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.
Private Luxury Estate w/Pool, Jacuzzi, AC & Ocean Views: Ohana Le'ale'a
Step into the beauty of island life at Ohana le'ale'a, a newly built 3-bedroom, 3.5-bath luxury estate in Kona that blends expansive indoor-outdoor living with sweeping Pacific views. With 3,180 square feet of refined design, a private pool and spa, and a game room...
KV E609 Remodeled 2Bedroom Condo w Pool AC Near Beach
Kahana Villa E609 Bright Blue Ocean Views from Remodeled Island Style 2Bedroom Condo in Kahana Across Street From Beach! Island Living with Conveniences of Home FREE daily activities included with your stay value up to $570! Complimentary admission, every day of your...
- Luxury Vacationing Modern Condo - Spring Specials -299 USD-
***The pool has just been renovated and is gorgeous*** DESIGNED BY A NYC ARTIST. THIS BEAUTIFUL CONDOMINIUM IS BORDERING KIHEI AND WAILEA IN SOUTH MAUI, HAWAII. IT IS LOCATED AT THE GORGEOUS MAUI HILL RESORT BY ASTON. THE PROPERTY HAS BEAUTIFUL GARDENS, SWEEPING VIEWS...
Oceanfront HK-B7 - Maui Condo on the Beautiful Serene Beach of Ma’alaea Bay
Experience the ideal beachfront getaway at Hono Kai B-7, a charming condo nestled in the serene beauty of Maui. This idyllic retreat offers stunning ocean views from the living room, bedroom, and lanai, providing a picturesque backdrop for your vacation. The...
Panoramic Ocean & Mountain Views --we have FULL AVAILABILITY please message us.n
Let the Aloha spirit be with you during your Hawaii visit by staying along the famous Koolau Mountain range on the lush Windward Side of Oahu. With 3900 sq. ft. of space to relax and enjoy a panoramic view of the grand mountains and the peaceful ocean as a backdrop,...
Ho'olei Ocean View 21-6 Newly Listed, Renovation May 2025
Remodel completed June 2025! See the new photos just posted!The entire home has been repainted, almost all the furniture was replaced, a lot of new beautiful art was added, and all new hardwood French oak floors were installed in the bedrooms.. We also remodeled the...
Luxury Oasis Palm Villas at Mauna Lani
Luxury Oasis at Palm Villas in Mauna Lani Resort on the Big Island of HawaiiWelcome to your dream Hawaiian getaway at the Palm Villas located in the Mauna Lani Resort, where paradise meets perfection! Nestled within the prestigious Palm Villas community, our luxurious...
Breezy Pool Oasis 5BR AC Ocean Views 5min to Beach
Welcome to your tropical paradise getaway! This resort-like 5 bedroom home with swimming pool, hot tub, waterfalls, and stream is ideally located in a quiet cul-de-sac and offers the perfect blend of relaxation, comfort, and breathtaking ocean views. With Magic Sands...
Tropical-inspired decor with partial ocean view
Kuleana Resort 313 is a charming 1-bedroom, 1-bathroom condo that comfortably accommodates up to 4 guests. The spacious bedroom features a luxurious California King bed, complemented by 1 window A/C unit for added comfort. Additional sleeping arrangements include a...
3 BR Oceanfront Villa: Marriott's Lahaina Tower; Jan 9 - Mar 6th, 2027
Spend up to 8 consecutive weeks in the same 6th floor oceanfront villa within Marriott Ocean Club Lahaina Tower! Availability 1/9/27 through 3/6/27Can also be rented weekly. All weekly rental reservations must begin on a Saturday and depart on a Saturday.This 1700...
Hale Hahalua - Serenity and Ocean Views in Kona now with upgraded A/C in bedr.
Aloha! Welcome to Hale Hāhālua – the gateway for your dream vacation on the Big Island of Hawai’i. Located in the picturesque community of Keauhou (Kailua-Kona), right above Keauhou Bay, our condo offers you the perfect starting point for your adventures. In...
Kona Coast, BEST Oceanview&Pool, Yoga/Meditation Space, Pickle Ball&Basket Ball
Welcome to Halani — Your Serene Sanctuary on the Big IslandEscape the busyness and crowds of the resort scene and discover Halani, meaning “heavenly breath”—a peaceful retreat perched above the South Kona coast, offering one of the most unparalleled ocean views...
