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.
Kapalua's Finest: Luxe Villas with White Sand Beach Access
Nestled in lush gardens and beside pristine beaches, our secluded sanctuaries offer tranquility. Enjoy world-class golf, snorkeling, award-winning spa treatments, and farm-to-table dining. Experience luxury in our fully-equipped villas, with stunning sunsets from your...
Maui, island of the Haleakala Volcano is the heart chakra of the earth
Kapalua's history began in 1836 with Dr. Dwight Baldwin's royal land grant, evolving from an agricultural area (Honolua Ranch/Plantation) to a luxury resort, now known for its golf courses, beaches, and upscale amenitiesKapalua simply is 'A Place Of Life', perfectly...
New Listing In Princeville ~Heated Pool/Jacuzzi
Steps away from the Heated Pool, Jacuzzi and Gas BBQ Grills... This sunlit retreat is designed for a Couples Getaway or Family Adventure. Nestled in the heart of Kauai's lush North Shore, this ground-floor condo combines island charm with all the comforts of home. With...
Kilohana At Poipu By Parrish Kauai - Private Pool with AC - Great for the Family
Kilohana at Poipu is a private tranquil vacation home nestled in the center of Kiahuna Golf Village and the Robert Trent Jones, Jr. golf course. This single-level home has a spacious indoor/outdoor living layout centered around a heated swimming pool and courtyard,...
Beautifully Upgraded, Beachfront, Ground Floor....Dream Vacation!!! #118
Kanai A Nalu (“Gentle Breeze”) is located in Maalaea; a place often called “Maui’s best kept secret”. Our condo is direct OCEANFRONT, BEACHFRONT! You simply cannot get any closer to the ocean than our beautifully upgraded, ground floor unit!From the lanai,...
Alii Cove C-4 Beautiful Beachy Townhome on Alii Drive
Experience the allure of the Alii Cove C-4 Town-home, where exquisite decor meets cozy comfort, perfect for entertaining large gatherings while radiating that charming beach house vibe. The expansive Primary suite exudes glamour and luxury, featuring sumptuous bedding...
Oceanfront Condo, 5G Wi-Fi, King Bed, Hot Tub/Pool, Free Parking
Was recently completely remodeled.Our oceanfront condo is 23ft. from the ocean and is located on the 2nd floor and offers spectacular ocean views and sunsets.Watch the surfers and the dolphins from your lanai. A Short Walk to town and over 20 restaurants.Our...
Heart of Downtown 1 bedroom 1 bath condo 1 reserved parking
This 1 bedroom suite located in the heart of downtown in Executive Centre. Free parking is included! It is 15 minutes to Waikiki, airport. It has central AC, free wifi, and an on-site laundry room. If you don’t have a car, no problem, there are bus stops right outside...
Wailea Elua 3 Bedroom+2 Bath Spacious Beach Home with Oceanview Lanai
Note - individual lanai BBQs are not allowed at this property starting 2/18/22. Wailea Elua Village #502 is an impressive vacation home with new Ohia wood cabinets, cupboards, and accents in the kitchen, new sandstone tile flooring, super quiet new Fleetwood glass...
!DISCOUNTED RATES! FULL ocean view. Rated "EXCEPTIONAL". Renovated. Top Floor.
**The condo is already booked 56% in 2025. I've HEAVILY discounted some dates in 2025. Reserve your stay today before your dates are gone.****NEW elevator just completed 7/2025.****Hale Ono Loa Condos, the resorts at Ka'anapali, the Whalers Village, and Northward...
20% off! Top Floor Waikiki Studio
*30 Day Minimum **www.topofbigsurf.comCharming Studio with Canal View & Balcony – Central Waikiki RetreatWelcome to your peaceful island hideaway in the quiet side of Waikiki! This thoughtfully designed penthouse studio offers hotel-style comfort with bonus perks like...
PANORAMIC GOLF COURSE VIEW HOME "C", MODERN-CLEAN-GATED, NEAR PEARL HARBOR-JBPHH
Welcome to Hillside Perfection on the Greens at Golf Ridge Homes!Discover your ideal fully furnished, 5 bedroom, 4.5 bath air conditioned executive home located in central Honolulu. Perfect for leisure visitors, savvy business travelers and visiting construction teams...
