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.
Maui Resort Rentals: Honua Kai – 8BR Groundfloor Residence, Over 5300 Combined Sq. Ft., Massive Lawn Areas, Steps to Pools/Beach/B.B.Q.s!
This package combines 4 neighboring ground floor residences at the luxurious Honua Kai Resort to create an 8 bedroom masterpiece that can accommodate up to 24 guests! Large families and groups are treated to the space of a luxury home with all the advantages of resort...
Royal Kahana Maui 1006 Ocean View 1 Bedroom
- 10th floor condo with balcony- Tile & Vinyl plank flooring throughout- Fully equipped kitchen with– fridge, stove/oven, microwave, cookware, tableware- Tiled bathroom with walk-in tiled shower with grab bar- Bedroom with 1 king bed- 777 sqft- Maximum 4 persons...
Oceanfront 2BR Villa at Westin Nanea – Maui Luxury by the Sea
Step into tropical elegance with this two-bedroom, two-bathroom oceanfront villa at Westin Nanea Ocean Villas, perched on 16 acres along Ka‘anapali’s North Beach. With approximately 1,260 sq ft of interior space, this villa comfortably accommodates up to six adults,...
Ocean View 1BR Premium Villa at Westin Kāʻanapali North
Wake up to the beauty of Maui’s coast in this 1-Bedroom Premium Ocean View Villa at The Westin Kāʻanapali Ocean Resort Villas North. Offering 750–900 square feet, this spacious villa is ideal for couples or small families seeking a blend of comfort and luxury with...
NEWLY redecorated unit! STYLISH Waikoloa getaway! ~7 min to Hilton
NEW! Entire UNIT! Stylish island decorRelax in a freshly styled Waikoloa retreat with island-inspired mural art by award winning local artist, HUGE wrap-around lanai with peek-a-boo-OCEAN views & SUNSET along with Kohala coast overlooking the golf course.Walk to Hilton...
New Listing: Lahaina Shores Studio Available Now
Lahaina Shores 504 – West Maui Mountain ViewsLahaina Shores is a charming boutique resort located directly on the oceanfront in the heart of historic Lahaina Town. Unit 504 is a 5th-floor West Maui Mountain view studio offering privacy, comfort, and can accommodate 2...
Stunning Ocean-View Retreat Overlooking Laupahoehoe Point
Welcome to your tropical escape! This stunning three-level home boasts panoramic ocean views and a tranquil setting, making it ideal for a peaceful and rejuvenating vacation.With 1,500 square feet of space, the main living areas are located on the upper level, while the...
Gated Tropical Hawaiian retreat, 5 minutes to Kailua Kona town and the Ocean.
The Kona Palm Retreat is a private gated estate located 8 minutes from kailua Kona town and the Pacific Ocean. This property is newly listed on VRBO, this property is a guest favorite and has over 200 5 star reviews on another popular listing site., The Kona Palm...
Partial Ocean View Two Doubles, 3 Units, The Twin Fin Hotel
Every vacation is enjoyable and restful, thanks to the contemporary atmosphere and convenient amenities of our hotel. Spend the day at the outdoor pool with a large sun deck and lounge chairs or catch some rays at the neighboring beach. You may also try delectable meals...
New Listing: Beachfront Studio in West Maui
Lahaina Shores 520 – Studio in West MauiLahaina Shores is a charming boutique resort located directly on the oceanfront in the heart of historic Lahaina Town. Unit 520 is a 5th-floor West Maui Mountain view studio offering a comfortable stay for 2 guests. At Lahaina...
Kanaapali Maui- Newly Renovated Peaceful Ocean View 2B/2B Condo
Relax with the whole family at this peaceful Maui condo located in the heart of Kaanapali across the street from one of Maui’s most beautiful beaches. This newly renovated one level condo on the ground floor has epic views of the ocean, the island of Lanai and...
Luxurious 1-bedroom villa at WESTIN Nanea Oceanfront Resort!
Make the most of Maui by treating yourself to an elegant, lavishly appointed one-bedroom villa at the exclusive WESTIN Nanea 16-acre deluxe resort. Upon arrival, guests will check-in at the resort’s front desk using their resort confirmation # just as if they had...
