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.
Kaanapali Alii 11111 Bedroom | 2 Bathrooms | Sleeps 4 | Partial Ocean View_________________________________________________Welcome to Condo 1111 at the Kaanapali Alii Resort, a stunning 1-bedroom with a partial ocean view overlooking the turquoise waters of Maui’s famed...
Hanalei Bay Resort 4302: Oceanview w/ Lanais & Resort Perks, Pools & Tennis
Overlooking the legendary Hanalei Bay on Kauai’s lush North Shore, Hanalei Bay Resort 4302 offers an inspiring island retreat with sweeping ocean, mountain, and Na Pali Coast views. Designed for couples or solo travelers who crave both tranquility and connection, this...
KBM Resorts | 4 Free Cars | Mahana | Upgraded and Remodeled! | 4 Units, 7 Bedrooms | MAH ML-3890
** 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...
Oceanfront condo with pool, hot tub, sauna, tennis, BBQ, putting green, & lanai
Pono Kai Resort A308Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Escape to your dream vacation and make yourself at home in this magnificent top-floor oceanfront condo, offering...
Hualalai 4 bedroom 5 bathroom privacy, central to all Four Seasons amenities
Make yourself at home in this 4-bedroom Kailua-Kona house. The space offers five bathrooms, providing plenty of privacy and comfort for guests. Step inside to find a pleasant environment where air conditioning keeps things cool and a hair dryer and iron add convenience...
The Cliffs at Princeville Resort, Tennis Courts
You’ll love the stylish decor of this charming place to stay. Located on the north shore of Kauai, The Cliffs at Princeville lies within the Princeville Resort on over twenty acres of lush tropical land. This dream of a resort overlooks the Pacific Ocean from atop a...
Oceanfront Poipu Pool Home - Fabulous 7 BR Estate
This beautiful 7 bedroom for 14 oceanfront pool home is only 75 yards to famous Brenneckes Beach! Enjoy uninterrupted sunrise and sunset views from your oceanfront pool and jacuzzi. Enjoy the playfulness of breaching whales and spinner dolphins by day and the quiet calm...
** 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...
New Listing! Paniolo Club, Ground floor, BBQ, WIFI by Coldwell Banker
Welcome to the Big Island Paniolo Club 114, a stunning two-bedroom, two-bathroom vacation rental nestled in the heart of Waikoloa Village. This thoughtfully designed property comfortably sleeps up to four guests, making it perfect for family getaways or a group of...
Walua Trail Oceanview Hideaway:A/C/W/D/Parking
A small suite to the side of a home. No one above or below you. Separate parking, entrance makes it quiet and private. Guests can access to yard to pick fruit when in season. Nice two person deck that has Ocean views and beautiful sunsets. Split A/C unit recently added....
One-Bedroom Villa with Balcony and Resort View
Nestled in Lahaina, this delightful villa offers a cozy retreat for guests. With 1 charming bedroom featuring a king bed and a lovely living room with a sofa bed, this marvelous property is perfect for a relaxing getaway. Enjoy the convenience of WiFi, a washing...
Bay Villas Gold Ocean View 1 Bedroom at The Kapalua Villas Maui, Kitchen
Nestled in lush gardens and beside pristine beaches, our secluded sanctuaries offer tranquility. Enjoy world-class golf, snorkeling, award-winning spa treatments, and farm-to-table dining. Experience luxury in our fully-equipped villas, with stunning sunsets from your...
1 Mi to Magic Sands: Waterfront Big Island Condo
Resort-Style Pool & BBQ Area | 3 Mi to Shopping Area | Covered Parking Space AvailableYour next dreamy island getaway awaits at this oceanfront vacation rental in Kailua-Kona, Hawaii! Start each day with coffee on the private balcony as you admire unbeatable views....
