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 full-view of Maalaea Bay. Lanai overlooks pool. King size bed.
THIS CONDO IS SIMPLY ONE OF THE BEST IN THIS METICULOUSLY MAINTAINED DEVELOPMENT We have just finished extensive re-modeling, including new 18x18 Italian floor tile throughout, new kitchen and bath cabinets with granite countertops, and brand new teak plantation style...
Ekahi Village 44C - Beautifully appointed Ocean View Condo mins from the beach
Wailea Ekahi Village 44C is a lovely and romantic two-story townhouse. The downstairs lanai is surrounded by lush gardens with the sweet aroma of native Hawaiian flora. The upstairs lanai affords a panoramic ocean view and breathtaking sunsets.This condo is a mere 4...
Central, Cozy 2 BR (Heart of Kapaa)
*** Receive SPECIAL weekly discount *** Stay in charming Kapa'a, a central spot in Kauai. This modern 2 BR/1 BA condo is a few steps away from the oceanside, shops, & restaurants!Excellent value. Includes a fully stocked kitchen, parking, W/D, A/C unit (living room)....
Sugar Beach Resort Condo w/ Shared Grill, Shared Pool/Hot tub-Beach Lovers Dream
Sugar Beach Resort 507Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Join the many guests who return each year to Maui's Sugar Beach Resort to enjoy the spectacular views from this...
Private and Quiet Peaceful Poipu Beach Oceanfront Condo
Enjoy our brand new oceanfront deck area, just completed late 2014. Escape to this peaceful 2 bedroom retreat and let the sounds of crashing waves lull you to sleep. Kick off your shoes Hawaiian style and enjoy this perfect private setting on a bluff overlooking the...
Ocean-Marina Yacht Views Condo Steps to the Beach w/Full Kitchen & Free WiFi
Book with confidence! This property is professionally managed by Ali'i Beach Rentals, an award-winning property management company.July 11, 2025ILIKAI MARINA NOTICE — Spalling Work UpdateSpalling repair on the Ocean/Marina-facing side is nearing completion, but...
Lush tropic stay with a lanai, washer/dryer, shared pool, hot tub, & game room
Greens At Waikoloa J101Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Aloha paradise! During your stay at Greens At Waikoloa, enjoy scenic views of Hawaii's natural flora and fauna,...
Oceanfront Paradise with private lanai overlooking Kailua Bay
Sea Village Resort sits right on the sea wall. Located on prestigious Alii Drive. The well kept grounds surround a newly renovated pool, spa, and barbeque . Walk to town for a morning cup of the famous Kona coffee, shopping and evening ocean front dining. Big Island...
Updated Papakea oceanview condo, & all the amenitiesn
Welcome to Papakea E-206. This beautifully updated ocean view condo is the perfect island getaway. This unit features all the comforts & amenities you'll need to feel right at home. Fully equipped kitchen, oversize fans in every room, split AC unit in living room &...
Maui Sunset Vacation Rentals condo suite A515
A-515 is the best. Just fantastic location and awesome views of the pool, ocean, palms in the tropical oasis of Maui Sunset. Premium renovations top off the experience, although you'll spend most of your time out on the private view deck. Large private condominium...
Sandpiper 133B - updated and renovated studio in Princeville
Clean, modern, studio with kitchenette. Completely renovated December 2018 - everything is new including floors, cabinets, interior paint, shower, vanity, fixtures, ceiling fan, furniture... There is a comfortable queen bed and an air mattress (twin or queen) can be...
Maui Resort Rentals: Honua Kai Konea 610 – 6th Floor 1BR w/ Partial Ocean & Mountain Views
Konea 610 is a luxurious 6th floor one bedroom partial ocean view suite that offers epic sunrise and frequent rainbow views. This 1BR/1BA suite offers expansive vistas of the West Maui Mountains coupled with glimpses of the Pacific. The suite is ideally suited for small...
