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.
Ocean Sanctuary Beachfront 1-bedroom Kihei, Maui
This charming condo offers breathtaking views of Maalaea Bay, West Maui Mountains, Kealia wetlands and bird sanctuary and out the front door, Haleakala, Makena and Molokini crater. Offering a 360 degree view from this 6th floor perch! Situated directly on Sugar beach...
Kukuiula Makai Cottage #12: Plantation-Style 2BR Retreat in Poipu
Kukuiula Makai Cottage #12 is a charming cottage nestled in the heart of Poipu’s highly sought-after Kukuiula neighborhood. This single-story plantation-style retreat blends vintage Hawaiian charm with upscale modern comforts. Featuring two bedroom suites, this...
Waikoloa Colony Villas Unit 2001 Garden 2BD 2BA
Waikoloa Colony Villas is located at 69-555 Waikoloa Beach Drive, Waikoloa, HI 96738 - Guests check in at Hawaii Vacation Condos by Outrigger’s office located at the Kings’ Shops, 69-250 Waikoloa Beach Drive, Suite B-13. Open daily from 9am-5pm. - Townhome with...
Kaanapali Alii | 125
Kaanapali Alii 125 is an oceanfront second-floor condo that offers breathtaking ocean views from your private lanai, living room, and master bedroom. This beautifully designed two-bedroom, two-bath vacation rental combines island-inspired aesthetics with modern...
Serenity in the Sky!
Gorgeous brand new home with 3 bedrooms and 3 full bathrooms with beautiful views, privacy and absolute serenity. All new stainless appliances & new furniture, beautiful kitchen with granite and spectacular view and WIFI.!Wake up and enjoy the best sunrise on the island...
Luxurious & Spacious Ocean Vistas
Summary:Beautifully remodeled in early 2023. This elegant 2-bedroom, 2-bath condo features upscale touches with magnificent ocean views. Located steps from Wailea, all of Maui is within reach. We offer a fully stocked kitchen for those who want to cook. Enjoy the...
Beachfront in Haleiwa, Sea Turtles and Sunsets!
Welcome to one of the most unique beachfront homes on Oahu’s north shore. Located directly on the breathtaking Laniakea beach, this location is well-known for spotting Hawaii’s endangered green sea turtles along the shore! Laniakea is also a lovely beach for...
Fairways North 32
Nestled in the sought-after North Fairways of the prestigious Mauna Kea Beach Resort, this charming 4-bedroom residence offers the perfect Hawaii vacation experience. Enjoy breathtaking panoramic ocean views complemented by glimpses of Maui and the Kohala mountains....
Spacious 8BR w/Ocean Views, Sleeps 16 with AC in fabulous Kailua-Kona
This luxurious modern Hawaiian compound features two newly renovated, pristine homes — an ideal retreat for large families, extended group vacations, or friends traveling together. Nestled within the prestigious guard‑gated community of Kona Bay Estates, the...
NP B18 Remodeled Oceanfront 1BD Steps to Pool
Napili Point B18 NEW LISTING Wake up to Amazing Ocean Views in this Beautifully Appointed Ground Floor Condo at Napili Point! FREE daily activities included with your stay value up to $570! Complimentary admission, every day of your stay*: Whale Watch (seasonal), Dinner...
Golf Course View Waikoloa Colony Villas Townhouse with Pools, Gym & Beach Gear.
Enjoy a spacious and inviting two-bedroom townhouse located within the desired Waikoloa Beach Resort community. This meticulously cared for condo features magnificent mountain and wide-open golf course views. The garage is stocked with everything essential for a fun day...
Oceanfront Suite w/ Floor to Ceiling Windows, Lanai, Free WiFi & Free Parking
It’s all about ocean views and relaxation. Only at Mahana at Kaanapali will you find perfect panoramic views in every suite. Relax by the pool, soak in a hot tub, then take a leisurely stroll down a mile-long stretch of golden beach. You’ll be impressed by the...
