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.
KBM Resorts| MON-1205 At Montage Kapalua Bay
Incredible 3-bedroom Oceanfront villa at Montage Kapalua Bay, Nano doors, gourmet kitchen, luxe baths, and expansive lanais-perfect for relaxing or entertaining in Hawaiian elegance.** Limited Time Special Offer: Reserve any KBM Resorts property in Hawaii with an...
High on a hill overlooking Ekahi with Great Ocean Views!
Situated on the hill overlooking Ekahi Village, our Ekahi 46D condominium offers great views of the ocean from the living room, kitchen and lanai.The vaulted ceilings in this 2nd level condo enhance its open and airy feeling and nicely displays the Hawaiian wall decor....
Hale Konani, ground flr end unit with AC, golf & ocean views, 9M Pili Mai, Poipu
A stay at Hale Konani in the Pili Mai resort community has everything you need for the perfect Hawaiian vacation. This exceptional well-appointed three-bedroom, three-bath 1,500 sq. ft. condominium with central air conditioning is located on the Robert Trent Jones II...
CONFIRMED DATES for Christmas(Dec 20-27/2024)
WESTIN KA'ANAPALI OCEAN RESORT VILLAS and SpaThis is BOOKED and READY TO GO: BOOK YOUR FLIGHTS!!Minimum 7 night stay Checkin: Friday 4pm Checkout: Friday 10amWe are owners of weeks at the Westin so when you rent from us, we transfer the reservation to your name. If you...
April/May Fill-In Sale! $398/nt!
Welcome to Hale Maluhia (House of Peace), Your Island Oasis at Mauna Lani ResortEscape to Hale Maluhia, where you’ll experience the true essence of Hawaiian hospitality and the serenity of island living. Nestled within the lush, gated Mauna Lani Resort, this...
Red Ginger Garden Studio
Peaceful, well appointed room with private entrance ,down a flight of stairs, overlooking our back yard garden of fruit trees and red ginger blooms. Private bath with shower, queen bed, walk in closet, kitchenette, outdoor seating; Wake up and pick fruit for breakfast...
Hawaii Life Rentals Presents Puu Poa 302
This beautiful third-floor, two-bedroom unit features stunning ocean views from almost every angle and would be perfect for a honeymoon or two traveling couples. The main living area features comfortable, modern furniture with an HD smart TV for all your entertainment...
Holiday Sale! Turtle Bay Villas 311 by Gather: Beachfront w/ Shared Pool/Spa/AC
Please Note: Access to resort amenities is not included, however, the condo complex has its own pool, grills and is just steps to the beach!Prepare to settle into island time a little easier with the unparalleled accommodations and amenities that await you at Turtle Bay...
Spacious condo located near tennis courts, pools & Poipu beach
Kahala #214Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Experience the beauty of Poipu Beach at this stunning condo in the Kahala at Poipu Kai complex in Koloa, HI. Nestled within...
Watch the whales and spectacular sunset views from your balcony!!
.This oceanfront resort in Poipu Beach Kauai, features amazing close views of the ocean, you are less than 100 yards from the ocean and less than a 5 minute walk from an amazing kid safe beach. Walk to stores and restaurants and many other cool shops at Kukuiula Village...
Kanaloa | Unimpeded Views of the Ocean
Summary:Welcome to Kanaloa 2403, a serene 2-bedroom plus loft (that features additional sleeping space) condo with unimpeded views of the stunning blue ocean and the resort pool just steps away. Maximum occupancy strictly enforced in accordance with local ordinances.The...
Luxury Penthouse, Golf View, Gourmet kitchen, Sleeps 6
Aloha and welcome to our home on the Big Island of Hawaii!The island style Fairway Villas in the Waikoloa Beach Resort is the perfect location from which to explore the breathtaking Big Island. Situated just 15 minutes north of the Kona Airport and directly across from...
COMPLETELY REMODELED-AC THROUGHOUT-WELL EQUIPPED-METICULOUS CLEANING
Book with confidence, this nicely updated, 1 bedroom, 2 bathroom (820 sq. ft) condo at Kamaole Sands has been remodeled. This condo is managed by PMI Maui, a local Real Estate Brokerage that specializes in vacation rentals. We are located within a mile of the resort and...