OCEANFRONT RESORT - Spring Pricing! Kihei Sands Beachfront Condos -B13
Our 2-bedroom/2-bath townhouse style home with ocean view is on the 2nd level (no elevator) at Kihei Sands Condominiums. It is perfect for a ROMANTIC getaway for two couples - or if you want to include the kids or more friends, pull out the queen sleeper sofa to...
Mauna Lani 3 BR Luxury Villa - Best Value in Mauna Lani!!!
Our villa is furnished in a casual tropical island theme with all new wide plank flooring throughout. This 3 bedroom villa is ideally located, just steps away from the pool. Our Hawaiian style townhouse is very large, has an 10-ft living room ceiling, and has no one...
Kauai Kailani - Steps to Beach Oceanfront Pool - Fully Renovated 2 Bdm Condo
Kauai Kailani a Beautiful Garden View! A 2 Bedroom Condo located along the famous Coconut Coast on Beautiful Kauai East Shore!The Experience: Peaceful in this nicely decorated condo just steps to the beach!And, there is AC in this condo! Sleeps up to 6! King bed, 2 Twin...
Oceanfront IS310 - Charming One Bedroom Maalaea Bay is an Incredible Value
Experience the breathtaking views and serene atmosphere of Island Sands #310. This oceanfront condo offers a stunning panorama of the Kihei coastline and the majestic Haleakala. From December to mid-April, witness the spectacle of Humpback whales birthing their calves...
Kona Coastal Getaway – A Short 5 min Walk from Beach, Shops & Vibrant Ali‘i Dr!
Experience the best of Kona in this bright and inviting retreat! Located within 5 min walk to grocery stores, Historic Ali‘i Drive, downtown, and the pier, this cozy getaway offers the perfect blend of convenience and island charm. Enjoy the airy living space, modern...
Stylish Ocean View Condo Near Waikiki Beach with Free 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...
Beautiful Hali'i Kai Villa in Waikoloa Beach - Recently remodeled!
Welcome to our beautiful two bedroom, two bathroom villa in gorgeous Hali’i Kai. Located in the world-famous Waikoloa Beach Resort, our fully furnished villa will pamper and refresh you with breathtaking views and freshly updated modern conveniences. Fresh paint,...
Waterfront Condo with Resort Pool & Hot Tub - Short Drive to Lahaina
Paki Maui 423Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Welcome to paradise! Kick back on the classic Hawaiian rattan love seat in this two-bedroom, two-bathroom condo and soak...
Spectacular Keauhou Bay Views
Let our 2nd home be your 2nd home! Vacation in the beautiful islands of Hawaii! Our quiet little complex consists of only 48 units on over 4 acres of tropical paradise! From our ground floor unit you can sit back and enjoy the breathtaking views of the sun setting over...
BEACHFRONT RESORT, OCEAN VIEW
Completely updated room as of April 2025!! 3rd floor ocean & pool view. Our condo hotel room offers one of the best views on the property! If a gorgeous well kept resort is what you're looking for, look no further. Enjoy a cup of coffee in your room or lanai admiring...
Considered the Best Location Oceanfront on Maui
The Maui Sunset is located on over 5 acres of ocean front in Kihei, which is considered one of the best locations on the Valley Isle. Kihei is noted for its year round sunshine, balmy trade winds and soothing evening air. It is one of the driest and sunniest areas on...
Hawaiian condo with WiFi, shared pool & hot tub - close to golf, beach
Plantations at Princeville #1312Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'This fabulous, ground-floor condominium offers two large bedroom suites and access to a shared hot tub...
#02 Kawela Kai 495:North Shore Beach Front---Relax & Unwind
LEGAL SHORT-TERM RENTAL! CERTIFICATE:1990/NUC-2056 LICENSE# 90/TVU-0003 TAX MAP KEY: 1-5-7-005:006This home is not affected by the new Honolulu County ban on vacation homes. Make sure when booking your vacation home the property that you are reserving has a Short-Term...
Experience Oceanfront Luxury at Kanai A Nalu 209, a Spacious 2-Bd/2Ba Condo, AC!
