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.
Christmas Week Dec 19-26th at The Westin Nanea ocean resort on Kaanapali beach
Special week December 19th - 26th!!!!!Experience Nanea - a state of relaxation and repose - firsthand. Resort blends a top-notch vacation experience with the authentic history and culture of Hawaii. Amenities include a 10,000 square foot lagoon style pool with a upper...
Relaxing upcountry retreat on the slopes of Haleakalā. Ideal for families.
After a hot day at the beach, relax at Ke Kīhāpai Bed & Breakfast at the 2400 foot elevation with unobstructed views of our dormant volcano, Haleakalā. Breathe the fresh air with an upcountry view of town, the north shore of Maui and Kahālāwai (West Maui...
Golf Villas Ocean View 1 Bedroom at The Kapalua Villas Maui, Full 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...
Escape to Paradise! 2 Serene Units, Pool, 3 Restaurants, Right on Beach!
Looking for a beachfront getaway in Waikiki? Look no further than this convenient property! Just minutes from the most popular attractions, the excitement of Waikiki is all around you! And with comfortable amenities and authentic Hawaiian hospitality, you'll have...
Lahaina Shores 421 - Studio Oceanfront Condo
* NEW PROMO: Stay 5 or more nights from September 1st - October 31, get 1 FREE!NEW LISTING: Lahaina Shores 421 - Many upgrades!Lahaina Shores is a charming boutique resort located directly on the ocean with a beautiful view of the neighboring island of Lanai. Unit 421...
The Westin Kāanapali Ocean Resort/ 2-Bedroom
Summary:Explore the summit of a dormant volcano. Or hike through a rainforest to a 400-foot waterfall. There’s no better place than Maui for a once-in-a-lifetime experience. The Westin Kā‘anapali Ocean Resort Villas maintains relationships with the top tour...
Wyndham Royal Sea Cliff | 2BR/2BA King Balc Suite
Summary:Nearby Pu‘uhonua o Hōnaunau, an ancient sanctuary whose name means "the place of refuge," could easily describe this resort. Oceanfront, modern, and conveniently tucked outside Kailua-Kona, tranquility reigns. It’s the ideal home-base for all of your island...
Kaia Villa, at Turtle Bay - North Shore Oahu Retreat
Be among the very first to experience Kaia Villa, a newly renovated boutique retreat debuting October 2025. Located at Turtle Bay on Oʻahu’s legendary North Shore, this private villa is being completely transformed into a modern organic retreat designed for luxury,...
Aston at the Whaler on Kaanapali Beach #623
The expansive floor plan creates a very spacious two-bedroom, two-bath condo. This well-appointed condo has been completely remodeled with top-of-the-line finishes and furnishings. The lanai wraps around from the mountainside to the center courtyard and offers sweeping...
Diamond Head Grandeur: Kahala Luxury Villa with Ocean View
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.Find peace and tranquility in your very own...
Pool House with 2Queen Beds – Poolside Comfort
Enjoy a relaxing poolside retreat in this 484 sq. ft. studio featuring two queen beds and a wet bar. With air conditioning, free Wi-Fi, and modern comforts, this studio provides a perfect blend of convenience and luxury for your stay.Key Features: • Design-Centric...
Royal Sea Cliff Kona Garden View 2 Bedroom
Garden View 2 Bedroom 2 Bath- Condos located on 1st, 4th and 5th floors- Private balcony- Kitchen features stovetop, oven, refrigerator, microwave, dishwasher, coffeemaker, blender, cookware and tableware- Master bedroom with 1 king bed and private bathroom with...
The Heights Hideaway
About this spaceCute & cozy two-bedroom apartment on the ground level of a single-family home. Private entrance. Includes a full kitchen with appliances and a private bathroom with a shower.The spaceYour space is located on the ground level with a private entrance.You...
Kailua Beachside: Lux Beachfront Villa w/ Heated Pool, Ocean Views & Modern Amen
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.Stay at Kailua Beachside by Gather, a...
