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.
Rainbow Hale Estate Ka'anapali - Luxury Oceanview Estate with Pool & Hot Tub
Maui's Premier Vacation Home! Rainbow Hale Estate Kaanapali – a Family Retreat or Private Honeymoon Get -away. Surrounded by 5 acres of Maui tropical plantation, lies a spectacular estate like you've always dreamed of, with the lifestyle you've always dreamed of...
Beautiful Oceanfront Ohana: Spectacular Views, Pool, A/C, Best Beach&WOW Sunsets
Aloha and Welcome to our Maui Ohana!Relax and recharge at this tropical retreat, perfectly situated within a short walk to Wailea in the Kihei Surfside Resort. Boasting stunning ocean views, direct access to Maui’s best beach, Keawakapu, and a sprawling lawn with a...
Beautiful Ocean Views 5 Bedroom Sleeps 14 Walk to Beach, Pool, AC, & Game room
The "Akai Beach House" is a beautiful 5 bedroom 4 bath home that sleeps 14 with ocean views, a pool, air conditioning and a large game room in the garage. Enjoy ping pong and foosball, or relax on the couch and watch TV in the game room. Magic Sands Beach - the best...
Kiahuna Plantation Resort 203 Ocean View 2 BD 2 BA
- Two story condo with beds and baths downstairs and living areas upstairs looking out to the ocean- Walk-up, no elevators- Bright and airy with tropical accents- Wood floors upstairs, tile downstairs- Full kitchen with granite countertops and backsplash includes full...
The Golden Lotus ~ Pool ~ Jacuzzi ~ Grills ~
A BEAUTIFUL GEM on the North Shore. This LUXURIOUS 2 Bedroom Suite offers HIGH-END COMFORT and Spectacular Ocean Vista, Jungle Valley & Mountain Waterfall Views. Enjoy the Sunsets on the Furnished Balcony. Ceiling Fans in every room - NO AIR CONDITIONING Ideal for...
NEW! Fully Renovated 1BR/1BA condo. 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...
Ocean view Waikiki suite! Free parking, full kitchen, pool, close to beach!
Waikiki Banyan #3508-T1 – 201 Ohua Ave.NEW TO OUR INVENTORY! Enjoy your perfect Hawaiian getaway in this fully-furnished 1-bedroom/1-bath ocean view suite in the heart of Waikiki! 533 square-feet of interior living space, plus a private lanai with gorgeous views of...
Ocean view, fully remodeled, 2nd floor, few steps away from the best beaches
**Welcome to Your Perfect Maui Getaway!**Nestled on the second floor with breathtaking views, our recently remodeled rental unit offers a seamless blend of modern comfort and coastal tranquility. Enjoy stunning vistas from the lanai, overlooking a beautiful green belt...
Kolea 3B - Special Rates Plus Lava Lava Beach Club!!
Kolea 3B Special Rate $550/nt+tax Plus $100 Lava Lava Beach Club for a limited time!3 bedroom, 3.5 bath2nd floor level with semi private elevatorPartial ocean and mountain viewsMaster suite king bed with private lanai, ensuite with dual walk in shower, deep soaking tub,...
Kaanapali Alii | 143
Welcome to Kaanapali Alii 143, a stunning two-bedroom plus den residence designed for ultimate comfort and style in the heart of Maui. This spacious retreat offers ample room for your entire group, making it the perfect getaway. The den can be fully enclosed, providing...
Mokulua Sunrise Ocean Villa Lanikai
This property is offered as a monthly rental. Although full-month occupancy is not required, the monthly rate remains fixed and applies in full, regardless of the number of nights stayed, as prorated rates are not available.Enjoy top-tier luxurious living on your next...
Kimo's Getaway
This a very private duplex. Your host lives upstairs. Your's is a new two bedroom, one bath unit, with a full sized kitchen and adjoining dining area. . There is a large lanai viewing the ocean with plenty of relaxing chairs and an outside dining area.You will be a 7...
$150 off the normal nightly rate ($825) for May 22nd to July 20th dates
Simply built and lushly landscaped for beachside living, Honu offers a comfortable living/dining area and convenient kitchen at the center of the house, with two air-conditioned bedrooms and adjoining full-baths on opposite ends for privacy. Hardwood floors, expansive...
