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.
Beautiful Kukui'ula Home With Great Lanai Space
New pool just added! This home has it all, private hot-tub, brand new pool, fire pit, 2,000 sqftlanai, and enough room for the whole family with over 3,000 sqft of insideliving space! - 5,000 soft totalThis home is special with it's open indoor/outdoor main living area...
Newly Remodeled Luxury Condo with Ocean and Fairway Views
Beautiful newly-remodeled unit in one of the most sought-after associations on the North Shore. We invite you to enjoy the peaceful, old-Hawaiian feel of Kauai’s North Shore and the upscale yet understated elegance of Princeville with a visit to our beloved home....
Sands of Kahana Resort #345 - Vacation West Maui
★ Completely Remodeled in 2025★Air Conditioned 2 Bedroom, 2 Bathroom at the World Renowned Sands of Kahana Resort★ Oceanfront Oasis in West Maui's Sands of Kahana Resort★ Huge Condo, 1,600 Sq Ft Property Highlights:Mesmerizing views of Moloka'i and Lana'i on the...
Ocean Front Condo with AC, Watch Sea Turtles from Our Lanai
Visit our remodeled ocean front get-away. The unit has been remodeled from top to bottom, from ceiling to floor. The master bedroom features a California King bed, night stands with reading lights, built-in cabinets for clothing storage, granite countertop, ceiling fan,...
Luxury Oceanfront Condo - Fabulous Ground Floor 3BR/2BA, Sleeps 6 - Lae Nani 511
At Lae Nani #511, you will feel truly relaxed, surrounded by lush tropical landscaping and listening to the soothing sound of the ocean’s waves breaking on the shore. The location of this three-bedroom suite is ideal, providing views of the ocean as well as gorgeous...
Heaven on Earth in Upcountry Maui
Welcome to The Star Lookout, a magical vacation cottage in Maui's Upcountry. Experience a taste of 'Old Hawaii' in our quiet, restful perch with privacy, sweeping views, magnificent sunsets, and oodles of stars. We are located at 622 Thompson Road, Kula, HI 96790.The...
Villas By The Cove, Plantation House · Dreamy Indoor-Outdoor Living Opposite a Sandy Beach
Welcome to a Cutting Edge Maui Beach Home that blends its Original 1940's Plantation Style Charm with Refined Contemporary Design and custom finishes. Located just steps away from sandy beaches on the desirable oceanfront Ili'ili Road, this romantic property mixes art,...
Glam Condo Located in Central Waikiki, Panoramic Ocean View, & Full Kitchen!n
♨ Glam Condo Located on the 42nd Floor With Panoramic Ocean View ♨Enjoy this fully equipt kitchen including a full-size fridge, wall oven, stovetop & dishwasher.✔ Located in Central Waikiki✔ 5 Min Walk From Shops, Restaurants, & The Famous Waikiki Beach✔...
Ocean Beach Home In The Heart Of Authentic Old Hawaii
STVR 19-360891, NUC 19-1179 From home to ocean in under a minute! This newly built custom home is just 200 feet from the ocean and located in the heart of authentic Old Hawaii - Captain Cook locale on the Big Island of Hawaii. An exceptionally comfortable residence,...
Beautiful Kapalua Oceanfront Retreat (989 sq.ft)
Wake up to the sound of waves and sweeping views of Molokai across the channel from this beautifully designed 1000 square foot one-bedroom villa in the Kapalua Bay Villas. Perfectly perched along the dramatic oceanfront cliffs, this ground-floor condo offers...
Pali Nui – Gorgeous New Kukui'ula Villa
Jaw-dropping, breathtaking, spectacular: sometimes even the highest superlatives can seem like low-key understatement. Pali Nui—this uniquely gorgeous new Kukui'ula villa—is distinctively designed and stylishly curated, with artful décor, tropical allure, and...
Puako Pau Hana, A Restful, Private Retreat located steps from the water!!
Puako Pau Hana is a great place to escape from all your cares! Located in the heart of Puako, you are literally just a few steps to the most beautiful little beach in Puako! Puako is known for it's magical old fashioned neighborhood feel and remarkable clear water,...
