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 Aloha: Luxe Waterfront Home, Island Vibe, Private Pool, Near Kailua Beach
Escape to Hale Aloha by Gather, a serene four-bedroom, two-bathroom waterfront retreat nestled at the end of a peaceful Kailua cul-de-sac. This 1,810-square-foot sanctuary sits on an expansive 12,000-square-foot lot, blending island charm, privacy, and modern comfort...
Papaouli Beach House
Maui Beach House is situated less than 50 yards from some of the most picturesque beaches. This two-bedroom, three-bathroom residence accommodates up to six guests. The master bedroom features an open-air design with a private lanai, a queen bed, and a jacuzzi. The main...
Ocean-view 2 BR condo with air-conditioners
Honokowai Palms is a friendly condominium vacation rentals with an outdoor pool. It is across the street from ocean and Honokowai Beach Park. Condo B1 at Honokowai Palms is an end 2-bedroom unit on the ground with a view of the ocean. Decorated in a family theme, this...
3 Bedroom Ocean View Private Home in Hana Permit#SUP2 2019/0006
SUP 2019/0006STHA20200001Hawaii TA Tax:TA-081-974-0672-01Hawaii GE Tax:GE-081-974-0672-01RThis is an Incredible opportunity to escape from the busy resorts and retreat to a private three acre estate with your loved one's, family, friends or solo. The Hana Nautilus...
KBV 17B3 Remodeled Kapalua Bay Villa w Ocean Views
Kapalua Bay Villas 17B3 Breathtaking Ocean Views at Remodeled 1Bedroom Kapalua Home for Winter Whale Watching. Has Central AC, Pools, Tennis Courts, and Close to PGA Golf Courses Escape to paradise at this 1-bedroom, 2-bathroom villa located at the prestigious Kapalua...
KRL H101 Remodel 2BD Condo Pool Kaanapali Beach Golf Whalers Village
Kaanapali Royal H101 Remodeled Spacious Ground Floor 2Bedroom Condo. Steps to the Pool and Close to Kaanapali Beach and Golf! Walk to Whalers Village, shopping, dining FREE daily activities included with your stay value up to $570! Complimentary admission, every day of...
Beautifully Updated, Private End Unit in a Gated Community
Come enjoy the big island in our tastefully decorated townhome. Don't book a hotel when you can book your vacation at our spacious villa and enjoy all of the extras we offer. It is conveniently located 18 miles north of the Kona International Airport in Waikoloa Beach...
Luxurious Ground Level Haven - Stunning Inside & Out - Makena Surf Resort C102
Makena Surf C102Experience unparalleled oceanfront living in Makena Surf C102, a luxurious ground-floor condo with spectacular views of Po'olenalena Beach. This 1,835-square-foot, two-bedroom, two-bathroom retreat is thoughtfully designed to provide the ultimate Maui...
Impeccable Penthouse - Ocean & Diamondhead Views
PANORAMIC OCEAN, DIAMOND HEAD & KAPOLANI PARK VIEWS. It's a première residential lifestyle ON THE GOLD COAST! A brief 15 minute breathtakingly beautiful walk to Waikiki’s famous beaches, shopping, dining and nightlife.This is not a tired old Waikiki hotel room with a...
Includes Beach Gear! Shores at Waikoloa 331
This vacation rental is professionally managed by ResorticaHawaiiShores at Waikoloa 331Please sPcroll down for detailed information Bedding Configuration:Master Bedroom: King BedLiving Room: Sleeper SofaAmenities:Beach Equipment: All of our vacation rentals include...
Luxury 3 Bed 2 bath apart Coffee Farm
Located on the mountain of Hualalai, retreat to this gated five acre farm. High above the heat of Kona coast but conveniently positioned near the airport, town and beaches. Arise from a tranquil night’s sleep to the song of the island’s delightful birds. Enjoy a cup of...
Large comfy house big enough for 2 families next to ocean on Kaloli point
Winter Months:January and February are the best times to see whales in the bay by the house. 2023 has been great, there have been many sightings of spouts (many are moms with their calf), tails and breaching. No specific time of day is best, so when you have the...
Kona Bali Kai 411, Oceanfront, Two bathroom
Welcome to Bali Kai 411, an oceanfront condo offering a peaceful retreat with panoramic views of the Pacific Ocean. Located on the beautiful Big Island of Hawaii, this spacious 2-bedroom, 2-bathroom unit is the ideal getaway for families, couples, or small groups...
