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.
Remodeled Oceanfront I Royal Mauian 509
Welcome to your perfect Maui getaway at Royal Mauian Unit 509! This beautifully designed, fully remodeled 1-bedroom, 1-bathroom oceanfront condo is located in the vibrant Kihei area, just steps from the stunning beaches and local attractions. Ideal for couples or solo...
3982 Kalakaua 4br 3ba Home in Princeville
Raise your vibes and take in the natural beauty and gorgeous architecture of this Island Style Home, built by a master carpenter. This spacious property is located in a peaceful cul-de-sac near Queen's Bath, Hanalei Bay, and the forthcoming world-class wellness resort...
Fairway Villa 120A: Charming w/ Shared Pool, AC, Golf Cart & Lanai Ocean Views
BREATHTAKING VIEWS - This corner VILLA features 2700 sq. ft. of interior living space and another 500 sq.ft. of covered lanai that boasts unhindered views of the 15th hole Jack Nicklaus Signature Golf Course and OCEAN. The villa comes with your own two golf carts to...
Wailea Beach Villas PH201 - 3 Bedroom Garden View Penthouse
Call this private piece of paradise home, which features panoramic views of Maui and the ocean below as well as luxurious interior elements everywhere you look. This contemporary vacation residence spans 2,500 square feet and captures the true allure of vacationing in...
Discover Paradise at Lagoon Tower by Hilton Grand Vacations – 2 Bedroom Oasis
Located within the iconic Hilton Hawaiian Village® Waikiki Beach Resort, the Lagoon Tower is your gateway to a vibrant tropical escape filled with unforgettable family fun, breathtaking views, and endless relaxation. Just steps from the legendary Waikiki Beach, this is...
Nalu Lani | Ocean Bluff Haven w/ Breathtaking View
Welcome to Nalu Lani, your “heavenly wave” retreat on Kauai’s breathtaking North Shore. Perched on the bluff at Sealodge in Princeville, this beautifully remodeled one-bedroom condo offers panoramic ocean views that will take your breath away. From your private...
Unique, Top of the Line Ocean View in Makaha
Locally owned and operated. Newly renovated with upcycled local accents and eco friendly products. All new premium wood cabinets combine with one of a kind solid cement coulter tops, stainless steel appliances, and mango wood shelving in the kitchen. A premium sofa...
Quiet get-away in Lush Tropical Setting- 5 min walk to snorkeling beach!
Experience spinner dolphins, sea turtles, hump-back whales (in winter), manta rays, amazing fish and coral reefs at pristine Kealakekua Bay, a protected marine sanctuary.Enjoy glorious sunsets through the palm fronds from the lanai or walk a few steps to the bay for...
Romance on top of the ocean-Amazing View-Large Lanai comfy daybed-Cold AC
Book Honu Hideaway today and fall in LOVE with this piece of PARADISE! You won't be sorry when you step into this one-of-a-kind, unique vacation rental sitting only 10 feet from the water's edge! 210 Welcomes you with so much ALOHA....Some of the many owner-supplied...
Fabulous Beachfront Property - Ground Floor Corner Unit Steps to the Beach!
This is the condo you've been waiting for! Location, location, location! Just steps away from a spectacular five mile stretch of white sandy beach, oceanfront heated saltwater pool, jacuzzi, indoor sauna and the inviting BBQ grill area.Recently updated with beautiful...
Kiahuna Plantation Resort 213 Ocean View 2 BD 2 BA
With breathtaking ocean views and a relaxed island feel, this two-bedroom condo offers plenty of space to unwind. Located near Kauai’s most beloved beach, it’s perfect for group getaways.Unit 213 Ocean View 2 Bedroom 2 Bath• Two-level condo in building 34 with...
NEW! Tropical Oceanfront Piece of Paradise, Every Room with Ocean Views and A/C!
NEW ON THE MARKET! QUIET and PEACEFUL on the edge of a bluff overlooking the Pacific. Soak up the unspoiled ocean air and magnificent breathtaking blue water horizon, ultimate beauty and peace. And from each room observe the most magical colors of sunset over ocean...
Ocean front 180° Ocean Views! Kapalua Bay Villa 22G2!! Quam Properties Hawaii
Experience the epitome of island luxury at Kapalua Bay Villa 22G2, a ground-level retreat offering sweeping 180° ocean views and effortless indoor-outdoor living. This spacious two-bedroom, three-bathroom villa welcomes you with an open floor plan and expansive lanais...
