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.
3BD Kauai Family Haven with A/C - Princeville, HI
🌴 Kauai Family Haven — Endless Bliss in the Heart of PrincevilleWelcome to Kauai Family Haven, a beautiful tropical retreat located in the heart of Princeville, a charming community known for its lush scenery and world-class golf. This thoughtfully designed home offers...
DELUX family friendly accomodations in charming Princeville.
Get ready to relax in this terrific 2-bedroom condo in Princeville. This serene retreat offers a king bed, a twin bed, and two bathrooms with master bath with a jetted bathtub. Enjoy the additional living space with a cozy sofa bed. Take advantage of the fitness room,...
Whispering Palms - Tranquility and Elegance
Summary:Spacious 4-bedroom home in Poipu’s Kiahuna Golf Village with air conditioning, a furnished lanai, home office, and complimentary Poipu Beach Athletic Club access. Quiet cul-de-sac setting just minutes from Poipu beaches, dining, and island adventures.The...
PM 301 Spectacular Direct Oceanfront Views Remodeled 1BD Convenient Location
Paki Maui 301 NEW LISTING Breathtaking Direct Ocean Views from this Fully Renovated 2Bedroom, 2Bathroom West Maui Condo FREE daily activities included with your stay value up to $570! Complimentary admission, every day of your stay*: Whale Watch (seasonal), Dinner...
NEW! Oceanfront Condo at Lawai Beach Resort
Welcome to our beautifully updated one-bedroom condo at the Lawai Beach Resort with AC! This is a wonderful opportunity to stay at one of the most sought after locations in the heart of sunny Poi'pu!The spacious living and dining area opens to your own private lanai...
Newly Renovated Top Floor Luxury Waikoloa Beach Villa F32, Fairway Views!!
Aloha and welcome to our beautiful 2 bedroom 2 bath villa located in Waikoloa Beach Villas.Our beautiful, gated villa overlooking the Waikoloa Beach Golf Course 3rd and 4th green and the King’s Lake, is our favorite place to vacation and we are confident you will find...
Reduced Beachfront 1-BR Apt in Kihei! n New Listing Special!
Oceanfront Vacation Rental in Central Kihei Unit #2Prime Location:Situated in the heart of Kihei, this family-owned and operated vacation rental sits at the northern end of picturesque Halama Street. The property is tucked away from the large resorts and crowded tourist...
Nestled in Unbeatable Location, offering a rare Combination of Comfort & Beauty
Nestled in an unbeatable location adjacent to the world-renowned 1 Hotel Hanalei Bay, Hanalei Bay Villa #1 offers a rare combination of comfort, convenience, and natural beauty. The sunset proximity to our Villa is highly sought after, some saying the sunsets are the...
Maui Kam J209: Your Tropical Oasis in Maui
Escape to this spacious 2-bedroom, 2-bathroom loft condo at Maui Kamaole J209. Featuring an open living area, large primary bedroom with King bed, and a guest room with a Queen and a Twin bed, this condo comfortably sleeps up to 6 guests. Enjoy the lush tropical gardens...
MK- D106: Convenient 1BR Condo, Lush Tropical Views
Embrace island living in this conveniently located, ground floor 1-bedroom, 2-bathroom condo at Maui Kamaole D106. The spacious open-concept layout features bedroom with a plush King bed with en-suite bath and a sleeper sofa for added sleeping flexibility. Enjoy your...
Oceanfront, Split AC unit, remodeled November 2024, king bed washer dryer unit
• Oceanfront• Split A/C units• King bed• Remolded November 2024• Beach access from condo complexFully remodeled in November 2024, unit 313 is a custom built, detailed, upscale condo welcoming you. You will find this bright, beautiful one bedroom, one bathroom oceanfront...
Lanai + Ocean Views: Secluded Holualoa Retreat!
Outdoor Dining | Fruit Picking On-Site | Short Drive to Snorkeling & BeachesSeeking a serene Hawaii escape? Look no further than ‘Lilikoi Inn!’ With stunning ocean views and a prime location just minutes from the shores of Magic Sands Beach, this 2-bedroom, 2-bath...