Westin Kaanapali Ocean North Resort Studio Villa
Located in Lahaina, this delightful hotel offers a peaceful retreat for guests. With a cozy living room featuring two futon beds and two king beds, this welcoming property provides ample space for relaxation. A fitness room, WiFi, and AC ensure guests have everything...
KHV 3 Remodeled 2BD West Maui Condo Breathtaking Sunsets from Oceanfront Lanai
Kahana Village 3 NEW LISTING Fabulous Direct Oceanfront Views and Sunsets from this 2Bedroom, 2Bathroom, West Maui Condo on the Beach in Kahana! FREE daily activities included with your stay value up to $570! Complimentary admission, every day of your stay*: Whale Watch...
Top Floor, Centrally Located Condo, AC, Private Lanai, Steps to Beach
A L O H A ! ! !Top Floor, Centrally located, Condo with AC. Sleeps 4+ Parking included for one vehicle Imagine stepping out onto your lanai with a cup of coffee, and feeling the Hawaiian breeze carry your worries away. Whether you're planning a weekend escape or an...
Escape to Wyndham Kona Hawaiian: Island Vibes, Spacious Villas & Beach Bliss
Get ready for the ultimate family escape to paradise at Wyndham Kona Hawaiian Resort on the breathtaking Big Island of Hawaii! Nestled along the stunning Kona coastline, this family-friendly resort offers the perfect combination of relaxation, adventure, and Hawaiian...
Island Serenity Awaits: Studio Premium Villa at Westin Ka’anapali North
Escape to the tropical paradise of Maui with a stay in the Studio Premium Island View Villa at Westin Ka’anapali Ocean Resort Villas North—a perfect blend of luxury, relaxation, and family-friendly fun. Surrounded by lush island landscapes, this retreat is ideal for...
🏝️Summer Deals-New Luxury, Family 2/2, Walk to Beach, Ocean View🏝️
Beautiful Maui Condo with Ocean Views - Maui Kamaole M205Welcome to your dream vacation retreat in Maui! This stunning 2-bedroom, 2-bathroom en-suite condo at Maui Kamaole M205 offers a perfect blend of modern elegance and island charm. The property features recently...
Kona Ocean View Suite - Walk to Shops and Dining
Welcome to our dreamy Kona getaway! This newly refurbished, luxury beachy retreat is designed for relaxation and convenience in the heart of Kailua Kona. Great for the Sunsets! Walking distance from Kona's best restaurants and bars, it provides easy access to Ali'i...
Kapalua Golf Villas Fairway View 1 Bedroom
Golf Villas Gold Fairway View 1 Bedroom- Situated along Kapalua’s Bay Course fairway- Fully equipped kitchen includes stovetop/oven, microwave, refrigerator, coffeemaker, cookware, tableware- Bedroom with 1 king bed or 1 queen bed- Queen sofa bed in living area-...
Condo in Princeville - Luxury Villa at Wyndham Bali Hai
Nestled high in the cliffs of Princeville, amidst the stunning scenery of Princeville on Kauai, Pahio neighborhood and Hanalei town beckon with a delightful array of restaurants, beaches, galleries, boutiques, and world-class golf courses, all within easy reach. Unwind...
1 Block from Waikiki Beach : Peek A Boo Ocean view
【Basic Info】This is a private studio room in Waikiki!!You can enjoy your stay by only yourself, family, friend or partner. The condominium is located east area in Waikiki.This area is really closed to the Diamond Head, Kapi olani Park.You can enjoy a walk while...
Kaanapali Alii | 164
Welcome to your serene getaway at Kaanapali Alii 164! This stunning two-bedroom, two-bath condo is designed to accommodate up to six guests, making it perfect for families or friends seeking a relaxing retreat. Step onto the furnished lanai and take in breathtaking...
Waikoloa Luxury 3BR + Ohana Suite w/ Ocean Views & Lanai — Hale Akaʻula
Hale Akaʻula – Waikoloa Luxury 3BR + Ohana Suite with Ocean Views & LanaiWelcome to Hale Akaʻula — your Waikoloa Village retreat for extended stays, family gatherings, and unforgettable island living. Set on Hawaiʻi Island’s sunny Kohala Coast, Hale Akaʻula is...
