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.
Oceanfront Condo 🌅 Large Wrap-Around Lanai Almost Hanging Over The Ocean! 🐳 Hale Kona Kai 413
Full Renovation Completed in October of 2024! Enjoy true comfort and class in this absolute oceanfront condo with large wrap-around lanai, providing a generous outdoor space and expansive ocean view. A stunning walk-in shower with custom tile work, open kitchen design...
#11 Beautiful Ocean View, | 0 Bed, 1 Bath
This studio unit is on the ocean side of the complex and features beautiful ocean views. King Bed in sleeping area as well as a pullout sleeper sofa....allowing for an occupancy of up to 4 guests.Unit comes fully furnished with linens, towels, beach towels, shower...
Vacation condo with grill, AC, pools & hot tub - near beaches
Maui Kamaole M107Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Luxury and privacy meet at this Kihei Condo, located in the condo resort known as Maui Kamaole®, and just minutes...
Ilikai Hotel, Amazing Ocean views! Most desirable location in Ilikai!
Look no further, you've found PARADISE!! Located in the most DESIRABLE spot within the Ilikai Hotel, this corner 2-bedroom condo has the best views of the Pacific Ocean overlooking the Duke Kahanamoku Lagoon & Ala Wai Yacht Harbor. This spacious condo has 1000 sq ft of...
Private and Quiet, Luxury Family-Friendly unit in Fairways at Mauna Lani
FAMILY FRIENDLY: Easy access from Lanai to the Fairways pool and fitness centers. Viking BBQ in downstairs Lanai. 4 small appliances and 7 major household appliances. Our townhouse villa has the warm feel of home, (the owners absolutely love the Big Island!) and...
Sugar Beach Resort Condo w/ Shared Grill, Private W/D - Beaches & Beyond
Sugar Beach Resort PH26Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Join the many guests who return each year to Maui's Sugar Beach Resort to enjoy the spectacular views from this...
Lovely home with lanai & enclosed courtyard, close to beach & restaurants
Maui Kamaole J105Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'You're going to love making new memories with your family in this lovely home located in beautiful Kihei! Gather...
Classy Renovated Studio in Marine Surf Waikiki with Free Parking!
The cheapest vacation rental rooms in Marine Surf Waikiki!!The room rate can be less than a half of other Marin Surf rooms. And less than a third of other hotels in Central Waikiki!!This room is not like hotels, we have the full kitchen and also parking!!This recently...
Best Value in MAUI NOW!!! Specials
The Maui Vista Resort and condo is located at two of the best beaches. Across the street is Charlie Young Beach Park & Kamaole Beach Park I. Cove Park, a great surfing location, is just around the corner and with in walking distance to the Maui Vista complex. The condo...
Beachfront Kihei Sanctuary w/ Lanai & Ocean Views!
Let this alluring beachfront Kihei vacation rental serve as your own personal oasis in beautiful Maui! With 2 bedrooms, 2 bathrooms, a private lanai, and sensational ocean views, this condo leaves nothing to be desired. Wake up early to catch the morning surfing waves,...
Beachfront retreat with lanai, WiFi, pool, & hot tub - prime turtle spot
Maalaea Banyans 105Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Enjoy lying on lounge chairs in front of a beach, watching sunsets from your lanai, or just seeing if the sandy...
Hale Kamaole 264 Second floor condo, easy access to best beach on Maui!
Great Ocean and mountain Views. Two bedrooms with loft. Upstairs master bedroom has king bed,downstairs bedroom has two twin beds. Living room and loft both have queen sofa sleeper. New islandstyle furniture in master and downstairs bedroom which were purchased in Jun...
Ground Floor, Corner Condo with Convenient Location
Hawaii Tax ID: TA-048-876-1344-01TMK: 390180030194Practical and budget friendly! Spacious ground floor unit located at the Maui Vista; walk straight out to the pool from your unit or down to the beach. You will be sure to enjoy the convenience of this centrally...
