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.
Full Ocean View, Pool & Spa - 2B2B A/C. Last chance for dates in May.
Full Renovation.Full Air-conditioning, split system, units located in living room and both bedrooms Enjoy your early morning coffee, or afternoon mai tai's and pupu's sitting out on the lanai while watching the humpback whales breaching in the distance, as well as the...
Amazing waikiki Beach condo 2Bed2Bath+free Parking
Listing descriptionAloha, thanks for checking in our property.A newly remodeled 2 bedrooms and 2 full baths (2023). There are 4 double and 2 single beds, full kitchen with kitchenette. It's spacious, almost 1,000 sq. ft. with a patio. It is on the top floor (17) of the...
Private One Bedroom Condo in the heart of Waikiki
Perched near the top of Foster Tower, this high-floor one-bedroom retreat offers an unrivaled vantage point over Waikiki. From the moment you step inside, the sweeping ocean and Diamond Head views create a breathtaking backdrop for your island stay. Sunlight streams...
Condo-walking distance to beach, food & shopping!
This elegant retreat has been completely remodeled, it’s not just a place to stay, it will become a part of your stay. Before even opening the door you're greeted with a pineapple carved into the entry way stone, a symbol of welcome and hospitality. Mountain and...
Panoramic Cityscape Condo at the Waikiki Landmark w/Great Building Amenities
This property requires a minimum 30-day rental. Book with confidence—professionally managed by Ali'i Beach Rentals, an award-winning property management company.. The Waikiki Landmark high rise is located on the main Waikiki strip at 1888 Kalakaua Ave. in one of the...
Gorgeous Keauhou Resort Condo!
1B/1b Short distance to beautiful Keauhou Bay (5 min walk)Please read completely, so that there are no surprises upon your arrival! ❤■ We love the open air lifestyle and find it comfortable with the doors and windows open and the fans going. The breeze on the island...
Captivating Ocean Views from Polo Beach Club 805! Direct beach access.
Book Your Stay and Get a $300 Gift Card!Planning a getaway? Book a stay of 5+ nights between September 24th and November 9th, and you'll receive a $300 gift card to enjoy at some of the best spots around! Choose from Cafe O Lei, Kohola Brewery, or Cool Cats to indulge...
Gorgeous partial Ocean View in the Heart of Waikiki!
Regency on Beachwalk #81 – 255 Beach WalkYou'll appreciate the convenient location of this fully-furnished 8th-floor end unit condo (693 sqft plus two lanais with tables and chairs, for a total of 910 sqft) at Regency on Beachwalk, right in the heart of Waikiki and...
Brand New 4BR Poipu Beach Estates Home
Be among the first to enjoy this brand-new luxury vacation home in the prestigious Poipu Beach Estates neighborhood. Ideally situated between The Shops at Kukui'ula and Poipu Shopping Village, and just a quick five-minute drive to Poipu Beach, this home offers the...
Maluhia Hanalei: Beautiful Hawaiian-Style Home One Block from Hanalei Bay
TVRNC Permit #1020 Maluhia Hanalei is a beautiful Hawaiian-style home just one block from the magnificent two-mile crescent beach at world-renowned Hanalei Bay.The furnishings, amenities, and setting make it a wonderful vacation home from which to enjoy the wonders of...
Kihei Gardens F202 I Bright 2bd Near Beach
Welcome to your ideal Maui getaway! This stunning 2-bedroom, 2-bathroom condo at Kihei Garden Estates offers the perfect combination of comfort, space, and convenience. Located just across the street from the beach, this bright and airy retreat is designed to enhance...
1-Bedroom Tropical Getaway, Kihei Bay Vista
Your home away from home in Maui! Kihei Bay Vista is steps away from white sand beaches while still conveniently located near shops, restaurants, and transportation; 5 mins. in any direction. This 1-bdrm unit is a newly converted rental and shows pride of...
Wailea Beach Villas | PH306
Settle into your very own slice of Maui paradise with a stay in Wailea Beach Villas PH306. This exquisite two bedroom, two bathroom penthouse with exceptional ocean and island views are sure to inspire the luxury, comfort and serenity you deserve. Thoughtfully designed...