Ocean View Sky Ala Moana Condo w/Amazing Amenities Near Restaurants & Shops
This property requires a minimum 30-day rental. Book with confidence—professionally managed by Ali'i Beach Rentals, an award-winning property management company.Welcome to The Sky Ala Moana, the newest pinnacle of luxury in Honolulu. This exquisite property, consisting...
Right On The Beach & Just Steps to the Sand! A/C
Stunning Condo, Steps Away from One of Hawaii's Greatest Beaches!Come to Maui and watch the stress melt away!Our condo is Just Steps To The Water's Edge! , You can't get any closer to the ocean than our condo! Maalaea village is a gem with its central location and its...
2-bedroom/bath condo in gorgeous Kapalua Golf Villa-Discounted rates for Summer
Thank you for looking at our home for your vacation. We've lowered our rates for a seasonal special!Due to the current conditions, we have also implemented a 24 hour gap between rentals, to allow for our cleaning team to sanitize and clean our home between guests. Enjoy...
Westin Kaanapali North OCEAN FRONT Studio, 7 nights Maui May 8-15, 2026
Ocean Front Villa 7 Nights in Premium Ocean Front Studio villa. Direct view of sand and sea. Steps away from beautiful beach. May 8--May 15, 2026 . Spectacular view of ocean and neighboring islands from balcony. Beach perfect for swimming, snorkling, and SCUBA diving....
One of a small number of Princeville condos directly facing key amenities: pristine pool, hot tub, and grills! Plus 100' from the gym! Sip drinks on your lanai while you watch the family go for a dip. Or use our full stock of beach gear to enjoy Hanalei, Anini, or...
2 Rooms w/ Balcony | Onsite Pool | Free Breakfast
Unwind in a spacious suite with private lanai, deep soaking tub, free WiFi, and plush bedding. Enjoy continental breakfast with Kona coffee, then stroll to Waikiki Beach or nearby shops. After exploring, relax by koi ponds or dip in the pool. Perfect for couples,...
Spacious Ocean View condo with AC in Mauna Kea Resort
Welcome to Waiʻulaʻula A201 — a truly exceptional island retreat.Perched in what is widely considered the best location within the Waiʻulaʻula community, this front-row ridge residence offers sweeping, unobstructed views of the Pacific Ocean, rugged Kohala coastline,...
Furnished monthly rental Waikiki Neighborhood 102
Work-Friendly Waikiki Studio 102 Aloha Waikiki 96815.Monthly Rental - 30+Night Minimum Required bookingBook this home away from home on the serene outskirts of Waikiki!This private full apt offers a retreat for traveling workers or anyone seeking long-term...
Kona Makai 5-101: Ground Floor,1 bedr/2 bathr with Huge Lanai & Ocean Views!
NEW to the Vacation Rental Market | Kona Makai 5-101 as of January 2026!Ground Floor Corner Retreat , Massive Wraparound Lanai ,Incredible Ocean ViewsWelcome to Kona Makai 5-101, a brand-new offering to the vacation rental market—and one that truly makes a first...
Stunning Diamond Head & Ocean Views, Park Free
Summary:The space📍 Prime location. 🏖️ Steps from the beach. ✨ Book now for paradise!Welcome to our Le'ahi Suite, a chic unit located in Waikiki Banyan, carefully designed with our guests in mind to ensure a relaxing and enjoyable stay. Located on the 31st floor, the...
Oceanfront Complex - 2bdrm/2bath with Loft - NEW! Sleeps up to 8! AC, Wifi, more
A piece of Hawaiian heaven! This newly remodeled and refurbished 3rd floor condo is like brand-new. It's a super spacious, high-ceiling, air-conditioned, end-unit, so you have a wrap around lanai with peek-a-boo view of the ocean and a view of neighboring golf course!...
Studio, Sleeps 4, A/C, Kitchen, Beach 5m Drive
The perfect North Shore getaway where everything is brand new. New kitchen and refrigerator. New Air conditioning. New queen Casper mattress, with easy pullout couch that turns into a queen bed. Space sleeps 4 comfortably. Brand new shower with rainfall shower head....