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.
Sparkling Hawaiian Monarch Studio | Pool + Gym
Beautifully renovated Waikiki studio in a fantastic location at the Hawaiian Monarch. This unit features ac, smart tv, wifi and cable a short walk from Fort DeRussy Beach Park, Hilton Hawaiian Village, Ala Wai Canal and more. The Hawaiian Monarch is a secured building...
Sea Shore 41 Private Studio in Waikiki, 1 Block to Beach
Tropical Oasis Retreat at the Sea Shore 41 in the Heart of WaikikiEmbark on an unforgettable Hawaiian adventure with our Private Studio in Waikiki, a haven that has garnered rave reviews from delighted guests. The studio offers the perfect blend of comfort, convenience,...
Pu'ukala Sunset Estate w/ Amazing Ocean Views! by RedAwning
Escape to the breathtaking beauty of the Big Island and make your vacationdreams come true in this splendid 3-bedroom, 2-bathroom vacation rental home.Nestled in the heart of Kailua-Kona, this tropical paradise offers an open andspacious interior, complete with all the...
Great Location In Wakiki, Walking Distance To Beach, Shopping, Dining!
This gorgeously renovated condo has been completely transformed with modern upgrades and thoughtful design. The open-concept kitchen boasts sleek finishes and high-end appliances, including a sharp microwave drawer. The spacious living area flows effortlessly into an...
Princeville Paradise 1BR Suite @ Wyndham Ka Eo Kai
Summary:Escape to a serene South Pacific paradise overlooking the breathtaking Anini Bay on the mesmerizing north shore of Kauai. Our resort offers a tranquil retreat where you can immerse yourself in the natural beauty and tranquility of the island. With stunning...
Kapalua Ridge Villas Ocean View 2 Bedroom
Ridge Villas Ocean View 2 Bedroom 2 Bath- The Ridge Villas are perched high above with views of Kapalua Bay Course’s fairway- Fully equipped kitchen includes stovetop/oven, microwave, refrigerator, coffeemaker, cookware, tableware- Master bedroom with 1 king bed and...
1BR Condo near Waikiki Beach w/ Private Lanai
Escape to this one-bedroom condo at Sweetwater at Waikiki, just steps from the beach. Designed for comfort and convenience, this retreat features a queen-size bed, a Murphy bed in the living area, and a private lanai with stunning views. Guests enjoy access to a pool,...
Aqua Aloha Surf Waikiki 704 Deluxe Studio with Lanai and Partial City Views
Aqua Aloha Surf Waikiki 704 Deluxe Studio with Lanai and Partial City Views located just 2 Blocks to Waikiki Beach, (1) Full/double bed, (1) Twin bed + (1) Queen sofa sleeper, sleeps 4, 367 St FtAqua Aloha Surf Waikiki brimming with island personality offers a range of...
PK A108 Remodeled OceanFront w Panoramic Ocean Views
Papakea A108 NEW LISTING Remodeled OceanFront Papakea 1Bedroom with Panoramic Ocean Views for Front Row Sunsets and Year Round Indoor-Outdoor Living FREE daily activities included with your stay value up to $570! Complimentary admission, every day of your stay*: Whale...
Quaint Waikiki Monarch Studio | Pool + Gym
Enjoy beautiful mountain and canal views from this quaint studio in a fantastic location at the Hawaiian Monarch in Waikiki. This unit features ac, smart tv, wifi and cable a short walk from Fort DeRussy Beach Park, Hilton Hawaiian Village, Ala Wai Canal and more. The...
Easy-Going Style w/Lanai, Kitchen Ease, WiFi, Washer/Dryer–Kamaole Sands 5314
This air-conditioned 818sf suite says “welcome home” after a day of hiking and ziplining. Families and friends appreciate the privacy, space and comforts of a complete kitchen, furnished lanai, living area, ceiling fans, flat screen TVs, DVD, WiFi and washer/dryer....
Kailua Bay Resort#4-204: Heart of Downtown, Walk to everything!
Experience the ease and energy of island living from this inviting second-floor walk-up condo at Kailua Bay Resort, Unit 4-204, perfectly positioned in the heart of downtown Kailua-Kona. From the moment you arrive, you’re immersed in the true Kona lifestyle—sunshine,...