Short walk to two beaches in Poipu Kai Resort, Mt. view from Lanai- Makanui #712
Welcome to paradise in this two bedroom, two bath, no stairs ground floor condo that lives like a house. Your favorite part just might be the massive lanai that spans the length of the unit and provides ample room to sunbathe, curl up with a book, or dine in tropical...
Hawaii's Number 1 Luxury Condo "Park Lane" (30 Nights Minimum Stay)
Unit 8301 at Park Lane, offers 2 bed, 2.5 bath, spacious and open lanai with a barbecue grill and relax in your own private in-ground spa, over-looking Ala Moana beach park with a special ocean view. The interior is designed by Clifford Planning & Architecture LLC. The...
Maui Kamaole CONDO M102 TOTALLY RENOVATED
LOCATION: MAUI KAMAOLE, South Kihei (Kamaole III Beach Area), Maui, Hawaii, USATransient Accommodation Registration ID: Fred Coombes TA-214-745-7024-01 GE-214-745-7024-01 Mary Coombes TA-043-043-6352-01 GE-043-043-6352-01(CHECK REVIEWS FROM GUESTS - VRBO)MELIA BUILDING...
Kailua Condo / Townhouse on Oahu 7 day per 30 day period
”Aloha and Welcome Home" message me on availability as it can only be rented once in a 30 day period. Ordinance 19-18 does not require a renter to physically occupy a rental property for any minimum length of time. Remodeled 2x bedroom 2x bathroom condo / townhouse....
Maui Resort Rentals: Marriott's Maui Ocean Club 2BR Oceanview Villa - New Lahaina Tower
Two Bedroom Ocean View Villa at Marriott's Maui Ocean Club - New Lahaina Tower! With its premier location, luxurious accommodatiWith its premier location, luxurious accommodations, and sprawling tropical grounds, Marriott Maui Ocean Club is a perennial Maui favorite,...
Kamaole Villa Conditional Permit 2003/0009
Let go of life's stresses in lavish comfort in this luxurious 3 bedroom, 3 bath, 3 pool beach front home. It has the perfect blend of privacy and seclusion, yet is within walking distance of Kihei's restaurants and shopping.Enjoy sunset dinners on the lanai, beach walks...
Luxury Waikoloa Retreat: 3BR, Hilton Pool Pass!
Welcome to this spacious 3-bedroom townhome, perfectly located in the heart of Waikoloa Beach Resort. With lush landscape views, a short walk to the beach, and complimentary Hilton pool passes, this home offers the ideal setting for your island getaway. Accommodating up...
Luxury Condo at Kameole Beach
Maui Banyan Resort is located a few hundred feet walk from 3 of the most famous beaches in Maui, Kameole Beach I, II, and III. Unit T106 is on the ground floor and is located at the back of the resort with garden views that appreciated for it's peace & quiet as well as...
Luxury Ocean View 2 bed/2bath Beautifully Remodeled; Unit #325
Relax in luxury in this 1100 sf property which has plenty of space to enjoy the views and beaches of south Maui. Quite possibly the nicest and most complete renovation in Hale Kamaole with every detail attended to in its upkeep. Upgraded AC in this modern beach style...
Mauna Lani Beach Club Pass included! 701 Fairways at Mauna Lani
Fairways at Mauna Lani #701: Exclusive Hawaiian ParadisePLEASE NOTE: The swimming pool will be closed for Maintenance Mon-Fri from 8:30am-4:30pm Oct 6-27, 2025. Dates may be subject to change due to unforeseen delays.Discover pure luxury in one of the most desirable...
Luxurious, Spacious, High-end Beachfront Vacation Villa Free Parking
Dreaming of a memorable yet affordable Hawaiian vacation? Our Villa is calling you! It is located on the sunny Western shore of Oahu, and was built as a paradise for family-oriented beach lovers. It is landscaped with beautiful palm trees, koi ponds, a sandy-bottom...
