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.
Wailea Grand Champions | 177
Welcome to Maui's Wailea Grand Champions, a paradise nestled in the heart of Wailea. This exquisite one-bedroom, two-bathroom vacation rental offers the perfect blend of comfort, luxury, and breathtaking views, ideal for couples or small families seeking an...
PK A108 Remodeled OceanFront w Panoramic Ocean Views
Papakea A108 NEW LISTING Remodeled OceanFront Papakea 1Bedroom with Panoramic Ocean Views for Front Row Sunsets and Year Round Indoor-Outdoor Living FREE daily activities included with your stay value up to $570! Complimentary admission, every day of your stay*: Whale...
NAUTICAL THEME GARDEN VIEW STUDIO - KONA ISLANDER INN CONDOS by RedAwning
**NAUTICAL THEMED UNIQUE CONDO HAS BEEN COMPLETELY REMODELED - DOWNTOWN,**TAKE A LOOK, YOU WILL WANT TO STAY HERE, HAS QUEEN SIZE MURPHY BED,KITCHENETTE WITH **INDUCTION COOKTOP, FULL SIZE MICROWAVE, FULL SIZE FRIDGE,ALL OF THE COOKING ITEMS YOU WILL EVER NEED AND...
Studio City View Kitchenette, A/C and WiFi - Bamboo Waikīkī Hotel #205
Castle Bamboo Waikīkī Hotel #205 - This second-floor, 318 square-foot unit accommodates three guests and is furnished with a large cozy sofa and a spacious Queen bed with fresh linens to ensure a peaceful rest. The studio has a flat-screen TV, iPod docking station,...
Whale Watching from Artist Inspired Retreat 2 Oceanfront Lanais AC
The Space:Welcome to our spacious oceanfront home "Kahana Sunset A9" conveniently located at the prime location in the heart of West Maui!✔ Oceanfront Home with breathtaking oceanfront views of Lanai and Moloka’i✔ Air Conditioning (A/C)✔ A heated swimming...
Wailea Oceanfront Center Front Row Luxury Retreat
Immerse yourself in the beauty of Maui at this stunning oceanfront property. This 2-bedroom, 2-bathroom condo offers center unit front row access of the Pacific Ocean.The primary bedroom features a king-sized bed with direct access to the lanai. The second bedroom...
Tranquil and Chic 1 Bd and Bth with Car and Sauna
"Tutu's Hale" a hidden tropical oasis in East Honolulu, features 1 bedroom and 1 bath, living room, kitchen, walk-in closet, outdoor patio space with hammock swings and furniture, with access to our shared dry sauna, cold plunge and outdoor shower. Those in need of...
Golf Villas Partial Ocean View 1 Bedroom at The Kapalua Villas Maui
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...
North Shore home with views of sunsets and migrating whales
This beautiful three-bedroom home is situated in a gated community overlooking Ke-Iki Beach on Oahu's North Shore. Our location is prime: It is only a 40-minute drive from Honolulu Airport. Shark's Cove, THE BEST place to snorkel on the island, is a 10-minute walk away....
Poipu Kai Kahala 921 - One-bedroom Garden View
Poipu Kai Kahala 921 - One-bedroom Garden View condo on the island of Kaua'i. Primary bedroom: King BedBathroom: full bath ensuiteOccupancy: 2AC: noneLaundry: in condoCoffee maker: BrewTV: livingroom and bedroomThis highly sought-after property is located on the island...
2nd Floor Beachfront 1 Bedroom Apt. Sans Souci 204
Monthly Rental.Treat yourself to this spacious 1 bedroom 2nd floor apartment above the golden sands of Kaimana Beach on Honolulu's Gold Coast.With a great private lanai that looks out over the beach and Pacific ocean, relaxing will not be an issue. The sound of the...
Suite on North Shore property. Walk to beach & town!
The Ho'okipa Surf Suite is located on the rear part of a private ocean front property on the North Shore of beautiful Maui. We are less than 5 minutes from world class surf breaks, kite and wind surfing beaches. The rental contains 1 bedroom, 1 bathroom, living area &...