LUXURIOUS OCEAN VIEW CORNER UNIT W/ ALL AMENITIES
You will love our condo that is located at The Whaler with one of the best locations on Kaanapali Beach. We are located right on the beach and a few steps away from Whalers Village. VRBO walking map is incorrect. I think it is about 30 steps from our building to the...
Cozy B&B in Enchanting Kihei-Wailea with AC, WiFi
Enjoy a peaceful stay at this 1-bedroom bed & breakfast in Kihei-Wailea. Forget your worries in this spacious and serene space. Our unit is in the back of the Maui Banyan Resort, away from the South Kihei Road noise, yet a few steps from the beach and has everything you...
15 Steps to the Beach! Ground Floor Completely Renovated on the North Shore
Brand new rental on the North Shore, 15 steps from the beach! This property was 100% renovated in January 2023 and everything is in *MINT* condition. Everything is brand new. You're going to love the tasteful decor, the incredibly comfortable beds and sheets, the...
Hale Joli: Historic Typical Hawaiian Home w/Ocean Views, Lanai & BBQ Area
Welcome to Hale Joli by Gather, a serene retreat that captures the essence of old Hawaii while providing all the modern amenities you desire. This unique three-bedroom, two-and-a-half-bathroom ranch home is a tranquil oasis nestled on a private road, offering you a...
Anini Vista Drive Estate - Kauai North Shore Gem
A grand estate centered on a magnificent lagoon-style saltwater pool with two waterfalls, a grotto, hot tub and bridge, Anini Vista Drive Estate is a paradise in its own right. Inviting ocean views and expansive gardens surround the main house and guesthouse, which are...
Designer Hali'ipua Sunset Sanctuary ~ Hualalai ~ Fire Pit, Personal Concierge
Step into a world of refined beauty at Hali’ipua Sunset Sanctuary, where every detail of the stunning contemporary design—crafted in serene neutral hues—invites you to unwind in luxury. Picture sipping coffee, surrounded by original artwork and custom furnishings,...
One Ocean Mauna Lani Golf Estate 3
Welcome to 6BD Mauna Lani Lux Golf Estate (3) at One Ocean, a brand-new luxurious six-bedroom, six-and-a-half bathroom home built in 2024, nestled in the prestigious Mauna Lani Resort area in Waimea, Hawaii. Perfect for large families or groups of up to ten guests, this...
Adorable with Ocean View at The Cliffs 4209 1/BD 2/BTH
North Shore Living at it's finest! Soak up the Hawaiian sun and salty ocean breezes from this thoughtfully remodeled 1 bedroom, 2 bath condo at The Cliffs in Princeville. With a spacious layout, this airy second floor unit offers a partial ocean view and is just a short...
Luxury OCEAN FRONT Truly 5 Star with A/C, 20' From The Water At Pikake. No fees
Escape to paradise with our exquisite 1-bedroom, 1-bathroom beachfront condo located on the desirable West side of Maui, between Lahaina and Kapalua. Newly installed split unit air conditioning in bedroom and living room!! This stunning second-floor property offers 518...
Beautiful Oceanview Home
Welcome to paradise.This is a private entire house rental with an operator residing on the building site, If any problems arise we are here 24/7 to help, make recommendations, give directions etc, but we keep a low profile and do not use any amenities when guests are in...
Affordable Luxury Oceanview 3/2 @ Hali'i Kai 8H-Family Friendly!
Who says "family friendly" can't have elegant style and fantastic amenities? Our quiet, ground floor unit (8H) has all of the features that you'd like, and a price point that makes it easy to stay longer... Just check our reviews! This has been our "escape from the...
Experience Paradise Summer Special: Updated Kapalua Golf Villa 5-Star Ocean View
Our condo, 26T8 Kapalua Golf Villas, has everything you need for a perfect vacation:COMFORT: Central air conditioning, remodeled kitchen, new furniture, newly carpeted and painted, king bed upstairs, and new sleeper sofa with a memory foam mattress downstairs. VIEW: Our...
