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.
3 Bedroom Penthouse W/Private Lanai–Poipu Shores
Nestled along the shoreline, this serene haven offers sweeping ocean vistas and mesmerizing sunset displays that will leave you in awe. Step inside this stunning oceanfront penthouse, where breathtaking ocean views of the Pacific Ocean welcome you home. Designed with...
This beautiful beachfront Hanalei Bay home is located steps from the sand
This beautiful beachfront Hanalei Bay home is located steps from the sand on Kauai's majestic north shore. It offers panoramic views of an iconic beach and its surrounding mountains within a quick walk to the Hanalei Pier for surfing and swimming and the Hanalei River...
Trade Winds Plateau
Located on a private, gated road, experience fresh air that's travelled thousands of miles over the ocean. Explore 15 acres of the most beautiful property in the universe. Be prepared for 50,000 shades of verdant green to welcome you to a beautiful oasis of privacy....
Spacious Home Near a Quiet Beach
Our lovely 2 bedroom surprises most guests with how spacious the rental is with expansive floor plan and the access to a yard to enjoy.The rental comes with a brand new kitchen with a very open design and lovely countertop to enjoy meal prep and dining. The large teak...
Sunny Family Oasis ☀ Tree House, Trampoline, Games, Toys
Single family residence with front and back yard. Wonderful trade winds keep the house cool and fresh year round. Relax on either of the front or back lanais. The house is stocked with all the necessities for the best possible stay in Princeville, Kauai. You will have...
Fully renovated & customized condo with lanai, pool, hot tub, tennis, central AC
Shores at Waikoloa Bungalow 225Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Newly renovated and beautifully customized from top to bottom, this elegant, two-bedroom condo is full...
Kailua Beachfront Vacation Home with Pool
This property is professionally managed by Private Homes Hawaii, LLC and is licensed as a short term vacation rental, Non-Conforming Use Permit Number 1990/NUC-1783. It is compliant with Hawaii State Legislation (HB2078) for vacation rental accommodations,...
Hale Kupanaha – Mid-Century Modern Luxury in Poipu
“This house is amazing!” visitors often exclaim, in those exact words. Hence, the property’s poetic and perfectly apt Hawaiian name: Hale Kupanaha (“Amazing House”). The design team behind this extraordinarily gorgeous new villa envisioned a distinctive aesthetic:...
La Bella’s Bed & Breakfast-Honu (Turtle) Suite-Walk to beach-In Kailua (O’ahu)
No detail is overlooked at this charming and luxurious home. La Bella’s Bed and Breakfast is the place to be if you are looking for a short walk to the beach, a beautiful garden to enjoy, great host family and close to amenities. Our luxury bedding and upgraded style...
Hawi Hideaway, quiet home in small country town
Welcome to Hawi Hideaway,2 bedroom, 1 bath home in Hawi. Sleeps 6, walking distance to main street, Saturday farmers market, coffee shop, boutique stores and galleries. Our home is tucked away off the street in a beautifully landscaped yard. There is a mango and orange...
Fabulous Home Overlooking Hilo Bay and Kawainui Falls
Pepeekeo is waiting for you at this 3-bedroom farmhouse. Nestled in a tranquil setting, this gorgeous property offers an amazing retreat for guests. The bedrooms feature a comfortable king bed, a luxurious queen bed and a cozy bunk bed. With 2 full bathrooms, including...
Family-friendly Waikoloa Beach Villa C2 next to pool; walk to beach!
Welcome to our island home-away-from-home! The Big Island is a truly special place with something for everyone – from beaches to walks and hikes to water activities, golf, shopping, and sight-seeing.Waikoloa Beach Villas is adjacent to the Queens and Kings Shops for...
Luxury Condo with AC, Large Pool, Golf Course, Gym
Same listing as https://airbnb.com/h/pilimai5j. The new Pili Mai Resort is an open-skied sanctuary within the popular town of Poipu. The luxury condo comes with 3 bedrooms, 3 full bathrooms, office workspace and spacious lanai to enjoy the beautiful garden view with...
