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.
Marriott Waiohai Beach Club - 2 BR - Island View - Sleeps 8 (SC)
Marriott Waiohai Beach Club - 2 BR Sleeps 8 - Oceanview**PLEASE READ ENTIRE DESCRIPTION BEFORE REQUESTING RESERVATION**Book our Amazing Condo & let The Timeshare Brokers, LLC make the booking process easy!Key Points: -You’re inquiring on a Timeshare for Rent. -Please...
3 Bed Villa Views, Beach, Hot Tub, Pools, Golf
Summary:Corner unit with sweeping golf views, just steps away from the beach. Fully stocked with everything you might desire, steps restaurants or grocery stores. End unit feels like a house, provides privacy from neighbors, while being only steps away from the gorgeous...
Kaanapali Alii 4101
Welcome to Kaanapali Alii 4101, a stunning luxury vacation rental in Maui's exclusive Kaanapali Alii Resort. This deluxe condominium offers breathtaking views of both the Pacific Ocean and the West Maui Mountains, providing an unparalleled island experience. With vast...
Fabulous Poipu 6 bedrooms for 10-12! AC!
New Listing!! The Listing is made up of two separate townhomes just steps apart!This fabulous property located in wonderful proximity to Brenneckes, Poipu, and Kiahuna Beach!Surrounded by a championship golf course, the property enjoys a prime spot on Kauai’s sunny...
Kapalua Bay Villas | 2 Free Rental Cars | KBM Resorts | Large Master Suites | 2 Units, 2 Bedrooms | KBV ML-1984
** 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...
2 Bed Steps to the Ocean April SALE! Best Price in Kauai East Side Free Parking!
Steps to the Beach in Kapaa Town – Perfect Location and ValueEnjoy the best of Kauai’s East Side at this newly remodeled two-bedroom getaway, just steps from the beach and within walking distance to shops, restaurants, and everything Kapaa Town has to offer. This...
Valley Isle Resort #907 - Vacation West Maui
★Free Wi-fi, Free Parking, No Resort Fees★Valley Isle Unit 907 offers a serene escape on Maui's western shore. This oceanfront condo boasts breathtaking views of the Pacific, with Molokai and Lanai in the distance. Enjoy modern amenities, including a fully equipped...
Royal Kahana Maui 1215 Ocean View 1 Bedroom
- 12th floor condo with balcony- Carpet & tile flooring throughout- Fully equipped kitchen with– fridge, stove/oven, microwave, cookware, tableware- Tiled bathroom with walk-in tiled shower with grab bar- Bedroom with 1 king bed- Queen sofa bed in living area- Ceiling...
nWake up in paradise at Plantation Hale D6
Enjoy a private lanai with sunrise views, breezy living spaces, and all the comforts of home — steps from the beach and Coconut Marketplace. Highlights:* Bright + spacious condo with island charm* Private lanai overlooking tropical gardens* Full kitchen for easy...
1-Bedroom Within The Ilikai Hotel!
1 Bedroom Economy Lagoon View on the 8th Floor! This unit features a full kitchen, queen bed, free long distance and wifi. Enjoy this sought-after view of the lagoon and Pacific ocean from your very own, spacious lanai.Just a quick walk away, is Hilton Hawaiian Village...
High-Floor Beachfront Colony Surf Condo w/ Sunset Views, Diamond Head Gold Coast
Wake up to turquoise Kaimana Beach and fall asleep to fiery Hawaiian sunsets. Located on the 12th floor of the iconic Colony Surf, this 1-bedroom suite delivers true “live like a local” comfort with resort-level amenities.There is no air conditioning, so please...
All New Interior: Premium Beachfront Ocean View Condo on Hidden Gem Beach
Come enjoy the warm, soft sands of O’ahu at our cabana where no detail has been left unattended to. Located at one of the most underrated beaches on the island with turtle, dolphin and whale sightings often, we’ve incorporated the latest technology here for you to...
Luxury Coffee Farm -Endless Views -Pool - Now Totally Exclusive
Our entire Estate is for sale. All reservations will be honored out at least 30 nights and we will probably be able to honor reservations out to 90 days depending on circumstances. You deposit and all monies received will be entirely refundable up to 14 days of arrival....