Hale Kamaole 177 Ground floor condo, easy access to best beach on Maui!
Ocean View from dining room & lanai. Close to pool and BBQ. Comfortable furniture. King bed in bedroom with queen hide-a-bed in living room. Very nice up-to-date kitchen and bathroom cabinets. Walk-in cultured marble shower insert. This condo seems light and spacious...
Keauhou Punahele#D-103 Ground Floor, Spacious Lanai, Personal BBQ, VERY Quiet
Keauhou Punahele#D-103 is a beautiful ground floor 2 bedroom, 2 bathroom condo with approximately 1200 interior sq feet. It sits right on Keauhou Country Club golf course. Enjoy an expansive lanai that reaches from living room to the master bedroom. It's equipped with...
Sugar Beach PH8: Sparkling Ocean Views Await!
Welcome to Sugar Beach PH8, Sparkling ocean views! This 1 bedroom/1 bath is perfectly located in North Kihei right on the beach! This Penthouse condo offers an open and airy feel. Take in a breathtaking Maui sunset right from your private lanai. With seating for four,...
Fourth-floor condo with free WiFi, furnished lanai, shared pool
Kona Pacific C421Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Offering a private, covered lanai with treetop views and a warm and colorful interior, this single-level Kona condo...
Peaceful golf retreat with shared pools
Summary:Discount Golf, Ocean views, On Golf CourseThe Space:Welcome to your peaceful Waikoloa escape, perfectly set along the fairway with breezy ocean views and easy access to beaches, golf, and local dining:- Sleeps 6 | 2 bedrooms | 3 beds | 2 baths- Private lanai w/...
Modern airy villa with thoughtful decor
Kahana Villa F407 is a 1 bedroom, 1 bathroom condo that comfortably sleeps up to 4 guests. This condo provides an open floor plan with an expansive private lanai and ocean and resort ground views. Interior pocket doors open up to the lanai - creating the ultimate Hawaii...
Ocean View w/Kitchenette, Lanai, Washer/Dryer, WiFi, AC, – Waikīkī Shore #1314
Modern décor, open design, mirrored wall, and ample sunlight filtering in from windows and sliders make this 400sf studio seem larger than life! It’s perfect for couples craving a blend of Oahu action and relaxation in a homey retreat that’s all about style and...
Shores at Waikoloa Beach Resort 236 | Golf Views
Summary:Surrounded by golf course views of the Waikoloa Beach Resort, this family friendly townhome is the perfect way to explore the Big Island. Maximum occupancy strictly enforced in accordance with local ordinances.The Space:The tropical resort features luscious...
Waikoloa retreat with BBQ & pool access
Summary:Renovated Kitchen, Ground Floor CondoThe Space:Welcome to your peaceful Waikoloa Village escape - a relaxing island stay surrounded by tropical gardens & resort comforts:- Sleeps 4 | 2 bedrooms | 2 beds | 2 baths- Access to pool, hot tub & gym- Private lanai w/...
Tree House in Volcano Rainforest with a Hot Tub
As you pull up to this grand cedar style home you will truly be amazed by this one of a kind property. You are immediately greeted by a beautiful rain forest that feels calming and relaxing. This room is located on the top floor so will need to be suitable for those...
Bright condo with lanai, pool, grill - recently updated
SandPiper #116aOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Enjoy all Kauai has to offer in this well-located condo at the entrance of the Princeville area. This is a welcoming...
GC 179 Relaxing 3Bedroom Wailea Condo w AC Pools Hot Tub
Grand Champions 179 3Bedroom, 2Bathroom, Corner Unit Set Amidst the 18-Hole Wailea Blue Golf Course. Walk to 5-Star Resorts, Restaurants, and Luxury Shopping at the Shops at Wailea FREE daily activities included with your stay value up to $956! Complimentary admission,...
Kamaole Sands 7-401, Ocean and resort views from your lanai!