Maui Resort Rentals: Honua Kai Hokulani 301 – 3rd Floor Ocean Front Crown Jewel 3BR w/ B.B.Q on Balcony!
Maui Resort Rentals is proud to present this phenomenal 3BR residence at the Honua Kai Resort—newly launched on 2/6/2025 to start taking bookings on March 7th, 2025!Commanding an incredible interior 3rd-floor vantage point in the closest column to the ocean at the...
Kiahuna Plantation Resort 116 Partial Ocean 2BD 2B
- Nicely appointed, newly furnished, two-story condo with beds and baths downstairs and living areas upstairs looking across the grounds to the ocean - Walk-up, no elevators- Carpet in living, dining and bedroom areas with tile in kitchen and baths- Full kitchen with...
Tropical Retreat with Heated Pool in Ilikai Hotel
Our spacious apartment is designed to provide you with all the comforts of home, plus the added benefits of a resort-style setting. The unit features two beautifully appointed bedrooms. The master bedroom serves as a serene retreat with a plush king bed, offering a...
Royal Sea Cliff Kona Oceanfront 1 Bedroom
Ocean Front 1 Bedroom- Condos located on 3rd floor- Private balcony- Kitchen features stovetop, oven, refrigerator, microwave, dishwasher, coffeemaker, blender, cookware and tableware- Bedroom with 1 king bed- Queen sofa bed in living area- 850-925 sqft/79-86 sqm-...
Kapalua Bay 27G3 Gold Oceanfront 1B 2B +Bonus Room
- Villa closest to Oneloa Beach- Split level condo with 17 stairs between parking and front door and 25 steps to Pool C- Travertine floor flooring in living area- Updated kitchen with stainless steel appliances and granite counters – fridge with ice maker, stove/oven,...
New- Beach Condo an easy 75 steps to the Beach, Pool, Restaurants.
Make yourself at home in this 2-bedroom Kihei retreat. This welcoming condo offers a beautiful living room with a cozy futon for extra guests. With amenities like AC, WiFi, and an iron, guests can relax and unwind after a day of exploring. The two bathrooms ensure...
Royal Kahana Maui 813 Oceanfront 1 Bedroom
- 8th floor condo with balcony- Vinyl flooring throughout- fully equipped kitchen with– fridge, stove/oven, microwave, cookware, tableware- Tiled bathroom with walk-in tiled shower with grab bar- Bedroom with 1 king bed- Queen sofa bed in living area- Washer/dryer in...
Discover Tropical Bliss: Marriott's Maui Ocean Club - Your Hawaiian Dream- 1 Bd.
Cozy yet spacious. Intimate yet extensive. This one-bedroom features luxurious comfort for memories together and space to escape.If you’re searching for the quintessential Hawaiian getaway, then this resort is quite the catch. If the sunshine, beaches, and glowing...
Honua Kai Resort: Luana Upper Villa 18D with Pool View
This luxurious upper-level villa at Honua Kai Resort offers an exceptional opportunity to experience the best of Maui living. With over 2,000 square feet of sophisticated interior space, this villa is designed for comfort, style, and convenience. Featuring 3 spacious...
Maui Kā’anapali Villas 285
Maui Kā’anapali Villas 285: located ocean side in the Emerald building with Ocean and Pool ViewsThe space:The unit is a second floor corner studio which gets the morning sun on the lanai - a great place to have your breakfast and protection from the sun in the heat...
Oceanfront Bliss: Studio Premium Villa at Westin Ka’anapali Ocean Resort North
Elevate your Maui vacation with a stay in the Studio Premium Oceanfront Villa at Westin Ka’anapali Ocean Resort Villas North, where world-class luxury meets breathtaking ocean views and family-friendly fun. Nestled on the pristine shores of Ka’anapali Beach, this is...
Lava Rock Sunset Beach House. Unique oceanfront & pool property. Amazing views!
Paradise Found!! Enjoy a unique Hawaiian experience. Ocean front lava rock beach house has gorgeous ocean sunset and coastline views from all major rooms in our home. Enjoy our Hawaiian style home and relax on the outdoor lenai while enjoying your morning coffee. Watch...
