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.
Laule'a 'Ohana Hale - Luxurious 'Ohana home with A/C
Laule'a 'Ohana HaleBrand New! New vacation rental now offered through Makana Kauai PropertiesWelcome to Laule'a 'Ohana Hale, Princeville, a luxurious and wonderful vacation rental home on Kaua'i! This home boasts impressive panoramic mountain views from the main living...
Hale Ka Nani stunning ocean and mountain views, 1 bdrm/1 bath kitchen & laundry
Minimum 31 day stay required. Hale Ka Nani, which means “beautiful house” in Hawaiian, is situated on 3.3 acres in the private, gated community of Kohala Ranch on the beautiful Kohala "Gold" coast. Kohala Ranch is a large 4,000 acre secure/gated “working” ranch,...
Waikīkī Shore 404 - Studio Waikīkī Beach View
Castle Waikīkī Shore Unit 404 offers all the comforts of home on your Hawaii vacation: a fully equipped kitchen, air conditioning, WiFi, mounted flat screen television, washer/dryer, and private lanai. The unit is tastefully furnished with beautiful koa wood furniture...
Oceanside-Spectacular View and Poolside Oasis!
Summary:With a sprawling ocean view, this little island oasis is the epitome of the dream vacation home. Wood beam ceilings and rich grainy finishes contribute to the "island beach house" character. Poly Shores is minutes from world famous Kaanapali beach and Kaapalua...
First-floor condo across from Magic Sands with balcony, pool & sauna
White Sands Resort #108Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'The soft, white sand of Magic Sands Beach Park is right across the road from this completely remodeled...
OPEN! REDUCED RATES FOR MAY!! nHonua Kai Ground Floor LUXURY
BOOK NOW ! REDUCED RATES10/7-10/31-$950 PER NIGHT!!!9/1-9/14 & 9/20-9/26-$650. PER NIGHT!!!8/5-8/31 $750. PER NIGHT!!!This is ground floor unit Konea 102 at Honua Kai. Currently, new bookings in my units through VRBO come with my book in confidence COVID guarantee. My...
Hawaiian Charm..Just Steps From The Ocean..On Kauai's Sunny W Side * TVNC4216
PROPERTY OVERVIEW: House, 2 Bedrooms, 1.25 Baths, (Sleeps 4)The Nene Nest, Kauai is a classic, sugar plantation- style cottage located on the always sunny West Side of Kauai. Just 152 steps from the ocean, it offers a true Hawaii feel. Designed with a 'slow' pace in...
Maui Eldorado ~ J-106 ~ Walk-Out Ocean Views
This is a legally permitted vacation rental and hotel zone according to the County of Maui ordinances. Breathtaking Ocean Views, Spacious Lanai, and Exclusive Beach Cabana at Maui EldoradoE Kō Mo Mai (Welcome) to your perfect Hawaiian retreat at Maui Eldorado, where...
Wailea Ekahi 40A - 5-Star South Maui Oasis
Welcome to your piece of paradise in a completely remodeled, fully furnished, ground floor unit! Our home is located in Wailea Ekahi, one of the few Kihei and Wailea properties located directly on the beach; no need to cross a road or even sidewalk!Our private corner...
The Wave at Kapalua, Ocean10th Hole Golf Course Views NEW Full Remodel late 2022
3 years in the making completely remodeled top to bottom, new everything as of Aug 2022, "The Wave At Kapalua" is your perfect Maui vacation condo with an ocean view! Designed with an elegant tropical whimsey, bright, and colorful, with accents and attention to detail...
Maui Resort Rentals: Hilton Maui Bay Villas - Brand New 2BR Penthouse Oceanview Suite!
Nestled among 27 acres of lush tropical gardens, the Hilton Maui Bay Villas is a luxurious, secluded resort located on South Maui's sun-drenched coast. Situated minutes from several upscale resorts, pristine beaches, and championship golf courses, guests will enjoy...
Pili Mai 11K: Luxury Condo w/ Community Pool, Hot Tub, AC & Ocean/Golf Views
Welcome to Pili Mai, the modern and stylish abode that is sure to fill your next Hawaiian vacation with comfort and relaxation. Situated on the scenic Kiahuna Golf Course on the south side of Kauai with picturesque panoramic mountain views and the ocean just beyond,...
