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.
Kaanapali Alii | 214
Welcome to Kaanapali Alii 214! This is a beautiful one-bedroom, two-bath garden view residence has an additional enclosed sleeping den and large garden view lanai. The primary bedroom has a king-sized bed, wall-mounted smart TV, and offers access to the lanai. The...
The Grand Islander, a Hilton Grand Vacations Club - 1 Bedroom - Mountain View - 1DR
*** Sanitation/Cleaning Update ***We understand that our guests’ expectations for hotel cleaning and disinfecting have changed. That’s why we’ve taken additional measures beyond our industry-leading cleaning standards by partnering with RB, maker of Lysol &...
Waikiki Banyan T1-19th Fl / King Size Bed
Please be informed that the Waikiki Banyan recreational deck and all associated amenities will be closed for renovation starting April 7, 2025. The renovation process is expected to take approximately 12 to 14 months.Notice - Recreation Deck Work (July 28 -...
KBM Resorts | FREE CAR | Kapalua Golf Villa | Ocean view | 2-Bedroom Condo, Recently Remodeled! KGV-24P2
Luxurious 2-bedroom end-unit golf villa with panoramic ocean and sunset views, modern upgrades, and spacious lanai-perfect for relaxing in style and soaking in the beauty of Maui's west coast.** Limited Time Special Offer: Book any KBM rental home in Hawaii for 6 nights...
Short walk to Kailua Beach across the street-Quiet AC's-Lg. Kitchen-Patio-Grill
Live the beach life! An opportunity to live across the street from Kailua Beach Park, with the perfect combination of sandy beach, large grassy areas, tall ironwood trees, and turquoise-blue waters. You will love this generous ground-level one-bedroom, one-bathroom...
Puka Pa 4 – Hualalai Luxury Estate
This new expansive estate in the Puka Pa neighborhood is located just 6 minutes to the heart of Hualalai. Five bedroom suites wrap up to 10 guests in bright, modern luxury, featuring natural wood and stone throughout. Expansive indoor and outdoor kitchens, vaulted...
Family & Friends Getaway! 3 Great Units for 12!
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...
Kiahuna Plantation Resort Partial Ocean 2 Bedroom
Partial Ocean View 2 Bedroom 2 Bath- Spacious split-level condo with lanai features full kitchen include stove, oven, microwave, refrigerator, dishwashwer, coffeemaker, cookware and tableware- Walk-up, no elevator- Sofa bed in living area- Rollaway bed 20 USD per night-...
Kiahuna Plantation Resort 71 Ocean View 1 Bedroom
- Second floor end unit with lanai overlooking the twin bridges and out to the ocean- Walk-up, no elevator- kitchen includes updated appliances, granite countertops and backsplash, microwave, full size refrigerator, dishwasher, coffee maker, blender, toaster, cookware...
April SALE-9,10,14,15 SALE 159-TreeHouse Vibe AC-WiFi-BBQ-W&D-Cliffs-Sleeps 6
Casa by the Sea Welcomes you.Relax in Paradise with 1 acre of Tropical Jungle to explore and the sounds of the Ocean,Birds & Frogs. 5 Min short walk to Paradise Cliffs & Parks. COME SEE THE ONLY HAWAIIAN ISLAND WITH AN ACTIVE VOLCANO. 15 min Drive to Mackenzie State...
Westin Ka'anapali Oceanfront Center studio, sleeps 4, Heavenly bed, 3/8-3/15/25
This studio unit in Lahaina, perfect for your escape to paradise. This is a timeshare but is also a hotel that is managed by Marriott. Check prices with the hotel to see what a bargain this price is for our oceanfront center units. Oceanfront studios run $900+ per night...
Waimea Bay Tropical Retreat w/ pool & jacuzzi 2 min walk from the beach!
Waimea Bay Tropical Retreat is in a Great Location on a private residential cul-de-sac within walking distance to Waimea Bay, Three Tables, Sharks Cove, Foodland, Food Trucks. Close to the bike path & all of the best North Shore surf breaks & beaches. Neighborhood is...
Spacious Family Suite, Stunning Mountain View-1 Bd. Marriott's Ko Olina Beach
Cozy yet spacious. Intimate yet extensive. This one-bedroom features luxurious comfort for memories together and space to escape.Mountain View One Bedroom Villa, 1 King, Sofa bed, Full kitchen, Microwave, 920sqft/83sqm, Living/sitting area, Dining area, Separate...
Marriott Kauai Lagoons - Kalanipu'u - Luxurious 2-Bedoom - Beachfront resort - Family Friendly
Come experience Kauai at this luxurious Marriott overlooking Hawaii's blue waters. This oceanfront resort offers nature lovers and adventurists the ultimate vacation. Surrounded by sparkling lagoons, beautiful waterfalls, and a wildlife refuge make sure you don't forget...
