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 Ocean View Studio at Kihei Akahi
Welcome to Kihei Akahi! This is the perfect location for your Maui vacation. Step cross the street and enjoy Kamaole Beach 2, one of Maui's best swimming beaches. The condo has a fully equipped kitchen, making it ideal to enjoy dinners at home. The lanai is perfect for...
Modern 1BD Condo with Pool Steps from Beach
Summary:Discover the allure of Maui with this chic and comfortable one-bedroom condo, a perfect retreat for those seeking both relaxation and adventure. Remodeled in December 2023, this fifth-floor gem offers stunning ocean views and is just steps away from the sandy...
Polished condo with Hawaiian decor
Welcome to Maui Parkshore 213, your tropical paradise retreat on the stunning island of Maui. This 2-bedroom, 2-bathroom condo is designed to accommodate up to 6 guests, offering a comfortable and stylish escape just steps away from the beach. Please note there are only...
Designer Condo in Hawaii Kai! Close to beaches, shopping, hiking!
Kick back and relax in this calm, stylish condo located in Hawaii Kai in east Honolulu. This newly redesigned condo is outfitted with brand new, high end furniture to match the allure of the beautiful, newly constructed building and fabulous amenities.This beautiful...
Designer-Amazing Ocean Views-Turtle Viewing Beach-Directly On Top of Ocean
Step into the island luxury of this brand new, fully remodeled 2nd-floor oceanfront studio vacation rental! Luxury and comfort all wrapped into one with ocean and island views, award-winning interiors, and access to a secret sea turtle beach. Endless ocean views from...
The Islands M2 Oasis at Mauna Lani Resort
Welcome to The Islands, your exclusive retreat within the luxurious Mauna Lani Resort! Nestled in a serene tropical oasis, our M2 townhouse invites you to experience the epitome of comfort and style. This 2-bedroom, 2.5-bathroom haven is ideal for up to 4 guests,...
Wailupe Seaside Haven: Beachfront Luxury Home w/ Pool & in City Proximity
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 Wailupe Seaside 4 Bedroom by...
CheCa Hale: Gorgeous Top Floor Corner Unit, With AC
Hopu i ka la ("catch the sun") at CheCa Hale! This airy, air conditioned, two-bedroom, two-bathroom corner penthouse is the perfect choice for family and friends traveling together. The home was beautifully and fully updated in 2022. Located in the beautiful Keauhou...
Updated ocean-view condo with 2 pools & hot tubs - walk to beach / dining
Maui Banyan H404Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'The beach is calling to you from across the street at this updated ocean-view condo. For endless sun-soaked leisure,...
Pahoa House with Lanai, Walk to Ocean!
Escape to the beauty of Pāhoa and experience the perfect balance of luxury and location at this 3-bedroom, 2-bath vacation rental. Situated 5 miles from Puna Kai Shopping Center, this home is a dream come true for adventurers and relaxation seekers. Immerse yourself in...
Mountain View Retreat Unit 1 - highly rated on leading rental sites!
Peaceful rain forest guest house a few miles from Volcano National Park. Mountain View Retreat is located in a lush and relaxing paradise. Enjoy your coffee or tea in the morning on your own private lanai. For larger parties there is another guest house on the same...
Mountain View Retreat Unit 2 - highly rated on leading vacation rental sites!
Peaceful rain forest guest house a few miles from Volcano National Park. Mountain View Retreat is located in a lush and relaxing paradise. Enjoy your coffee or tea in the morning on your own private lanai. For larger parties there is another guest house on the same...
Luxury Condo at Kameole Beach
Maui Banyan Resort is located a few hundred feet walk from 3 of the most famous beaches in Maui, Kameole Beach I, II, and III. Unit T106 is on the ground floor and is located at the back of the resort with garden views that appreciated for it's peace & quiet as well as...
