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.
NEWEST! California Coastal Inspired in Maui 2 BR
Located in the heart of Kaanapali, this spacious, newly remodeled, 1,440 square foot, ground floor, 2-bedroom condo is ideal for one or two couples, or a family of 6 looking for a relaxing getaway! This condo is ideally located in the heart of the Maui Eldorado, steps...
New to VRBO. Air Conditioned Luxury Island Retreat - Newly Remodeled
Newly remodeled ground-floor condo at Alii Kai with all new fixtures and furnishings.Located on the cliffs above Turtle Cave, you are just steps away from a private path leading to snorkeling with Kauai's magnificent Sea Turtles. Enjoy ocean views from the front porch...
Mele Nani Getaway in lovely Volcano, Hawaii
Mele Nani in Volcano, Hawaii is our sweet two bedroom, one full bathroom vacation home. Our favorite spot is the hanging lounger on the covered, front lanai. Gently rock to the bird song all around while sipping your morning coffee. We offer a small wood burning...
Island Style Elegance on a Beach Access
Island style elegance with beach access.Immerse yourself in the island inspired luxury of Portlock Paradise. Sitting on large lush ocean access property, Portlock Paradise offers four bedrooms, 3 with ensuite bathrooms, an indoor and outdoor dining areas, elegant...
Breathtaking Ocean View Condo w/ new furnishings - Poipu Kapili #30
Amidst the luxurious oceanfront Poipu Kapili Resort, is an exquisite 1 bedroom, 2 bath remodeled single level, second floor holiday home endeared as Poipu Kapili 30. Perfectly manicured lawns, immense palm trees along with fragrant and vibrant blossoms promise a...
free parking - walk to Honl beach & Downtown Kona
BLUE BEACH BUNGALOW is your personal oasis in the heart of the most desirable place in Hawai'i. Perfect for everyone to enjoy the Aloha spirit and explore what the Big Island of Hawai'i has to offer. Pull into your private driveway where you are transported into a...
Hale Kahili Nui – Poipu Beach Estates Luxury Villa
For those desiring larger accommodations, Hale Kahili Nui able to be combined with Hale Kahili Ohana for a Hale Kahili 8 Bedroom Estate experience.Amazingly spacious and extraordinarily appealing, this newly constructed 2-story villa is conveniently located in Poipu...
Luxurious home on resort grounds with lanai, grill, pools, hot tub - near beach
Mauna Lani Maluhia #420Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Luxury plus paradise equals this gorgeous home, tucked onto lush grounds at the KaMilo at Mauna Lani resort...
High Floor Luxury Oceanfront @ Waikiki Beach Tower
Waikiki Beach Tower Relax in this exclusive upper floor unit at the most luxurious vacation rental tower on the beach in Waikiki. This 1,200 SF newly renovated condo has the only open floor plan in the entire building and its sky high location on an upper floor provides...
Upgraded ground floor condo with beach access
E Komo Mai “welcome” to Hale Mahina B105! Hale Mahina B105 is a ground floor, one bedroom, one-bathroom condo that sleeps 4 guests. Although this unit does not offer air conditioning, stay cool inside with ceiling fans throughout! The entire unit boasts new, beautiful...
Enjoy sunsets-Beautiful Oceanview Pac Shores perfect for couples and families!
Start your mornings on the third-floor lanai for sunrise and end the day at Charley Young beach for spectacular sunsets. Watch turtles cruising the waves and spot whales offshore during the winter season.Two bedrooms and two bathrooms provide space and privacy for...
Palms at Wailea 1203 Offers The Perfect Location in Wailea!
Palms at Wailea 1203, offers the perfect location in Wailea. This 2-bedroom/2-bath ground-level unit surrounded by lush landscaping makes this a great Hawaiian retreat!Ideally situated just uphill from gorgeous Keawekapu Beach, The Palms at Wailea is an...
Newest Unit * Modern Coastal Luxury Meets Maui *
Welcome to Maui Eldorado H105, a completely remodeled and beautifully reimagined one-bedroom suite in the heart of the Kaanapali Beach Resort area. Blending elevated California coastal design with relaxed island living, this thoughtfully curated retreat is perfect for a...
