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 beautiful beachfront Hanalei Bay home is located steps from the sand
This beautiful beachfront Hanalei Bay home is located steps from the sand on Kauai's majestic north shore. It offers panoramic views of an iconic beach and its surrounding mountains within a quick walk to the Hanalei Pier for surfing and swimming and the Hanalei River...
Ground floor Condo with private golfside lanai, and views of golfcourse
The Golf Villas at Mauna Lani E3Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Promotion Announcement: Complete your reservation and leave a review between May 1 and December 31 to...
PRIVATE HOME OASIS-3 BEDROOM-OCEAN VIEWS-POOL-HOT TUB-METICULOUS CLEANING
Book With Confidence,This Gorgeous, Newly Remodeled, 3 Bedroom, 2 Bathroom Home That Has Beautiful Ocean Views, A Stunning Resort Style Backyard With A Pool Including A Waterfall, Hot tub, And Tikki Torches, And Tropical Landscaping. This Property Is A Permitted Bed And...
New - Hawaiian Tin Shack
Escape to paradise at the Hawaiian Tin Shack, a cozy-luxe retreat in the Big Island jungle. Just 40 minutes from Volcanoes National Park and 20 minutes to Hilo, this 3-bedroom, 2-bathroom home sleeps 8 and features a private hot tub, fully stocked kitchen, and a...
Plantation Cottage: Lavish Fairway Oasis w/ Pool/Spa, AC, and Gorgeous Sunsets!
Experience island living at its finest at Plantation Cottage at Poipu, a stunning three-bedroom, three-and-a-half-bath retreat located along the first hole of the Kiahuna Golf Course in Koloa, HI. Blending plantation-style elegance with contemporary comfort, this...
Princeville Private 3 bed 2 bath w/AC
This private end of road cul-de-sac home has everything you need! It’s steps away from Princeville’s community center with fine dining, night life, shops, treats, and groceries. While central, this home is a personal hideaway with a private back yard backed up to...
Best Deal! Boogie Boards, Snorkel Gear, Baby Gear, Golf! Its all in the deal!
Call for our Introductory Special Pricing! New! Luxury 2BR, 2 BA ground floor villa with sophisticated tropical décor and direct beach access!Kolea, located just 30 minutes north of Kona-Kailua at Waikoloa Beach Resort between the Hilton Waikoloa Hotel and the Marriott...
Hale Minoaka Main by Destination Kauai - Poipu Beach Estates, A/C
E Komo Mai, Welcome to Hale Minoaka Main House!This beautiful new home is offered as a 1-bedroom with a spacious open living concept. Split AC in bedroom and living room. Located in Poipu Beach Estates - a premier neighborhood on Kaua'i's South Shore. Let this be your...
Seahorse Luxury Suite at Seaspray Ocean View
A private oasis across from the desirable Kahaluʻu Beach Park. This two bedroom luxury suite is bright & airy with a private lanai & your own KOI pond. A private guest only pool deck includes a barbecue and dining area for outside entertainment. The living room is a...
First Class Luxury Beach Front Resort Condominium
Located in the World-Famous Ko Olina Resort and Marina on the 2nd of four lagoons, you’ll enjoy the mile and a half walkway along the four lagoons as you pass the newest 4 Seasons in Hawaii, the Disney Aulani Hotel & Spa, the Marriot Ko Olina Beach Club and us, The Ko...
Hale Kalapu Amazing North Kaanapali Ocean Views 3BD Private Home Walk to the Beach
Hale Kalapu NEW LISTING Spectacular Panoramic Ocean Views from this 3Bedroom Home on the North Kaanapali Hillside! FREE daily activities included with your stay value up to $1035! Complimentary admission, every day of your stay*: Lu'au, Golf, Whale Watch (seasonal),...
Fantastic unit! 10/10! Hear the waves from the lanai! 1 bedroom unit. Sleeps 4
This one bedroom, smoke-free condo, is located in Ekahi Village, and is a short (less than 4 minutes) relatively flat walk to the beautiful Keawakapu Beach. The unit is located in the lower village. You can stay on the beach for the day or enjoy the amazing new...
Direct Ocean Front
We are new to the vacation rentals and we are excited to host you at our 1 bedroom, 1 bath newly remodeled ocean front condo with spectacular panoramic ocean views. Enjoy your morning coffee with sunrise over Haleakala Crater. Green sea turtles rest almost every night...
