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.
Paradise Resort Home in Ko Olina | TCP-1220-3
Welcome to your dream vacation home at Coconut Plantation - the most amazing destination in Ko Olina! Whether you're looking for a breathtaking sunset, a romantic getaway, a fun beach stroll, an exciting round of golf or a relaxing spa retreat, this resort has got you...
Manele Bay, Lanai Hawaii Ocean Facing Home
Spacious home on the island of Lanai. Footsteps from Four Seasons at Manele Bay Hotel and Hulopoe Beach. All the comforts of home in an island paradise. Two bedrooms, each with king-sized beds, and two and one half baths, including an outdoor shower. Ocean view and...
Luxury Beachfront Escape! Lae Nani 411| 3BD with Ocean Views, Beach Access, Heated Pool & A/C!
Welcome to Lae Nani Kaua‘i – Starfish #411. Your Oceanview Retreat with A/C and Direct Beach AccessExperience laid-back island luxury in this beautifully renovated 3-bedroom, 2-bathroom ground-floor condo. Located in the coveted Lae Nani resort, “Starfish”...
Steps Away from the Beach! 3 Premium Units, Private Lanai, Onsite Pool
Our spacious suites with private lanais offer breathtaking views of the pristine shoreline, courtyard, or garden, providing the perfect backdrop for relaxation and adventure. Stay connected with high-speed internet, unwind in our unique whale-shaped outdoor swimming...
Kahala Lani: Balinese-Inspired Home with Private Pool
Set in the prestigious neighborhood of Kahala on O‘ahu’s sunny south shore, Kahala Lani by Gather offers a refined island retreat designed for family gatherings and relaxed luxury. Blending island-style architecture with Balinese-inspired touches, this five-bedroom,...
Kaanapali Alii | 341
Welcome to Kaanapali Alii 341, a luxurious oceanfront vacation rental that promises an unforgettable stay in paradise. Nestled along Maui's stunning western shoreline, this property offers breathtaking views of the Pacific Ocean, the islands of Lanai and Molokai, and...
Located In The Historical District And Near The Beach! Pet-friendly, Bar, Pool
Come for the beaches, stay for the adventure! With comfortable amenities and convenience to local attractions, you’ll have everything you need for a relaxing getaway or exciting family vacation. Take a dip in the rooftop pool with views of Waikiki. Enjoy a meal at the...
Charming 1-bedroom condo at Luana Kai in Kihei with WiFi B204
B204 is a charming one-bedroom, one-bathroom unit, situated on the 2nd floor (NO elevators so you are walking up stairs) is a wonderful tropical oasis for your dream vacation. Step into a spacious living area that comfortably accommodates up to four guests, making...
*NEW 3BD Luxe Beach Estate |Pool, PickleB, Gym| AC
Welcome to our luxury 3BR/3BA estate in Poipu Beach Estates, just ½ mile from the beach. Perfect for families or groups, the property offers a beautiful common area with 2 large outdoor Lanais. Enjoy AC in each of the bedrooms, premium kitchen with quartz, and modern...
Island Charm Retreat at Inn on The Park | Walk to the Beach
Incredibly located and uniquely designed, enjoy the ocean and Diamond Head views that dazzle from the quiet of the private lanai of this charming Waikiki unit. As part of the Inn on The Park building, our guests enjoy access to building amenities during their stay,...
The Marbled Suite - Waikiki - Ala Moana - McCullynn
With all the convenience of Waikiki, but with free parking for your rental car. Located between Waikiki, Ala Moana, and the highway (without highway noise). For those looking to also explore outside of the tourist bubble called Waikiki, this location is golden. Minutes...
5-star Four Seasons style renovated gem with A/C and Ocean View
Located in Kailua-Kona, this superb 1st floor condo located in an oceanfront community offers a cozy retreat for guests. With 1 bedroom featuring a comfortable king bed and a well-equipped kitchen with Kitchen Aid appliances,granite counter tops and travertine floors...
