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.
Royal Kahana Maui 215 Ocean View 1 Bedroom
- 2nd floor condo with balcony- Tile & Vinyl plank flooring throughout- Fully equipped kitchen with– fridge, stove/oven, microwave, cookware, tableware- Tiled bathroom with walk-in pebble shower with grab bar- Queen sofa bed in living area- Central Air Conditioning-...
Makaha Vista Villa - Pool, Amazing Views
Welcome to your private Hawaiian escape on the beautiful west side of Oahu—a stunning 4-bedroom, 3.5-bath estate offering 4,000 square feet of beautifully designed living space. Set in a quiet, upscale neighborhood where homes are generously spaced for maximum...
Kapalua Bay Villa 36B4 Oceanfront 1 Bedroom
- Villa closest to Oneloa Beach- One level condo with no stairs between parking and the front door- Travertine tile floors in living room, dining room, kitchen; porcelain tile in bathroom and carpet in bedroom- Updated white kitchen with granite counters includes...
Sunset/Ocean Views, Two pools, BBQ, Golf, Quiet
Welcome to your relaxing Waikoloa escape - perfect for couples, golfers & beach lovers! Enjoy ocean views, resort-style amenities & a peaceful setting just minutes from top Big Island beaches:- Sleeps 2 | 1 bedroom | 1 bed | 1 bath- Pools & hot tub- Private lanai w/...
Aloha Moana: Luxe 180° Oceanfront Escape
★Legal Vacation Condo Rental ★Hale Pono Kai: A new & elegant modern condo awaits to become a cherished part of your paradise retreat! Your newly appointed haven was attentively remodeled in November 2022 using modern yet soothing decorative elements seamlessly...
Marriott Maui Ocean Club - 2 Bedroom/2Bath Ocean Front in Lahaina Tower
Welcome to this charming condo in Lahaina with private lanai's at the luxurious, five star Marriott's Maui Ocean Club Resort. This amazing property features 2 bedrooms with a king bed and a full bed, along with 2 bathrooms equipped with a jetted bathtub in the master...
Kihei Maui, 2 Br, Unit#2n
Your family will be close to everything when you stay at this centrally-located place....................................................................................................................
Stunning Lanikai studio - 5 min walk to Kailua and Lanikai Beach!
Beautiful hillside studio with breathtaking ocean views. Wake up to spectacular sunrises, watch the whales play, and enjoy the ocean breeze as you live the Lanikai lifestyle. Complies with Hawaii law.
NEW LISTING! Offering limited time introductory rates! Luxury Remodeled Townhouse with Breathtaking Golf, Mountain & Partial Ocean Views
NEW LISTING! Offering limited time introductory rates! Enjoy the 5th Night Free for stays between now and December 15, 2025. Reservations must be made by August 31, 2025. *Applies to new reservations only. Property Highlights • Luxury remodeled townhouse offering...
Royal Kahana Maui 912 Oceanfront 1 Bedroom
- 11th floor condo with balcony- Vinyl plank flooring throughout- Fully equipped kitchen with– fridge, stove/oven, microwave, dishwasher, cookware, tableware- Tiled bathroom with walk-in tiled shower- 1 king bed and twin sofabed- Washer/dryer in unit- Central air...
'Olina NEW (PKC 106) ~ 3 BR ~ Ground Floor ~ Pool
Summary:'OLINA, Puako Condo 106 is a ground floor unit that was designed with great attention to detail for a clean modern style and high quality feel throughout. The unit stays cool with two A/C units (one in the main bedroom and one for the living room kitchen) and...
Royal Kahana Maui 606 Ocean View 1 Bedroom
- 6th floor condo with balcony on the north side of the building- Updated open kitchen with granite counters includes stove, oven, refrigerator, microwave, coffeemaker, toaster, coffee starter kit, blender, tea kettle and complimentary tea- Tile flooring throughout-...
Royal Kuhio 1707 - Spacious Studio w/ Diamond Head and City Views in Waikiki
Heart of Waikiki - Royal Kuhio (17th Floor)Address: 2240 Kuhio Ave., #1707, Honolulu, HI 968151 Bed | 1 Bath | Sleeps 4Beds: 2 Full-size beds + 1 Queen sofa bedSize: 436 sq ft + 80 sq ft lanaiKitchen: Fully equipped with oven, microwave, modern appliances, cookware, and...