Comfortable House close to beaches with Peloton Bike+ and 4 New Trek bikes
Very cute, Newly-remodeled cottage with a modern garage that has been turned into home gym with mat, weights, peloton bike+, and home office table, chairs and monitor. The interiors have completely been redone with new flooring, furniture, new kitchen countertops and...
Maui Kai 306 Oceanfront Condo, Fantastic Ocean Views
MAUI OCEANFRONT CONDOMINIUM... PREMIUM STUDIO... Third Floor.Note: Please read our Guest ReviewsPrime third floor location provides privacy and the best view of ocean surf, whales and sea turtles. Instead of waking up in the mornings to four walls in a tiny one bedroom,...
Maui Townhome across the Street from Pohaku Beach w/ Incredible Ocean Views
We are conveniently located between Kaanapali and Kapalua on Maui’s world famous west coast. Kahana Villa is across the street from Pohaku Beach (S-Turns Park) with white sand and where turtles frequent. You can watch whales from the lanai and master bedroom! All...
Hale Akaka Falls O-121 one of a kind luxury stay
Welcome to Paradise at Hale Akaka Falls O-121Discover the beauty and elegance of this stunning three-bedroom, three-bath villa located in the prestigious Beach Villas at Ko Olina Resort. This luxurious, ground-floor home offers a rare combination of comfort, style, and...
Includes Beach Gear! Kanaloa 303
Kanaloa #303 at Keauhou on the Big IslandPLEASE NOTE: Kanaloa 303 is listed for sale. Guests may be asked to accommodate showings/inspections with 48 hours advance notice. Please reach out with any questions.Please scroll down for detailed informationBedroom...
Kona Islander Inn - #316 - Located in beachfront town of Kailua Kona Hawaii.
Experience the convenience of being close to popular beaches, shops, restaurants, and historic landmarks with this delightful and cozy retreat. Ideal for explorers and relaxers alike, it is your perfect base for memorable adventures and relaxation. You can walk to many...
Breathtaking Views! - Oceanfront! Mahana 813!
BREATHTAKING VIEWS OCEAN FRONT STUDIO MAHANA 813! NORTH KAANAPALI BEACH, A/CWelcome to Mahana 813! Located on the eighth-floor, this oceanfront studio sleeps 2 and features stunning panoramic views of the ocean, beach and outer islands. Living area highlights include...
!New Remodel Oceanview Waikiki AlaWai AlaMoana
New remodeled private, high rise studio in a secured apartment on Niu Street (Waikiki) with ocean view, Diamond head, city light, Ala Wai Canal view. Walking distance to Convention Center, Ala Moana, beaches, shops and eateries.Please inquire about other listings in...
Private Family Oasis Centrally Located by the Beach & All the Local Activities
The Riverhouse at River Estate is a warm and inviting three-bedroom, two-bathroom sanctuary thoughtfully designed to blend timeless Hawaiian charm with modern comforts—perfect for families seeking both relaxation and adventure on Kauai’s North Shore. Inside, the...
Million Dollar Views Oceanfront Studio at The Whaler in Ka'anapali
Aloha! Welcome to Unit #764 at the beautiful and world-famous Ka'anapali Beach and the Whaler! Ka'anapali Beach is a destination featured on the Travel Channel and rated as one of the best beaches in the USA. The Whaler is a popular luxurious ocean front resort in the...
Luxury Beach- and Oceanfront unit! 180° Ocean Views. New remodel with AC
You are invited to spend your best vacation @ 4th floor unit with 180°ocean view. ENJOY:- Direct ocean and beach front- Best Maui beaches next door- Sunsets all year long- Total privacy and superb ocean and beach view from your 4th floor lanai- Counter height lanai...
Westin Ka'anapali 2 Bedroom Oceanview as low as 600 per night
Book a whole week for 4950 plus tax or nightly for as low as 600 per night. (Check calendar for availability)The luxury vacation villas at this resort feature large lanais, stone flooring, granite counter tops, roomy bathrooms, fully equipped kitchens, washer/dryer, and...
Romantic cottage with stunning ocean and mountain views in Captain Cook, HI
Enjoy spectacular views of Kealakekua bay in the newly built Coffee Cottage in Captain Cook, Hawaii! Situated amongst the coffee trees at a pleasant 1350 ft. elevation, it’s a perfect temperature year round. Stretch out in the California king bed and check out that...