Stunning Kaikea 4Br/4Ba Estate: Luxurious and Private - 5 min from Lanikai Beach
Welcome to Kaikea - a tropical oasis nestled just a short walk away from the pristine white sand and turquoise waters of Lanikai Beach, offering an unparalleled experience of luxury and relaxation. Comprised of two separate structures- one newly built in 2018, along...
Spacious 3BR/2.5BA Townhome in Quiet Ko Olina - Pool, Beaches & Golf Nearby
Escape to our cozy, peaceful 3-bedroom, 2.5-bath townhouse in the serene Hillside Villas at Ko Olina. Just minutes from world-class beaches, golf, and restaurants, our home offers the perfect blend of comfort and convenience for your tropical getaway. Nestled in a...
Guaranteed 2024 Thanksgiving, Christmas & New Years Weeks In Maui, Westin Villas
** Guaranteed dates are: 11/22/2025 - 11/29/2025, 12/20/2025 - 12/27/2027 ****Please email me to inquire about dates before submitting a reservation request**Current Inventory:11/21 - 11/28 - Westin Kaanapali Villas - 1 BR unit - Oceanview - sleeps 4 (flexible on...
Two Bedroom Oasis!
This upscale, high end condo has all the amenities and comforts you could ever want in a vacation rental. A large dining table is located on the lanai where you can sit and watch the whales, boats and surfers. The weekend brings the canoe club and kayakers going by your...
Aloha Condos, Keauhou Resort, Condo 108, Ocean View, AC
Experience perfection at Keauhou Resort Condo 108! This immaculate, renovated condo offers stunning ocean views, breathtaking sunsets, and stellar stargazing from your private lanai. Enjoy top-notch amenities, a fully equipped kitchen, updated appliances, and the most...
2 Bedroom Garden View - Maui Banyan #T108AB
Maui Banyan T108AB: With a functional floor plan and connecting door make this the ideal two-bedroom/two-bathroom ground floor unit for a family getaway. Exotic patterns and warm color tones set the mood while oversized windows allow for natural light and serene garden...
G302: Remodeled Maui Condo with Ocean & Sunset Views, Updated Kitchen & Baths
Beautifully remodeled home at one of Maui’s favorite properties! G302 is one of a handful of condos on property with a fantastic ocean and sunset view as well as views of Haleakala all from your own lanai. The kitchen and both baths have been fully updated. New vinyl...
OCEANFRONT Platinum Five Star remodeled villa! FRONT ROW!! Water views!! 27G1-2
This fabulous meticulously remodeled (recently) extra large one bedroom TWO bath villa (1300 square feet) is located within the Kapalua Bay Villa premier oceanfront complex. This villa, (significantly larger than ALL one bedroom level villas in the resort), is situated...
Spectacular Ocean View, Privacy, Sunsets & Whales from Lanai, Konea Tower #544
Spectacular OCEAN VIEW from our 5TH FLOOR KONEA extra large one bedroom one bath home #544 on the much preferred quiet and shady north side of the KONEA tower. Wake each morning to stunning ocean views from your king-size bed and spacious lanai. Floor to ceiling 'nana'...
LUXURY DIRECT OCEANFRONT! Fully Renovated! Free Parking! Sleeps 6
Waikiki Shore #700 – 2161 Kalia Rd.TRUE direct beachfront unit overlooking the sandy Waikiki shoreline with breathtaking panoramic ocean views! Gorgeously renovated from top to bottom in 2021 with FREE onsite Parking and everything you need for a luxurious Hawaiian...
🏖️Concierge Included | Ocean View | Walk to Beach! | Cental AC | vrKCV
vrKCV - Na Hale O Keauhou E6, Professionally Managed by Kona Coast VacationsEscape to paradise at Na Hale O Keauhou E6! Nestled in the serene and popular Na Hale O Keauhou complex, this townhome offers everything you need for a relaxing Hawaiian getaway. Just a short...
KBM Resorts | FREE CAR | Maui Kaanapali Villas | Renovated Studio Near Beach Central A/C! MKV-B-247
Newly renovated studio at Maui Kaanapali Villas with ocean views, vaulted ceilings, full kitchen, king bed, queen sofa sleeper, and lanai. Steps from the beach, perfect for a peaceful Maui retreat.** Limited Time Special Offer: Reserve any KBM Resorts property in Hawaii...