Newley remodeled and beautifully furnished downtown Kailua-Kona condo.
Located on the ground floor at Kona Plaza Condominiums, Unit 107 is newly remodeled & just steps away from downtown Kailua Historic Village & the Kailua Pier. Decorated with a taste of Hawaii that will set the mood to kick start your Hawaiian adventures. Fully furnished...
Island Surf 510 | Water Views, Across from the Beach + In the Heart of Kihei!
Escape to the serene paradise of Island Surf 510C, a cozy tropical condo nestled in the heart of Kihei, Hawaii. This charming vacation rental offers a tranquil retreat for up to 4 guests, boasting 2 spacious bedrooms and 2 bathrooms all conveniently situated on one...
New Listing! Tropical Oceanfront getaway awaits
Welcome to Paki Maui 412 – Your Perfect Maui Vacation Rental! Escape to paradise at Paki Maui 412, a beautiful 1-bedroom, 1-bathroom condo ideally located in the heart of Honokowai, Maui. Perfect for families, couples, or small groups, this unit comfortably...
Fantastic Location - Beautiful Beach Front Condo -Makena Surf # B-207
Makena Surf B-208Welcome to Makena Surf B-208, a luxurious oceanfront condo that combines the serenity of beachfront living with upscale finishes and exceptional comfort. Located in the prestigious Makena Surf Resort, this second-floor unit boasts panoramic views of the...
Konishiki Beachhouse: Luxury 4BR Oceanfront Home w/ Private Pool, Beach Access
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 Konishiki Beachhouse 4BD by Gather,...
Kapalua Golf Villas Ocean View 2 Bedroom
Golf Villas Ocean View 2 Bedroom 2 Bath- Situated along Kapalua’s Bay Course fairway- Fully equipped kitchen includes stovetop/oven, microwave, refrigerator, coffeemaker, cookware, tableware- Master bedroom with 1 king bed and bathroom- Guest bedroom with 2 twin beds;...
Butterfly House: Beautiful Ali'i Drive Home with Ocean Views!
Incredible Modern Alii Drive Home with Ocean Views! A beautifully renovated home right across Kahalu'u Beach on the historic Ali’i Drive.Modern finishes throughout. 2 Master bedrooms with 2 full baths. Modern fixtures in all areas of the home.Stay cool with ceiling...
2/2 Modern & Elegant Penthouse Oceanfront Vistas
Summary:Spacious and elegant. Completely remodeled in December 2022, 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...
Puna Rainforest Retreat Hotspring - Purple Passion Cottage
The Purple Passion Cottage is located on a serene 20 acre estate with beautiful ocean and meadow views. The cottage is cozy and equipped kitchenette (range, oven, mini-fridge/freezer, microwave), full bathroom and two bedrooms. The main bedroom has a king bed with an...
Princeville Kauai 2 bedroom 2 Bath Sleeps 5
Please Send An Inquiry Before Requesting To Book By Clicking The Contact Host Tab.This premier complex, perched on a verdant bluff, provides a paved path to Hideaways Beach, where you can snorkel, swim and soak up the sun. On-site amenities include a restaurant,...
Lahaina Shores Oceanfront Corner Location ~ Unit 601
* NEW PROMO: Stay 5 or more nights from September 1st - October 31, get 1 FREE! Lahaina Shores 601 – Oceanfront Elegance with Panoramic ViewsDiscover the magic of Maui from Lahaina Shores, a charming boutique resort set directly on the ocean in the heart of Lahaina....
Beautiful Apartment in Hawaii
Newly refurbished apartment, attached to our family house. Separate entrance. The apartment is located in the historic and very authentic neighborhood of Captain Cook, 2 minutes drive to the beginning of the famous Captain Cook monument trail, and 15 minutes drive to...
Dlx 1 br Waikiki Condo Rental...Sleeps 5/Lovely views. Waikiki Beach!
