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.
Includes Mauna Lani Beach Club Pass. 801 Kulalani
Kulalani 801. Includes Mauna Lani Beach Club Pass Please scroll down for detailed informationAloha!We’re excited to share that you this property is being beautifully updated with brand-new Restoration Hardware furnishings and refreshed interiors. The remodel is designed...
Bright Condo w/ views of the Ocean & shared pool/hot tub - close to golf & beach
Making Makahuena Memories in 2204Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Welcome to Makahuena at Poipu Unit #2204, a gorgeous second-floor condo in Koloa, Hawai‘i, where...
Kona Sea Ridge#Y22: Beautiful Top Floor unit with Ocean Views in Gated area
.Oceanview Paradise | Top-Floor 2BR/2BA Kona Sea Ridge Condo | Kailua-Kona, HawaiiWelcome to your slice of paradise at Kona Sea Ridge! This top-floor, two-bedroom, two-bath condominium offers beautiful ocean views and the perfect blend of island comfort and modern...
Walk to Dtwn Hilo: Island Escape w/ Pool!
5 Blocks to Bayfront & Beach | 1 Mi to Rainbow FallsPack up for paradise, where relaxation and adventure blend seamlessly. This 2-bedroom, 1-bath Hilo vacation rental places you within just 1 mile of hot spots like the lively Hilo Farmers Market and the breathtaking...
Beach, City lights and Mountain Views 180 degrees view & centrally located
Discover this charming 3-bedroom gem in Honolulu. This excellent condo features 1 king bed, 1 queen bed, 2 full beds and another queen queen blow up bed that can be use in the living room, perfect for a group getaway. With 2 bathrooms equipped with hair dryers and...
Puna Rainforest Retreat Hotspring - Purple Passion Cottage
The Purple Passion Cottage is located on a serene 20 acre estate with beautiful ocean and meadow views. The cottage is cozy and equipped kitchenette (range, oven, mini-fridge/freezer, microwave), full bathroom and two bedrooms. The main bedroom has a king bed with an...
NEW! Volcano Tea House Cottage 2-HotTub-FirePlace
NEW LISTING 6/2025! Welcome to The Volcano Tea House Cottage 2, located just 6 minutes from Hawaii Volcanoes National Park. The original Tea House was established in 2014, and it inspired us to build and design another Tea House in the same neighborhood. The home has...
Puna Rainforest Retreat Hotspring - Blue Ginger Cottage
Puna Rainforest Retreat Blue Ginger Cottage has a complete kitchen with all the amenities, a full bathroom and cozy queen size bed. Perfect for couples. This colorful cottage is clean, comfortable and affordable! Enjoy the rainforest trail, steam vents, plunge pool,...
Maui Resort Rentals: The Whaler 1001 - Upgraded 10th Floor Oceanfront Corner 1BR/2BA - Premier 1BR Location at The Whaler!
Maui Resort Rentals is proud to present this stunning 1BR oceanfront residence at the iconic Whaler Resort on Kaanapali Beach—newly launched and available for bookings starting July 5th, 2025!Situated in one of the most coveted locations at The Whaler Resort on...
09 FREE Parking/10 min beach/2br-Waikiki/Ala Moana
Legal Vacation Rental!! Newly renovated! Excellent location! Central to Ala Moana Shopping Center, Waikiki attractions, beaches, restaurants, bars, zoo, business district; on bus line, easy commute to Downtown,Chinatown,UH. Secured building: security guard, 24-hr...
MHL 66 3BD Condo Across from Keawakapu Beach & Ste
Maui Hill 66 NEW LISTING Experience Maui from this Amazing South Kihei Location, Walk to the Beach, Minutes to Wailea! FREE daily activities included with your stay value up to $956! Complimentary admission, every day of your stay*: Lu'au, Golf, Whale Watching...
koolkondo 2597 Halalu Guest house
Welcome to your dream escape in Poipu Beach Estates! This beautifully upgraded one bedroom guest house is tucked away in a serene, palm-fringed setting that offers ultimate privacy and space to unwind in paradise.The Guest house features one king bed and one queen sofa...
