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.
Panoramic Ocean Views With Private Saltwater Pool
E Koma Mai (Welcome) to this upscale retreat that offers you a true luxury experience. Sitting on a hillside, this home boasts unobstructed views of the coastline from the main pool deck, upper lanai, and from nearly all interior spaces. With 3 bedrooms and space for 6...
Hale Pakika at Kukui'ula: Exclusive 5BR Estate Private Pool, Golf & Ocean Vistas
Welcome to Hale Pakika at Kukui’ula by Gather, a five-bedroom, five-and-a-half-bathroom hideaway designed for up to twelve guests. Located off the first tee of the Kukui‘ula Golf Course in Koloa, this 3,500-square-foot single-level estate blends barefoot luxury with the...
Fully Renovated 1BR/1BA condo w/AC. Short walk to beach & Coconut Marketplace!
Welcome to your slice of paradise on Kauai’s beautiful Coconut Coast. This newly renovated 1-bedroom, 1-bathroom corner unit at Plantation Hale Suites is located on the ground floor for easy access and offers the perfect blend of comfort, convenience, and island...
Iconic Diamond Head and Ocean View in Waikiki!
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...
Island Glow Kailua Village, AC and ocean views in the heart of Kailua Kona
See whales, dolphins, Ironman Village and Ali’i drive from your very own lanai! Island Glow in Kailua Village is a beautifully remodeled 1 bed 1 bath condo with a brand new king bed and queen pullout sofa bed in the heart of historic Kailua Village. You will enjoy ocean...
Oceanfront tranquil views with refined finishes
Welcome to Mahana 806, your 1-bedroom, 1-bathroom getaway that offers central AC, ocean views, and an in-unit washer/dryer. Unit 806 can accommodate 2 guests. The bedroom features a king-size bed strategically placed to offer ocean views and direct access to the lanai....
Wai'ula'ula Villa 330 Three Bedroom
This discerning, upcountry, oceanview residence offers a great room with sliding glass pocket doors that invite indoor/outdoor island living; a chefs' kitchen outfitted with slab granite countertops and premium stainless steel appliances (including a wine refrigerator);...
2/2 Oceanview Modern Resort Vistas
Summary:Spacious and elegant. Completely remodeled in March 2024, no expense was spared to create our gorgeous oceanfront oasis. This two-bedroom, two-bathroom condo features luxurious touches paired with oceanfront serenity. Located in sunny Kihei, all of Maui is...
Kauhale Makai 131 OceanFront Ground Floor 1BD w Pool AC Beach
Kauhale Makai 131 Island Style Updated 1Bedroom OceanFront Condo. Ground Floor for Easy Year-Round Indoor-Outdoor Living. Tropical Getaway to Relax and Recharge Aloha and welcome to our charming Maui getaway nestled on the ground floor of the Kauhale Makai Resort in...
Stunning ocean view 2 bedroom • Steps from beach
Enjoy beautiful ocean & sunset views from, Ohana Lani, a 5th floor condo with 1120 sq of living space and a stunning double wide lanai. The condo artfully blends modern amenities and island style. Ideally located in Kihei, the unit is right across the street from the...
Kaanapali Alii Residence 373
Kaanapali Alii 3732 Bedrooms | 2 Bathrooms | Sleeps 6 | Ocean View________________________________________Kaanapali Alii 373 is a luxurious ocean view vacation rental located in the heart of Maui's renowned Kaanapali Beach. This spacious condo over 1,700 square feet...
Kaanapali Alii Residence 155
Kaanapali Alii 1552 Bedrooms | 2 Bathrooms | Sleeps 6 | Ocean Front________________________________________Welcome to Kaanapali Alii 155, a two-bedroom oceanfront condo overlooking one of the top-rated beaches in the world year after year! Nestled along the pristine...
Kamaole Sands 4-411 - Stunning Modern Renovation, Enclosed Loft, 3 Zone Split-AC
Discover the ultimate getaway at Kamaole Sands 4-411, a stunning ocean-view condo nestled in the heart of South Kihei, Maui. This luxurious 2-bedroom, 2-bathroom retreat offers a perfect blend of comfort and style, accommodating up to 6 guests, making it ideal for...
