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.
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...
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...
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...
Historical Lodge at Pu'u O Hoku Ranch on Molokai
“Pu'u O Hoku” is true to its Hawaiian name — which means “Hill of Stars”— surrounded by more than 14,000 acres of protected land, immersed in the transcendent beauty of forest, sky, and ocean. The Ranch is a family-owned biodynamic and organic ranch and...
^Marriott's Ko Olina Beach Club^ - 1BR 1BA MT. VIEW ^INSTANT BOOKING^ 1 car free
Marriott's Ko Olina Beach Club - 1BR 1BA MT. VIEW FULL resort access***INSTANT BOOKING***1st car park for free ($45 a day value)Full access to the resort’s services and amenities are included with every reservation.3 nights stay checking in on 3/11/2025 is for Ocean...
Gorgeous home with private pool, hammock, large patio, lanai, & enclosed yard
Kohola HaleOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Escape to your own private oasis in the prestigious community of Princeville on the North Shore of Kauai at Hale Mahana....
Modern 1BR Kamahana Condo with Tropical Breezes, Pool
Modern 1BR Condo with Ocean Breezes – Kamahana, PrincevilleWelcome to your serene slice of paradise on Kauai's North Shore! This beautifully updated 1-bedroom, 1-bathroom condo in the highly sought-after Kamahana complex offers the perfect blend of island charm and...
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...
2 Private Homes for 1! Pool & Waterslide - Cove Hale
Extend your escape with our special offer: Book 5 nights and enjoy the 6th night free! Use promo code: 6THFREEBlackout dates: November 22–30, 2025 and December 20, 2025 – April 20, 2026Cannot be combined with other promotions or discounts. Located just 0.2 miles...
Spacious 2 Bed with Views!
Boasting a spectacular location on Maui’s western coast, this 2-bedroom condo provides a dreamy setting for a family or group vacation. The oceanfront resort is an idyllic retreat with a stunning tropical pool, exciting sports courts, outdoor BBQ area, and full...
Hale Kai O Kihei Condo w/ Ocean View, Shared W/D-Waves Await
Hale Kai O Kihei 216Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'This Hale Kai O’ Kihei condo offers a breathtaking ocean view from every room and includes a private lanai that...
BEST Ocean Mountain Views, AC, Heated Pool, Pickleball
Unit 833 at Nihi Kai Villas: The best view in Poipu! See why our lanai has been chosen site for wedding and vow renewals. Unparalleled ocean, coastline and mountain views from this top floor expansive lanai open to a ten mile coastline view and the central and highest...
Exceptional 10/10 Peaceful Forest Paradise
Immerse yourself in an exceptional all 5-star experience in this native forest home on the Eastern tip of the Big Island, This newly renovated, lava themed house, in the lush subdivision of Leilani Estates, provides the perfect space to kick back and relax in style....
Kiahuna Plantation Resort 76 Ocean View 2 BD 2 BA
Wake up to the sights and sounds of the Pacific in this two-bedroom ocean view condo. Just steps from the shoreline, it’s an ideal home base for your Kauai adventure. Unit 76 Ocean View 2 Bedroom 2 Bath• Two-level condo in building 14 with bedrooms & bathrooms...
Relax in this beautiful ocean view studio condo!
Welcome to our beautiful studio unit B303 in the beautiful Papakea Resort which is located in West Maui. This condo is on the third flood in the highly desired "B" building. Our unit is steps away from the ocean, pool, cabana, and has a putting green right off of the...
Lanikai Breeze – Contemporary Comfort Steps from the Shore
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.Just steps away from coveted Lanikai Beach,...
Breathtaking Ocean View with Private Pool!
30 Days or more Rental!Discover this 2-bedroom gem in Honolulu. This tranquil house features 1 king bed and 1 queen bed, perfect for a peaceful getaway. Bidet in the bathroom, along with amenities like AC, WiFi, and a washing machine. You're sure to make fantastic...
NEW Modern Family Retreat - Hanalei Happiness - Near Best Beaches, Trails & Eats
Step into an elevated retreat, thoughtfully designed for traveling families. This modern hideaway is rich in amenities and curated for comfort, all while embracing the vibrant spirit of Hanalei.- Just 8 Minutes to Hanalei- Close to Best Beaches, Trails & Eats- Ultimate...
Poolside Ground-Floor Villa |Walk to Beach|Hot Tub
Summary:E110 | TA-120-625-1520-01Walk to the best beaches on Kauai! In a tranquil setting surrounded by lush tropical landscaping, unwind in the pool, soak in the hot tub, work up a sweat in the fitness center or on the tennis courts, walk to multiple beautiful beaches...
Off Grid Getaway w Panoramic Ocean Views
Aloha & welcome to our lush 11 acre OFF GRiD Paradise!This home operates completely off the grid meaning we gain 100% of our power from solar energy, our water is catchment (rainwater), and we have propane to power any gas devices. You will have access to our beautiful...
Steps to Sugar Beach!
Hosted by VacaMauiWe chose Kihei Holiday due to it's incredibly close location directly across the street from Sugar Beach.Stainless steel appliances, air conditioning, beach gear, and a flat screen TV are some of the amenities you will enjoy during your stay.This unit...