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.
Whaler at Kaanapali Beach Studio #164
Upgraded and Renovated Studio Garden View condo at the Whaler on Ka'anapali Beach. This spacious studio can sleep up to three people. There is a King bed and a Queen-size sofa bed. Located on the ground floor and a short walk to the beach. There is a 48-inch TV in the...
Kailani #315, Top Floor, Walk to Kapaa Town and Beach, AC
Kauai Kailani #315, Kapaa, Hawaii. Kauai vacation rental conveniently located in Kapaa Town on Kauai’s Royal Coconut Coast. This cute boutique condo is walking distance to the ocean, shops, restaurants, coffee shops and more! No Resort Fees.Newly remodeled Unit! Two...
Luxury 800 ft" 1 bedroom Suite, Full Large Kitchen, King size bed, Free Laundry
Built in 2022!This large luxury1-bedroom suite, the main part of the 4 beds, 3 baths single family house with its own private entrance, is located on a one-acre land harboring the most unique feature of Hawaii Paradise Park in Keaau and offers a real retreat from the...
Fairways 402- Mauna Lani Resort-Private Beach Club Access-Golf Course Front-3 BR
Welcome to our 3-Bedroom Villa within the exclusive, Fairways at Mauna Lani community, located on the North Francis I'I Brown golf course and within walking distance to The Shops at Mauna Lani, Auberge, and the Fairmont Orchid Hotel. Fairways at Mauna Lani 402 is...
Dream of Aloha
— "This property may not be rented for less than 30 consecutive days. Rental prices will not be reduced or adjusted based on the number of days the rental is actually used or occupied." (PER CITY AND COUNTY OF HONOLULU). — This property cannot accommodate long vehicles—...
Epic Forest View, A/C, Fruit Trees, Beach 5m drive
Experience this forest retreat complete with a cozy queen bed, AIR CONDITIONING, vaulted ceilings, convenient kitchenette, half bath, and an outdoor hot/cold shower. Relax on the expansive deck facing breathtaking panoramic views of the untouched jungle. Immerse...
Beachfront Paradise on Sugar Beach - Kihei Beach Resort #408
Look no further, beautifull custom upgrades throughout, oceanfront condo directly on Sugar Beach, the longest stretch of sand Maui has to offer and just steps from your door. Start your morning off relaxing on the lanai listening to the waves while embracing the...
Kaunakakai Vacation Rental w/ Pool Access & A/C!
Escape to paradise at this 1-bedroom, 1-bath vacation rental in Kaunakakai. Located in the highly sought-after Molokai Shores Resort, this condo offers a tranquil getaway with access to a community pool, gas and charcoal grills, a private balcony with ocean views, air...
Kaanapali Alii Residence 445
Kaanapali Alii 4452 Bedrooms | 2 Bathrooms | Sleeps 8 | Garden View________________________________________Welcome to Kaanapali Alii 445, a two-bedroom garden view condo steps from Maui’s famous Kaanapali Beach, that will serve as the perfect retreat for your dream...
Aloha! Come enjoy paradise in our tranquil & relaxing beach villa.
🌺 Aloha & Welcome to Villa O-313We are so happy to share our little piece of paradise with you. Our 2 Bedroom, 2 Bath Villa has been carefully furnished with comfort in mind, so you can truly relax and feel at home from the moment you arrive.Inside, you’ll find a fully...
Coastal Charm Hideaway | 2BR Condo | Kapaa Sands 2
Coastal Charm Hideaway – Oceanfront Escape at Kapaa Sands 2Welcome to Coastal Charm Hideaway, a delightful 2-bedroom, 1.5-bath oceanfront retreat at Kapaa Sands, where the beauty of Kauai's east shore meets the comfort of island living. Enjoy stunning ocean views,...
Seabreeze:110' Oceanfront, Majestic Mountain Views, AC, Outdoor Shower, 30 Daysn
Seabreeze is a beautiful North Shore Hau'ula beach home with 110' of ocean frontage, spectacular sunrises & majestic mountain views. Dine on the lanai with turquoise ocean water so close you can almost touch it. Our home overlooks the sea & mountains (a rare & gorgeous...
Tropical Acreage + Fruit Trees + Beach ~5m drive!
