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.
Kailua Beach Luxury Villa – Coastal Elegance on Oahu’s Windward Shore
Welcome to Kailua Beach Villa, a spacious and contemporary oceanfront retreat on Oʻahu’s Eastern Shore. With 5 bedrooms, 5 baths, and 4,000 square feet of airy living space, this private villa blends modern design with barefoot luxury. Step outside to direct beach...
Honua Kai | 4 Free Rental Cars | KBM Resorts | Exceptional Value | 4 Units, 9 Bedrooms | HK ML-1448
** 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...
New Listing | Charming Condo unit 1-219 Steps Away From Beach
Settle into this beautifully appointed spacious condo with all the amenities and extras you will need to have the home away from home feeling. The bedroom offers gorgeous natural lighting, a comfortable King size bed, AC to keep you cool and a large closet for storing...
Marine Surf @20FL Free Parking Renovated /Cal King
NEWLY RENOVATED! 20th floor with great viewFree Parking. Studio unit for 4 with comfy sofa bed Fully equipped kitchen for home-style meals.The unit has a window AC that can be a little noisy. We have provided a tall tower fan to keep you cool and comfortable at night....
Honua Kai | 2 FREE Rental Cars | KBM Resorts | Exceptional Value | 2 Units, 3 Bedrooms | HK ML-1922
** 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...
Steps to the Beach w/ Ocean View - Kamaole Sands 5-304
With an unbelievable view of the expansive ocean, the gentle sway of the surrounding palms, and the sparkling community pool just below, unforgettable moments will be made from the private lanai of this stunning third-floor condo in Kihei! End each day by soaking in the...
Wyndham Bali Hai Villas | Two 2BR/2BA Villas
Summary:This listing is for two 2BR/2BA suites at Club Wyndham Bali Hai Resort in Princeville, HI. Guests will have access to all resort amenities. Each suite sleeps up to 6 guests. - Photos are stock photos provided by the resort. Your suite may vary slightly from the...
Coconut Plantation 1074-1: Luxury Resort Home Easy Walk to Ko Olina Lagoon
Welcome to Coconut Plantation 1074-1 by Gather, a beautifully upgraded four-bedroom, three-bath villa in the coveted Coconut Plantation at Ko Olina Resort. Offering 1,715 square feet across two stories, this furnished home combines resort-style amenities with everyday...
New Listing! Cozy condo with partial ocean views!
Aloha and welcome to your slice of paradise at Kaanapali Shores 309! This beautifully appointed 1-bedroom, 1-bath condo is perched on the 3rd floor of the sought-after Kaanapali Shores Resort, nestled right on the golden coastline of West Maui. Perfect for couples or...
Pool Ocean View. 4 Star Beachfront Resort. Lanai.AC.Restaurant.Pool. Gym.Spa.
About this spaceWelcome to Kauai, the Garden Isle, where local culture meets world-class hospitality. A full service 4 star beachfront resort, escape to paradise at our tropical oasis nestled directly on Nukolii Beach on the Garden Isle's East shore. Experience the...
OCEAN FRONT UNIT - The Westin Kā‘anapali Ocean Resort Villas
ONE BEDROOM OCEAN FRONT UNIT WITH BALCONYExperience the beauty of Maui with a luxurious stay at the world-renowned Westin Kā‘anapali Ocean Resort Villas. Nestled on 26 acres along the pristine North Kā‘anapali Beach, this resort combines the comforts of home with...
KALANIKAI! 5 MIN WALK FROM POPULAR ALI’I DRIVE
Kalanikai offers a premier location in the heart of Historic Kailua-Kona. Just 2 blocks from the well known Ali'i drive; which offers numerous local shops & restaurants, beach access, and the Kailua Bay pier, where many of the boat tours & excursions depart.The...
Maui Banyan F103 Stunning 1 Bedroom Condo with AC
Maui Banyan F-103 Ground Floor Condo - Complete Remodel. **Please note: This is a ground floor unit, although there are stairs down from the parking lot and another set of stairs down to the ground floor hallway. Everything in the unit has been upgraded! Floors, newly...