1 Mile to Magic Sands Beach: Kailua-Kona Cottage
Beach Equipment | Natural Lighting | Quiet Neighborhood | 5 Mi to Downtown KonaClear the calendar and say 'Aloha' to your next tropical getaway at this 1-bedroom, 1-bath vacation rental cottage in Kailua-Kona. Perched on the west coast of the Big Island, this quaint...
Oceanfront at Sugar Beach Resort - #226
Our ocean front condo has unobstructed views of the ocean with the islands of Kahoolawe and Molokini in the distance. SBR#226 is in the middle of the second floor of Plantation Building at Sugar Beach. The Resort has large, free, off-street parking areas with easy...
Valley Isle Resort #105 - Oceanfront Condominium
Free Wi-fi, Free Parking, No Resort Fees**Brand New Split AC System installed**Valley Isle Resort #105 is a charming ground floor 1-bedroom unit situated along Maui's picturesque western coastline. This cozy retreat features a queen bed in the bedroom and a convenient...
❤️PiH❤️ SEA GLASS★ Best Views ★ Private Heated Pool★
Brought to you by Paradise in Hawaii Luxury Homes.Welcome to Sea Glass House, a part of our Hawaiian Luxury Collection.Sea Glass House at KaMilo is the pinnacle of luxury at KaMilo and was built on the best lot in KaMilo for privacy and views.It is surrounded by...
Hale Kipa Ohana
Experience our Beautiful town of Waimea in this 3-bedroom 2 bath home on a one acre parcel. This home gives you the Country tranquil setting of the Kohala mountains surrounded by the lush green outdoors. A great yard to play volleyball and any outdoor sports. A play...
Kauai Beach Resort~Beautiful Mountain View
**Please read 'Other Things to Note' in listing** Capture the tranquility and beauty of the Garden Isle from this charming, centrally located condotel unit at the Kauai Beach Resort. From your private lanai, take in Kauai's lush landscape and majestic mountain views,...
Exceptionally Pristine Haleiwa North Shore Beachside Retreat
Summertime on Oahu's North Shore! -AVOID TRAFFIC MESS AT THIS LOCATION-The large Winter surf has gone down and diving, paddling & fishing beckon you just minutes away down a private beach access. Shell collecting, monk seal & green sea turtle watching, sunsets over the...
Poipu Pili Mai 9B, Flexible Cancellation, 4 bdrm, AC, Sunset/ Golf Course View
This is a 3 story building with our 2 story unit located on second and third floors with entry to condo up a flight of stairs. We have four bedrooms, 2 on the second story (the condo's main floor) which are Master suites. While upstairs on the third floor there are two...
Gorgeous Fairway View Home w/Shared Pool, AC & Relaxing Lanai: Kamilo #123
Mauna Lani KaMilo #123 – A brand-new designer home in the heart of Mauna Lani Resort, Kamuela, offering over 2,400 SF of luxury living space. Whether you’re here to relax or entertain, this 4-bedroom, 3.5-bathroom home accommodates up to 10 guests, with ample room...
Exceptional Kona Reef Condo: Full AC, Oceanfront, Easy Walking Distance to Town
*New Listing* Oceanfront, fully updated one-bedroom condo in the Kona Reef Resort. AC throughout the entire unit.Perfectly located just a 5-minute walk from dozens of shops, restaurants, and beaches.As you walk through the door and see the deep blue ocean waves out the...
Alii Cove G3 Beautiful Ground Floor Spacious 2 Bedroom with AC
Alii Cove#G-3 is an excellent beautifully furnished option for your Vacation. This spacious 2 bedroom, 2 bath unit has fantastic features that many guests enjoy. A perfect option for up to 6 people. ~No stairs! Walk right into the unit, there are 2 assigned parking...
Wailea Ekolu Village | 1107
Wailea Ekolu 1107 is a charming ground-floor vacation rental that offers the perfect blend of convenience and stunning views of the ocean, mountains, and the island of Lana'i. Guests can enjoy the soothing sounds of tropical birds without the disturbance of street...
Beautiful, renovated Home. Discover the North Shore of Oahu. Great location.
Aloha!My name is Lindsey and I was born and raised right here in beautiful Laie, HI located on the world famous North Shore of Oahu. This is our personal family home and we will go going on vacation. I love this town so much, that once I got married and started a...