Sugar Beach Resort - #131 - Sanitized - Oceanfront - Ground Floor - Walk Out
Sanitized with Quaternary Ammonium for COVID-19Hawaii Tax # TA/GE: 096 120 6272-01Lawn, sand, and ocean only 15 yards away at your fingertips at Sugar Beach Resort. Ground floor, oceanfront walk-out, unit #131, newly renovated. Convenient covered parking in the MILL...
Kaanapali Alii | 333
Located on the third floor and in the building on property closest to the ocean, you will be able to hear the sounds of the waves crashing on Kaanapali Beach just outside your vacation rental. Engage more of your senses and head out to your private lanai where you can...
Wailea Ekahi Village | 52D
Wailea Ekahi 52 is a luxurious vacation rental property located in the heart of the idyllic Wailea resort community on the southern shores of Maui. This spacious, one-bedroom, one-bathroom condominium offers guests a serene and indulgent island getaway, with all the...
Waterfront studio with mountain view, rooftop pool, hot tub, sauna & central AC
Honolulu Horizon Haven-30 night minimumOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Perched high above the bustling city of Honolulu in Waikiki, this stunning condo offers a...
Sunset Shores - UNIT B Kauipoho
Summary:Relax with the Escape to serenity in this shared Kailua Kona space. Embrace the tranquil island ambiance and inviting interiors.With convenient beach access, this is an ideal location for a peaceful coastal getaway. Immerse yourself in the beauty of Hawaii and...
Just Listed! Top Notch Rental Experience Awaits!
Experience breathtaking sunsets every evening from your private lanai and immerse yourself in the fresh ocean air at Kaleialoha 213. This West Maui vacation condo is perched right on the water's edge, offering unparalleled proximity to the ocean. The property boasts a...
Views on the Kaanapali Coast!
Prepare to be completely swept away by the breathtaking beauty and boundless excitement that awaits you on the island of Maui, your best vacation yet! At the beachfront retreat of Paki Maui, the azure waters of the Pacific Ocean gently caress the golden sands just steps...
Hale O Ka La – Luxury Villa at Mauna Kea Resort
MEET THE VILLAHale 'O Ka La on the Big Island defines Hawaiian luxury. Developed by Laurance S. Rockefeller in the 1960s, Mauna Kea Resort was the Kohala Coast's first luxury destination and remains an icon of island elegance.This stunning 5,358 sq. ft. estate features...
Kapalua Ridge Villa 124 Gold Ocean View 1 Bedroom
- Villa is closest to Oneloa Beach- Second floor unit with 15 stairs from parking to the villa- Tile flooring in kitchen, bathroom and carpeted in living room and bedroom- Fully equipped kitchen with stainless steel appliances includes stovetop/oven, microwave, and...
Quiet Condo, Gorgeous Views, Golf Course, 2 Pools
Welcome to your Hawaiian escape - a peaceful condo w/ stunning golf course & ocean views, perfect for relaxing after Big Island adventures:• Sleeps 4 | 2 bedrooms | 2 beds | 2 baths• 2 pools, hot tubs, tennis courts• Private lanai for sunsets & morning coffee•...
Gorgeous 5 br for 12 in Kapaa - Beachfront!
Listing provided by "The Vacation Rental Experts". Contact directly for more options!The fabulous 5 bedroom, 4 bath oceanfront for 13, is made up of a 3 bedroom and 2 bedroom oceanfront townhome, just steps apart! Fabulous beachfront pool and sundeck onsite! Beautiful...
Luxurious 2-bedroom/2-bathroom oceanfront condo with pool, jacuzzi and parking
Escape to this oceanfront condo on Oahu’s North Shore. This spacious end-unit features 2 bedrooms, 2 bathrooms, and comfortably sleeps 4+ with 3 beds. Enjoy breathtaking ocean views from large bay windows or relax with the soothing sound of waves. The condo includes...
Maui Resort Rentals: Honua Kai – Incredible 5 Bedroom Oceanfront Gem, Over 3400 combined Sq. Ft. w/ Built-in Viking B.B.Q.