New Listing! Tropical-themed 7th floor studio
Kaanapali Shores 721 is a Studio condo with central air conditioning that can accommodate up to 3 guests. Located on the seventh floor, you will find an open-concept layout and tropical-inspired decor with a sense of island serenity. When it's time to rest, unwind on...
Mau Loa Hale: Perfect Location 5 Acres Walk to Bch! Open concept! Breeze & Views
Welcome to Mau Loa Hale, a private island-style retreat on five acres between the Koʻolau Mountains and the Pacific. Here, dramatic ridgelines meet ocean breezes, creating a peaceful escape where you can spread out, recharge, and experience Oʻahu at a slower rhythm....
TRUE OCEANFRONT PARADISE! Royal Mauian #311
ALOHA!Welcome to Kihei, Maui and your oceanfront paradise! Our incredibly beautiful condo is near the center of the building and only steps away from the water. Watch whales, savor the sunset and enjoy the sound of the waves from the large lanai, the living room or even...
Spectacular Panoramic Ocean Views - Private Ohana
Live like a local at the Ocean Blue Ohana. You'll have the entire private first floor of this amazing Hawaiian pole home on a half acre property in South Maui. As you enter the space, you will be drawn to the sweeping panoramic ocean views. You are sky-high, perched 500...
Aloha Condos, Kanaloa at Kona, Condo 3703, Oceanfront, AC
1700 Square feet of breezy vaulted-ceiling living space, with new tile floor and paint throughout. Refinished koa wood cabinetry in all new kitchen. Ceiling fans in all major rooms and lanai (5). Powerful whole house ventilating system reduces demand for AC. High...
Waikiki Shore Beach Front Studio
Large beach front studio (460 sq, ft,) located at the Waikiki Shore, the only condo building in Waikiki that is directly on Waikiki Beach. This unit is located in a building that is within the designated Resort Zone, and therefore eligible for short term vacation...
Waikoloa Village Golf Course Fairway 2-bedroom condo with Central AC-WiFi, Views
Waikoloa Fairways -From the Summit of Mauna Kea to the Kohala Coast Line, Welcome to Paradise! Central Air Conditioning! Aloha! E Komo Mai! This gorgeous condominium offers everything you need for your Big Island getaway. Located in the highly sought after community of...
Renovated 03/23! Direct Oceanfront Condo with 2 Master Suites!
*Available for booking! Thankfully, our condo is not located in the wildfire affected area*Enjoy stunning views in this newly renovated oceanfront condo located on Kahana Beach! This spacious 1,040 sqft condo located at Valley Isle Resort has been completely renovated...
Kolohala in Haena is a tranquil place to enjoy your tropical vacation!
Kolohala in Haena is a peaceful place to enjoy your tropical vacation. Great for honeymooners! It faces a beautiful meadow with horses and cows. You can walk to a string of white sand beaches in 5 mins. Close to Ke'e beach, Tunnels beach, Kalalau hiking trails, Napali...
Westin-Top island and beach in the world, oceanfront, pools, kitchen, family
The Westin Nanea Ocean Villas, Ka'anapali, is built on 16 acres on Maui's legendary North Kā’anapali Beach. Enjoy Maui's newest oceanfront resort, where you can relax in paradise. Walk out onto the spectacular beach, lounge at the beautiful pools (heated pool,...
Oceanfront Boutique Condo. 5% Discount for Most Stays of 7 or More Nights
Enjoy stunning ocean views from all the bedrooms and living area of the condo. Greet every morning on your bed enjoying the views and sounds from the ocean!*** OCEANFRONT overlooking greenbelt, quiet and private, no noise from pool or parking lot ***Uncork a bottle of...
Two Bedroom Upgraded Waikoloa Fairway Villa
Perfect for a postcard worthy family vacation, girls’ getaway, solo trip, or whatever your heart desires, Fairway Villa C21 is located in the Fairway Villas gated community of Waikoloa Beach Resort and is the perfect destination for rest, relaxation, reconnection, fun...
Luxurious 2-Bdrm, 2.5-Bath Condo with Parking & Fitness Center in Prime Waikiki!
Experience luxury living in this 2 bdrm/2.5 baths/1 parking, corner-end unit at Waikiki Landmark! Located in the Makai Tower, this unit offers breathtaking city and partial ocean views. No detail was overlooked in the thoughtfully designed kitchen renovation, featuring...
