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.
Top-floor Maui condo with mountain, ocean, and golf course views. Sleeps six!
This golf front property with its premier location offers peace and serenity to create the perfect Hawaiiana. The spacious lanai provides extra room for relaxing and taking in the splendor of the sun setting over the Pacific.Incredibly comfortable!! Relax on your own...
KBM Resorts | FREE CAR | Honua Kai Konea | Ocean view | 2-Bedroom Condo with Fantastic Location! HKK-203
** 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...
BIG ALOHA & AWESOME VIEW AT THIS HAWAIIAN HOME!
~Breezy Spacious and Welcoming Vacation Home~This Hawaiian home sits up on the mountain with unbelievable, panoramic views of the Pacific Ocean, Diamond Head, Waikiki, and downtown. Watch sunsets, fireworks, whales, and rainbows from the lanai. Situated only 2 miles...
Gorgeous Oceanfront 2 Bed/2 Bath Condo with A/C at Kona Bali Kai Resort Unit 306
Your home away from home in Kailua-Kona with 2 gorgeous bedrooms featuring 2 king beds. This fabulous 3rd floor oceanfront condo offers all the essentials for a comfortable stay, including WiFi, AC, and full-size washer/Dryer. The cool vibe of the space is perfect for...
Best Value - Beautiful remodel - Whole Unit A/C - Ocean Views - Best location
Spectacular remodel. All living areas have been upgraded. Whole unit air conditioning and oversized king bedroom. Ocean views + best Poipu location. With all the special touches in this owner managed condo, Poipu Kapili 39 will fast become your home away from home.Bring...
407 - Gorgeous Oceanfront one bedroom unit!
This fourth floor unit is a luxuriously appointed fully remodeled oceanfront property located on the sought after ocean side of the elevator. It is a one bedroom, one bathroom unit (504 sq ft plus lanai) that has spectacular ocean views from the living room, dining,...
Pili Mai Family Condo 14L, 4 bedroom, 3.5 bath, Central AC, Spacious Lanai
Pili Mai is the south shore's newest development and adjacent to Poipu's ocean view Kiahuna Champion Golf Course. Spacious living is found in this beautiful 4 bedroom, 3.5 bath retreat with plenty of room to spread out and call home. Perfect for multiple families and...
Pristine and Charming - Walk to Beach and Town - Sleeps 4
Our charmingly furnished house with traditional Hawaiiana decor provides all the comforts of home in the world's most spectacular setting on Kauai, the 'Garden Island' of Hawaii. You will seldom need your car after arriving as charming Hanalei village is within walking...
Hale Kamaole 328 Third floor condo, easy access to best beach on Maui!
Tennis court, garden and Ocean View. This condo has a king bed in master bedroom, queen hide-a-bed in loft area. Living room has nice, comfortable, rattan furniture with an air conditioner in the living room. Downstairs bedroom has two twin beds. Very modern, new...
Beachfront Condo w/Partial A/C, Lanai, Ocean Views, Free WiFi, Shared W/D, & BBQ
Kuhio Shores 208Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Get your Hawaiian vacation started out right with incredible ocean views, modern and updated living spaces, and...
Ocean View Mid Waikiki 1 Block to the Beach
Escape to a delightful 2-bedroom apartment in Honolulu and experience luxury living in the heart of Waikiki, just 1 city block to the beach!This lovely space features 2 queen beds, 1 bunk bed, 2 bathrooms with a bathtub and shower, and even a cozy office nook features...
Aloha Condos, Kona Coast Resort, Townhome 7-106, Ocean View, AC
Welcome to Tom & Teresa’s Townhouse — your Big Island retreat with ocean views, resort amenities, and relaxed island charm. This spacious 3-bedroom, 3-bath luxury townhome at Kona Coast Resort offers over 2,000 sq. ft. of air-conditioned comfort — ideal for...
Kauai Oceanfront, Poipu 'Jewel on the Sea', AC, swimmable beaches, Kuhio Shores
Kuhio Shores, our 'Jewel on the Sea,' on Kauai's Gold Coast, is an oceanfront dream. When we first walked into what was to become our new home in Kauai, the views of the ocean, coastline, and lush green hills and palms took our breath away! Located on Lawai Beach or...
