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.
Designer Hali'ipua Sunset Sanctuary ~ Hualalai ~ Fire Pit, Personal Concierge
Step into a world of refined beauty at Hali’ipua Sunset Sanctuary, where every detail of the stunning contemporary design—crafted in serene neutral hues—invites you to unwind in luxury. Picture sipping coffee, surrounded by original artwork and custom furnishings,...
One Ocean Mauna Lani Golf Estate 3
Welcome to 6BD Mauna Lani Lux Golf Estate (3) at One Ocean, a brand-new luxurious six-bedroom, six-and-a-half bathroom home built in 2024, nestled in the prestigious Mauna Lani Resort area in Waimea, Hawaii. Perfect for large families or groups of up to ten guests, this...
Adorable with Ocean View at The Cliffs 4209 1/BD 2/BTH
North Shore Living at it's finest! Soak up the Hawaiian sun and salty ocean breezes from this thoughtfully remodeled 1 bedroom, 2 bath condo at The Cliffs in Princeville. With a spacious layout, this airy second floor unit offers a partial ocean view and is just a short...
Luxury OCEAN FRONT Truly 5 Star with A/C, 20' From The Water At Pikake. No fees
Escape to paradise with our exquisite 1-bedroom, 1-bathroom beachfront condo located on the desirable West side of Maui, between Lahaina and Kapalua. Newly installed split unit air conditioning in bedroom and living room!! This stunning second-floor property offers 518...
Beautiful Oceanview Home
Welcome to paradise.This is a private entire house rental with an operator residing on the building site, If any problems arise we are here 24/7 to help, make recommendations, give directions etc, but we keep a low profile and do not use any amenities when guests are in...
Affordable Luxury Oceanview 3/2 @ Hali'i Kai 8H-Family Friendly!
Who says "family friendly" can't have elegant style and fantastic amenities? Our quiet, ground floor unit (8H) has all of the features that you'd like, and a price point that makes it easy to stay longer... Just check our reviews! This has been our "escape from the...
Experience Paradise Summer Special: Updated Kapalua Golf Villa 5-Star Ocean View
Our condo, 26T8 Kapalua Golf Villas, has everything you need for a perfect vacation:COMFORT: Central air conditioning, remodeled kitchen, new furniture, newly carpeted and painted, king bed upstairs, and new sleeper sofa with a memory foam mattress downstairs. VIEW: Our...
Comfortable House close to beaches with Peloton Bike+ and 4 New Trek bikes
Very cute, Newly-remodeled cottage with a modern garage that has been turned into home gym with mat, weights, peloton bike+, and home office table, chairs and monitor. The interiors have completely been redone with new flooring, furniture, new kitchen countertops and...
Maui Kai 306 Oceanfront Condo, Fantastic Ocean Views
MAUI OCEANFRONT CONDOMINIUM... PREMIUM STUDIO... Third Floor.Note: Please read our Guest ReviewsPrime third floor location provides privacy and the best view of ocean surf, whales and sea turtles. Instead of waking up in the mornings to four walls in a tiny one bedroom,...
Maui Townhome across the Street from Pohaku Beach w/ Incredible Ocean Views
We are conveniently located between Kaanapali and Kapalua on Maui’s world famous west coast. Kahana Villa is across the street from Pohaku Beach (S-Turns Park) with white sand and where turtles frequent. You can watch whales from the lanai and master bedroom! All...
Hale Akaka Falls O-121 one of a kind luxury stay
Welcome to Paradise at Hale Akaka Falls O-121Discover the beauty and elegance of this stunning three-bedroom, three-bath villa located in the prestigious Beach Villas at Ko Olina Resort. This luxurious, ground-floor home offers a rare combination of comfort, style, and...
Includes Beach Gear! Kanaloa 303
Complimentary Late Check Out up to 7:00pm for stays of 5 nights or more between October 1-December 19, 2025 (stay must be complete by December 19th) based on availability at the time of booking. Please message us to inquire about the availability of late checkout on...
Kona Islander Inn - #316 - Located in beachfront town of Kailua Kona Hawaii.
Experience the convenience of being close to popular beaches, shops, restaurants, and historic landmarks with this delightful and cozy retreat. Ideal for explorers and relaxers alike, it is your perfect base for memorable adventures and relaxation. You can walk to many...
