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.
Family Retreat: 2BR Villa at Sheraton Kaua‘i Resort
Located on Kaua‘i’s sunny South Shore, the 2-Bedroom Villa at Sheraton Kaua‘i Resort is the perfect choice for families or groups seeking space, comfort, and direct access to Po‘ipū Beach. With approximately 1,100 square feet of living space, this villa...
Hainoa Villa 2903B
Extensively renovated, this contemporary 2 bedroom, 2 bath single-level upper corner floor villa is the perfect blend of luxury and sweeping ocean views. A spacious primary suite also features majestic ocean views overlooking the entire resort and is complete with a...
Welcome to magnificent views of Diamond Head, Ala Moana Beach!
Located in Honolulu, this 2-bedroom, 2-bathroom condo lets you experience it all. Fans of nature and the outdoors will love being 13 minutes by foot from Ala Moana Beach Park and 12 minutes from Magic Island. Ala Moana Center is an easy 9-minute walk away and Hawaii...
Papakea Resort - Beautiful Ocean Views! 1 BR w/AC
Enjoy stunning sunsets and whale watching at this centrally-located condo. Centrally located in West Maui, this beautiful condo is ocean front! The living room includes a queen sleeper sofa, with a king bed in the cozy bedroom. Located close to world-class beaches,...
Waiulu Villa at Hualalai Resort: Modern 3BR Villa w/ Lanai, Golf Carts & Pool Ac
Important Resort Notices• Sept. 15 – Mid-Nov. 2025: Hualalai Spa will undergo outdoor area enhancements; guests retain access to infrared sauna, hot tub, and pool.• Dec. 1–6, 2025: The Chairman’s Club event may limit amenity access.• Jan. 22–24, 2026: The...
2 Oceanfront units in Kona Bali Kai, with AC - Sleeps 12, 4 bedrooms in total.
This is a combination of 2 separate units that's close from one another. First unit, 3rd floor:Unwind on your private lanai while taking in stunning ocean views, exciting surf action, and unforgettable sunsets.The kitchen comes fully equipped with everything you need to...
Honua Kai Konea 701 Ocean View Penthouse 3 Bedroom
Konea 701 Piilani Penthouse Suite 3 Bedroom- Exclusive on-site provider with the only homes meeting the prestigious AAA 4-Diamond designation - 1 king bed in Master Bedroom - 1 king bed in Second Bedroom - 1 queen bed and bunk bed in third bedroom - 2,300 Sq. Ft.- -...
Marriott Ko Olina Beach Club Ocean Front resort 2 Bedroom Villa.
Great for families! Enjoy a luxurious stay for a fraction of the cost. All of our units are managed and maintained by the resort. Upon arrival, guests will check-in at the resort’s front desk using their resort confirmation # just as if they had booked directly...
HK K206 Maui Condo w/ Lanai, Pools, Beach Access & Mountain Views
Honua Kai K206 Enjoy your Next Maui Getaway from this 2 Bedroom Condo at North Kaanapali, Close to the Hot Tub, Pools, and BeachWelcome to your Maui Retreat: A freshly redesigned 2-bedroom, 1-bath residence nestled within the Honua Kai Resort on West Maui's world-famous...
Kaanapali Alii | 485
Welcome to Kaanapali Alii 485, your perfect luxury vacation rental nestled in the heart of Lahaina. This stunning corner unit offers breathtaking views of the West Maui Mountains, Kaanapali golf courses, and lush tropical greenery. With floor-to-ceiling windows and...
The Lodge at Kukui‘ula - Bungalow 10
Indulge in the opulent comfort of the two-bedroom bungalows at The Lodge at Kukui‘ula on Kaua'i, offering privileged access to the esteemed amenities of The Club at Kukui'ula. This exclusive enclave along Kaua'i's southern coast boasts an 18-hole Tom Weiskopf designed...
