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.
Newly Renovation, All New: Beds, Furniture, Floors, Kitchen Counters and Island
This elegantly remodeled and redecorated, modern vacation home resulted from the collaboration of sophisticated and tasteful owners, and a world-class Maui- based designer. The contempory elegant touches and design fluidity will be above and beyond your expectation!...
Ocean front! 20' from water, downstairs unit. True beachfront, Pikake. No fees!
Escape to paradise with our ground floor condo at The Pikake in Maui! Enjoy the ultimate beachfront experience in this one-bedroom, one-bathroom retreat located on the desirable West side of Maui between Lahaina and Kapalua. With no deposits, resort fees, or check-in...
Royal Kahana 610 50%Off Last Minute April Deal at Remodeled OceanFront Condo
The Stice Team — Powered by Gather Vacations. Maui Born and Raised Professionals. Your Local Experts in Crafting Unforgettable Stays.Welcome to Royal Kahana 610, a rare sixth-floor corner 2-bedroom, 2.5-bath ocean-front sanctuary that stretches across 1,400 sq ft and...
HOKU'EA HALE Oceanfront Private Home with Hot Tub
Welcome to Hoku'Ea Hale, a very private oceanfront residence featuring spectacular ocean views, ocean entry and abundance of covered outdoor living space. Every room opens to the outdoor ocean, where you'll experience tropical paradise and unparalleled views of the...
Aloha Condos, Napili Bay Resort, Condo 110, Beach View
*******REMODELED******* Best Beach View Location! This is Hawaii the way you dream about it. No building taller than a tree on Napili Bay. Swim, surf, boogie board, stand up paddle, snorkel, seasonal whale watching and glorious sunsets without leaving the property.30...
Beach Cozy North Shore Turtle Bay Condo - Kuilima Estates East
Summary:Welcome to our little slice of paradise on the North Shore of Oahu, Hawaii. Our beach cozy condo is nestled in a well maintained gated community at the famous Turtle Bay Resort. Whether you are looking to relax or enjoy adventurous activities, this is the...
*Charming with OCEAN VIEW and Fully Renovated*Ideal Location
This FULLY RENOVATED cute condo is located near the amazing Kamaole Beach II, in the popular town of Kihei. With six endless miles of white sand, pristine ocean, delicious restaurants, farmers markets and craft fairs, this is the best location for your relaxing...
*Nani Kai Hale 507* Beachfront Maui Condo!
New Remodeled bathrooms! With breathtaking ocean views right on the beach, this 5th floor beautifully decorated unit offers full beachfront access. The master bedroom features a California king bed with a en suite tiled walk-in shower. There is also a sofa sleeper in...
Ka Eo Kai North Shore 2 BR
Wyndham Ka 'Eo Kai is nestled amid winding paths, tumbling waterfalls, bubbling streams and verdant gardens all overlooking Hanalei Bay. This resort feels more like an oasis hidden away from the tourist-crowded locales; a little bit of paradise hidden away in...
❤️PiH❤️ SOAK UP THE SUN VILLA ★ Free Hilton Resort Passes ★ Detached ★Gorgeous views ★
Brought to you by Paradise in Hawaii Luxury Homes.Soak up the Sun Villa is a quiet oasis in the KaMilo community overlooking Mauna Lani North Course with views of the ocean and Maui in the distance.We pride ourselves on providing some of the most sought after homes on...
Peaceful Big Island Hawaii Retreat with Private Beach Club Access
Our home is a classic Hawaiian style bungalow (no shared walls) 3 BR / 3 Bath (2 master ensuite) with attached garage parking. It's a space to relax, recharge and enjoy "island time". We have beach cruiser bikes, beach towels, snorkel gear, and paddle boards for your...
Aston Maui Ka’anapali Villas A109: Ground floor w/2 Br on N. Kaanapali Beach
Maui Ka’anapali Villas #A109: Ground floor 2 bedroom on N. Kaanapali Beach with Pool and Beach AccessThis condominium is located in the Aloha Tower, the central hub of the property. Situated on the coveted ground level, this unit boasts a full lanai, and affords easy...
Whale Watching Paradise from your Lanai—Lovely Oceanfront Condo!
