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.
Hale Hau`oli ~ FAIRWAYS TERRACE H104 ~ 2 BR / 2 BA ~ Pool/Spa/BBQ ~ Gym ~
Summary:Hale Hau'oli - Located on the western slope of Mauna Kea our 2 bedroom 2 bath condo in Waikoloa Village sits on the Robert Trent Jones golf course (The Village Course). Enjoy the benefits of the 900’ elevation with warm days and cool mornings and evenings. This...
Gorgeous Kapalua Home with Views
This gorgeous Maui home is a two story end unit with expansive ocean views from lanais on each level! Located in the renowned Kapalua resort area on the northern coast of Maui, you are not only close to the beach (less than a 5 minute walk, to be exact), but within...
Beachfront on Kaanapali Mahana 1106!
SPECTACULAR 11TH FLOOR OCEAN FRONT MAHANA 1106! KAANAPALI BEACH, A/CWelcome to Mahana 1106! Located on the eleventh-floor, this one bedroom, one bath condo sleeps 2-4 and features stunning panoramic views of the ocean, beach and outer islands from the living room,...
KBM Resorts | FREE CAR | Kapalua Golf Villa | Ocean view | Luxury 2-Bedroom Villa with Panoramic views! KGV-22P2
** 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...
Recent RENO! Fits 6, FREE parking
You & your family or friends will be close to everything at this centrally-located oasis in Waikiki. A couple minutes to the beach, surfing, the lagoon, boating & fishing, hiking, restaurants of every kind, shopping galore, everything Hawaii has to offer for a tropical...
Ocean View Condo with 3 shared pools, beach access, grill areas, & more!
Plantation Hale F5Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'*BOOK MAY 28-JUNE 2, 2025 FOR A DISCOUNTED NIGHTLY RATE*Located in the heart of Wailua, on the Royal Coconut Coast...
Kamaole Sands 7-405 - Stunning Renovation, Large Lanai, Ocean Views, Split AC!
Welcome to Kamaole Sands 7-405, your luxurious tropical escape in the heart of South Kihei, Maui! This stunning top-floor 2-bedroom, 2-bathroom condo is the ultimate destination for an unforgettable island getaway. With breathtaking views of the lush tropical courtyard...
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...
Hoku Hideaway - AC, Ocean Views
*30 day listing. Please Inquire.Hoku Hideaway is a 3-bedroom, 2-bath home that offers the perfect blend of comfort and island charm. Located just across the street from the ocean, it provides easy access to stunning beach views and relaxing coastal breezes. The home...
Tranquil 2-Bedroom Getaway at The Cove Waikiki
Stay in seclusion & serenity at one of Waikiki's newest gems, The Cove Waikiki. This private community is nestled 2 short blocks from Duke Kahanamoku Bay and among Discovery Bay's ample shops, cafes and activities, and easy access to Waikiki, Magic Island Beach Park,...
🏖️Private Pool | Includes Concierge | Private Beach Access | vrKCV
vrKCV - Ka Milo 226 at Mauna Lani, Professionally Managed by Kona Coast Vacations**Act fast! A rare last-minute cancellation means Ka Milo 226 is available for Christmas & New Year's week — this will book quickly.Ka Milo 226 at Mauna Lani Resort: Elegant Island Living...
Kaanapali Ocean Front 1 Bedroom! Mahana 617!
GORGEOUS VIEWS OCEAN FRONT MAHANA 617! KAANAPALI BEACH, A/CWelcome to Mahana 617! This oceanfront one bedroom, one bath condo sleeps 2-4 features stunning panoramic views of the ocean, beach and outer islands from the living room, dining area, bedroom, and lanai. Living...
NEW!! Charming 1-bedroom bungalow in amazing Kona
NEW! NEW! NEW!*professional photos coming soon**Our dream home! Ready to share with you. We have been waiting years to be in this complex! It’s the secret gem in Kona. We put our vision and dreams into a complete remodel September 2024. The kitchen with all new...
ICC 41 Remodeled 3BD Kaanapali Cottage w Heated Pool
International Colony Club 41 Spacious and Beautifully Remodeled Kaanapali Cottage, Rare 3Bedroom, 2Bathroom, Walk to the Beach! FREE daily activities included with your stay value up to $570! Complimentary admission, every day of your stay*: Whale Watch (seasonal),...