Liko Lehua Cottage in Volcano - Hot Tub & Fireplace - Mauna Loa Estates
Liko Lehua Cottage - Your Hawaiian Forest Retreat!Escape to the enchanting Liko Lehua Cottage, a hidden gem just six minutes from the awe-inspiring Hawaii Volcanoes National Park. Nestled in the lush, serene Hapu'u forest of Mauna Loa Estates, this newly reimagined...
Hale Maia at Kukui ula - Elegant Pool Retreat with Golf Views in Poipu
Summary:TA-101-738-2400-01Discover Hale Maia at Kukuiula, a stylish and spacious 5BR, 5.5BA home in Kauai’s most exclusive community. This modern retreat features panoramic fairway views, a private heated pool, and seamless indoor-outdoor living. With each bedroom...
Hale Nani at Kukui'ula - Luxe Family Hideaway with Poolside Living in Poipu
Summary:TA-101-738-2400-01Hale Nani at Kukuiula is a contemporary 5BR, 5.5BA residence offering a peaceful escape in one of Kauai’s most prestigious neighborhoods. With golf course vistas, a private heated pool, and open-air living spaces, this home invites relaxation...
Plantation Hale Suites J1, AC, Walk to town, Near Beaches, Wifi
Welcome to Plantation Hale Suites Unit J1 on the beautiful island of Kauai! This unit is a ground floor, end unit.Experience the best of Kauai at our Kapaa vacation rental, centrally located on the Royal Coconut Coast in Wailua. Whether you're here for relaxation or...
🌺 Oceanfront Resort Napili Shores ~ Majestic Maui Paradise ~ AC ~ Napili Bay! 🌴
Aloha & Welcome to Napili Shores C215, your second-floor corner unit, steps from pristine, sandy Napili Bay! Amazing hotel-zoned resort amenities - 2 heated swimming pools, hot tub, BBQs, lush tropical gardens, shuffleboard, the famous Gazebo restaurant, Kitchen 5315 &...
New Listing! Hotel Zone Lahaina Shores Premier Mtn view Studio on the Beach
New Listing Call 1 707 477 8952 if you have questionsLahaina Shores Mountain View Studio an Ocean front property on Front St. LahainaLahaina Shores Beach Resort Hotel Zone property 475 Front Street, Lahaina, HI 96761Mountain View studio maximum guests 2Ocean Front...
New Remodeled May 2025 1-bed.Apartment in Kiahuna with AC and fiber internet.
Located in Koloa, enjoy what this 1-bedroom apartment has to offer. Guests can take advantage of the fitness room, iron, hair dryer, AC, heating, and WiFi during their stay. The cozy bedroom provides a nice retreat after a day of exploring. Make your holiday one for the...
Big Island Luxury - 3000+ SqFt. 4 Bed 4 Bath. Beach Close. Hawaiian Paradise.
Our Newly Renovated Estate Home in the quiet neighborhood of Hakalau invites our guest to relax and enjoy paradise in luxury. Spacious and open floor plan offers plenty of room to accommodate large groups and gatherings. Air conditioned living spaces and bedrooms. Free...
Golf Discounts at Waikoloa Beach Resort Courses for 2025. N34 Fairway Villas at
Waikoloa Fairway Villas N34Please scroll down for detailed information Bedding Configuration:Main Bedroom: King BedGuest Bedroom : Two Twin BedsLoft: Queen BedWaikoloa Beach Resort Gold Membership Golf benefits (discounted tee fees at the Waikoloa Beach Resort Courses)...
Princeville Resort Residence ~ Honoiki Hale Hou ~ On the Makai Golf Course
Princeville, above Hanalei Bay ~ Stay Luxuriously on the Makai Golf Club Course 2nd fairway.~ Rated "Best In Resort" Location and Condition!Our action packed community surrounds itself a Bluff above the Bay and Ocean with stunning views everywhere.You will LOVE our...
NEW LISTING!! Kapalua Ridge Villa #1722 with views that are simply spectacular!
With views that you thought were only made for dreams, this villa will surely take your breath away. Located in the world-class Kapalua Resort, the vistas this unit has to offer are truly jaw dropping. Your windows are filled with a panorama composed of the sparkling...