1 Bedroom Partial Ocean View at Honua Kai Resort & Spa, Outdoor Pool
Step into your spacious and beautifully designed suite, where modern comfort meets tropical charm. Each unit features a fully equipped gourmet kitchen, furnished lanai, in-room washer and dryer, and luxurious bedrooms and living areas.Why Stay Here?Whether you’re...
Dlx 2-Bedroom Oceanview Kona Condo- Great Views!
Escape to the Big Island at our Deluxe 2-Bedroom Oceeanview Kona Condo rental...Ideally located in Kona featuring a stunning tropical setting. Relax in comfort and style from your own Condo getaway....featuring a relaxed tropical-hawaiian decor. Lounge on your own...
Beach Front Home - Pearl of Oahu's West Side!
Located in Ewa Beach, this awesome house offers 3 bedrooms - one with a queen bed and two with twin beds. With 2 bathrooms equipped with showers, guests can relax and unwind in this soothing space. Whether you're looking to cool off with the AC or iron out any wrinkles,...
NEWLY Updated 4BR OceanView House- Pool, AC & Deck!
Welcome to your slice of paradise! This newly updated 4-bedroom, 2-bath vacation retreat offers the ultimate Hawaiian experience, featuring: -Large open deck with breathtaking sunset and ocean views-A renovated kitchen fully equipped with cookware and essentials-A...
Charming Hawaii Kai home with private pool
***Location and Getting Around***Centrally located in Hawaii Kai! Short walk to Maunalua Bay Beach Park and less than a mile to Safeway, Costco and a handful of restaurants! Less than a ten minute drive in either direction to a number of activities and attractions. Just...
Oceanview Penthouse Maui Retreat – Ideal for a Peaceful, Upscale Escape
Step into comfort, style, and panoramic beauty at this beautifully remodeled 1-bedroom penthouse condo at Island Surf that sleeps 4, perfectly suited for mature travelers seeking both relaxation and convenience. Whether you're enjoying morning coffee on the private...
Large Charming Ocean View studio in terrific Wailea with WiFi, AC
Comfort meets convenience. Our spacious bedroom suite features two queen beds, a covered lanai overlooking gorgeous tropical scenery and stunning ocean sunsets. Nearby tennis/pickleball courts, and golf, active leisure is just steps away. AC wall unit and ceiling fan...
Royal Kahana Maui 803 Ocean View Studio
- Tile & Vinyl plank flooring throughout- Granite counters– fridge, stove/oven, microwave, cookware, tableware- Tiled bathroom with walk-in tiled shower with grab bar- 1 king bed and 1 twin sofa bed- 431 sq ft/40 sqm- 8th floor condo with balcony- Maximum 3 persons...
Palms at Wailea Ocean View Villas 1 Bedroom 2 Bath
Enjoy stunning ocean views from villas featuring a full kitchen, spacious living area, and a private patio; it’s the perfect spot to relax while soaking in Maui’s breathtaking coastal beauty. Ocean View Willa 1 Bedroom 2 Bath• Kitchen includes microwave,...
Suite By the Sea - a bright and sparkling Apartment
Welcome to our new private studio apartment, where comfort and convenience await you. This hidden gem boasts a well-equipped kitchenette, perfect for preparing your favorite meals. Nestled just a short stroll away from the breathtaking Kailua Beach, you'll find yourself...
Luxury 3-Bedroom Oceanfront Villa in Kailua-Kona - Hualālai Resort
Welcome to Hillside Villas, your serene escape nestled in the heart of paradise. Experience the perfect blend of luxury and tranquility in our beautifully appointed villas, where breathtaking views and world-class amenities await. Whether you're here to unwind, explore,...
WAIKIKI SUNSET IN FRONT OF GARDEN OASIS
Discover the beauty of Waikiki from this superb 1-bedroom garden condo. This welcoming space offers guests a large private lanai, fitness center, WiFi, A/C, communal barbeque area and pool on rec deck, two blocks from beach, bus stop @ corner, 24/7 security, on-site...