Bamboo Canopy with Shared Bath and Common House
Escape to the enchanting Bamboo Canopy, a glamping-style retreat. This unique accommodation offers the perfect blend of rustic charm and modern comforts, making it an ideal choice for those seeking a tranquil yet luxurious getaway.The Bamboo Canopy features a queen-size...
KBM Resorts | FREE CAR | Wailea Beach Villa | Spacious 3-Bedroom Condo with Sweeping Ocean view! WBV-PH 412
** 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...
Luxurious BEACHFRONT Condo with Fabulous Ocean Views at Waikiki Shore!
Waikiki Shore #1102 – 2161 Kalia Rd.This 11th-floor beachfront condo is perfect for 2 couples, families, and friends up to 6 guests (STRICT MAX OCCUPANCY, using living room sofa bed). With spectacular views of the ocean, free parking, a full kitchen, in-unit...
Kailua-Kona Condo Rental ~ 1/2 Mi to Golf Course!
Escape to paradise at this peaceful 2-bedroom, 3-bathroom Kailua-Kona vacation rental! Boasting a full kitchen, a cozy living area, and a loft with a view, this property has all the essentials for a family retreat or a getaway with friends. Relax on the balcony while...
Walk to Beach from Lux Condo w/Hilton Pool Pass
When you stay at our 3/2 nestled between the Hilton and Marriot, you`re steps to the beach and a 5-10 minute walk to shopping, groceries, beach-front dining, a luau, a movie theatre and ancient ruins. The location simply does not get better in this resort area!Located...
Home with Panoramic Ocean Views + Private Pool
E Koma Mai (Welcome) to this upscale retreat that offers you a true luxury experience. Sitting on a hillside, this home boasts unobstructed views of the coastline from the main pool deck, upper lanai, and from nearly all interior spaces. With 3 bedrooms and space for 6...
Hale Pakika at Kukui'ula: Exclusive 5BR Estate with Private Pool, Golf & Ocean Vistas
Welcome to Hale Pakika at Kukui’ula by Gather, a five-bedroom, five-and-a-half-bathroom hideaway designed for up to twelve guests. Located off the first tee of the Kukui‘ula Golf Course in Koloa, this 3,500-square-foot single-level estate blends barefoot luxury with the...
NEW! Fully Renovated 1BR/1BA condo. Short walk to beach & Coconut Marketplace!
Welcome to your slice of paradise on Kauai’s beautiful Coconut Coast. This newly renovated 1-bedroom, 1-bathroom corner unit at Plantation Hale Suites is located on the ground floor for easy access and offers the perfect blend of comfort, convenience, and island...
Iconic Diamond Head and Ocean View in Waikiki!
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...
Island Glow Kailua Village, AC and ocean views in the heart of Kailua Kona
See whales, dolphins, Ironman Village and Ali’i drive from your very own lanai! Island Glow in Kailua Village is a beautifully remodeled 1 bed 1 bath condo with a brand new king bed and queen pullout sofa bed in the heart of historic Kailua Village. You will enjoy ocean...
Wai'ula'ula 330 - Upcountry Oceanview Residence
This discerning, upcountry, oceanview residence offers a great room with sliding glass pocket doors that invite indoor/outdoor island living; a chefs' kitchen outfitted with slab granite countertops and premium stainless steel appliances (including a wine refrigerator);...
2/2 Oceanview Modern Resort Vistas
Summary:Spacious and elegant. Completely remodeled in March 2024, no expense was spared to create our gorgeous oceanfront oasis. This two-bedroom, two-bathroom condo features luxurious touches paired with oceanfront serenity. Located in sunny Kihei, all of Maui is...
KM 131 OceanFront Ground Floor Condo w Pool AC Beach
Kauhale Makai 131 Island Style Updated 1Bedroom OceanFront Condo. Ground Floor for Easy Year-Round Indoor-Outdoor Living. Tropical Getaway to Relax and Recharge Aloha and welcome to our charming Maui getaway nestled on the ground floor of the Kauhale Makai Resort in...