POIPU RESORT, sand POOL, daily fresh towel exchanges, turtles, cascading ponds
ALOHA! This 2 bedroom, 2 bathroom condo is located in the beautiful resort called "The Point at Poipu", a family friendly resort.Gorgeous 2 BEDROOM, 2 BATHROOM (King in master and 2 Twins or we can request a Queen for the 2nd bedroom), OCEANFRONT RESORT, short walk to...
PARADISE RV .You won't forget your time in this romantic, memorable place.
Experience the magic of Maui on your terms! Our camper vans provide you the freedom to explore hidden beaches, wake up to sunrise on Haleakala. Tailor your Hawaiian adventure. Enjoy Maui beautiful!!!!
Maui El Dorado Kaanapali Beach Studio- G204, Maui El Dorado Kaanapali Beach Resort
New Property!!Located within the Maui El Dorado, this condo is surrounded by palm trees with a peek-a-boo view of the ocean. This is a 10-minute walk from the Whalers Village and restaurants and 1 mile from Black Rock Beach. There's a 3-night minimum stay.The complex is...
Waikoloa Beach Villas P2nLuxurious Paradise
Luxurious tropical island vibe. Relax and take in all Hawaii has to offer with fully furnished condo in walking distance to shops, restaurants, beaches and entertainment. The Space: Highly desirable location for both privacy and walking distance to many attractions....
Hawaii Eco Village in Hilo AIR
Welcome to the Hawaiian Wildlife Habitat Eco Village, which is part of the responsible tourism effort to take care of the Aina (Mother Nature in Hawaiian). We offer an individual detached self contained bedroom (hexagon) with full bathroom and a kitchenette. To start...
3-Min Walk to Beach! Ground Floor - No Resort Fee
Just a 3-minute walk from the beach-cross the street and you're there from this first floor condo! Minutes drive to coveted Wailea beach and the area's best sunset views, shopping, and restaurants.★ No resort fee★ Private bedroom and bathroom★ Three beds★ Two full...
Beautiful Stylish Condo W/ Amazing Ocean Views, Walk To World Class Beach!
***Professionally Cleaned Condo, No-Contact Check-In/Check Out***Welcome to Kamaole Beach Royale #310, located in the heart of Kihei, Maui!. Enjoy a spectacular views of the ocean, beaches and neighboring islands in this recently remodeled condo!This condo has just been...
WBH D225 Aloha Ola2 – Relax in Oceanfront Paradise
Summary:This family-friendly beachfront, second floor 1-bedroom/1-bath air-conditioned Condo Suite comes with a comfortable king-size bed and living room couch that pulls out to a queen size sofa-sleeper allowing the unit to sleep up to 4 people. Just steps from the...
WBH D225 Aloha Ola – Ocean and Pool View
Summary:This family-friendly beachfront, second floor 1-bedroom/1-bath air-conditioned Condo Suite comes with a comfortable king-size bed and living room couch that pulls out to a queen size sofa-sleeper allowing the unit to sleep up to 4 people. Just steps from the...
Spacious Modern 2Bdrm Condo, Free Parking in Bldg., Full Kitchen, Sleeps 6.
Renovations were completed in March 2024. Everything is new. 6 can sleep comfortably, 7 when 1 or more are children.This condo is tastefully decorated and features a spacious living room with a comfortable sofa that opens to a full-sized bed, and a flat-screen TV. The...
Great Location! Walk to Everything in South Kihei!
If you want to be close to it all - best beaches, best snorkeling, only surf spot in Kihei, SUP, kayaking, snorkel tours, dinner cruises, shopping, restaurants, nightlife - our recently updated, owner-managed (no dealing with unresponsive property managers) condo is the...
Sky Villa Estate Luxury Gated Retreat with Amazing Ocean Viewn
Welcome to your Hawaiian haven, Sky Villa Estate! Kick off your flip-flops and let alohaspirit guide you up the driveway to this secluded gated 5-acre estate, through lushlandscape that feels like a warm hug from the island itself. Deep lush lawns encouragefamily games...
Hale Mele 2 Panoramic Golf Course Views, Pool/Hot Tub, Golf Cart & E-bikes
Welcome to Hale Mele 2 — A Private Island Retreat of Elegance and ComfortDiscover the ultimate Hawaiian escape at Hale Mele 2, an elegant 5,100-square-foot, two-story luxury residence nestled within the prestigious Champion Ridge gated community on the Big Island’s...
