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.
Honu Awa - Princeville Kauai Oceanfront Vacation Rental Home
Enjoy an amazing retreat at Honu Awa, meaning Turtle Cove in Hawaiian. This upscale home sits on a dramatic bluff overlooking the north shore surf, a mesmerizing reef, and endless Pacific waters.This stunning villa boasts three ocean-view bedrooms with en suite...
KBM Resorts | FREE CAR | Mahana | Oceanfront | 2-Bedroom Penthouse with Gorgeous Sunsets! MAH-1211
** 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...
Hale Kai #116 Oceanfront Condo, just steps to the beach, pool and BBQ!
Fully remodeled first floor direct oceanfront condo, just steps from the pool, beach, and BBQ. The Hale Kai has a small quiet feel, that has guests returning year after year, "Hale Kai", your home by the sea. Experience amazing views of Molokai and Lanai and enjoy...
Kukui'ula Cottage #29: Modern Plantation-Style Home with Pool
New home construction next door started in Jan 2022This luxury Kauai vacation rental is located in the luxury resort community of Kukuiula. This fabulous new home has lovely distant ocean views from both the main living area and the upstairs master suite and private...
Ocean views w/ breezes! Large Lanai, Kitchen, 2 bedroom - beautiful neighborhood
Newly renovated Fully equipped Kitchen – new refrigerator, range, dishwasher and microwave. Many amenities. Hawaiian style outdoor living and dining room in 700 sq. ft. Lanai with 4 ceiling fans to assist the ocean breezes. • 2 Bedrooms each with a queen size bed...
Spacious, Private Villa Ideal For Extended Or Multiple Family Rendezvous
This stunning 10,000 square foot, slate and mahogany floored, 7-bedroom open air Villa is your own private paradise. Enter the expansive foyer through the beautiful etched glass double doors to step down into the 2 1/2 story living room capped with a traditional...
Turtle Bay Resort Oceanfront Villa - 3 Bedroom
***This is the most luxurious stay you can get on the North Shore of Oahu! Our amazing Ocean Villa is one of the only two villas located in the whole Ocean Villa Complex that allows you to have Ocean Views from ALL BEDROOMS. Unlike most houses on the North Shore that...
Papakea L301 - Direct Oceanfront Luxurious Corner 1B/1B, Newly Renovated, AC!
Oceanfront corner condo with panoramic views from Lanai to Molokai - unobstructed sunset views any time of the year. At dusk, tiki torches light the path to the water where the sun sets between the neighbor isles of Lanai and Molokai. Located on the third floor, this...
Tropical paradise with pools, hot tub, BBQ, lanai, washer/dryer, AC
Plantation Hale C1Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'This well-appointed condo has everything you need for a breezy and tranquil stay! This spacious, end-unit condo is...
Charming 2-bedroom bungalow with AC and WiFi in Kailua-Kona
Stay here at Hale Kai Hideaways, Bungalow C, right on Alii drive located in the center of Kona town. Across from Turtles beach (short walk over rocks) and a beach access to the ocean. A quick walk to Alii Garden's Marketplace with Shaka Taco's, local coffee and...
Hale Kupa'a: Charming Island Villa w/ Beach Nearby
Hale Kupa'a—this delightfully situated house on Poipu Kai’s scenic, super-convenient Green Belt walkway—was completely remodeled in summer 2021, and the exquisite attention to detail is evident in every light, bright, charming room. Leafy green views fill the...
Owner Direct - Check our 160 Reviews! - Elua Village 701, Luxury 2BR, Ocean View
Aloha! We are Julie and Randy and welcome to our home! We want you to enjoy the fantastic ocean views and luxury of our 2-bedroom, 2-bathroom condo in Wailea Elua Village - a gated, 24-acre, oceanfront community on beautiful Ulua Beach in Maui.All open dates through the...
Wailea Ekahi Village 30D - 1 Bedroom Ocean View Condo
Nestled in the prestigious Wailea Ekahi Village, condo 30D is an exquisitely decorated island-inspired vacation rental that offers a perfect blend of luxury and comfort with breathtaking ocean views. The lanai provides an idyllic setting for outdoor dining or morning...