Wavecrest Resort Condo on Molokai
Wavecrest C109Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Find your island zen at this Wavecrest Resort condo. Just a short drive from the main part of town, this tropical...
180° Ocean views • Luxe condo • Steps to Beach
Enjoy panoramic ocean & sunset views year round from, Kihei Lani, a 5th floor luxury condo that artfully blends contemporary design, modern amenities and island style. Full, whisper quiet AC in all rooms! Ideally located in Kihei, the condo is right across the street...
Perch - Maui Sunset: One Bedroom Suite, Part Ocean View with Big Lanai
Island Vacation at its finest! This partial ocean view condo is designed for comfort. Partial Ocean view, the unit has been nicely designed and features tile flooring, granite kitchen counters, stainless steel appliances and more. A large lanai Ideal for taking in that...
Chic cottage in Rainforest 5 Min. to Volcanoes Park-clean, cozy, comfort -2 Bdrm
NATIONAL PARK OPEN FREE ADMISSION ,Limited Ranger Services. Discover a serene artistic haven just 5 minutes from Hawaii Volcanoes National Park and village restaurants, an ideal launchpad for exploring the East Side of the island. ,Enjoy rainforest ambiance from our...
Princeville Palms Manor - Hanalei Bay
Locally-crafted Décor, Spacious Chambers, with Natural Wood Trim. Beautiful Two-Story Air-Conditioned Retreat …serenaded in the song of jungle birds!Meticulously thought-out kitchen, accessories, games and endless amenities. For our eco-conscious guests, we've installed...
❤️PiH❤️ Peaceful Paradise ★ Private Pool and Spa ★ Bikes
Brought to you by Paradise in Hawaii Luxury Homes.Welcome to the newest elegant home, Peaceful Paradise, in our Hawaiian Luxury Collection. Peaceful Paradise is a wonderful new large single level 3 bedroom, 2 bathroom home. This home is an amazing family retreat in the...
Hale Hahalua - Serenity and Ocean Views in Kona now with upgraded A/C in bedr.
Aloha! Welcome to Hale Hāhālua – the gateway for your dream vacation on the Big Island of Hawai’i. Located in the picturesque community of Keauhou (Kailua-Kona), right above Keauhou Bay, our condo offers you the perfect starting point for your adventures. In Hawaiian,...
Mokulua Sunrise Ocean Villa Lanikai
Experience the ultimate Hawaiian escape at Mokulua Sunrise, a stunning 4-bedroom, 3.5-bath oceanfront villa nestled in the world-famous Lanikai neighborhood of Kailua, Oahu. With sweeping, unobstructed views of the turquoise Pacific and the Mokulua Islands, this...
Resort View - 2 Bedroom - Westin Nanea Ocean Villas - Full Resort Access
Enjoy a luxurious stay for a fraction of the cost. Typical savings range from 30-70% when comparing our rates to direct resort bookings. All of our units are managed and maintained by the resort. Upon arrival, guests will check-in at the resort’s front desk using their...
Stunning Deluxe Ocean View W/Lanai-Kamaole Sands
Kamaole Sands unit #10208 is located on the second floor: With all the space, comfort, and amenities necessary to accommodate an unforgettable Maui retreat, there is no place better than this recently remodeled one-bedroom/two-bathroom condo located within a block from...
Remodeled Condo W/Ocean Views-Kamaole Sands 10301
Kamaole Sands unit #10301 on the third-floor: Plush new furnishings enhance the living room, with a brand new flat screen TV and a pull-out sofa couch for additional comfort. Sliding glass doors open from the living room to a fully furnished lanai, where you can enjoy...
Wai'ula'ula C102 - Magnificent Ground-Level Residence
This magnificent, corner, ground-level, oceanview residence offers a great room with sliding glass pocket doors for indoor/outdoor island living, a chefs' kitchen outfitted with stainless steel appliances and granite countertops, plus a dining area for six. Additional...