Chic 2-bedroom furnished resort suite with fitness room and AC in Lahaina, Maui
Welcome to this charming hotel suites in Lahaina. This property features 2 king bedrooms, 2 bathrooms with a bathtub, a cozy living room with a sofa bed, private lanai with outdoor furniture, and amenities like a fitness room, AC, iron, and hair dryer. Guests will feel...
Charming 1BR Premium Villa with Island Views – Westin Ka‘anapali Ocean Resort
Step into island comfort in this 1-Bedroom Premium – Island View villa at The Westin Kāʻanapali Ocean Resort Villas. These villas typically span around 800–900 square feet, offering generous space for couples or small families to unwind in style. Inside, you’ll...
Kiahuna Plantation Resort 66 Partial Ocean 2BD 2BA
Enjoy soft ocean breezes and glimpses of the sea from this partial ocean view one-bedroom condo. Ideally located near the shore, it’s a cozy and convenient Kauai retreat. Unit 66 Partial Ocean View 2 Bedroom 2 Bath• Two-level condo in building 12 with bedrooms &...
Oceanfront Top Floor Molokai Condo! Lush East End Location!
Located on the lush, east end of Molokai. It doesn't get any more oceanfront than this! You won't be able to tear yourself away from the views on the private balcony- just feet from the ocean! Imagine slow mornings sipping coffee and watching whales and turtles. Imagine...
Royal Kahana Maui 707 Ocean View 1 Bedroom
- 7th floor condo with balcony- Vinyl plank flooring throughout- Updated kitchen with– fridge, stove/oven, microwave, cookware, tableware- Updated bathroom with shower tub combo- 1 king bed and 1 queen sofa bed- 777 sqft/72 sqm- Maximum 4 persons including children...
Relax Above the Pacific – 1BR Premium Villa at Westin Princeville
Perched high above the Pacific, this 1-Bedroom Premium Villa at Westin Princeville Ocean Resort Villas offers an ideal blend of comfort, views, and resort amenities. Spanning around 799 square feet, the villa is designed for up to four guests, making it a cozy yet...
Diamond Head Hale | Steps to Sand
Listed as one of Hawaii's historic properties, enjoy some of the best that island living has to offer in this fully furnished 4-bedroom, 3-bathroom Diamond Head Hale. Natural light, refreshing ocean breezes, and hardwood floors flow through this home. 3 bedrooms and 2...
Kaanapali Maui Eldorado G104 Garden View Studio
Relax and recharge in this garden-view studio, set within Kaanapali golf course and minutes from the beach. Whether you're teeing off or lounging on the beach, this peaceful space for two offers comfort and convenience in paradise. Unit G104 Garden View Studio•...
Maui Lahaina Resort 2 Bedroom Sleeps 6
This beach front property is centrally located in the heart of Ka'anapali. Enjoy your morning coffee on the lanai You'll also love cooking in the well-appointed kitchen, so eating out every night isn't a must! Take a dip in either 4 outdoor swimming pools that are on...
Kaanapali Alii 313
Welcome to your dream getaway at Kaanapali Alii 313, a luxury vacation rental nestled in the heart of Lahaina, Maui. This deluxe condominium offers a perfect blend of comfort and elegance, making it an ideal short-term rental for families and couples seeking a serene...
Oceanfront 2 bdm villa on 11th floor Lahaina Towers March 4-11, 2023
Oceanfront 2 bdm villa on 11th floor feels like a penthouse.Available week of Saturday, March 4-11, 2023 only.A tropical paradise awaits you at Marriott's Maui Ocean Club - Lahaina Towers. Boasting an unparalleled location on Lahaina, Maui's world-famous Ka'anapali...
Luxury 2bd/2ba ocean view at Hyatt Resort
****PLEASE READ BEFORE SEND REQUEST TO OWNER***** 2026 available weeks10/31-11/711/7-11/14I offer 10% discount to help cover resort fee and parking fee (total $85/night)The same unit is priced $1500 in Hyatt website for the same weekLuxury fully furnished, 2 bedroom 2...