Ocean view 2 bed/2bath Kaanapali Shores gem
Welcome to Kaanapali Shores 423. This beautifully positioned 4th floor ocean view 2 bed/2 bath condo features newly upgraded central AC, fully equipped kitchen with granite counter tops, in unit washer/dryer, & more. This condo can accommodate 6 people. Admire the...
Relax and Rejuvenate in the Heart of Kona. Minutes walk to town!
Condominium pool will be closed all of October due to renovations. BBQ’s will be open. Simple 1 bedroom/2 bathroom condo for rent. Sleeps two comfortably but can sleep four. Unit is fully furnished, with two lanai's, washer/dryer, television, Wi-Fi, and 1 garage space...
Includes Mauna Lani Beach Club Pass. 801 Kulalani
Kulalani 801. Includes Mauna Lani Beach Club Pass Please scroll down for detailed informationAloha!We’re excited to share that you this property is being beautifully updated with brand-new Restoration Hardware furnishings and refreshed interiors. The remodel is...
White Sands Village#121: Beachfront Complex, AC, Spacious Unit!
Escape to Paradise at White Sands Village in Kailua Kona! Unit#121 has all the essentials one needs for a Beachfront Vacation. Welcome to your perfect Hawaiian getaway! Nestled in the heart of Kailua Kona, this 2-bedroom, 2-bathroom unit at White Sands Village offers a...
100-4 Island living at its best!!
Puamana 100-4 is a beautifully remodeled 3-bedroom, 4-bathroom townhome offering partial ocean views in a prime location, directly across from the beach access. Unfortunately, the historic clubhouse and some amenities were lost to the fire. Despite this, Puamana still...
Maui Kamaole A-206 - Prime Location, Stunning Renovation, Large Lanai, Split AC!
Welcome to Maui Kamaole A-206, a stunning 2-bedroom condo nestled in the heart of South Kihei, Hawaii. This beautifully appointed retreat offers a perfect blend of comfort and style, making it an ideal getaway for families or couples seeking a slice of paradise.With a...
2/2 Oceanview Modern Resort Vistas
Summary:Spacious and elegant. Completely remodeled in March 2024, no expense was spared to create our gorgeous oceanfront oasis. This two-bedroom, two-bathroom condo features luxurious touches paired with oceanfront serenity. Located in sunny Kihei, all of Maui is...
In the center of it all!
Maui at it finest! Fantastic oceanviews where you can watch whales from your balcony and visit sea turtles on the private beach area. This centrally located property is in a quiet area on Maui, but everything is just minutes away!Maui's beautiful southern 7 Mile beach...
Beach/Oceanfront, AC! Pool, Gym, Steps to Beach!
Welcome to The Surfing Turtle Poipu! Updates: We have a brand new beautiful roof as of April! We also have newly installed mini split AC in all three rooms! Come visit us this fall and winter and experience the perfect tropical escape on Kauai at our beachfront vacation...
Jewel Villa in Ko Olina Resort
This newly renovated, luxurious Villa is nestled in the quiet resort of Ko Olina. This Villa has 3 bedrooms and can sleep up to 6 guests. Choose to spend your days on the Ko Olina Championship golf course, one of the four lagoons on the beach, or eat at any of the...
Fabulous Ocean Views with Mauna Kea Resort Access
Situated within the Mauna Kea Resort, this home is close to two championship golf courses: the newly renovated Mauna Kea Golf Course and Hapuna Golf Course. Furnished in a natural tropical motif with high beam ceilings and lots of windows, this spacious Fairways South...
Quiet Paradise on Bay w/Aircon
A true Hawaiian-style vacation rental makes you feel welcome in this fully equipped family home. Just steps to the magical blue waters of Kealakekua Bay, you'll be able to swim, snorkel, and paddle practically in your front yard. With a peekaboo ocean view you can see...
Hale Kahakai - Oceanfront Retreat - Direct Beach Access - 30 Day Rental
Important Notice: This property is available for rental with a minimum stay of 90 consecutive days. Rental prices remain fixed and are not subject to reduction based on the length of stay.Welcome to Hale Kahakai! This exquisite single-family oceanfront retreat is...