E Komo Mai “welcome” to Kamaole Sands 7-401! This lovely, Hawaiian inspired, 2 bedroom 2 bathroom condo has everything you need to enjoy the beautiful island of Maui! Take a swim across the street at Kamaole Beach park and dry off on your private lanai while you take in...
Stunning Maui Island Getaway w/ Ocean View, Furnished Lanai, & Shared Pool
Kihei Akahi D612Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'In an unbeatable oceanview location, this Maui island vacation rental is perfect for your next Hawaiian getaway. Spend...
1 Bedroom Condo, 2 Queen Beds, Full kitchen & Free Parking
** As of April 2025 for approximately 10 - 14 months the pool deck at the Waikiki Banyan will be closed for renovations **The Waikiki Banyan is the perfect family friendly central location in Waikiki. A large swimming pool and several safe outdoor areas to relax and...
🏖️Golf Course View | Concierge Included | Conveniently located | vrKCV
vr-KCV - Mauna Lani Fairways 504, Professionally Managed by Kona Coast VacationsExperience Tranquility at Fairways at Mauna Lani #504Your perfect Hawaiian getaway begins at Fairways at Mauna Lani #504! Nestled within a private, gated community, this luxurious two-story...
Gardenia Room on Tropical Lush Farm in Haiku, Maui with Private Soak Pool
The Gardenia Room is located on the lower level of our Ohana House. Guests have a private entrance to a comfortable king-size bed & a twin bed. Floor-to-ceiling windows look out onto the beautiful lush garden spaces and water feature with a beautiful private pool for...
Kamaole Sands Unit 8105: Ground Floor 2 br Condo w/upgraded AC System
This ground-floor two-bedroom, two-bath Maui vacation rental is decorated with a stylish tropical theme with hues of green and blue. The kitchen features full-size stainless steel appliances. Enjoy your morning coffee or afternoon cocktail on the covered patio. This...
Top-floor ocean-view condo - lanais, 2 pools, hot tub, walk to Brennecke’s Beach
Kahala #322Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Experience an indulgent tropical escape at this fabulous corner condo featuring ocean views and a coveted top-floor locale....
Ko Olina Kai 1033C: 3BR Tropical Haven, Vaulted Ceilings, Steps from Lagoons
Welcome to Ko Olina Kai 1033C, a tranquil 3-bedroom, 3-bath retreat set within the gated resort community of Ko Olina in Kapolei, HI. Offering 1,625 sq ft of airy indoor–outdoor living, this two-story villa is designed for comfort, connection, and effortless relaxation....
Mana Kai Maui Resort condo with private W/D & WiFi - the waves await
Mana Kai Maui Resort 215Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Swim, lounge, and snorkel at the fabulous Mana Kai Maui Resort, the jewel at the end of one of Maui’s best...
Newer to CS rental market! Completely redone w/quality finishes & furnishings.
Amazing completely remodeled Diamond Head/Ocean view Colony Surf condo by renowned Japanese designer. Every detail meticulously crafted to satisfy the most discriminating traveler.This Diamond Head side of Colony surf allows spectacular views of white Fairy Terns...
3-bedroom estate in peaceful Haleiwa Hawaii
Haleiwa is waiting for you at this serene 3-bedroom home plus mother-in-law-suite. With 3 queen beds and 1 king bed, this brilliant property offers a cozy retreat for guests. Enjoy the bathtub, hair dryer, and WiFi during your stay. We're happy to assist with any...
Napili Gardens #4 - Central AC, Near beach, Sleeps 8
*If you need more room, unit #12 is across the hall. Please inquire.Escape to island luxury at our beautiful three-story townhome, perfectly positioned between the world-famous shores of Napili and Kapalua. Designed with a fresh, contemporary island aesthetic, this...
