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.
BABY BEACH BUNGALOW 2-STEPS TO BEACH - OCEAN VIEW - AMAZING LOCATION, NEAR SHOPS
POIPU-- Kauai-- Vacation Home Rental-- Ho'ona Road-- Baby Beach Bungalow 2 is steps away from a crescent-shaped white sand beach called Baby Beach and is located in a family-friendly neighborhood on Ho'ona Road. We Do Not have A/c, all rooms have powerful ceiling fans...
#17 Large 1/1 Condo | 1 Bed, 1 Bath
Aloha! This is truly a special and unique part of the world. Condo #17, Hale Maluhia (House of Peace), sits OCEANFRONT on the Sea Mountain Resort at Punalu'u Black Sand Beach. It is a spacious separate one-bedroom unit, built in the 'Kama'aina' (Hawaiian bungalow)...
Serene Luxury Golf & Tennis Villa - outdoor pools, hot tub, bbq
Wailea Grand Champions Villas are the perfect place for vacation. Set amid Wailea’s Blue Golf Course and adjoining Wailea Tennis Club, this property is ideal to rest from everything Maui has to offer for your discovery. Within minutes of both driving and walking,...
Waikoloa Beach retreat! Top floor, walk to beach+shopping+golf, saltwater pool
Welcome to our happy place, Vista Waikoloa D301! Centrally located in Waikoloa Beach Resort on the Big Island, your condo features:- Spacious 350 sq ft. wrap-around lanai (with peek-a-boo views of Anaeho'omalu Bay)- Gorgeous views of Mauna Loa and Hualalai- Walk to...
The Most Gorgeous OV Villa in Kapalua Sleeps 6
THE BEST LOCATION ON MAUI, ALSO, THE BEST LOCATION IN THE COMPLEX!!! THIS IS PARADISE!!! Enjoy beautiful ocean and sunset views. I was just there and from my lanai, we watched whales breaching. You will love our great views of the ocean, golf course and the island of...
Updated oceanfront gem @ Sugar Beach Resort, Central AC, NO Booking fees!n
Welcome to Sugar Beach 518. This updated oceanfront 1 bedroom, 1 bathroom condo can accommodate 4 people. Enjoy ocean views throughout this unit and from your private lanai. Feel right at home with everything from central AC to in unit washer/dryer, and essentials....
Aloha Hale - 3-bedroom house in tropical Pāhoa near Hilo
Your group will be close to everything when you stay at this centrally-located home near Pahoa Town where you'll find local shops, a variety of restaurants, and the gateway to exploring the Puna District. The 3 bedroom 2 bath home is located in a quiet Hawaiian...
Great Rates! Intimate Ocean/Beach Condo, Couple's Paradise!
new flooring, walk in shower, new vanity, new kitchen cabinets countertops, appliances,fresh paint quiet concrete building with high ceilingslarge 1 bedroom unit 799 sq ftmeticulous grounds with lots of Hawaiian plantsbbq pool hot tuba true sliver of paradise!
Modern Spacious Beachfront Luxury in Wailea. Family Friendly!
A modern 2 bedroom, 2 bath condo with extra bunk beds and an amazing ocean view!South Maui is one of the most beautiful destinations in all of Maui and Wailea Ekahi Village is a perfectly situated, beachside resort we call home. Guests return to Ekahi year after year to...
Convenience & Comfort, A minute walk to Hanalei bay and short stroll to town!
Note: Our transient vacation home is located in a Tsunami Evacuation Zone. In an event of a Tidal Wave, evacuate to higher grounds. We also incur occasional bridge closer due to flooding of Hanalei roads. Access to our vacation home may be limited to all local traffic....
#605 Top Floor Unobstructed Ocean View/Sunsets, New quiet A.C.
Island Surf #605 Condo Description:JUNE UPDATE: New central AC was just installed ! Incredibly quiet !! Individual room climate control. Aloha! We are excited to share our condo with you for your beautiful trip to Maui and we would like to make your vacation as...
❤️PiH❤️FLORA PARADISE★Closest to Pools Fitness★ PLUS Hilton Resort Passes★3 Full Baths★Private Beach Club
Brought to you by Paradise in Hawaii Luxury HomesWelcome to Flora Paradise Villa, a part of our Hawaiian Luxury Collection. Flora Paradise Villa at KaMilo is a gorgeous 3 bedroom, 3 bathroom home, with two master suites. This beautiful home has been professionally...