Island Chic! Ground Floor Lanai, Modern Kitchen, WiFi, Laundry+AC–Halii Kai Waikoloa 17H
Style, space and homey perks wow in this 1,930 sq ft island-chic home with master bed/bath combo, laundry room and open gourmet kitchen to prep meals for sharing on the ground floor lanai. Enjoy air conditioning, ceiling fans, HD (high definition) flat screen TV's and...
Hale Kahili Ohana: 3 BR Villa w/Pool + Vivid Views
For those desiring larger accommodations, Hale Kahili Ohana is able to be combined with Hale Kahili Nui for a Hale Kahili 8 Bedroom Estate experience.Brimming with tropical ambience and contemporary charm, this delightful new 3BR/3BA villa is beautifully furnished,...
Luxurious DistantOcean View Villa
THIS IS THE BEST VALUE ONE CAN GET AT THE 5 STAR ACCOMODATIONS AT THE BEACH VILLAS AT KO OLINA! Located in the Beach Villas at Ko Olina, within the Ko Olina resort and Marina, this relaxing 2 bedroom 1200 sq ft totally upscale villa has mountain and distant ocean views....
Mana Kai 601, Best Location in Building, on Best Beach
Location! Location! Location! The Mana Kai Resort is located right on one of the nicest beaches on Maui. It is 'Right There' on the beach with an unobstructed ocean view!!! Just fade off to sleep to the sounds of the surf. The ocean water is warm and clear, and the...
Recently remodeled 2 bedroom Ocean Front Building 1 at Kona Makai.
Come and enjoy our little Piece of Paradise in one the most beautiful complexes in Kona. Located just one mile south of the town of Kailua-Kona on Alii Drive. The unit, 1204, is on the second floor of building 1, the best building in the complex with ocean views from...
Evergreen Cottage @ Maui Adventure Villa
Surrounded by green with ocean & mountain views, is a quiet, cozy and private retreat with 2 separated spaces (studio + screen porch) taking in pleasingly mellow sounds of nature! Locally-favorite beaches, hikes, towns and restaurants just minutes away by car.The...
Kamaole Sands 1-407, Partial OceanView, Corner Unit, King Bed, AC, Kamaole Beach
New Split Air-conditioning System in all rooms! Welcome to our 2BR/2BA corner unit with partial Ocean View located at the Kamaole Sands in South Kihei. Just steps away from Kamaole Beach park and close to shopping, dinning and golfing.2BR/2BA corner unit with partial...
Heart of Waikiki With Partial Ocean View! Washlet! AC!
Regency on Beachwalk #71 – 255 Beach WalkYou'll appreciate the convenient location of this fully-furnished 7th-floor end condo (693 sq. ft. plus two lanais with tables and chairs, for a total of 910 sqft) at Regency on Beachwalk, right in the heart of Waikiki and...
Fabulous Waikoloa Colony Villas 3 Bdrm/3 Bath Condo
You are sure to enjoy a fantastic memorable vacation at our Waikoloa Colony Villa 3 bedroom, 2 1/2 bath townhouse at the highly popular Waikoloa Beach Resort development on the sunny Kohala Coast. This 1699 sq. ft. villa is just steps to the beautiful resort pool,...
D211 Quiet & Private 2br2ba near Wailea 2025 Discount 10% 7 nts or more.nnnn
Maui Kamaole is a luxurious low rise townhouse style resort on 23 acres. It sits on a hill overlooking the ocean on the south Maui coast. It is landscaped with lush tropical plants and trees. It boasts 2 beautiful swimming pools and spas. The lower pool area is adjacent...
New listing! Kona Makai, #4205, Ocean Views
Sunset Haven at Kona Makai is a charming one-bedroom, one-bathroom property with an updated kitchen and room for up to four guests. Enjoy ocean views from the lanai and breathtaking sunsets. The oceanfront amenities include a pool, BBQ area and stunning oceanfront...
One-Bedroom Condominium at Kiahuna Plantation, Ocean-Front Property, Poipu Kauai
One-bedroom garden-view condominium at Kiahuna Plantation in Poipu Beach, Koloa, Kauai. On the sunny side of Kauai. Unit number 428 in building 41 (second level of a three-level 18-unit building). Beautiful mahogany trim throughout, matched by new sapele cabinets in...