Tremendous 5-bedroom homein Kailua-Kona
Modern Kona retreat just 3.5 miles from the airport! This spacious home features vaulted ceilings, a lanai with partial ocean view, and two fully equipped kitchen — perfect for families or group getaways. Located at 1,070 ft elevation, enjoy cool breezes year-round....
Honua Kai | 2 Free Rental Cars | KBM Resorts | Mountain View 2-bedroom 2 Bath Honua Kai | 2 Units, 4 Bedrooms | HK ML-1385
** 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 Bay Villa 18B2 Gold Oceanfront 2 Bedroom
- Villa closest to Oneloa Beach- Split level villa with no stairs between parking and front door- Tile floors throughout- Updated kitchen with granite counters includes – fridge with ice maker, stove/oven, microwave, dishwasher, cookware, tableware and unique chef’s...
3rd Fl Ilikai | King | AC | Pool
The Space:Enjoy the perfect blend of harbor and ocean views from this beautiful suite, complete with a large lanai ideal for relaxing or watching the sunset. A sliding partition separates the bedroom from the living space for added privacy.Bedroom: King bed with sliding...
Tranquil Marina Front Pool House Resort
Marina Front Property in peaceful Cal-De-Sac with large tranquil salt water pool and marina access.Spacious outdoor patio lounge with BBQ grill and prep station and patio furniture and large TV.Parking for two cars! Close to Hanauma Bay, Kona Brewery, Costco, Koko Head,...
Kaanapali Maui Eldorado Garden View 2 Bedroom
Surrounded by tropical greenery, this two-bedroom garden-view condo is ideal for relaxing after a day at the beach. Located on Kaanapali golf course, it includes a full kitchen, comfortable living space, and plenty of room to unwind with loved ones. Garden View 2...
Lahaina Shores 509 | Peaceful Oceanfront Haven
Lahaina Shores 509 – Pacific Ocean ViewsLahaina Shores is a charming boutique resort located directly on the oceanfront in the heart of historic Lahaina Town. Unit 509 is a 5th-floor oceanfront studio offering privacy and comfort for 2 guests. Step onto the private...
Aston Kaanapali Shores - Studio Resort View - No cleaning or Resort fees
All of our guests have complimentary access to our Maui specialist and support team during their stay.*This condo is in the Aston rental program and is subject to a $10.95/day parking fee to be paid to the front desk on property. {A valid credit card is required to...
Hapuna Beach Residence B13 at Mauna Kea Resort
This impeccable, oceanfront, newly-constructed, ground level island masterpiece offers floor-to-ceiling sliding window walls that create indoor/outdoor living space, a true chefs' kitchen outfitted with professional-grade Wolf, Sub-Zero and Miele appliances, wine...
New Listing, Vistas Waikoloa B203 2/2. Ocean Views
Tropical Retreat at Vistas Waikoloa B203- AC, WIFI and ocean viewsAloha and welcome to your serene escape on the Big Island! Nestled in the heart of Waikoloa Beach Resort, Vistas Waikoloa B203 is a spacious 2-bedroom, 2-bath condo offering comfort, privacy, and ocean...
One Bedroom Condo Across Kamaole Beach Park III
Our one-bedroom condo is conveniently located just a few minutes away from the world-class shops at Wailea which offer fine dining, shopping, a shopping market and nearby Kihei boat ramp for easy access to snorkel, diving, and fishing boat adventures! Enjoy the gorgeous...
Ocean View, Central AC, Pool, Spa, & Hot Tub
Kaanapali Shores Unit 817 is the perfect welcoming retreat for your West Maui adventures! From your private lanai, you’ll enjoy sparkling Pacific views and gorgeous sunsets (even whales at the right time of year) while surrounded by resort-style amenities. This...
Oceanfront Center, Westin Ka'anapali, 2 bedroom, 2 bathrooms, 3/8-3/15/2025!
