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.
Kapalua Bay Villa 26G2 Gold Oceanfront 1 Bedroom
- Villa closest to Oneloa Beach- One level condo with 17 stairs between parking and front door- Travertine tile floors in living room, dining room, kitchen and bathroom and carpet in bedroom- Contemporary galley kitchen with granite counters and stainless steel...
Adorable with Ocean View at The Cliffs 4209 1/BD 2/BTH
North Shore Living at it's finest! Soak up the Hawaiian sun and salty ocean breezes from this thoughtfully remodeled 1 bedroom, 2 bath condo at The Cliffs in Princeville. With a spacious layout, this airy second floor unit offers a partial ocean view and is just a short...
Discover Your Paradise at Royal Mauian 104
Welcome to Royal Mauian 104, where luxury meets the beauty of Maui’s coastline. Nestled on the ground floor of the prestigious Royal Mauian complex, this modern 2-bedroom, 2-bathroom condo offers the perfect blend of style and comfort. With direct access to manicured...
Newly renovated guest house with lush landscaping & gazebo
Honolulu HideawayOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Nestled in the heart of Honolulu, this charming guest house offers a tranquil retreat surrounded by lush landscaping...
Hawaiian House With Ocean View
THIS PROPERTY CANNOT BE RENTED FOR LESS THAN 31 DAYSMonthly rent includes utilities (water, electric, wifi, landscaping) for rental periods of 1-3. Monthly rentals of 3 months or more are utilities included with a cap on electric. Rents under 6 months are subject to a...
Remodeled ground floor Kihei studio with AC across from beach
Welcome to Kihei Bay Surf 140. This completely remodeled ground floor studio has all the comforts of home. Feel right at home in this quaint coastal styled condo that can accommodate 3 people with the window AC unit, sofa sleeper, and ceiling fan. Pool, spa and tennis...
50 steps away from Maui's best beach, furnished with luxury details
Welcome to your perfect getaway in Maui! This exquisite 2-bedroom, 2-bathroom apartment, nestled on the 2nd floor of Pacific Shores complex, elevator-accessible building, offers 745 sqft of living space. Furnished with high-end furnishings, this apartment comes with 3...
Lanikai Hale - Elegant Kauai Villa + Guest House | Stunning Ocean Views | Private Pool + Hot Tub
Summary:Discover Lanikai Hale, a luxurious, family-friendly retreat on the south short of Kauai. This peaceful villa includes access to a detached ohana (guest house) and comfortably accommodates up to 10 guests. Enjoy a private pool, hot tub, fire pit, outdoor kitchen...
Million Dollar View of Maalaea Coastline - Island Breeze
Experience the charm of Island Breeze, it's a delightful 2 bed/2bath condo, mere steps from the clear, azure waters of Ma’alaea Bay. Gaze at the sunrise over Haleakala from your own private lanai (two lanai's), while whales frolic in the bay and turtles gracefully...
Modern Oasis w/Hot Tub, 5 min walk to Anini Beach
A stylish reimagining of our ever-popular Coconut Hut. This perfectly positioned gem sits in a secluded park-like paradise within a 5-minute walk to the idyllic Anini beach. With new construction, the house contains hardwood floors, whole house water filtration, AC in...
Rainforest Stay w/ Hot Tub < 3 Mi to Nat'l Park!
From exploring active volcanoes to strolling black sand beaches, this modern 1-bed, 1-bath Volcano home is your base for an unforgettable island adventure. The eco-conscious hosted vacation rental is tucked away in the tranquility of the rainforest, yet only 3 miles...
North Shore Turtle Bay Hideoutn - Kuilima Estates East
BRAND NEW RENOVATION. This unit backs up to the world famous Fazio golf courses with a beautiful view of the 18th hole from the relaxing lanai. Just a five-minute walk from the beaches at Turtle Bay Resort and access to miles of walking and biking trails. Turtle Bay is...
NEW PROMO! Ocean & Golf Views | AC | Lanai
Welcome to Living on Island Time — your private retreat on the Kona Country Club Golf Course with sweeping ocean and fairway views. Watch sunsets over the Pacific right from your lanai, just minutes from beaches, snorkeling, and Keauhou Bay adventures.🏝️ The SpaceThis...