Partial Ocean View King Condo at Maui Vista Kihei
Aloha! Enjoy our newly refurbished 600sqft condo located at the heart of Kihei with only 3min walk to the beachFeatures:• New king bed with 14inch hotel style mattress • Queen sofa sleeper• Two smart TVs• 1 window AC, 1 new portable AC• In-unit wash & dryer•...
Beautiful Hawai’i Big Island Luxury Vacation Villa in Kailua Kona
Our gorgeous Big Island Hawai'i Hale Ali'i villa is resort living in the setting of a private home. Enjoy island living at its best! Perfectly situated in the Ali’i Heights area in Kailua Kona, the villa is just 10 minutes away from Kona Town with all the conveniences...
Maui Resort Rentals: Hyatt Residence Club – 2BR Oceanfront Upper Floor VIlla
Exquisite 2 Bedroom Residence With Jaw-Dropping Oceanfront Views at Kaanapali's Newest, Most Exclusive Resort!Proudly perched upon Ka'anapali, one of the world's most beautiful beaches, is the Hyatt Residence Club Ka'anapali. Within the lush borders of this sprawling...
Charming Hanalei Beach Cottage Walk to town & the Beach! A/C TVNC-1091
Mana Kauai Island Vacations presents the charming Palaka Cottage! Recapturing bygone days, the completely renovated 2 bedroom 1 bath "Palaka" Vacation Cottage draws one back to the days of the sugar industry's plantation cottages. With immense old world Hawaiian charm...
Ideal Family Retreat! - Beach Pass Included - Great Location - Beautiful Sunsets
Fairways at Mauna Lani 1001 -- One of the best locations within the complex -- INCLUDES COMPLIMENTARY ACCESS to the parking at the Beach Club (calm water beach with a great snorkeling and restaurant: 5 minutes driving from us) -- Renovated with attention to details in...
Na Hale Keauhou M5: Your Coastal Villa Awaits
Welcome to the Seaswept Mermaid Villa, a stunning ocean-view condo located in the beautiful Keauhou area of Kailua Kona. This inviting two-bedroom, two-bathroom retreat is perfect for families or groups of up to six guests, offering a serene ambiance that captures the...
3 Bed Oceanfront Penthouse
Welcome to your oceanfront Maui basecamp, Papakea B406! This three bedroom, two bath penthouse unit welcomes you with breathtaking ocean views, the sound of crashing waves, and is conveniently located within walking distance to beaches, markets, the ABC store,...
Papakea Resort K301 - Ocean View & Free Parking!
Aloha from Midway Vacations! Our team of local hospitality experts is dedicated to turning your Hawaiian getaway into a reality. When you stay at one of our properties, you can count on a professionally cleaned and meticulously maintained experience. We're even...
Ocean View Cabin located on Organic Coffee Farm with Hiking Trails
This is a beautiful jewel of a house. It's all one level and close to shopping, activities such as hiking, biking, zip lines, farm tours, horseback riding, art school, dining and Haleakala National Park. Just an eight to ten minute drive to white sand beaches.This...
2 Bedroom/2 Bath Luxury Oceanfront Resort Vistas
Summary:Fully remodeled and professionally decorated in April 2023 with all new furnishings. This elegant 2-bedroom, 2-bath condo features luxurious touches paired with oceanfront serenity. Located in sunny Kihei at Menehune Shores resort, all of Maui is within reach....
2 Bedroom 2 Bath Condo- Maui.
Enjoy one week of elegant luxury in my two bedroom unit right across from Kahana Beach. Check-in days are Wednesdays, Fridays and Saturdays. Amenities include pool, tennis courts, and air conditioning. Test the waters of nearby beaches famed for swimming, body surfing...
Spacious 1 Bedroom Ground Floor Condominium in Kailua-Kona
#135 Casa De Emdeko is amazing. The condo is 920 square feet, on the ground floor 30 feet from the sand and less than 30 yards from the ocean. .