Hale o ka Nene: Luxury 6BR Estate with Pool, Spa & Golf Views
Welcome to Hale O Ka Nene, a striking six bedroom, six and a half bathroom estate set within the exclusive enclave of Kukui‘ula on Kaua‘i’s sun drenched South Shore. Designed for refined island living, this 4,200 square foot holiday home accommodates up to fifteen...
Hawaiian Bungalow ~ A/C~ Near Beaches & Shops
Experience the aloha spirit in this bright, airy Hawaiian-style home, where vaulted ceilings and tropical garden views create the perfect island retreat. Designed with family fun in mind, the game room offers ping pong and foosball, and the garage is stocked with...
Lei Hali'a - Steps Away from Poipu Beach with A/C!
Located just steps away from the world famous Poipu Beach and Brennecke’s Beach on Kauai’s sunny South Shore, Lei Hali’a is ready to help you create lasting vacation memories from this island paradise. From the spacious and comfortable outdoor living space...
Pu'uwai Place in the heart of Volcano Village
Pu'uwai Place is centrally located in the heart of Volcano Village, just outside Hawaii Volcanoes National Park. Cooper Center, convenience stores, and restaurants are all within walking distance. You'll feel right at home in this newly updated home with full private...
Oceanfront Paradise! Sea Turtle Cove Napili Point
WOW! Spectacular Ocean and outer island views. Your oceanfront patio is just steps away from the beautiful Honokeana Cove (commonly called turtle cove), which lends to excellent and safe snorkeling on most days. Sip on your Mai Tai, take a deep breath, and enjoy the...
STEPS FROM STUNNING MOLOAA BAY
Formerly "Hale Houston" Moloaa Beach Hideaway is a 2 bedroom, 2 bath home situated just steps away from beautiful Moloaa Bay on the northeast shore of Kauai. Walk up a flight of stairs to enter this 1200 sq.ft. spacious, air conditioned well appointed home with an open...
Ocean View Paradise: Spacious 2-Bedroom Condo at Kaanapali Shores
Experience the ultimate Maui getaway at Kaanapali Shores 416, a beautifully maintained 2-bedroom, 2-bathroom condo that promises breathtaking ocean views. The open-concept living space seamlessly blends indoor and outdoor dining, making it easy to savor meals while...
Gratitude Bed and Breakfast BBWK2022/0001
This is a Bed and BREAKFAST, I provide you with Local food for breakfast!We are within walking distance to Wailuku town which has coffee shops, restaurants, boutiques, antique shops and Local Acting Theater. You’ll love my place because of the coziness, the vaulted...
Wailea Ekolu #405 SUPREME OCEAN VIEW on Wailea Golf Course w/ FULL A/C
Introducing the newest unit in our portfolio! Please visit and be our first review with an introductory Special Rate till August 31th! Wailea Ekolu #405 is an ocean view 2 bedroom, 2 bath ground floor unit with air conditioning throughout, a fully equipped kitchen,...
Mauna Kea Luxury - 180º Ocean, Maui & Sunset Views, Heated Private Pool & Spa
This stunning home offers the best of both worlds: the comfort of a spacious, private home and access to all of the facilities of the Mauna Kea and Hapuna resorts. All four bedrooms have en-suite bathrooms. We have not furnished and equipped this as a "rental property",...
Hale Pohaku Kai: Poipu Seaside Stunner
Hale Pohaku Kai is a paradise of paradoxes: elegantly furnished, yet casually comfortable; spacious & airy yet cozy, too; wonderfully private, but with Poipu’s world-class sandy beaches, parks, restaurants, shopping & lively local events only a few minutes away. The...
Actual Owner! - Marriott Beautiful Ocean Front Villas- 2bdr/2bath sleeps 8+1
Special cancellation policy for Pandemic quarantine restrictions; please inquire for details.Marriott continues to closely monitor and comply (exceed) the Centers for Disease Control and Prevention (CDC), World Health Organization (WHO) guidance.We will be happy to...
BIG ISLAND HALE MELE MELE, Lovely Cottage in Magical Puako!