Luxurious Wailea Ekahi 19A - Ground Floor with Ocean Views & Easy Beach Access
Wailea Ekahi #19A – Spacious Townhouse Comfort Near Keawakapu BeachWelcome to Wailea Ekahi #19A, a rare and spacious 2-bedroom, 2-bathroom townhouse nestled within the beautifully landscaped Wailea Ekahi Village. Located just steps from world-famous Keawakapu Beach...
Stylish condo with private lanai, shared pool & hot tub - steps from the beach
Plantation Hale #C5Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Welcome to your tropical oasis in Kapaa, HI! This charming ground floor, end unit condo is the perfect getaway for...
Kulanakauhale 11 – Elegant & Modern | Onsite Staff & Daily Housekeeping
This 4-bedroom, 4.5 bath private home combines pod-style architecture with traditional design to optimize the resort lifestyle for up to 8 guests. Surround yourself in custom contemporary resort furnishings and décor while enjoying expansive golf course and mountain...
Resort living near beach! in Ko Olina
Rarely available golf course frontage 2 bd2.5 bath Orchid unit townhouse (1,350 Sq Ft) inCoconut Plantation. One level ground floor unit with no neighbor above with an open floorplan. Golf course & greenery views throughout. Lots of privacy from neighboring...
Royal Sea Cliff Kona 711 Ocean View 2 Bedroom
- 7th floor condo with covered lanai- Maximum 6 persons including children and infants- King size bed in master bedroom- Queen size bed in second bedroom- Sofa bed with two recliners in living room- Updated kitchen – with fridge, stove/oven, microwave, cookware,...
Stylish Kauai Condo on the Beach
Enjoy the ocean breeze and relax in our calm, stylish space. One of the best swimming beaches on island is downstairs. We even provide our surfboard for you to use!It feels like classic Old Hawaii here at the Islander on the Beach Resort Complex, which is why we love...
Island Haven Hawaiian Monarch Studio | Ocean View
Thoughtfully designed ocean-view studio with flexible sleeping, storage and remote work options. This home offers ac, flatscreen tv, wifi, cable, dining for 4, and cute kitchenette. A prompt walk from Hilton Hawaiian Village, Fort DeRussy Beach Park, Ala Wai Canal and...
Beachfront 3 bedroom penthouse with easy beach access!
Enjoy easy beach access and an amazing view from this three bedroom penthouse at Kolea at Waikoloa Beach Resort. From the minute you walk into the villa you will be struck by the size and amazing view. The large great room has expansive views of the beach and ocean. The...
Stunning 2BR 2BTH OV, WiFi and Cable - Waikīkī Shore PH11
Paradise found in this two-bedroom two-bath space! Enjoy the Pacific blues from this captivating unit located in the heart of Waikīkī. Guests can begin the day with Hawaiian coffee on their private lanai, living room, or dining space.After a day of exploring Oahu,...
Modern & Tropical Oceanside Vistas
Summary:Newly remodeled (June 2022)1 br, 1 bath modern condo with upscale Hawaiian style. Located directly across from the beach in warm & sunny Kihei. Nestled in the exclusive and desirable Kihei Bay Vistas, you will be embraced in the tranquil grounds and ocean views....
One of a Kind Luxury
FEATURED IN ARCHITECTURAL DIGEST MAGAZINE! Are you ready to graduate from the Presidential Suite? Are you looking for the most relaxing vacation accommodation?*Specials not available during Peak Season*This OCEANFRONT CROWN JEWEL – A MODERN DIAMOND HEAD HOME –...
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....
Remodeled Ground floor, Oceanview, AC, steps to Kam II Beach
Freshly remodeled unit top to bottom in a prime South Kihei location. ***Please note: This property is Hotel Zoned and NOT in danger of the possible upcoming short term rental ban.***The layout:Bedroom: King size bed with premium linens, blackout drapes, closet, new...
Westin Nanea - Beautiful Resort On The Beach! Family Friendly Resort
The Westin Nanea Ocean Villas, located on Maui’s famed Ka‘anapali Beach, offers a luxurious Hawaiian getaway. These villa-style accommodations feature full kitchens, private lanais, and spacious living areas. Resort amenities include lagoon-style pools, hot tubs, a...