Kanai A Nalu 209 is a newly renovated 2-bedroom, 2-bath ocean view condo located in the Kanai A Nalu resort in Maalaea, Maui. This second-floor unit offers stunning south-facing views overlooking the tropical courtyard, pool, and the Pacific Ocean .The condo features...
Peaceful Island Escape Condo with four pools near all the best things in Maui!
1 Bedroom + 1 Sofa bed, 1 Bath Maui Condo that Sleeps 4 - That could be your comfortable & fun home-away-from-home while in Maui!Welcome to the description of our condo at Wailea Ekahi, a privately owned, beautifully landscaped, condominium community located on...
KKSR#3 DIRECT OCEANFRONT TOWNHOME! Walk to the Beach! Superb Location! AC!
Welcome to this incredible oceanfront townhome in the heart of historic Keauhou! This 2-bed, 2-bath townhome offers the perfect blend of privacy and convenience sleeping a maximum of 4 guests.Air Conditioning now fully installed throughout the condo!With some incredible...
Country Club Villas - Golf, Air Conditioning & Oceanview
Summary:Country Club Villas are located in an exquisite setting with panoramic ocean views on the 17th and 18th fairways of the Kona Country Club. Maximum occupancy strictly enforced in accordance with local ordinances.The Space:The tropically landscaped property is...
Wailea Serenity | 2 Bed, 2 Bath
This Grand Champions condo (#15 in building #2) is located in the heart of beautiful Wailea, a short walk to the beach, and in the middle of the renowned Blue Golf Course. South Maui, with the best weather in the world, is the ideal location for your Island vacation....
KAUAI Poipu Beach Escape to Tropical Paradise!...Beautiful Mountain views!
Beautiful sunny Poipu on the sunny south side of Kauai!This new home is one of the best south shore Kauai locations!For inquiring couples celebrating their honeymoon or anniversary, we are offering a free gift for your special trip by using the code "LOVE”.Also, enjoy...
🏖️Lagoon View | Ground Floor | WIFI | Nicely Upgraded | vrKCV
vrKCV - The Shores at Waikoloa 114, Professionally Managed by Kona Coast VacationsWelcome to Your Hawaiian Oasis!If modern comfort is what you're looking for, look no further. Relax and unwind in your Hawaiian home away from home. As you step inside, a beautiful view of...
Oceanfront condo with ocean view, private washer/dryer, and access to pool
Hololani B504Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Limited time summer discount. Holy whale watching, Batman! Watch spectacular sunsets from the comfort of your lanai at...
🏖️AC | Top Floor Corner Unit | Ocean View | vrKCV
vrKCV - Kona Isle C31, Professionally Managed by Kona Coast Vacations.Welcome to Your Kona Paradise!E Komo Mai! We invite you to enjoy our little piece of paradise. Start your day with a cup of freshly ground Kona coffee on the lanai as you soak in the breathtaking...
East Hawaii - Ocean, Mountains & Waterfalls
It’s your time to visit the magnificent Big Island of Hawaii with its ocean, mountains, waterfalls, beaches, and endless activities. The Umauma Experience Makani Ea Home is your own piece of paradise waiting for you and your family! It’s a cute 2 bedroom with an...
Renovated and clean studio in Waikiki for two with amazing views
Walk to Waikiki beach, convention center, Ala Moana mall, restaurants, shops and many other Waikiki attractions in this newly renovated unit with a queen bed, full bath and kitchenette. The building offers a pool, Jacuzzi, large sun deck, barbecue grills, gym (one time...
Updated Ground-Floor Condo on Golf Course with a Shared Pool, Gym, & Fast WiFi
Waikoloa Fairway Villas D3Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Welcome home to this beautifully-renovated, ground-floor condo located right on the fairway! Sip your Kona...
Waikiki Beach center! Oceanview, Lanai, Free WIFI and Phone. Full Kitchen.
