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 Vista Top floor 2-bed condo in central South Kihei Walk to shops and beach
Aloha, A beautifully renovated top floor 2 bed 2 bath, with vaulted ceilings and fantastic amenities. The unit faces Maalaea Bay and the West Maui Mountain. Elevator access to the unit makes it very convenient for all ages; parking is free, no resort fees.Building 3 is...
Spring Savings! Save 15% thru 5/31/25 - Stunning Ocean Views, Steps to the Beach
The perfect Maui getaway! Enjoy breathtaking ocean views from every room except the bathrooms in this beautifully upgraded unit. It features granite countertops, stainless steel appliances, and a fully stocked kitchen. With central AC, an in-unit washer and dryer, and a...
MRR Presents Kaanapali Ali'i 292 - Renovated 9th Floor Corner 2BR w/ Partial Ocean AND Mountain Views!
Boasting stunning partial ocean views in addition to lush vistas of the West Maui Mountains, this luxurious fully renovated 2BR/2BA 9th-floor suite features a highly sought after corner location nestled high above the palms. The space is further elevated by its upgraded...
Whales, Beaches and Sunsets! Come enjoy Maui's most exclusive resorts.
Aloha, Maui is welcoming visitors and need your support by coming to our beautiful island. Enjoy stunning panoramic ocean views and just steps from the beach, pools and spas. Watch sunsets from the lounge chairs on the lanai or from the living and dining room! Our 1600...
Oceanview Top Floor 2BR Suite +A/C, Beach & Pool
Escape to Hale i Lani, your “home in heaven”, at Hanalei Bay 4304 & 4305! Located on a west-facing bluff in Princeville with sweeping ocean & mountain views and A/C in every room, this peaceful top floor retreat is perfect for couples, families, and small...
Makahuena 2102 by Destination Kauai with A/C
E Komo Mai, Welcome to The Makahuena 2102!“The Makahuena” is located on the southernmost point of Kauai. This unique oceanside resort is situated on the edge of a bluff providing spectacular coastal views. This spacious 3BR/2BA ocean view condo has over 1,300 sqft...
Maui Resort Rentals: Honua Kai Hokulani 404, Luxurious 3BR w/ Stunning Ocean & Mountain Views!
Located only one stack back from oceanfront in the closest column to the ocean at the entire resort, this luxurious 3BR/3BA residence boasts stunning ocean views that extend deep into the home’s living area, as well as vistas of the West Maui Mountains. Enjoy a...
Newest Unit * Modern Coastal Luxury Meets Maui *
Aloha! We welcome you to enjoy your newest Maui vacation rental in Kaanapali Beach Resort at the Maui Eldorado Kaanapali H105. Elevated California coastal design meets Maui in this newly designer decorated 1 bedroom vacation condo - perfect for a couple, or a family up...
Maui Summer 2025 -June 15-22 Studio IV & 2bd Oceanview July 12-19 sleeps 8
Last chance summer deal!! I have a studio premium villa Oceanview for Aug 31- Sept 7th 2025 pre-reserved with Westin available to rent. A studio sleeps 4 with a king bed plus a sofa bed with a kitchenette. For Spring Break 2026 I have a Studio OV for March 20-27 2026 &...
Cottage with Private Salt Water Pool
30 night minimum This beautiful recently updated cottage is nestled in the quiet, safe, and upscale neighborhood of Kahala. Excellent location! Just minutes to Waikiki, nearby parks and the pretty white-sand beaches of the East Honolulu coast. Also, in very short...
2 Suite Partial Ocean View Villa - Sunsets, Serenity, Beach runs!
Take a deep breath and relax in our fully stocked villa with all the beach, kitchen, laundry, grill and bathroom amenities taken care of. Enjoy your down time with the birds and breeze on our secluded lanai without a car, road or parking lot in sight.We're in Hali'i Kai...
BIG ISLAND PARADISE-private lanai -pool/spa/low golf rates/access to #1 beaches
Beautifully situated above the Pacific Ocean and Mauna Kea and Hapuna Prince Resorts, at the base of the Kohala Mountains is the setting for your dream vacation on the Big Island of Hawaii. This new 3-bedroom, 3.25-bathroom Villa at the Wai’ula’ula Complex is...