This 5-bedroom gem combines one of our very finest 3BR oceanfront "Ali'i" residences with a spacious partial ocean view 2BR suite located directly next door and is perfectly suited to larger groups or families.The generous 3400+ sq ft of the combined interior living...
Spacious & Breezy 3 Bedroom Home with Ko'Olau Views and a Pool
Nestled in a quiet neighborhood, this charming home is located just one mile from the heart of Kailua town's shopping and resturants. It is also just a bike ride away from the world famous Kailua and Lanikai Beaches. With stunning views of the Ko'olau Mountains and the...
Kapalua Golf Villas Gold Fairway View 2 Bedroom
Golf Villas Gold Fairway View 2 Bedroom 2 Bath- Situated along Kapalua’s Bay Course fairway- Fully equipped kitchen includes stovetop/oven, microwave, refrigerator, coffeemaker, cookware, tableware- Master bedroom with 1 king bed and bathroom- Guest bedroom with 2...
Kaanapali Alii | 124
Kaanapali Alii 124 is an exquisite two-bedroom ocean-view rental that is perfect for families or groups seeking a luxurious getaway in Maui. This spacious residence features an open floor plan that seamlessly connects the living, dining, and kitchen areas, creating a...
New Listing! Save up to 25% Instantly on stays thru 5/31/25! 2B/2B, AC, Pool
Experience tranquil island living at Kaanapali Plantation 12, nestled on 10 acres of lush tropical gardens. This serene and spacious retreat is just minutes from the renowned Kaanapali Beach. This charming 2-bedroom, 2-bath condo is a haven for golf enthusiasts,...
2 One-Bedroom Suites w/ Lanai – Close to Dining, Shops & Cultural Sites
Make this comfortable and convenient property your next Waikiki adventure! Relax by the pool, enjoy dinner with family at one of three on-site restaurants, or grab a pastry and morning coffee at the coffeehouse. And best yet, the sun, sand, and surf of Waikiki Beach are...
Ko Olina Kai 1083C: Contemporary 3BR, Private Lanai, Walk to Beach & Dining
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.Welcome to Ko Olina Kai 1083C by Gather, a...
Charming 4-bedroom cottage with WiFi and AC in serene Laie
Consider this cottage your home away from home while you visit Laie. This delightful property boasts 4 bedrooms including a king bed, 2 bunk beds, a queen bed, and a futon. With 4 bathrooms equipped with showers, your group will have plenty of space to freshen up. The...
Corner Unit 1 Block to Beach in Heart of Waikiki!
Ni'ihau Apartments #605 – 247 Beach WalkLocation, location, location! Ni'ihau is a hidden gem found within the hustle and bustle of Waikiki just a block away from world-famous Waikiki Beach where surfers and paddlers spend their days! Beautiful corner unit (673 sqft)...
Maui Resort Rentals: Honua Kai - 5 Total Bedrooms, 8th Floor "Penthouse" Ocean AND West Maui Mountain Views, Deluxe Corner Floor Plan!
This premier eighth-floor offering pairs one of our most sought after two-bedroom "penthouse" suites with three neighboring one-bedroom suites to create the perfect place for your group to gather, reconnect, and celebrate. Enjoy unparalleled views of the blue Pacific...
Oceanfront Kona By the Sea 2-Bedroom Retreat with Central A/C
45-Night Minimum • Central A/C • Heated Salt-Water Pool & SpaSavor jaw-dropping, third-floor ocean vistas and nightly Kona sunsets from the private lanai, living room, and even the kitchen of this spacious 2-bedroom, 2-bath suite at coveted Kona By the Sea.Inside...
New Listing Specials! Walk to Beach. Sleeps 6. Fantastic Resort Amenities.
Centrally located in Kihei and a three minute walk to Kamaole Beach, where you'll have access to some of the area's best snorkeling, whale watching, and sunsets. Short drive to coveted Wailea beach!★ Ocean View★ Private bedroom and bathroom★ Two full bathrooms★...
Relaxing Kalakauan 1-Bedroom | Private Lanai
This family-friendly vacation home is tucked away at the beginning of the Waikiki strip and features secured entry. This 1-bedroom, 1-bathroom offers easy access to the Waikiki Strip, Hilton Hawaiian Village, Fort DeRussy Beach Park, world-famous Waikiki Beach, Hawaii...