Upscale Kona Retreat, Ocean Views, Private Pool, BBQ, AC's
Welcome to paradise in Kailua-Kona, Hawaii! 🌴 Escape to this stunning 3-bedroom, 2-bathroom oasis boasting breathtaking ocean views and a private pool for the ultimate Hawaiian getaway. Wake up to the panoramic views of the Pacific Ocean right from your private lanai,...
Princeville Luxury Townhouse, modern with A/C.
Welcome to Villas on the Prince #28 a modern Princeville 3 bedroom, 3 bathroom condo situated in a private gated community that has AIR CONDITIONING in all bedrooms and main living areas. Recently updated. Sleeps up to 6 guests comfortably and within walking distance of...
Peaceful Big Island Homebase with Coastline Viewsn
Experience Big Island aloha from your fully outfitted vacation rental house in Kaʻū, Hawaiʻi Island's southernmost district.• Punaluʻu Beach (black sand, 14 mi)• Ka Lae (South Point, 12 mi)• Hawaiʻi Volcanoes National Park (40 mi)Recharge back at your comfy 2-bed/1-bath...
Heart of Princeville w/AC minutes from everything!
Escape to our North Shore Kauai retreat in Princeville! A haven of beauty awaits you, with leisurely walks along Makai Golf Course offering breathtaking mountain and waterfall views. Experience mesmerizing sunrises, stunning sunsets, and starry nights in the tranquil...
Luxe Oceanview 2B2B Escape w/AC Near Beach & Shops
Summary:Location and Quality! You will feel the relaxed beach vibes from the very first step walking into this tastefully updated & beach luxe unit. Directly sit across the famous Cove surf spot & in the middle of all, you will be memorized by the ocean waves along with...
Modern Waikiki Beach Oasis w/ free parking
Aloha! This 550 sq ft 11th floor 1 bedroom in Waikiki Banyan is a relaxed, contemporary space designed to create special memories in a stylish, comfortable environment. With a city and mountain view from the lanai, this fully updated, air conditioned property is just...
Pono Pearl Villas | Beach Access + AC In Every Room
Just a short walk from the beach, this spacious home is ideal for family reunions, retreats, or groups looking for space, privacy, and easy shoreline access. This listing represents one of several similarly appointed homes in the Windward area. All units share the same...
Hale Mahina A406
Welcome to Hale Mahina A406, aka The Fish Condo. This top floor oceanfront 2 bedroom, 2 bath condo boasts stunning views from your private lanai, living room, & even the kitchen. With your Maui memories in mind this condo has everything needed to feel right at home....
Stunning Ko Olina 2BR Beach Villa O414 w/ Golf Course, Mountain & Ocean Views
Welcome to Ko Olina Beach Villas O414, a beautifully positioned 4th-floor corner villa offering a refined blend of comfort, island elegance, and effortless resort living. Overlooking the Ko Olina Golf Course with framed mountain vistas and a peek of the ocean, this...
Luxury Ko Olina Oceanfront Villa O1105 w/ Stunning Ocean Views near Golf Course
Welcome to the luxurious beachfront retreat of Ko Olina Beach Villas O1105, a spacious 3-bedroom villa set within the exclusive Ko Olina Resort in Kapolei. Sweeping ocean views, an open-concept layout, and direct access to lagoon pathways create an effortless blend of...
Luxury Ko Olina Beach Villa B109 by Gather w/ Stunning Ocean & Kapolei Views
Ko Olina Beach Villas B109 is a ground-level oceanfront retreat in Kapolei's Ko Olina Resort. With two bedrooms, two baths, and sleeping space for six, this villa blends comfort, luxury, and direct access to the lagoons, making it the perfect escape for families,...
Rainforest Volcano Retreat – As Seen on TV! Near Volcanoes Nat’l Parkn
Volcano Rainforest Retreat — As Seen on “Building Off the Grid”!To see our home featured on TV:Search online for Building Off the Grid — Season 7, Episode 5: “Volcano Home”Welcome to Volcano Home, a handcrafted 2-bedroom, 2-bath rainforest retreat on the lush slopes of...