Enjoy your own 1-BR Oahu condo rental - just a short stroll to Famous Waikiki Beach & and ideally located near world-famous Diamond Head. On the 'quiet side' of Waikiki. Your 1-bedoom Waikiki Beach Condo vacation getaway is appointed in a cool Hawaiian-tropical decor,...
Maui Resort Rentals: Honua Kai Konea 504 – Luxurious 2BR w/ Beautiful Partial Ocean & Mountain Views!
Konea 504 is a luxurious two-bedroom suite, offering guests the best of both worlds, beautiful partial ocean and mountain views right from the comfort of your spacious private lanai. Located in the very first two-bedroom stack from the oceanfront column, your group will...
Hawaiian Oasis w/ Private Pool, 2 King Suites & Sunset Views!
Discover true Aloha at this stunning private 3-bedroom oasis, where island charm meets luxury. Behind a gated front entry, this beautifully designed home features soaring vaulted ceilings, dramatic lava rock wall & 2 king suites and a chefs kitchen, offering a serene...
Maui Resort Rentals: Honua Kai - 3 Total Bedrooms, Premier 5th Floor Interior Courtyard Offering w/ Stunning Ocean Views!
This tandem 3BR/3BA pairing is comprised of two fantastic 5th-floor oceanview suites located directly next door to each other. Both suites overlook the lush resort grounds and pools of the Hokulani Tower interior courtyard and provide stunning full ocean views.Gather,...
Relaxation Bungalow with Hot tub, Sauna, Lush Garden, and Pristine Island Living
Escape to Hale Kalani, a charming 3-bedroom surf bungalow nestled in the heart of Princeville on Kauai’s renowned North Shore. Thoughtfully designed for relaxation and island living, this single-level haven features a private cedar barrel sauna, a brand-new hot tub,...
Marriott Maui ocean club full kitchen, washer dryer on beautiful Kaanapali Beach
February 22/26 thru 3/1/26 only Escape to this fabulous condo in picturesque Lahaina. This wonderful property features 2 gorgeous bedrooms with king beds, 2 bathrooms with luxurious amenities like a full kitchen, jetted bathtub, and a cozy living room with a sofa bed...
Waikiki Shore Park View 1 Bedroom
Park views and beachfront living come together in this cozy one-bedroom condo, located in the only condo building on Waikiki Beach. Featuring a private bedroom, full bath, and all the essentials, it's the perfect island escape for couples or small families.• Waikiki...
*Hono Kai A14* New Listing! Maui condo steps to the sand!
Beautiful ground floor and newly remodeled! Hono Kai A14 is a garden-view unit, immersed in rich tropical foliage with a spacious private lanai only steps from the complex beach access! Decorated with a modern beachy decor, this unit features a master suite with a comfy...
1 Bedroom Partial Ocean View Condo - Kaanapali Shores 830
Settle into your Hawaiian vacation in this Oceanfront and ground-floor condo with beach and pool access in Kaanapali. Wake up to the ocean breeze and just steps away from one of the most popular beaches in Maui. Recent upgrades include: The kitchen has all-new stainless...
"Windjammer" Studio w/FREE parking & Full Kitchen
Our Premium WINDJAMMER STUDIO is spacious, recently renovated, fully furnished and centrally located just steps away from famous Waikiki Beach where you can enjoy the sand and surf. We include FREE PARKING, full kitchen, free Wi-Fi and a private lanai. We provide 100%...
Airy Coastal Dream Vistas
Summary:Completely remodeled 1 br, 1 bath modern condo with upscale Hawaiian style. Located directly across from the beach in warm & sunny Kihei. Nestled in the lovely and desirable Kihei BayResort, you will be embraced in the tranquil grounds and ocean views. We...