Whitewater and Anini Reef Ocean Views fully airconditioned
This recently and completely remodeled, sun-lit and spacious 2-bedroom, 2-bath condo at The Point at Alii Kai (Unit 5-302) welcomes your group to an unforgettable vacation in Princeville, where you'll face jaw-dropping, direct Pacific Ocean views on Kauai’s North Shore....
Luxurious golfside condo with ocean and golf course views
Emmalani Court at Princeville #321Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Experience luxury and relaxation at this stunning condo located in Princeville, Hawaii, overlooking...
Turtle Bay Villa G318
New Year’s Special: 25% OFF Your StayValid for stays January–March 2026. Book now!Welcome to Villa 318, one of the most spacious and luxurious properties at Ocean Villas and Turtle Bay. Nestled on Oahu's stunning North Shore, this tropical retreat is the ideal escape...
Family Suite #1 - Two rooms w/ shared hot tub, Family suite # 1 - Ulu Retreat + A'ali'i Sunset Suite
Immerse in tranquility at our Ohia retreat with two serene rooms, each with its own private lanai for enjoying nature's symphony. Indulge in the comfort of 14-inch memory foam mattresses and flat-screen TVs. The courtyard, a blend of open skies and cozy corners,...
Poolside Tropical Paradise Oasis
Escape to paradise and indulge in the serene ambiance of Maui Kamaole M-101, 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...
Modern ocean view suite walking distance to the coolest beach town in Maui
Mangolani Inn is a refreshing alternative to Maui's mega resorts. Live a more like a local by staying in our luxurious award winning tropical sanctuary walking distance from the coolest little beach town in Maui. The Ocean View our newest premier studio on property is...
10th floor partial ocean view studio @ Royal Kahana Resort
Welcome to Royal Kahana 1019. This 10th floor studio offers a partial ocean view. This unit is tastefully appointed with classic Hawaiian decor. The studio features a king size bed. Keep cool year round with central AC & ceiling fans throughout. Enjoy beautiful views...
Perfect for Large Group Stays ~ Kona Forest House
Tucked away in Kona’s misty cloud forest, this spacious 5-bedroom mountain retreat is your peaceful escape from the crowds. Located just minutes from town yet worlds away in feeling, you’ll enjoy cool breezes, sunset skies, lush gardens, and the soulful quiet of the...
KONA CLOUD FOREST GUEST HOUSE~3 Bedrooms~
This two-story 3 bedroom home is nestled among the native forestry on the slopes of Hualalai with both mountain and ocean views. Just seven miles and a 15 minute drive to the heart of Kona town and and 14 minute drive from Kona International Airport. Nearby is Pa’ina...
10th floor Oceanview studio @ Royal Kahana Resort
Welcome to Royal Kahana 1004. This 10th floor studio offers ocean & surrounding island views. Tastefully decorated with classic tropical decor. This studio features a king size bed & a twin sleeper sofa, accommodating 3 guests. The updated kitchen & bathroom features...
Pili Mai Family Fun Condo, AC, Game Room, 2 Bedroom, 2.5 Bath, Sleeps 6
FAMILY FUN at Pili Mai, 2br + Game room (bumper pool, poker table, classic video game console, board games, piano, masks and snorkels, beach chairs, croquet, bocce ball, spike ball, and small yard for the kids to play) 2.5 bath, sleeps 6, no stairs, back yard lawn....
Maui Resort Rentals: Honua Kai Konea 338 – Luxurious 1BR Suite w/ Upgraded Interior and Tranquil, Private Location
Konea 338 is a luxurious one-bedroom suite that offers glimpses of the Pacific Ocean and Honua Kai's lush grounds. Enjoy relaxing in the suite's upgraded interior or on the spacious lanai because this suite has one of the most tranquil, private locations in the entire...
Hilton Pool Pass incl - Spacious & Relaxing Resort Gem ~ View ~ Pool ~ Gym
Hilton Pool Pass Valid for stays in 2026. Maximum 6 persons per pass (children under the age of 5 are not counted towards the 6 person max). Use of the Hilton Waikoloa Pass is valid from 4 pm on your arrival date and 10 am on your departure date. The pass and...
