Pili Mai 14-J: Spacious 3BR Villa with Pools, A/C, and Beach Proximity
The Resort:Pili Mai was built in 2019 and features plantation-style design, cobblestone drives, tropical gardens, a large swimming pool, a children's pool, spa, and an air-conditioned fitness room. It is nestled between Kiahuna Golf Club and the beautiful Poipu beaches:...
Discovery Bay-Resolution Ocean View Condo
Oceanview 1 Bedroom, 1 Bathroom Sleeps Up to 4 Condo DescriptionLooking to travel to the island for business or extended vacation? This large newly renovated 1 bedroom unit has everything you need that will make you feel at home while reminding you that you are on a...
Maui Resort Rentals: The Whaler 212 - Gorgeous Remodel, 1BR/2BA w/ Ocean and West Maui Mountain Views!
Not previously available for vacation rental, this gorgeously remodeled 1B/2BA suite at the Whaler boasts a desirable vantage point with beautiful views of the Pacific Ocean and Maui's neighbor island, Molokai, as well as views of the West Maui Mountains.Your party will...
Hawaii Life Rentals Presents Puu Poa 307
***DISCLOSURE: Puu Poa 307 is listed for sale. Guest may be asked to accommodate showings of the property with 48 hours notice.Puu Poa 307 combines the serenity of verdant mountain and deep blue ocean views with a newly renovated and thoughtfully designed condominium....
KBM Resorts | FREE CAR | Kapalua Bay Villa | Oceanfront | 1-Bedroom Condo, Gorgeously Remodeled! KBV-26B1
** 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...
*Nani Kai Hale 507* Beachfront Maui Condo!
New Remodeled bathrooms! With breathtaking ocean views right on the beach, this 5th floor beautifully decorated unit offers full beachfront access. The master bedroom features a California king bed with a en suite tiled walk-in shower. There is also a sofa sleeper in...
Oceanfront Luxury at Honua Kai Konea 250: Stunning Views & Gourmet Amenities!
This property is hotel zoned, and not being affected by the recent proposed legislation.Honua Kai Konea 250 offers luxury at its finest! As you enter you will be in-awe of the breathtaking direct ocean views from this luxurious villa located at one of the most exclusive...
Direct oceanfront penthouse. Modern renovation. Exceptional views!
Expansive oceanfront views in paradise!This property is the exact definition of direct oceanfront living and has been newly renovated! You cannot get closer to the water unless you are on a boat. Whale watch from your expansive private lanai and allow the lapping waves...
Waikoloa Resort gem with pool, hot tub & balcony - 1 mile to beach
Waikoloa Fairway Villas B32Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Experience the best of Hawaii from this third-floor 2BR/2BA condo at the Waikoloa Beach Resort. Soak up the...
Posh, beachfront gingerbread home with 3 lanais- walk to parks, dining, tennis
Oceanfront Kalakaua Surf & SunsetsOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Located directly on spectacular Tonggs Beach, this posh 3BR/2.5BA home looks fresh from the pages of...
Ground-floor, golf-view condo near A-Bay beach & shops with infinity pool & spa
Waikoloa Fairway Villas O3Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Nestled in the exclusive enclave of Fairway Villas on the Big Island's Kohala Coast, this...
GORGEOUS OCEAN VIEW and Sunsets! Full Kitchen, Washer/Dryer, Wi-Fi, Sleeps 4.
Waikiki Shore #1416 – 2161 Kalia Rd.This cozy 1-bed/1-bath suite boasts breathtaking 14th-floor views of the Pacific Ocean and the greenery of Ft. DeRussy Beach Park next door. Bask in the cool trade wind breezes as you enjoy al fresco dining on your private beach-view...
Honua Kai- Konea 608 Beautiful Ocean View, Large 2 bedroom on 6th floor
Located on Maui's renowned Kaanapali North Beach, enjoy Honua Kai Resort & Spa’s 5-star amenities with this luxury two-bedroom, one-bath villa.This spacious suite, which sleeps 6, is ideal for families. Located on the 6th floor of the Konea Tower, the 950 sq ft interior...
Ocean Views! Mauna Kea Resort. Beach Gear Include. Kumulani J3
This vacation rental is professionally managed by ResorticaHawaiiKumulani J3Bedding Configuration:Master Bedroom: King BedGuest Bedroom: Queen BedGuest Bedroom: Two Twin BedsPLEASE NOTE: The Mauna Kea Hotel will be undergoing renovations starting April 15, 2024. The...
Hale Hapu’u. A unique Hawaiian experience.
E Komo Mai (welcome) to Hale Hapu’u! Our little Hawaiian hut is perfect for couples seeking an authentic Big Island experience. The Hale is adorned with hand carved art from local artists, an outdoor bath set in the midst of a tropical garden of ferns, palms & orchids,...
Island Paradise Resort Villa
This newly renovated luxurious Villa is nestled in the quiet neighborhood of Ko Olina Kai. This Villa has 3 bedrooms and can sleep up to six guests. Choose to spend your days on the Ko Olina Championship golf course or at one of the 4 lagoons located within the...