Welcome to "Pua Pono House," on Oahu's captivating North Shore, where country living meets relaxation, away from the hustle and bustle of Honolulu and touristy hotels. Nestled on a lush one-acre estate, our retreat offers a serene and secluded oasis. Centrally located...
Oceanfront, remodeled penthouse, sunsets, whales/dolphins, surfers! Free parking
*Gorgeous views from oceanfront lanai *See whales, surfers, dolphins from lanai *Beach/snorkel/surf right outside *4th Floor Penthouse w/ A/C*Stocked kitchen incl air fryer *Covered parking *Oceanfront gas grill *Da Poke Shack in complex*Pack 'N Play/High Chair *Shared...
Maluhia at Wainani By Parrish Kauai new home with private pool & AC
Maluhia at Wainani is a fresh and stylish modern villa with all the amenities one desires while on vacation. Tucked back away in the quiet part of Poipu, but still perfectly located near the beach, this home is the idea vacation spot. Centrally located in Poipu Beach...
@ Marbella Lane - Paradise Point close to beaches
Summary:Experience an exclusive stay in Makaha Valley. Nestled in a safe gated community, this luxurious vacation home offers picturesque mountain and ocean views that will leave you breathless. Dive into an adventure with snorkeling, hiking, and sightseeing, as you...
Recent remodel - Large 1BR w/ ocean view and walk to excellent beaches/eateries
Recently Remodeled (2021)!Large 1BR unit at highly desirable Shores of Maui. The Shores is a place that people return to year after year, so once you've stayed there you'll likely do the same and return for years to come. A small 50 unit condominium complex with a mix...
Kaanapali Alii 4104 Breathtaking Ocean Views 2Bedroom
Kaanapali Alii 4104 NEW LISTING Enjoy Breathtaking Ocean Views, Top-Notch Amenities, and Direct Access to Beautiful Kaanapali Beach and World Famous Dining and Shops FREE daily activities included with your stay value up to $1035! Complimentary admission, every day of...
Chic 1bd condo, granite kitchen and Pacific views
Noelani 215 offers stunning panoramic oceanfront views with high-end tropical interior décor. The spacious and well-appointed one bedroom, one bathroom condo offers split A/C and all the luxuries you would want at your home away from home. The fully equipped remodeled...
Embark on an extraordinary escape to this remodeled condo at Ka'anapali Royal.
Embark on an extraordinary escape to this recently remodeled 2BR condo at Ka'anapali Royal. Spanning over 1,600 square feet with mesmerizing water-view lanai. Spacious living room, queen sofa bed, and accommodates up to 8 guests. King bed and twin in the primary bedroom...
Air Conditioning,Pool, Surf Boards &Beach supplies,Pool, Lanai,Sleeps 4, kitchen
We are not a resort so you won’t have to sit through any surprise time share spiel/talk. We had to go through that when we were guests. Located in Princeville. Ground floor, corner unit! New Air conditioner, 2 Surf Boards, boogie boards, 4 snorkel gear sets, 4 beach...
Kaanapali Alii Residence 143
Kaanapali Alii 1433 Bedrooms | 2 Bathrooms | Sleeps 8 | Partial Ocean View________________________________________Welcome to Kaanapali Alii 143, a stunning 2-bedroom, partial ocean-view residence, with a fully enclosed den that comfortably serves as a third bedroom....
Gorgeous Condo w/ Ocean View, Near 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...
4 BR, Near Beach, Pool/Spa, Gym, BBQ, Free Prkng
Where adventure meets relaxation: a gated valley retreat with room for the whole family, Makaha Beach just minutes away, and mountain views.Escape to our tropical getaway in the exclusive Mauna Olu Estates, just two miles from world-famous Makaha Beach. Perfect for...
Honua Studio
Escape to our cozy retreat!Honua Studio is located In Waikoloa Village overlooking the Robert Trent Jones-designed golf course.The studio has a comfortable queen bed making it perfect for a couples retreat. Relax and enjoy views of the ocean, golf course and on a clear...
KBM Resorts | FREE CAR | Kapalua Golf Villa | Ocean view | 1-Bedroom Condo, Recently Remodeled! KGV-20T8
** Limited Time Special Offer: Reserve any KBM Resorts property in Hawaii with an arrival date between now and December 31, 2026 for 6 nights or more and receive a FREE 4-door rental car from top providers--Hertz, Alamo, Avis, or Budget. Convenient airport pick-up and...
