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.
~ This Is Wailea Living ~
This is Wailea Living!Nestled in a private and secluded enclave between the Wailea Blue Course and the Wailea Tennis Club, the Wailea Grand Champions Villas are where travelers can golf, play tennis, be pampered at the Wailea Grand Spa, whale watch or turtle spot, or...
Hanalei Bay Villas #22 - a 2br / 2.5BA, mountain and golf course view condo
Hanalei Bay Villas #22 is a spacious two bedroom, two and a half bath, two story stand-alone condominium. With an additional queen size sleeper sofa, this unit sleeps six comfortably. Beach access is available past the 1 Hotel Hanalei Bay next door. Views include the...
Come spend some time at Our Kohala Ranch House!
From our covered lanai you have expansive views of the ocean, the sprawling Kohala ranchland and Haleakala on neighboring Maui. There really is no better way to start your day!And what you do with the rest of your day is completely up to you: Feeling a bit lazy? Relax...
Halii Kai 12H - 3 Bedroom Deluxe Ocean View Hali Kai Vacation Rental
Sit back, relax and enjoy the best view of the Waikoloa Beach Resort! The view from this villa is nothing short of breathtaking. From this villa you overlook the signature hole of the golf course and onto the blue waters of the Pacific Ocean. The view from this villa is...
Maui Resort Rentals: Honua Kai Hokulani 1034 – Expansive Top Floor Corner 2BR w/ Gorgeous Mountain Views!
Perched high above the palms on the top floor of the Honua Kai Resort, this exquisite 2-bedroom, 2-bathroom corner penthouse showcases stunning views of the lush West Maui Mountains, complemented by peekaboo glimpses of the sparkling blue Pacific.With nearly 1,300...
Ko Olina Beach Villas B103: Spacious Elegance & Oceanfront Views
Welcome to Ko Olina Beach Villas B103 by Gather, a ground-floor beachfront villa offering a breathtaking oceanfront getaway in the heart of Ko Olina. This three-bedroom, three-bathroom retreat is the perfect blend of luxury and comfort, designed to provide an...
Front Row Eclectic Updated Oceanview S Kihei 1 bedroom 1 bathroom condonn
Welcome to Maui Vista 1312. This eclectic updated partial oceanview 1 bedroom condo is located in the heart of South Kihei. This condo can accommodate 4 people & has everything needed to feel at home. Cross the street & end up at Charley Young beach which connects to...
AlohaCation - Oceanfront Work and Family Time
Work from Paradise or Enjoy Family Time by the BeachImagine waking up to breathtaking ocean views, working remotely with the sound of waves in the background, or spending quality time with your little ones on a peaceful, safe beach. Our oceanfront apartment blends...
Includes Hilton Waikoloa Pool Pass for stays in 2025! Includes Golf Package.Wai
This vacation rental is professionally managed by ResorticaHawaiiWaikoloa Beach Villas E23Please scroll down for detailed informationHilton Pool Pass: Valid for stays now through December 31, 2026. Maximum 6 persons per pass (children under the age of 5 are not counted...
Modern Renovated Maui Kamaole Condo Near Main Pool, Beach Across Street
***Summer Discounts now available for July and August 2025! 15% off plus an extra 5% for weekly rentals and 10% for monthly! Quote calculates the lower rates!***This 1050+ square foot 2BR/2BA condo is in the highly desired Maui Kamaole complex, one of the newer condo...
❤️🏖BEAUTIFUL LARGEST 1BD, OCEAN VIEW ONE OF THE CLOSEST TO OCEAN 120 REVIEWS❤️
🏖 LARGEST ONE BEDROOM WITH OUTSTANDING REVIEWS. UPDATED! Newly Painted interior and lanai. COMPARE OUR FLOOR PLATE TO SEE OUR LOCATION COMPARED TO OTHERS ON VRBO.🌺 You are renting directly from the owners. We would love to have you stay with us. As our guest, you...
Ocean Views/Private Swimming Pool. Mauna Kea High Bluffs Home
This vacation rental is professionally managed by ResorticaHawaiiMauna Kea High Bluffs #9. Stunning Private Home with swimming pool and ocean views. Mauna Kea Resort Amenity Program add on optionPlease scroll down for detailed informationPLEASE NOTE: There is ongoing...
