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.
Kapalua Golf Villa 16P7 Fairway View 2 Bedroom
Golf Villa Unit 16P7 Fairway View 2 Bedroom 2 Bath- 1st floor villa overlooking Kapalua Bay Golf Course’s 6th fairway- 19 stairs between parking and front door- Two interior stairs between front door and living room/kitchen/second bedroom- Tile entry, kitchen and...
Tropical Paradise Awaits at Maui Kamaole L107. Across from 2 Fave Beaches!
* Coastal Living! Updated in 2024! * 1 Bedroom/ 2 Baths-Sleeps 4* Across from 2 Popular Beaches* Ground Floor and Near the PoolExperience the perfect blend of luxury and convenience at Maui Kamaole L107. This newly updated ground floor condo boasts fresh paint, stylish...
New Listing! Bedroom with private lanai access
Welcome to Nohonani 103, your newly refurbished oceanfront escape in West Maui! This inviting ground-floor, 1-bedroom, 1-bath condo offers all the comforts of home with unbeatable access to the beach—just steps from your private lanai. With space to accommodate up to...
Maui Banyan H-308 1 Br Ocean View Condo, Walk to Kamaole Beach Park II
Bright and open Ocean View Condo. This unit has one bedroom with a queen bed and a pull-out sofa bed in the living room, allowing this unit to sleep up to four people. The Kitchen opens up to the dining and living areas, creating a wide-open living space. The bedroom...
Lahaina Shores Luxury Oceanfront Ocean View & Mountain View w/ 2 Lanais
Lahaina Shores Oceanfront Luxury with Stunning Dual Pacific Ocean Views and Majestic Maui Mountain Views & Two Expansive Lanais Studio CondoWake Up to Paradise Every Day!Experience the ultimate Hawaiian getaway at our spectacular luxury oceanfront retreat, where endless...
3-bedroom Diamond Head Floor-Through Apartment On Ocean - Minimum 3 months
3 month Min: The ultimate diamond head apartment. 2000 square feet on ocean. Newly renovated. Surf in front @ Tonggs. Walk/Run around Diamond Head. Right off Kapiolani Park. The ultimate super chill; elegant; breezy and easy place to hang/enjoy/live.
Wailea Beach Villas PH106
Welcome to Wailea Beach Villas Penthouse 106, a luxurious ground-floor retreat in one of Maui’s most prestigious beachfront communities. This stunning 1,899-square-foot villa offers the perfect blend of island elegance and modern comfort, making it an exceptional...
Ocean View King | Kaimana Beach Hotel | Scenic Stay by the Beach
Kaimana Beach Hotel is a beachfront haven just minutes from Waikiki’s shopping, dining, and surf. The Ocean View King offers a spacious layout and sweeping Pacific vistas. Enjoy the best of beach life from the comfort of your room.This listing is for a room within a...
Kapalua Ridge Villa 2522 Fairway View 1 Bedroom
- The Ridge Villas are perched high above with views of The Kapalua Bay Course’s Fairway.- Very spacious lanai with views toward mountain, golf course, and ocean. - Second floor unit, two-level townhome, with multiple stairs from parking to the villa. - Tile in...
Wai'ula'ula Villa 348 Three Bedroom
Perched in the uplands of the prestigious Mauna Kea Resort, this stunning villa offers sweeping panoramic views of the Kohala Coast, where breathtaking sunsets paint the sky. Designed for seamless indoor-outdoor living, it features an expansive covered lanai with plush...
Ilikai Hotel Oceanfront, Top Grade Upgrades Throughout! 30-day Rental Only!
If you're seeking a place with stunning views, this condo is perfect for you! Don't miss out on this once-in-a-lifetime experience—book now!Experience the ultimate Waikiki luxury in this one-of-a-kind 3-bedroom, 3-bathroom condo at the iconic oceanfront Ilikai...
Oceanfront 2BR/2BA, 20ft from Shore, 180° Ocean View, Pool
OCEANFRONT, RIGHT ON THE WATER, spacious 2-bed, 2-bath condo on the 2nd floor just south of Kailua-Kona town. With breathtaking 180-degree Kona coastline and ocean views, watch humpback whales, spinner dolphins, yellow tangs and boats from the waterfront lanai as you...