ALII 4104 BeachFront 2Bedroom wBreathtaking Ocean Views
Kaanapali Alii 4104 NEW LISTING Enjoy Breathtaking Ocean Views, Top-Notch Amenities, and Direct Access to Beautiful Kaanapali Beach and World Famous Dining and Shops FREE daily activities included with your stay value up to $1035! Complimentary admission, every day of...
COZY HIDEAWAY IN THE OHIA RAINFOREST LOCATED BELOW VOLCANO NATIONAL PARK
Entire house 2 bedroom full kitchen 1.5 bath washer&dryer and a screened in lanai on 2 acres of ohia forest with fruit trees private and quiet with lock box for entrance....some of the things that I provide is lot of clean towels a full kitchen with fridge stove...
Ground Floor Luxury Penthouse at The Villas | F100
Summary:F100 | TA-018-220-0320-02Wake up in paradise at Villa F100, part of the exclusive Villas at Poipu Kai. Enjoy tranquil garden views from your private lanai, cook gourmet meals in the fully stocked kitchen, and dine al fresco under tropical skies. Relax by the...
Stunning Oceanfront Home @ Kalapaki Bay, AC, Sleeps 8
Luxury oceanfront home in paradise!From endless deep blue of Kalapaki Bay to emerald greens of the Hokuala golf course this home is the kind of paradise you’ve been dreaming of. Perched upon the Kalapaki Cliffs, this location provides the ultimate indoor-outdoor...
Beautiful Ocean Front Ground Floor NEWLY RENOVATED 3 BRM
Our condo is family owned and operated and is a beautiful and spacious 3-bedroom beach front condo offers stunning ocean views from the living room, kitchen and master bedroom. The second and third bedrooms also enjoy ocean views.The kitchen was renovated in 2024 with...
Air Conditioning,Pool, Surf Boards &Beach supplies,Pool, Lanai,Sleeps 4, kitchen
We are not a resort so you won’t have to sit through any surprise time share spiel/talk. We had to go through that when we were guests. Located in Princeville. Ground floor, corner unit! New Air conditioner, 2 Surf Boards, boogie boards, 4 snorkel gear sets, 4 beach...
Polo Beach House - South Maui Home with Direct Beach Access
Polo Beach House is a unique 3500 sq ft property with singular direct beach access to Polo Beach.Walk out of your oceanfront yard over a short lava rock path to put toes in the powdery sand, snorkel, boogie board and sand castle. Come back to jump in the pool, enjoy a...
Wailea Beach Villas PH111 - 2 Bedroom Garden View Penthouse
Curated with our guests in mind, Wailea Beach Villas PH111\'s outdoor elements are just as immaculate as the home’s interiors. Unwind and enjoy peekaboo views of the ocean along with tropical greenery from your private lanai. The pristine Wailea Beach is located...
Experience Luxury at Kaanapali Royal G303
*Season Promo ~ Stay now through Dec 15, 2025: Book 5 or more nights, get 1 night Free! Kaanapali Royal G303 is a 2-bedroom condo featuring amenities such as a large private lanai, a flat-screen TV, and central air conditioning. This condo can accommodate up to 6 guests...
The Ultimate Oceanfront Experience. Tropical Luxury And Spectacular View
SIMPLY WOW! If you want the best of the best, this is your opportunity to reserve The Ultimate Oceanfront Hawaiian Experience. A highly upgraded 3 bedroom 2 bath spectacular ocean front property with amazing ocean views and a modern tropical interior at The Honokeana...
Coconut Plantation 1190-1: Spacious 3BD Resort Villa w/ 3 Lanais—Walk to Lagoon
This property is offered as a monthly rental. Although full-month occupancy is not required, the monthly rate remains fixed and applies in full, regardless of the number of nights stayed, as prorated rates are not available.Welcome to Coconut Plantation 1190-1 by...
Luxury Oceanview Wailea Point 3-Bed Vacation Home
Discover luxury living at Wailea Point Resort, nestled between prestigious resorts, this oceanfront paradise promises the ultimate South Maui experience. Our 3-bed luxury condo offers four bathrooms, in-suite laundry, two workspaces, and a chef's kitchen with top-tier...