Modern and Relaxing Oceanfront Vistas
Summary:Bright, modern, and spacious. Complete remodel in May 2022! Thoughtfully designed to elevate your experience with us. This one-bedroom, one-bathroom condo features luxurious touches throughout paired with beautiful ocean views. Located in the sunny and vibrant...
Hawaiian-inspired studio with ocean view
Papakea B307 is a Studio condo featuring amenities such as a stunning ocean view, a washer/dryer, and air-conditioning! The condo can accommodate up to 4 guests with a Queen-size Murphy bed. The spacious main living area includes modern furniture with tile flooring and...
One of the Most Beautiful Ocean Views in West Maui at Kaleialoha
Gorgeously and recently renovated unit at Kaliealoha tucked in the corner to avail of the amazing ocean views West Maui has to offer. It’s arguably the best unit at Kaleialoha. Entire left wall has tinted widows for privacy, feels like your outside with nature. The unit...
Kona Isle D2 DIRECT OCEANFRONT, Best View!
Updated kitchen and bathroom! D2 at the Kona Isle is a beautiful DIRECT OCEANFRONT property on the 1st floor of building D! No stairs! Cook in the full kitchen or on the grill! Enjoy dinner with a sunset view from your living room, lanai, or picnic tables! Feel the...
Mokihana House Kauai - 5-bedroom House with Mountain Views, Pool, Tennis and AC
It's the perfect time to discover the beautiful Island of Kauai where you can surf, snorkel or paddleboard at the world-famous Hanalei Bay (always ranked top 3 beaches in the world) and hike along the Napali Coast! The Mokihana House has everything: air-conditioning,...
Panoramic Views - Fourth Row Ho'olei - One of a Kind 112-4
Newly Remodeled in 2023! Come relax and enjoy the spectacular ocean and island views in this rare three bedroom condo perched on the very top row fourth tier in the Ho’olei community.This spacious unit has 3 bedrooms, 3.5 bathrooms, a large living room, fully equipped...
Beautiful Home With Spectacular Amenities
Our large and sun-filled condo has plenty of space for a large family and lifelong memories. We are part of the Hali'i Kai community. Enjoy the Hawaii vacation you've dreamed of in the gated community of Hali'i Kai.Our 3-bedroom, 3-bathroom two-story condo offers guests...
Charming Home in Mountain View
Newly remodeled home on a two acre property will provide you a real taste of big island living. Peaceful and relaxing environment. Fresh mountain air. Magnificent native foliage. Comfortable cool climate.Explore the island by kayaking in Hilo Bay. Complimentary rental...
Spacious 2 Bdrm Remodeled Oceanfront 01 unit
Above and beyond any other unit. Stunningly large with separate 2 Bdrms. Newly remodeled oceanfront condo on the Gold Coast. This is definitely the quiet end of the building and with the additional windows on the mountain side, you get incredible cross breezes all year....
Brand New 2 Bedroom House
Experience local-style living in the cool, quiet, and tranquil Pupukea. This brand new house is a perfect place to relax.Enjoy a private entrance and free parking. 5 minutes from Waimea Bay and other famous surf spots.Family-friendly, ideal for 4 people with the option...
14FL 3 Bedroom 2 Bath + Free Parking + Partial Ocean View, 2 min from the beach
Legal vacation rental at a fabulous location by [SUPER HOST]! This renovated 930 sq ft, 3 bedroom 2 bath with 2 balcony home is across from ‘Alohilani Resort, Steps away from the Waikiki Strip (Kalakaua Ave) and Waikiki beach! There are endless shopping, dinning, and...
Papakea H304 2BR / 2BA Condo with Spectacular Ocean Views & Central AC
The Papakea is a Kaanapali Beach Oceanfront Resort. Unit H304 is a 2 bedroom, 2 bathroom condo with Central A/C, Ocean Views from both the Lanai and Master bedroom, sleeping 5 *** Completely Renovated - new furniture, flooring, kitchen, appliances, central air...
Comfortable, single-level retreat with fast WiFi & washer/dryer - dog-friendly
Puni Mauka A | 31-Day MinimumOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Located less than five miles from Pāhoa for convenient shopping and dining and just two-and-a-half miles...