Relaxed Suite Near Shipwreck Beach + Parking & Pool Access + Kitchen
Experience oceanfront serenity with stunning views, spacious rooms, full kitchen, private balcony, and in-room laundry—ideal for couples and families. Snorkel nearby, hike the Mahaulepu Trail, or spot turtles at Poipu Beach. Relax in our large outdoor pool. Whether...
Laueki 8 – 4BR Hualalai Luxury Estate
Experience the epitome of luxury and residential living at Hualalai Resort with this very special property. Ideally located to optimize privacy and breathtaking panoramic ocean views, this gated 4-bedroom, 4.5 bath home has been meticulously designed and furnished to...
Home in the Sky!
Stunning brand new home with 3 bedrooms and 3 full bathrooms with beautiful views and absolute serenity. All new stainless appliances & new furniture, beautiful kitchen with granite and spectacular view and WIFI.!Wake up to the best sunrise on the island and enjoy the...
Royal Kahana Maui 108 Ocean View 1 Bedroom
- First floor condo with oversized patio- Vinyl plank flooring in living room, dining room, bedroom; tile in bathroom- Updated open kitchen with granite counters – fridge, stove/oven, microwave, dishwasher, cookware, tableware- Updated bathroom with granite counter...
Waipouli Beach Resort E303 Garden Mountain 2B/3B
Experience the beauty of Kauai from this spacious two-bedroom condo with scenic garden views. Surrounded by tropical greenery, it offers a peaceful setting to unwind and reconnect in the heart of the island.• Kitchen features granite countertops, Wolf cooktop and...
*New Building 2 bd/2ba Parking & Pool| 30 day min
Summary:**30 DAY MINIMUM**This spectacular 2 bedroom 2 bathroom city view apartment is a fully furnished retreat!Conveniently located in the stylish Waikiki neighborhood, just 15 mins from the Honolulu Airport (HNL) the apartment is near to many local attractions,...
Stunning Beachfront Condo at Hapuna Residences
Welcome to your dream escape on one of Hawaii’s most iconic beaches. This stunning 2-bedroom condo at Hapuna Beach Residences offers unparalleled ocean and beachfront views, all upgraded and modern decor, and direct access to the soft white sands of Hapuna Beach.B48...
Fabulous 5 bedroom for 10 townhome above famous Anini Beach!
Listing provided by "The Vacation Rental Experts". Contact directly for more options!This beautiful 5 bedroom, 5 bath for 10 offering, is situated right above famous Anini Beach, with an 8 minute walk down the Anini Beach trail just steps away from the property. Short...
Maui 3 Bedroom Townhome Sleeps 6
Please Send An Inquiry Before Requesting To Book By Clicking The Contact Host Tab.This memorable townhome is the perfect home base for your trip to Lahaina. With 3 bedrooms including 2 king beds and 1 queen bed, this beautiful property offers everything you need for a...
Ocean view private studio W/free reserved parking!
【Basic Info】This is a studio room in Waikiki!!You can stay with you friends, partner, family. This unit has ocean view. You can enjoy the view in your stayThis condominium is located west area in Waikiki.You can walk to Hilton village lagoon and beach and Kahanamoku...
1BR Mountain View w/ Balcony, Pool & 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...
Tranquil Ground Floor Unit Central Honolulu w/ AC
Honolulu is waiting for you at this awesome 1-bedroom apartment - ground floor unit. This quaint space features a cozy living room with a sofa bed, perfect for relaxing after a day of exploring. The bedroom boasts a comfortable queen bed, ensuring a good night's sleep...
Hawaiian Retreat Near Waikiki Beach – Cozy & Peaceful Stay! | Onsite Pool
Unwind in a spacious suite with private lanai, deep soaking tub, free WiFi, and plush bedding. Enjoy continental breakfast with Kona coffee, then stroll to Waikiki Beach or nearby shops. After exploring, relax by koi ponds or dip in the pool. Perfect for couples,...