Kuhio Shores 417, Oceanfront, Amazing Ocean View
Kuhio Shores is on the sunny South Shore of Poipu Beach and is small and quiet. It extends out into the ocean so that there is water on each side. Our condo has an expansive ocean view from wall-to-wall, floor-to-ceiling windows in the living room and dining room. The...
Nice Ocean View 1bed room, full kitchen, near Waikiki Beach! Rooftop pool&BBQ.
Our beautifully remodeled 1 bed room unit with a split ACs is located in the Pacific Monarch with a balcony and awesome ocean views! It's only a few steps away from the famous Waikiki Beach, shopping, and restaurants. The unit has a full kitchen with all kitchen...
Couples & Honeymooners. Privacy & Romance! 7 Sacred Pools
Ala Aina Ocean Vista is a unique, 100% solar-powered private ohana with front and back private entrances situated on a former banana plantation. Nestled in an exotic lush tropical setting, our accommodation promises peace and quiet and offers guests sweeping ocean...
Walk To All S Kihei Beaches, Shops and Restaurants-Pickleball
Aloha! E komo mai. We hope you will come and stay in our beautiful condo in Maui Vista located on the second floor in a quiet location of Building 2. We are facing the West Maui mountains so we do not get direct sunlight in the living room area of the condo. This make...
PENTHOUSE BEST VIEW Mauna Loa Shores the Ultimate Next to Beach Park
Wow. This is the finest unit in the Mauna Loa Shores. Fully renovated, with all the finest amenities and beautiful tastefully designed to maximize this fantastic condo. The best unobstructed view from the Bedroom overlooking the Blue Pacific, and the Lanai. You will...
Family Fun! Poolside, Pool Table, and Exclusive Hilton Pool Pass for '25
Experience the beauty and warmth of Hawaii at our spacious 3-bedroom townhome in the private, gated complex of Waikoloa Beach Villas, located on the stunning Kohala Coast of the Big Island. Our poolside unit is among the largest in the complex and boasts 1,872 sq. ft....
Maui Resort Rentals: Honua Kai Hokulani 615 - Upgraded 6th Floor Ocean View 2BR w/ Deluxe Corner Floor Plan
Widely regarded as the premier two bedroom floor plan at Honua Kai, this oversized two bedroom boasts a 1325 sq. ft. interior with direct ocean views from the kitchen, dining room, and living area, as well as the 315 sq. ft. wraparound lanai (balcony). The Hokulani...
Ahhhhh...... PARADISE. OCEAN VIEW, Beach Snorkel Surf
***NOTE: HAWAIIAN AIRLINES OFFERING 60,000 MILES WITH CREDIT CARD. ONLY NEED TO MAKE ANY PURCHASE TO ACTIVATE. HAPPY TO SHARE INFORMATION. BEST OFFER YET!!!!! HAD TO SHARE. Here is a link to the State website with information on travelling to Hawaii:...
Ocean Escape by AvantStay | Ocean Views | White Sandy Beaches | Brand New Home
Indulge in the Unmatched Beauty of Contemporary Luxury at Ocean Escape — A Brand-New Retreat!Discover the newly constructed, unparalleled, modern, luxury, three-bedroom house, where every corner is adorned with awe-inspiring ocean views. This Hawaiian haven transcends...
Waikiki Spacious One Bedroom Ocean View
Fabulous ocean view condo on Waikiki beach with one bedroom, one bath, a tiki bar lanai for watching the sunset & surfers, & a parking space. Large flat screen TV, free internet, secured residential building, salt water pool & spa, across Kalakaua Ave. from the beach....
Big Spacious Elevated View Home, Minutes to VNP, Myra's Blue Hawaii House
Support small business Owners. This property is managed and serviced by local entrepreneurs.Rent the entire home! Private,1300 sq. ft. 2 bed 2 bath home on the Big Island of Hawaii. Remote location yet minutes from amenities. Careful thought has been given to furnishing...
Island Surf with Ocean View - Across from popular Surf spot, Beach, and Shops
E komo mai! This is the Hawaiian way of saying all are welcome. Mahalo (thank you) for taking a moment to view my home in beautiful Kihei, Maui. This 4th floor condo is located in the most convenient location on Maui. From the moment you walk in the door it is...