Breathtaking Views! - Oceanfront! Mahana 813!
BREATHTAKING VIEWS OCEAN FRONT STUDIO MAHANA 813! NORTH KAANAPALI BEACH, A/CWelcome to Mahana 813! Located on the eighth-floor, this oceanfront studio sleeps 2 and features stunning panoramic views of the ocean, beach and outer islands. Living area highlights include...
!New Remodel Oceanview Waikiki AlaWai AlaMoana
New remodeled private, high rise studio in a secured apartment on Niu Street (Waikiki) with ocean view, Diamond head, city light, Ala Wai Canal view. Walking distance to Convention Center, Ala Moana, beaches, shops and eateries.Please inquire about other listings in...
HALE ONA LOA: DIRECT OCEANFRONT, GATED, 4 BEDROOM, 3 BATHROOM HOME!
Hale Ona Loa – Iconic Oceanfront Luxury on Alii DriveNEWLY REMODELED | OCEANFRONT | PRIVATE POOL | DESIGNER FINISHESStep into coastal elegance at Hale Ona Loa, one of the most spectacularly reimagined oceanfront vacation homes along famed Alii Drive. This fully...
Private Family Oasis Centrally Located by the Beach & All the Local Activities
The Riverhouse at River Estate is a warm and inviting three-bedroom, two-bathroom sanctuary thoughtfully designed to blend timeless Hawaiian charm with modern comforts—perfect for families seeking both relaxation and adventure on Kauai’s North Shore. Inside, the...
Million Dollar Views Oceanfront Studio at The Whaler in Ka'anapali
Aloha! Welcome to Unit #764 at the beautiful and world-famous Ka'anapali Beach and the Whaler! Ka'anapali Beach is a destination featured on the Travel Channel and rated as one of the best beaches in the USA. The Whaler is a popular luxurious ocean front resort in the...
Westin Ka'anapali 2 Bedroom Oceanview as low as 600 per night
Book a whole week for 4950 plus tax or nightly for as low as 600 per night. (Check calendar for availability)The luxury vacation villas at this resort feature large lanais, stone flooring, granite counter tops, roomy bathrooms, fully equipped kitchens, washer/dryer, and...
Romantic cottage with stunning ocean and mountain views in Captain Cook, HI
Enjoy spectacular views of Kealakekua bay in the newly built Coffee Cottage in Captain Cook, Hawaii! Situated amongst the coffee trees at a pleasant 1350 ft. elevation, it’s a perfect temperature year round. Stretch out in the California king bed and check out that...
Wyndham Royal Garden Studio
WYNDHAM ROYAL GARDEN RESORT440 Olohana St.Honolulu, HI 96815• THE PERFECT LOCATION FOR WAIKIKI• GOLD CROWN RESORT• NEAR FAMOUS SHOPPING• 10-MINUTE WALK TO THE BEACH• RELAX ON YOUR PERSONAL LANAI OVERLOOKING THE CITY• COME HOME TO THE POOL, and TWO INDOOR...
Waikiki Living, 4 blocks from surf, mountain views, king size bed and office!
Sunrise on the surf, sunset on the beach, dinner at the top of Waikiki. Enjoy views of Ala Wai canal, Ko'olau mountains and the new park on Aloha Drive from spacious lanais, including your own private lanai. Equipped with A/C, smart TV, microwave and a full kitchen to...
🌺Waiulaula Condo 180 Degree Ocean View 🌺 Member of The Club
Welcome to one of the most beautiful properties within the private gated community of Wai’Ula’Ula at Mauna Kea resort! This upstairs unit, facing out onto the west coast of Hawaii affords a true 180 degree of the Kona coast. One of the most stunning views within the...
Northshore - Paia Beach Town
Walk to the beach and everything in Paia Town. Paia Family House is very spacious, well equipped, with a variety of comfortable indoor, and sweet outdoor living spaces for everyone! There's a yard where kids can play, and views out over the green cane fields. This 4...
Villas By The Cove, Penthouse I · Modern Oceanview Townhome Steps to the Beach!
Welcome to the newest addition to the Villas by The Cove, our Oceanview Penthouse I. This modern home has stunning ocean views, three bedrooms and three full baths, private gated parking, private lanais on both levels, and a large shared heated saline pool and bbq...