Oceanfront well-stocked home 20 ft from the ocean to relax and recharge
E komo mai! This beautiful Pikake unit is located in West Maui close to many amenities and beaches. We recently purchased this unit because of the many happy memories we have built with our family here. We hope you will create memorable experiences there as well!This...
Kauai Hale Luana Affordable 4BR Mountain View House
Beautiful two story 2,300 square foot vacation home with mountain views and cathedral ceilings. Hale Luana (house of relaxation) is a very comfortable and relaxing home located in Princeville on the North Shore of Kauai. (Maximum Occupancy is 8 guests and that factors...
Rainbow Inn. Pearl Harbor View. Great for a quiet get away or bring family.
House, 1 Bedroom + Convertible bed, kid zone with 2 twin beds, 1 Bath, (Sleeps 2-5) Double Occupancy Rate***** Private - Picturesque - Peaceful - Free WiFi - Free Parking, no resort fees!Panoramic views of Pearl Harbor, valley, ocean, and mountains with magnificent...
Maui Resort Rentals: The Whaler 1015 - Gorgeously Remodeled 10th Floor Interior Courtyard Studio, Spectacular Ocean and Mountain Views!
Boasting breathtaking ocean views in addition to lush vistas of the West Maui Mountains, this luxurious 10th-floor interior courtyard residence is one of the finest studio suites on offer at the acclaimed Whaler Resort. Its fully remodeled interior features several...
Nature Lover's Dream Hawai'i
Aloha and welcome to my precious gem of a home on the Big Island of Hawaii. Its 7 private acres have sweeping views of the ocean, sunset, and moonset and sits perched above the sacred Kealakekua Bay, where wild spinner dolphins love to frequent. Nature is vibrant and...
The Hula Moon Villa: Luxury Ocean View Penthouse - Best Value in Kolea!
OCEAN VIEW PENTHOUSE WITH DIRECT BEACH ACCESS!OUR HULA MOON VILLA IS LOCATED IN KOLEA, A PRESTIGIOUS BEACHFRONT COMMUNITY IN WAIKOLOA BEACH RESORT. Like a scene right out of a postcard, the luxurious Kolea resort is nestled on the shores of idyllic Anaeho’omalu Bay...
Polo Beach Club #602: 2 BR Condo with Stunning Views
Polo Beach #602Welcome to Polo Beach #602, a beautifully remodeled oceanfront condo located at the prestigious Polo Beach Club in Wailea. Perched on the sixth floor, this spacious two-bedroom, two-bathroom retreat offers stunning panoramic views of the Pacific Ocean and...
Remodeled 1 BR Garden View Maui Kamaole Condo - Short Walk to Beach
Our ground floor unit is located in the Melia "M" Cluster, and is among the newest and most private buildings in the Maui Kamaole complex. We extensively remodeled our condominium, including - new tile floors throughout; new tiled, walk-in showers; new cabinets/vanities...
Private Ocean View Cottage Overlooking Wailea
Couples find the privacy and space they dream of in our 1-bedroom ocean view cottage set on a hillside in sunny south Maui. Our cottage offers a fully equipped kitchen, living room, dining room and travertine bathroom. You car stays protected from the sun in your own...
M.Vista Bldg. 2-Immaculate Updated Quiet Classy- across from Charley Young Beach
Located in prime S. Kihei in highly desirable Maui Vista Bldg. #2 (Quiet, no traffic noise), up on 3rd floor (no car headlights). Directly across from famous Charley Young Beach. Condo is posh, remodeled a few yrs. ago with decorator paint, Granite counters, Rainfall...
Best Location! Beachy 3 BR Home, 4 miles to Ho'okipa, Permit #STPH2015/0006
Maui Permit STPH2015/0006 - 3 bedroom, 1 bath, legally permitted vacation rental (sleeps 2-5) fully equipped kitchen, FREE HIGH SPEED WIFI, stove/oven, dishwasher, coffee maker, toaster, blender, washer/dryer (for exclusive use by guests of this cottage, not shared with...