Napili Point | 2 Free Rental Cars | KBM Resorts | Ocean View 1-bedroom Villa At Napili Point Maui | 2 Units, 3 Bedrooms | NAP ML-1535
** 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...
!OceanView New Remodel Near Convention Ctr Waikiki
Remodeled private cozy studio on Niu Street with Ocean, Diamond Head, Ala Wai Canal and city view. Walking distance to Convention Center, Ala Moana, beaches, shops and eateries.Please inquire about other listings in same building!Monthly discounts available!*Guests...
Relaxing Modern Oceanfront Suite–Sleeps 4 adults.
Enjoy this beautifully appointed oceanfront home in Kalapaki Bay. Take advantage of being centrally located with one of the best beaches and bays for SUP, beginner surfing, boogie boarding and more. The home is situated between 2 of the best resorts on the island. Enjoy...
Kapalua Golf Villas | 2 Free Rental Cars | KBM Resorts | Whale Watching | 2 Units, 3 Bedrooms | KGV ML-1337
** 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...
Kapalua Ridge Villas Fairway View 1 Bedroom
Ridge Villas Fairway View 1 Bedroom- The Ridge Villas are perched high above with views of Kapalua Bay Course’s fairway - Fully equipped kitchen includes stovetop/oven, microwave, refrigerator, coffeemaker, cookware, tableware- Bedroom with 1 king bed- Queen sofa bed...
Oceanfront Studio with Panoramic Views - Kapa'a Sands 07
Kapaa Sands 07 – Oceanfront Studio | Queen Bed | Pool AccessWake up to stunning ocean views at this second-floor beachfront studio on Kauai’s Royal Coconut Coast. Kapaa Sands 07 features 1 queen bed, a full kitchen, private lanai, and direct access to a peaceful...
Cozy Sunset Views w/ Lanai - Close to Beach by RedAwning
Escape the hustle and bustle of everyday life and immerse yourself in theserenity of our charming Kailua-Kona Ohana, a delightful 1-bedroom, 1-bathroomvacation rental. Located on the captivating Big Island of Hawaii, this coastalretreat offers a tranquil escape for...
The Modern Kailua Beach House
Relax in this Modern vacation retreat located right across the street from Kailua beach park. Just steps from the white sand beaches of Lanikai/Kailua and minutes from local dining, shopping, and outdoor adventures. This thoughtfully designed home blends sleek...
Waikiki Studio with beautiful view and minutes to beach.
Fully furnished studio. Queen size bed sleeps 2. Complete kitchen, minutes from beach and shopping. Brand new air conditioner. Beautiful unobstructed view from 14th floor. Pool, BBQ lounge area and pay laundry on 5th floor. Near Bus routes to everywhere. This unit is...
Enjoyable 3-bedroom house with AC in Hilo
Discover the beauty of Hilo from this 3-bedroom house. The cool and serene atmosphere of this gorgeous property will make guests feel right at home. With 3 full beds and 2 bathrooms equipped with showers and hair dryer, comfort is guaranteed. It's easy to see why you'll...
Kaanapali Alii | 414
Discover the epitome of luxury in our Kaanapali Alii 414, a stunning ocean-view vacation rental nestled in the heart of Maui's Kaanapali Beach. This spacious and elegant condo is perfect for a family-friendly getaway, accommodating up to six guests with its thoughtfully...
Kona Isle B2 No Stairs, Beautiful unit, AC in bedroom and living room!
Kona Isle B2 — Serene Ground-Floor Escape with Modern ComfortsWelcome to Kona Isle B2, your peaceful island retreat on the sunny Kona coast. This beautifully updated ground-floor condo pairs comfort and convenience with a touch of Hawaiian charm — just steps from...
Maui Resort Rentals: Hilton Maui Bay Villas - Luxurious 1BR Suite!
Nestled among 27 acres of lush tropical gardens, the Hilton Maui Bay Villas is a luxurious, secluded resort located on South Maui's sun-drenched coast. Situated minutes from several upscale resorts, pristine beaches, and championship golf courses, guests will enjoy...