Beautiful conveniently located 2-bedroom ocean view home in Kailua-Kona.
Beautiful and peaceful two bedroom home with an ocean view and convenient location. Located 7 minutes from the airport and 5 miles from town. Easy access to beaches, grocery stores, and everything Kona has to offer. This two bedroom space is the second floor of a...
Ocean & City Views Renovated Condo at Aloha Towers w/Washer-Dryer & Parking
Book with confidence! This property is professionally managed by Ali'i Beach Rentals, an award-winning property management company.If this particular condo isn't available please inquire about our other beautiful vacation rentals. Feel free to contact us if you have...
Magnificent Mountain Views ~Near Beaches & Village
We've got everything you need to enjoy your holiday: bicycles, boogie boards, beach chairs, umbrellas, BBQ and many other amenities.Only a 15 minutes drive to Hanalei Bay, Hideaways and Aninni Beach and a short stroll to Queen's Bath plus the amenities of Princeville...
Upscale Kailua Getaway: Steps to Swim Beach!
An unforgettable Hawaiian escape awaits at this luxurious 3-bedroom, 2-bathroom Kailua vacation rental home! Sip your coffee on the deck, then walk to Lanikai Beach to enjoy the morning waves. Spend your days relaxing in the private pool, lounging in the hammock, or...
Luxury house in Mauna Kea & Hapuna Resort: Private Pool & Hot tub.
Aloha & Welcome to this slice of paradise at Wai'ula'ula, nestled within the prestigious Mauna Kea Resort. This rare 4-bedroom private home offers sweeping ocean views, a private infinity pool, and a separate Ohana cottage with its own entrance, providing an exquisite...
Mid-century Remodeled Spectacular Ocean Views! 10% Discount for Week+ Stays!
Our spacious remodeled vacation home has amazing ocean, Bali Hai and golf course views and now boasts updated modern bathrooms with Hans Grohe rain showers and fixtures plus a free-standing tub in the master bathroom, state of the art kitchen with Caesarstone counters...
Spectacular View Home for 20! Ocean, Mountain, golf views! 5min from Poipu beach
Brand new listing on VRBO; I'm a Super host for the past 3 years on Air B&BThis newly constructed luxury home sleeps 20+; it's perfection for multigenerational gatherings, vacationing with a few families or large groups. Partial ocean views sits backing the Kukui’ula...
Best Location @ Ekahi... year round sunsets from lanai, stroll to the Beach
What you will love about 14C: * CDC cleaning guidelines implemented * laundry done off site in professional grade CDC protocol machines* “Touchless” checkin * Expansive ocean view from multiple lanais* air conditioned, 3 flat panel tv's, fast internet, sonos...
Legendary Estate 50 Steps to Maui's Best Beach! New! 5 Bedroom, Pool with Slide!
Have you been dreaming about the ultimate Hawaii family vacation? Do you dream of a property that sits across the street from the top beach on Maui? Welcome to this incredible estateAs one of the only properties on Maui this close to an impeccable sandy beach, you'll...
Vintage Kahuna Waikoloa Beach Villas D1
Welcome to our Big Island Kahuna with a Touch of Nostalgia condo in Waikoloa! We are excited to have you as our guests. This beautifully appointed 3-bedroom, 3-bathroom townhome at Waikoloa Beach Villas offers both privacy and convenience. You'll love its close...
Dream Vintage Surf Cottage TVNC 4301
Step back in time in this charming cottage by the beach. Built in the 1920's, this plantation style home will give you a true Hanalei experience. Just steps to the beach and a short stroll or bike ride to many restaurants and shopping. This is a dream location in the...
Hilton Pool Pass thru 2025. Golf Discounts. Waikoloa Beach Villas L2
This vacation rental is professionally managed by ResorticaHawaiiWaikoloa Beach Villas L2Please scroll down for detailed informationBedding Configuration:Master Bedroom: King BedGuest Bedroom: One Queen BedLiving Room: Sleeper SofaHilton Pool Pass: Valid for stays...
G & Z Upcountry Bed & Breakfast Cottage in Kula
G & Z Upcountry Bed & Breakfast Cottage, situated on half an acre in Kula Maui is adjacent to the hosts' 6-acre farm. TMK 2-2-2-006-101-0000.A large jacaranda and two avocado trees shade the wide-open lawn. At an elevation of around 3,000 feet, guests welcome the day as...
