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.
New Owner Special! Ocean View in KoOlina, HI
Create magical memories at this unique & family-friendly home. Koolina is a resort community with easy access to fine dining, boutique shopping, entertainment and Nature. We are out of the congestion, traffic and crowds of downtown. We are on the drier side of the...
Maui Resort Rentals: Westin Ka'anapali Ocean Resort South Studio Islandview Villa
This island view luxury studio villa sleeps up to 4 with one king sized bed and one queen sized convertible sofa sleeper. It is located in the Westin Kaanapali Ocean Resort Villas South. The villa is equipped with a gourmet kitchenette with granite countertops, a two...
Includes Beach Gear! A101 Vista Waikoloa
Vista Waikoloa A101Please scroll down for detailed informationBedroom Configuration:Master Bedroom: King BedGuest Bedroom: Queen BedAmenities:Beach Equipment: All of our vacation rentals include beach towels for the maximum occupancy, four beach chairs, two boogie...
Oceanfront, Renovated & Accessible Downtown Kona - Beautiful Ocean Views! 1st Fl
Accessible and modern ground-floor, 2 bedroom/2 bath unit with spectacular ocean front views on a 200 sq ft lanai. Only one small step from a parking spot directly in front of your unit separates you from your Hawaii Island home (walk around to the right for step-less...
Luxurious Golf Course Ko Olina Kai Estates Getaway w/Parking & Near the Beach
This property requires a minimum 30-day rental. Book with confidence—professionally managed by Ali'i Beach Rentals, an award-winning property management company.This property is located at 92-1043 Koio Drive.This enchanting second floor home away from home is situated...
LUXURY 2-Bed Condo, Kitchen, Wi-Fi, Parking, W/D, AC, LEGAL Monthly Rental!
Allure Waikiki #804 – 1837 Kalakaua Ave.(LEGAL 30-Night Minimum Rental in the Resort Zone! Max Stay 3 Months. ALL MONTHLY RESERVATIONS ARE SUBJECT TO APPROVAL.)Experience luxury Waikiki living at its finest! This 2-bedroom, 2-bath condominium with high-end touches...
Magic Sands Retreat: Remodeled Cottage,Walk to Beach, Incredible Location,AC!
The Magic Sands Retreat is a quaint 3 bedroom/2 bath cottage just around the corner from the famed Magic Sands Beach and the Ali'i Drive beach corridor. Just a 10 minute walk to the most popular beach in Kona! This upgraded home shows attention to detail with an artists...
Direct Beach Access - Best Location - Wailea Beach Villas H101 - Walk Everywhere
RARE NOVEMBER OPENING - THANKSGIVING AVAILABLEThe best location in Wailea! Quick 2-minute walk to Wailea beach, shops, restaurants & the stunningly scenic Wailea Beach Path. BOOKING CALENDAR/MINIMUM NIGHT STAY:Our calendar opens 1 year in advance. Please reach out if...
Luxurious & Spacious Ocean Vistas
Summary:Beautifully remodeled in early 2023. This elegant 2-bedroom, 2-bath condo features upscale touches with magnificent ocean views. Located steps from Wailea, all of Maui is within reach. We offer a fully stocked kitchen for those who want to cook. Enjoy the...
Fabulous central location! Walk to restaurants, grocery store, and many beaches.
FABULOUS CENTRAL LOCATION! This brand new interior remodeled condo is walking distance to the Kailua pier, beaches, restaurants and we are right next to a grocery store. This unit is located one block from the best coffee shop in town. This older Hawaii complex has a...
Delightful home with private W/D, desk workspace, & a great location
Aloha Valley Shores | 31-Day MinimumOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Enjoy relaxing in a cheerful home filled with light, close to attractions but still providing the...
Wailea Beach Villas PH402 - 2 Bedroom Ocean View Penthouse
Experience the very best in tropical island living from ocean view Wailea Beach Villas Penthouse 402. Revel in sweet sunsets and seasonal whale watching from your spacious, private lanai with scenic views of the Maui horizon, Molokini Crater and the island of...
Maui Resort Rentals: Honua Kai Konea 529 - 5th Floor 3BR w/ Ocean Views from Every Room!
This three-bedroom deluxe oceanview residence offers breathtaking views of the Pacific Ocean and neighboring island of Lanai from its prime 5th-floor vantage point.The residence affords a perfect opportunity to gather, reconnect, and celebrate. There is ample room to...