Kona Plaza 301, Ocean Views and Renovated
Kona Plaza 301! Your Ideal Hawaiian Getaway! Welcome to Kona Plaza 301, where modern comfort meets tropical paradise! This beautifully updated condo features brand new floors and is designed to provide you with a relaxing retreat during your stay in the heart of...
Best Window seats to Ocean Views- in wonderful Ocean View HI with WiFi
If you love Hawaii, then this place is for you. The Guest house has magical views of South-point beach with panoramic views from the oversized window seats. South-point is the southernmost tip in the United States and a national historic landmark! Shore fishing, tide...
New Listing! Peaceful island living with a view
Welcome to Kaanapali Shores Unit 733! This comfortable 1-bedroom, 1-bath condo is located on the 7th floor and can easily accommodate up to 4 guests. Stay cool with central air conditioning or step out onto your private lanai to enjoy the ocean breeze and relaxing views...
Kona Coast, BEST Oceanview&Pool, Yoga/Meditation Space, Pickle Ball&Basket Ball
Welcome to Halani — Your Serene Sanctuary on the Big IslandEscape the busyness and crowds of the resort scene and discover Halani, meaning “heavenly breath”—a peaceful retreat perched above the South Kona coast, offering one of the most unparalleled ocean views on the...
4 Star Beachfront Resort. King Bed. Lanai. AC. Restaurant. Pool. Gym. Spa.
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...
Rare Penthouse Ocean View Unit 3bd/2bth Upgraded
Welcome to one of Kihei's best-kept secrets- a top-floor, corner-unit penthouse at Kamaole Beach Royale, now available.3Bd/2Bth luxury condo offers unmatched privacy, panoramic ocean views, and exclusive developer upgrades. Perched on the 6th floor, this spacious...
New Listing! Luxurious 4BR/3BA House with AC
Discover Elegance at Poipu: The Leilani House hosted by BlueTideVillasWelcome to The Leilani House, a beautifully designed 2,100-square-foot retreat set on a private half-acre just minutes from Poipu Beach and local dining. Celebrated as one of Poipu’s most desirable...
Wailea Elua 808 - Scenic Ocean Views, Classic Wailea Charm, Central AC, Wi-Fi
Welcome to Wailea Elua 808, your ideal Maui retreat. This spacious 2-bedroom, 2-bath condo offers the perfect setting for a relaxing getaway or a family vacation. With a thoughtfully designed floor plan, stylish furnishings, and ample natural light, you'll feel at home...
Jungle Retreat in Kona Cloud Forest Sanctuary, An unforgettable Cloud Forest Sanctuary retreat exper
Wake up in your cozy private jungle retreat immersed in the lush serenity of the Kona Cloud Forest Sanctuary. During your stay in our Sanctuary, experience our guided forest tours, yoga, sound baths, and more. Enjoy a morning walk for fresh brew and coffee tours at...
Pili Mai 06L By Parrish Kauai
Nestled among a championship golf course, Pili Mai is set in an ideal location on the island of Kauai’s south shore in Poipu Beach. This is Kauai's newest resort development and has a choice of two, three, and four bedroom luxury condominiums.This central Poipu location...
Kaanapali Shores 435 By Parrish Maui
Kaanapali Shores offers the best of oceanfront resort living on Maui’s renowned West Side. Each spacious vacation rental includes a full kitchen, private lanai, and thoughtfully designed interiors that blend comfort with island style. Guests enjoy access to two swimming...
Surf, Sand & Serenity- Kihei Akahi D213 Ocean View
Aloha and Welcome to Your Maui Escape at Kihei Akahi D213!We're new owners and offering great prices. Discover your perfect island getaway at our beautifully updated one-bedroom, one-bathroom condo in the heart of South Kihei. Just steps from Kamaole Beach Park II and...
Kauai Oasis - Luxury 6 BR Kukui'ula Estate with Infinity Pool
Magnificent, spectacular, and amazing describe Kauai Oasis, a brand-new 2024 Kukuiʻula retreat. This luxurious home offers sweeping views of the ocean, Kukuiʻula golf course, Hđupu mountains, sunrise, and full moonrise. Watch the Milky Way and meteor showers from the...