Bishop Suites at Executive Centre, 1-Bedroom Mountain View Suite + Full Kitchen
Unwind in Honolulu at this terrific condo. This cozy 1-bedroom retreat offers a living room with a comfy sofa bed, perfect for extra guests. Enjoy the convenience of amenities like a hair dryer, WiFi, washing machine, and AC. Relax in the gorgeous bathroom after a day...
Cozy cottage nestled on our 5 acre Organic fruit farm
The farm cottage is set at the top of our 5 acre exotic fruit farm. Enjoy your stay by touring the property and relaxing in our cozy home away from home. The cottage is equipt with everything you'll need without the clutter. From the living room, enjoy a view of the...
Ginger Room
Rejuvenate in the Rainforest at Ginger room, situated on 5 lush tropical acres in the heart of Volcano Village near Hawaii Volcanoes National Park. Our guests enjoy four spacious rooms with full walk-in closets, thick curtains, hardwood floors, and private bathrooms...
Hanalei Plantation Road Home - Dream Retreat with Pool & Ocean Views
Escape to this beautiful Hanalei Plantation Road home, nestled in a prized neighborhood. Enjoy sweeping mountain and ocean views over Hanalei Bay. With 4 bedrooms, a gym, pool, and ample indoor/outdoor space, it's a dream retreat. Upstairs, find a bright living/dining...
Pohinahina Place – Serene Hualalai Estate with Ocean Views & Private Pool
Pohinahina Place is your private resort retreat. With an incredible view of the Pacific Ocean and overlooking the 5th green of the Hualalai Golf Course, this property is located right in the middle of Hualalai Four Seasons Resort. This beautiful oasis is nestled on a...
Elua 1310 Ocean Front Condo - Family Managed - 50 Steps to the Beachfront/Walk!
(9/17/25) We just wrapped a full condo remodel of our oceanfront home and am bringing the unit back online!Elua 1310 is in the closest building to the beach with 120 degrees of unobstructed ocean views and sits next to the famous Wailea Beach walk.You are just steps...
Modern + Serene Oceanfront Napili Getaway W/AC - No parking or resort fees
Welcome to the Napili Point! This oceanfront 1 bedroom directly on the stunning Honokeana bay in Napili is a relaxed, contemporary space designed to create special memories in a stylish, comfortable environment. Freshly remodeled, this air conditioned property is...
Wailea Ekahi 14F - Best Views - 3 Minutes Walk to Beach
"Comfortable luxury with a magnificent view," wrote a recent guest. Wailea Ekahi 14F is an upper-floor 2-bedroom 2-bath condo. Situated in a quiet tropical garden setting in the center of Wailea Ekahi Village, far from road and pool noise, with one of the three "quiet"...
🏝️Summer Deals-Cute Studio across the Beach, pool, hot tub, wifi🏝️
This Studio has been recently renovated and furnished for your beach getaway. You have a view of the tennis court from the lanai, while enjoying your breakfast or morning coffee. The unit comes with air conditioner to keep you cool after a day at the beach. In the...
Charming. permitted cottage, short walk to Paia town & beach.nSTPH 2013/0004
Nestled on Baldwin Avenue, our plantation style one bedroom cottage provides convenient and comfortable accommodations for 2 people, with the amenities of Historic Paia Town and Paia Bay just a few minutes walk away and all areas of the Island within easy driving...
🌺 Fairways 1706 Tranquility Villa 🌺 Renovated, includes Beach Access, Bikes 🌺
Your perfect vacation begins here! The Fairways at Mauna Lani is a private gated community of quiet luxury condominiums, the famed Farimont Orchid Hotel and the Auberge Resort Collection. While relaxing, it is also close to the heart of Mauna Lani shopping, golf, spas,...
Downtown Luxury Penthouse, Free Parking, Washer/Dryer
Welcome to your stunning getaway in the heart of downtown Honolulu! This spacious, High-Ceiling two story Penthouse is perfect for families, large groups, or anyone looking to experience the best of the city with comfort and style. With 8 beds distributed across 3...
Ko Olina Beach Villas B1101: Breathtaking Ocean Views from Every Room
Discover the welcoming vibe of Ko Olina Beach Villas B1101, a beautifully appointed vacation condo that offers mesmerizing ocean views in the enchanting area of Kapolei, HI. With 1,500 square feet of living space, including a generous outdoor lanai, this home is...