Fully Remodeled! Amazing OCEAN, Mountain, City Views! 2-Bed/2-Bath Sleeps 6!
Waikiki Shore #818 – 2161 Kalia Rd.(ONLINE RESERVATIONS CONSIDERED REQUESTS SUBJECT TO APPROVAL)You'll enjoy spectacular Ocean Views from this luxurious 8th floor beach condo (932 interior sf + 160-sf lanai), recently renovated and impeccably designed with a...
Kailani Kona- Ocean view, top floor Downtwn w pool
Aloha! Enjoy Kona in our serene 1br top-floor corner unit condo with a sweeping view of the ocean! We are centrally located steps from downtown Kona and across the street from beach access. There's a dedicated parking spot, community pool, in-home laundry, and all the...
Poipu Beach Making Memories, 2-Bedroom, AC, Pool & Walk to the Beach, Kauai, HI
Experience Poipu Beach and make memories at this 2-bedroom condo at Kahala in the Poipu Kai Resort. From the moment you enter this ground floor-end unit with 1150 square-feet and quiet peaceful garden view, you will feel like you've entered a true Hawaiian paradise. The...
BEACH FRONT ESTATE SANDY BEACH Heated Saline Pool/SPA 360 Views: Please Inquire
30 Day Minimum Stay Required: Please InquireShare the romance and beauty of the North Shore with your entire family! Swing open the gate to our Sandy Beach, sink your toes into the white sand and say “Aloha” to the turtles who come to our beach each afternoon, or...
Hale Maluhia - Poipu Beach Estates Home with Heated Pool
Enjoy the luxury and comfort of our newest Elite home centrally located in Poipu Beach Estates. This custom home takes full advantage of many views and is also positioned to enjoy the fabulous trade wind breezes. The spacious and open great room has sliding doors that...
Spacious home in a lush green piece of paradise
Nice, comfortable home on large lot with spacious lanai and fenced back yard. Use our home as a base for your Hawaiian adventure. Cook meals in our new kitchen with fresh, delicious and healthy fruits and veggies available at local markets. Barbecue on the lanai or eat...
Lush Oceanview Villa w/Hot Tub & AC - Fairwayfront at Hualalai: 3101 Kumukehu
Welcome to the 3BD Golf Villa (3101) at Hualalai Resort, an exceptional ocean-view retreat set along the premier “front row” of the prestigious Hualalai community. Spanning 2,882 sq ft of refined indoor–outdoor living, this single-level villa offers three ensuite...
Poipu Kai Kahala 814 - Two-bedroom Garden View condo on the island of Kaua'i.
Poipu Kai Kahala 814 - Two-bedroom Garden View condo on the island of Kaua'i. Primary bedroom: King BedPrimary bathroom: full bath with shower tub comboBedroom 2: QueenSecond bathroom: full bath with shower tub comboLivingroom: Queen sofa bedMax Occupancy: 6Laundry: in...
Hale Makala - Luxurious Hanalei Home TVNC #5093
Hale Makala, Luxurious Hanalei Home Renovated to PerfectionEscape to Hale Makala and experience ultimate luxury. Immerse yourself in the perfect fusion of traditional Hawaiiana style and modern design at Hale Makala, a recently renovated luxury home that promises a...
1BR/1BA Ocean View! 3 Minute Walk To Poipu Beach!
𝐖𝐞𝐥𝐜𝐨𝐦𝐞 𝐭𝐨 𝐒𝐚𝐧𝐝𝐲 𝐃𝐨𝐨𝐫'𝐬 𝐬𝐩𝐚𝐜𝐢𝐨𝐮𝐬 𝐎𝐜𝐞𝐚𝐧-𝐕𝐢𝐞𝐰 𝐑𝐞𝐭𝐫𝐞𝐚𝐭 𝐢𝐧 𝐏𝐨𝐢𝐩𝐮!Discover your perfect Hawaiian getaway in this newly...
Charming Kihei Oasis Vistas
Summary:Bright, modern, and spacious. Thoughtfully designed to elevate your experience with us. This completely remodeled one-bedroom, two-bathroom condo features luxurious touches throughout paired with nice ocean view from the lanai. Located in the sunny and vibrant...