Top-floor condo with amazing ocean/Bali Hai view, lanai, AC, 2 pools & tennis
Hanalei Bay Resort 8233Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Admire unobstructed views of the Pacific Ocean, the mountains, and iconic Bali Hai from Hanalei Bay Resort...
Stay with Us, Memories Guaranteed- 5 star-Decor- Design = Delight! SPECIALS
Kahana Reef #303 invites you to escape the hustle and bustle of everyday life and immerse yourself in your own slice of paradise from this idyllic oceanfront condo, where every moment is adorned with stunning 180-degree water views. When you arrive, mix a tropical...
Malia Kai#18: Beautiful Townhome in Heart of Kona Town: Walk to everything!
Malia Kai#18 is a unique & special rental opportunity for your upcoming Hawaii Vacation! Enjoy Townhome Living with no one above or below you in the heart of Kona Town! Boutique Styled, you'll notice this intimate complex is extremely quiet & the perfect oasis for one...
On the Edge of a Gulch, Privacy, Charm, Unique Style Cottage - Permitted
Maui County Rental permit - BBPH 2011/0001TA-063-891-2512-01/ GE-063-891-2512-01TMK-270360090000Romantic, unique, charming coral rock cottage perched on the edge of Maliko Gulch. Swing in the hammock, or play tennis on the clay court. This is a property for nature...
Ocean Front Condo with Endless Sunset Views
Welcome to Paradise! This bright, newly renovated condo will capture your heart and elevate your appreciation for the tropical heaven that Waikiki is known for. When walking into the unit, you’ll feel as if you’re on your own tropical island as you’re surrounded...
Comfortable, single-level retreat with fast WiFi & washer/dryer - dog-friendly
Puni Mauka A | 31-Day MinimumOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Located less than five miles from Pāhoa for convenient shopping and dining and just two-and-a-half miles...
Honu Point - Luxury Princeville Vacation Home near Sea Lodge Beach
Perched on a peninsula 160 feet above the Pacific Ocean, on what many say is the best lot in the Princeville Resort, our 3 bedroom, 4 bath home offers spectacular white water views from Makana Mountain (Bali Hai) to the Kilauea Lighthouse. Secluded from the street with...
Wailea Elua Village | 910
Wailea Elua Village 910 is a stunning one-bedroom, one-bathroom vacation rental located in the exclusive Wailea community on Maui. This beautifully remodeled condo offers a luxurious retreat a short stroll to one of the best snorkeling beaches on Maui. Located on the...
DISCOUNTED RATES for your Spring and Summer Break!
Unwind in Kapalua paradise at our beachfront oasis, offering breathtaking ocean views, direct beach access, and a serene coastal vibe. Perfect for sun-soaked days, relaxing evenings on the lanai, and creating unforgettable memories with loved ones. This diamond rated...
Hawaiian Oceanfront Oasis
Summary:Escape to our newly renovated oceanfront property for the ultimate island getaway. Enjoy breathtaking ocean and mountain views right from your doorstep, with easy access to the best local food and famous attractions just minutes away. Experience the perfect...
Ground Level Condo Near the Pool!
Experience Princeville like a local in this 2-bedroom condo. Step into this fabulous property and be greeted by the amazing king beds in the bedrooms. The condo also offers enjoyable amenities such as a washing machine, AC, WiFi, a hair dryer, and an iron. With 2...
Beachfront top-floor unit on Oahu's north shore!
LOWEST PRICE YET – 25% OFF FOR JULY 13–AUG 10, 2025! ONLY $130/NIGHT.This remodeled condo is on the top floor of a beachfront complex on Oahu's north shore. Experience the North Shore lifestyle, including breathtaking sunsets, world-class surfing, snorkeling, and...
Welcome to Azure Bay, luxury oceanfront condo
Welcome to our beautiful condo, overlooking Ma’alaea Bay on the south side of Maui. Located in the oceanfront condo complex, Menehune Shores, it is only steps to the beach. Our condo is professionally designed and decorated, including everything to make your stay...