Oceanview 1 bedroom Kihei gem, perfect location, walk to everything
Welcome to Island Surf 402. This ocean view centrally located 1 bedroom Kihei condo can accommodate 4 people & has everything needed to feel at home. Cross the street to get to Cove Park & Kalama Park, a favorite for surfing and walking around. This condo is steps away...
Puako's Ocean Edge Modern Estate - Architectural Masterpiece in Puako
Welcome to Puako’s Ocean Edge Modern Estate, an architectural tour de force on Puako’s oceanfront. Spanning 4,085 sq ft of refined interiors and 3,415 sq ft of shaded lanais, this four-bedroom, five-and-a-half-bath retreat fuses world-class design with unrivaled coastal...
Makahuena Condo #1-304 - Modern Oceanview 2 Bedroom Condo With Pool
Step into the breezy, island-inspired comfort of Makahuena 1-304, where stunning ocean views and the charm of Kauai’s southern shore await you. This beautifully updated two-story condo offers 1,113 square feet of living space and includes 2 bedrooms and 2.5...
Beach Front Condo South Maui
Welcome to our serene beachfront condo, a perfect blend of comfort, convenience, and coastal charm. Nestled on the edge of a breathtaking beach, this family-friendly retreat offers not just a stay, but an experience to cherish. With its soothing interiors a wealth of...
Maui Tropical Sunset - High Demand First Floor Condo with All The Extras!
Maui Tropical Sunset | High-Demand First Floor Condo at the Ocean Front Royal Kahana Resort | Private Lanai | No-Stairs Entrance | Ocean Views | Private Workspace | Fast Wi-Fi | Air Conditioning | Walk-in Shower | Washer & Dryer | Beach Toys | Resort Concierge | Heated...
New Listing! 30% Off - Thru 4/30/25! Beachfront, Family Friendly, AC & Pool!
Welcome to Kahana Village Residence 37, a stunning 3-bedroom, 2-bath unit in West Maui. Offering breathtaking ocean views and an exceptional direct oceanfront location, this condominium provides the ultimate Hawaiian getaway. The lush green space in front of the unit...
Maui Vista Top floor 2-bed condo in central South Kihei Walk to shops and beach
Aloha, A beautifully renovated top floor 2 bed 2 bath, with vaulted ceilings and fantastic amenities. The unit faces Maalaea Bay and the West Maui Mountain. Elevator access to the unit makes it very convenient for all ages; parking is free, no resort fees.Building 3 is...
Poipu Beach Making Memories, 2-Bedroom, AC, Pool & Walk to the Beach, Kauai, HI
Experience Poipu Beach and make memories at this 2-bedroom condo at Kahala in the Poipu Kai Resort. From the moment you enter this ground floor-end unit with 1150 square-feet and quiet peaceful garden view, you will feel like you've entered a true Hawaiian paradise. The...
One Ocean Mauna Lani Golf Estate 4 with Infinity Pool & Spa
Welcome to 6BD Mauna Lani Lux Golf Estate (4) at One Ocean, an architectural showpiece completed in 2024 within the gated One Ocean enclave of Mauna Lani Resort. Designed for modern island living, this six-bedroom, six-and-a-half-bath retreat unfolds across open,...
Ocean & Diamond Head View Condo at Waikiki+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...
Relaxation Bungalow with Hot tub, Sauna, Lush Garden, and Pristine Island Living
Escape to Hale Kalani, a charming 3-bedroom surf bungalow nestled in the heart of Princeville on Kauai’s renowned North Shore. Thoughtfully designed for relaxation and island living, this single-level haven features a private cedar barrel sauna, a brand-new hot tub, and...
Maui Resort Rentals: Honua Kai Konea 726 – Luxurious 7th Floor 2BR w/ XL Balcony & Delightful West Maui Mountain Views!
Konea 726 offers nearly 1300 sq ft of spacious interior living area and an additional XL 350 sq ft balcony. Enjoy gorgeous vistas of the West Maui Mountains and the frequent afternoon rainbows from a 7th floor vantage point.The suite can accommodate up to six guests in...