❤️PiH❤️ HALE O'HONU ★ House of the Sea Turtle ★ KaMilo Detached Home
Brought to you by Paradise in Hawaii Luxury HomesWelcome to “Hale O'Honu,” House of the Sea Turtle, part of our Hawaiian Luxury Collection. Hale O'Honu is a brand new and beautiful 3 bedroom / 3 bathroom home that offers everything that you would ever desire on your Big...
Oceanfront Luxury / Kanaloa Kona Hawaii / 2 bed 2 bath + loft, sleeps 6
Please read NOTICE towards end of this description affecting November 18 - December 1, 2024.Kanaloa at Kona is an idyllic tropical oasis located on a point of land and surrounded by He'eia Bay, the Pacific Ocean and the Kona Country Club Ocean Course. It is rated by...
Lahaina Shores Beach Resort Studio
Elegant Hotel Suite with a full kitchen and beautiful top to bottom REMODEL. Enjoy all the amenities of this first-class resort hotel, Lahaina’s warm sunshine, and a beautiful white sand beach. Top-quality finishes throughout include; custom furniture, luxury memory...
Mahana 607-Oceanfront 1BR unit with Beautiful Views & Sunsets too!!!
Mahana 607 Completely remodeled 6th floor Condo with our guests in mind. As soon as enter Mahana 607, you will be mesmerized by the view. This unit offers: * Floor to ceiling windows with Oceanfront views. You can't get any closer without being on top of the water.* The...
Waikoloa Beach Golf Discounts! Waikoloa Beach Villas I2
This vacation rental is professionally managed by ResorticaHawaiiWaikoloa Beach Villas I2.Please scroll down for detailed informationBedding Configuration:Master Bedroom: King BedGuest Bedroom: Two Twin BedsAmenities:Beach Equipment: All of our vacation rentals include...
Gorgeous Oceanfront Retreat! Marvel at the Stunning Views from Sugar Beach #326
SUGAR BEACH RESORT, #326One Bedroom / One Bath Oceanfront CondominiumWelcome to Sugar Beach Resort #326, a beautiful one-bedroom condo with direct oceanfront views and updated interiors. Perfectly situated in North Kihei, this retreat combines comfort, modern upgrades,...
❤️PiH❤️ Paradise Found Villa ★ Bikes ★ Private Beach Club Pass ★ Near Pools
Brought to you by Paradise in Hawaii Luxury Homes.Welcome to Paradise Found Villa, a part of our Hawaiian Luxury Collection. Paradise Found Villa at Kulalani is a wonderful exquisite 2 bedroom home with excellent amenities. Located in Kulalani, it has golf course views...
White Sands Village #207 Lanai Ocean/MT Views Beach Access Pool Hot Tub
Almost oceanfront, well equipped condo conveniently located in White Sands Village on Alii Dr - just 4 miles from Kona Village Center- 2nd floor w/elevator access right outside the unit -sleeps up to 4 people with a king bed in the master bedroom and two twin beds or 1...
Perfect island getaway nestled near Sugar Beach
Welcome to Kanai A Nalu 215, a delightful 2-bedroom, 2-bathroom located on the 2nd floor, this beautiful unit features a private lanai with stunning ocean/pool views, split A/C throughout, and a private washer/dryer. There are elevators at this property for easy access....
Paradise Living at its Finest in this Gorgeous Condo
Welcome to C-108 at Papakea Resort—where comfort, style, and a touch of island charm come together to create the ultimate tropical getaway.A Space with Character & Comfort:From the moment you step inside, you’ll feel the difference. Our condo isn’t just another...
❤️ Stunning Reno| Amazing Ocean View 💦❤️
This is a TOP floor & Corner end unit with Vaulted ceilings. This condo has vaulted white washed with wood beam ceilings & gorgeous views of the ocean and tropical grounds as well as views to the beautiful West Maui Mountains! There is a bedroom, bathroom, and laundry...
Spring Special: 2BD Kapalua Golf Villa with Ocean Views
Escape to the heart of Kapalua and indulge in the beauty and tranquility of Kapalua Golf Villa 23P7 a fully renovated, 2-bedroom, 2-bathroom villa offering unforgettable Pacific Ocean and golf course views. Thoughtfully designed with upscale comfort and island-inspired...
Direct Oceanfront Condo. Kanaloa at Kona Resort. 3 pools. Central A/C.