Dreamy Beachfront Home - Car & Parking Available
*** Aloha! Welcome to our happy place! ***** Newly Remodeled Coastal Retreat, with Floor-to-Ceiling Ocean View **Welcome to our beach house, where every detail has been thoughtfully designed by a professional interior designer to create a serene, luxurious...
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...
Hawaiian Style Escape – Pools, Water Activities, Golf, Shops, & Dining Nearby
Experience the Keauhou Resort Community: Your Hawaiian Escape in Kailua-KonaWelcome to our charming 1-bedroom, 2-bath condo in the beautiful Kanaloa complex. The cozy bedroom features a luxurious king bed, and the living room includes a convenient queen size Murphy bed...
2 BDRM w/ 4 Beds + 2 Bath + Parking + Partial Ocean View, 2 mins walk to Beach
Legal vacation rental at a fabulous location! This renovated 876 sq ft, 2 bedroom 2 bath with 2 balconies home is across from ‘Alohilani Resort, Steps away from the Waikiki Strip (Kalakaua Ave) and Waikiki beach! There are endless shopping, dining, and activities within...
Luxurious Poipu condo - Walk to multiple beaches - Central AC - Wifi - Pools
Welcome to your slice of paradise in Poipu!Nestled in the prestigious Regency @ Poipu Kai Resort, our newly furnished, air-conditioned, 5-bedroom luxury condo offers an oasis of comfort and elegance on the beautiful island of Kauai. Perched on the 2nd and 3rd floors,...
Kona Reef: B-15: Direct Beachfront, Pool/Hot Tub, Air Conditioning, Elevators
*This unit will not have Lanai Access during 1/2/2026 - 2/2/2026 for Spalling Repairs, The rates for this time are being discounted by 50% for this inconvenience.* Located on the second floor, Kona Reef#B-15 offers stunning year-round views of golden sunsets and easy...
Hawi Hideaway- A Jungle Oasis
Come enjoy the peace and serenity of this property located just steps away from historic Hawi town.Hawi Hideaway is set back in a quiet cul de sac, surrounded by trees to feel like you are staying in a jungle. Enjoy the sounds of Hawaii with the roosters crowing in the...
Kaanapali Alii | 4114
Kaanapali Alii 41142 Bedrooms | 2 Bathrooms | Sleeps 5 | Ocean View________________________________________Kaanapali Alii 4114 is a stunning diamond-rated two-bedroom ocean-view vacation rental that offers a luxurious retreat on Maui's renowned Kaanapali Beach. Spanning...
Hale Ohana Hau'oli - Charming Kukui'ula Villa with Geometric Pool + Spa!
From the striking stone-pillared entry to the enchanting backyard banyan tree, this delightful Kukui'ula villa radiates an irresistible island-style ambience. Indoors and out, Hale Ohana Hau'oli teems with beautifully curated details: tasteful contemporary furnishings...
Kaanapali Alii | 265
Kaanapali Alii 2652 Bedrooms | 2 Bathrooms | Sleeps 6 | Ocean View________________________________________Welcome to Kaanapali Alii 265, your dream vacation rental in the heart of Maui’s renowned Ka'anapali Beach. This luxurious two-bedroom paradise combines modern...
Kaanapali Alii | 255
Kaanapali Alii 2552 Bedrooms | 2 Bathrooms | Sleeps 6 | Ocean View________________________________________Kaanapali Alii 255 is a stunning two-bedroom, two-bathroom ocean-view residence that features a warm and inviting contemporary design. This spacious vacation rental...
Kaanapali Alii | 234
Kaanapali Alii 2342 Bedrooms | 2 Bathrooms | Sleeps 6 | Garden View________________________________________Welcome to Kaanapali Alii 234, a beautifully renovated one-bedroom garden view condo with a fully enclosed den that comfortably serves as a second bedroom. Relax...
Tropical oceanfront escape, steps from Sugar Beach
Discover tropical relaxation at Sugar Beach 233, a 1-bedroom, 1-bathroom, 2nd-floor oceanfront condo that offers breathtaking views of the Pacific from your private lanai and central A/C. This resort has elevators for easy access. Unit 233 can accommodate up to 4...