Rainbow Retreat
*MOLOKAI - NOT MAUI*Here at Rainbow Retreat, we take your comfort extremely seriously. From the Cozy Earth bamboo bedding (Oprah's favorite, 5 years running) to the quality furniture and design you will sink into and enjoy the quiet.Comfortable, minimalistic...
Kona Alii Condo with Ocean, Sunset, Mountain and Town Views
Located in the heart of Kailua Kona, this special retreat makes it easy to enjoy the day and night life of Kona town. With restaurants and shops within a few steps of the front door, it is also an ideal launching point for day trips to state and national parks, and the...
Large Island-Style Family Home with Wheelchair Accessibility
A beautiful 3 bedroom / 2 bath home, all on one floor, plus a sleeping loft; situated on the North Shore of Kaua'i in the town of Princeville. 2000 square feet living space plus a 200 sq. ft covered lanai. Ceiling fans are in all ground floor bedrooms, great room and...
Private tropical villa in Kona: Resort style heated pool, Hot tub & Ocean views
This lovely home sits on over half acre lot surrounded by palm trees, lush green lawns and tropical flowers with gorgeous views of the ocean. Resort style backyard with private pool with waterfall and a hot tub creates a relaxing oasis to enjoy at any time of the day or...
Private Pool | Central AC | Concierge Included | vrKCV
vrKCV - Holua Kai 11, Professionalyl Managed by Kona Coast VacationsCharming 3-Bedroom Home with Private Pool in Holua KaiExperience the essence of Hawaiiana charm and grace in this unique three-bedroom, plus bonus room, three-bathroom home, designed with open space...
Fully Renovated Condo located close to the beach!
Newly remodeled, and conveniently located, this 556 sq. ft. 1 bedroom, 1 bathroom condo villa offers privacy and modern comfort set in the heart of popular Kihei Town!This unit sleeps 2 guests on the comfortable king bed with built in wardrobe cabinetry and individual...
Beautiful Maui Beachfront Townhouse! Great Views! 200+ Five Star Reviews !!!
OUR MAUI BEACH HOUSE... (Please read our Guest Comments to see how great this place is!) This is the perfect place for a family vacation and retreat!! And it is right on the beach! Many of our guests enjoy staying right on our property or on our beach -- no need to...
Alihi Lani 4: Full A/C - top floor Ocean Views! Upgraded throughout
ALIHI LANI. This small, six unit complex called a 'Real Gem' by the Ultimate Kauai Guidebook. Enjoy endless views from our oceanfront pool. The front landscaped area also has two gas grills and comfy lawn furniture. We are named 'Premier Hosts' by VRBO and won the Trip...
Hale Milo: Charming Garden Cottage in Sunny Poipu!
Country-cottage charm meets elevated-plantation panache in Hale Milo: this delightfully distinctive 2+BR/2.5BA home in Kukui'ula’s leafy Kaulu neighborhood. Lovely island-style details and pleasant surprises abound, from the expansive lanai overlooking a lush,...
Makaha Shores Beach Front Ocean View Studio W/ AC
Makaha is a small town located on Oahu's West shore. 30 miles, 45 min from Honolulu Airport. The towns main attraction is its family friendly pristine and sandy beach. Makaha offers the best diving, snorkeling and surfing on the island. Our 5th floor gem beckons and...
Luxury + Privacy • Near Putting Green • Beach Club Access
Summary:Ka Milo in the Mauna Lani Resort • 5★ RatedKa Milo 228 is a luxurious 2-story townhome located in the highly desirable community of Ka Milo in the Mauna Lani Resort. With two master suites and two additional bedrooms, this townhome is perfect for a family...
❤️PiH❤️BEACH CLUB BLISS ★ Bikes and Beach Gear ★ Close to Pool ★
Brought to you by Paradise in Hawaii Luxury HomesWelcome to Beach Club Bliss, a part of our Hawaiian Luxury Collection. Beach Club Bliss at KaMilo is a wonderful single-level 3 bedroom home. We pride ourselves on providing some of the most sought after homes on the...
Maui Vista Complex, right across beautiful Charley Young Beach!
Locally owned and operated 🤙🏻Clean, private, updated, one-bedroom condo perfect for couples and families. Condo has additional queen size Murphy bed. Located in Kihei on the leeward, sunny side of Maui. Great for snorkeling, swimming and scuba diving; right across...
Oceanfront, beautiful, private property you have all to yourselves.