🏖️ Golf Discount Included | Conveniently Located | AC & WIFI | vrKCV
vrKCV - Fairway Villas Waikoloa B21, Professionally Managed by Kona Coast Vacations Experience Tranquility at Fairway Villas B21Nestled along the sun-kissed Kohala Coast, Fairway Villas B21 offers the perfect blend of elegance and modern comfort within the renowned...
🏖️New Listing | Walking Distance to Shops, Food & Beach! | vrKCV
vrKVR - Halii Kai 10B, Professionally Managed by Kona Coast VacationsHali'i Kai 10B - Your Piece of ParadiseHaili'i Kai 10B is a premier ocean view property inviting you to start your vacation mornings with a cup of Kona coffee on your lanai overlooking fabulous ocean...
KBM Resorts | FREE CAR | Honua Kai Hokulani | Ocean view | 2-Bedroom Condo, Spectacular Huge Lanai! HKH-648
** 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...
Unobstructed Panoramic Ocean View, Completely remodeled, Split system A/C
This ground-floor unit is located in a 15-unit building less than 80 feet from the ocean. Sit on the spacious lanai and watch dolphins and whales followed by breathtaking sunsets and an occasional 'Green Flash' through the palms.This condominium permits you to enjoy...
Grand Oceanfront Gated Estate on the Hamakua Coast
Experience the magic of this breathtaking oceanfront gated estate. Watch dolphins, whales, and cruise ships sail by. Feel the cooling Tradewinds where they first reach the Hawaiian Islands on your skin.Located in the heart of the Hamakua Coast, this is more than a place...
4 bedroom/ 3 bath luxury home with A/C, steps to community pool, oceanview
* Same 5 Star Holua Kai #9 (now under new management)* Central A/C * 4 bedrooms (3 rooms with kings and a double twin room) * Loft with queen Murphy bed* 3 full bathrooms with granite countertops* Backs up to golf course* Walk to Keauhou Bay* Ocean views* Directly...
Absolutely Oceanfront/ SimpleRuralHome/ AC rooms/ 30 day rental
**This home is offered as a monthly rental, however full month occupancy is not required. Please "Contact Host" to see if your dates are available.For the traveller seeking a more authentic experience of Hawai`i is Hale Makani Kai, "home of the gentle ocean breeze."...
Wailea Ekolu 310 - Molokini to West Maui Ocean View, Modern Renovation, Split AC
Welcome to Wailea Ekolu 310, experience breathtaking, panoramic ocean views from main living area and over-sized lanai of this spacious single level luxury condo, in the heart of Wailea and convenient to world class golf, tennis, restaurants and shopping. Sweeping and...
Honua Kai Resort- Konea 329 3 Bed, 3 Bath, Ocean Views
Konea #329 is one of the best locations in the resort. The third floor view provides beautiful views of the property, looking out over the landscaped grounds to the pools and Kaanapali Beach across Auau and Kalohi Channels to the island of Lanai.This unit faces the...
Direct Oceanfront Studio With Private Lanai
Enjoy spectacular unobstructed 180-degree views from our direct oceanfront vacation rental studio condo at the Valley Isle Resort, located directly on the beach in beautiful West Maui. Swim, snorkel, relax by the heated swimming pool or just enjoy the breathtaking...
"Magical View" oceanfront condo Lae Nani #521
2-Bedroom, 2-Bathroom Oceanfront Vacation Rental on Kauai with a Magical View! AC in Bedrooms Just Installed!E komo mai i kēia Lae Nani! Welcome to this beautiful point, a peaceful and lovely haven on the shores of Wailua, Kauaʻi.This second-floor condo is located in...
Beachfront Oasis for Two on Sugar Beach in Kihei - Kealia Condominiums #302
Kealia 302 offers beachfront living right on Sugar Beach! This beach is known as the best walking beach on Maui. And after a full day of sightseeing, shopping or other activities, you can fall asleep to the gentle sound of the surf. It's the best sound machine in the...
Newly furnished house with mountain & waterfall views, balcony & washer/dryer
Hale Carly & Lia LaniOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Beautiful views of the mountains and multiple spaces to come together make this newly updated and furnished home...