Our recently upgraded vacation rental with great beach and ocean views from your private lanai (balcony) is now available! It is literally a 1-minute walk to the beach!!!It is a nicely furnished studio with new cabinets and granite counters, a full kitchen, and a large...
VI 401 Remodeled OceanFront Condo w Ocean Views Pool
Valley Isle 401 Beautifully Remodeled OceanFront 1Bedroom, 1Bathroom with Amazing Sunset and Ocean Views. Ideal for Whale Watching and Located Minutes From Famous Maui Beaches FREE daily activities included with your stay value up to $570! Complimentary admission, every...
Oceanfront 1bd private lanai & endless ocean view
Welcome to Mahana 804, a beautiful 1-bedroom, 1-bathroom getaway that offers direct ocean views, a washer/dryer, and central A/C located on the 8th floor and can accommodate up to 4 guests. The bedroom features a king-size premium mattress, strategically designed to...
Poipu Oceanview Studio
If you want to maximize your tropical enjoyment, this ocean-view studio offers just that. The exterior wall is all glass with a large slider opening onto a spacious lanai. The sun rises over Prince Kuhio Park warming the lanai for that morning cup of coffee. Enjoy the...
Hale Kamaole 156 Ground floor condo, easy access to best beach on Maui!
Cozy One Bedroom unit with both Ocean and Garden View, overlooking tennis court, close to pool and BBQ. Well appointed living room, with couch and two lazy boys providing comfortable viewing of the very large flat screen TV - especially after a long day in the sun!...
Mana Kai Maui Resort condo with WiFi & W/D access - near everything
Mana Kai Maui Resort 201COur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Swim, lounge, and snorkel at the fabulous Mana Kai Maui Resort, the jewel at the end of one of Maui’s best...
Excellent value - OCEAN VIEW - D112
This freshly 754 square foot condo is just steps from the beach, renovated and a corner-unit offering stunning ocean views! Pack up the cooler and head to the beach or lounge by the pool and soak up the serenity that is Kihei Bay Vista.Relaxing, airy and open, this...
Spacious 4th-floor 2bd condo with new furnishings
Papakea D401 is a 2-bedroom, 1-bathroom condo featuring amenities such as a washer/dryer, vaulted ceilings, and air-conditioning. Located on the fourth floor, this condo can comfortably accommodate up to 7 guests with a King bed in the master bedroom bedroom, a Queen...
🏖️Close to A-Bay | Concierge Included | vrKCV
vrKCV - Waikoloa Colony Villas 303, Professionally Managed by Kona Coast VacationsWelcome to Hale A Ka La (House of the Sun), a serene and private town-home located on the 9th hole of the Waikoloa Beach Golf Course. Enjoy the luxury of home comforts and the convenience...
ALOHA-WAIKIKI OCEAN VIEW LIVING 11
Two short blocks to the World's most famous beach. Wake up and enjoy beautiful ocean views and tropical breezes from your eat-in kitchen or spacious lanai.This is unit is one of our most popular and once you see the ocean views for yourself, you'll know why!!! This unit...
❤️PiH❤️ Ocean Gem Villa ★ Ocean Front ★ Walk to Private Beach Club ★ Bikes
Brought to you by Paradise in Hawaii Luxury Homes.Ocean Gem is a single-level condo with 2 bedrooms located in the prestigious Mauna Lani Point. The home overlooks stunning ocean coastline, the world-renowned Mauna Lani South course and 49 Black Sand Beach. Ocean Gem...
Kaanapali Alii | 166
Welcome to your luxurious sixth-floor retreat at Kaanapali Alii on the stunning island of Maui! Get ready to experience a vacation like no other as you soak in panoramic views of the Pacific Ocean and embrace the serene ambiance of this beautiful condo.As you step into...
Private Oceanfront property w/ Resort Amenities
Direct Ocean Front Condo on Famed Ka’anapali Beach!Many units at Ka’anapali Shores Resort claim to be ocean front. None are as close to the ocean as ground-floor unit 161! The only things separating you from Ka’anapali Beach are floor to ceiling windows and your...