Beachside Kailua AC 3min walk to beach! Inquire for available dates!
THIS PROPERTY IS A LEGAL SHORT TERM RENTALCONTACT HOST/RESERVATIONS & DETAILSThis airy, spacious four bedroom Kailua beachside vacation rental home with AC provides the essence of tropical Hawaiian living. Remodeled kitchen and bath(s) finish off this stunning home....
Coconut Plantation 1158-1: Spacious 3BR with Modern Kitchen & Private Lanais
Welcome to Coconut Plantation 1158-1 by Gather, a beautifully updated two-story retreat in the heart of Ko Olina Resort. Blending island charm with contemporary upgrades, this 3-bedroom, 2.5-bath home offers 1,784 square feet of stylish living space and private lanais...
Hanalei Bay RESORT 2312, Amazing Views wKitchen 10 Stars Reviews!!!
NEWLY REMODELED Well maintained Studio!!! One of the best locations on Kauai’s lush North Shore fronting the white sands of Hanalei Bay with amazing views of tropical sunsets, lush green mountains and the sparkling blue waters of the Pacific Ocean. These Kauai condos...
Kauai's Sunny Poipu Beach Estates! A Beautiful Plantation Style home sleeps 8.
The residence is designed as a gathering place with an open, airy living area ideal for entertainment of all kinds. The kitchen features stainless appliances, a generous island and lots of counter and storage space resulting in an excellent setting for creating...
Mauna Lani Golf Villas C1: Spacious Condo w/Views Golf Course Views, A/C, & Pool
Situated in a superior end-unit location on the 10th fairway of the famed Francis H. I'i Brown South Course at Mauna Lani, recently-renovated Golf Villas C1 offers a one-of-a-kind vacation experience. Watch the sun rise over Mauna Kea to the east of this exceptional...
Ma'alaea Surf Unit E3-1 BR Ground Floor Beachfront Condo, Wifi, AC, Pool, TV
Ma’alaea Surf, Unit E3 is a conveniently located, beautifully appointed, expansive ground floor apartment near the large pool with fabulous ocean and sunset views. This unit features AC, Wi-Fi, TV, kitchen, 2 pools, tennis and pickleball courts, convenient parking,...
Living Aloha: A Quiet Condo w/ Step-Free Access!
Escape to the beaches and clear blue waters of the Big Island in this 2-bedroom, 2-bath Kailua-Kona vacation rental. This condo features king beds, a living space filled with natural light, a TV, tile floors, and a private lanai overlooking the 18th-hole golf course...
🌴 Ocean Front * Premium Luxury Condo * Mahana Kaanapali 🌴
Upon entering this west Maui condo, you are stopped in your tracks. You can hardly believe what you are seeing.First, there is the view. Eight-foot-high and stretching along the entire ocean-facing front of the unit, the floor-to-ceiling windows are filled with a...
Napili Bay Perfection #201, Top Floor, Corner Unit, On The Beach! Specials!
Stay right on Napili Bay beach, considered by many one of the top beaches in the world. This upgraded and remodeled studio will help you feel right at home when it’s finally time to relax after your all day activities. Along with being directly on the beach, you can...
Beautiful Beachfront Corner Unit Condo with wraparound lanai
30 day minimum, contact owner for additional details. Secluded beach, the Pacific surf, beautiful sunsets, mountains, whales, turtles... Enjoy them all from your spacious (nearly 400 sf) covered lanai. Swim in the salt water pool, soak in the hot tub, lounge on the...
Oceanfront luxury 3bd condo on Baby Beach
Puunoa Beach Estates is one of Lahaina's best-kept secrets. This exclusive 10-unit gated boutique resort is nestled on Baby Beach, otherwise known as Puunoa Point and is famous for soft white sand and tranquil waters. The outer reef protects this point from the waves...
Steps to beach! Gorgeous renovated partial ocean view condo at Waikiki Shore!
Waikiki Shore #515 – 2161 Kalia Rd.NEW TO OUR INVENTORY! Waikiki Shore is the only condo in Waikiki where you can step directly from the building onto the sands of Waikiki Beach! This exquisitely remodeled (2023) 5th-floor beachfront studio is a favorite with return...