Mountain/city-view condo with rooftop pool, balcony, & W/D - 30-night minimum
Pavilion at Waikiki 1804 - 30 Night MinimumOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Make the most of this condo's excellent location in the heart of Waikiki, just a short...
Ridge Villas Gold Ocean View 2 Bedroom at The Kapalua Villas Maui
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...
Lovely Oceanview House@Pupukea in Paradise / Surfers HQ
Awesome sunset views included ;-) Close to the Ocean yet far enough away to not be bothered by traffic noise from Kam-Hwy. Get ready to fall in Love with this charming Pupukea country home. Clean, spacious, airy.Open beam cedar and redwood construction with wrap-around...
Lovely Luana Waikiki Studio | Private Lanai
Relax in paradise in this sparkling clean, beautifully maintained hotel-style unit at the wonderfully located Luana Waikiki. With a private lanai overlooking the city, this brightly remodeled studio is steps away from Waikiki Beach Park and the world-famous Waikiki...
1BOV2 Aston at the Waikiki Banyan: Deluxe 1 Br w/Kitchen & Ocean Views
Resort Project: The Rec Deck Swimming Pool and Two Jacuzzi’s located on the 6th floor are closed for construction/renovation until the end of June 2026. Important: Construction may cause intermittent noise during your stayAston at the Waikiki Banyan: 1-bedroom Deluxe...
Cozy 1-bedroom condo with AC, Wifi, Laundry rooms with 24 hr on-site security.
Experience Honolulu like a local in this 1-bedroom condo. The space features 1 queen bed, AC, Fioptic Wifi , dSmart tv, refrigerator, various small appliances including coffee pot, rice cooker , microwave. We provided basic toiletries bath wash, shampoo coditioner. The...
Cozy Hawaiian Monarch Studio | Pool +Gym
Take in the beautiful views of Diamond head and Waikiki beach from this cozy Hawaiian Monarch studio with all the essentials. This unit features ac, flat screen smart tv, wifi and cable. A short walk from Fort DeRussy Beach Park, Hilton Hawaiian Village, Ala Wai Canal...
Stylish & Modern Princeville Getaway Near Hanalei!
Discover the very best of Kauai's north shore from the comfort & convenience of this modern private retreat! Perfectly situated in the heart of Princeville just minutes to Hanalei Bay, enjoy warm trade wind breezes while relaxing on the beach, iconic surf spots, hiking...
Partial Ocean View Lanai! Relaxing 1BR in Waikiki w Parking Included!
Great location in the heart of Waikiki! Enjoy your Stay at your own Comfortable 1 Bedroom /1 Bath / 1 Free Parking unit with Beautiful + Bright partial Ocean Views. 3 Bedding - 2 x Full Beds in the bedroom + 1 x Full Sofa BedTrash Chute, Coin/App operated laundry...
Modern Surf Chic Studio at Hawaiian Monarch | Pool
Gorgeously remodeled, modern surf-chic Hawaiian Monarch studio with Ala Wai views and a fantastic location. This unit features ac, large flatscreen smart tv, wifi and cable. A short walk from Fort DeRussy Beach Park, Hilton Hawaiian Village, Ala Wai Canal and more. The...
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...
Wailea Ekolu Village 1404 - 1 Bedroom Ocean View Condo
Wailea Ekolu 1404 is a beautifully appointed one-bedroom, two-bathroom vacation rental that offers an idyllic escape in Maui\'s popular town of Wailea. This elevated condo on the second floor boasts stunning ocean views and a serene ambiance. Upon entering, guests eyes...
Relaxing Kalakauan 1-Bedroom | Private Lanai
This family-friendly vacation home is tucked away at the beginning of the Waikiki strip and features secured entry. This 1-bedroom, 1-bathroom offers easy access to the Waikiki Strip, Hilton Hawaiian Village, Fort DeRussy Beach Park, world-famous Waikiki Beach, Hawaii...
Private Princeville Guest Suite Near Hanalei Bay!