Blue Hawaii - Top Floor Lae Nani 334 - Beachfront Condo with AC & WD
Enjoy the best that Kauai has to offer from the comfort of your own top floor Wailua Bay condo! Fall asleep and wake to the sound of the ocean in your king bed and enjoy the oceanfront view from your private 3rd floor deck. This is one of the few units at Lae Nani that...
Keauhou Punahele #B108: Grnd-floor 2-bed, 2-bath + garden views and outdoor BBQ
Keauhou Punahele #B108 is an excellent location for relaxation, close to Keauhou Bay and the shopping center. Enjoy this two-bedroom, two-bathroom, ground-floor unit. Relax on the large lanai with a barbecue grill, outdoor seating, and garden views.You will be greeted...
Maui Resort Rentals: Honua Kai Hokulani 526 - 1BR Suite w/ Lush West Maui Mountain Views
Hokulani 526 is a luxurious 5th-floor one-bedroom suite that offers beautiful vistas of The West Maui Mountains with their frequent afternoon rainbows. The suite is ideally suited for small families and couples who are looking for luxurious and spacious accommodations...
ALOHA - Poipu Beach Vacation Condo
Aloha! This charming, cottage-style condo is located at the 35-acre Kiahuna Resort next to Poipu Beach, Kauai's beautiful South Shore. The Resort is beautifully landscaped with rolling lawns, Koi ponds, the famous Moir Gardens, and has its very own world class sandy...
Gorgeously Updated - Kihei Surfside #113 - Groundlevel Oceanfront Condo
Kihei Surfside #113 – Fully Renovated Ground-Floor Ocean View Condo with A/CEnjoy comfort, convenience, and coastal beauty at Kihei Surfside #113—an ocean view, ground-floor condo that underwent a complete renovation in May 2022. Located steps from the water’s edge and...
Waikiki Sunset Hotel remodeled unit with a magnificent view of the Koʻolau Range
**Looking for additional accommodations, please view my other unit located in the same building #2773517**Located on a high floor of the Waikiki Sunset with majestic Koolau mountain, golf course and city views. This condo offers enough beds to sleeps 6: 1 bedroom (king...
Beautiful Oceanfront Ohana: Spectacular Views, Pool, A/C, Best Beach&WOW Sunsets
Aloha and Welcome to our Maui Ohana!Relax and recharge at this tropical retreat, perfectly situated within a short walk to Wailea in the Kihei Surfside Resort. Boasting stunning ocean views, direct access to Maui’s best beach, Keawakapu, and a sprawling lawn with a...
Maui Sunset B112 Ground floor one bedroom
Ground floor means easy access to tropical gardens and the ocean beyond. Quiet location features large private view deck and renovated interior. New Flooring throughout 2023. Doesn't get any better. Large private condominium apartment at the resort condominium complex...
40th Floor One Bedroom Condo
Newly developed and completed in Fall 2021, Azure Ala Moana makes the perfect home away from home. Perfect for long term stays- you'll have a spacious full kitchen with dishwasher, full size oven, and a washer and dryer in the condo, and a beautiful view of Sunset....
Makaha Shores Beach Front Ocean View Studio W/ AC
Makaha is a small town located on Oahu's West shore. 30 miles, 45 min from Honolulu Airport. The towns main attraction is its family friendly pristine and sandy beach. Makaha offers the best diving, snorkeling and surfing on the island. Our 5th floor gem beckons and...
Maui Resort Rentals: Honua Kai Konea 305 – Spacious Interior Courtyard 2BR w/ Partial Ocean Views!
Konea 305 is a luxurious 3rd-floor interior courtyard two-bedroom suite boasting beautiful views of the blue Pacific Ocean and the lush Konea pools and courtyard.Gather, reconnect, and celebrate this expansive two-bedroom floor plan. Konea 305 offers a spacious 1300+ sq...
Maui Resort Rentals: Honua Kai Hokulani 715 - Stunning 7th Floor Ocean View 2BR w/ Deluxe Corner Floor Plan!
Widely regarded as the premier two bedroom floor plan at Honua Kai, this 7th-floor oversized 2BR deluxe ocean view corner suite boasts a 1325 sq. ft. interior with direct ocean views from the kitchen, dining room, and living area, as well as the 340 sq. ft. wraparound...