NEWLY AVAILABLE DATES JANUARY 4 - 13, 2026COME SEE THE HUMPBACK WHALES AND ENJOY THE GREAT WEATHERHale Mele Mele is one of Puako’s original beach cottages lovingly restored, refreshed and redecorated to feel like home-away-from-home. The fully-equipped kitchen, while...
Amazing House with Pool, Spa, Cabana & More Kihei Wailea Area
The Maui Meadows Guesthouse Property is 3/4 mile from (8) premier beaches and features: (4) Bedroom, (5) Bath one story 2700 sq ft house, Proximity to beaches, activities, golf, shopping, restaurants and bars, Air conditioning, 65" TV screen with Streaming TV with NFL...
Kuilima Condo with Split Air
Welcome to our little piece of paradise. A perfect place to stay during your visit to Oahu. Our CLEAN and beautifully UPDATED condo can sleep 6 comfortably. With TWO king beds and a one queen sofa bed. It also includes a brand new full-size kitchen with a dishwasher,...
Private pool and jacuzzi oasis; walk to the beach, golf, restaurants, shopping
Your own private tropical pool and jacuzzi! Hale Ohana is open concept home with an expansive living room, dining room, and kitchen with breakfast bar that are to be enjoyed. Ceiling fans and Hawaiian louvered windows in every room allow you to enjoy the cool trade...
Top Floor Ocean Front Molokai 1 Bedroom Condo
Our condo is located in east end of island of Molokai. It is “NOT” on Maui. Recently totally renovated.Has spectacular views of the ocean and of west Maui coast. Watch whales from lanai during mid Dec-early April Book now don’t miss out everything is filling fast....
New Listing! A/C ~ Ocean & Golf Course Views ~BBQ
Relax & recharge in this calm, stylish space. The A/C or tropical breezes await you after a day of island adventure. Nestled near the ocean bluff along the Makai Golf Course. The kitchen is fully equipped. New furniture throughout. Private gas BBQ. Private washer/dryer....
New! Maui Banyan G105 – Heart of Kihei
Maui Banyan G105 – Ground-Level Comfort Near the Pool in South Kihei!Welcome to your perfect Maui retreat! Located in the desirable Maui Banyan Resort, this ground-floor 1-bedroom, 2-bath condo offers comfort, convenience, and a fantastic South Kihei location—just...
Maui North Shore Villa: Private Pool, Courtyard & Steps to Baby Beach
Your North Shore Beach Retreat in Maui’s Premier Neighborhood:Nestled in the heart of Spreckelsville, this is more than a beach house—it’s a place to slow down and savor what makes Maui special. Just a 3-minute walk from Baby Beach, with its calm lagoon waters...
Ocean-Waikiki Skyline Panoramic PH in Luxury Condo w/Parking & Near the Beach
This property requires a minimum 30-day rental. Book with confidence—professionally managed by Ali'i Beach Rentals, an award-winning property management company.*This penthouse is new to our inventory. Reviews are coming soon. Please rest assured this house is...
Stunning Ko Olina 2BR Beach Villa O414 w/ Golf Course, Mountain & Ocean Views
Welcome to Ko Olina Beach Villa O414 by Gather, an exquisite 2-bedroom, 2-bathroom haven in Kapolei, HI, perfect for up to six guests seeking a blend of luxury and comfort. Located on a serene corner of the 4th floor, this villa presents stunning views of the golf...
NEW LISTING SPECTACULAR OCEAN FRONT VIEW FROM EVERY ROOM - PRINCEVILLE/HANALEI
A beautiful, unobstructed view of the deep blue Pacific Ocean and coral reef from every room! Our condo is located on an ocean bluff having the luxury of a 180 degree view of blue water from every room. Along with magical waves, you will see outrigger paddlers and sea...
Pool & Beachside—NEW Kailua Luxury Beach House - Direct beach access!
Indulge in an Unforgettable Stay at Our BRAND-NEW Luxury Beach House at Kailua BeachEscape to our newly built, luxurious rental home, perfectly nestled in the heart of the most sought-after location by the world-renowned Kailua Beach. This contemporary haven is designed...
Charming Ocean View Home with Central A/C - walk to Downtown Paia and Beaches
Experience the beauty of Maui’s North Shore from this private, ocean-view home just minutes from downtown Paia and some of Maui’s best beaches. This spacious 3-bedroom, 2-bath vacation rental offers the perfect balance of tranquility and convenience, featuring...