Waikiki Living, 4 blocks from surf, mountain views, king size bed and office!
Sunrise on the surf, sunset on the beach, dinner at the top of Waikiki. Enjoy views of Ala Wai canal, Ko'olau mountains and the new park on Aloha Drive from spacious lanais, including your own private lanai. Equipped with A/C, smart TV, microwave and a full kitchen to...
🌺Waiulaula Condo 180 Degree Ocean View 🌺 Member of The Club
Welcome to one of the most beautiful properties within the private gated community of Wai’Ula’Ula at Mauna Kea resort! This upstairs unit, facing out onto the west coast of Hawaii affords a true 180 degree of the Kona coast. One of the most stunning views within the...
Northshore - Paia Beach Town
Walk to the beach and everything in Paia Town. Paia Family House is very spacious, well equipped, with a variety of comfortable indoor, and sweet outdoor living spaces for everyone! There's a yard where kids can play, and views out over the green cane fields. This 4...
Villas By The Cove, Penthouse I · Modern Oceanview Townhome Steps to the Beach!
Welcome to the newest addition to the Villas by The Cove, our Oceanview Penthouse I. This modern home has stunning ocean views, three bedrooms and three full baths, private gated parking, private lanais on both levels, and a large shared heated saline pool and bbq...
Kiahuna Plant. Ground Floor #114,AC, Athletic Club, Tennis Courts and much more
Welcome to Sunny Poipu Beach! Enjoy this ground floor, newly decorated condo and relax on your private lanai while being steps to the sand. Surf spots, long walks and lifeguarded beach are at your fingertips. Fast 200mgb Wifi, fully stocked kitchen, free parking, 24...
Beautiful 2 Bed/2Bath Ocean View Condo
Welcome to Wailea Elua! This 2 bedroom/2 bathroom condo is the perfect location for your dream Maui vacation! The updated kitchen makes it perfect for enjoying meals at home with friends and family. This open airy home a offers beautiful ocean views. Imagine yourself...
KBM Resorts | FREE CAR | Kapalua Bay Villa | Oceanfront | 1-Bedroom Condo, Gorgeously Remodeled! KBV-26B1
Breathtaking oceanfront villa at Kapalua Bay Villas with private lanai, stunning Molokai views, and unmatched privacy-perfect for a serene Maui escape just steps from the ocean and nearby pools.** Limited Time Special Offer: Reserve any KBM Resorts property in Hawaii...
Luxury Aloha Escape Turtle Bay - Kuilima Estates West
Stay comfortably in Kahuku at this 2-bedroom condo. Experience the enchanting atmosphere of this cozy retreat, complete with a king bed and a twin bed. Enjoy the peaceful surroundings and modern amenities like WiFi, AC, and a washing machine. Relax in the living room...
Delightful Historic Cottage Steps from Poipu/Brennecke's Beaches A/C
Just steps from Poipu Beach Park and Brennecke’s Beach, this is an original plantation-style cottage, lovingly renovated and beautifully appointed. It features a new fully-equipped kitchen with granite counters, new bath plus an outdoor shower, two bedrooms, screened...
Magic Sands Light Hawaii Oasis: Steps to Beach, AC ,No Cleaning Fee!
High in Demand & Highly Rated, this beautiful 3 bedroom / 2 bathroom duplex home is only a 3 min walk from Magic Sands Beach. Remodeled & professionally decorated, this charming vacation getaway has all of the comforts you desire in your home away from home, including...
Magnificent Mauna Kea Home With Stunning Views
This 7,768 square foot home was designed by Hawaiian architect Thomas Bingham (a protege of Frank Lloyd Wright) for indoor/outdoor living and entertainment. It has 5 bedrooms, each with a private bath, the master suite enjoying complete privacy on its own floor. The...
Penthouse - 3 Bedrooms 2 Baths
Welcome to our Paradise Home come and relax in luxurious surroundings at our tropical condo, which has been freshly painted, and new air conditioner installed and kitchen renovation, new King Mattress. ( Winter 2016). New appliances, carpet and furniture (2017).Bathroom...