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.
Aston Whaler at Kaanapali 1173: 2 Br Ocean View corner Suite on the 11th Fl
The expansive floor plan creates a very spacious two-bedroom, two-bath condo. This well-appointed condo has been completely remodeled with top-of-the-line finishes and furnishings. The lanai wraps around from the mountainside to the center courtyard and offers sweeping...
Kapalua Bay Villa #31B3: 2 BR Ocean View Villa in West Maui
Staying at Kapalua Bay Villa 31B3 offers more than just a luxurious retreat — it immerses you in the very heart of Maui's breathtaking coastline. This beautifully upgraded bi-level, 2-bedroom, 3-bathroom villa combines modern comforts with timeless island charm, framed...
Modern 2bd condo with lush, manicured greens
Welcome to Kihei Resort 227E, a charming 2-bedroom, 2-bathroom retreat nestled in the heart of North Kihei. This delightful unit offers a spacious open-concept layout adorned with modern decor, ensuring a stylish and comfortable stay for up to 6 guests. The fully...
Unit 115 Endless Ocean Views Await!
A LITTLE BIT ABOUT THIS CONDO....Step into paradise at Polynesian Shores 115, where stunning ocean views and island charm create the perfect escape. From the moment you enter, you'll be captivated by the breathtaking scenery—your private lanai overlooks the lush...
Newly-renovated beautiful spacious Condo w/ fabulous mountain & golf course view
Paniolo Greens at Waikoloa C212Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'The tropical haven you've been dreaming of, this newly-renovated, corner unit Waikoloa Village condo...
*IMPRESSIVE Sunset Views and Perfect Location*
Perched on the 5th floor, this beautifully renovated condo offers the perfect Maui retreat; just steps from the golden sands of Kamaole Beach I, and within easy walking distance to dining, shops, and a grocery store. The bedroom features a comfortable king bed and smart...
One-Bedroom Condo with A/C and Fantastic Ocean Views
Our Prince Kuhio 206 condominium is a charming one-bedroom unit that has been recently updated. This vacation retreat features slab granite counters, new kitchen and bath tile, new carpet, new appliances and cookware, and a generous king bed. It is close to everything...
Beach Lover's Haven: Cozy Condo with Ocean Views and 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...
Aloha Condos, Napili Bay Resort, Condo 217, Beach View
Napili Bay Resort condo 217 is a perfect, serene retreat with stunning views and easy beach access. Guests praise the comfortable bed, well-stocked kitchen, and thoughtful extras like beach chairs and welcome baskets. The lanai offers a peaceful, partial ocean view, and...
Island Jewel — Ocean Front North Shore Paradise
An island jewel on the North Shore of Oahu, this cottage is situated right on the water in a quiet, serene, and peaceful setting. Surrounded by palms and gentle trade winds, the cottage is located in a gated, old-style Hawaiian setting, offering all of the amenities...
Newly Renovated Ocean View Condo 🐳 Stunning Views From The Lanai! 🌅 Kona Reef E-22
Two great views from one lanai (ocean and pool) - oceanfront over the pool. Living room offers a queen-sized sofa bed and other seating to view the ocean or watch your cable TV. Kona Reef has an open floor plan, and your newly remodeled kitchen has an ocean view. Your...
Casa De Emdeko# 323 1/1 Remodeled,Top Floor, Oceanview, AC, Elevators!
Casa#323 is a Beautifully Remodeled Top Floor 1 bedroom, 1 bath condominium at the Oceanfront Casa De Emdeko Condominium Development. This special property is close to the elevator on the 3rd floor for ease of access. Located in the heart of Kailua-Kona, The Casa De...
Honua Kai Resort~9th Floor with Full Ocean View!
Aloha & Welcome to Paradise – Unit 925K at Honua Kai Resort & SpaBrand new interior and exterior paint + all Tommy Bahama furniture!Experience luxury living at its finest in this stunning 3-bedroom, 3-bath condo on the 9th floor of the Konea Tower at Honua Kai Resort &...