Laule'a 11: Beachfront Luxury Retreat w/ Private Pool, Spa & Spectacular Views
Experience luxury island living at Laule‘a at the Mauna Lani Resort #11, an elegant 4-bedroom, 4.5-bath retreat nestled within the prestigious Mauna Lani community on the Kohala Coast. This stunning home combines contemporary Hawaiian design with world-class amenities,...
Maui Parkshore Condo with Kamaole Beach Views
Welcome to your comfortable 2-bedroom ocean view condo in South Kihei, the perfect Maui retreat for your dream vacation. The condo's location is just across the street from Kamaole Beach Park III, a popular family beach, making it easy to enjoy the sun, sand, and surf....
Maui Resort Rentals: Honua Kai - 4 Total Bedrooms, Gorgeous Partial Ocean AND West Maui Mountain Views!
This tandem pairing combines two adjacent 2BR/2BA partial oceanview suites to create a four-bedroom offering that provides gorgeous views of the Pacific Ocean and the awe-inspiring West Maui Mountains. Guests will enjoy two modern fully-equipped kitchens, two spacious...
Oceanfront Condo & Pool, Beautiful views & Sunsets
***Professionally Cleaned Condo, No-Contact Check-In/Check Out*** Welcome to Hale Hui Kai 309! This beautiful condo is located within a beach-bungalow style oceanfront Complex, situated on the long span of golden sand that is Keawakapu Beach in Kihei. This 2 bedroom/2...
1 Bedroom Oceanfront Penthouse - Valley Isle 1209
Enjoy this relaxed and private, direct ocean front penthouse condo on Kahana Bay. Spectacular views of Molokai, Lanai & Sunsets. Feel the tropical breezes off of the ocean. Smell the fragrant flowers, dip your toes in the warm island waters. Now you’re in Maui. This is...
Oceanfront Studio in Kahana - Pohailani 201
Ocean Front Studio in Kahana. Remodeled and ready for occupancy! This condo is so close to the ocean you can hear and smell the ocean. Whale watch or view the large sea turtles from our lanai. Sleep like a baby on our Westin Heavenly King bed. Got 2 more? We also have a...
2 Bedroom Oceanfront in Honokowai - Pikake A6
This ocean front corner condo is so light and airy and so close to the water. It is a great 2 bedroom located on the ground floor in Honokowai. The kitchen was updated with new appliances, renovated with granite counters, bamboo cabinets and a glass/stone back splash...
Secluded Waimea Hideaway w/ Lanai & Views!
Experience the beauty of Waimea, HI, like a local while staying at this spacious 3-bedroom, 2.5-bath vacation rental! With a lanai and outdoor dining area, you can enjoy the stunning views of the surrounding mountains while enjoying a home-cooked meal. Explore the...
Breezy Pool Oasis 5BR AC Ocean Views 5min to Beach
Welcome to your tropical paradise getaway! This resort-like 5 bedroom home with swimming pool, hot tub, waterfalls, and stream is ideally located in a quiet cul-de-sac and offers the perfect blend of relaxation, comfort, and breathtaking ocean views. With Magic Sands...
25 Feet Unobstructed Harbor View!
25 feet of unobstructed Kahului Harbor View! Watch whales from the sofa or your desk in this fully equipped one bedroom, one and ½ bath condo. High end finishes and top-of-the-line appliances give you a luxury experience in this centrally located 800 square foot 4th...
Modern Renovated Condo - 1 block to beach, free parking!
See my other Properties # 1503692 and # 3197017 and #3156864 for more 5-STAR reviews and to book multiple units in the same building.Located on the 10th floor of the Waikiki Sunset with beautiful mountain and city views this condo offers enough beds to sleeps 6. 1...
Newly remodeled with AC, gorgeous ground floor condo 87, 3 min walk to beach
Newest addition to our Kiahuna Plantation condos! We just purchased and started renting condo #87. For reviews, please look up our other units - VRBO 1300156, 1587209, and 2160974Dual AC in living room and bedroom.Fully remodeled 1bd/1b condo inside the stunning Kiahuna...