Cottage on Beachfront Estate property, central Hanalei Bay
This amazing and completely refurbished home is situated on a stunningly beautiful one-acre, gated OCEANFRONT estate property, right in the middle of magical Hanalei Bay. It is, in fact, one of the ONLY vacation rental cottages on beachfront property to be found...
Tropical haven, close to beaches and shopping
Paki Maui 414 is a 1-bedroom, 1-bathroom condo located on the fourth floor with wonderful garden views from your lanai and floor-to-ceiling sliding glass doors, bringing natural light into the condo. The condo does have a split air conditioning in the bedroom and living...
NP B18 Remodeled Oceanfront 1BD Steps to Pool
Napili Point B18 NEW LISTING Wake up to Amazing Ocean Views in this Beautifully Appointed Ground Floor Condo at Napili Point! FREE daily activities included with your stay value up to $570! Complimentary admission, every day of your stay*: Whale Watch (seasonal), Dinner...
Sunset Hale: Spectacular Oceanview Home w/Private Pool & Spa, AC & Lanai
Sunset Hale by Gather | Private Kona Retreat w/ Ocean Views, Pool & Lanai – 30-Night MinimumSunset Hale welcomes you to elevated island living on the sunny slopes above Kailua-Kona, where distant Pacific blues, fragrant palms, and a private stone lap pool create an...
Waikiki Banyan Condo With Panoramic 37th Floor Ocean Views by Koko Resort Vacation Rentals
Panoramic 37th Floor Ocean Views, Free parking & Wi-Fi The pool and all associated amenities will be closed starting April 7, 2025,for an estimated duration of 10 to 14 months to accommodate the RecreationDeck renovation project. Enjoy panoramic views of the ocean and...
Charming 3br Cottage w AC, Ocean Views
New Listing! Welcome to Kukuiula Vacation Home #2, a charming ocean view beach cottage located in the heart of Poipu's desirable Kukuiula neighborhood. This single-story plantation-style home beautifully combines vintage Hawaiian charm with modern luxury, offering a...
Oceanfront Condo & Pool, Beautiful views & Sunsets
***Professionally Cleaned Condo, No-Contact Check-In/Check Out*** Welcome to Hale Hui Kai 309! This beautiful condo is located within a beach-bungalow style oceanfront Complex, situated on the long span of golden sand that is Keawakapu Beach in Kihei. This 2 bedroom/2...
On Wailea Blue Golf Course ⛳️with Ocean View. 🌊
Hawaii GE & TA Tax ID # G/T 006-824-3456-01 Taxes on total amount is 17.42%. Not included in the vrbo quote. Required is a signed rental agreement between guest and owner.This rental agreement is in addition to the deposit. After you initial and sign the agreement, it...
MAKAI SUNSETS, Waikoloa Vista A202, LUXURY CONDO ⭐️⭐️⭐️⭐️⭐️ 58+ 5 STAR REVIEWS
MAKAI SUNSETS-A LUXURIOUS OCEAN VIEW CONDO CLOSE TO THE BEACH AT VISTA WAIKOLOA - THE ENTIRE CONDO HAS BEEN COMPLETELY RENOVATED AND UP TO DATE! THIS 2ND FLOOR CONDO IS IN ONE OF THE BEST LOCATIONS ON THE ISLAND! WALK 8 MINUTES TO A BEAUTIFUL WHITE SAND BEACH! OVER 1400...
SPACIOUS LUXURY - OWNER DIRECT - OCEAN peek-a-VIEW
Aloha! Welcome to our Maui paradise and your personal getaway to relax and regenerate. Whether this is your first trip to the Valley Isle or you’re a regular visitor, thank you for giving us the opportunity to host your special vacation. Bougainvillea-109 is one of...
Beautiful 1 bedroom/2 bath condo centrally located
Enjoy the lush beauty of Maui from this single level one bedroom, two bathroom condo located at Kamaole Sands in Kihei. Take a swim at the resort pool or at Kamaole Beach Park just across the street!At Kamaole Sands 8-203, you can relax on your beautiful lanai while...
Koa Lagoon- Beachfront - Spectacular Location with Incredible Views
The top floor ( 6th floor) Corner unit makes this a prime location! A beachfront location with a panoramic views of the gorgeous Pacific Ocean. This property is upgraded and updated with an open floor plan and two bedrooms and two bathrooms. The decor is tasteful and...