Fairway Villas E-24 2 bed 2 bath on golf course
Summary:This 2 bedroom/2 bath villa is the perfect location for your Hawaiian vacation.The unit features a primary suite with a king sized bed, It has an ensuite bathroom with double sinks and vanity, soaking tub, large glass enclosed shower, and walk in closet. We have...
Beach condo on ground floor. contact for 30 day or more rental discounts
workcations/staycations welcomed. message for special rates- fees normally 125 a night. special promotion $95.00 a night. Enjoy the island from your private secured condo unit on the west side of the island. Enjoy each day traveling the island experiencing what the...
🏖️Spectacular Ocean Views | Close to Town | Free Concierge | vrKCV
vrKCV - Sea Village 3112, Professionally Managed by Kona Coast VacationsExperience the beauty of oceanfront living in this charming 2-bedroom, 2-bath island retreat, perfect for a relaxing Hawaiian getaway. Comfortably accommodating up to four guests, this home offers...
"KA'ANAPALI SHORES GETAWAY" Ocean view 434
AMAZING KA'ANAPALI SHORESWelcome to the gorgeous Kaanapali coast on West Maui, where the Kaanapali Shores beachfront resort rests on 10 acres of white sand, tropical gardens, and flowing waterfalls. The resort boasts the quintessential Hawaii experience. -Condos with...
Royal Kahana 1211, Direct Ocean Views!
This property is hotel zoned, and not being affected by the recent proposed legislation.Maui Oceanfront Luxury Awaits - Top Floor Penthouse CondoNewly UpdatedWelcome to our top-floor penthouse condo in Kahana, where luxury meets location. This isn’t just a place to...
Kealia 409 - Beach front studio
Book with us and come to Maui to explore everything we have to offer!A great studio featuring a queen-sized Murphy bed, a queen sleeper sofa, and window AC—all just steps from miles of sandy beach. You will love the well maintained kitchen and cabinetry. Enjoy your...
Condo w/ Sunset Ocean Views & Shared Pool/Tennis - Beach Across the Street
Kihei Akahi D313Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Enjoy cool ocean trade winds and views of the community gardens, the pool, and the Pacific Ocean at this wonderfully...
Delightful Studio on Lemon Road side at The Waikiki Grand
Legally permitted rental: 134 Kapahulu Ave #218Located on the Lemon Road side of the Waikiki Grand this comfortable and modern 2nd floor Studio is the perfect place to retire to after a day at the beach or hiking up Diamond Head crater. The building is just two mins...
Sugar Beach Resort Condo w/ Shared Pool/Hot tub, Private W/D-Surf, Bike, Golf
Sugar Beach Resort 221Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Join the many guests who return each year to Maui's Sugar Beach Resort to enjoy the spectacular views from this...
Hale Kai Kalani - Hosted By Parrish Kauai - Quaint cottage near the beach & bedr
Hale Kai Kalani (“House of the Heavenly Sea”) is a perfect Kauai cottage situated on one and a half acres of land just up from the picturesque Rock Quarry Beach (also known as Kahili Beach). Conveniently located near Kilauea Town, home of the Kilauea Lighthouse and the...
The Turquoise Turtle - AC / Pool / Ocean View
5/5 star review,·August 2025,·Stayed a few nightsWe had a wonderful vacation at the Turquoise Turtle house! The condo and location are absolutely gorgeous! The view is great and there is a walking path along the cliff. We got in very late and appreciated the supplies...
Home in the heart of Hilo
This ground-floor unit is located in a conveniently situated two-story home in the heart of Hilo, within a pleasant and safe neighborhood. It's within walking or biking distance to most amenities in Hilo town.Nestled on a private, low-traffic side street, the unit is...
As seen on HGTV's Hawaii Life,w/pool,BBQ, hot tub
Sandpiper 120A is a bright and open one bedroom condo, great for travelers on a budget, or who prefer the "local feel". This homey apartment has a full size kitchen, spacious living and bed rooms, a large private lanai, and extended ensuite bathroom and vanity. The...