Ko Olina Beach Villas B602 by Gather: Beachfront Villa w/ Sensational Views
Discover the ultimate beachfront living at Ko Olina Beach Villas B602 by Gather. This luxurious two-bedroom, two-bathroom villa on the sixth floor, with space for up to six guests, is located on the tranquil west side of Oahu and embodies the essence of island...
RK 301 Remodeled OceanFront 2BD w Pool and AC
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 Sail, Alpaca Farm Tour, Pineapple Farm Tour, and All Day Electric Bike Rental. (W1)*One ticket per...
Beautiful Luxury Oceanfront Condo-Grnd Floor, Great View, A/C, Wi-Fi, BDRM View
Enjoy cool island breezes, breathtaking ocean views, and whale watching in a fully re-modeled ground floor condo by the ocean. The convenient location in Maalaea leaves you minutes away from beautiful beaches, restaurants, and all Maui destinations. An open layout...
Luxurious Condo with Absolute Best Ocean Views in Kapalua
Visit Paradise on Earth...This privately owned and totally remodeled vacation condominium is located in west Maui's Kapalua Resort. This premier property has the absolute best views of any Kapalua villa in the resort. This updated unit is first class luxury. It has...
Hale Lani – Heavenly Lanikai Hillside Luxury
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 your next dream vacation here at Hale...
Kona Alii#407: Stunning Corner Unit in the Heart of Kona
Welcome to your perfect getaway at Kona Ali’i, located in the vibrant heart of Kona town. This newly furnished 1-bedroom, 2-full bathrooms (yes, 2 full bathrooms!) corner unit on the 4th floor offers a blend of comfort and convenience, ideal for both relaxation and...
Private gated home with 300 Foot private beach front, beach toys and much more!
The Maui Beach House is a two story private beach retreat on a calm and private bay. It is a place of unmatched peace, I tranquility, beauty. This idyllic beach house features wide ocean views from all rooms with a total of over 4,000 square feet. of interior and deck...
Great Location- Quiet Beach, Small Complex, Walk to Bars & Restaurants
Aloha and welcome to the Hale Kai Uli! What exactly is the Hale Kai Uli? In the Hawaiian language hale means house, kai is the ocean and uli means blue. The House of the Deep Blue Sea.The Hale Kai Uli is adjacent to a quiet stretch of sandy beach in sunny Kihei, Maui…...
Oceanfront living - Floor to Ceiling wall of glass
Enjoy oceanfront condo living with all the amenities and added comforts of home. Included is an in-unit washer/dryer, full kitchen, reserved parking space, beach and snorkeling gear, WiFi, cable TV, and A/C. Experience one of the BEST unobstructed ocean views and wake...
Tropical Vibes & Sunset Skies
This peaceful Kaua’i home is filled with vibrant paintings inside and tropical gardens outside. A personal gallery of locally curated paintings. Truly, a one-of-a-kind experience. Explore the island and return to this quiet and very comfortable home. Vaulted ceilings...
Hawaii Life Rentals Presents Puu Poa 307
***DISCLOSURE: Puu Poa 307 is listed for sale. Guest may be asked to accommodate showings of the property with 48 hours notice.Puu Poa 307 combines the serenity of verdant mountain and deep blue ocean views with a newly renovated and thoughtfully designed condominium....
Amazing Oceanview Beachfront Getaway Close to Everything!
Aloha! If you are looking to get away from it all but still be close to everything that Maui has to offer, look no further! Our owner-hosted (no dealing with unresponsive property managers) beachfront 4th-floor condo makes you feel far from it all yet is minutes away...
Hawaiian-style garden courtyard setting across the street from the beach!
This is an end unit on the first floor at the back of the resort complex. You can enjoy the lush gardens and tropical breezes from the spacious lanai. The newly renovated condo has a master bedroom that includes a king size bed. The main living space contains a wall bed...