Ocean Front, Edge Of Cliff - Feel & See Every Crashing Wave From All Room
Full Ocean Front On Cliffs Of North Shore!Beautiful 2 bedroom/2 bath, ocean views from every room! Lay in bed from either bedroom & watch the crashing waves roll into the cliffs directly below unit! Both beds in each bedroom are Westin Heavenly beds!! Upgraded condo,...
Beachfront / Corner / Renovated / 2nd floor condo unit: F-204
Literally sitting at the waters edge, this elegantly furnished and tastefully designed ocean front condo is so close to the shore you almost feel like you can reach out and touch the water. It has an ocean view from every room except the guest bedroom which overlooks...
MK- D106: Convenient 1BR Condo, Lush Tropical Views
Embrace island living in this conveniently located, ground floor 1-bedroom, 2-bathroom condo at Maui Kamaole D106. The spacious open-concept layout features bedroom with a plush King bed with en-suite bath and a sleeper sofa for added sleeping flexibility. Enjoy your...
Escape to your private oasis perched on a cliff with a jungle view
Private island retreat with an awesome jungle view. Situated in an upscale Hilo neighborhood. Close to downtown, delicious restraunts, and a fun farmers market. This unit is a completely separate guest room that has a private entrance and private bathroom. Plus a...
Top Floor, Centrally Located Condo, AC, Private Lanai, Steps to Beach
A L O H A ! ! !Top Floor, Centrally located, Condo with AC. Sleeps 4+ Parking included for one vehicle Imagine stepping out onto your lanai with a cup of coffee, and feeling the Hawaiian breeze carry your worries away. Whether you're planning a weekend escape or an...
Escape to Wyndham Kona Hawaiian: Island Vibes, Spacious Villas & Beach Bliss
Get ready for the ultimate family escape to paradise at Wyndham Kona Hawaiian Resort on the breathtaking Big Island of Hawaii! Nestled along the stunning Kona coastline, this family-friendly resort offers the perfect combination of relaxation, adventure, and Hawaiian...
Islander on the Beach ONE-BEDROOM unit #308, Top floor, incredible Ocean Views
NO RESORT FEE, FREE WIFI in the condo and FREE DEDICATED PARKING.Unique Top floor One-Bedroom unit #308 is one of the only two truly one-bedroom units available in the Islander on the Beach resort. It features a separate bedroom with a California King bed; living room...
Hale Nani: New Poipu Villa - Pool / Spa + Ocean Views
Breathtaking, sensational, divine. It’s impossible to overstate the appeal of this exceptional villa, with its spacious, elegantly appointed rooms and gorgeous grounds set against a dazzling backdrop of palm-fringed golf course, dramatic mountains, glittering ocean,...
Ocean view house, short walk to beach, lots of extras!
10 out of 10, Traveler Award winner for 2024. Hanalei Bay Villa 26 is one of our most popular Kauai vacation rentals with its great views, short walk to beach, and updated interior. Bali Hai sunset views are just steps away. This luxurious 2br/2ba home at Hanalei Bay...
Kona Ocean View Suite - Walk to Shops and Dining
Welcome to our dreamy Kona getaway! This newly refurbished, luxury beachy retreat is designed for relaxation and convenience in the heart of Kailua Kona. Great for the Sunsets! Walking distance from Kona's best restaurants and bars, it provides easy access to Ali'i...
PURE ELEGANCE*OCEANVIEW Renovated Condo in WAILEA
For travelers seeking luxury and an escape from life in the resort town of Wailea, this complex is one of the most exclusive sanctuaries. The newly renovated 1536 square foot condo is a spectacular beachfront vacation rental with panoramic ocean views and extensive...
Alii Villas#303 Fully Remodeled Top Floor unit with Ocean Views
Alii Villas 303 – Top Floor Remodeled Retreat with Ocean ViewsStep inside to find a bright, open-concept living area with updated vinyl plank flooring, tropical furnishings, and a spacious private lanai offering partial ocean views—perfect for guests to enjoy...
*Ocean View * Newly Remodeled *A/C * Beach Access
Stylishly remodeled, comfortable unit with split system a/c and incredible ocean view from the private lanai, kitchen, and master bedroom.Each bedroom features a king bed, private bathroom w/walk-in shower, Toto toilet, and custom vanity. Designer Poggenpohl kitchen...