Comfortable Studio at The Palms with Pool, WiFi & A/C - Sleeps up to 4 guests.
Unwind in Honolulu at this welcoming studio. This modern space offers a cozy living room with a queen bed and sofa bed, perfect for a peaceful retreat on the quiet side of the property. Enjoy the convenience of amenities like pool, WiFi, AC, and a hair dryer during your...
Kaanapali Alii Unit 215
Welcome to Kaanapali Alii Unit 215, a luxurious vacation rental in Maui's exclusive Kaanapali Alii Resort. This deluxe ground-floor residence offers breathtaking views of Kaanapali Beach and the resort's lush gardens. With Kaanapali Beach just steps away, you'll have...
1 Bedroom Suite, The Modern Resort & Spa, Honolulu
Enjoy the glamour of this stylish, upscale place. Enjoy Hawaii's capital in style at the Modern Honolulu! Guests have access to a variety of amenities, including a fitness center, gift shop, several restaurants, two swimming pools, full-service spa, concierge service,...
Historic Wailuku Inn: 10 Ensuite Bedrooms | Gourmet Chef Breakfast Included
Summary:Welcome to The Historic Wailuku Inn, a beautifully restored 1924 Maui estate with 10 private en-suite bedrooms, lush tropical gardens, and meandering plumeria-lined pathways. Featured by the Wall Street Journal (Apr 18, 2025) as an authentic alternative to...
4th Fl Marine Surf Studio | Prime Location | Parking
Stay in comfort in the heart of Waikiki, only a short stroll to the International Market Place, restaurants, shops, and the island’s vibrant nightlife. This central location is unbeatable—and your unit includes one free parking stall, a rare bonus in Waikiki!🏠...
Island Surf 308 – Newly Updated with Ocean Views
Island Surf 308 – Newly Updated with Ocean ViewsExtend your escape with our special offer:Book 5 nights at any of these breathtaking properties and enjoy the 6th night free!Stay a Little Longer—On Us!Enjoy a complimentary late check-out and savor every last moment...
Lahaina Luxury One Bedroom Villa at Maui Bay Villas Hilton Grand Vacations
Escape to Maui Bay Villas, Hilton Grand Vacations’ stunning oceanfront resort located along Maui’s picturesque western shore. This one-bedroom villa located n the Mauka side of the resort, blends contemporary island elegance with all the comforts of home, making it...
Gorgeous private home with spectacular ocean views & private pool at Kohala Ranch
Gorgeous home with spectacular views and extra privacy on 6 acres in the Kohala Ranch community. This newly upgraded dream home is perfect for couples and families looking for a spacious three bedroom home where they can relax and enjoy panoramic ocean and mountain...
Private Luxury Home, Steps from the Beach w/ AC: Ranch Beach House Estate
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.Ranch Beach Estate is a hidden Hawaiian gem,...
Cozy 1-bedroom condo in Ocean Front Complex, 2 Lanai's and WiFi in Kailua-Kona.
Unwind in Kailua-Kona at this Ocean Front adorable Kona Makai Condo 5-306 on Alii Drive. Bedroom with a king and loft with a queen bed, guests can enjoy a comfortable stay. The bathroom comes equipped with a hair dryer for added convenience. Kickback, relax, and enjoy...
Walking Distance from Papaloa Beach, Outdoor Pool, Free Parking, Full Kitchen!
Welcome to your ultimate tropical retreat! Walk to Waipouli Beach & Coconut Marketplace, with Opaekaa Falls just a drive away. Perfect for island exploration!This listing is for a room within a hotel.✦ Your room is 725 sq. ft, equipped with complimentary toiletries,...
Waikoloa Hawaii 3 Bedroom Sleeps 6
Please Send An Inquiry Before Requesting To Book By Clicking The Contact Host Tab.This three-bedroom, three-bath condo sleeps 6 and boasts lanai views of the ocean and the 9th hole of The Village Course. The primary suite offers golf course views, a king bed, a TV, and...