4 Units Perfect for Groups! Outdoor Pool, Close to the Beach!
Our spacious suites with private lanais offer breathtaking views of the pristine shoreline, courtyard, or garden, providing the perfect backdrop for relaxation and adventure. Stay connected with high-speed internet, unwind in our unique whale-shaped outdoor swimming...
Wailea Point Contemporary 2 Bedroom+Loft/3 Bath Oceanview Condominium
Yes, you can treat yourself and stay in a vacation home at Wailea Point! A premier hospitality destination nestled between the Four Seasons Wailea Resort and the Fairmont Kealani Wailea, featuring an optimal location near beaches, golf, restaurants and entertainment....
Hale Lu'u Kini Ea B-310 Stunning Ocean Front Villa
Hale Lu'u Kini Ea - Your Perfect Hawaiian RetreatWelcome to Hale Lu'u Kini Ea, a spacious 2-bedroom, 2-bathroom villa located in the tranquil Beach Villas at Ko Olina. This villa offers breathtaking ocean views from every bedroom, allowing you to wake up to the serene...
Charming Kihei Getaway | D410 at Kihei Akahi | Steps to Beach
Charming Kihei Getaway | D410 at Kihei Akahi | Steps to BeachWelcome to your perfect Maui retreat! This beautifully appointed one-bedroom condo offers the ideal blend of comfort, convenience, and tropical charm, all within walking distance to South Kihei's most beloved...
Maui Resort Rentals: Honua Kai Hokulani 1029 - 2BR Deluxe Oceanview Grand Penthouse, BBQ on Balcony + Jaw-Dropping Ocean Views!
We are proud to present this jaw-dropping 10th-floor deluxe oceanview grand penthouse at the Honua Kai Resort—newly launched on 3/4/25 to start taking bookings beginning May 7, 2025!Unquestionably one of the finest residences on offer at Honua Kai, this stunning...
Ko Olina Kai 1081C: 3BR Tropical Retreat, Steps from Golf and Dining
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.Discover the epitome of island elegance at Ko...
1 BR Suite City View, w/ AC, WiFi and Kitchen - Bamboo Waikīkī Hotel #504
Castle Bamboo Waikīkī Hotel #504 - The living area is furnished with a and a desk/workspace for all those business travelers. Enjoy watching the Flat screen TV while sitting on the new couch, which doubles as a fold-out sofa bed to accommodate additional travelers....
Maui Resort Rentals: Honua Kai Hokulani 814 - Top Floor 1BR w/ Partial Ocean & Mountain Views!
This beautifully appointed top floor "penthouse" suite boasts one of the best one-bedroom locations available at Honua Kai. Enjoy generous partial ocean views from the balcony and primary bedroom in addition to great views of the verdant West Maui Mountains. This suite...
Modern Island Comfort in the Heart of Waikiki - Aloha Surf Hotel Studio
Aloha and welcome to your dream getaway in Waikiki! Nestled in one of Honolulu’s most iconic boutique hotels, this charming studio at the Aloha Surf Hotel offers the perfect blend of island style, modern comfort, and unbeatable location. Whether you’re looking for a...
"BEAUTIFUL LUXURY CONDO WITH GORGEOUS VIEWS 1BR/1BA/1PKG AT SKY ALA MOANA"
"MODERN LUXURY CONDO WITH BEAUTIFUL VIEWS 1BR/1BA/1PKG AT SKY ALA MOANA""WELCOME TO SKY ALA MOANA" Luxury condominium built in 2023 conveniently located in Ala Moana. Enjoy beautiful views of city, mountain and sparking ocean. 1br/1ba /1assigned parking with Full...
Marriott Maui Ocean Club | Three 3BR/3BA Villas
Summary:Located on the shores of Ka'anapali Beach, Marriott Ocean Club is surrounded by Hawaii's beautiful scenery! The resort is the perfect family getaway with something for everyone to enjoy - beautiful pools, golf, on-site dining, spa services, and sports courts....
Ocean-MT Views From the Luxury Sky Ala Moana Condo with Amazing Amenities
This property requires a minimum 30-day rental. Book with confidence—professionally managed by Ali'i Beach Rentals, an award-winning property management company.The Sky Ala Moana is the newest addition to the luxurious building scene in Honolulu. Consisting of two...