🏝️SUMMER Special -Ocean View Renovated Condo in Napili🏝️
This one bedroom/one bathroom condo has been remodeled from top to bottom and beautifully furnished with clean modern design, perfect for your Maui getaway. The lanai has sitting area to enjoy morning coffee or sunset cocktail overlooking the water and the island of...
🏝️SUMMER Special-Renovated Golf, West Side Getaway🏝️
This two-bedroom/two-bathroom condo is perfect for any getaway. Whether you are looking to play golf at the world class Bay and Plantation Course, relaxing and romantic getaway with going to the spa at Montague or Ritz Carlton, enjoying wonderful restaurants at Sansei...
🏝️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...
Hale Kai - Large Enclosed Lanai - Sleeps 2
Hale Kai - Spacious Enclosed Lanai - Sleeps 2Welcome to Hale Kai, your “Home by the Sea” in the charming Kuilima Estates East community. This beautifully designed island-style retreat offers 875 square feet of living space, including a large enclosed lanai, perfect for...
Hale Kahakai - Oceanfront Retreat - Direct Beach Access - 30 Day Rental
Important Notice: This property is available for rental with a minimum stay of 90 consecutive days. Rental prices remain fixed and are not subject to reduction based on the length of stay.Welcome to Hale Kahakai! This exquisite single-family oceanfront retreat is...
Ocean View Paradise: Spacious 2-Bedroom Condo at Kaanapali Shores
Experience the ultimate Maui getaway at Kaanapali Shores 416, a beautifully maintained 2-bedroom, 2-bathroom condo that promises breathtaking ocean views. The open-concept living space seamlessly blends indoor and outdoor dining, making it easy to savor meals while...
Inspired 1-BR, Magic Gardens, Stream and Waterfall
Hit the pause button and relax at our peaceful stream side retreat. Located next to the Waipio Lookout, our Hamakua Coast rain forest property is the perfect place to recharge and rejuvenate. Hear the rush of our waterfall and enjoy our private oasis. We’re a ten minute...
Indoor-Outdoor living for three
Beautiful Indoor-Outdoor living for three at our peaceful stream side retreat with private gazebo. Located next to the Waipio Lookout, our Hamakua Coast rain forest property is the perfect place to recharge and rejuvenate. Hear the rush of our waterfall and enjoy our...
New Listing w/Discounted Rates! Escape to paradise with 180-degree ocean views and magnificent sunsets year-round!
Property Highlights • Remodeled luxury villa in one of the Kapalua® Resort’s most coveted locations, offering 180-degree ocean, island and sunset views! • Expansive lanai, ideal for winter whale watching and outdoor living at its very best • Spacious living room is...
Westin Kaanapali Ocean Resort: Two bedroom villa oceanview, sleeps 8!
Westin Kaanapali Ocean Resort: Two bedroom villa oceanview, sleeps 8!Available Sunday December 29 - Sunday January 5Beautifully equipped two bedroom, two bathroom villa with oceanview with full kitchen AND kitchenette. Rooms can be separated for two families to share,...
New Listing Specials! Walk to Beach. Sleeps 6. Fantastic Resort Amenities.
Centrally located in Kihei and a three minute walk to Kamaole Beach, where you'll have access to some of the area's best snorkeling, whale watching, and sunsets. Short drive to coveted Wailea beach!★ Ocean View★ Private bedroom and bathroom★ Two full bathrooms★ Three...
**Fairways Mauna Lani #1606 - Luxurious 2-Bedroom Retreat: 2 King beds, Remodele
**Fairways Mauna Lani #1606 - Luxurious 2-Bedroom Retreat: 2 King beds, Remodeled with Spa-Like Bathrooms, Steps from the Pool!**Please scroll down for detailed informationWelcome to your dream getaway! This beautifully remodeled 2-bedroom, 2-bathroom townhome is...