New Listing! My Perfect Stays
Kaanapali Shores 732 is a Studio condo with central air conditioning that can accommodate up to 4 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...
Maui Ka’anapali Villas #515: One bedroom ocean view
Maui Ka’anapali Villas #515: One bedroom ocean view on N. Kaanapali Beach with Pool and Beach Access.This condominium is located on the 5th floor, and boasts magnificent ocean views. Sophisticatedly furnished with wood, tropical-themed elements, and art this suite was...
Kiahuna Plantation Resort 232 Royal Garden View De
- First floor end unit with lanai that walks out to the lawn- Bright and airy tropical ambience- Tile throughout unit- Fully equipped kitchen includes full size refrigerator, stovetop/oven, dishwasher, microwave, coffee maker, blender, toaster, cookware and tableware;...
Ocean Villa Emilie – Contemporary Luxury with Panoramic Views in Honolulu
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.Ocean Villa Emilie by Gather is a newly built,...
Palms at Wailea Garden Villas 1 Bedroom 2 Bath
Garden View 1 Bedroom 2 Bath Villa- Full kitchen includes stovetop, oven, microwave, refrigerator, dishwasher, coffeemaker, toaster, cookware and tableware- Spacious private deck- 1 king bed or 1 queen bed- Queen sofa bed- 1022 square feet / 95 square meters- Maximum 4...
The Westin Nanea Ocean Villas Resort & Spa, Pool!
Marriottu2019s Maui Ocean Club - Lahaina Villas is one of the most popular timeshare resorts - and for good reason! Kids and kids-at-heart will get a kick out of the resort's 3.5-acre super pool complete with a water slide, waterfalls, and children's area. The poolside...
The Blue Tide House: Steps to Maui beaches + nearby eats
Experience the best of Kihei, Maui from The Blue Tide House, located within the popular Kihei Kai Nani condos! Located on the first floor near the pool. Just steps across the street from the island's beautiful beaches, you can easily enjoy the sun, sand, and surf. A...
Brand New! Luxurious Sky Ala Moana 2 Bed 2 Bath
Summary:*30 DAY MINIMUM* Discover the lively heart of Honolulu and enjoy leisurely walks along the beach with this 2 bed and 2 bathroom apartment on the 16th floor of Sky Ala Moana. Get a charming view of the city and take advantage of the convenience of being close to...
Maui Kamaole One Beachfront Condo at Charley Young Beach
Discover your perfect Maui beachfront getaway at Kamaole One #9, this beautiful 2-bedroom, 2-bath oceanfront vacation rental located directly on Charley Young Beach, the north end of the world-famous Kamaole I Beach Park in sunny South Kihei.This rare oceanfront condo...
Coconut Plantation 1222-2: Tropical Villa w/ Lanai & Pool Access
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 Coconut Plantation 1222-2 by...
Lovely Modern Complex Directly Across Kam II Beach **NEW AC!
**Magnificent Upgrade as of August 2024 - As Brand New Split AC system with individual controls in both the living room and bedroom has been installed.**Escape to paradise with this beautiful and meticulously maintained ocean view condo, nestled on the 5th floor for...
Honua Kai Resort Konea 505 – Ocean & Sunset View 2BR at Kaanapali
Experience Maui's stunning west coast in luxury at Honua Kai Resort Konea 505, a spacious 2-bedroom, 2-bathroom condo perfectly positioned in the Konea Tower's serene interior courtyard. This premium retreat offers rare sunset views of both Molokai and Lanai, creating...
Maui Ka’anapali Villas #237: One bedroom 2 bath loft gard
Maui Ka’anapali Villas #237: One bedroom 2 bath loft garden view on N. Kaanapali Beach with Pool and Beach AccessThe space:Luxuriate in the lush garden and pool views in this Hawaiian oasis at the serene Maui Kaanapali VIllas. This condo offers indoor and outdoor...