Kailua-Kona Oceanfront Home
Welcome to our exceptional oceanfront property, a luxurious home in one of Kona's most exclusive neighborhoods off Kailua-Kona’s scenic Ali’i Drive. With stunning views of Holualoa Bay and breathtaking ocean sunsets, this architectural marvel seamlessly blends...
Exquisite Renovated Beachfront Haven - Experience Sugar Beach #329
SUGAR BEACH RESORT, #329One Bedroom / One Bath Oceanfront CondominiumWelcome to Sugar Beach Resort #329, a beautifully upgraded one-bedroom condo located in the heart of North Kihei. With koa wood flooring, modern upgrades, and panoramic oceanfront views, this condo...
Maui Resort Rentals: Honua Kai Konea 416 - 4th Floor 1BR w/ Mountain Views
Konea 416 is a luxurious one bedroom mountain view suite that enjoys expansive vistas of the West Maui Mountains. The suite is ideally suited to take advantage of some of the most beautiful sunrises anywhere. Coupled with frequent afternoon rainbows, you will cherish...
Westin Kaanapali Oceanview - Christmas & New Years Weeks - Studio
We own a 2-bedroom unit that is available as a 2-bedroom, 1-bedroom, or studio. This listing is for the studio unit.While most guests do not know which unit they will be assigned to until their arrival, this is a fixed unit, 7569. This unit is located on the 5th of 6...
Mauna Lani Islands Townhouse - Private location - Walk to Beach and Shops!
Welcome to Paradise! We hope to host your stay!B2 is located within the Mauna Lani Resort at The Islands at a private, gated community situated along the famed fairways of Mauna Lani golf course. Handsome townhomes set within gardens of flowering plumeria, hibiscus and...
Ocean Front Waikiki - Best Views! CALL NOW FOR APRIL/MAY CANCELLATION RATE!
Amazing oceanfront apartment on the 5th floor of Foster Tower Residences, overlooking Kuhio Beach and the landmark Duke Kahanamoku statue in Waikiki. This beautiful condominium has been completely renovated with all new updates in 2021. 2 full bedrooms plus 'bonus' room...
Stay in our Private Recently Updated Home in The Villages-Closest to The Shops!
Welcome to our luxe retreat in The Villages at Mauna Lani—a private, gated community offering rare tranquility just 124 yards from The Shops and walking distance to all resort amenities. Guests love our home for its exceptional privacy, spacious layout, and refined...
Ali'i Kai 1-202 · Beautiful Mountain View Condo in Princeville
Recently remodeled 2-bedroom, 2 bath condo close to many amazing beaches. This unit features great mountain views and you can even peek at the ocean from the dining area to check out the swell. Close to restaurants, spas, shops, golf, and tennis this is the perfect...
KBM Resorts | FREE CAR | Mahana | Oceanfront | Gorgeous 2-Bedroom Condo! MAH-301
** Limited Time Special Offer: Reserve any KBM Resorts property in Hawaii with an arrival date between now and December 31, 2026 for 6 nights or more and receive a FREE 4-door rental car from top providers--Hertz, Alamo, Avis, or Budget. Convenient airport pick-up and...
Professional Design: Ocean View: Private Apartment
Summary:Designed by Twin Islands Interior Design Group - Escape to Big Island and indulge in the tropical paradise of Hawaii with this charming 1 bedroom, 1 bathroom Airbnb property. Enjoy an ocean view from your breezy porch and sleep peacefully in a comfortable...
❤️PiH❤️SPARKLING WATERS ★ Hilton Passes ★ Large Pool & Waterfall Spa ★
Brought to you by Paradise in Hawaii Luxury Homes.Welcome to the newest elegant home, Sparkling Waters, in our Hawaiian Luxury Collection.Sparkling Waters is a wonderful new large single level 4 bedroom, 3 bathroom home. This home has one of our largest private heated...
Napili 1st-level serene and peaceful retreat
Welcome to Napili Shores E135, a stunning ground-level 1 bedroom 1 bathroom condo nestled in the heart of Napili featuring a garden view and split AC system. This condo sleeps up to 4 guests. This resort does not have elevators. The living room is enhanced by an...