KBM Resorts | FREE CAR | Honua Kai Konea | Ocean view | 2-Bedroom Condo, Recently Remodeled! HKK-309
** 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...
Traditional Hawaiian House - Walk to Tunnels Beach
TVNCU #1146 - A gated entrance leads you through a 6 foot lava rock wall toward the rear, ground level peaceful house. Privately tucked away, on the Mauka (mountain) side of the road, behind a front house (where the housekeepers live), the rental house sits. Capture...
The Reef House in Puako: 2 BR Oceanfront Home and Cottage
Your oceanfront authentic Hawaii vacation destination awaits you! The Reef House is a perfect place to get away from it all. With breathtaking views, a paradise of snorkeling at your back door and a lush tropical yard to relax in and soak it all in. Ideally located,...
Waipouli Beach Resort Exquisite Crown Jewel!
Waipouli Beach Resort Exquisite Crown Jewel! Newest Listing! Central ACThe Ultimate Vacation Experience staying in this Exquisite Penthouse Premier Ocean View Extra Large* Luxury Condo, the Best of the Best - centrally located for THE premier view of the ocean at #1...
Waipouli Beach Resort & Spa Ocean & Pool Ground Floor in H Building! Sleeps 8
Waipouli Beach Resort H104 2 Bdm, 3 Bath – Beautiful Oceanfront and Pool View! King, 2 Double Beds & Queen Sofa SleeperOceanfront! This is one of the most spectacular locations at Waipouli Beach Resort! This beautiful ground-level unit H-104 has spectacular views of the...
Lush garden and partial ocean view
Papakea C203 is a 1-bedroom, 1-bathroom 2nd-floor condo with a window air conditioner that can accommodate up to 4 guests. Step inside the bedroom, where you will find a comfortable California king-size bed and a TV. The well-appointed kitchen is the perfect place to...
"Peggy's Place" - Premier Beachfront Condo for Families -- Direct Beach Access
Just bring your swimsuit and Aloha spirit to Peggy's Place, a recently remodeled beachfront condo on Maui's best family beach. Step right onto the sand and enjoy stunning oceanview sunsets, soak up the sun with the included beach gear, or fall asleep to the sound of...
Maui Sunset B102 - Aloha Tai 2, Beachfront Resort Condo, Ground floor, 1B/2BA, S
Summary:Condo in Beautiful Oceanfront Resort - ground floor tastefully-updated with all new furniture (April 2022) 1-Bedroom 2-bath with King Bed, Queen Sleeper & Twin Murphy bed in LR. Family Friendly, sleeps up to 5, Full Kitchen, AC, Washer/Dryer in-suite, Free WIFI...
KBM Resorts | FREE CAR | Kaanapali Shores | Ocean view | 2-Bedroom Condo with Stunning views & Great for Families! KS-260
** 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...
North Shore Garden Hideaway Apartment, No Steps
This is a newly renovated 2 bedroom apartment on a large gated lot in a very secluded neighborhood on the North Shore. The property is located on a hillside above the ocean, (it is not beach front). It is a 3 minute drive from the property to the famous world class...
Gorgeous Beach Front Home with Amazing Sunsets
30 Day minimum @ $7800.00 monthly. Wake up each morning to the soothing sounds of the waves and go to sleep after watching a memorable sunset , relax and enjoy the breathtaking sunsets on the beautiful beaches of Makaha. Step right outside to the beach from the home,...
Vintage Kahuna Waikoloa Beach Villas D1
Welcome to our Big Island Kahuna with a Touch of Nostalgia condo in Waikoloa! We are excited to have you as our guests. This beautifully appointed 3-bedroom, 3-bathroom townhome at Waikoloa Beach Villas offers both privacy and convenience. You'll love its close...
Stay & Save Plenty this April & May! ~ Spacious, Comfortable & Clean ~ Platinum Maui Vacations
Aloha! Welcome to another exclusive member of the Platinum Maui Vacation Ohana! All villas in our program are given Hawaiian names. This Kapalua Golf Villa is named Hale O Ohana, in Hawaiian translates to: "Home of Family".We include, extras like:~ Secured wifi /...
Exceptional 1 -bedroom condo unit 2323 in the heart of Kihei
This recently remodeled, bright one bedroom condo is appointed with wood flooring in the living room, bedroom and kitchen with tile in the bathroom and hallway, keeping the space airy and cool. LG-HIMacs counter tops in living room and bathroom provide a clean and...
SPECIAL RATE Unique Honua Kai REMODEL 2BD 2BA Private Oversized Corner XL Lanai
🌴 West Maui is Open – and Honua Kai is Resort-Zoned. 🌴Book with confidence knowing you’re safe from the recent legislation impacting other short-term rentals.🌿 Spacious & Ultra-Private Corner Retreat – with Waterfall & Koi Pond Views 🌿Welcome to Konea 218 at Honua Kai...