Beautiful and timeless Kona Coast Resort - 1BR/1BA
When you stay at Wyndham Kona Coast Resort in Kailua-Kona on the Big Island's west coast, you will feel as if you are stepping back in time to a more simple, unspoiled era. Every detail has been designed to re-create the charming traditional Hawaiian island ambiance...
Sunset Point Hawaiian Beachfront: Exclusive Beach Home w/Hot Tub/Surf Break Spot
Welcome to Sunset Point Hawaiian Beachfront by Gather, a captivating three-bedroom, one-and-a-half-bathroom Hawaiian home, perfectly situated on the pristine Sunset Beach in the picturesque North Shore of Oahu. This residence, known as one of the area’s finest,...
Kahana Outrigger #4A2 - Vacation West Maui
Maui Paradise: Family Beachfront EscapeNestled on the sunny west coast of Maui, this private haven awaits you in Kahana, between the famed Kaanapali and Kapalua resorts. This property offers a unique escape that the whole family can enjoy, mere steps from the...
Resort living in Ko Olina's Coconut Plantation!
Enjoy resort living in Ko Olina's Coconut Plantation! This fully furnished 2-bedroom has an additional bonus room with 2 single beds, to sleep up to 6. The lanai overlooks the private hot tub, the perfect space for relaxation. 1 car garage + 1 assigned open parking...
kaanapali-alii-unit-144
Welcome to Kaanapali Alii Unit 144, a luxury vacation rental that promises an unforgettable stay on Maui. This elegantly renovated condominium is designed for comfort and sophistication, offering breathtaking views of the Pacific Ocean and the beautifully landscaped...
Seahorse Beach House: Calm Oasis w/ Private Yard Just Steps from Kailua Beach
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.Seahorse Beach House is a hidden Hawaiian gem,...
Maui Kamaole H-208 – Oceanview Poolside Condo Close to Beaches and Dining
Maui Kamaole #H-208 – Partial Ocean View Comfort in South KiheiExperience the beauty of Maui from Maui Kamaole #H-208, a spacious two-bedroom, two-bathroom condo offering partial ocean views and a comfortable layout. Perfect for families or friends traveling together,...
Maui Resort Rentals: Honua Kai – 7 Total Bedrooms, Stunning Ocean Views, 4,465 Combined Sq Ft, Sleeps up to 22!
Perfectly suited to larger groups or families, this 7 bedroom gem combines one of our most sought after 3BR oceanfront "Ali'i" residences with a stunning neighboring 2BR oceanview suite, and a spacious 2BR partial Oceanview located directly across the hall. The generous...
The Bluffs at Mauna Kea Villa 5 Five Bedroom
Set in a gated community, this oceanfront estate has been crafted by Hawaii’s best architects and interior designers and is a true masterpiece. This residence offers a great room with sliding glass pocket doors for indoor/outdoor island living, a chefs' kitchen with...
Maui Banyan T203 Spacious Island Getaway Close to Kamaole Beaches
Welcome to your serene Maui getaway at Maui Banyan T203, a beautifully designed retreat offering the perfect blend of comfort and island style. Located in the heart of Kihei, this condo sleeps up to six guests and provides everything you need for a relaxing Maui...
Feel Royal in a Royal Garden studio suite, Waikiki
Located along the Ala Wai canal, the resort boasts European-style gardens blended with the tropical appeal of Oahu. The outdoor pool, garden, media lounge, and sauna bring tranquility, while bustling Honolulu adventures abound beyond the grounds. Come find your piece of...
HGVC Point At Poipu 2 Bed 2 Bath Unit
PLEASE DO NOT RELY ON CALENDAR FOR AVAILABILITY! THIS IS A TIMESHARE RESORT AND THEREFORE DATES COME AND GO EVERY DAY. PLEASE USE "ASK OWNER A QUESTION" BUTTON FIRST TO INQUIRE ABOUT AVAILABILITY. DO NOT SEND A BOOKING REQUEST BEFORE CONFIRMING YOUR DESIRED DATES ARE...