Stunning ocean view 2 bedroom • Steps from beach
Enjoy beautiful ocean & sunset views from, Ohana Lani, a 5th floor condo with 1120 sq of living space and a stunning double wide lanai. The condo artfully blends modern amenities and island style. Ideally located in Kihei, the unit is right across the street from the...
Kaanapali Alii | 373
Kaanapali Alii 3732 Bedrooms | 2 Bathrooms | Sleeps 6 | Ocean View________________________________________Kaanapali Alii 373 is a luxurious ocean view vacation rental located in the heart of Maui's renowned Kaanapali Beach. This spacious condo over 1,700 square feet...
Kaanapali Alii | 155
Kaanapali Alii 1552 Bedrooms | 2 Bathrooms | Sleeps 6 | Ocean Front________________________________________Welcome to Kaanapali Alii 155, a two-bedroom oceanfront condo overlooking one of the top-rated beaches in the world year after year! Nestled along the pristine...
Kamaole Sands 4-411 - Modern, Ocean View, Split AC, Pool, Walk to Beach & Dining
Discover the ultimate getaway at Kamaole Sands 4-411, a stunning ocean-view condo nestled in the heart of South Kihei, Maui. This luxurious 2-bedroom, 2-bathroom retreat offers a perfect blend of comfort and style, accommodating up to 6 guests, making it ideal for...
POIPU RESORT, 2BDRM, F/K, Washer/Dryer, POOL, WIFI, daily fresh towel exchanges
ALOHA! This 2 bedroom, 2 bathroom condo is located in the beautiful resort called "The Point at Poipu", a family friendly resort.Gorgeous 2 BEDROOM, 2 BATHROOM (King in master and 2 Twins or we can request a Queen for the 2nd bedroom), OCEANFRONT RESORT, short walk to...
PARADISE RV.You won't forget your time in this romantic, memorable place.
Experience the magic of Maui on your terms! Our camper vans provide you the freedom to explore hidden beaches, wake up to sunrise on Haleakala. Tailor your Hawaiian adventure. Enjoy Maui beautiful!!!!
Maui El Dorado Kaanapali Beach Studio- G204, Maui El Dorado Kaanapali Beach Resort
New Property!!Located within the Maui El Dorado, this condo is surrounded by palm trees with a peek-a-boo view of the ocean. This is a 10-minute walk from the Whalers Village and restaurants and 1 mile from Black Rock Beach. There's a 3-night minimum stay.The complex is...
Waikoloa Beach Villas P2 Luxurious Paradise
Luxurious tropical island vibe. Relax and take in all Hawaii has to offer with fully furnished condo in walking distance to shops, restaurants, beaches and entertainment. The Space: Highly desirable location for both privacy and walking distance to many attractions....
Serene Hawaiian Eco Village 15 minutes from Hilo
Welcome to the Hawaiian Wildlife Habitat Eco Village, which is part of the responsible tourism effort to take care of the Aina (Mother Nature in Hawaiian). We offer an individual detached self contained bedroom (hexagon) with full bathroom and a kitchenette. To start...
3-Min Walk to Beach! Ground Floor - No Resort Fee
Just a 3-minute walk from the beach-cross the street and you're there from this first floor condo! Minutes drive to coveted Wailea beach and the area's best sunset views, shopping, and restaurants.★ No resort fee★ Private bedroom and bathroom★ Three beds★ Two full...
Beautiful Stylish Condo W/ Amazing Ocean Views, Walk To World Class Beach!
***Professionally Cleaned Condo, No-Contact Check-In/Check Out***Welcome to Kamaole Beach Royale #310, located in the heart of Kihei, Maui!. Enjoy a spectacular views of the ocean, beaches and neighboring islands in this recently remodeled condo!This condo has just been...