New Remodeled Kuaui Escape! 1/1 condo in charming Kapaʻa with WiFi, AC
Welcome to our charming one-bedroom condo by the beach in the heart of Kapaa next door to Coconut Marketplace. This newly remodeled one-bedroom offers a fully equipped kitchen,a furnished lanai,a king-size bed, and a sofa sleeper that can accommodate up to four guests....
Hale Honu - 5 Star Oceanfront Home Overlooking Turtle Cove!
Perched above historic Koloa Landing, also known as Hanaka’ape Bay, Hale Honu boasts dominant bay and ocean views. Just off your private lanai is some of the best snorkeling and scuba diving the island has to offer. Giant sea turtles can be seen below swimming and...
BEAUTIFUL CONDO WITH AWESOME SUNSET VIEWS
Beautiful two bedroom two bath luxury condo. Kitchen with granite counter tops and all stainless steel appliances. Bathrooms with granite counter tops and beautifully tiled bath/showers. This condo is located in Maui Kamaole One of Kihei best first class resort...
nPrivate, Walk to Beach, Golf, Shopping and Restaurants!
Located in Waikoloa Beach Resort at Vista Waikoloa.. Beach, Golf, Snorkeling, Seasonal Whale Watching, Shopping, Restauants, all minutes away!Our beautiful ground-floor condo, on the sunny/dry side of the island, is located in the luxurious resort of Waikoloa Beach. We...
Kahala Oceanside – Coastal Sanctuary with Panoramic Views
Kahala Oceanside is a private paradise retreat that comfortably sleeps 14. This luxurious ocean front hideaway on the South Shore of Oahu, known for its spectacular sunsets, is just minutes away from fine eateries, world-famous hikes, and the endless attractions of...
Gorgeous Views- Kuleana 514 1 bed/1ba condo
Oceanfront Paradise at Kuleana 514 – West Maui Getaway 1 Bedroom • 1 Bathroom • Sleeps 4 • Oceanfront ResortWake up to the sound of the waves and breathtaking views of Molokaʻi and Lānaʻi. Kuleana 514 offers the perfect blend of island comfort and modern...
Wailea Beach Villas PH309 - 3 Bedroom Ocean View Penthouse
Penthouse 309 at Wailea Beach Villas offers a distinctive blend of luxury and cultural charm, making it an ideal vacation rental for families or groups of friends. This 2,520 square foot ocean view suite is located on the third floor and is accessible via a private...
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...
Professionally designed and remodeled in 2021! 2 master bedrooms, spacious plan
2025: New appliances (French door refrigerator with filtered cold water and ice dispensers, ultra quiet dishwasher) and outdoor sofas.2024: (2) New sofabeds!2021: Professionally designed and newly remodeled! No expense has been spared to make this a comfort. All brand...
❤️PiH❤️ DREAMS COME TRUE ★ Private Pool and Spa ★ Golf Course View
Brought to you by Paradise in Hawaii Luxury Homes.Dreams Come True is a stunning home in the KaMilo community overlooking Mauna Lani North Course.We pride ourselves on providing some of the most sought after homes on the Kohala Coast. We have partnered with the owners...
Receive a $100 Gift Card for Snorkel Gear or Wailea Dining Options!
*Absolutely Stunning Panoramic Ocean and Island Views*Yards Away from Local Favorite Shops and Dining*4 beaches within 1-2 miles (Wailea, Ulua, Mokapu, Keawakapu Beaches) Experience paradise at Wailea Ekolu 104, where breathtaking panoramic ocean views and spectacular...
Beautiful oceanfront condo 🏖 As oceanfront as you can get 🐳 Royal Sea Cliff 209
Primo Kona Condo! This 2,110 square foot luxury condo located at a luxury resort offers a one-of-a-kind 932 square foot lanai offering a panoramic ocean view! The lanai is equipped with outdoor dining, a queen-sized sunbed, and loungers offering many options to be out...
Holy Kamaole! Beachfront Kihei!
** If this unit is already booked, check out our unit next door https://www.vrbo.com/9432451haLocation, Location, Location. Imagine fixing a meal while enjoying the sunset, or maybe watching the whales from our perfect beach front location on Kamaole One beach. This...