Exceptional 5-stars Beach Villas at Ko Olina - 3 Bedrooms & 3 Full Bathrooms
2nd most reviews on VRBO!!! See other unit we have available: VRBO #950616The Resort: Beach Villas at Ko Olina.The Beach Villa is located at Ko Olina, Hawaiian for Place of Joy. Ko Olina is a picturesque resort located on Oahu's western side nestled away from the hustle...
Luxury king suite with A/C, Walk to Beaches & 1 Hotel Resort, Massage Chair
As an experienced traveler and VRBO guest myself I've come to appreciate how important it is to find a place to stay that is furnished with a top quality bed and bedding, a great shower experience, laundry facilities, sharp knives and surprise amenities.I've designed my...
2-bedroom condo in charming Kailua-Kona with AC, WiFi. Enjoy your stay
Welcome to Kona! We're thrilled to have you stay in our spacious, townhouse-style condo.As you'll discover, the location is truly unbeatable. You're just steps from the ocean and a short walk to the heart of Kona. Plus, the condo boasts amazing ocean views from both...
EL L202 Updated Kaanapali Condo Beachfront Cabana
Eldorado L202 Charming Maui Getaway at Updated 1Bedroom Condo at Maui Eldorado Resort in Kaanapali! Facilities include Pool, Hot Tub, Fitness Room and Beachfront Cabana FREE daily activities included with your stay value up to $570! Complimentary admission, every day of...
Maui Resort Rentals: Honua Kai Konea 337 - Large Luxurious Studio w/ Lush Courtyard and Peek-a-boo Ocean Views!
This luxurious corner studio condo sits directly above the beautiful courtyard of Honua Kai and offers peek-a-boo ocean views through the lush tropical foliage. When you walk out onto the lanai, you'll marvel at all the beautiful flowers, trees, and koi ponds all around...
Oceanfront Ground floor Corner Unit 2bd/2ba n#1 Location
Recently updated condo, this is the closest unit to the beach and pool with NOTHING between you and the beach. Located on the ocean side of the building in the ground floor corner unit, only steps to the beach or pool. The sunsets are incredible here. This is a great...
Welcome to your Maui Escape!
Experience the ultimate getaway at a charming and centrally located condo in Kihei, just steps from the beach! Nestled in a small quiet complex, this tropical retreat offers a peek-a-boo ocean view, the perfect backdrop for your morning coffee or evening sunset. Enjoy...
Kaunakakai Condo w/ Private Lanai & Ocean Views!
Spend your next memorable Hawaii getaway in your own personal paradise when you book this Kaunakakai vacation rental on Molokai! Located in the Wavecrest Resort, this 1-bedroom, 1-bath condo offers convenient access to a number of on-site amenities, including oceanfront...
Surfer's Paradise - Beachfront Vacation Rental on Oahu's North Shore
Welcome to Surfer’s Paradise by Gather, a newly remodeled, legal nightly beachfront rental on the North Shore of Oahu. With its clean, spacious, and uncluttered space, Surfer’s Paradise is the perfect place to enjoy every second of your vacation.Please note that the...
Island-style decor, oceanfront & sunset views
Noelani 203 is a 1-bedroom, 1-bathroom condo on the 2nd floor featuring amenities such as panoramic ocean views, a remodeled kitchen, and a washer/dryer in the condo. The condo can accommodate up to 4 guests with a King-size bed in the bedroom and a queen sleeper sofa...
Paradise at Bay View Farms w/ Private Infinity Pool, Hot Tub & Incredible Views
Bay View Farms Estate HouseOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Retreat to a gentler, slower-paced era in this beautifully decorated “Estate Home”, offering 6400 sq....
2 Bed Maui Retreat with 5 miles of beach!
Kanai A Nalu, what a gorgeous beach front condo! It's a great remodel with tile flooring throughout, island-style furniture, and a stunning kitchen with a full-size front load W/D! All the comforts and conveniences of home, but it's in paradise! With 2 bedrooms, one...
Immersed in nature Home w/ A/C, bbq area, Hale Poola
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.This five-bedroom, three-bathroom home sits in...
Modern Luxury Remodel - Maui Kamaole J114
Boasting ocean and West Maui Mountain views from the lanai, a modern chef’s kitchen, a resort-style en-suite bathroom with a Calcutta Laza Quartz double vanity, and a King size bed featuring a Sealy Tempurpedic cooling memory foam mattress, this is the luxury rental...