OCEAN VIEW 2 BED - 2 BATH AMAZING SUNSETS & WELL STOCKED WITH ESSENTIALS
Nothing but rave reviews from our guests after a stay at our ocean view condo. Come enjoy the amazing picturesque sunsets at Kona Makai. Your dream vacation begins the moment you arrive. You can start and end your day on the large lanai overlooking the beautiful view....
Lowest fees you'll find-Coastal design-Amazing Value-2 Bedroom 2 Bath-Cold AC
Kahana Sunset C3 Welcomes you with much ALOHA....This unique condo is a beachfront property on the world-famous West Coast of Maui between Kaanapali and Kapalua. Kahana Sunset fronts one of Maui's most romantic white sandy beaches, nestled on protected Keonenui Bay,...
Large Princeville home with pool and jacuzzi on the Makai Golf Course
Located on the Makai Golf Course, this Princeville home is a large groups paradise. It features a pool, spa, ample indoor and outdoor space, two expansive decks, and a vast modern kitchen. With six bedrooms, including a bunk room, it’s well-suited for families with...
Ocean & Golf Views in Wailea - Designer 2 Story Condo w/ AC system, Wifi
The Address to Wailea Ekolu #314: 10 Wailea Ekolu Pl. #314 Kihei HI 96753*Professionally Cleaned Condo, No-Contact Check-In/Check Out*Location & luxury combine to make this Wailea Ekolu condo a perfect home away from home. Only minutes from Maui’s best beaches,...
Truly Oceanfront Townhome! 180 degree ocean views - Ground level lawn and lanai
Do you dream of a private, oceanfront villa? This two-story, duplex townhouse offers spectacular unobstructed ocean views from the lanai, the kitchen, the dining/living room area, the upstairs bath, and the master bedroom picture window, WOW! Arguably the best location...
Beautiful, Family Friendly 2 Br 2Ba Across Street From Beach.
Beautiful 2 bedroom 3 bed unit offers a quiet getaway and island view. Newly updated furniture and decor. Each building has a pool, tennis courts and barbecues. Quick stroll across the street to Beautiful Charley Young Beach. Great Shopping and dining options are a...
Maui Resort Rentals: Hokulani 820 – Top Floor 2BR w/ Ocean & Mountain Views + X L Balcony!
Hokulani 820 is a luxurious two-bedroom penthouse ocean view corner suite and one of the few offerings at Honua Kai that affords views of both scenes that Maui is famous for... the relaxing blue Pacific Ocean and the majestic West Maui Mountains. Further adding to the...
Mana Kai 314 - Experience Stunning Coastal Views on Keawakapu Beach, Split AC
Mana Kai 314 is a beautifully upgraded two-bedroom condo offering a serene retreat for up to four guests. With panoramic ocean views from the living area and private lanai, this unit provides a front-row seat to Maui's stunning sunsets and soothing wave sounds. Inside,...
Spacious and Renovated Waikiki Condo With Full Kitchen and Ocean Views
Renovated, clean and spacious studio in Waikiki. Unit is on 38th floor of the Hawaiian Monarch Hotel/Condo building and comes with queen bed, full kitchen, full bath and amazing ocean, canal, diamond head and mountain range views. Walk to Waikiki beach, Waikiki strip,...
Waikoloa Colony Villas 204-Golfers Retreat with Gold Golf Membership Discount
Newly remodeled 2 bedroom, 2 1/2 bath Waikoloa Colony Villas townhouse located off the 9th hole of the Waikoloa Beach Nine. Discounted GOLD GOLF KINGS' CLUB MEMBERSHIP. Book this villa and you will be able to set up your tee time and golf at discounted rates. This unit...
Kaha Lani #304: Coconut Coast • Pacific Sunrise View • 1BR/1½B • Top Level View
Penthouse, 3rd floor walkup condo with magnificent ocean vista from your living room and large private lanai. Enjoy the quiet privacy of this intimate condominium on beautiful Kauai's Royal Coconut Coast. The quaint town of Kapa'a is a few miles North of the...
Hale Hapuna - Poipu's Best Ocean and Mountain Views
Whether you’re traveling with a large family or group of friends, Hale Hapuna is the perfect choice. It offers the ideal setting with approximately 5,000 square feet to spread out. Extra spacious living areas offer plenty of room to relax and enjoy each other’s...