Tropical Bamboo Retreat in Upcountry Maui!nBamboo Heaven Maui LLCnBBPH 2012/0003
Consider this bed & breakfast your home away from home while you visit Haiku Maui! This tropical property offers a peaceful retreat in the country with fruit trees, rainbows, and night skies filled with stars and galaxies! My unique bamboo home welcomes you to unwind...
Private KÅloa Retreat | Pool + Golf Course Views | Near PoÊ»ipÅ« Beach
Discover this lovely 3-bedroom gem in Kōloa. This awesome house features two king beds and two queen beds perfect for families or friends looking for a relaxing island retreat. With three full bathrooms including walk-in showers, a soaking tub in the master suite, and a...
Kona Koa House by Gather: Oceanview 3BR Estate w/ Heated Pool & BBQ
Escape to Kona Koa House by Gather, a stunning 3-bedroom plus bonus room, 3-bath vacation home set within the prestigious Keauhou Estates gated community in Kailua Kona, Hawai‘i. Perched 500 feet above sea level, this luxurious single-level retreat spans nearly 3,000...
Hale Kai - Brand New Kukui'ula Luxury Home with Pool & Spa
Nestled in the exclusive Kukui'ula neighborhood in Poipu, this stunning, brand new luxury home offers the perfect blend of comfort, elegance, and island charm. With 4 bedrooms and 4.5 bathrooms, this meticulously designed residence comfortably accommodates up to 10...
Ohia Lehua Hale-Hot Tub-Fireplace-Fire Table-3-Bed, 2-Bath Newly Renovated Home
Welcome to Ohia Lehua Hale, located just 6 minutes from Hawaii Volcanoes National Park. Escape to our recently renovated vacation home; we recently added many upgrades to enjoy a relaxing stay.*New Built-in Gas Fireplace *New Smart TV*New Outdoor Hot Tub *New Outdoor...
Cozy ground floor condo, lush lanai, dining nearby
Welcome to Maui Kamaole F101 – your perfect island retreat! This beautifully appointed ground-floor condo features 1 bedroom and 2 full bathrooms, comfortably accommodating up to 4 guests. The dual-bathroom layout is ideal for families or couples traveling together. The...
Streaming with Sunlight 2+2 Hawaiian Villa
2 bedroom, 2 bath Villa with ocean views nestled in picturesque Kona Coffee Villas. Higher elevations, and mountainside complex presents an ideal setting for your Hawaiian Life Style. After a day at the beach, sink into one of two comfortable sofas in the living room...
Maui Kamaole #C-203 - Remodeled Upstairs Retreat with AC and Resort Pools!
Maui Kamaole #C-203Maui Kamaole #C-203 is a beautifully remodeled two-bedroom, two-bathroom upstairs unit offering a peaceful setting, modern comfort, and a fantastic location near some of South Kihei’s best beaches. This updated condo features island-inspired décor,...
Relaxed Suite Near Shipwreck Beach + Parking & Pool Access + Kitchen
Experience oceanfront serenity with stunning views, spacious rooms, full kitchen, private balcony, and in-room laundry—ideal for couples and families. Snorkel nearby, hike the Mahaulepu Trail, or spot turtles at Poipu Beach. Relax in our large outdoor pool. Whether you...
View of Mauna Kea in Gated Community across from Golf Course
Quiet & Private 1 King bed/1 Twin daybed/1 bath kitchenette (attached to main house) w/ separate entrance & patio ~600 sqft in secluded & gated community at a cool 2400 ft elevation. Wake up to beautiful views of Mauna Kea. Located 30 min by car from Kona Airport,...
KÄÊ»anapali Ocean View Condo with Beachfront Cabana for Guests
This charming studio places you in the heart of KÄÊ»anapali, one of Maui's most iconic destinations. Enjoy ocean and golf course views from your private lanai and inside you'll find a fully equipped kitchen, A/C, king bed, and Wi-Fi for a comfortable stay. Guests have...