🏖️Spacious Townhome | Stunning Golf Course Views | vrKCV
vrKCV - Mauna Lani Village 407, Professionally Managed by Kona Coast VacationsLuxury Mauna Lani Villages Townhome – Golf Course Views & Exclusive Beach Club AccessEscape to paradise in this spacious, luxury townhome nestled within the exclusive gated community of...
Alii Cove#Q3 Beautiful ground floor spacious 2 bedroom with Ac
Alii Cove#Q-3 is an excellent beautifully furnished option for your Vacation. This spacious 2 bedroom, 2 bath unit has fantastic features that many guests enjoy. A perfect option for up to 6 people. ~No stairs! Beautiful Tile and new Laminate Flooring throughout the...
Fairways Ko Olina 27H: Your Ultimate 3BR Retreat in Hawaii with Resort Access
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.Step into paradise with a stay at Fairways at...
Tropical surroundings with home comforts
Welcome to Maui Kamaole I109, a luxurious 1-bedroom, 2-bathroom ground-floor unit that promises an unforgettable Hawaiian retreat. This tastefully decorated condo, designed to accommodate up to 6 guests, is a true home away from home. As you enter, you'll be greeted by...
Luxury OCEAN VIEW Home..Miles of Beach, Sunsets - FULL HOUSE A/C - TVNCU #1076
County of Kauai Vacation Rental License # TVNC-1076 - State of Hawaii Business Registration #s GE-047-578-3168-01 & TA-047-578-3168-01 - 24 hr guest contact: Keenan Driver @ 808-639-0772 (Guest emergencies only) Emergency # is also listed inside the property for quick,...
Fabulous, Spacious Oceanview 3 Bedroom Condo with A/C!
Welcome to Ola Loa Hale!!! (Long Life House) This large three-bedroom, two-bathroom condo is the perfect choice for family and friends traveling together. The home is located in the beautiful Keauhou Kona Surf & Racquet Club, a gated resort community that has long been...
Upscale Oceanfront Penthouse Vistas
Summary:Full remodel and decorated in May 2023 with all new furnishings. This elegant 2-bedroom, 2-bath condo features luxurious touches paired with oceanfront serenity. Located in sunny Kihei at Menehune Shores resort, all of Maui is within reach. Beach chairs,...
Pili Mai 13B 4Bedroom AC POOL
Pili Mai 13B is your perfect Island home… With views of rolling greens and distant ocean views from the lanai and bedroom windows. While the entrancing Ha’upu Mountains greet you with Aloha. Pili Mai is an exclusive resort that provides a wonderful escape while...
Spacious Poolside Villa | Gourmet Kitchen, Lanai
Summary:D211 | TA-018-220-0320-02Welcome to your tropical retreat in sunny Poipu! Villa D211 is a luxurious 3-bedroom, 3-bathroom poolside villa offering 1,600 sq ft of thoughtfully designed indoor-outdoor living. Ideal for families or groups, this elegant space blends...
Contemporary Hawaii Living, Calm North Shore Beach
Experience Hawaii in its purest form in this beautifully built custom home, sitting on an exclusive beachfront property on the North Shore of Oahu. Built with the idea of taking in the gorgeous ocean and mountain views, and maximizing the flow of the trade winds, this...
Amazing condo with pools and hotub across from the beach
Welcome to Maui Kamaole! This wonderful 1 Bed/2 Bath condo is the perfect location for your Maui vacation. It is conveniently located across the street from the Kamole Beach Parks and is nearby shops and restaurants. This updated, fully equipped kitchen makes it perfect...
Very spacious for a one bedroom condo and completely set up with brand new furnishings!
This Hawaiian vacation condo has been beautifully upgraded with stone flooring, dark wood cabinets and granite counter tops throughout.You'll love the ease of a walk in ground level unit with no stairs.An open floor plan leads from kitchen to dining to the sunken living...
Pomaika'i : New Poipu Villa w/Pool+Spa Near Beach
This lovely, spacious South Shore home is the epitome of a laid-back vacation villa: located on the 18th fairway of the Kiahuna Golf Course, splashed with sunlight, canopied by blue skies, surrounded by tropical greenery. With its shimmering turquoise pool and whirlpool...