❤️Luxury 2 BD Condo at Honua Kai Resort on the Beach ❤️
1 Bed & Den (Like a 2 BED), Sleeps 6, Large Lanai, Huge bath with Soaker Tub & Separate shower MauiRentalCondos Aloha! Welcome to Paradise! Important: Although this is a privately owned vacation rental home this complex is zoned "Hotel" so not part of any potential...
<br>🐳Whale Season is Here🐋<br>Book Now!
Aloha 🌺 Thankyou for your inquiry,Its a timeshare so multiple units avail so if you see the calendar is blocked inquire anyway👍🏻 We may have another option!These resorts are amazing 🥰 with Heavenly Beds! Heavenly comforters and Bath Products:) Each Studio...
Alii Villas #332 On Ocean Fantastic View. Watch Dolphins, boats and canoes go by
Come enjoy a fabulous time in an ocean front property in Kailua-Kona Hawaii. This unit is a 2 bedroom, 2 bath home at a premier location at Ali'i Villas. The décor of this unit has been done in cool coastal and has just been remodeled top to bottom. Shoji screens can...
SUNSETYARDS ON SUNSET Point, OPEN APRIL 2025-Sept 2025. almost beachfront.
SUNSETYARDS BEACH HOUSE ON SUNSET POINT. .. this lovely 2-bedroom house offers breathtaking ocean vistas and serene natural scenery that make it ideal for a tropical escape. Nestled just a 7-minute drive from the renowned Banzai Pipeline and a 15-minute drive from the...
20FT WALK TO BEACH/ OCEAN VIEWS/BOOK 7 NIGHTS & GET THE 8TH NIGHT FREE
This large corner villa is located inside the Beach Tower, the closest building to the beach (20ft walk from your condo to the beach lagoon).Promo: Book 7 Nights and you will receive the 8th Night Complimentary (dates may vary based on the season).We have a dedicated...
Spectacular views from this newly remodeled direct oceanfront 2bd/2bth unit.
The building is about 300 feet from the sand which makes it perfect for water sports or nice walks on the beach. The updated kitchen has plenty of counter and cupboard space and is open to the dining area The side view from the dining area overlooks a waterway, upscale...
Incredible Direct Oceanfront Views on Kaanapali Beach!
Direct oceanfront condo with wrap around Balcony: 1 Bedroom, 2 Baths, Sleeps 4. 5th-floor condo on Kaanapali Beach. Luxuriously remodeled, Suite 551 offers plenty of sleeping capacity for up to 4 guests with a king-size bed and a queen convertible sofa-sleeper.This...
Konas#1Rated Oceanfront Pool4 Bdrm Home Walk2Town Ironman Thanksgiving Christmas
Happy Tuesday! Ironman Open 8 nights ….Oct 4 to 19thOct 15/16 to Oct 20 message Oct 27th to Nov 2 …..rare opening…Nov 13 to Nov 23 open 7 nights Christmas 15/16/17 to Dec 29…..10 to 14 nights April 30th to May 6/7Sorry no cancellations, however we may elect to...
Oceanfront 1BR Condo with Spectacular views + Pool.
Spectacular ocean & sunset views at the one-of-a-kind ocean front Maui Kai Resort. The only way to be closer to the ocean is taking a cruise. Located on the 9th floor, the condo offers privacy & 180 degree panoramic view of the islands of Lanai & Molokai. This...
Next Generation / Remodeled-2 Bedroom-2 Full Bath-End Unit-Specials!
Magnificent large 7th floor end unit condo, considered the corner suite, is fully equipped with new furnishings, including barn doors, new ceilings, new bathrooms, new kitchen, new flooring and ultra modern features throughout. This condo has literally been rebuilt from...
2 bedroom home minutes to world class beaches, surf, scuba & snorkeling!
Welcome to Puako Kai Hideaway, a beautifully updated vacation home in charming Puako. Located only minutes away from world class beaches, surf, scuba, snorkeling and golf. Extensive resort amenities, restaurants, shops and farmers markets are a short drive away.This...
The Sacred getaway at Fairway Villas C1! This 3 bedroom, 3 bath condo is new!
Welcome to Sacred Peaks Getaway, a newly renovated and tastefully designed condominium that can comfortably accommodate up to eight guests. This spacious vacation rental features three bedrooms, providing ample space for everyone in your group. The guest bedroom...