Jungle Home AC NearHot Ponds Fissure 8 Hot tub
Right off 130 surrounded by lush jungle. We are ready to help you have the best adventure this side of Hawaii! 7 person hot tub & lots of cute feral jungle kitties on site. 3BDR/2BA FULL Access. Laundry Rm is SHARED w/ host.Cable High Speed Internet, snacks, avocados on...
🏖️Upgraded 2BD Plus Loft | Amazing Golf & Ocean Views | AC | vrKCV
vrKCV - Country Club Villas 341, Professionally Managed by Kona Coast VacationsWelcome to Country Club Villas #341 – Your Dream Vacation Awaits!Aloha! Step into paradise and experience breathtaking views from Country Club Villas Unit #341. Perched on the third floor,...
Jungle view bedroom with private entrance,outdoor private Bali style bathroom
Escape after a long day of exploring our beautiful island to your own private bedroom with a private entrance. You will enjoy a jungle setting with the peaceful sounds of coqui frogs. Step outside to a Bali style open air bathroom that is just a few steps away from your...
Escape to your private oasis
Private island retreat with a garden view in an upscale Hilo neighborhood. Close to downtown, delicious restraunts, and fun farmers markets. This unit is a completely separate room that has a private entrance and private bathroom. Plus a covered parking spot to help you...
Escape to your private oasis perched on a cliff with a jungle view
Private island retreat with an awesome jungle view. Situated in an upscale Hilo neighborhood. Close to downtown, delicious restraunts, and a fun farmers market. This unit is a completely separate guest room that has a private entrance and private bathroom. Plus a...
Kona Ocean View Home - Downtown, Fruit Trees, Sunset views
Beautiful 2bedroom / 2bath home overlooking Kailua Bay in the heart of downtown Kona, HI. Conveniently located on the gentle slopes of Hualalai. Escape the heat with cool breezes in a tropical landscape setting. Nearby shopping, dining, and entertainment. Fully stocked...
Kolea 1E - 3 Bedroom Oceanview Vacation Rental
Kolea 1E is located in the luxurious community of Kolea in Waikoloa Beach Resort. Its location within the complex gives you the easiest access to the Hilton Waikoloa, which guests of Waikoloa Vacation Rentals have access to. As you enter into the villa off of your...
Hale Lani – Heavenly Lanikai Hillside Luxury
Perched on the northern shores of Oahu in Lanikai, Hale Lani lives up to its name as a true "house in the heavens." This hillside retreat blends sweeping ocean views, open-air design, and effortless island living into a one-of-a-kind vacation home. With 3 bedrooms, 4...
Resort Style with Hula Show, Fireworks and even Tiki Torches!
The Ilikai is the first hotel-resort condominium developed in Hawaii and is one of the original landmarks of Waikiki. It is best known for being featured in the Hawaii 50 TV series and is loved by tourist and locals alike. Conveniently located in Waikiki next to the...
Alana by the Waves - Oceanfront Home in Napili
Stunning Oceanfront Retreat in Napili, MauiPerched above a secluded bay and wrapped in lush tropical greenery, this private oceanfront home is a true Napili gem. Enjoy sweeping, unobstructed ocean views and a rare sense of seclusion that makes it feel like your own...
Beautiful Lae Nani - Oceanfront 2 bedroom 2 bath condo with AC
For your comfort, new split air conditioners have been installed in the living room/dining area and both bedrooms. This recently remodeled and updated resort style condo with majestic ocean views is located on the bay on the Coconut Coast of the island of Kauai and is...
Mahana at Kaanapali, Spectacular Oceanfront, Amazing Sunsets & Sea Life Unit1014
You will love the spectacular views from this luxury one bedroom, tenth floor, oceanfront condominium which overlooks Maui's beautiful Kaanapali Beach. It is located in the "Lanai building" at the highly rated Mahana at Kaanapali Resort.With our unobstructed views, we...
Villa Moana 4 Bedroom
This is a listing for the top floor of our larger two-story eight bedroom villa. We sometimes rent just the top floor during certain periods of the year. The top floor is a 1,900 sq. ft. home with 4 bedrooms and 3.5 baths, an expansive covered deck, sliding glass walls...
Villa Moana - Beachfront Perfection
Spacious Luxury Beachfront Private Villa - 8 BR - 3,850 Sq. Ft. - Newly Built. Right on the beach in Kihei. Hosted with aloha and professionalism. Locally owned and operated. If you need more or fewer bedrooms, please send us a note and we can offer a customized rate....
Maui Resort Rentals: Honua Kai Hokulani 713 - Stunning Interior Courtyard 1BR Penthouse Gem w/ Gorgeous Ocean Views!
As the top-floor penthouse gem in the one-and-only column of inner courtyard 1br suites available at Honua Kai, Hokulani 713 is simply the best of the best among Honua Kai 1br suites. Enjoy gorgeous Pacific Ocean and Molokai views from this incredible 1br vantage point....
Ultimate Oceanfront Condo with Stunning Views & AC
Unobstructed knockout views! Imagine yourself in this gorgeous location with amazing front row seats, 30 feet to the Pacific Ocean. Whales, turtles and dolphins swim by right out your door! See the stunning sunsets and views of the volcanic Poipu coast all year from...