Enjoy the very best of Kauai from the comfort & convenience of this private guest retreat! Perfectly situated just minutes from the breathtaking beaches of Hanalei Bay, Anini & Tunnels, enjoy a scenic hike through the lush north shore trails or for golf enthusiasts, the...
1 Marriott Maui Ocean Club Resprt and Spa, Hot Tub!
Discover Marriott's Maui Ocean Club – Molokai, Maui and Lanai Towers, a beachfront vacation ownership resort along scenic Ka'anapali Beach in West Maui. Enjoy easy access to outdoor adventures, from snorkeling and paddleboarding to visiting Haleakalā Crater and historic...
Waikoloa Village 2 Bedroom Sleeps 6
Please Send An Inquiry Before Booking By Clicking The Contact Host Tab.The resort is the perfect destination for your Hawaiian vacation. Enjoy the many amenities available 2 swimming pools, Barbecue grills and picnic areas are scattered throughout the property. Tennis...
Two Bedroom, 2-Story Townhome at the Exclusive Mauna Lani Resort
* Beautiful 2 Bedroom, 2-story townhome at the exclusive Mauna Lani Resort* Nicely furnished in Tommy Bahama decor with views of the golf course and outdoor lanai space* 2-story, 2.5 bathroom unit for extra privacy* Living room offers a sofa sleeper, HDTV and DVD...
Royal Kahana Maui 1103 Ocean View Studio
Experience breathtaking sunsets from this inviting ocean-view studio, perfect for couples or small families. Unit 1103 Ocean View Studio• 11th floor studio with balcony overlooking the ocean and the island of Molokai • Studio kitchen includes microwave, stovetop/oven,...
Kapalua Ridge Villas Gold Ocean View 1 Bedroom
Ridge Villas Gold Ocean View 1 Bedroom- The Ridge Villas are perched high above with views of Kapalua Bay Course’s fairway- Fully equipped kitchen includes stovetop/oven, microwave, refrigerator, coffeemaker, cookware, tableware- Bedroom with 1 king bed or 1 queen bed-...
Long Term Rental Maalaea Yacht Marina Oceanfront
Paradise awaits you at Maalaea Yacht Marina, Maui. This third floor oceanfront corner unit has extra-large windows and an expanded wrap around lanai (balcony) that offers breathtaking unobstructed views of the Pacific Ocean and Maalaea Harbor.INQUIRY ONLY: Long-Term...
The Westin Princeville Ocean Resort Villas - 2BR/2BA, Sleeps 6
Your comfortable two-bedroom lockoff villa at The Westin Princeville Ocean Resort Villas is a stylish, intuitively appointed retreat combining a one-bedroom premium villa and a studio premium villa. You have the option of entertaining a villa full of guests or reserving...
Napili Point | 3 FREE Rental Cars | KBM Resorts | Water Front | 3 Units, 3 Bedrooms | NAP ML-2576
** 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...
Nanea Kai Villa - Luxury Beachfront Estate in Hawaii Kai
At Nanea Kai Villa, ocean breezes, Diamond Head views, and beachfront living come together in a spacious four-bedroom retreat. This two-story estate offers 4,700 sq. ft. of refined island living, complete with a heated saltwater pool, spa, and private beachfront access...
21Fl Near Waikiki Beach w/ Mountain Views, Parking
Aloha from Midway Vacations, your local experts in paradise! Enjoy spotless, well-kept homes, island hospitality, and 24/7 support for a worry-free Hawaiian escape.Wake up to gentle island breezes and scenic mountain views in this 600 sq ft 21st-floor 1-bedroom condo at...
MAUI IS OPEN! Come visit! Oceanfront Westin Nanea- Luxurious Two Bedroom Villa
*We are able to offer weekly reservations with check in on Friday, Saturday and Sundays only.* Newly opened in Spring of 2017, this stunning resort sits on 16 acres of Ka'anapali Beach, and has spectacular grounds and first class amenities. "Nanea" is a Hawaiian word...
Cozy Queen Bed Studio 2 mins Walk to Waikiki Beach
Your cozy getaway awaits in Honolulu at this soothing Waikiki Grand studio. Guests will find a comfortable studio style living area featuring a queen bed, perfect for relaxing after a day of exploring. The space includes a well-equipped bathroom with a hair dryer 7...