Kiahuna Plant. Ground Floor #114,AC, Athletic Club, Tennis Courts and much more
Welcome to Sunny Poipu Beach! Enjoy this ground floor, newly decorated condo and relax on your private lanai while being steps to the sand. Surf spots, long walks and lifeguarded beach are at your fingertips. Fast 200mgb Wifi, fully stocked kitchen, free parking, 24...
KBM Resorts | FREE CAR | Kapalua Bay Villa | Oceanfront | 1-Bedroom Condo, Gorgeously Remodeled! KBV-26B1
Breathtaking oceanfront villa at Kapalua Bay Villas with private lanai, stunning Molokai views, and unmatched privacy-perfect for a serene Maui escape just steps from the ocean and nearby pools.** Limited Time Special Offer: Reserve any KBM Resorts property in Hawaii...
Luxury Aloha Escape Turtle Bay - Kuilima Estates West
Stay comfortably in Kahuku at this 2-bedroom condo. Experience the enchanting atmosphere of this cozy retreat, complete with a king bed and a twin bed. Enjoy the peaceful surroundings and modern amenities like WiFi, AC, and a washing machine. Relax in the living room...
Magic Sands Light Hawaii Oasis: Steps to Beach, AC ,No Cleaning Fee!
High in Demand & Highly Rated, this beautiful 3 bedroom / 2 bathroom duplex home is only a 3 min walk from Magic Sands Beach. Remodeled & professionally decorated, this charming vacation getaway has all of the comforts you desire in your home away from home, including...
Magnificent Mauna Kea Home With Stunning Views
This 7,768 square foot home was designed by Hawaiian architect Thomas Bingham (a protege of Frank Lloyd Wright) for indoor/outdoor living and entertainment. It has 5 bedrooms, each with a private bath, the master suite enjoying complete privacy on its own floor. The...
Penthouse - 3 Bedrooms 2 Baths
Welcome to our Paradise Home come and relax in luxurious surroundings at our tropical condo, which has been freshly painted, and new air conditioner installed and kitchen renovation, new King Mattress. ( Winter 2016). New appliances, carpet and furniture (2017).Bathroom...
Kapalua's Finest: Luxe Villas with White Sand Beach Access
Nestled in lush gardens and beside pristine beaches, our secluded sanctuaries offer tranquility. Enjoy world-class golf, snorkeling, award-winning spa treatments, and farm-to-table dining. Experience luxury in our fully-equipped villas, with stunning sunsets from your...
Maui, island of the Haleakala Volcano is the heart chakra of the earth
Kapalua's history began in 1836 with Dr. Dwight Baldwin's royal land grant, evolving from an agricultural area (Honolua Ranch/Plantation) to a luxury resort, now known for its golf courses, beaches, and upscale amenitiesKapalua simply is 'A Place Of Life', perfectly...
New Listing In Princeville ~Heated Pool/Jacuzzi
Steps away from the Heated Pool, Jacuzzi and Gas BBQ Grills... This sunlit retreat is designed for a Couples Getaway or Family Adventure. Nestled in the heart of Kauai's lush North Shore, this ground-floor condo combines island charm with all the comforts of home. With...
Kilohana At Poipu By Parrish Kauai - Private Pool with AC - Great for the Family
Kilohana at Poipu is a private tranquil vacation home nestled in the center of Kiahuna Golf Village and the Robert Trent Jones, Jr. golf course. This single-level home has a spacious indoor/outdoor living layout centered around a heated swimming pool and courtyard,...
Alii Villas #230 Direct view into Kailua Bay
Fabulous 2nd story condo with an oceanfront view! Located on the desirable Kailua Bay side of Alii Villas Condominiums. Beautifully decorated and well appointed for your comfort while on the Big Island. Fully furnished with everything you need for an relaxing vacation....
Beautifully Upgraded, Beachfront, Ground Floor....Dream Vacation!!! #118
Kanai A Nalu (“Gentle Breeze”) is located in Maalaea; a place often called “Maui’s best kept secret”. Our condo is direct OCEANFRONT, BEACHFRONT! You simply cannot get any closer to the ocean than our beautifully upgraded, ground floor unit!From the lanai,...
Alii Cove C-4 Beautiful Beachy Townhome on Alii Drive
Experience the allure of the Alii Cove C-4 Town-home, where exquisite decor meets cozy comfort, perfect for entertaining large gatherings while radiating that charming beach house vibe. The expansive Primary suite exudes glamour and luxury, featuring sumptuous bedding...