Hale Lo'i House: Luxury + comfort in sunny Poipu!
This bright, spacious, brand-new 4-bedroom, 3.5-bath house has everything you could possibly need for a flawless vacation—and luxurious perks galore. Located in a quiet, upscale neighborhood, this charming tropical hideaway is close to some of Kauai’s best beaches,...
Malaekahana Ocean Front Cottage (30 day min)
Beautiful and charming describes this tranquil and peaceful ocean front cottage.It sits on the 1st level, beach front, of a private estate home on over 3/4 acres of manicured lawn to the ocean. A view from every room!Fall asleep to the sound the ocean waves and wake to...
Probably The Most Peaceful & Beautiful of North Shore Estate
Greetings! Welcome to the - HaleAlohaEstate - on Oahu's North Shore. Come experience a truly authentic Hawaiian experience in our beautiful Estate home with 6+ bedrooms, and 4.5 bathrooms on the quiet – best part of Oahu’s famous North Shore. Enjoy the 5-acre...
Luxury condo with central A/C and golf and ocean views
Come and discover our beautiful new condo on the 9th fairway of the Kiahuna Golf course. Our brand new condo is set in the perfect location to see both distant ocean views and distant mountain views. We have a beautiful lanai where you can catch the sun setting and...
Luxury Villa Steps to Ocean w/ 3+ Bedroom Sleeps 8
This gorgeous ocean view Luxury Estate is in a gated community right on the 5th hole of Mauna Lani Resort South Course with breathtaking views of fairways, ocean and mountains. Experience the exclusive lifestyle just minutes away from the beach - with 3,600 square feet...
Ulua Beach Premier 2-Bedroom Oceanfront Unit...Unobstructed Ocean Views!
Welcome to Wailea Elua #1904! This recently renovated luxury beachfront 2 bedroom/2 bath residence is in the heart of Wailea on Maui’s Sunny South Shore. Within steps of the unit is Ulua Beach, one of Maui’s best! Ulua Beach is ideal for family fun, snorkeling,...
Hula House - Beachfront North Shore Oahu
REMAINDER OF 2025 SPECIALS!BASE RENT REDUCTIONS FOR OCTOBER AND NOVEMBER FROM $15240 TO $14000DECEMBER FROM $21000 TO $19000.This spacious modern ocean front homes is beachfront luxury on the north shore. Unobstructed views of the ocean welcome the guests from both...
Beachfront Escape at Royal Mauian #207 – Unmatched Ocean Views and Comfort!
Experience the ultimate Maui vacation at Royal Mauian #207, a stunning two-bedroom condo offering breathtaking ocean and coastline views. Located in the unique six-story Royal Mauian property in South Kihei, this oceanfront retreat provides unobstructed views of the...
Impressive Wailea Ekahi 1 Bd+2Ba Condominium 20G-Adjacent to Keawakapu Beach
Don't miss the best that Wailea Ekahi has to offer. Ekahi 20G - newly remodeled as of August 2025. Gorgeous! Professional new media pending. Stay with Wailea Rentals at Wailea Ekahi Village 20G and you and your guests will enjoy premier accommodations, furnishings and...
99 steps to quiet beach - Centrally located - Great for families & groups
Ideally located on iconic Alii Drive directly where the world famous Iron Man takes place annually. A number of palm trees and local landscaping on the front and side of the property add to the tropical appeal.Nearby are many of Kona's enviable attractions including its...
Breathtaking Part. Ocean View in Kauai!
The Point at Poipu is a dream vacation destination on the southernmost tip of Kauai. The resort overlooks the sands of Shipwreck Beach & is secluded among lush landscapes. After a day of exploring, return to the resort to relax in the spacious two-bedroom accommodations...
JJs Hāna Hale - Farm House
Aloha!Welcome to Beautiful Hana! JJ’s Hana Hale is a air conditioned 1 bedroom cottage, conveniently located near idyllic Hana town near the tiny Hana Airport in a historic district Hawaiian’s call: Ka’eleku, we’re on 6 verdant acres (turn left near the 31 mile...