Luxurious 2-Bedroom Ocean View Escape at Westin Ka’anapali Ocean Resort Villas
Experience the pinnacle of tropical luxury with a 2-Bedroom Lockoff Ocean View Villa at Westin Ka’anapali Ocean Resort Villas, where breathtaking vistas and family-friendly amenities come together to create an unforgettable Maui getaway. Perfect for larger groups or...
KP 18 Sweeping Ocean Views | AC Comfort & Pool
The Space:Welcome to your island escape at Kaanapali Plantation 18, a peaceful hillside retreat offering sweeping ocean views, tropical breezes, and modern comfort in the heart of West Maui.✔ Ocean views ✔ Two ocean facing furnished lanais✔ Central Air Conditioning ✔...
Kaanapali Alii Unit 2102
Kaanapali Alii 21022 Bedrooms | 2 Bathrooms | Sleeps 6 | Partial Ocean View________________________________________ Welcome to Kaanapali Alii 2102, an exquisite Maui getaway where refined design meets breathtaking natural beauty. This one-bedroom partial ocean view...
Brand New Home. Amazing ocean, mountain and coastline views
New Listing Special 5000 mo. Paradise Found Escape to a beautiful 3-bedroom house in Makaha. This phenomenal property was just built and features 1 king bed and 2 queen beds, perfect for a group getaway, retirees or working professionals. One house back from beach....
New Listing! Na Hale O Keauhou, Ocean View
Welcome to your dream vacation at Big Island Na Hale O Keauhou C5, a stunning retreat nestled in the heart of Keauhou in Kailua-Kona.This beautifully designed two-bedroom, two-and-a-half-bathroom villa offers a perfect blend of comfort and luxury, accommodating up to...
Kapalua Golf Villas | 2 Free Rental Cars | KBM Resorts | Large Bedrooms | 2 Units, 3 Bedrooms | KGV ML-1335
** 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...
2 bedroom Waikiki Apt sleeps 6
This roomy apartment is perfect for a family or group. There are two separate bedrooms-both with queen sized beds. Both bedrooms also have a basic desk with chair which can also be used as a vanity table. The living room has a pull out queen size sofa bed. I have...
Old Hawaii Waikiki 1 Bd Free Parking
Step into old Hawai'i, and plan your ideal island escape and book a minimum month stay at this 1-bedroom, 2-bathroom vacation rental in the heart of Honolulu! Centrally located just a half-mile from the island’s pristine Waikiki Beach, this 2nd-floor condo invites you...
Royal Kuhio 2302 - Spacious Upgrade Studio w/ Stunning Mountain Views in Waikiki
Heart of Waikiki - Royal Kuhio (23rd Floor)Address: 2240 Kuhio Ave., #2302, Honolulu, HI 968151 Bed | 1 Bath | Sleeps 4Beds: 2 Full-size beds + 1 Queen sofa bedSize: 436 sq ft + 80 sq ft lanaiView: Partial ocean and mountain viewsKitchen: Fully equipped with oven,...
Partial Ocean-City Luxury Retreat at Sky Ala Moana w/Great Amenities
This property requires a minimum 30-day rental. Book with confidence—professionally managed by Ali'i Beach Rentals, an award-winning property management company.The Sky Ala Moana is Honolulu's newest symbol of luxury, featuring two distinct towers: The Residence and The...
Surfers Paradise w/ Oceanview 29+ nights
Lovely Hawaiian Pole House w/ oceanview on 1.1 Aces w/ fruit trees and ample parking on the property. Up on the hill of Pupukea -- one of the most thought after locations in Hawaii. Away from the traffic noise and fumes on Kam-Hwy, but close enought to get to all the...
Beachfront condo in Waianae, breathtaking view, newly renovated, Mākaha Shore
BEACHFRONT Condo, Makaha shore Beautiful BEACHFRONT condo on Makaha shore, 1 bedroom and 1 bathroom. Enjoy your breathtaking ocean views and sunset views from the bedroom, kitchen and lanai areas.The beach is filled with white soft sand, turquoise clear water, and...