Hoolei Uni 31-2 Ocean view- ideal Wailea location walking to beaches and shops
Dramatic ocean views, this spacious town home is approximately 2500 sq ft of interior footage and 596 sq ft of lanai space. The Hoolei community is located directly across the street from the Four Seasons and the Grand Wailea Resort. Unit 31-2 has the a great location...
Hilo's Finest 2 bd Condo - Pool, A/C, Views!
Enjoy a stylish experience at this centrally-located condo. Far exceeds any Hilo Hotel. 2brm with living room with super comfortable couch and loveseat. FULLY air conditioned. The view is spectacular. 24/7 security building. Free assigned parking. Wifi with 3 smart...
WBH D225 Aloha Ola – Ocean and Pool View
Summary:This family-friendly beachfront, second floor 1-bedroom/1-bath air-conditioned Condo Suite comes with a comfortable king-size bed and living room couch that pulls out to a queen size sofa-sleeper allowing the unit to sleep up to 4 people. Just steps from the...
Maui Parkshore Condo with Kamaole Beach Views
Welcome to your comfortable 2-bedroom ocean view condo in South Kihei, the perfect Maui retreat for your dream vacation. The condo's location is just across the street from Kamaole Beach Park III, a popular family beach, making it easy to enjoy the sun, sand, and surf....
Hale Lani ~ Big Island Charmer with Panoramic Ocean Views ~ Near Best Beaches
This solar powered single family home is located on the coast in the foothills of hawaii island’s oldest volcano, Kohala mountain, with views of the coastline and ocean. This beautifully appointed home is conveniently located in the historic neighborhood of Kawaihae...
Blue Kauai Hale - Peaceful Multi-Level Home in Princeville
Relax with the whole family at this peaceful oasis. Blue Kauai Hale is the perfect base camp from which to explore and adventure on Kauai, then return home to soak in the hot tub and create more memories over a gourmet meal.Recently remodeled throughout with 4 bedrooms...
SLEEP NUMBER BED! #759 1bdrm-A Guest Favorite-Ocean/Beach View w/ XBOX & ROKU!
**********Watch our Beautiful Video: It's picture #3 (the daytime table)**************NOTE: We are in TOWER 2 - No exterior painting is being done on our Tower (we were last year). Only Tower 1 is being painted during Fall of 2024- Early 2025. Stay with us and not deal...
Beautiful Ocean View! Newly renovated kitchen and 2 Air Conditioners
Our 2 bedroom condo is located on the 3rd floor at the Kihei Akahi and just steps away from one of the most beautiful beaches on Maui - Kamaole II Beach. Newly renovated kitchen. We installed not one but two split Air Conditioners! One split AC is located in the Living...
SEArider ONE at Turtle Bay (2 bedroom / 2 bath) - Kuilima Estates East
~ You just found your Base Camp to explore the North Shore of Oahu ~Our condo has just been completely remodeled and redecorated with two brand new bathrooms as of September 2021. We are situated alongside the Palmer Golf Course and are a short 5-10 minute walk to the...
Free parking marinesurf Comfort central Waikiki
Aloha our unit have free reserve parking ,5-10 minutes walk to the beach , heart of Waikiki, International market, DFS , Royal Hawaiian shopping center. You stay in a very convenient and comfortable place .
Ocean View, Beach Front, Dream Vacation Villa, at Kahalu’u Snorkel & Surf Beach.
Our luxurious condo is located in Kailua-Kona at Beach Villas at Kahalu’u (BVK). This is your home away from home with 2 bedrooms and 2 full bathrooms that each have walk in showers. Our welcoming condo features 1 king bed and 1 queen bed, which is perfect for a small...
Wailea Grand Champion Villas 3-Bedroom updated Home centrally located in Wailea
Aloha, our home is located in the center of Wailea on the first hole of the Wailea Blue Course and is perfect for families or couples. The 3 bedroom home was recently updated, has high ceilings, and large, sliding glass doors that look out over the golf course and...
South Kihei Top floor Ocean View & easy walk to the beach.
2 Bedroom, 2 Bath, Sleeps 4 (2 Queen Beds) This spectacular TOP floor unit features Split System air conditioning which allows for individual climate control in each room. The A/C accommodates year-round enjoyment of the fully equipped chef’s kitchen, completely...