Luxury Condo at Whalers Cove (Unit 135)
Luxury waterfront Condo with fantastic view! Unit 135 at Whalers Cove is a waterfront condo. Elegant furnishings and great amenities throughout add to the comfort and enjoyment of its guests.This gorgeous, upscale Condo resides on the top two floors, in the middle of...
KKSR#10 BEAUTIFUL CORNER TOWNHOME, STEPS FROM THE BEACH, AIR CONDITONING!
Amazing Townhome#10! Corner location, highly desirable, lots of extra light! This beautiful townhome has a very special location, only a few steps away from the Salt and Pepper Sand Beach on site! Featuring 2 bedrooms, and 2 bathrooms, a beautiful option for your Hawaii...
Sunny Poipu Condo w/ A/C close to Beach. Moir Garden and Partial Ocean View #301
Quiet & Relaxing garden view Condo with A/C at Kiahuna Plantation Resort. Inside the condo is newly renovated with island modern furniture, decor and photography by local artist, Steve Munich so you can enjoy the sights of Kauai indoors. There is a private, one bedroom...
KGV 15T5 Kapalua Villa w Panoramic Golf Course Views
Kapalua Golf Villas 15T5&6 Experience Kapalua from our Beautiful Updated 1Bedroom, 2Bathroom Villa with Panoramic Golf Course Views! FREE daily activities included with your stay value up to $1035! Complimentary admission, every day of your stay*: Lu'au, Golf, Whale...
Waialua Beachfront Home, 5 bed/4 bath-Northshore
Welcome to our private, beachfront home on the North Shore of Oahu in Waialua. Wake up to panoramic ocean views on your own secluded estate just steps to the sandy beach. This single story family home has 4 bedrooms and 3 full baths with an additional bonus studio with...
Kaloko mountain cabin above Kona with hot tub and fireplace - rustic adventure!
Escape the crowds of Kailua-Kona by heading up to Kaloko, on the slopes of Mount Hualalai. This cozy, rustic stand alone cabin is situated on 5 acres and is surrounded by native ohia trees and ferns. Kick back on the porch or take the beautiful trail hike just up the...
Breathtaking Sunsets; Upscale Furnishings, Gorgeous Lawns For Kids + You To Play
Just renovated ! Gorgeous Master bath! 1 bedroom, 2 bathroom ground floor condo that sleeps 4. Fully equipped kitchen, outdoor lanai, 2 televisions, in-unit laundry, wireless internet, sofa bed. Unit is approximately 700 square feet. This is an ocean-front property with...
⭐Fabulous Front Row Condo w/ Amazing Ocean Views & Sunsets Pools Spa Free WiFi
Welcome to our little slice of Maui paradise. We travel the world, yet always find Maui our favorite place on earth. We have stayed at Maui Kamaole many times over the years (the first time on our honeymoon!) and always return with the dream of one day becoming an...
Wailea, Oceanfront, Polo Beach Club Condo #403
Location, location, location…. Polo Beach is the premiere condominium that sits at the south end of the Wailea Beach walk, next to the Fairmont Kei Lani resort. Our unit is on the sunny south side of the building, overlooking the pool area and ocean, and south towards...
NEW! 3/BR Coffee Estate with Hot Tub and Ocean View in Kona town
Aloha!! We are new to VRBO but have 25+ 5 star reviews on another popular vacation rental platform. This is truly a unique property and I have no doubt that you will enjoy your stay! This Kona coffee estate is located just minutes from downtown Kona. Centrally located,...
GORGEOUS OCEAN VIEW and Sunsets! Full Kitchen, Washer/Dryer, Wi-Fi, Sleeps 4.
Waikiki Shore #1416 – 2161 Kalia Rd.This cozy 1-bed/1-bath suite boasts breathtaking 14th-floor views of the Pacific Ocean and the greenery of Ft. DeRussy Beach Park next door. Bask in the cool trade wind breezes as you enjoy al fresco dining on your private...