Pu'ukole 28 – 4BR Hualalai Luxury Home & Guest House
This 4 bedroom, 4.5 bathroom home, features stunning views and unparalleled outdoor living. This secluded and tranquil retreat in the Puukole neighborhood is situated on the 13th hole of the Keolu golf course and features captivating and expansive ocean views. Sunsets...
Charming 2BR Retreat in Wahiawa Close to Botanical Gardens and Surf
Your Central Oahu Adventure | 2BR All-Access BasePERFECT FOR:Couples | Families | Surf lovers | Hikers | Pet owners | Digital nomadsAccessible Location:- Close to North Shore – Haleiwa, Pipeline, Sunset Beach- 5 minutes to Dole Plantation- Easy walk to local cafés &...
Ultimate Hawaiian Escape With a 2-Bd L/O Villa at Westin Ka'anapali Ocean Villas
Experience the ultimate Hawaiian escape with a 2-Bedroom Lockoff Villa at Westin Ka’anapali Ocean Resort Villas, a luxurious haven on Maui’s famed Ka’anapali Beach. With breathtaking views, endless amenities, and a prime location, this villa offers the perfect...
Beautiful 2-bedroom condo on the ocean with WiFi, AC, fitness room
Many recreational amenities, including an outdoor pool, a sauna, and a fitness center. Additional amenities at this resort include complimentary wireless internet access, concierge services, and a picnic area.Enjoy Honu Cove Bar & Grill serving guests of Hilton Vacation...
Ko Olina Vacation in this Beautifully Furnished, 3 bedroom 3 bath (KoK-1035D)
One Rate, You Choose the Length of Stay!All rates quoted will be based on a 30 day period. Our monthly rentals will be made available to you for your use and occupancy for a period of thirty (30) days. You are not required to stay for a full 30 day period. Just stay for...
Lodge at Kukui'ula Bungalow | 1A
Kukui'ula Bungalow 1A is a beautiful one-bedroom bungalow at The Lodge at Kukui’ula on Kaua’i. It offers luxurious accommodations and exclusive access to the award-winning private club facilities and amenities of The Club at Kukui’ula, including the 18-hole Tom...
26F Partial Diamond Head & Ocean view Waikiki 1BR w/ 1 Free Parking!!
Your vacation getaway, just a quick stroll to the beach! This 1 Bedroom /1 Bath /1 Free PARKING included! Sleeps up to 4 guests. All 3 Brand NEW Beds (July 2022) - 2 x Full Bed in the Bedroom and 1 x Queen size sofaBed in the Living Room.Great location! Just two blocks...
Stunning Partial Ocean Views - Kona Bali Kai 167
Kona Bali Kai 167: Explore downtown Kailua-Kona easily from this comfortable ocean-view location. Upon entry, guests will see the crisp blue views from the floor-to-ceiling glass doors. Tile flooring and charming light rattan furniture compliment the main living space....
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...
Spacious 2-Bedroom, Perfect Location In Wakiki, Located Near The Beach, Shopping
This condo is located in the Discovery Bay. Enjoy the conveniences of home while you are away, the condo is fully furnished with cookware items, central AC, washer + dryer, FREE WIFI, cable TV, local phone service and a spacious lanai for you to watch the sun set. With...
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...
Wyndham Kauai Beach Villas | 1BR/1BA King Suite
Summary:The Coconut Coast in Kauai is the perfect backdrop for your island adventures. Plus you can choose how urban or outdoorsy your trip will be. Enjoy the benefit of a beachfront resort location with convenient access to the island’s largest city.Wyndham Kauai...
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...
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...
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
FREE daily activities included with your stay value up to $570! Complimentary admission, every day of your stay*: Whale Watch (seasonal), Dinner Sunset Sail, Snorkel Sail, Alpaca Farm Tour, Pineapple Farm Tour, and All Day Electric Bike Rental. (W1)*One ticket per...
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...
Long term rental in Kakaako
Beautiful 2 bedroom & 2 bath located in the heart of Kakaako is available for long term rental.Fully furnished with internet and utilities included.30 day minimum rental, no exceptions$13,600/month
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...
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...
Westin Nanea Ocean Resort Villas - Resort View
This Lahaina hotel suite boasts 2 inviting bedrooms with 2 king beds. Enjoy the wonderful amenities like WiFi, fitness room, and a cozy living room with a queen bed. Relax in the enchanting bathtub or dry off with the provided hair dryer. Experience the magic of Lahaina...
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...