Hanalei Bay Resort 4303: Oceanview w/ Lanais & Resort Perks, Pools & Tennis
Welcome to Hanalei Bay Resort 4303 by Gather, a stylish one-bedroom, one-bathroom condo perfectly positioned on Kauaʻi’s breathtaking North Shore. Overlooking Hanalei Bay and the Na Pali Coast, this bright and spacious suite blends island charm with resort luxury — an...
Hanalei Bay Resort 4301: Oceanview w/ Lanais & Resort Perks, Pools & Tennis
Welcome to Hanalei Bay Resort 4301 by Gather, a serene one-bedroom, one-bathroom condo perched above Kauaʻi’s breathtaking North Shore. Overlooking Hanalei Bay and the lush Na Pali Coast, this peaceful island retreat is perfect for couples or solo travelers seeking...
Ocean Views from Every Room! Hawaiian Heaven
Summary:Cozy, sunlit private room 🌞 in a stylish home near cafes, dining, and public transport. Enjoy a comfy bed, spotless shared spaces, fast Wi-Fi, and a welcoming host with great local tips. Ideal for solo travelers or couples seeking comfort, convenience, and...
Honu Hale Waikiki: 2BDR Spacious Panoramic View
Experience a unique Hawaiian getaway in our 2BD/2BA spacious condo in the heart of Honolulu. Enjoy stunning panoramic city and ocean views through floor-to-ceiling windows and relax on two private lanais. With ensuite bathrooms, a fully-equipped kitchen, and modern...
Waikiki Beach Studio Condo..Minutes to Beaches!nGreat Value.
Aloha and welcome to the ideal Waikiki studio Condo rental getaway in Waikiki...just a short stroll to incredible beaches! Ideally located at the start of Waikiki, near the marina, we are close to everything for your vacaction getaway. World-class shopping & wonderful...
Spectacular, Modern, Coastal, Ocean Front Studio in Napili Shores A102
Newly Remodeled Luxury, Modern, Coastal vibe ocean front studio in Napili Shores (A102). Welcome to this gorgeous condo in Lahaina overlooking Lanai, Molokai and Napili Bay. This luxury modern studio features a living room with 1 king bed and 1 twin sofa bed, perfect...
Kihei D-202-Oceanview Condo! Right Next to Dining and Shops
*Panoramic Ocean and Sunset Views*So Very Close to Dining, Shopping and Beaches*Large, Fully Equipped 1 bed, 1 bath CondoExperience the perfect Maui getaway in our stunning 1 bedroom, 1 bathroom condo at Kihei Alii Kai D202. Boasting breathtaking ocean views and...
Across from the Beach - Sunsets, Ocean and Turtles
Puako Beach Condos - Unit 210: Your Hawaiian Getaway Awaits!Escape to paradise at this newly remodeled 3-bedroom, 2-bathroom end unit in the heart of Puako, just steps away from a pristine white sand beach. Whether you`re seeking relaxation or adventure, this beautiful...
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...
Stylish Waikiki 1 Bedroom Gem with Parking
30-Day Rental Only!Kick back, relax in this stylish, newly remodeled space in quiet Waikiki. Charming 1-bedroom apartment featuring fully-equipped modern kitchen and bathroom, and air-conditioned bedroom for restful nights. Perfect for solo travelers or couples with...
Waikiki Surfer's Paradise! Classy Studio w/Parking
Waikiki surfer's paradise on the 22nd floor of the Marine Surf. This unit is fully equipped with what you need to relax after a day of surfing, sightseeing or beach fun. The west facing lanai boasts partial ocean, city and mountain views. On Friday nights enjoy the...
Dazzling Waikiki Studio+KIng Bed
See reviews at airbnb.com/h/ms2011.This amazing studio has been fully renovated and tastefully decorated for a bright and airy atmosphere. Features a king-size bed, full kitchen, large shower, and the essentials for a comfortable getaway.Enjoy great views of the ocean...
Uncle Richard's Waikiki Beach Studio w/Parking
Soak up the island vibes from this bright, breezy studio just a short stroll from Waikiki Beach. Nestled among vibrant shops, local eateries, and island nightlife, this modern retreat features a private lanai, fully equipped kitchen, fast Wi-Fi, and free assigned garage...