Oceanfront Condo, 5G Wi-Fi, King Bed, Hot Tub/Pool, Free Parking
Was recently completely remodeled.Our oceanfront condo is 23ft. from the ocean and is located on the 2nd floor and offers spectacular ocean views and sunsets.Watch the surfers and the dolphins from your lanai. A Short Walk to town and over 20 restaurants.Our...
Wailea Elua 3 Bedroom+2 Bath Spacious Beach Home with Oceanview Lanai
This is the one! A real Maui home-away-from-home. If you are looking for an impressive vacation home with new Ohia wood cabinets, cupboards, and accents in the kitchen, new sandstone tile flooring, super quiet new Fleetwood glass doors, new Miele appliances, and new...
!DISCOUNTED RATES! FULL ocean view. Rated "EXCEPTIONAL". Renovated. Top Floor.
**The condo is already booked 65% in 2025. I've HEAVILY discounted some dates in 2025. Reserve your stay today before your dates are gone.****NEW elevator just completed 7/2025.****Hale Ono Loa Condos, the resorts at Ka'anapali, the Whalers Village, and Northward...
New Listing! Stunning 2bd condo with ocean views
Welcome to Polynesian Shores 211 – your perfect island getaway! This spacious second-floor condo has 2 bedrooms and 2 bathrooms, comfortably accommodating up to 6 guests. The primary bedroom boasts a cozy king bed and a private ensuite. The second bedroom features two...
PANORAMIC GOLF COURSE VIEW HOME "C", MODERN-CLEAN-GATED, NEAR PEARL HARBOR-JBPHH
Welcome to Hillside Perfection on the Greens at Golf Ridge Homes!Discover your ideal fully furnished, 5 bedroom, 4.5 bath air conditioned executive home located in central Honolulu. Perfect for leisure visitors, savvy business travelers and visiting construction teams...
Stunning Kaikea 4Br/4Ba Estate: Luxurious and Private - 5 min from Lanikai Beach
Welcome to Kaikea - a tropical oasis nestled just a short walk away from the pristine white sand and turquoise waters of Lanikai Beach, offering an unparalleled experience of luxury and relaxation. Comprised of two separate structures- one newly built in 2018, along...
Spacious 3BR/2.5BA Townhome in Quiet Ko Olina - Pool, Beaches & Golf Nearby
Escape to our cozy, peaceful 3-bedroom, 2.5-bath townhouse in the serene Hillside Villas at Ko Olina. Just minutes from world-class beaches, golf, and restaurants, our home offers the perfect blend of comfort and convenience for your tropical getaway. Nestled in a...
Guaranteed 2024 Thanksgiving, Christmas & New Years Weeks In Maui, Westin Villas
** Guaranteed dates: 12/20/2025 - 12/27/2027 ****Please email me to inquire about dates before submitting a reservation request**12/20 - 12/27 - Westin Kaanapali Villas North - 2 BR unit - Island View - sleeps 8 (flexible on price)Have you been to Maui? It's time! Come...
Two Bedroom Oasis!
This upscale, high end condo has all the amenities and comforts you could ever want in a vacation rental. A large dining table is located on the lanai where you can sit and watch the whales, boats and surfers. The weekend brings the canoe club and kayakers going by your...
Aloha Condos, Keauhou Resort, Condo 108, Ocean View, AC
Experience perfection at Keauhou Resort Condo 108! This immaculate, renovated condo offers stunning ocean views, breathtaking sunsets, and stellar stargazing from your private lanai. Enjoy top-notch amenities, a fully equipped kitchen, updated appliances, and the most...
2 Bedroom Garden View - Maui Banyan #T108AB
Maui Banyan T108AB: With a functional floor plan and connecting door make this the ideal two-bedroom/two-bathroom ground floor unit for a family getaway. Exotic patterns and warm color tones set the mood while oversized windows allow for natural light and serene garden...
G302: Remodeled Maui Condo with Ocean & Sunset Views, Updated Kitchen & Baths
Beautifully remodeled home at one of Maui’s favorite properties! G302 is one of a handful of condos on property with a fantastic ocean and sunset view as well as views of Haleakala all from your own lanai. The kitchen and both baths have been fully updated. New vinyl...