Oceanfront Napili Shores ~AC~Ocean View
Escape to this fantastic condo in picturesque Lahaina. This cozy retreat features 1 bedroom with a comfortable king bed and an additional living space with a queen bed and a twin bed. Guests can enjoy amenities like WiFi, AC, and a hair dryer. With a convenient location...
Romanna’s Golden Ray Oceanfront Condo, Maui Resort
Welcome to your slice of paradise at Maui Sunset, where you can enjoy partial ocean and stunning garden views from the living room and lanai! Experience the convenience of direct access to the pool, BBQs, and sandy beach, all just steps from your lanai. The beautifully...
Large 3/2 House in Kailua-Kona with ALL New Furnishings and Yard Above Airport
Kona Coastview SubdivisionAs you step inside, you'll discover a spacious layout boasting three cozy bedrooms, each brand new furnishing master bedroom with a comfortable queen-sized bed set and ample closet space for all your belongings. Master bathroom with tub/shower....
The Famous Peacock House
The Famous Peacock House – Spacious & Whimsical Big Island RetreatWelcome to The Famous Peacock House, a vibrant and whimsical Hawaiian getaway designed for families and friends to create unforgettable memories together. With space for large groups, thoughtful...
Boutique Hotel Waikiki FREE parking
Excellent Location, free parkingEnjoy a comfortable stay in this independently owned hotel room featuring a king-size bed, along with a twin-size pull-out for a third guest if needed, full bathroom, central AC, and a flat screen TV. The room includes a mini fridge,...
Modern Princeville Retreat – Hanalei Bay Rental with Private Pool
This beautiful brand new home is overlooking Hanalei Bay & the beautiful tree canopy of Princeville. With a 10 min walk to the 1 Hotel beach, a short walk to Princeville Center and a quick drive to Hanalei Town, it is the ideal central north shore location. Featuring...
Step Out into Waikiki: Homely Hotel Perfect for Family Retreat | Outdoor Pool
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,...
Gorgeous Kauna'oa Home - 5BR, 6BA, 10-Minute Walk to Beaches!
Brand new and gorgeous private estate at the only community that is walking distance to the two best beaches on the Big Island, Mauna Kea and Hapuna! This home has a prime location atop a bluff in the luxurious Kauna'oa community. Built with open space and privacy in...
Peaceful 3 Bedroom Home with Fabulous Views
This is a minimum 31 day rental listingPerfect for extended vacation or traveling worker; traveling nurses or doctorsWell appointed, well maintained, privateBeautiful home in desirable, safe neighborhoodClose to beaches, shopping, town, golf, tennis and pickleball, as...
Wyndham Mauna Loa Village | 1BR King Bed Suite
Summary:If sunset cocktails, pools, and plenty of tennis sound like your style, you’ve found your spot. Located in Kailua-Kona next to a country club, this tranquil oasis sits away from town traffic and crowds while offering convenient access to the island’s many...
Stylized Captain's House
This Stylized Captain's House is located minutes away from family friendly scenic Kealakekua Bay beaches, the national park Pu'uhonua O Honaunau, & the island's best snorkeling spot "Two Step".An ideal setting for tropical adventures of all kind, offering spacious...
Scenic Kauai Stay Near Allerton Garden + Free Pool Access + Kitchen
Experience oceanfront serenity with stunning views, spacious rooms, a full kitchen, a private balcony, and in-room laundry—ideal for couples and families. Snorkel nearby, hike the Mahaulepu Trail, or spot turtles at Poipu Beach. Relax in our large outdoor pool....
Hale Makana: Portlock Luxury Home with Pool & Ocean Views
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.Hale Makana is a luxurious, single-level...
Maui Ka’anapali Villas #137: Studio garden view condo at Beach Front Resort on N
Maui Ka’anapali Villas #137: Studio garden view condo at Beach Front Resort on N. Kaanapali Beach.This newly remodeled condominium is located on the ground floor, giving quick and easy access to the pool. This luxurious studio is furnished with a king-sized bed and a...