RELAX w/ Direct Beach Access High Flr. Sans Souci 2BD/2BA🌴Stunning Ocean Views
Nestled along the southeastern coast of Oahu, Hawaii, welcome to Sans Souci condominium 901/902, on the only beach in the heart of Diamond Head along the Gold Coast adjacent to Waikiki. The first thing you will notice is the incredible ocean view from this luxurious...
Tropical Comfort & Poolside Peace—2 Room Island Haven Awaits
Endless adventure awaits in Kailua-Kona! Whether you're staying for a day or a week, our hotel puts you close to top attractions, local dining, and must-see spots like the Amy B.H. Greenwell Ethnobotanical Garden and Pu'uhonua o Hōnaunau National Historical Park....
A11y Room with 2 Double Beds, Lanai and City Views
Designed with accessibility in mind, this 242 sq. ft. room features two double beds and a private lanai with city views. With accessible features, air conditioning, free Wi-Fi, and modern amenities, this room ensures a comfortable and convenient stay for all guests.Key...
Stunning Ocean Views and direct beach access in this Hawaiian Oasis
One of the more desirable units on the ground floor with direct access to the grassy area and the beach. This oceanfront two-bedroom, two-bath unit in the Kai Lani community of Ko Olina offers a truly unique and desirable lifestyle, blending natural beauty, luxurious...
Alii Villas#318 Beautiful Top Floor Condo with Garden & Ocean Views
Top-Floor Ocean Escape – Remodeled Beauty at Alii Villas #318Welcome to your slice of paradise on the top floor of the highly sought-after Alii Villas in stunning Kailua-Kona, Hawaii! Unit 318 is a fully remodeled, beautifully furnished condo that blends island charm...
STUNNING 1st Floor 🌴 Beachfront 2BD Sans Souci w/Parking 🐬
You'll find bicycles, golfing, and more on site at this beach condo. Waikiki Beach and Kaimana Beach are just a short walk away, so leave your car at the property, which offers covered onsite parking. After you return to this 1473-sq-ft condo, unwind on the deck or...
Honolulu Paradise Condo
Centrally located condo, steps to all your destinations while you visit Hawaii. 2 bedroom's and 2 bathrooms plenty of space to enjoy, relax, and adsorb paradise. Open full kitchen overlooking the balcony with mountain and water views best of both worlds. Completely...
Beach Inspired Family Suite w/ Kitchen, Washer/Dryer, Lanai–Waikīkī Shore 510
Welcome to your home-away in this fifth-floor, one-bedroom one-bathroom, ocean view unit. Upon entry, you will be greeted with a white back-drop that has been enhanced with many shades of blue throughout the space. Welcome to the 'beach house!'Guests can embrace the...
Large 2 Bed 2 Bath in Gorgeous Maui Kamaole Complex South Maui
Perfectly perched on the second floor, our vacation rental offers a serene retreat elevated above the ordinary. Upon arrival, conveniently park your vehicle in the space directly in front of the property. A welcoming staircase leads you to the entrance of the condo,...
Lanikai Oceanfront Home with Pool and Japanese-Style Hot Tub
Six bedroom ocean front home with pool and Japanese-style onsen (hot tub) is ideally suited for multi-family or multi-generational accommodation. Recent renovations and 2021 upgrades include split-air conditioning throughout the home, updated landscaping, new...
Urban Chic Meets Island Serenity in Waikiki
At the beginning of Waikiki, the tourist center of Honolulu. Our charming studio in Waikiki is a breezy unit in Hawaiian Monarch building.Enjoy breathtaking Mountain & Canal views. Hotel quality sheets, pillows, and air conditioning await you.Excellent location right...
OCEAN FRONT 9th Floor Corner unit nWatch the Whales jumping from the Balcony
In the heart of Maui's famous Kaanapali Beach, steps away from Whaler's Village, with beautiful shopping and restaurants. Beautifully remolded and decorated one bedroom with 2 FULL baths, sleeper sofa and roll-away bed. Wrap around balconies and magnificent views....