BEST LOCATION AT PAPAKEA! No Resort Fees! Gorgeous oceanfront condo owner managed. Non-smoking. Our F Building oceanfront unit offers spectacular panoramic views of the blue Pacific and the islands of Lanai and Molokai. One of only a few true oceanfront condos available...
Kahala Seaside: Beautiful Nautical-Themed Home with Pool, Spa, Yard & AC
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 Kahala Seaside, a spacious...
🌺Lush Oceanfront Penthouse with Pool, Hot Tub, Mountain Sunrises, Ocean Sunsets
🌺Lush Oceanfront Penthouse with Pool, Hot Tub, Mountain Sunrises, Ocean SunsetsDiscounts for Extended Stays. Digital Nomads Welcome!Clean & Green Sleep Suite Beyond Luxury to Vibrance Thank you so much for considering A502 Maui Sunset for your Time, Energy and Money....
Quaint Studio in Heart of Waikiki
With its outstanding location in the heart of Waikiki, this studio apartment offers a comfortable and convenient stay. Be steps away from the ocean, yet central to restaurants, shops, and amenities. The high floor offers partial ocean views, along with mountain view....
Maui Resort Rentals: Honua Kai Konea 448 – XL 1BR w/ Partial Ocean Views, Only 1 Stack Back from Oceanfront!
Boasting a premier location in the closest one-bedroom column to the ocean at the entire Honua Kai Resort, Konea 448 offers fantastic vistas of the tranquil blue Pacific Ocean as well as views of Maui's neighbor island Lanai. Step outside onto the generous balcony and...
Cozy 1-bedroom condo in beautiful Koloa with WiFi, AC, fitness room
Welcome to Sunny Poipu Beach! This lovely 2nd floor unit at Kiahuna Plantation makes you feel right at home! Relax on your private lanai overlooking the garden while being steps to the sand. Surf spots, long walks and lifeguarded beach are at your fingertips. Fast...
Hapuna Modern House – Sleek Oceanview Luxury at Mauna Kea Resort
vrKCV - Hapuna Modern House, Professionally Managed by Kona Coast VacationsHapuna Modern House – Hawaiian Luxury Resort LivingPerched on the highest point in the coveted High Bluffs at the Mauna Kea Resort, Hapuna Modern House is a home like no other in Hawai'i....
South Kauai Tranquil Retreat w/ AC in Poipu
Waikomo Streams is a peaceful, tranquil, and beautiful property with immaculate gardens. Immerse yourself in a paradise garden view on the Garden Island! We have an updated, air conditioned unit that is quiet and comfortable. The property boasts tropical gardens, a...
Ocean View End Unit Condo #189 Bldg 29 -Free Wifi & Parking Pool Gym BBQ Grill
This beautiful end unit condo has been remodeled upstairs with new bamboo flooring, tile, and with an open kitchen design with granite, It is one of the few 2 bedroom units where you can experience the beach from your very own private lanai. We take pride in our unit...
KBM Resorts | FREE CAR | Molokai At Montage Kapalua Bay, Ocean view 3-Bedroom Penthouse with Daily Housekeeping, Spa!
** Limited Time Special Offer: Reserve any KBM Resorts property in Hawaii with an arrival date between now and December 31, 2026 for 6 nights or more and receive a FREE 4-door rental car from top providers--Hertz, Alamo, Avis, or Budget. Convenient airport pick-up and...
Wonderful retreat, Fantastic View, Immaculate, Beautiful, Private and Peaceful!
Enjoy gorgeous unobstructed ocean, marina & mountain views from our beautiful guest house. Located on the ridge, in a safe, quiet and upscale neighborhood in Hawaii Kai, East Honolulu, just around the corner from famous Hanauma Bay, Halona Blow Hole, spectacular Sandy...
Experience Tranquil Luxury at Pele's Last Resort, Holua Kai
The Hawaiian Islands are a true paradise on earth, with their stunning natural beauty and unique cultural heritage. Experience the tranquility of Hawaii's Big Island with a stay at "Pele's Last Resort". This three bedroom, two and a half bathroom vacation home is...
Turtle Bay Villa 217
jewelloceanvillas.com Enjoy the comforts of home in the Luxury Ocean Villa, 217. This second floor studio villa has an exceptional, unobstructed ocean view from your private lanai. This unit is only 60 feet from the beach and a two minute walk from the newly remodeled...