Ground Floor Luxury Penthouse at The Villas | F100
Summary:F100 | TA-018-220-0320-02Wake up in paradise at Villa F100, part of the exclusive Villas at Poipu Kai. Enjoy tranquil garden views from your private lanai, cook gourmet meals in the fully stocked kitchen, and dine al fresco under tropical skies. Relax by the...
Maui Resort Rentals: Kaanapali Ali'i – Oceanfront Ground Floor + Yard Area, 4 Total Bedrooms+DEN, Sleeps 14
This one-of-a-kind oceanfront 4BR plus den ground-floor offering at the acclaimed Kaanapali Alii in the heart of Kaanapali Beach consists of two luxurious adjacent suites. Together they offer a massive 5,188 sq ft of combined interior living area and a sleeping capacity...
Entire House! Peaceful retreat 4BR Waikoloa beach
About this spaceWelcome to our exquisite residence in Ainamalu, the "Peaceful Land" of Hawaii.1. Surrounded by majestic mountains and the ocean, our home offers a serene and captivating backdrop.2. Accommodates up to eight guests, perfect for families or groups of...
Luxury Oceanview Wailea Point 3-Bed Suite
Discover luxury living at Wailea Point Resort, nestled between prestigious resorts, this oceanfront paradise promises the ultimate South Maui experience. Our 3-bed luxury condo offers four bathrooms, in-suite laundry, two workspaces, and a chef's kitchen with top-tier...
G302: Remodeled Maui Condo with Ocean and Sunset Views, Updated Kitchen & Baths
Beautifully remodeled home at one of Maui’s favorite properties! G302 is one of a handful of condos on property with a fantastic ocean and sunset view as well as views of Haleakala all from your own lanai. The kitchen and both baths have been fully updated. New vinyl...
Beautiful Ocean View Remodel - Luana Kai B306
This two bedroom, two-bathroom, top floor condo at Luana Kai sleeps 6 with a sofa bed in the living room. The kitchen has been beautifully remodeled with top of the line appliances and features stunning hand-crafted wood details like a split mango wood counter, custom...
25% OFF • 2 Oceanfront Villas in One • 3BR+Studio • Steps to Beach • Pool & Tub
New Year’s Special: 25% OFF Your StayValid for stays January–March 2026. Book now!This villa is a unique combination of our existing two villas; our 3-bedroom (VRBO 3722129) and our one-bedroom (VRBO 3722906) villas. These two units are separated by adjoining doors....
PARADISE OCEAN VIEWS & GOLF w/ A/C + Pool / PickleBall / Tennis
E Komo Mai - Welcome to our Hawaiian Sanctuary (otherwise known as our Hawaiian Happy Place) offering nearly 180-degree Ocean View over Waikoloa Village Golf Course, with golf (at reduced rates plus a range/putting green), free tennis and pickleball (under lights), and...
25% OFF Romantic Honeymoon 1BR Villa Steps to the Beach, Private & Serene
New Year’s Special: 25% OFF Your StayValid for stays January–March 2026. Book now!This is a newly owned One-bedroom studio villa. Designed with Romance and Island flare in mind for lovers.Enjoy Oahu's magnificent North Shore from a luxury one-bedroom, privately-owned...
25% OFF Oceanfront Turtle Bay 3BR Villa with Pool & Tub – Steps to the Beach
New Year’s Special: 25% OFF Your StayValid for stays January–March 2026. Book now!Indulge in North Shore Luxury – Closest 3BR Villa to the Beach at Turtle BayWelcome to your ultimate Oahu escape — the only single-story 3-bedroom villa at Turtle Bay Resort, and the...
2 Mins to Private Beach, Dolphin Whale Watching, H6A
Escape to a serene slice of the Big Island at Dolphin Bay Estate - a spacious, tropical retreat in Captain Cook with self check-in and a secluded beach just a short stroll away. Perfect for families and friend groups who want privacy, ocean air, and easy access to...
Villa Sea Renity Remodeled Family Friendly Tennis
Experience the relaxing setting of this 1BR 1.5Bath condo in the lavish gated community just a stone's throw away from beaches, shops, restaurants, and attractions of Hawaii's Big Island. Take in the area's scenic beauty and diverse selection of water activities. After...