Kaanapali Shores | 2 Free Rental Cars | KBM Resorts | Steps To Ocean | 2 Units, 4 Bedrooms | KS ML-1538
** 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...
Kaanapali Shores Stunner! | KBM Resorts | 2 Units, 4 Bedrooms | KS ML-2481
** 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...
Ocean View One Bedroom Luana Kai - Kihei
Recently renovated, this beautifully furnished one bedroom, one bathroom unit is centrally located in Kihei with ocean views. The bedroom has a king size bed and there are ceiling fans in the living room and bedroom, along with AC. The fully equipped kitchen features a...
Stylish Apt with Amazing Views
Kick back and relax in the calm, stylish space. The Aloha Vibes apt was created to recharge your energy from the outside world. The perfect set up for remote workers or vacationers. Start your day sipping your coffee and watching the sunrise and gorgeous view from the...
Gorgeous 3-Bedroom Condo in Ma'alaea With Extra Large Waterfront Lanai
A true hidden Maui gem! Discover the beauty of Ma'alaea while relaxing in this recently constructed 3-bedroom condo, formerly the iconic WATERFRONT RESTAURANT. With 2 king beds, 1 queen sofa bed, a fold out bunk bed, extra large living room, and one of the largest condo...
Waipouli Beach Resort Partial Ocean 1 BD 2 BA
Relax in this light-filled one-bedroom condo with lovely partial ocean views. Perfect for two, it features a fully equipped kitchen, cozy living area, and lanai that’s perfect for enjoying the coastal breeze.Partial Ocean View 1 Bedroom 2 Bathroom• Kitchen features...
Maui Resort Rentals: Honua Kai – 8 Total Bedrooms, Groundfloor Residences, Over 4600 Combined Sq. Ft., Large Lawn Areas, Steps to Pools/Beach/B.B.Q.s!
This remarkable offering combines 4 neighboring ground floor residences at the luxurious Honua Kai Resort to create a perfect retreat for large families and groups. Enjoy the space of a luxury home with all the advantages of resort living.Boasting a combined 4600 sq ft...
Hilton Grand Vacations Lagoon Tower - 2-Bedroom Garden/Partial Ocean View Unit
Escape to this resort in picturesque Honolulu. The Lagoon Tower is situated as part of the Hilton Hawaiian Village--a mecca of shops, restaurants, and beachfront property with a pristine beach, lagoon, and plenty of pools and other activities to keep you and your family...
Maui Resort Rentals: Honua Kai - 4 Total Bedrooms w/ Beautiful Ocean & Lush West Maui Mountain Views!
This impressive 4BR offering combines two adjacent Mountainview residences with a neighboring partial oceanview studio, creating the perfect gathering place for larger groups or families—all at an excellent value!Overlooking the Konea Towers' beautiful courtyard,...
Ala Moana Hotel by Sandra Ocean view and balcony BEST RATE
The hotel unit is located within Ala Moana Hotel and next to the Ala Moana Center, the world's largest shopping mall. There is a skybridge that connect the hotel with the mall. Resort fees are separate ($25/day) and are paid directly to the hotel. The Ala Moana Condo...
Kaanapali Alii Unit 134
Welcome to your dream vacation at Kaanapali Alii Unit 134, a luxurious two-bedroom, two-bathroom family-friendly vacation rental that promises an unforgettable stay. This stunning property offers a partial ocean view, perfect for soaking in the serene beauty of Maui...
Maui Kamaole #C-203 - Remodeled Upstairs Retreat with AC and Resort Pools!
Maui Kamaole #C-203Maui Kamaole #C-203 is a beautifully remodeled two-bedroom, two-bathroom upstairs unit offering a peaceful setting, modern comfort, and a fantastic location near some of South Kihei’s best beaches. This updated condo features island-inspired décor,...
Amazing & Modern Honolulu Haven, Renovated w/ AC
Summary:*** Disclaimer: All rooms are renovated in a similar fashion. Furniture style may vary in pictures and in the unit. Functionality are all the same. Queen size bed in bedroom, sofa bed in the living room. Enjoy a stylish experience at this centrally-located...