Beautifully Updated 3 Bedroom Villa on Fairway with Ocean View
MAUI IS OPEN AND WELCOMING — and eager for your travel business! Despite some rumors, short-term rentals are still legal, and the island and its people want your patronage to help sustain and rebuild the economy after the horrific Lahaina fires. Please come!Wailea is...
Beach, shops, restaurants are steps away!
We have one of the prime units in Plantation Hale, a quaint, two-story, laid-back condo complex with a superb location right across the street from the beach. Ours is one of the only units that was completely gutted and remodeled. We also have an ocean view.Our closest...
North Shore Kauai Villa, Ocean Views, Private Hot Tub with Ocean Views, Beach Gear, AC in Bedrooms
Surf Song, in Princeville Kauai, is a luxury private licensed vacation rental home with four air conditioned bedrooms and four ensuite bathrooms. It is situated on a bluff overlooking the Pacific ocean on the iconic North Shore of Kauai. Enjoy ocean vistas from almost...
Kailani Suite- Corner Ocean View 1 Bd/1ba
SPECIALS TA-200-805-1712-02 In Hawaiian, Kailani means Heavenly Sea...Kailani's panoramic view will connect you to the heavenly ocean in a breathtaking and some say "mystical experience " only Hana can provide.The owners of Bamboo Valley Inn in Haiku, Maui are now...
Spacious 1 Bedrm Unit. Stunning Ocean View, in South Kihei, Maui.
Free Wireless Internet access. Enjoy the ocean breezes and panoramic unobstructed ocean views from this second floor unit. This condo and location will be more than you could ever expect. It sure did surprise us. Great sunrise and moonrises over Haleakala, from the...
Fresh & Clean, Air Conditioned Second Floor Condo in Princeville
Aloha, Welcome to Sandpiper Village . Located in the beautiful North Shore Princeville Resort area. This property is walking distance to Swimming, Snorkel and Surfing Beaches, Princeville Makai Golf, Tennis and Pickle Ball Courts, Restaurants and Shopping. Inside you...
Ground floor unit close to the ocean
Napili Shores F150 is a ground-floor condo with a one-bedroom, one-bathroom layout that can accommodate up to five guests and features a split air conditioning system. Tastefully decorated with Hawaiian-inspired decor, this unit has everything you might need for your...
Spectacular Bottom Floor Villa in Waikoloa Resort
Walk to A-Bay Beach, located within Waikoloa Beach Resort. Welcome to paradise in our spacious 2 bedroom 2 bathroom bottom floor oasis overlooking the 1st hole at Waikoloa Beach Golf Course. The Waikoloa Fairway Complex is conveniently located within the Waikoloa Resort...
High-end condo with open-concept design
E Komo Mai “welcome” to Kapalua Golf Villa 25P 3&4! This 2-bedroom, 2-bathroom villa is nestled on the Kapalua Bay Course and can accommodate up to 6 guests. Enjoy cooking in this fully equipped kitchen that features granite counter tops and full-size stainless-steel...
Beautiful Ocean View Maui Sunset Condo - B213
Escape to the sunny shores of Kihei, Maui and experience the ultimate island getaway at our charming 1-bedroom condo. Nestled just a short 18-minute drive from the stunning Wailea Beach and 10 minutes from the pristine Kamaole Beach Park, you'll be perfectly positioned...
Your Oceanview Corner of Paradise: The perfect condo in the heart of Kihei.
This walk-up condo in the first building of Kihei Kai Nani is across the street from lovely Kamaole II, in a string of the some of the most beautiful beaches on Maui. If you use the map feature, you can see this is in building one - 200 feet from the beach! Yay! Choose...
Outstanding Wailea 3 bed/2 ba Grand Champion #94 - big lanai and ocean views
Bldg. 10 - Unit #94 - New, New New. New roof, new carpet, new appliances, new bed - renewed throughout, an impeccable 3 Bedroom + 2 Bathroom paradise condominium at the Wailea Grand Champion Villas. This is the finest that Wailea Grand Champion Golf Villas has to offer...