Modern Beach Apartment North Shore Home
Your Waialua adventure begins at this fantastic 1-bedroom apartment. The space features a queen bed, AC, a washing machine, and WiFi. The bathroom includes a shower and a hair dryer for your convenience. Nestled in a serene setting, this tremendous property is the...
Ke Alaula Hale 7 – Private & Secluded | Onsite Staff & Daily Housekeeping
This centrally-located 3-bedroom, 3.5 bathroom private home is a short 6-minute golf cart ride from the heart of the Four Seasons Resort. Designed for convenience and uncomplicated family living for up to 6 guests, this property offers a vaulted, wood-beamed great room...
Maui Resort Rentals: Honua Kai Hokulani 645 - Stunning 6th Floor 2BR w/ Fantastic Ocean Views!
Set in the serenity of the Hokulani Tower interior, Hokulani 645 boasts impressive ocean views from its prime 6th-floor location high above the palm trees that often obstruct the view of lower floors. The suite's expansive 200+ sq ft lanai also overlooks the lush...
Kiahuna Plantation Resort 162 Ocean View 1 Bedroom
- Second floor condo with lanai overlooking the great lawn and out to the ocean- Walk-up, no elevators- Tropical beach décor and original artwork by Robin McCoy throughout- Tile and wood flooring throughout- Updated kitchen includes Corian countertops and stainless...
KHV 36 Beautifully Remodeled Direct Oceanfront 3BD Kahana Condo, Steps to the Beach and Pool!
Kahana Village 36 NEW LISTING Spectacular 3Bedroom Beachfront Condo in Kahana with Amazing Ocean Views, and Privacy! FREE daily activities included with your stay value up to $570! Complimentary admission, every day of your stay*: Whale Watch (seasonal), Dinner Sunset...
Maui Resort Rentals: Maui Kaanapali Villas 606 - 2BR Deluxe Oceanview Penthouse w/ Built-In BBQ & Panoramic Ocean Views!
Maui Resort Rentals is proud to present this jaw-dropping 6th-floor Deluxe Oceanview Penthouse Suite at Maui Kaanapali Villas—newly launched on 3/10/25 to start taking bookings beginning March 22nd, 2025!Never before available for vacation rental, Maui Kaanapali...
Fabulous Poipu 7 bedrooms for 16! Amazing pool! New Listing
New Listing!! The Listing is made up of two separate townhomes just steps apart!This fabulous property located in wonderful proximity to Brenneckes, Poipu, and Kiahuna Beach!Surrounded by a championship golf course, the property enjoys a prime spot on Kauai’s sunny...
2 Bed 2 Bath 2 Parking at Cove Waikiki
Spacious 2 bed 2 bath 2 parking, end unit. A perfect home away from home that you will instantly fall in love with, and never want to leave! It sleeps 4, with one queen bed in the primary and two twin beds in the second bedroom. There is an AC unit in each room, free...
North Shore Rustic Country Lodge 2-Story Yurt By Beach Waialua Haleiwa Glamping
Escape to this Tropical North Shore Island Nature Rental Retreat! 2.5 blocks to the beach & famous surf breaks. Rental is a 2-Story Yurt with a generous 1500+ square foot open-concept floor plan. Sleeps up to 11 people. Features kitchen & full bathroom amenities. Close...
Ilikai Two Bedroom, Two Bath Ocean View 8th Floor Corner
Corner suite with 2 balconies, 2 bedrooms & 2 bathrooms at the Ilikai Resort, a luxury high end condo with incredible views of the ocean, sunsets, lagoon & marina. Great fireworks show views every Friday night at 7:45pm. Upgraded and beautifully furnished complete with...
Charming Ilikai Marina Studio, Great Location In Waikiki!
Located within the Ilikai Marina, this condo is located on the 14th floor. You'll love the convenient location in Waikiki, close to the beach, Ala Moana Shopping Center & the Waikiki strip!KITCHEN- Refrigerator- Electric Range- Microwave- Dinnerware, Glassware,...