Oceanside Kihei Condo | Steps to Beach | AC
Welcome to your perfect Kihei retreat! This beautiful 1-bedroom, 1-bathroom condo at Kihei Kai Nani offers an ideal location just steps from world-famous Kamaole Beach II. The spacious interior features cool ocean blue décor throughout, with a comfortable queen bed in...
Kihei Kai Nani ~ Building 6 Dream Location
Come to this Premier newly remodeled unit at the Kihei Kai Nani. Known for our desirable, ground floor unit. This unit has everything to make this your best vacation yet. Take in the tropical garden and pool view from this 2 bed, 1 bath unit with split AC. The King size...
The Iconic Bamboo House - Unique Vacation Home in Haena
The Iconic Bamboo house is a local famous for its shape and design. Situated in the most beautiful "downtown" Haena, short 2 minute walk to the only restaurant, coffee, bar and spa in the end of the road, also short 2 minute walk to the a white sand beach. being your...
The Secret Manor - artFULL living in Kona Coffee Country
Live like a local on this 5 acre secret estate that can sleep 20 with hot tub in Kona on the Orchid Isle of Hawaii. Designed by architect Skip Goodell. Great for creative retreats & family groups : be close but not TOO close to town or travel companions. Original...
Fabulous 8 bedrooms for 16 Poipu Kai. Steps to beach!
Listing provided by "The Vacation Rental Experts". Contact directly for more options!Beautiful 8 bedrooms for 16 in Poipu Kai is located only 250 yards to Brenneckes Beach and 350 yards to Poipu and Shipwreck Beach! Paved walkway from your door to the beaches! Only a...
Penthouse Ocean Views 2bed 2bath 1 pking 5 min Walk to Beach Spacious 1000 sqft
Located in Honolulu, enjoy what this 2-bedroom condo has to offer. With a king bed, a full bed, and a spacious living room with a sofa bed, guests will feel right at home. This marvelous property also features AC, a fitness room, and 2 bathrooms with a hair dryer....
Big Blue Whale - Spacious "Tiny" Home with COLD A/C
Large "tiny" house in the back of the main house now available!A short unpaved walkway along the side of the main house leads you to the back of the yard where this fully remodeled home with your own private entrance awaits. This spacious and clean home-away-from home...
Luxury 1BR Penthouse with Mountain Views – Ko Olina Beach Club
Experience island luxury from above in this 1-Bedroom Mountain View Penthouse Villa at Marriott’s Ko Olina Beach Club. Perfectly positioned on the upper floors, this villa offers sweeping views of Oʻahu’s lush mountains, combining modern comfort with the laid-back...
Fairways 902: Stunning Golf Views, Lanai, Pool, Spa, AC & Beach Club Access
Welcome to The Fairways at Mauna Lani 902 by Gather, a beautifully updated two-story villa offering comfort, modern upgrades, and peaceful golf course views. Located within the prestigious Mauna Lani Resort along the Kohala Coast, this 3-bedroom, 2.5-bath retreat is the...
Charming studio on the 1st-Floor w/ ocean view, lanai, gas grills, pool, W&D
Kepuhi Beach Resort 1156Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Welcome to your serene ocean view retreat in Maunaloa, HI! This charming studio condo offers the perfect blend...
Steps Away from Kalapaki Beach! Stunning Oceanfront Room | Outdoor Pool
This listing is for a room within a hotel.✦ Your room is 1000 sq. ft, equipped with complimentary toiletries, standard quality TV, available with Standard cable.✦ Daily cleaning services included in the nightly price.There are a few additional details to know before...
Oahu's premier vacation ownership resort Marriott's Ko Olina Beach Club
Located in Kapolei, this 1-bedroom, 1-bathroom condo lets you experience it all. Fans of nature and the outdoors will love being 8 minutes by foot from Ko Olina Beach Park and 12 minutes from Honu Lagoon. Your feet will make short work of the 6-minute walk to Ko Olina...