Ocean Front 3-bedroom house in phenomenal Anahola with WiFi
Experience Anahola like a local in this 3-bedroom house. This charming property features 2 queen beds and 1 bunk bed, perfect for families or friends traveling together. With amenities like heating, WiFi, and a hair dryer, guests will feel right at home. The 2 bathrooms...
Cozy 1-bedroom apartment in amazing Honolulu with WiFi, AC
Located at the riverbank of Ala Wai Canal, you can enjoy the beautiful river view from the balcony. This apartment is remodeled in 2023 with zero VOC paint on the walls for your kids’ safety. Near 7-11 convenience storeVersatile kinds of restaurants Chiba-ken...
Maui Resort Rentals: Kaanapali Ali'i – 4 Total Bedrooms, Luxuriously Remodeled, Premiere Ocean AND West Maui Mountain Views!
This phenomenal four-bedroom offering brings together a 2BR suite with a premier ocean view in one of the best interior stacks at the entire resort with a luxurious neighboring 2BR partial ocean view suite. Together the two neighboring 7th-floor suites offer a combined...
Royal Sea Cliff Kona 103 Garden View 1 Bedroom
- 1st floor condo located very close to the South pool and the BBQ grills- Covered lanai is 154 square feet/14 square meters- Tile flooring throughout unit.- Updated kitchen features all new, stainless steel range, dishwasher, and refrigerator- Bedroom with 1 king bed-...
Ridge Villas Fairway View 1 Bedroom at The Kapalua Villas Maui
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 Resort Rentals: Honua Kai Konea 326 – Luxurious 2BR w/ XL Balcony & Delightful West Maui Mountain Views!
Maui Resort Rentals is proud to bring you this 2BR Partial Ocean View Suite at the Honua Kai Resort, newly launched on May 12th, 2025 to start taking reservations for check-ins on June 21st, 2025!Konea 326 is a remarkable 2BR/2BA suite offering nearly 1,300 square feet...
Charming 1-bedroom condo in lovely Kihei with WiFi, AC
Discover this fantastic 1-bedroom gem in Kihei. This cozy condo features a nice king bed, 2 bathrooms with a bathtub and shower, and convenient amenities like WiFi and AC. The serene atmosphere of this property will make guests feel right at home. You're sure to make...
New Listing! Paradise found, Sea views, lush vibes
Welcome to Kaanapali Shores 512 – your perfect tropical escape on Maui's world-famous Kaanapali Coast. Nestled along the golden sands of West Maui, this beautifully updated 1-bedroom, 1-bath ocean view condo blends island charm with modern comfort, making it the ideal...
Beautiful, Updated Condo Across the Street from Famous Charley Young Beach
Hawaii Tax ID: TA-140-731-5968-01TMK: 390180030175This beautiful and updated condo is right across the street from the famous Charley Young beach, within walking distance of several other beaches along the Kihei coast as well as many shops,...
Oceanfront 2BR Condo w/ Pool Access & Sunset Views
This is a legally permitted vacation rental according to current County of Maui Ordinance.Private Oceanfront Escape – Sea Turtles, Snorkeling, and Stunning Sunsets E komo mai (welcome) to Mālama Honu, your luxurious home away from home at Hale Ono Loa 121. Nestled...
Chic 1-bedroom in beautiful oceanfront resort with King Bed and AC
Welcome to Kauai, Hawaii! We are delighted to welcome you to Outrigger Kauai Beach Resort, a hidden gem nestled on the sandy shore of an exclusive east-side oceanfront property. Our resort offers a blend of luxury, convenience, and affordability, providing a serene...
Wyndham Paniolo Greens | 2BR/2BA King Suite
Summary:This resort is a lush, tropical retreat in the heart of Hawaii's Big Island featuring spacious suites with private lanais. There’s plenty to do on-site, including a swimming pool, spa, tennis court, and scenic barbecue areas.This listing is for a 2BR/2BA suite...