EL J222 Remodeled Studio w Pools Hot Tub AC Gym Cabana
Eldorado J222 Remodeled Studio with Private Beach Cabana Welcome to your home away from home at Eldorado J222. We've made it fun and lively, so you'll have an unforgettable time when you stay with us. Enjoy all that Kaanapali has to offer in this spacious studio with a...
Sleeps 4, Full kitchen & AC. Pool, hot tub, tennis court, bbq grills! And Beach!
Aloha, Our studio condo is very cozy and clean! It sleeps up to 4 with a cal. king bed and a queen size futon. The pool, hot tub, tennis courts and bbq grills are all very close by. Located across the street is Kalepolepo Park, which has great beach access and the...
Fully Remodelled View Condo Near Waikiki Beach with Free Parking/WiFi
Hawaii Tax ID No. TA 200-103-3216-01, 2020 NUC No. 90/TVU-1102Contact Owner Debbie for more information.Please note: Pool and Recreation Deck will closed for upgrading in 2025-2026. No refund or discount will given during this period. The Condo is located one block from...
❤️PiH❤️ Family Tides ★ Five Bedrooms ★ Resort Pool & Waterslide Pass
Brought to you by Paradise in Hawaii Luxury HomesWelcome to the newest elegant home, Family Tides, in our Hawaiian Luxury Collection.Family Tides is a wonderful large single level 5 bedroom, 5 bathroom home. With two ohana (family) suites this home is the perfect...
Beautiful Surroundings- Private Lanai- Near Ocean
Enjoy Staying In A Lovely Apartment With private entrance and Lanai in unique nature setting & privacy. Sunny areas with Tropical Flowers & Fruit Trees Surrounded by Native Ohia Trees. One Mile From Ocean Clift-side Trails. Hilo is 25 minutes away, 35 minutes from...
Kauai Exclusive - Hale Awapuhi 2E - Oceanfront Luxury - Steps to the water
Hale Awapuhi 2E is among the most luxurious oceanfront properties in Hawaii. Exclusively gated, this boutique 9-unit project offers panoramic ocean views and beach access just steps from the front door. Boasting three bedrooms with A/C, this elegantly appointed...
Snowbird-friendly condo with ocean view, pool, washer/dryer, lanai, & grill
Kona Ali'i 502Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Conveniently located right on the bay with an unobstructed ocean view, you won't want to leave after staying at this...
Great Unit with a Private Lanai
Our complex is zoned hotel/resort and therefore won't be affected by any future ban on short term rentals, which will be for apartment zoned units only, You can book with confidence and not worry about a cancelation. Unique qualities of this unit are its central...
Steps to the Beach, Dining and Shopping! Spring Specials! Inquire now!
Location is everything with this property. Not only are you less than two minutes from the beach and a large swimming pool, you are also walking distance from restaurants and shops of every kind. This unit is away from the street and on the second floor thus, very...
Puamana 58-1 Oceanfront Comfort in Puamana
Located in Puamana, a 30-acre oceanfront gated community just south of Lahaina, this charming three-bedroom, 2.5-bath townhome offers a tranquil escape amidst Maui’s natural beauty. While the 2023 Lahaina fires affected parts of Puamana, including areas near this...
Unit 120 Island bliss with great views!
A LITTLE ABOUT THIS CONDO....Welcome to Polynesian Shores 120—your perfect island retreat! This beautifully designed condo embraces warm tropical décor, creating a cozy and inviting atmosphere.After a day of exploring Maui’s breathtaking beauty, unwind in the living...
Resort Living Off the Beaten Path AC, WIFI, and Fully Remodeled Bathroom
The fabled North Shore of Hawaii is a hidden jewel off the beaten path. Enjoy wonderful dinners watching the sunset on your peaceful breezy lanai.This spacious condo has 1 bedroom, 1 bath, plus loft with 2 queen beds and is fully air conditioned and can sleep 6. Kuilima...
🏝 Private Home, Large Lanai -2 Minute Walk to Poipu Beach! 🐠
Welcome to Kipuka Hale, a beautiful designed, newly renovated home. Located in a quiet, stunning neighborhood just two minutes to the world famous Poipu Beach. Our guests have full access to Poipu Beach Athletic Club, which includes a pool, hot tub, basketball/tennis...