Updated! Steps to Kamaole Beach #1 Great Rates! Great Location MV2107 AC King BD
Welcome to your ultimate Maui getaway at Honu Kihei -- Maui Vista 2107! Building 2 Minimal Road Noise✅ Fully air-conditioned for your comfort (mini-split/living room and air conditioner/bedroom)✅ King Bed ✅ Free Fast WiFi and Flat-screen TV for streaming and...
Poipu Kapili 21 By Parrish Kauai- central Poipu location, ocean & sunset views.
An oceanfront Kauai resort in Poipu Beach featuring spacious Kauai condos and spectacular sunset views. With its classic Hawaii plantation style architecture and design, complemented by a wonderful pool and guest amenities, this is a sought after Poipu resort...
Kapalua Ridge 1421 40%Off May Deals for Relaxing Getaway at Remodeled Condo
The Stice Team — Powered by Gather Vacations. Maui Born and Raised Professionals. Your Local Experts in Crafting Unforgettable Stays.Welcome to Kapalua Ridge 1421, a masterfully re-imagined 1-bedroom, 2-bath townhome perched on the second floor of Kapalua Ridge Villas...
Sunset Makai Hale: Luxury Poipu Oceanfront Home with Pool
This extraordinary 4 bedroom, 4 bathroom luxury home is one of the finest Kauai oceanfront rentals on the island. The grand entrance opens to expansive cathedral ceilings showcasing the magnificent oceanfront living areas surrounded by tropical atriums, lava rock...
Aloha Kai Suite at Wailea Beach Villas. Penthouse 205. Ocean View. 3 BR / 3 BA
Wailea Beach Villas voted as one of the top 100 USA Hotels by the Conde Nast Traveler Readers Choice Awards!Luxury awaits in this exquisite three bedroom, three full baths, 2500 square feet Penthouse Villa J205 with gorgeous ocean view. Our Aloha Kai Suite is elegant...
Wailea Ekahi Village | 39A
If you’re seeking privacy and relaxation, Wailea Ekahi Village 39A offers a secluded Maui retreat nestled behind a lush row of towering tropical plants. This hidden gem provides a tranquil oasis perfect for unwinding after a full day exploring Maui's scenic...
Wailea Grand Champions | 95
Do your Maui vacation right! Wailea Grand Champions 95 is surrounded by tropical landscaping and rolling green fairways, that serve as a constant reminder that you are vacatioing in paradise. This vacation rental offers a perfect blend of comfort and luxury, making it...
Maui Parkshore 208: Beautifully renovated 2 bedroom ocean view condo on Maui
**Please note that the pool will be closed from Wednesday, September 4 through Thursday, September 12 due to pool deck maintenance**This attractive 2-bedroom, 2-bath S. Kihei vacation rental overlooks the pool area and offers ocean views beyond. Recent renovations in...
Oceanfront Home w/ Incredible Lanai, Great Ocean View, WiFi, Washer/Dryer
Hale AikalaniOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'The open waters of the Pacific Ocean are right in your backyard at this modern and comfortable home just outside Pahoa,...
Hale Kainani #6 E Komo Mai: Secluded Luxury Home w/ Pool, Spa, AC & Ocean Views
Hale Kainani 6E Komo MaiSet within the exclusive resort community of Kukui`ula, this luxury Poipu vacation rental offers the ultimate location for your group getaway. The home is brand-new, finished and furnished in comfortable elegance with natural tones for a peaceful...
Luxurious 4BR/3.5BA House: AC, Short Walk To Beach
Discover Elegance at Poipu: The Ohana House hosted by BlueTideVillas.Step into the luxury of the Ohana House, a 2,800-square-foot haven nestled on a half-acre oasis, boasting a sprawling private lanai—perfect for savoring your favorite tropical drink. Celebrated as...
New Upscale Kona Retreat, Ocean Views, Pool, BBQ
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...
Breathtaking Transformation! Luxury 3-BR Oceanfront Condo
When you walk into this oceanfront townhouse the first thing you notice through its expansive windows is the shimmering sea, which is so close it seems to fill up the room. Your eye is drawn across the channel to the neighbor islands of Lana`i and Moloka`i, green...