This 2-bedroom unit in Lahaina is perfect for your escape to paradise. This is a timeshare but is also a hotel that is managed by Marriott. Check prices with the hotel to see what a bargain this price is for our oceanfront center units. Oceanfront studios run $900+ per...
Charming apartment with AC and WiFi in serene Kailua.
New charming studio rental located on the owner's property in beautiful Kailua, Hawaii. Perfectly situated just moments away from stunning beaches, lush landscapes, and quaint town. This cozy retreat offers a unique blend of comfort, convenience, and island charm. The...
Kapalua Ridge Villas | 2 Free Rental Cars | KBM Resorts | 180 Degree Views! | 2 Units, 4 Bedrooms | KRV ML-2159
** 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...
A Marbled Suite near Waikiki, Ala Moana, McCullynn
Fully A/Ced apartment, marble floors, granite counter tops, queen size bed in each room, TV in living room, and a in-unit washer/dryer.Located in between Waikiki, Ala Moana, and UH Manoa, this is the ideal starting and ending point for every day.Less than 15 minutes...
Kapalua Bay Villas | 3 FREE Rental Cars | KBM Resorts | 180 Degree Views | 3 Units, 4 Bedrooms | KBV ML-2029
** 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...
Napili Point | 3 Free Rental Cars | KBM Resorts | Ocean View 1-bedroom Villa At Napili Point Maui | 3 Units, 3 Bedrooms | NAP ML-1565
** 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 Spacious Units with Private Lanais, Outdoor Swimming Pool!
Our spacious suites with private lanais offer breathtaking views of the pristine shoreline, courtyard, or garden, providing the perfect backdrop for relaxation and adventure. Stay connected with high-speed internet, unwind in our unique whale-shaped outdoor swimming...
Modern 3-bedroom Condo - Ocean View!
Amazing ocean views!3rd floor (no elevator). WiFi. 2 workstations w/computer monitors. Cable TV and free streaming apps. AC in kitchen/living room and main bedroom. Fans in all living spaces. Assigned parking . 1 mile from Makaha Beach. Close to other spectacular...
Royal Kuhio 1708 - Spacious Corner Unit w/ Ocean City Views in Heart of Waikiki
Heart of Waikiki - Royal Kuhio (17th Floor)Address: 2240 Kuhio Ave., #1708, Honolulu, HI 968151 Bed | 1 Bath | Sleeps 4Beds: 2 Queen-size beds + 1 Queen sofa bedSize: 436 sq ft + 80 sq ft lanaiView: Partial ocean and mountain viewsKitchen: Fully equipped with oven,...
Honua Kai | 3 FREE Rental Cars | KBM Resorts | Ocean Front | 3 Units, 6 Bedrooms | HK ML-2561
** 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...
7 Nights in a 1-bedroom villa with an OCEAN VIEW April 19-26, 2025
Stroll the white sand Ka’anapali Beach, sharing the sunsets with the isles of Lana’i and Moloka’i in view. Dine in the finest restaurants or grill your own fresh fish and steaks near the pool. Take a short walk along the boardwalk to Dukes, ride to the top of...
Marriott's Waiohai Beach Club : New Years week : 2 Bedroom, full amenities
Experience the unparalleled magic of Hawaii at Marriott Waiohai Beach Club, a premium vacation ownership resort. Located by the ocean on Poipu Beach, we offer Kauai villa rentals and an array of resort amenities for your visit to the Garden Isle. Discover your family's...
Oceanfront with Panoramic Views I Maalaea Kai 416
Wake up each morning to sweeping panoramic ocean vistas visible from the lanai and the expansive floor-to-ceiling windows. From November through March, witness the unforgettable sight of humpback whales breaching just offshore, while sea turtles make their daily...
Kaanapali Alii | 342
Welcome to Kaanapali Alii 342, a luxurious vacation rental nestled in the heart of Maui's popular beach retreat of Kaanapali. This spacious condo offers partial ocean views from its private lanai, making it the perfect escape for your next getaway.Step inside to...