Regency Waikiki City View 2 Bedroom
Ideally situated in Waikiki, this spacious two-bedroom condo offers all the comforts of home. Perfect for families or couples, it provides plenty of room to relax and unwind. City View 2 Bedroom 1 Bathroom• Kitchen includes ceramic stove top, microwave, dishwasher,...
2 Mi to Hawaii Volcanoes Nat'l Park: House w/ Deck
Work From Home | Modern Kitchen | Near RestaurantsYour month in paradise awaits at this charming 2-bedroom, 2-bath vacation rental in Volcano, Hawaii! Just a few miles away from a spread of scenic hiking trails and the one-of-a-kind Thurston Lava Tube, this property is...
Spacious 2BR Condo On The Beach - Family Friendly - Beach Gear Rentals!
Come explore the Big Island at this premium-level Marriott property on the beach. Surrounded by the clear, blue waters of the Pacific, this dream getaway is the perfect place to enjoy your next tropical destination.This property has everything you need for a tropical...
Charming 2BD + Den Retreat in Princeville – Near Hanalei Beach
Stay near the beaches and beauty of Kaua‘i’s North Shore at Casa La Ola, a modern 2-bedroom + den condo in the heart of Princeville. Enjoy ocean views, walk to Queen’s Bath, and unwind in the pool and spa just steps from your door.Located in one of Princeville’s...
Discover Tropical Bliss: Marriott's Maui Ocean Club - Your Hawaiian Dream- 1 Bd.
Cozy yet spacious. Intimate yet extensive. This one-bedroom features luxurious comfort for memories together and space to escape.If you’re searching for the quintessential Hawaiian getaway, then this resort is quite the catch. If the sunshine, beaches, and glowing...
The Lodge at Kukui‘ula - Bungalow 16
Bungalow 16 at The Lodge at Kukui'ula offers a luxurious retreat on the stunning south shore of Kaua'i. This exquisite three-bedroom, three and a half-bathroom vacation rental is designed to accommodate up to six guests, making it ideal for families or groups seeking an...
Oceanfront Stunning Ocean Views in Paradise at Lahaina Shores Studio
Oceanfront Paradise Studio | Prime Lahaina Location | Stunning Ocean ViewsThe SpaceStep into your own slice of Hawaiian paradise! This thoughtfully designed studio offers everything you need for an unforgettable Maui getaway. Floor-to-ceiling windows frame breathtaking...
Valley Isle Resort #406 - Vacation West Maui
Valley Isle Resort Studio #406 is a beachfront condo located on Kahana Bay in Maui, Hawaii. This studio sleeps up to 4 guests with a queen Murphy bed and queen sofa bed. It features a kitchen, private lanai over the ocean, and amenities such as free WiFi, cable TV, and...
3BR 2.5 BA Panoramic Ocean Views Oasis Na Hale A3
Escape to paradise with this picturesque vacation rental located in the esteemed Na Hale O Keauhou community in Kailua Kona, Hawaii. This tranquil and polished space offers one of the best ocean views in the complex, allowing you to immerse yourself in the beauty of the...
Waikiki Marina Resort Studio
This Waikiki resort offers effortless access to enchanting strolls along the iconic beach. Soak up the sun, try kayaking, or sign up for a surfing lesson. Immerse yourself in a luau and enjoy delicious Hawaiian cuisine while watching traditional dance and music...
Renovated 1BR at Maui Banyan - Pool, Hot Tub, A/C
** 10% of profits go to the Hawaii Community Foundation to support the people affected by the wildfires. Mahalo! **Experience all that Maui has to offer from our newly remodeled condo: ✓ Right across the street from Kamaole Beach II✓ King bed + blackout curtains✓...
Coconut Plantation 1074-4: Upscale 3BR Beach House—Walk to Lagoons & Golf Course
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.As of 07/14/2025Scheduled Maintenance Notice...
Honua Kai Konea 107 Ocean View 2 Bedroom 2 Bath
Konea 107 Ocean View 2 Bedroom 2 Bath- Exclusive on-site provider with the only homes that meet the prestigious AAA 4-Diamond designation- Private spacious lanai opens up to a lush Garden landscaped courtyard with convenient access to the pools- Over 1,300 sq. ft. of...