Maui Resort Rentals: Honua Kai Konea 718 – Luxurious 2BR Corner Suite w/ Oversized 450+ sq ft Balcony & Beautiful Partial Ocean & Mountain Views!
Konea 718 is a luxurious 7th-floor two-bedroom corner suite and one of the few offerings at Honua Kai that afford views of both the tranquil blue Pacific and the majestic West Maui Mountains. Take in the dramatic scenery while you dine, entertain, or simply relax on the...
Grand Island Paradise on Golf Course w/Ocean Views
🌅 Relax and enjoy sunset ocean views every night!🏖️We are
❤️PiH❤️ MAUNA KEA BEACH ESCAPE ★ Ohana Suite ★ Pool & Spa
Brought to you by Paradise in Hawaii Luxury HomesWelcome to Mauna Kea Beach Escape, a brand new exquisite 4 bedroom, 4 1/2 bath home located in Hapuna Estates within the Mauna Kea Resort. Prepare to embark on a truly remarkable escape where luxury, comfort, and natural...
Waikoloa Golf Discounts. E2 Waikoloa Fairway Villas
Fairway Villas at Waikoloa E2Please scroll down for detailed informationPLEASE NOTE: Waikoloa Fairway Villas E2 is listed for sale. Guests may be asked to accommodate showings/inspections with 48 hours notice. Please reach out with any questions. 6/16/25This vacation...
Unique 8th Floor King bed condo Full kitchen Slps 3, 2 in 1 WAIKIKI GRAND HOTEL®
Legally Permitted Rental - WAIKIKI GRAND HOTEL®815 One-bedroom Suite 2 Rooms in 1 Space1 King Bed1 Sofa BedFULL KITCHENGrab this one if it pops up for your dates! It is seldom available and often booked far in advance. Some years ago, a much-loved radio personality from...
Papaya & Palm - A Private Tropical Oasis
Come and relax in this private guest home on the western slope of Mauna Kea, Hawaii's oldest dormant volcano. Centrally located and just 15 minutes from the island's best white sand beaches and renowned resorts, this space makes the perfect home base for all your Big...
Oceanview Condo | Walk to Kamaole Beach III | Spacious Kihei Stay w/ Lanai + AC
This attractive 2-bedroom, 2-bath S. Kihei vacation rental overlooks the pool area and offers ocean views beyond. Recent renovations in the kitchen included new cabinetry, granite countertops and backsplash, stainless steel appliances, and fixtures. The bathrooms have...
Maui Getaway | Ocean View | A/C | Pool | Walk to Shops & Dining
This Aloha themed two-bedroom S. Kihei vacation rental located on the 4th floor has all the ingredients for a memorable stay on Maui. The sunlight and wide layout of the living room create an ideal space to sit back and enjoy the flat screen television. There are also...
Garden-Level Condo | Walk to Kamaole Beach II | Peaceful Kihei Escape w/ AC
**PLEASE NOTE: NEIGBORING UNIT D616 WILL BE UNDERGOING RENOVATION FROM 01/05/26 - 03/20/26. EXPECT NOISE**This 2-bedroom, 2-bath, 7th-floor newly remodeled Maui vacation rental offers a level of luxury and convenience few can compete with. Tastefully furnished, the home...
Ground Floor Oasis w/ Lanai & Water Views – Walk to Golf & Shops
Located in the Sandalwood Tower, this ground-floor corner unit Hawaii Island vacation rental offers plenty of natural light to brighten up your Big Island vacation. Between the open-concept living area or open-air lanai you are sure to find your perfect piece of...
Admired Poipu beach house in a perfect location, now a vacation home!
Stay in this beautifully designed vintage Hawaiian style home 350 feet from the Brennecke's Beach side of Poipu Beach park, in the heart of Poipu. Spacious lanais and outdoor living gives everything Kauai has to offer, as well having your private gate leading to the...
NEW !!! DIRECT OCEANFRONT nSUNSETS and crashing waves!Newly remodeled! GORGEOUS
**Boutique Beachfront Condo in Kona - Top Floor Studio**Welcome to the only beachfront condo complex in Kona! Renovated 11/2023 This top-floor studio (3rd floor-no elevator) offers the perfect Hawaiian retreat, just steps from the iconic Magic Sands Beach. Enjoy...