KBM Resorts | FREE CAR | Honua Kai Hokulani | Mountain view | 1-Bedroom Condo, Breathtaking views! HKH-524
** 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...
Luxury Oceanfront Living at the Sands of Kahana
This listing is a combination of 2 separate units close to one another.Each unit can accommodate 4 adults and 2 kids. Total of 8 adults and 4 kids. DescriptionWelcome to a rare opportunity to experience the best of oceanfront living at the Sands of Kahana. This listing...
Lodge at Kukui'ula Villa 4
This stunning villa provides barefoot elegance and comfortable accommodations for up to eight guests across four bedrooms. Three bedrooms are found in the primary home, with a fourth bedroom located in the detached 'ohana, providing a private oasis for guests who choose...
Paradise Awaits: Luxurious Oceanfront Hawaiian Escape - Sleeps 4
Welcome to your tropical paradise! Nestled on 26 acres of lush, oceanfront property, this 1-bedroom unit at Westin Kaanapali Ocean Resort Villas offers stunning views of the Pacific and the neighboring islands of Lana'i and Moloka'i. Ideal for couples or small families,...
Wailea Beach Villas PH205 - 3 Bedroom Garden View Penthouse
Welcome to Wailea Beach Villas Penthouse 205, an elegant retreat that showcases sophisticated furnishings, vibrant colors, and striking artwork. This family-friendly penthouse features three bedrooms and three full baths, offering ample space for families or groups to...
Hawaiian Luxury Villa – Tranquil Elegance at Mauna Kea Resort
Summary:Experience the pinnacle of Hawaiian luxury in this stunning 3-bedroom, 3.5-bath retreat, nestled within the prestigious gated community of Kauna'oa at Mauna Kea Resort. Just a short walk to the beach, this exquisite pod-style home offers seamless indoor-outdoor...
Keauhou Punahele D-102 Ground Floor, Gorgeous Remodel, Incredibly Spacious
Keauhou Punahele D-102 – Remodeled Ground Floor Retreat in Kona’s Premier Coastal CommunityWelcome to Keauhou Punahele D-102, your perfect Hawaiian getaway nestled in the heart of Kailua Kona. This beautifully remodeled ground floor condo offers modern island living...
Cool cottage with AC in Keaau
Escape to a delightful 2-bedroom cottage in Keaau. This lovely retreat features 1 queen bed, 1 sofa bed, and a cozy office space with a crib. Guests can relax in the charming living area or unwind in the modern bathroom with a shower. With amenities like AC, heating,...
Westside Magic 3bed 2 bath house in terrific westside of oahu!
Experience the paradise of Hawaii’s West Side! Just half a block from the beach, this home offers stunning ocean views. Relax on the lanai and take in the beautiful shades of blue, turquoise, and green that only Hawaii’s waters can provide. Dolphins can be spotted...
Dlx 1BR Beachfront Maui Condo..Kihei/South Shore. AC.nStunning Ocean Views!
Aloha: Welcome to your own 1Br oceanfront Maui condo rental, ideally located on the sunny South Shore/Kihei...just steps to the sand! Enjoy stunning ocean views from your own private lanai/balcony, while listening to the sound of the surf! Appointed in a hawaiian-...
Modern Studio in the Center of Waikiki!
Enjoy a stylish experience at this centrally-located place in the center of Waikiki! Two blocks to Waikiki Beach to enjoy unforgettable sunsets, rejuvenating Pacific Ocean swimming, and mind-numbing ocean gazing. Steps to world class or budget friendly dining. You can...
Palms at Wailea Villa 301 Garden Deluxe 1 BD 2 BA
Relax in this one-bedroom villa with tranquil garden views in the heart of Wailea’s resort community. Designed for comfort and convenience, it features a full kitchen, airy living space, and easy access to beaches, golf courses, and walking paths. Villa 301 Garden 1...
7th Fl Ilikai | AC | Pool
The SpaceExperience Waikīkī charm with a touch of island aloha in this beautifully decorated Ilikai suite. From your private balcony, enjoy sweeping lagoon and ocean views while sipping morning coffee and watching surfers at Kaiser Bowls.Condo Features• Queen bed...