Poipu Sands 437: Updated Spacious 2BR Ocean View Condo, A/C, pool, tennis, beach
Welcome to Poipu Sands 437! This top floor ocean view condo is spacious, updated and comfortable, with a 300+ sq ft lanai overlooking the cliffs of Shipwreck Beach, perfect for turtle, dolphin and whale watching (in season). There are two bedrooms, two bathrooms, a...
Wai'ula'ula A202 - Upcountry Residence
This upper-level, ‘upcountry’, oceanview residence offers a great room with sliding glass pocket doors for indoor/outdoor island living, a handsome kitchen outfitted with premium appliances and granite countertops, as well as a dining table for six. Additional features...
New 2 Bedroom Guesthouse with Mountain & Ocean View!
This comfy, stylish guesthouse is located near Kealakekua Bay and the Captain Cook Monument. Here you can enjoy snorkeling, hiking, kayaking, boat tours and scuba diving. Our Guesthouse offers 2 bedrooms with queen beds, a full-size kitchen, lanai, laundry room and BBQ...
Remodeled 1BD/2BA in Best South Kihei Location, split A/C, 3 min from the beach!
Aloha and welcome to Tranquil Turtle Retreat at Maui Banyan! Our recently remodeled owner-managed condo is located right in the heart of South Kihei close to world-class beaches, shopping and amazing restaurants. We have thought through all the details to make your...
Hawaiian*Elegance*FULLY REMODELED OCEANVIEW 2 Bdrm
Indulge in the epitome of Hawaiian luxury within this impeccably renovated condominium. Immerse yourself in the tasteful Hawaiian decor that effortlessly transports you to paradise. The well-appointed interior boasts high-end furnishings and comprehensive amenities for...
Waipouli Beach Resort E301 2 Bdm, 3 Bath - Beautiful Sleeping Giant Mtn View
Waipouli Beach Resort E301 2 Bdm, 3 Bath - Beautiful Sleeping Giant Mtn View and Peek Oceanview!SLEEPS UP TO 7! This Luxury Condo Offers Guests a Gorgeous View of Sleeping Giant Mountain and peek ocean view from the lanai. This Condo is a 2 Bedroom, 3 Bathroom Condo at...
Oceanfront New House on Kealakekua Bay
*We are only accepting 31+ day reservations*With construction completed during the Summer of 2020, be one of the first to enjoy the open design and simple elegance of the Dolphin House. This oceanfront house has 3 bedrooms with en-suite bathrooms. Each bedroom opens up...
Maui Kamaole A205 Remodeled with spectacular Ocean Views
Stunning ocean views from this spacious Maui retreat at the popular Maui Kamaole in South Kihei. This two-bedroom condo is amongst 14 of the largest floor plans at 1,224 square feet, and features high ceilings and lots of room to entertain. The fully equipped kitchen is...
Luxe Beachfront Tropical Paradise
30+ 5 Star "Awesome" "Beautiful" "Bliss" Reviews and Counting! Please plan ahead as our calendar fills up quickly.THE AMBIENCEIf thoughts of azure oceans, romantic getaways and sunrise mornings are just some of the peaceful images that make you happy, then this is the...
OCEAN and POOL View, remodeled 2 bdrm condo with A/C - PAPAKEA K406
Stunning Ocean and pool view Papakea 2 bedroom / 2 bathNewly remodeled throughout & new furnishings2 beautiful swimming pools, 2 ocean side cabanas, jetted spaPool side BBQs3 tennis/pickle ball courts & 2 putting greensWalking distance to stores and restaurantsShuffle...
Spectacular Oceanfront GEM!
Brand new fully remodeled Lahaina Gem! This stunning 2 bedroom 1 bath condo is where it’s at! Get the feel of old hawaii with a classy modern twist. We also provide snorkeling gear, body boards, beach chairs, beach towels, and new air conditioning. The Condo is ground...
Makaha's Hidden Gem by Kalo Homes
Escape to paradise in this beautiful vacation home located in Makaha Valley. Enjoy stunning panoramic ocean views and relax in the tropical backyard. Inside, you`ll find a fully equipped kitchen, comfortable furnishings, and ample space for your group. Take a short...