Cozy cottage nestled on our 5 acre Organic fruit farm
The farm cottage is set at the top of our 5 acre exotic fruit farm. Enjoy your stay by touring the property and relaxing in our cozy home away from home. The cottage is equipt with everything you'll need without the clutter. From the living room, enjoy a view of the...
Maui Kamaole M207! Spacious 2 bdrm with A/C
Escape to paradise at this exquisite Maui Kamaole condo, where luxury meets island charm. This spacious two-bedroom, two-bath retreat boasts a soothing ambiance with its beachy décor, beautiful blue hues, and local art prints that bring the spirit of aloha indoors. The...
Ocean View Large Lanai Kamaole Sands
Hosted by VacaMauiLuxurious Condo at Kamaole Sands: Your Perfect Maui Getaway!Welcome to Kamaole Sands, your ultimate destination for a dream vacation in Maui! Our exquisite condo, located in Building #8, Unit #411, offers everything you need for a memorable stay....
Ocean Views | Polo Beach Club Ground Floor Condo | Walk to Beach, Private Patio
Summary:Escape to paradise at this ground-floor condo at the exclusive Polo Beach Club. Enjoy stunning ocean views, lush gardens and direct access to Wailea’s premier swimming beach. The “endless lanai” allows you to step straight onto the pool, beach or scenic...
Waterfalling Estate – Iconic Oceanfront Luxury on the Big Island
Waterfalling Estate is an oceanfront compound unlike any other on the Big Island. Nestled clifftop along the breathtaking Hamakua Coast, this hideaway boasts a private 85-foot waterfall, an Olympic pool featuring a two-story waterslide, spa, fully loaded custom gym,...
#37 - Stunning Unit with Ocean View
This condo sits OCEANFRONT on the Sea Mountain Resort at Punalu'u Black Sand Beach. It is a spacious one-bedroom unit, fully furnished with laminate and ceramic tile floors throughout. The uniqueness of this Polynesian style condo with a modern flair is that it is a...
Coconut Plantation by AvantStay | Resort Access, 0.4mi Walk to Beach!
Please note that this home is available for 28+ night stays only.Aloha from Coconut Plantation! Immerse yourself in the island lifestyle at this stunning two-story condo, surrounded by swaying palm trees and lush tropical landscaping. With 4 bedrooms and 3 full...
Ho’okipa Hideaway - North Shore, Walk to Cafe
This North Shore Maui Hideaway has its own private entrance, a charming private garden, cozy queen bed and off-street parking for one car. An attached covered and enclosed screened porch with two overstuffed lounge chairs looks out onto the beautiful private and gated...
Fairway Villas At Waikoloa Beach Resort#I24: Gorgeous Top Floor 2 bedr/2 Bath
Welcome to your paradise retreat tucked away in a serene enclave of Fairway Villas at Waikoloa Beach. This villa offers a haven where you and your guests can unwind amidst gentle breezes and breathtaking views. This clean and attractive villa has attractive decor &...
Gorgeous Ocean View! Steps to Beach! Centrally located, full kitchen & more!
Waikiki Shore #712 – 2161 Kalia Rd.Waikiki Shore is the only condo in Waikiki where you can step directly from the building onto the sand of Waikiki Beach!You'll be mesmerized by the incredible ocean views from this beautiful Hawaiian feel contemporary. The open concept...
Experience Tropical Tranquility: Luxury Studio Home in Hilo!
Experience convenient and comfortable living staying at our studio in our newly built duplex home. Located centrally in Hilo. You will be just 3 miles from Hilo airport, Liliuokalani Park and Garden, Carlsmith Beach Park, and many other popular attractions and...
(4102/03) 2Br Ground Floor Hanalei Bay Resort, Ocean View, Pool, Tennis
Welcome to Hanalei Bay Resort unit 4102/4103. A ground floor unit with stunning views of Hanalei Bay and the surrounding Bali Hai Mountains. This beautiful unit has 2 bedrooms, one with a King size bed and large en-suite bathroom with a shower to rinse off after a day...