Aqua Aloha Surf Waikiki 506 Deluxe Studio with Lanai and Partial City Views
Aqua Aloha Surf Waikiki 506 Deluxe Studio with Lanai and Partial City Views located just 2 Blocks to Waikiki Beach, (1) Full/double bed, (1) Twin bed + (1) Queen Futon, Sleeps 4, 361 Sq FtAqua Aloha Surf Waikiki offers a range of accommodations that are perfect for...
2 Bedroom Villa at the Westin Nanea Ka'anapali
Located on 16 acres of Maui's famous North Kā'anapali Beach, The Westin Nanea Ocean Ocean Villas puts you at the center Maui’s fun filled local activities and events as well a variety of world-class amenities right outside your villa door.
Islands at Mauna Lani N3
Design and style inspired by the Far East blend nicely with tropical Hawaiian touches in the Islands at Mauna Lani N3. From the moment you walk into this two-bedroom two and a half bathroom vacation rental you will be wowed with the wood flooring, white-on-white living...
Kapalua Ridge Villa 212, spacious with ocean views.
Escape to paradise at Kapalua Ridge Villa 212, where Ocean views, spacious interiors, and refined island touches come together to create the perfect Maui getaway. Located within the prestigious Kapalua Resort community, this 2-bedroom, 3-bath villa comfortably...
Best View in Honolulu
HUGE 1,400 square foot property - 2 spacious bedrooms, 2 bathrooms, living room, dining area, kitchen, washer/dryer, central air conditioning, 300 sq. ft. lanai (the size of a NYC apartment!), one of the most spectacular and expansive views in all of Hawaii - Diamond...
LS 512 Getaway Studio by the Beach Pool Hot Tub
Lahaina Shores 512 Relax in this Remodeled Studio at the Beach with Majestic West Maui Mountain Views! FREE daily activities included with your stay value up to $570! Complimentary admission, every day of your stay*: Whale Watch (seasonal), Dinner Sunset Sail, Snorkel...
Kamaole Sands - Deep Lanai with Inner Courtyard and Ocean Views!
Discover paradise in this stunning condo at Kamaole Sands, Building 10, with some of the best ocean, fountain, and garden views in the complex. Relax on the spacious private lanai with a tropical ceiling fan, perfect for savoring Maui's breathtaking sunsets.The modern...
Kaanapali Maui Eldorado J204 Garden View 1 BD
Tucked away on peaceful Kaanapali golf course, this one-bedroom condo features lush garden views and easy beach access. With a comfortable bed and well-equipped kitchen, it offers a relaxing stay for couples or small families looking to enjoy island life. Unit J204...
Escape to Family Fun and Island Bliss at WorldMark Kihei- 1 Bedroom
If you're looking for the ultimate Hawaiian escape packed with adventure, relaxation, and family fun, look no further than WorldMark Kihei on the stunning island of Maui! Nestled just steps away from the beautiful beaches of South Maui, this resort offers the perfect...
Kaanapali Maui Eldorado Partial Ocean 1 Bedroom
Take in partial ocean views from this one-bedroom Maui retreat set on Kaanapali golf course. Just a short walk from the beach, it offers a full kitchen, comfortable living space, and a private lanai—perfect for soaking in the breeze after a day of exploring. Partial...
Blissful 1 Bedroom w/lanai, WiFi, and Cable-#H206
Families love the homey touches of this one-bed/two-bath air-conditioned suite located across from popular Kamaole II Beach Park. The open kitchen features a breakfast bar, refrigerator, dishwasher, stovetop, oven, microwave and coffeemaker. Also enjoy a washer/dryer,...
Sheraton Kaua‘i Resort Villas | Two-Bedroom Villa
Summary:Sheraton Kauai Resort Villas is located on the beautiful garden island of Kauai. This resort welcomes you with all the comforts of home for a relaxing vacation. Spend your days enjoying the beauty of nature with hikes, boat tours, whale watching, beaches, parks,...
Tradewinds Plaza Waikiki Oceanview Private Rental Sleeps 4
Escape to The Tradewinds Plaza in Waikiki TP606 - Your Ideal Vacation RetreatProperty Details:Address: 2572 Lemon Road #606, Honolulu, HI 96815Property Type: 30-day Minimum 1-Bedroom Vacation RentalEscape to The Tradewinds Plaza in Waikiki Suite 606 offers a spacious...