Maui Resort Rentals: Honua Kai - 6 Total Bedrooms, Stunning 3rd Floor Ocean Views!
This premier 6-bedroom offering combines three neighboring 3rd-floor two-bedroom suites to create the perfect place for your group to gather, reconnect, and celebrate. Konea 303 and 305 occupy a fantastic interior courtyard location directly next door to one another and...
Just What You Were Looking For! Short Drive to Honolulu Zoo and Kuhio Beach!
In the heart of Waikiki near amazing beaches and attractions!This listing is for a room within a hotel.✦ Your room is 226 sq. ft, equipped with complimentary toiletries, TV.✦ Daily cleaning services included in the nightly price.There are a few additional details to...
Private Oceanfront Ohana Retreat Near Hanalei!
Enjoy the very best of Kauai’s north shore from this beautifully remodeled cliffside getaway in the heart of Princeville! Perfectly situated just minutes from Hanalei Bay & some of the world's most iconic surf spots. Step outside to enjoy warm trade wind breezes,...
New Listing! Villa with an island charm interior
Welcome to Kapalua Ridge Villas 2712 – a bright and breezy 1-bedroom, 2-bathroom ground-floor villa that comfortably sleeps up to 6 guests. Step inside to discover an airy, open-concept living space with A/C, and large windows to showcase serene ocean and garden...
Kaanapali Alii | 283
Surround yourself with ocean views from this two-bedroom condo located on the eighth floor. Both bedrooms, along with the living room, dining room, and kitchen all have large windows that look out over the ocean. Step out onto your lanai to not only gaze out at the...
1BR/1BA Ocean View Condo with Sea Turtle Sanctuary On-site
Amazing ocean views. Whales, turtles, rainbows and sunsets can all be seen from our lanai!Mahina's lush gardens are kept immaculate for you to enjoy them as much as the butterflies and birds!View the ocean while relaxing in the beautiful pool just steps from the front...
Spacious Partial Ocean View W/Lanai and A/C - Bamboo Waikīkī Hotel #1006
Castle Bamboo Waikīkī Hotel #1006 - Minimalistic and excellent use of space with pops of color featured in artwork featuring local tropical sights. The functional layout is furnished with premium furniture that allows for plenty of space for storage and...
Maui Resort Rentals: Honua Kai – Incredible 5 Bedroom Oceanview Gem, Interior Courtyard, Sleep up to 16!
This 5 bedroom gem combines one of our very finest 3 bedroom ocean view residences with a partial ocean view 2 bedroom suite located directly next door. It is perfectly suited to larger groups or families of up to 16 guests.The generous combined 3000+ sq ft square foot...
4BR Mokulua Seaside w/ Private Studio, Steps to the Beach
Mokulua Seaside by Gather is a refined oceanside escape that brings together luxury, space, and the beauty of Lanikai. Just one house from the sand on Kailua’s coveted Mokulua Drive, this four-bedroom, four-bathroom retreat spans 3,316 square feet of interior living...
Kapalua Bay Villa 27B2 Gold Oceanfront 2 Bedroom
- Villa closest to Oneloa Beach- Split level loft style villa with no stairs between parking and front door- Tile floors throughout- Updated kitchen with granite counters, farmhouse sink includes – fridge with ice maker, stove/oven, microwave, dishwasher, cookware,...
Tropical Bliss in Kailua
Welcome to your dream retreat in Kailua, a sun-drenched haven where tranquility meets convenience. This charming unit is part of a thoughtfully designed duplex, offering a perfect balance of privacy and community. Whether you’re here to relax, explore, or work, this...
Hilton Grand Vacation Club Resort/Spa Lagoon Tower
This 1 bedroom, 1 bath villa features a king bed in the master bedroom. The spacious living area includes a separate dining area, large television with cable and DVD player, and a queen-size sleeper sofa. Our 1-bedroom plus suite features all the comfortable features of...
Relax in Your 2 Amazing Units w/Partial Ocean Views, Pool, Minutes to Honolulu
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...