RENTAL has 2 OPTIONS between 1 & 2 bedrooms.QUOTE GENERATED BY THE SITE IS FOR 1 BEDROOM!Even if you rent just the main house, the detached master remains locked up. We wont rent to another group at the same time. If you are interested in both sides let me know and I...
AT THE SHORE ON ALIOMANU BAY-TVNC-1127
HALEKAI is privately owned by a Native Hawaiian family. We offer reasonably priced beach front accommodations. Our guests have exclusive use of the property assuring privacy.IMPORTANT! All coastal properties are exposed to the rare occurrence of a Tsunami, also known as...
Le'ale'a by AvantStay | Ocean + Mountain Views!
Le'ale'a — that sunny, blissful feeling of wonder and joy you only feel when immersed in the beauty of a place like the Hawaiian islands. And there’s plenty of it here! In the heart of Mākaha Valley and surrounded by stunning tropical mountains, this bright...
Sunset in Paradise Oceanfront 1BR/1BA Condo at Kona Reef Fast WiFi & Central AC
Note: Kona Reef will be undergoing necessary exterior repairs on neighboring buildings January - June 2026. Repairs to the parking areas will take place April 2026 - April 2027. This may result in additional noise 8-5 on weekdays as repairs are completed. Rates are...
Breathtaking Kona Home - Heated Pool / Air conditioning and Beautiful Sunsets
This breathtaking 3 Bedroom plus bunkroom, 2 bath single level home is located just minutes from Kailua, Kona and some of the most beautiful beaches in Hawaii. Everything in this house is new! Fresh full remodel just completed. This includes a brand new gourmet kitchen,...
Best Ocean Views at Kihei Kai Nani #206nSteps to the beach 1 Bdrm / 1 Bath
Looking for the best view at Kihei Kai Nani? It is unit #206! This updated, corner penthouse boasts stunning beach and ocean views from the living room and lanai (patio). Relax to the sounds of the ocean and enjoy sunset views every night from the lanai or living room....
Honolulu Condo Stay w/ Balcony: Walk to Beaches!
Embark on your next island adventure and stay at this Honolulu vacation rental located in the Chateau Waikiki community! When you stay at this 1-bedroom, 1-bath condo, you’ll have access to community amenities like outdoor pools, a game room, a fitness center, and...
Cycle or Walk to Hanalei Bay
Totally remodeled, updated - all new furniture, fixtures, finishes.TVNC - 5119This vacation rental is located in Hanalei which is in the tsunami evacuation zone. The house is in the quintessential beach town of Hanalei. Walk to the bay for a surf, swim or beach walk....
Best location at Kuleana (Unit 405)! New Remodel. Spectacular Oceanviews.
Welcome to your island escape at the Kuleana Resort, West Maui’s hidden gem. This newly remodeled oceanfront 1-bedroom, 1-bath condo offers the perfect blend of comfort, style, and location—just steps from the shoreline, heated pool, and resort amenities.Enjoy...
4 BR Kahala Vacation Home with Pool & Spa, Near Kahala Beach
This Property is professionally managed by Private Homes Hawaii, and is a legally established rental accommodation that is rented for periods of 30 consecutive days or more at any one time. It is compliant with Hawaii State Legislation (HB2078). Lic#TA-008-741-5296-01....
Newly Renovated Condo with SUP Paddle Boards and Golf Clubs Included
Newly renovated luxury short term vacation rental for up to 29 nights 2 bedroom, 2 bathroom en suit condo inthe greater Keauhou Resort area. Quiet Concrete Building! No Paper-Thin Walls Here, Folks!Located on the 8th fairway, our beautiful condo is situated in the...
Calming Volcano Studio 2 Blocks From The Ocean
This comfy and clean Volcano Studio is located 2 blocks from the beach and Ali'i drive where all the best attractions are such as tasty restaurants, fun retail shops, bars, coffee and smoothie spots, fresh farmers markets, Magic Sands Beach, and much more. The Volcano...
Thoughtfully Remodeled 3 Bedroom Townhouse North Shore Hale 6B
E Komo Mai (welcome!) to "The Cozy Aloha", a lovely 3-bedroom townhome oasis in the peaceful north shore community of Hale Honu in Princeville. This newly renovated 1,148 sq ft split-level condo seamlessly blends modern comfort with tropical charm.Step inside to...