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.
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...
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...
Sunny Kona Coast 2BR Condo with Pool & Balcony
Located on Kona Coast in Hawaii, this tropical garden resort is less than one kilometer from Kahaluu Beach. It features a restaurant, tennis court and villas with a fully-equipped kitchen. The resort has 2 outdoor pools, 3 hot tubs and a sauna.Kona Coast Resort offers...
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 perfect home base for exploring beautiful Oahu!PERFECT FOR:Couples | Families | Surf lovers | Hikers | Pet owners | Digital nomadsAmazing Location:- Close to North Shore – Haleiwa, Pipeline, Sunset Beach- 5 minutes to Dole Plantation- Easy walk to local cafés &...
12th Floor Beachfront Studio at Sans Souci, Sleeps 4, Smart TV & WiFi access
Sans Souci Gold Coast Beachfront location, this studio is a dream. With a cozy living room featuring 1 queen bed and 1 sofa bed, guests can unwind in style. The bathroom offers a refreshing shower and a hairdryer for convenience. Fantastic amenities like WiFi, a...
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...
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 By Parrish Kauai
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...
Enjoy a Hassle-free Stay! 2 Comfortable Units, City View, Pets Allowed, Pool!
Spend some time at our magnificent hotel and treat yourself to a unique experience. Here is where you start your journey to indulgence and relaxation. Explore the excellent selection of amenities that are waiting for you, and get ready to be pampered. Lie back and soak...
Marriott Ko Olina Beach Club - On The Beach- Family Friendly - Mountain View
Come experience Hawaii at this premium level Marriott Resort in Oahu. With luxurious amenities and great family entertainment, your family won't want to leave.This property has everything you need for a tropical vacation. There is a lagoon style family pool with...
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...
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...
Waipouli Beach Resort E303 Garden Mountain 2B/3B
- 3rd Floor Condo with Balcony- Elevator access to all levels- Fully equipped kitchen includes granite countertops, Wolf cooktop and convection oven, microwave, dishwasher, full size Sub-zero refrigerator, coffeemaker, blender, toaster, cookware and tableware- Master...
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...
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...