Kihei D-202-Oceanview Condo! Right Next to Dining and Shops
*Panoramic Ocean and Sunset Views*So Very Close to Dining, Shopping and Beaches*Large, Fully Equipped 1 bed, 1 bath CondoExperience the perfect Maui getaway in our stunning 1 bedroom, 1 bathroom condo at Kihei Alii Kai D202. Boasting breathtaking ocean views and...
🏖️AC | Captivating Sunsets | Magnificent Ocean View | Private Pool |vrKCV
vrKCV - Keauhou Estates Hale Ohana lea 11, Professionally Managed by Kona Coast VacationsStart Your Hawaiian Adventure at Hale Ohana Le'aImmerse yourself in the beauty and tranquility of Hale Ohana Le'a (House of Family Joy), a custom-designed Hawaiian retreat located...
Poipu Beach House with AC by Brennecke's Beach
With Brennecke's Beach and Poipu Beach within view and just a short walk away, this two-bedroom, two-bath beach house on Kauai's sunny south shore is a great place to call home when visiting the beautiful Garden Island. Enjoy tropical surroundings, ocean and sunset...
Beautiful 2 BR. Kiahuna plantation condo partial ocean view upgraded with A/C
Kiahuna plantation unit 95 in Building 16.You are very short walk away from a beach, actually 200 steps.On ground floor. Poipu beach is very near.Welcome to Kiahuna Plantation on the sunny south shore of Kauai!. This newly remodeled 2 bedroom, 2 bathroom Kiahuna...
Poipu Kapili 54 - Air Conditioned OCEANFRONT Townhome - Can't beat our views
Located in one of the finest resorts on Kauai, with only 60 units on five beautifully-landscaped acres of Poipu Kapili, this is the perfect home for your family vacation or couples' retreat. The entire home is airconditioned, but also is equipped with screened doors if...
Stunning Kaanapali Oceanfront! Mahana 1107!
PANORAMIC VIEWS 11TH FLOOR OCEAN FRONT MAHANA 1107! NORTH KAANAPALI BEACH, A/CWelcome to Mahana 1107! Located on the eleventh-floor, this one bedroom, one bath condo sleeps 2-4 and features stunning panoramic views of the ocean, beach and outer islands from the living...
Serene Kauai South Shore Retreat, Full A/C, Walk to Beaches
The moment you step out to the private lanai and take a deep breath, the mind is instantly reset by birds chirping in the trees and the tropical foliage all around. You will appreciate the quiet and secluded vibe, yet with easy access to beaches, shops, restaurants....
Surf Hale, Elegant and Luxurious Surf Retreat
Escape to the breathtaking beauty of Princeville, Kauai, and immerse yourself in the ultimate experience that is Surf Hale. Welcome to our luxurious four-bedroom, 2 1/2 bath vacation rental, where paradise meets comfort and adventure awaits at every turn.Nestled within...
Hale Ohia – Private Gated Luxury Estate with Panoramic Ocean Views
Kauai's Premiere Vacation Rental - "Hale Ohia" This private and gated custom estate is like no other. Four suites with private baths lends this home to have constant ocean views. The exceptional out door living area - "Pai Pai" has 2 large drop down TV's for watching...
Holualoa Studio Cottage - GIANT OCEAN VIEW! Cool, private, near town
We are located on the west side of the Big Island of Hawaii, directly above Kailua-Kona, on the side of Mt Hualalai, in Holualoa, with an awesome ocean and coastline view! Please read our reviews because the view from the cottage lanai is better than we can describe in...
Maui Resort Rentals: Marriott's Maui Ocean Club 2 BR Island View Villa – New Napili Tower
2 Bedroom Island View Villa at Marriott's Maui Ocean Club – New Napili Tower! With its premier location, luxurious accommodatiWith its premier location, luxurious accommodations, and sprawling tropical grounds, Marriott Maui Ocean Club is a perennial Maui favorite,...
Coastal Elegance Across from the Beach
Ekahi 20b is a 1 bedroom / 2 bath, tastefully decorated condo in the LOWER VILLAGE of the Ekahi complex, at the bottom of the hill and closest to the beach. In fact, it's only a 2 minute walk to the world renowned Keawakapu Beach so you can maximize your time there for...