Lavish Oceanfront Estate w/Pool, Spa & AC - Close to Beaches: Maunalua Sunset
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.Situated in the famed oceanside neighborhood...
Kolu Honu – Stunning Beachfront Condo for 2!
Summary:You’re so close to making the Hawaiian vacation of your dreams a reality, and at Kolu Honu, all the enchantment of the islands comes to life, beckoning you to a truly magical experience!The Space:You're just moments away from making the Hawaiian getaway of...
On top of the Ocean Hideaway - Mermaid's Palace on Maui
Welcome to Kaimana at Pohailani Maui! Enjoy amazing ocean views, sunsets, wildlife watching, and neighbor island views of Molokai and Lanai from this well provisioned condo located on West Maui. We are located so close to the ocean you could throw a stone into the...
Fantastic Oceanview Studio Condo - Complete Beautiful Remodel Unit 368
Consider this condo your home away from home while you visit Kailua-Kona. This cozy space offers a fantastic ocean view and serene atmosphere, perfect for unwinding after a day of exploring. With a living room featuring a comfortable queen bed, and comfortable love seat...
16B; Ocean View, Quiet Beachfront King Studio in Luxurious Wailea Ekahi Resort
Ocean View, King Bed, quiet Ground floor Studio condo, in the beautiful Wailea Ekahi Resort, near one of the 4 private pools and a short walk to the beach.Enhanced cleaning protocols and private ground floor entrance with Lanai opening onto the beautiful gardens and...
Lokomaika'i Kailua: Elegant Vacation Home with Pool & AC
On Oahu’s sun-kissed Windward side, Lokomaika’i Kailua (meaning “Gracious Kailua”) invites you to slow down, open the sliding glass walls, and let the island breeze transform everyday living into something magical. This single-level home blends open-concept...
Prime oceanfront 2 bedroom condo w/huge wrap around lanai
Welcome to Royal Kahana 210. This 1400 sqft, 2 bedroom, 2.5 bath condo features a massive wrap around lanai with unobstructed oceanfront views of the encompassing islands of Molokai & Lanai. Admire seasonal whale watching, sailboats, sea turtles, and sunsets from this...
Fabulous Location near Shipwreck Beach and Grand Hyatt Resort
We purchased this lovely ground floor garden view condo in April, 2013. This condominium has a large master bedroom with A/C. The master bedroom has an an en-suite master bath with a walk in shower. Our home also has a half bath for your convenience. Our spacious lanai...
Best Ocean Front Views on Maui! Whale Watch From the Lanai or Living Room!
Nestled in the heart of West Maui along the pristine Kaanapali Beach, the Mahana offers an unparalleled waterfront experience that few can rival. Located at the northern end of the scenic Kaanapali boardwalk, the Mahana offers an exceptional pathway suitable for...
Full Ocean View, Great For Whale Watching
It doesn't get any better than this: gorgeous, light, bright, breezy, full ocean view condo. Two wonderful lanais private and quiet. The perfect place to watch dolphins and whales play. Enjoy rainbows across Kauai's pristine mountains. While sipping your morning coffee...
Beautiful Top Floor Oceanfront #611 with A/C!
Paradise found! Unit #611 occupies the prime location at the Royal Mauian. It is on the top floor and centrally located in the building. This incredible vantage point provides gorgeous panoramic views of the ocean, beaches, mountains, and neighboring islands. At this...
Family Suite #1 - Two rooms w/ shared hot tub, Family suite # 1 - Ulu Retreat + A'ali'i Sunset Suite
Immerse in tranquility at our Ohia retreat with two serene rooms, each with its own private lanai for enjoying nature's symphony. Indulge in the comfort of 14-inch memory foam mattresses and flat-screen TVs. The courtyard, a blend of open skies and cozy corners,...
Oceanfront Corner Villa w/ Air Conditioning
Unparalleled oceanfront views make Unit 1, a highly sought after corner unit, at Poipu Kapili the ideal vacation rental for your dream Kauai vacation. Poipu Kapili is a boutique luxury complex in the heart of Poipu, just minutes from many popular beaches for snorkeling,...
Spacious Modern 2Bdrm Condo, Free Parking in Bldg., Full Kitchen, Sleeps 6.