Kona Reef: B-15: Direct Beachfront, Pool/Hot Tub, Air Conditioning, Elevators
Located on the second floor, Kona Reef#B-15 offers stunning year-round views of golden sunsets and easy access to Honl's beach. Hear the crashing of the waves day and night! If what you're searching for is a private seaside apartment that's close, short walking distance...
Wailea Elua Village | 1703
Elua 1703 is a distinctive oceanfront vacation rental, perfectly situated directly in front of the renowned Ulua Beach and the Wailea Beachfront Walking Path. What sets it apart is its unique privacy, surrounded on three sides by lush, meticulously landscaped gardens...
Spacious 2Bedroom/2Bathroom Oceanfront Condo with Central-AC
This spacious end-unit ground floor condo at Royal Kahana Resort is the perfect place to relax and unwind on your Maui vacation. With two bedrooms and two bathrooms, it can comfortably sleep up to six guests. The condo features a fully equipped kitchen, a washer and...
KBM Resorts | FREE CAR | Napili Bay | Oceanfront | Stunning Studio Villa, Turtle views! NAB-107
Charming ground-floor studio just steps from Napili Bay with ocean-view lanai, full kitchen, king bed, and walk-in shower-perfect for couples or solo travelers seeking a peaceful Maui retreat.** Limited Time Special Offer: Reserve any KBM Resorts property in Hawaii with...
Top-Floor Luxury: Rare 3 Lagoon View, 2 Lanais near Disney Aulani, Avail Jun15th
Aug 31st next available. Note: We are the homeowners. Not managed by Vacasa or other troubled rental agencies.Our upscale beach home is ideally located on lagoon two, boasting some of the most spectacular ocean views at our resort from our two ocean facing lanais. The...
Seaside Retreat Condo
Welcome to your retreat by the sea. A great ocean view Overlooking Kahaluu Reef Bay. AC & centrally located in the heart of Kailua-Kona right on Ali'i Drive. Free Digital guide with booking with lots of local recommendations. Designed for comfort and thoughtful details....
"Oceanfront Oasis with Captivating Views: Royal Mauian 317 - Make Memories !
Highly cleaned and sanitized for your vacation. Ask about our AlohaSafeStay program. If you have a stay that qualifies for housekeeping services, traditional housekeeping service will be performed every 7th day. This includes refreshing the condo and exchanging bed...
Steps to Beach Family Friendly in Private Setting Lots of Grass to Play On
Kolea 15G at Waikoloa Beach Resort -- Amazing Location -- 5 minutes walking to the beach -- Heated Infinity Pool with Ocean view -- Contactless Check In & Out -- Fast WiFi -- Our Calendar is always up to date!NEW! We have now another great property at Mauna Lani Resort...
Sunny Side Waves-Beachfront Property-Ground Floor, Corner Unit-Sleeps 5-Remodel
Remodeled ground floor, corner unit in exclusive Bld 11. Steps from Poipu Beach! Only oceanfront condos in Poipu! One of only few air conditioned units (located in bedroom)! New cal-king bed in primary bedroom, queen sleeper sofa & twin in the living room. Sleeps up to...
Relaxing 2bd condo with attractive amenities
Welcome to Maui Vista 3403, your perfect island retreat on the beautiful shores of Maui. This 2-bedroom, 2-bathroom condo is thoughtfully designed to accommodate up to 6 guests, making it an ideal choice for families, couples, or friends traveling together. As you step...
Newly remodeled with AC, gorgeous ground floor condo 87, 3 min walk to beach
Newest addition to our Kiahuna Plantation condos! We just purchased and started renting condo #87. For reviews, please look up our other units - VRBO 1300156, 1587209, and 2160974Dual AC in living room and bedroom.Fully remodeled 1bd/1b condo inside the stunning Kiahuna...
Steps from the Sand ! Stunning Curated Interior Mahana at Kaanapali. Fully AC!
The Mahana at Kaanapali Unit 317, Lahaina, MauiWe are trying to capture the essence of resort living with the cool and casual style of Tommy Bahama's new lines of furniture. Fully stocked gourmet kitchens with brand new appliances, bathroom with dual sinks (a rarity...