FULL OCEAN VIEWS Poipu Beach House, LOVELY lanai and A/C
Aloha & welcome to our home - Hale Kika @ Poipu Kai resort. Hale Kika is an open concept beach house with great views from the main living area, 3 bedrooms and 2 1/2 bathrooms. Views from the house span from the Haupu Mountain to full ocean views. Our 2-storey home...
Halana Maile - Ocean Views, A/C, Beautifully Furnished Halana Maile Sleeps 8, 3200 sq. ft
HALANA MAILE AT KOLOA KAI VACATION RENTALSOcean-View Luxury Nestled on Kauai’s Crater RidgeWelcome to Halana Maile, a serene and luxurious retreat perched on the side of an ancient crater, offering breathtaking ocean views and easy access to Shipwreck’s Beach near...
Amazing view, Close to the beach, Wailea Ekahi Unit 20i
Condo 1 bedroom, 2 bath (sleeps 4)PRIME location on the front row in lower Wailea Ekahi, Wailea. Listen to the sound of the waves and enjoy the ocean views. Famous Keawakapu Beach is just steps away! Beautiful ocean views from every room. Enjoy the extra-large lanai...
PUN 202 Updated Oceanfront Condo at Punahoa Beach with Stunning Views
Punahoa 202 NEW LISTING! Refreshed OceanFront Condo with Spectacular Ocean Views for a Peaceful and Relaxing Hawaiian Vacation FREE daily activities included with your stay value up to $554! Complimentary admission, every day of your stay*: Whale Watching (seasonal),...
Largest Lanais in Lahaina! Ocean & Sunset Views HK245
Pure Luxury on Maui's Westside! A true romantic escape or the family vacation of a lifetime. You can have it all at Honua Kai Resort and Spa! Our desired inner courtyard sanctuary in the Hokulani Tower offers amazing amenities which include: 2 primary bedrooms with king...
Tropical Oasis! Beaches, Shopping & Comfort Pacific Shores A212
Experience paradise at this beautifully updated 2-bedroom, 2-bathroom vacation rental at Pacific Shores in South Kihei. Overlooking a lush tropical courtyard, this serene retreat offers the perfect blend of comfort and Hawaiian charm. The fully equipped kitchen and...
Traditional Hawaiian House - Walk to Tunnels Beach
TVNCU #1146 - A gated entrance leads you through a 6 foot lava rock wall toward the rear, ground level peaceful house. Privately tucked away, on the Mauka (mountain) side of the road, behind a front house (where the housekeepers live), the rental house sits. Capture...
2 Bedroom Poipu Condo with Pool, Hot Tub walk to Beaches
Regency at Poipu Kai 911 is an air conditioned, ground floor suite located just steps to the pool. This 2-bedroom, 2-bath suite is great families and walking distance to the beach. This stunning condo has been upgraded throughout and is one of the few air-conditioned...
Gorgeous House Next Door to 1Hotel Hanalei Bay - Awesome Views Unit #10
*Please review the current quarantine requirements on Kauai at: https://www.kauai.gov/covid-19 before booking.Hanalei Bay Villas #10 - Look no further - 'Paradise Found' So whether you are honeymooning or just looking for a very well deserved vacation you are always...
Ocean View, 1st Floor, Spectacular Remodel, AC every room, Inner Courtyard
Check out our over the top remodel in every room. Redesigned throughout. Private guest room. AC in every room. The best location in The Palms. 1st floor walk out , near pool Provide beach chairs, ice chest, beach towels, boogie boards and other beach items. Puzzles,...
Impressive 2 Bdrm+2 Ba Paradise Condominium at Wailea Grand Champion Villas
Treat yourself to an impeccable Front-Row 2 Bedroom + 2 Bathroom paradise condominium at the Wailea Grand Champion Villas. This is the finest that Wailea Grand Champion Golf Villas has to offer in a 2 bedroom + 2 bath category. Upgraded in every way with split A/C...
Ultimate Oceanfront Luxury-Private penthouse in South Maui-Perfect for families
The Penthouse Maui, our luxurious 2,824-square-foot vacation rental, sits directly above the golden sand and shimmering surf of Kamaole Beach II in the heart of sunny Kihei, Hawaii. Whether you’re celebrating with family, vacationing with friends, or simply seeking a...