Alii Cove C-4 Beautiful Beachy Townhome on Alii Drive
Experience the allure of the Alii Cove C-4 Town-home, where exquisite decor meets cozy comfort, perfect for entertaining large gatherings while radiating that charming beach house vibe. The expansive Primary suite exudes glamour and luxury, featuring sumptuous bedding...
Aloha Condos, Napili Bay Resort, Condo 110, Beach View
*******REMODELED******* Best Beach View Location! This is Hawaii the way you dream about it. No building taller than a tree on Napili Bay. Swim, surf, boogie board, stand up paddle, snorkel, seasonal whale watching and glorious sunsets without leaving the property.30...
Amazing Ocean Views Private Pool and Spa
Our breezy Cottage with 180 degree ocean views and private pool and spa sits at a cool elevation about 10 minutes from Kailua Kona. The home is located on the Walua walking trail and minutes from snorkeling, shopping, and dining. PLEASE NOTE: The property is in the...
Luxury Resort 🌴 Ocean View 🌊 Golf Membership ⛳
Summary:Hali’i Kai in Waikoloa Beach Resort • 69-1033 Nawahine Place #10A • 5★ RatedHali’i Kai 10A is a stunning oceanfront condominium in the highly sought-after gated Waikoloa Beach Resort. This family-friendly 2-bedroom, 2-bathroom unit comfortably accommodates up to...
Luxury + Privacy ✨ Ocean View 🌊 Sleeps 10 🛌 Beach Club Access 🏖️
Summary:Ka Milo in the Mauna Lani Resort • 5★ RatedKa Milo 425 is a 2-story luxurious 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 or a...
Luxury + Privacy ✨ Sleeps 10 ⛳🚙 Golf Cart Included
Summary:Ka Milo in the Mauna Lani Resort • 5★ RatedKa Milo 119 is a luxurious 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 or a group...
Privacy + Luxury ✨ Oceanfront 🌊 Panoramic View 🌅
Summary:Hali’i Kai in Waikoloa Beach Resort • 69-1033 Nawahine Place #13D • 5★ RatedHali’i Kai 13D is a Kohala Coast oceanfront corner villa located in the highly desirable gated property situated in Waikoloa Beach Resort. This upgraded villa boasts 2 spacious bedrooms...
Spectacular, Oceanfront 3 bedroom + den, AC, pool, sleeps 7.
Puamana 160-2 offers a spectacular opportunity to enjoy oceanfront living at its best. Relax on your spacious lanai just 40 feet from the water’s edge, grilling, dining, and watching the ever-changing ocean vistas, surfers dancing on the waves, whales in season,...
WHALE'S TAIL -Beachfront in Magical Puako! Ocean playground outside the door!
Combine the sandy beach next to your back yard with the thoughtfully placed windows that give you excellent views from nearly every spot in the house—upstairs and down—and you’ll love the Whale’s Tail for your Hawaii vacation. Not only is the entire ocean-facing wall...
BIG ISLAND OHANA HALE- Beautiful Oceanfront Home in Puako, Stunning Sunsets!
Walking into this home, the first thing that greets you is the sight of the sea. The house is directly behind a short seawall with views from virtually every room. The designer-furnished home is two-stories with three oceanfront bedrooms, two on the ground floor and one...
BIG ISLAND HALE MELE MELE, Lovely Cottage in Magical Puako!
NOW ALL BEDROOMS HAVE AIR CONDITIONING TO GO ALONG WITH AC IN THE LIVING ROOMStay cool everywhere in the home!Hale Mele Mele is one of Puako’s original beach cottages lovingly restored, refreshed and redecorated to feel like home-away-from-home. The fully-equipped...
BIG ISLAND HALE OHANA, 4 BR Oceanfront in Puako, Private Pool! Spring Rates!
This 2200 square foot home was built in 2002 with an additional bedroom and bathroom added in 2012. It was designed in old Hawaii estate style with a roomy 1100 square feet of lanai, screens and sliders that open full length plus louvered windows to encourage the...