122 Hainoa – Designer Oceanview Estate with Pool & Spa at Hualalai
The Hualalai Resort will host the annual Chairman’s Club event from December 1–6, 2025. Please note that access to certain resort amenities may be limited or restricted during this time for residential rental guests. We recommend inquiring prior to booking if your...
Ohana Kamalani: Lavish Fairwayfront Home w/Pool, AC & Stunning Sunsets!
Nestled in the heart of Princeville along the renowned Makai Golf Course, Ohana Kamalani by Gather is a spacious three-bedroom, three-and-a-half-bathroom home designed for comfort and relaxation. With Bali Hai and ocean views, a private pool, and air conditioning...
Luxury beachfront villa on a world class beach in Kailua, HI
As you enter the electric remote gate into this luxurious villa you will feel this sense of peace and calmness come over you.This luxurious Kailua Villa is located on the ocean which is hidden in the best part of Kailua. Wake up every day to the most amazing sunrises...
Great House Across from Beautiful Anini Beach Extended Family 100 steps to sand
At Anini Beach, among many listings on Vrbo, there are only 25 houses for rent, including this, that are actually in the beach neighborhood. It is also permitted by the County as 4217. The North Shore of Kauai has the third largest barrier coral reef in the world,...
Ground-Floor Condo w/Shared Pool, Hot Tub, Free WiFi, and Central AC
Pili Mai 15AOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Ready to experience a new Hawaii? Surrounded by the beautiful Kiahuna Golf Course with views of the mountains and ocean in...
Stunning 3br/2ba, Sleeps 8, Direct Ocean Front, 3rd Floor Condo, A/C, Pool
Welcome to Hale Honu (House of the Sea Turtle)! Panoramic ocean views and beautiful sunsets await you from this spacious 3-bedroom, 2-bathroom ocean front home at the Sands of Kahana. This upgraded beachfront condo is literally steps away from the ocean on the 3rd...
Your Hawaiian Vacation Starts Here! II
Welcome to Kona Shores, a charming complex situated on Alii Drive, along the Hawai‘i Scenic Byway (Ala Loa Foot Trail). Just one mile from downtown Kailua-Kona, this well-maintained ground-floor condo offers easy access to shopping, restaurants, and beautiful...
Ma'alaea Surf, Unit F6 2 BR Beachfront Condo, AC, Wifi, Pool, TV, Kitchen
Ma'alaea Surf, Unit F6 is a townhouse unit situated on the second floor offering guest total privacy. With the latest in contemporary upgrades, this gorgeous unit features a fully furnished modern kitchen and the convenience of a second bedroom and bath. It features...
Rainbow & Bali Hai views, Walk to the Beach, , Sleeps 6, 2 baths, close to shops
Aloha from Surf Sun Rainbow House — Your Relaxed Kauai RetreatEscape to this charming, local-style 3-bedroom condo nestled just off the beaten path in serene Princeville. Designed for comfort, convenience, and that laid-back island feel, our duplex invites you to...
❤️PiH❤️ PARADISE GARDEN HALE ★ Hilton Pool Passes ★ Large Back Yard ★ Enjoy Bikes
Brought to you by Paradise in Hawaii Luxury Homes.Welcome to Paradise Garden Hale, a part of our Hawaiian Luxury Collection. Paradise Garden Hale at KaMilo is a wonderful new single level 3 bedroom home. We pride ourselves on providing some of the most sought after...
Stunning oceanview property minutes from dolphins
Please check out our cottage on the same property for smaller groups: Vrbo 953957 This Unique property showcases a 153 foot ocean facing deck with luxurious indoor/outdoor Hawaiian style living. Everything is completely redone and modernized. You could be swimming in...
Kona Makai Building #1
Stunning ocean views from the lanai, ocean front from the bedroom, the sounds of the surf on the rocks, and the spirit of Aloha welcomes you to our home in Hawaii. Kona Makai is a beautiful oceanfront complex with well maintained gardens, swimming pool, hot tub, gas...
Maui Resort Rentals: Honua Kai Konea 531 - Gorgeous 5th Floor Ocean View Studio
Boasting an ideal vantage point overlooking the Konea Towers lush interior courtyard, this luxurious oceanview studio suite will impress from the moment you enter. From its optimal orientation toward the ocean to its excellent 5th-floor location, your group will enjoy...