Bright & Airy Princeville Home with High-Speed WiFi, Private W/D, & Gas Grill
Enjoy a relaxing Kauai vacation in this open and airy Princeville home. With sky-high ceilings, exposed beams, and plenty of natural light, you'll feel right at home. The kitchen features full-size appliances, perfect for preparing meals, and the wraparound lanai offers...
Spacious two-bedroom split-level Kihei condo
Welcome to Maui Kamaole M210, a stunning 2-bedroom, 2-bathroom split-level condo that combines modern comfort with tropical island charm. Located in one of Maui's most sought-after complexes, this beautiful retreat offers everything you Welcome to Maui Kamaole M210, a...
Stunning ocean view! 2/2 in the heart of Wailea
Beautiful, spacious, modern 2/2 condo located in the heart of the Wailea Resort area with gorgeous, far-reaching ocean and island views, and surrounded by brilliant, lush, flowery grounds. Super-close to dining, golf, shopping, and only a short stroll to award-winning...
Wailea Ekolu 1106 May & June Deals at Remodel Condo for Peaceful Island Getaway
The Stice Team — Powered by Gather Vacations. Maui Born and Raised Professionals. Your Local Experts in Crafting Unforgettable Stays.Welcome to Wailea Ekolu 1106, a newly remodeled 2-bedroom, 2-bath upper-level townhome tucked into the serene Wailea Ekolu Village on...
Kapalua Ridge 1421 40%Off May Deals for Relaxing Getaway at Remodeled Condo
The Stice Team — Powered by Gather Vacations. Maui Born and Raised Professionals. Your Local Experts in Crafting Unforgettable Stays.Welcome to Kapalua Ridge 1421, a masterfully re-imagined 1-bedroom, 2-bath townhome perched on the second floor of Kapalua Ridge Villas...
Honua Kai H825 Luxurious Kaanapali Beach 3BD Condo with Beautiful Ocean Views
The Stice Team — Powered by Gather Vacations. Maui Born and Raised Professionals. Your Local Experts in Crafting Unforgettable Stays.Welcome to Honua Kai Hokulani 825, an eighth-floor 3-bedroom, 3-bath penthouse style residence that sleeps up to 10 guests and frames...
Kaanapali Shores 702 Find Your Next Summer Escape at Beautiful Beachfront Condo
The Stice Team — Powered by Gather Vacations. Maui Born and Raised Professionals. Your Local Experts in Crafting Unforgettable Stays.Welcome to Kaanapali Shores 702, a show-stopping direct-oceanfront residence perched on the 7th floor of the acclaimed Kaanapali Shores...
Mahana 1119 Early Summer Deal at Luxurious Condo with Panoramic Ocean Views
Welcome to Mahana 1119, an eleventh-floor 2-bedroom, 2-bath corner penthouse that sleeps up to 6 guests and occupies Mahana’s most coveted stack, renowned for delivering Maui’s single most breathtaking ocean, outer-island, and beach panorama. The moment the front door...
Royal Kahana 610 50%Off Last Minute April Deal at Remodeled OceanFront Condo
The Stice Team — Powered by Gather Vacations. Maui Born and Raised Professionals. Your Local Experts in Crafting Unforgettable Stays.Welcome to Royal Kahana 610, a rare sixth-floor corner 2-bedroom, 2.5-bath ocean-front sanctuary that stretches across 1,400 sq ft and...
Luxurious 3-Bedroom, The Villages at Mauna Lani #325
Luxurious 3-Bedroom Villa at The Villages at Mauna Lani | Hawaii Dream GetawayWelcome to your private slice of paradise! This stunning 3-bedroom, 3-bathroom luxury villa located in The Villages at Mauna Lani offers the perfect blend of relaxation and elegance, with a...
Architectural Stunner in Kukui'ula - 4 BR Oceanview Villa with Infinity Pool & Spa
With its captivating ambience, dramatic wood, glass and board-formed concrete architecture, and exhilarating views, Hale Oma'oma'o—this irresistibly inviting new Kukui'ula villa—offers all the expected attractions, along with a great many pleasant surprises. The...