SPECTACULAR UNOBSTRUCTED OCEAN VIEWS OF KONA COASTLINE & AMAZING SUNSETS FROM YOUR PRIVATE LANAI!Your vacation home features:* 1500 luxurious square feet.* Two spacious bedrooms with king beds.* Two full bathrooms with en suite primary bath. * Indoor and outdoor...
Includes Mauna Lani Beach Club Pass. Fairways at Mauna Lani 2001
This vacation rental is professionally managed by ResorticaHawaiiFairways at Mauna Lani 2001. Includes Mauna Lani Beach Club PassSteps away from the pool. Private end unitPlease scroll down for detailed informationBedding Configuration:Master Bedroom: King BedGuest...
Amazing View ~ Amazing Price ~ Amazing Location
Birds Eye View of Paradise... This Top Floor Condo offers: New Interior Furnishings ~ A Fully Equipped Kitchen ~ New Bedroom Furniture. There is a Community Pool, Hot Jacuzzi & 2 Gas BBQ Grills. This Gem is Nestled in the Heart of Princeville ~ Offering Views of...
Maui Kai 904 -Stocked King bed suite with AC & Stunning Views Sunrise to Sunset!
Welcome to our ninth-floor condo at the Maui Kai Resort in Kāʻanapali—where the ocean is so close, you’ll feel like you’re on the water! Enjoy breathtaking views of the Pacific, Molokai, and Lanai, with whales (in season) and sea turtles as your daily entertainment. Our...
Paradisio Ho'o Kumu – Luxury Kukui'ula Oceanfront Estate
A truly stunning oceanfront resort property offering six air-conditioned bedroom suites as well as pool, spa and access to Kukuiula beach park right across the street. Resort living at its best, this casually elegant, island-style private home offers ocean and coastline...
Luxurious 2-story sunset-facing villa on golf course - preferred end location
Waikoloa Fairway Villas J6Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Vacation in style at this beautiful Waikoloa Beach Resort condo! This is an open-concept, light and bright...
Live TOP Floor OceanFRONT. Relax & Sleep to Sounds of the Surf; AC or Tradewinds
Our fourth-floor, south shore condo is right ON the ocean so you have unobstructed views. You see "nothing but ocean" --and hear the sound of the surf-- as soon as you open your front door.This attractive, comfortable condo --with all the makings of "home"-- boasts a...
Poolside Paradise at Ko Olina: Elegance Spacious 2BR OT512 w/ Gym & Pool Access
Luxurious Condo - 2 bedroom(1king,2twin) + Pull out sofabed /2 bath 1parking Sleeps 6A luxurious room at Ko Olina Beach Villas. : Poolside location with easy access to the lagoon and resort amenities. - 5th floor of the Ocean Tower facing the pool and ocean .At 1,319...
15 Reasons Our Guests Never Want to Leave
When people stay at our Princeville Paradise, they don't want to leave. And we love that. I hear from them that they love the privacy and the open floor plan and that it has been completely remodeled. It has two bedrooms and two bathrooms, comfortably sleeps up to 6,...
Beautiful Ocean & Garden Views-Remodeled-Ac Throughout-Meticulous Cleaning
Book with confidence, this beautifully appointed Kamaole Sands, 1 bedroom, 2 bathroom (820 sq. ft) condo that has been remodeled. This condo is managed by PMI Maui, a local Real Estate Brokerage that specializes in vacation rentals. We are located within a mile of the...
Comfortable, Serene, ground floor, Steps from Best Maui Beaches!
Our Maui Beach Retreat is located in the pleasant Kihei Kai Nani condo complex. The unit is situated away from street noise, providing a nice quiet location. The lanai features a private tranquil tropical garden and is great for relaxing. It is a one bedroom condo with...
Mana Kai 412: Oceanview 2bd/2ba Condo Beach Access at Exclusive Kihei Resort
Mana Kai 412 with direct ocean views and beach access! Mana Kai is one of Kihei's most exclusive resorts, located right on Keawakapu Beach!This beautifully upgraded 2bd/2bath is perfect for families or couples traveling together. Enjoy gazing off at the magical Maui...
Beautiful 1BR/2BA ground floor unit, Kamaole Sands resort. 1 min walk to beach!
Come to Maui and stay in our beautiful Kamaole Sands property. This airy, open condo provides you with everything that you need for a comfortable and easy way to enjoy your Maui vacation. The unit is in a perfect ground floor location – across the street from the...