Kauai Exclusive - Pili Mai 7E - Three Bedroom Suite - AC, Pool & Fitness Center
Pili Mai 7E is a three-bedroom, two-level suite with plantation-style architecture. Newly furnished and decked with bamboo floors, Koa cabinets, a gourmet kitchen and central A/C, this villa is a fresh find. Revel in all the bells and whistles of a new tropical vacation...
Best and Newest Beachfront Listing in Honolulu
LAST BLOCK of time for the year just discounted! December is heavily discounted, spend the holidays in paradise! Inquire for details. This is a completely modern, sandy beachfront villa in a private and secluded location in Honolulu that is the perfect home and location...
Luxurious Blue Horizon Villa near Hilo, entire villa
Welcome to the Blue Horizon. Our luxurious, modern villa with hot tub by the cliff is a perfect place for a family vacation for up to 6 people, 2 story approx 2300sf + 1000sf of view lanais. Downstairs has 2 bedrooms with king beds and 2 bath. Upstairs has a very open...
KaMilo Luxury Living - Hale Lani. Bikes and Beach Gear included.
KaMilo Luxury Living – Hale Lani Welcome to Hale Lani at KaMilo, a luxurious home for your Hawaiian holiday. This four bedroom three and a half bath townhome is perfect for large families or friends to gather for a Hawaiian vacation. Beautifully and comfortably...
Incredible Views Milowai 1 Bed 1 Bath Condo
A peaceful retreat where you can hear the ocean waves from your king size bed. Sunrise and sunset views from your lanai. Located on the 3rd floor with elevator access. Milowai complex has a heated pool with BBQ`s and a small library for guests use. There is a 5-mile...
Kamahana 19: 2 BR, 2 BA Condominium in Princeville, Sleeps 4
Completely remodeled two bed, two bath private condo. It is aspected towards the golf course and feels more like a home than a condo. Open main living area with incredible tradewind breezes and a a large covered lanai. The kitchen boasts modern appliances and brand new...
Rainforest Retreat w/Outdoor Fireplace & Hot Tub
Located 10 minutes from Volcanoes National Park, come spend your days exploring, hiking, golfing or simply relaxing in our unique, tranquil setting. This beautifully crafted home has all of the amenities and comforts you need. From soaking in the large hot tub to making...
Beautifully 2-BR Oceanfront Condo with A/C
Royal Kahana end unit condo 920 offers what is needed to make lasting memories in comfort and private. This spacious 2-bedrooms/2-bathrooms (1140 sf) with central-air has stunning ocean views from the 9th floor (ocean views from both bedrooms and living room)! The...
Doesn't get better than this! A201
A LITTLE ABOUT THIS CONDO...Lokelani A201 is a 1130 sq. ft., 2 Bedrooms (A/C), 2 Bathrooms (sleeps 4), corner unit. Unobstructed panoramic ocean views, 30 feet from the private sandy beach with surf break. Boogie boarding, paddle boarding, surfing, snorkeling right out...
Maui Sunset Vacation Rentals B405
Watch the life of Maui unfold from the morning till evening from your private 114 sq foot private view deck. Located on the fourth-floor view of tropical gardens and the ocean beyond. Quiet location features large private view deck and renovated interior. Doesn't get...
Maui Sunset Vacation Rentals A516 ocean view
Top floor, best location of any 1 bedroom #A516Watch the life of Maui unfold from the morning till evening from your private 114 sq foot private view deck. Premium condo suite located near the pool area. New flooring throughout 2023. A516 is on the top floor ocean and...
Maui Sunset A415: 1 BR, 2 BA Condominium in Kihei, Sleeps 5
Condo rental on the beach in sunny Maui, Hawaii. Condo A415 has one of the best locations for views of the ocean and Maui vistas.Great location, one bedroom two bath ocean view. Watch the life of Maui unfold from the morning till evening from your private 114 sq foot...
Luxury Condo! Short walk to the beach and pool! Kolea 13E
Kolea 13E is a luxury condo with everything you need for your vacation. This second story unit has an ocean view of Anaeho'omalu Bay and mountain views that can be seen from the lanai off the main living space and the master bedroom. This 3 bedroom, 3.5 bath is...