Five Star Inspired--NEWLY Remodeled direct Ocean Front!
Remodeled unit boasts kitchen with all new stainless steel appliancesgranite countertops,Enjoy and relax on the lanai marveling at the sweeping ocean views.Unit is so close to the water you can watch the turtles floating in the water below.Grab your swimming and...
You're Resort Home! Walk to Disney, Beach & Pool!
It can’t get any better than Hawaii resort living in Ko’olina! Make yourself at home in this beautiful, bright, fully equipped family home. There are plenty of comfortable work-friendly spaces & fast reliable WiFi. Soak up the sun at the pristine Ko’olina beach...
Ocean Views, Private Hot Tub, Swimming Pool Access, Historic Cottage
'The Cowboy House' is a very charming & historic home built by Plantation working families at the turn of the century.(1870''s!) This home offers three bedrooms and sleeps 6. It has been lovely restored and is a very special place to vacation in Hawaii. Soak in the...
Luxurious Condo on Ali’i Drive with Ocean view.
Complete your visit to the islands by staying in this Samoan-inspired 3-bedroom, 2-bathroom condo at Ali'i Cove. Featuring Polynesian interior design, the vibrant color scheme warms your spirits, setting in the reality that you are truly in paradise.Sip a freshly brewed...
Cozy Kona condo walking distance to the beach, shops and restaurants.
Beautiful, clean, cozy, recently updated Kona condo, your home away from home. Beaches, coffee shops, restaurants and boutique stores are all in walking distance. Includes all the essentials to make your stay comfortable and worry-free. In home amenities include:•...
Large Private Lanai with Ocean View
Congratulations! You've discovered Kamaole Sands, the best holiday complex in Maui. Now you have found one of the best units in the complex!Top 10 Reasons Why this Unit Is For You:1. Large Lanai-Far fewer than half the units in Kam Sands have a large lanai. Settle for...
Serene atmosphere with lush garden views
Welcome to Maui Kamaole K104, a tranquil oasis nestled within the heart of paradise. This ground floor unit, boasting 1 bedroom and 2 bathrooms, offers a haven of comfort for up to 4 guests, surrounded by lush garden views that inspire serenity and relaxation. From the...
☀Private Unit Like No Other ☀Serene, Tranquil, Fully Equipped ☀
☀Private Unit Like No Other ☀Serene, Tranquil, Fully Equipped ☀Your Tropical Oasis!! Please come enjoy what we believe is one of the best located units in Mauna Lani Fairways. Total privacy!! No Lanai facing yours, no building right next door. No road outside your...
*NEW Poipu 2BR Retreat|Pool|AC & Athletic Club
Discover luxury in the serene Poipu Beach Estates with our charming 2br/1ba cottage. Enjoy farmhouse-inspired design, full kitchen with KitchenAid appliances, and quartz countertops. Relax in A/C-cooled bedrooms or on the lanai. Exclusive access to Poipu Beach Athletic...
Wavecrest Resort Condo on Molokai
Wavecrest C109Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Find your island zen at this Wavecrest Resort condo. Just a short drive from the main part of town, this tropical...
Mahana 1205 OCEANFRONT PENTHOUSE 1 BDRM/2 BATH Condo/12th floor/Legal Rental
Mahana at Kaanapali is an OCEANFRONT resort located on the NORTH BEACH section of the famous Kaanapali Beach on West Maui. We are located just north of Duke's restaurant and several miles from the recent Lahaina fire. Our resort had no damage as a result of the Lahaina...
Ekahi 34F - Best Panoramic Ocean View!!
Wailea Ekahi 34F in Ekahi Village - A modern vacation escape.Our fully renovated condo with spectacular views has everything you need for your perfect vacation, located in the sought after area of Wailea on the island of Maui.Our condo features 2 master suites that...
Kona Condo with Ocean Views, Pool, A/C & Near Golf
Huaka’i Haven – Oceanview Condo Retreat Along the Kona CoastWelcome to Huaka’i Haven, a serene and stylish split-level condo perfectly located along the breathtaking Kona Coast of Hawaii’s Big Island. This 1-bedroom, 1-bathroom vacation rental offers 714 square...