Lazy Lehua Cottage
Serenity, peace, and rejuvenation is here at this private cottage on a half-acre of upcountry rainforest. Lazy Lehua Cottage is for settled or adventurous couples, small families, honeymooners, artists, poets, musicians, scientists, and writers. The native birds sing...
Stunning Ocean Front Studio! Mahana 803!
STUNNING VIEWS OCEAN FRONT STUDIO MAHANA 803! NORTH KAANAPALI BEACH, A/CWelcome to Mahana 803! 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 tile...
Large Ocean View 2-bedroom condo with AC and WiFi in wonderful Wailea-Makena
Enjoy the comfort and cleanliness of your own space. Located in the heart of Wailea, Grand Champions Villas is next to a golf course, tennis courts, a short walk from the Shops of Wailea, restaurants and a 5 minute drive to Wailea Beach. Open floor plan living area...
Aloha Condos, Kanaloa at Kona, Condo 3103, Oceanfront, AC
Kanaloa at Kona Condo 3103 is a wonderful place to stay in Hawaii. Located next to the ocean, it offers stunning views and is fully furnished with everything needed, including a well-equipped kitchen, beach gear, and amenities like pools. Guests praise its cleanliness,...
Maui Resort Rentals: The Whaler 1061 - Upgraded 10th Floor Studio w/ Stunning Pacific Ocean and Mountain Views!
Perched high above the palm fronds, guests are treated to unobstructed views of the tranquil blue Pacific and the soft sands of world-renowned Kaanapali Beach from this luxurious 10th-floor studio suite. Fold away the floor-to-ceiling glass doors and step out onto your...
Hale Kipa Ohana
Experience our Beautiful town of Waimea in this 3-bedroom 2 bath home on a one acre parcel. This home gives you the Country tranquil setting of the Kohala mountains surrounded by the lush green outdoors. A great yard to play volleyball and any outdoor sports. A play...
Gorgeous Mauna Lani Townhome: Near Beach / Luxury Amenity Center
Gorgeous townhome in the Kulalani at Mauna Lani community. This sleek, well decorated two-story home offers private Beach Club access, close proximity to the luxurious Kulalani Amenity Center, a patio with a gas BBQ and an expansive lawn surrounding the building for...
Luxe 1BD Condo w/ Ocean Views @ Maui Banyan Resort
Relax in our pristine 1-bedroom condo at the Maui Banyan Resort, just a few steps from the gentle, sandy shores. Take in glimpses of the ocean from the lanai and embrace the aloha spirit.✓ Right across the street from Kamaole Beach II✓ King bed + 1 Queen pullout sofa✓ 2...
Cute Seaview Studio! Steps from Kamaole 2 Beach & Pool 🌺 Maui Banyan Resort
Relax in our cute studio apartment at the Maui Banyan Resort, just a few steps from the gentle, sandy shores. Take in glimpses of the ocean from the lanai and embrace the aloha spirit.✓ Right across the street from Kamaole Beach II✓ Kitchenette w/ microwave + fridge +...
May Sale - Stunning End Unit with Amazing Lanai Views at the Beach Villas Resort
Escape to paradise in this beautifully appointed high-floor villa at the exclusive Beach Villas Resort in Ko Olina.This spacious end unit offers panoramic ocean views, refreshing breezes, and the perfect setting for a luxurious Hawaiian getaway. As owners who spend...
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...
Tropical Paradise Awaits at Maui Kamaole L107. Across from 2 Fave Beaches!
* Coastal Living! Updated in 2024! * 1 Bedroom/ 2 Baths-Sleeps 4* Across from 2 Popular Beaches* Ground Floor and Near the PoolExperience the perfect blend of luxury and convenience at Maui Kamaole L107. This newly updated ground floor condo boasts fresh paint, stylish...
Maui Parkshore 416: two bedroom condo with stunning view of the ocean.
Maui Parkshore 416: two bedroom condo with stunning view of the ocean.Stunning, unobstructed ocean views from this two bedroom corner condo. The bright and open living area opens to a large lanai, extending the living area. The primary bedroom has a king bed and the...