Hawaiian Serene Paradise Oasis at the Pool
Indulge in the serene ambiance of Maui Kamaole C-106, a sparkling clean condo conveniently located right next to the pool and just steps away from the stunning Kamaole III Beach. Featuring two tranquil garden patio lanais, including a completely private one, this ground...
Luxurious Ho'olei Villa with Ocean Views, Two Story Townhouse!
Stay longer, enjoy more! Book 10+ nights and receive a free mid-stay clean. Book 14+ nights and get one night free!This property is hotel zoned, and not being affected by the recent proposed legislation.Welcome to this luxurious Ho'olei Villa with amazing ocean views!...
❤️PiH❤️ SERENITY VILLA ★Free Hilton Resort Passes ★Free Private Beach Club
Serenity Villa brought to you by Paradise in Hawaii Luxury HomesWelcome to our 4 bedroom Serenity Villa at KaMilo, on the Big Island of HawaiiBig Island is such a wonderful place to spend with your friends and family, children and grandchildren. Vacations create such...
Wailea Ekahi Village 29D - 1 Bedroom Ocean View Condo
This Wailea Ekahi Village residence completed a beautiful renovation in 2022. From colorful artwork to comfortable and sleek furnishings, you will instantly recognize why this Wailea vacation rental earned our highest internal ranking of \'\'platinum\'\' status. This...
Wailea Elua Village 1703 - 2 Bedroom Oceanfront Condo
Elua 1703 is a distinctive oceanfront vacation rental, perfectly situated directly in front of the renowned Ulua Beach and the Wailea Beachfront Walking Path. What sets it apart is its unique privacy, surrounded on three sides by lush, meticulously landscaped gardens...
Quiet North Shore Beachfront Home
This beachfront home is located in a quiet family neighborhood. Party animals, please look elsewhere! We are well off the main road with very little traffic making it a great place to take walks or go jogging. We are situated on a long white sand beach ideal for...
Ho'ohu Nani: Private Ocean View Estate in Poipu with Pool, Jacuzzi & AC
Ho'ohu Nani has Four Bedrooms (2 Master Suites), Den with Fold-Out Couch, Four Full Bathrooms, and Two Half Baths. Ocean Views from Upstairs Living Area and Covered Lanai. The Kitchen includes top-of-the line appliances with a new Wolf Range, beautiful granite counter...
SALE! Luxurious Ocean Front Penthouse 2Bd/3BathnSave 200 USD/night on open dates
2Bedroom/3Bath Most Incredible Ocean Front Penthouse with Incomparable Views Central AC ThroughoutThis gorgeous, remodeled, professionally decorated villa is located within the premier Kapalua Bay Villa Ocean Front Resort. Luxuriate in incredible ocean and island views...
Wailea Oceanfront Private Home
State of Hawaii Transient Accommodations Tax License #TA-053-364-5312-03County of Maui Short-Term Rental License #Hotel-ZonedThis home defines the best of Maui with lava step access to a sandy, swimming beach on one side and a lava rock beach on the other side.This...
JUST REMODELED Spacious & Exceptional Value! Tropical Garden & Ocean View!
We invite you to enjoy days of fun & discovery on Maui in our bright, spacious, attractively decorated, comfortable, fully-equipped condo. Easy tropical living for all.Enjoy exceptional value with affordable rates, ocean view in the distance, a larger floor plan &...
(P17D) Hale Blue Hawaii 1Br with Loft, Puamana, Pool, Wifi
Welcome to Hale Blue Hawaii at Puamana 17D! Ideal for a family beach vacation, this spacious, two-story villa offers top-notch features throughout as well as plenty of on-site resort amenities located just steps from your door. Start your days with breakfasts and fresh...
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...
Watermark - Luxury 2BD/2BA/1PA on 14th floor with an Ocean View!
This unit has 2 king size beds which can accommodate maximum of 4 people. This picture-perfect luxurious unit has 2 bedroom/2 bathroom with 1 designated parking spot. The condo is located at a very convenient location at the heart of Waikiki; only 7 minute walking...
Stunning Ocean View Gem with AC: Kamaole Nalu 504 - Your Island Getaway!
Kamaole Nalu #504 – Direct Oceanfront Luxury in KiheiKamaole Nalu #504 places you just steps from the golden sands of Kamaole Beach Parks I and II with unobstructed oceanfront views. This two-bedroom, two-bathroom fifth-floor condo has been designed for both comfort...