WBH D225 Aloha Ola2 – Relax in Oceanfront Paradise
Summary:This family-friendly beachfront, second floor 1-bedroom/1-bath air-conditioned Condo Suite comes with a comfortable king-size bed and living room couch that pulls out to a queen size sofa-sleeper allowing the unit to sleep up to 4 people. Just steps from the...
WBH D225 Aloha Ola – Ocean and Pool View
Summary:This family-friendly beachfront, second floor 1-bedroom/1-bath air-conditioned Condo Suite comes with a comfortable king-size bed and living room couch that pulls out to a queen size sofa-sleeper allowing the unit to sleep up to 4 people. Just steps from the...
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...
Great Location! Walk to Everything in South Kihei!
If you want to be close to it all - best beaches, best snorkeling, only surf spot in Kihei, SUP, kayaking, snorkel tours, dinner cruises, shopping, restaurants, nightlife - our recently updated, owner-managed (no dealing with unresponsive property managers) condo is the...
Sky Villa Estate: Luxury Gated Kona Retreat with Ocean Views
Welcome to your Hawaiian haven, Sky Villa Estate! Kick off your flip-flops and let alohaspirit guide you up the driveway to this secluded gated 5-acre estate, through lushlandscape that feels like a warm hug from the island itself. Deep lush lawns encouragefamily games...
Hale Mele 2 Panoramic Golf Course Views, Pool/Hot Tub, Golf Cart & E-bikes
Welcome to Hale Mele 2 — A Private Island Retreat of Elegance and ComfortDiscover the ultimate Hawaiian escape at Hale Mele 2, an elegant 5,100-square-foot, two-story luxury residence nestled within the prestigious Champion Ridge gated community on the Big Island’s...
New Upscale Kona Retreat, Ocean Views, Pool, BBQ
Welcome to paradise in Kailua-Kona, Hawaii! 🌴 Escape to this stunning 3-bedroom, 2-bathroom oasis boasting breathtaking ocean views and a private pool for the ultimate Hawaiian getaway. Wake up to the panoramic views of the Pacific Ocean right from your private lanai,...
Princeville Luxury Townhouse, modern with A/C.
Welcome to Villas on the Prince #28 a modern Princeville 3 bedroom, 3 bathroom condo situated in a private gated community that has AIR CONDITIONING in all bedrooms and main living areas. Recently updated. Sleeps up to 6 guests comfortably and within walking distance of...
Peaceful Big Island Homebase with Coastline Views
Experience Big Island aloha from your fully outfitted vacation rental house in Kaʻū, Hawaiʻi Island's southernmost district.• Punaluʻu Beach (black sand, 14 mi)• Ka Lae (South Point, 12 mi)• Hawaiʻi Volcanoes National Park (40 mi)Recharge back at your comfy 2-bed/1-bath...
Heart of Princeville w/AC minutes from everything!
Escape to our North Shore Kauai retreat in Princeville! A haven of beauty awaits you, with leisurely walks along Makai Golf Course offering breathtaking mountain and waterfall views. Experience mesmerizing sunrises, stunning sunsets, and starry nights in the tranquil...
Luxe Oceanview 2B2B Escape w/AC Near Beach & Shops
Summary:Location and Quality! You will feel the relaxed beach vibes from the very first step walking into this tastefully updated & beach luxe unit. Directly sit across the famous Cove surf spot & in the middle of all, you will be memorized by the ocean waves along with...
Modern Waikiki Beach Oasis w/ free parking
Aloha! This 550 sq ft 11th floor 1 bedroom in Waikiki Banyan is a relaxed, contemporary space designed to create special memories in a stylish, comfortable environment. With a city and mountain view from the lanai, this fully updated, air conditioned property is just...
Top floor oceanfront 2 bedroom condo, with expansive views
Welcome to Hale Mahina A406, aka The Fish Condo. This top floor oceanfront 2 bedroom, 2 bath condo boasts stunning views from your private lanai, living room, & even the kitchen. With your Maui memories in mind this condo has everything needed to feel right at home....