1BR Top Floor, Beachfront, Stunning Views, & Poolside Fun Kihei Kai Nani
This property is hotel zoned, and not being affected by the recent proposed legislation.LOCATION! LOCATION! LOCATION! Welcome to Kihei Kai Nani!Kai Nani is centrally located in sunny South Kihei with easy access to famous Kamaole II Beach Park and walking distance to...
LAST MINUTE SUMMER DEALS- Oceanfront getaway in Kihei, Maui.
A perfect oceanfront view from the living room or lanai. Make a coffee or mix up your favorite beverage in the fully appointed kitchen, then sit on the lanai and look at sunrise or sunset from this oceanfront unit. It has everything you need to be the perfect home base...
Wailea Elua Village 1001 - 2 Bedroom Oceanfront Condo
Wailea Elua Village #1001 is a stunning oceanfront sanctuary that has recently undergone a complete transformation. For discerning travelers who enjoy the best of Wailea, the extended outdoor living space allows you to enjoy panoramic ocean views while relaxing with a...
KKSR#3203 DIRECT OCEANFRONT, 2ND FLOOR, REMODELED, SPECTACULAR VIEWS!
Keauhou Kona Surf & Racquet Club#3-203 DIRECT OCEANFRONT, 2ND FLOOR OF BUILDING#3 in complex! #3-203 is extensively upgraded & remodeled.A truly beautiful oceanfront condo in a gated complex with unobstructed ocean and Kailua town views. Elegant furnishings in this...
Island oasis on golf course w/private lanai, pool, tennis, WiFi, & ocean views
Waikoloa Villages E108Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Find yourself enjoying a favorite beverage while overlooking the signature sixth hole of The Village Course at...
Spacious studio condo with private lanai, kitchenette, & shared pool
Island Colony 3414 - 30-Night MinimumOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Island Colony is a gorgeous, modern building in the heart of Waikiki that offers guests access to...
Amazing private home with AC, Pool, Garage, Hot Tub and Toys N27C
PROPERTY DESCRIPTIONWelcome to your immaculate North Shore oasis! This 3-bedroom, 2.5-bath home is surrounded by tropical foliage, with a lagoon-like pool with a hot tub and expansive sun deck. This upscale rental is a fantastic spot for families, weekend excursions,...
Great 2025 Rates!! Koa Resort Unit 4I - Spacious and Beautiful 3 Bdrm / 2 bth
Koa Resort Unit 4i offers an ideal setting for a serene and enjoyable vacation in a tropical paradise. Situated on the second floor, this renovated condo features three bedrooms and two bathrooms, accommodating up to six guests comfortably. Each bedroom is equipped with...
OCEANFRONT, gated Kapalua Bay Villa 29B4 - Molokai view, steps to water!
Discover the beauty and tranquility of Maui at this newly renovated 1-bedroom, 1-bathroom villa in the exclusive oceanfront community of Kapalua Bay Villas. Nestled within a secure, gated 16-acre enclave of lush tropical landscape, this elegant retreat offers...
Mahina Kai: Large Tropical Modern Home with Pool, Ocean & Koko Head Views & A/C
Welcome to Mahina Kai, a serene 5-bedroom, 3-bath retreat in Hawaii Kai offering panoramic views of Koko Crater, the marina, and the deep blue Pacific. This beautifully designed two-level home spans approximately 2,567 sq ft of bright indoor–outdoor living, featuring...
Sleeps 6! Palm Villas B23, 2 bed plus 3rd bedroom loft! Walk to Beach!
Please be advised that during the month of September 2025 the pool will be closed for maintenance.There will possibly be noise from the pool area as it is getting refurbished. This beautiful and spacious condo at the Palm Villas at Mauna Lani Resort is located on Pauoa...
Maui Banyan Q-109 | Tropical w/ Resort Amenities
Maui Banyan Q-109 is an idyllic condo for an idyllic vacation. Not only is the ground-floor unit across the street from Kamaole Beach II and a short walk from Kamaole Beaches I and III, but it’s also within a gorgeous resort that features swimming pools, tennis courts,...