Koa Resort 3i - Spacious 2 bedroom 2 bath with AC near beach
Book with us and come to Maui to explore everything we have to offer!This conveniently located 2 bedroom 2nd floor condo offers easy access to miles of sandy beaches, the Hawaiian Islands Humpback Whale Visitor Center, and an old Hawaiian fish pond that provides both an...
Kapalua Bay Villas | 4 FREE Rental Cars | KBM Resorts | Panoramic Ocean Views | 4 Units, 5 Bedrooms | KBV ML-2053
** 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...
Kolea 15C is a two bedroom penthouse with a nice open ocean view!
Enjoy unparalleled living in this spacious two-master bedroom penthouse condo, featuring stunning ocean views and panoramic mountain vistas, along with an extended floor plan that provides ample space and privacy for two couples or families.Once inside, you will be...
Peaceful Hideaway with Pool, Bikes & Perks
Endless adventure awaits in Kailua-Kona! Whether you're staying for a day or a week, our hotel puts you close to top attractions, local dining, and must-see spots like the Amy B.H. Greenwell Ethnobotanical Garden and Pu'uhonua o Hōnaunau National Historical Park....
Tropical Elegance: Tropical Elegance, Acacia Bar, Jetted Tub & Majestic Views
Welcome to Tropical Elegance by Gather, a beautifully remodeled 1,738-square-foot townhome in Princeville, Kauaʻi. Nestled in the serene Ka’iulani enclave, this refined retreat blends organic mid-century design with contemporary Hawaiian luxury. Surrounded by lush...
Stunningly Spacious 4-Bedroom Condo With Extra Large Panoramic Ocean View Lanai
A true hidden Maui gem! Discover the beauty of Ma'alaea while relaxing in this recently constructed 4-bedroom condo, formerly the iconic WATERFRONT RESTAURANT. This very large 2,250 square foot unit includes 2 king beds, 1 queen bed, 1 queen sofa bed, a fold out bunk...
Honua Kai | 2 Free Rental Cars | KBM Resorts | Ocean Views | 2 Units, 4 Bedrooms | HK ML-1327
** 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...
8th Fl Ilikai 1 BDRM – King | Pool | AC
The Space: Furnished suite combining comfort and convenience – the perfect homebase for your island adventures. Bedroom: King bedLiving Area: Full-size sofa bed, TV, ACKitchen: Open kitchen with ample space in cabinets and rice cookerLanai: Spacious 120 sq ft balcony...
3-bedroom condo in welcoming Ko’Olina Resort with WiFi, AC. Relax and enjoy
Escape to this cool condo in picturesque Ko’Olina. With 3 bedrooms including 1 king, 1 queen, 1 twin, and 1 full bed, this fantastic property is perfect for families or groups. Enjoy the convenience of AC, WiFi, a washing machine, and more. The 2 bathrooms offer a...
Maui Resort Rentals: Honua Kai – 4 Total Bedrooms, 9th Floor Stunning Deluxe Ocean and West Maui Mountain Views!
This exceptional 4BR deluxe ocean view offering that pairs two neighboring 9th-floor residences for over 2300 sq ft of combined interior living area. The suites boast spacious floor plans, luxurious finishes, and breathtaking views of the Pacific Ocean and lush West...
Hear the waves from this 1bedroom suite in Kauai
About this spaceJust three miles from the Lihue Airport, Kauai Beach Villas is a cozy resort that is right on the sand immediately north of one of the best beaches on the island and only one hour from the islands North and South Shores. with the whole family at this...
Kauai Ocean View Escape | Pool, Hot Tub, & Spa Bliss
🌺 Kauai Dreams Escape – Your Oceanfront ParadiseAloha and welcome to your island hideaway on Kauai’s breathtaking eastern shore. 🌴Just minutes from Lihue Airport, this oceanfront retreat is perfectly nestled between Lihue and Kapaa—close to everything, yet...