Renovations were completed in March 2024. Everything is new. 6 can sleep comfortably, 7 when 1 or more are children.This condo is tastefully decorated and features a spacious living room with a comfortable sofa that opens to a full-sized bed, and a flat-screen TV. The...
Garuda Estate – Launiupoko Luxury Home
We invite you to indulge in this magnificent 3,300-square-foot villa nestled at the bottom of the Mountains of West Maui, Launiupoko. It's the first town off the bypass. A short 15-minute drive takes you into Ka'anapali. Whalers Village offers a golf course,...
Beautiful and Spacious Townhouse at Mauna Lani - Close to Beach
Enjoy the peaceful resort life in this beautiful townhouse with upgraded furnishings in the luxurious Kulalani at Mauna Lani community. With access to both the Beach Club and the acclaimed Kamilo amenity center, this stylish property is perfect for families or small...
Hale Anuenue By Parrish Kauai - AC & walk to Poipu Beach!
Perched on the rim of Poipu Crater overlooking Poipu Beach to the west and Mount Haupu to the east, Hale Anuenue ("house of rainbows") offers the perfect spot to see rainbows when the skies offer liquid sunshine. Positioned for views of the morning sunrise glow over the...
Luxury Ko Olina Beach Villa B109 by Gather w/ Stunning Ocean & Kapolei Views
Ko Olina Beach Villas B109 is a ground-level oceanfront retreat in Kapolei's Ko Olina Resort. With two bedrooms, two baths, and sleeping space for six, this villa blends comfort, luxury, and direct access to the lagoons, making it the perfect escape for families,...
Waipouli Beach Resort Exquisite Beautifully Decorated Extra Large Luxury
Newest Listing! Waipouli Beach Resort Exquisite Beautifully Decorated Extra Large Unit D310! Best of the Best! Ocean & Pool View! Central AC! Beach Chairs (up to 4) and Cooler!**Exquisite Luxury Condo of Distinction located at the World Renown Waipouli Beach Resort on...
Ikena Lani - Beautiful 5 BR House with Pool & Jacuzzi overlooking Kalihiwai Bay
Welcome to Ikena Lani, a luxurious modern custom home with breathtaking ocean views. Designed by award-winning firms, it offers a serene island retreat with hand-picked materials from Asia. The main house has 5 bedrooms, a spacious living room, kitchen, and media room....
Ocean Views W/Private Lanai - Kaha Lani 206
Castle Kaha Lani Resort #206, located on the second floor: One look inside this beautiful 1-bedroom/1.5-bathroom vacation condo, and you’ll see why it’s a favorite. The living room is decorated with modern tropical décor and attractive red accents and features...
Let's Do Sunset On Maui! 1 Minute Walk to Beach and Sunsets
Located just a 1 minute walk from white sandy beaches, stunning sunsets, & turtles on the beach daily, this island retreat is an ideal getaway. Your dream condo is centrally located in the heart of Kihei, Maui. This beautifully updated ground-floor unit offers easy...
Maui Resort Rentals: Honua Kai Hokulani 713 - Stunning Interior Courtyard 1BR Penthouse Gem w/ Gorgeous Ocean Views!
As the top-floor penthouse gem in the one-and-only column of inner courtyard 1br suites available at Honua Kai, Hokulani 713 is simply the best of the best among Honua Kai 1br suites. Enjoy gorgeous Pacific Ocean and Molokai views from this incredible 1br vantage point....
Maui Resort Rentals: Honua Kai Hokulani 738 - Luxurious 1BR w/ Partial Ocean & Mountain Views!
Hokulani 738 is a luxurious 7th floor one bedroom suite that offers views of the tranquil blue Pacific Ocean as well as views of the lush West Maui Mountains. You will have plenty of space to relax in the 700 sq. ft. interior. To fully enjoy the warm Hawaiian breeze,...
Ke Aloha Villa - 3BR Princeville Paradise with Lanai, Pool & Golf Views
All reservations require the main guest to review and sign a rental agreement to stay at Ke Aloha Villa.**Dearest Future Guests,**Welcome to your very own slice of paradise at Ke Aloha Villa in beautiful Princeville! As you prepare to embark on this adventure, we want...