5 Beds Downstairs Corner Unit with AC, 3 Pools, 6 minutes to Beaches, Beach Cart
Ideal downstairs corner location on greenbelt in preferred Regency Building 5 and adjacent to beach trail. Enjoy pleasant trade winds in this light & bright condo with portable A/C units in both bedrooms and living area (No central air or split system). This brilliant...
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...
Expansive One-of-a-Kind Retreat - 3 Oceanview Lanais - Makena Surf G 301-302
Makena Surf #G-301-302Welcome to Makena Surf #G-301-302, an expansive and newly remodeled four-bedroom, five-bathroom oceanview penthouse with a private den, located in the exclusive Makena Surf Resort. With elegant design, premium finishes, and three private lanais,...
Wonderful Ocean View –Totally Renovated-On Golf Course
STVR-19-358846 - Relax and pamper yourself in luxury in this well-appointed condo. On the golf course with Spectacular Ocean views. This is NOT your average condo rental! This condo has had an extensive high-end renovation and interior decoration including art from...
Updated 2-bed, 2-bath White Sands unit with ocean views, AC & modern amenities
Turn moments into memories at the iconic White Sand Village unit #301. This beautifully, fully-remodeled, and refurnished property is everything the luxury traveler is looking for. You have a front-row view of Magic Sands in this two-bedroom, two-bathroom corner unit...
*Peace and Serenity*
E Komo Mai! Ho'okipa Rose, Peaceful, Tropical home in the quaint town of Haiku. Lovely 2 bedroom, 2 bath, 1000 sq. ft. cottage located on private, two acre property. Fully equipped kitchen with everything you need to prepare meals. Upscale amenities throughout. Outdoor...
Kaanapali Alii Resort 356
"Alii is the Hawaiian word for Royalty' , and our condo is this and much more, it is Luxury at its Best. Welcome to the Kaanapali Alii Resort! When we say DIRECT OCEANFRONT, we mean it... This unit was completely redesigned and remodeled December 2011. OUR...
Kamahana 19: 2 BR, 2 BA Condominium in Princeville, Sleeps 4
Completely remodeled two bed, two bath private condo. It is aspected towards the golf course and feels more like a home than a condo. Open main living area with incredible tradewind breezes and a a large covered lanai. The kitchen boasts modern appliances and brand new...
Kehena Hideaway Luxury Home
You'll feel well-cared for and cozy in this new two-bedroom home. High-end design and luxury finishes bring art, comfort and beauty indoors; wrapping you in a jewel box of tranquility. The large open deck offers plenty of outdoor living space. The black sand beach of...
Sugar Beach Maui! Direct Ocean Front! Best View! Best Value!
Hello Sugar Beach Resort Lovers! We have just purchased this Direct Ocean & Beachfront Condo in a Spectacular Setting! This condo had a A+ rating for the prior long term owners through one of Maui's largest rental agencies! We are underpricing our condo for our Grand...
Ko Olina Beach Villas 608: Spacious 2BR Luxe Home w/ Ocean Views
Welcome to Ko Olina Beach Villas B608 by Gather, a spectacular sixth-floor beach villa in the serene Ko Olina Resort. This two-bedroom, two-bathroom oasis, with space for up to four guests, is a dream come true for those seeking a tranquil escape in paradise. From the...
🏖️Top Floor with Loft | Ocean Views | Air-Conditioning | Concierge Included
vrKCV - Country Club Villas 305, Professionally Managed by Kona Coast VacationsCome enjoy a slice of paradise in this colorful Kona getaway with spectacular ocean and golf course views from the lanai, living room, kitchen, and primary bedroom! Wake up to the sounds of...
Epic Ground Floor Unit - Step onto Hapuna Beach from Large Lanai w/ Plunge Pool
Rare opportunity to rent an oceanfront condominium within the iconic Mauna Kea Resort. Hapuna Beach Residences C22 is a luxurious 2 BD 2 BA unit + bonus room. Consisting of 1,597 square feet of interior living area, and 1059 square feet of outdoor lanai space with...