Sparkling 1 BR condo in central Kihei w/AC. Walk to the beach!
Located in the heart of central Kihei, Kihei Akahi C-517 is a dream. Freshly updated with custom cabinets, super quiet split AC and a king bed, this condo is your perfect home away from home. Your place comes equipped with a fully-stocked kitchen, in-unit washer and...
West Side Westy - 1985 VW Westfalia
This 1985 VW Westfalia has everything you need to explore the island your way. This classic bus seats & sleeps up to 4 adults in its 2 fold out beds. It also includes a kitchenette with sink, cooler, and two burner stove. There are direct hookups for electricity &...
Luxury Resort • Ocean View • Golf Membership
Summary:Hali’i Kai in Waikoloa Beach Resort • 69-1033 Nawahine Place #10A • 5★ RatedHali’i Kai 10A is a stunning oceanfront condominium in the highly sought-after gated Waikoloa Beach Resort. This family-friendly 2-bedroom, 2-bathroom unit comfortably...
Perch - Maui condo: Pool, beach access, daily tranquility on lanai – an indulgent escape.
Discover your ideal Maui retreat in this cozy space with elegant tiles, sunny windows, and a spacious private patio. Explore lush surroundings with amenities like a pool, hot tub, picnic area, and BBQ facilities. Plus, enjoy easy access to the sun-kissed shores of Maui...
Steps to Napili/Kapalua Bay! Napili Gardens 3BR
Summary:✨ Welcome to Where Maui Magic Meets Comfort ✨Experience Luana, the Hawaiian practice of relaxing, enjoying, and finding happiness. Just 200 steps from the inviting turquoise waters of Napili Bay, this luxurious 3BR/2.5BA townhome at the Residences at Napili...
Leipiha ke Aloha - Steps Away from Poipu Beach with A/C!
Light, bright and airy perfectly describe Leipiha ke Aloha. And just like a lei, which has no ending, you won’t want your vacation at this home to ever come to an end! You’ll love having the ocean and beach so close to you while enjoying the comforts and ambiance of...
April Special 199/night! Honomū Haven - At the Gateway to Akaka Falls 🏝
Honomū Haven is the perfect Big Island escape for families and groups - just 20 minutes from Hilo and 5 minutes from ʻAkaka Falls. This spacious 5-bedroom home features a lush yard, screened patio, and a balcony with views of Mauna Kea. Whether you’re relaxing,...
Kona Makai#1-102: Nearly Oceanfront, Ground Floor, with AC & Newly Remodeled!
Unit 1-102 is located in the highly desired building 1 in the gorgeous oceanfront complex of Kona Makai.With stunning ocean views from both the Lanai and Bedroom, this unit is literally steps away from the ocean.This ground floor unit is well equipped with a spacious...
Skyline-Lagoon and Fireworks Magic from the Ilikai w/Top-Tier Amenities
Book with confidence! This property is professionally managed by Ali'i Beach Rentals, an award-winning property management company.ILIKAI BUILDING NOTICE: October 25, 2025Spalling repairs and full exterior painting of the building in effect. Please be advised: Balcony...
Tiki Tiki - A Gorgeous Boho Beach Hideaway!
Fall in ALOHA with Tiki Tiki!! This special studio is truly a piece of Paradise!A magical retreat that will have you feeling zen & refreshed. Tiki Tiki is the perfect home for honeymooners, girlfriend getaways, or any adults looking for a tropical stay in the the heart...
The Mai Tai Manor with unobstructed views of the ocean!
This 4 bedroom with separate ohana used as 4th bedroom, 3 bath home have unobstructed views of the ocean!! Very close to beaches and shops. Home can sleep (8 guests!)Come to The Big Island of Hawaii and enjoy your well-deserved vacation in our...
LAST MINUTE AVAILABILITY IN APRIL $ 100/Night DISCOUNT! 2 BR Ma'alaea Surf B4
Located just steps from the shore on Sugar Beach in beautiful Ma'alaea Surf Resort, this remodelled two-bedroom, two bathroom ground floor condo is your perfect vacation hideaway. The unit was taken to studs and completely rebuilt in late 2022 and every element was...