Kaanapali Alii Unit 131
Welcome to Kaanapali Alii Unit 131, a luxury vacation rental nestled in the heart of Maui's exclusive Kaanapali Beach. This stunning condominium offers a serene retreat with breathtaking resort views framed by lush tropical greenery. Ideal for a family-friendly getaway,...
Princeville Kauai Condo Sleeps 3
Please Send An Inquiry Before Requesting To Book By Clicking The Contact Host Tab.Nestled on 22 acres along the beautiful coastline of the North Shore, the resort abounds with tropical foliage and amazing views of the green mountains, waterfalls, tropical sunsets over...
NEW! KBM Resorts Niki Lani Condo | FREE CAR | Kuilima Estates | 3-Bedroom Condo at Turtle Bay! KUL-W11
** 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...
Sugar Beach #306-Ocean view condo located on the beach in N. Kihei, Sleeps 4
This updated one-bedroom, one-bath condo, with central A/C, sleeps up to four people with a king bed in the bedroom and a new queen sofa bed with an upgraded Tempurpedic mattress in the living room. This condo has all of the conveniences of home including a flat-screen...
Amazing 3-bedroom house with AC in Bayview @ Poipu Kai - Ocean View
Our private home offers convenient access to Poipu's best attractions. Located just a short stroll from The Grand Hyatt and Shipwreck Beach, it provides easy access to white sand beaches, fine dining, and local attractions.As part of the exclusive Poipu Kai Resort,...
Designer Studio in Hawaii Kai! Close to beaches, shopping, and hiking!
Come and enjoy this newly updated and professionally designed studio in beautiful Hawaii Kai. This fresh and inviting space is the perfect getaway and launch pad for all of your Hawaii adventures or just to relax and get away from it all.This is a gorgeous, designer...
Beachfront - Parking incl - Oceanview - Waikiki Shore
We can give you a in site parking.***Maxmum is only 2 persons ***COMPACT VEHICLE ONLY (Stall is very small with limited space)Please let us know if you will arrive in the unit after 5pm to 9am. If you would like to check in between the hours of 5pm -9am, we will charge...
Relaxing, Convenient Location In Waikiki!
You'll love waking up to the calming view of the Pacific Ocean in the distance! This beautifully appointed condo is located on the 15th floor of Discovery Bay, offering comfort, convenience, and a perfect home-away-from-home experience in Waikiki. For your convenience,...
NEW KBM Resorts | FREE CAR | Grand Champions | Remodeled 1-Bedroom Villa in the Heart of Wailea! GCH-181
** 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...
Kauai Beach Villas Resort 1 Bedroom with Pool
Escape to paradise in this beautifully appointed 1-bedroom, 1-bathroom condo at Kauai Beach Villas, ideally located on the tranquil east coast of Kauai in Lihue. Whether you're seeking a romantic escape, a solo retreat, or a peaceful base for island adventures, this...
Napili Point | 3 FREE Rental Cars | KBM Resorts | Water Front | 3 Units, 3 Bedrooms | NAP ML-2579
** 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...
(4183) KPalms 4Br 3Ba Spacious Home with AC and Views
Peaceful. Serene. Relaxing. Your Perfect Kauai Getaway Awaits.Escape to your private oasis on the lush North Shore of Kauai in this spacious 4-bedroom, 3-bath vacation home nestled along the scenic old Makai Woods Golf Course (no longer active) in Princeville. With over...
Magic Skies Top Flr Ocean View Under the Sea Room
Enjoy the panoramic views from your large top floor ocean facing room with private bathroom, walk-in shower and walk-in closet and kitchenette. The room has sea life themed decor and custom art and woodwork featuring a wall of ocean facing windows and double doors...
Kaanapali Alii 434
Welcome to Kaanapali Alii 434, a luxurious vacation rental in Maui’s exclusive Kaanapali Alii Resort. This stunning condominium offers a breathtaking view of the Pacific Ocean, surrounded by swaying palm trees and the meticulously maintained grounds of Kaanapali....