(4101/02/03) 3Br Ground Floor Hanalei Bay Resort, Ocean View, Pool, Tennis
Welcome to Hanalei Bay Resort unit 4101/4102/4103. A ground floor unit with stunning views of Hanalei Bay and the surrounding Bali Hai Mountains. This beautiful unit has 3 bedrooms, 2 of which have King size beds and two large bathrooms with showers to rinse off after a...
Ala Moana Hotel 13th FL R0 Studio - 2Double Beds 4Person
NEWLY RENOVATED 13th floor with Partial Ocean ViewCozy Hotel Studio | 2 Beds | 1 Bath | Sleeps 4 Stay in the heart of paradise! This bright and comfy studio is perfect for friends or family, with 2 beds, 1 bath, and space for up to 4 guests. Just steps from Ala Moana...
Charming, Romantic Beach Cottage at Anini Beach! TVNC 1361
Tucked beneath swaying palms and just steps from the gentle turquoise waters of Anini Beach, this enchanting one-bedroom cottage is pure island charm. With its vintage flair and dreamy, movie-set vibes, it’s the perfect hideaway for romantic retreats, solo escapes, or...
Kihei Holiday Stunning Ocean View #309 2bd/1ba condo, 1 min walk to the ocean.
***Notice (July 2025) regarding Short Term Rentals on Maui: Kihei Holiday Condominium is legally zoned (H-1/H-M) for short term vacation rentals and is not affected by the new rules in Maui County for many other properties! Your booking is safe with us!!!Maui Ocean...
Chic & Upscale Waikiki Beach Ocean View w/ Parking
Aloha from Midway Vacations! Our team of local hospitality experts is dedicated to turning your Hawaiian getaway into a reality. When you stay at one of our properties, you can count on a professionally cleaned and meticulously maintained experience. We're even...
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!'Escape to luxury in this stunning 2-bedroom condo nestled within the prestigious Mauna Lani Resort on...
Luxe Private Princeville Retreat Near Hanalei Bay!
Delight in the very best of Kauai from the comfort & convenience of this spacious private retreat! Perfectly situated in the heart of Princeville just minutes to Hanalei Bay, enjoy relaxing on Anini Beach, a round of golf at Makai Golf Club & luxury resorts simply a...
Oceanfront condo with resort amenities, stunning views, and top-notch comfort
Ali'i Cove Y1Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Experience luxury living in this stunning condo located in the exclusive Ali'i Cove Condominium complex in Kailua-Kona,...
Elegant 3BR Pili Mai 12A w/ Pool, Golf Course Views & Modern Amenities
Welcome to Pili Mai 12A by Gather, the perfect three-bedroom, three-bathroom condo in Koloa. This ground-floor condo, alongside the picturesque Kiahuna Golf Course, offers garden views and a newly designed layout with central air conditioning. Each of the three...
Spectacular Oceanfront Luxury- Between Kam1 & Kam2 Beaches - Royal Mauian #511
Royal Mauian #511 – Upgraded Oceanfront ComfortRoyal Mauian #511 offers a beautifully upgraded retreat in one of South Kihei’s most desirable oceanfront properties. This two-bedroom, two-bathroom condo combines modern design, stylish finishes, and the comforts of...
🏖️Walk to Beach, Restaurants, Shopping | Concierge Included | vrKCV
vrKCV - Kolea 15L, Professionally Managed by Kona Coast VacationsWelcome to Kolea 15LA luxurious haven within the renowned Kolea community, located in the heart of Waikoloa Beach Resort on the stunning South Kohala coast. This exclusive residential gem offers direct...
❤️PiH❤️ BIG ISLAND OASIS ★ Family Oasis★Free Hilton Passes ★ Bikes & Ping Pong★
Big Island Oasis brought to you by Paradise in Hawaii Luxury HomesWelcome to our Big Island Oasis at KaMilo, a spacious and beautifully appointed four-bedroom retreat on the Big Island of Hawaii. With room for up to ten guests, this home provides the perfect setting for...