Monthly- Discovery Bay 2203 Ocean/Sunset/Marina/City Views - Q Bed/Twin Sofabed
Sweeping Ocean Views High Floor Corner Unit, PremTV HBO, Remodeled. 5 Min to Beach, Ctrl AC, Furnished, Prking Incl, Spacious Lanai, Pool, HotTub, Utilities, WiFi, BBQ, Gym, Washer/Dryer, Beach Chairs/Boogie Board. Non smoking. Queen bed/Queen Sofabd.Sweeping Ocean...
Posh Oceanview Condo w/Resort Pool & Spa, AC & Spacious Lanai - Park Lane Palm
This fourth-floor luxury suite blends island sophistication with modern comfort in the heart of Oahu's coveted Kaka'ako neighborhood. With ocean and Great Lawn views, a spacious lanai, and curated resort amenities, Park Lane Palm Resort is designed for both relaxation...
KBR 3302 · Simple but Idyllic Oceanfront Resort w King Bed
Hotel Room at the Kauai Beach Resort located in Full Service Oceanfront Resort just 5 minutes from the Airport. This is a third floor unit with a sliding door to a lanai overlooking the Luxury Pool Area and direct access to the ocean. The Pool area includes several...
Wailea Elua Village 107 - 2 Bedroom Ocean View Condo
Located just steps from the beach in the heart of Wailea, Elua Village 107 is a beautifully appointed two-bedroom, two-bathroom ground-floor residence that offers the perfect blend of comfort and island elegance. With a spacious layout and tasteful décor, this...
Beachfront Retreat with Stunning Ocean Views at Hale Pau Hana on Kam II Beach.
Anchor Cove D2 is a single story property perched at the beachfront on the beautifully landscaped grounds of Hale Pau Hana Resort. Originally the resort restaurant, the building was reconstructed as a side by side duplex. Its prime location, large size, and proximity to...
EPIC location 20% off Jul/Aug-SPECTACULAR Home-Sunset,Ocean Views-Infinity Pool
Last-Minute Booking DiscountSave 10% when you book within 30 days of arrival.This discount is applied after any other promotional or rental discounts have been included in your rate.Take advantage of a great deal on a spontaneous escape!Mana Aina - “Spirit of the...
Beautifully Remodeled House In The Heart of Princeville - As Seen on HGTV!
Beautiful 4BR/3Bath single family home nestled in serenity. Feel your stress melt away as you swim, sunbathe, snorkel or surf at any number of stunning beaches nearby. Owners are highly rated VRBO/Homeaway veterans.Enjoy all the amenities of your home away from home:-...
Glorious ocean and Bali Hai views from this ground floor, air conditioned home
(Please note that we refurnished our home in November 2023. While the photos reflect the new furnishings and decor, the video shows the pre-November 2023 furnishings. Also please note that we changed the beds in the guest bedroom from a queen to two twin-xl beds. This...
2BR + Loft for the Price of 2BR and Golf Discount!
Welcome to our Beautiful Waikoloa Beach Condo-Penthouse with Discounted Gold Golf Membership & Fabulous Sunsets.This beautiful rental is a peaceful & quiet condominium (overlooking the 5th hole on the Beach Course, rated 18th nationally) and is within convenient walking...
Relaxing Oceanfront!
New owners Lisa and Scott are so excited to host you. "We want you to experience the best time ever on your Maui vacation. Our one bedroom, one bath, second floor condo has a magnificent and panoramic ocean view. This is one of the few places in Ma'alaea, where you can...
Stunning Beach Front Townhouse
Beautiful BEACH FRONT townhouse on Sugar Beach. 'Maalaea Surf is one of Maui's best kept secrets.' Spaciously spread over 5 acres of tropical gardens, Maalaea Surf sits directly on a beautiful white sandy beach which stretches for 5 miles. Beautiful sunsets and seasonal...
Kaanapali Royal Vacation Rental - Tropical Paradise with Stunning Views
Kaanapali Royal Vacation Rental - Tropical Paradise with Stunning ViewsLocation Highlights: • Prime Kaanapali location in a quiet, gated complex • Breathtaking golf course and ocean views • Large private lanai • Convenient access to Napili and Kapalua beaches,...