Includes Beach Gear! Top Floor, Golf Course Views! Waikoloa Beach Villas I33
This vacation rental is professionally managed by ResorticaHawaiiWaikoloa Beach Villas I33Please scroll down for detailed informationBedding Configuration:Master Bedroom: King BedGuest Bedroom: King BedAdditional Bedding: Sleeper Sofa in the Living RoomAmenties:Beach...
HiltonPass/Discount Golf/Waikoloa Beach Villas J4
Seasoned Host of 18 years with over 185 five star reviews.*Hilton Waikoloa Pool Pass for stays in 2025! J4 Waikoloa Beach VillasWe extend our Gold Golf Membership benefits at Waikoloa Beach Resort Golf to guest renting our villa.Our villa (J4) is one of the FEW larger...
Oceanfront Penthouse Vistas
Summary:Completely remodeled penthouse 1bedroom 1 bathroom oceanfront condo on the top floor!Located in the sunny and vibrant beach town of Kihei. Beach chairs, umbrellas, luxury beach towels and a cooler are provided to enjoy your day at the beach! We strive to achieve...
Emmalani Oasis - Luxe Designer Home with stunning Mountain Views
Welcome to Emmalani Oasis, a beautiful, professionally designed, luxurious home located in the prestigious community of Princeville. Centrally located, Emmalani Oasis is close to the Princeville Park, Shops, Restaurants, Princeville Shopping Center and a quick drive to...
Stunning Sea to Summit View - Spectacular Remodel Just Completed
Wailea Ekahi Unit 41C is a beautiful vacation condominium in the prestigious area of Wailea, known as the ''sunny side'' of Maui.Full renovation completed in Dec 2023! Our spacious, contemporary condo has two master suites and is perfect for families of four or two...
Mala Hale: Elegant Gardenview Home w/Spa, AC, & Serene Lanai w/BBQ - Mala Hale
Nestled in the heart of Princeville on Kauai’s North Shore, Mala Hale is a spacious three-bedroom retreat designed for relaxation, connection, and a true sense of island life. With vaulted ceilings, lush garden and mountain views, and inviting outdoor living spaces,...
Exceptionally Remodeled Oceanfront, Sunsets, A/C, King bed Hale Kai O Kihei
• Oceanfront• Split A/C units• King bed• Remolded Oct 2021• Beach access from condo complexFully remodeled in September 2021, this bright, beautiful one bedroom, one bathroom oceanfront property in Hale Kai O Kihei 210 welcomes you! This second floor condo is...
Keokis Kona Oceanfront Rental
Aloha! This is Casa De Emdeko's premiere unit. It has been remodeled down to the studs. Everything is brand new and sparkling. Plus this is the only unit that literally is perched on the edge of the Ocean Front Salt Water Pool! No other unit has views like this one....
Spring Discount + Free Night in Hawaiian Luxury above Mauna Kea & Hapuna Beach!
Location: Waimea (Kamuela), HawaiiNestled on the scenic Kohala Mountain Ranch Road, Red 'Ohana offers a serene escape on the 'sunny side' of Waimea/Kamuela, perched above Mauna Kea and Hapuna Beach.Enjoy the quaint charm of Waimea, with its gentle breezes and milder...
Single-level, dog-friendly home with a full kitchen, washer/dryer, patio
Puni Mauka | 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 three miles from the ocean, and just a few miles from the heart of town, this secluded,...
Waikoloa Colony Villas 301 - Waikoloa Golf Kings Membership till April 2025!
Welcome to our brand-new vacation rental home. We have a 2 bedroom 2 bath end unit at the Waikoloa Colony Villas located in the Waikoloa Beach Resort. Once you enter the villa, you will be in our great room with brand new furniture, large flat screen tv, one-of-a-kind...
Exclusive, Dream Family Vacation Retreat.
The Royal Palms Estate is perfect for multi-generational families, friends, and groups of fewer than 12 people. Unfortunately, we can not have large weddings or parties. The Royal Palms has 13 Acres Of Exotic Fruit Trees, Tropical Foliage, And Palms. There is 9500...
Ocean View Escape, Walk to Waikiki Beach + 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...