Kailua Beachfront Estate by Gather: Beachfront Luxury w/ Pool, Spa & Guest House
Welcome to Kailua Beachfront Estate, an exceptional 7-bedroom, 6.5-bath sanctuary that sleeps up to 14 guests on O'ahu’s most exclusive stretch of sand. Blending timeless coastal architecture with luxurious modern amenities, this 5,902-square-foot residence offers the...
Kiahuna Plantation Resort 161 Ocean View 1 Bedroom
Gaze out at the Pacific from this 2nd floor ocean view condo, just steps from Kauai’s most iconic beach. A perfect blend of comfort and scenery, ideal for couples or small groups. Unit 161 Ocean View 1 Bedroom 1 Bath• Fully equipped kitchen includes full size...
North Shore Oceanfront Retreat by Gather: 5BR Spacious Home Paradise
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.Welcome to North Shore Beachfront Retreat by...
Terrific 2-bedroom condo in Kapaʻa
Aloha and welcome to Paradise. We feature a boutique resort with an old Hawaii feel right in the middle of all the action. We are a 2 bedrooms, 1 and 1/2 bath duplex townhome, sleeping 6. Featuring a King bed in the upstairs master with a balcony to see the ocean, a...
REDECORATED! Like-New Oceanview 4 Bedroom 3.5 Bath Lux Montage Kapalua Grand Residence Sleeps 8!
New Offering! 5201 recently joined Private Paradise Villas our newest "Your Own Private Paradise". An extensive redecoration was just completed as of July 2025. We are thrilled to welcome our first guests to this FULLY redecorated (all new!) villa boasting expansive...
Niu Beach Estate – Private Luxury Meets Island Sophistication
Welcome to Niu Beach Estate, a breathtaking 5-bedroom, 5.5-bath modern plantation retreat set along the peaceful southern shores of Oʻahu. Spanning an expansive 7,711 sq ft of indoor–outdoor living, this newly remodeled estate blends contemporary coastal luxury with...
Kihei Estates G105 Gorgeous Remodeled Condo Home
Book with us and come to Maui to explore everything we have to offer!Enjoy the ocean, restaurants, and shops of Maui all within a couple minutes walk from this 1 bedroom 1 bath island oasis unit in the heart of Kihei. Wander right out to the well maintained grounds and...
Westin Kaʻanapali North 1BR Premium – Island Retreat
Discover your perfect Maui escape in this 1-Bedroom Premium Island View Villa at The Westin Kāʻanapali Ocean Resort Villas North. Offering approximately 750–900 square feet of space, this villa is ideal for couples or small families, with thoughtful details that...
Oceanfront Villa on Kona Coast with breathtaking views
Your home away from home in the Mauna Lani Beach Resort with 5 bedrooms, 7 beds and 9 bathrooms. This villa offers guests a relaxing retreat with an outdoor oasis with 2 pools, 2 spas, and modern amenities like WiFi, a fitness room, and AC. The 9 bathrooms ensure...
Luxury suite overlooking Waikiki skyline with Ocean View
Allure Waikiki #2702 – 1837 Kalakaua Ave.(LEGAL 30-Night Minimum Rental in the Resort Zone! ALL MONTHLY RESERVATIONS ARE SUBJECT TO APPROVAL.)NEW TO OUR INVENTORY! Experience luxury Waikiki living at its finest! This 2-bedroom, 2-bath condominium with high-end touches...
Kolea 8E - 3 Bedroom Ocean View Vacation Rental
Kolea 8E is a three bedroom, three and a half bath villa with a sweeping view of Hualalai and an impeccable ocean view of Anaeho’omalu Bay. It is one of the few front row villas that also overlook the private Kolea Beach Club, where Kolea guests are invited to enjoy...
Kapalua Ridge Villa 1222 Ocean View 1 Bedroom
- Spacious lanai with views toward mountain, golf course, and ocean- Second floor unit, two-level townhome, with multiple stairs from parking to the villa- Tile in kitchen, and bathroom. Carpet in living room and bedroom- Fully equipped kitchen with stainless steel...