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.
Gorgeous Beachfront Condo in Wailea with Private Lanai
*Please note Ekahi Village is a non-smoking community. Smoking is not permitted anywhere on property including patio/lanai, and all communal outdoor areas. Located in beautiful Wailea, the complex is just steps from Keawakapu Beach and walking distance to great...
Ocean Front Luxury Condo - Relaxing Comfort
Kuhio Shores 104 is on the ground floor of this amazing ocean front property. It is very special, perfect for Honeymoon, anniversaries, birthday celebrations, and is also a place where you can completely relax! We are also close to all of the South Shore sites and...
Available 5/6 to 23…..Relax at Maui Eldorado Beach Cabana, Snorkel at Black Rock
Welcome to West Maui! You’ll love this spotless tropical Maui Eldorado Resort condo in heart of the beautiful, world famous Kaanapali Beach. This updated studio has everything you’ll need for a wonderful vacation on Maui! The Maui Eldorado is conveniently located...
Lodge at Kaloko - Kona Cloud Forest Estate with Pool & Hot Tub
🌴 The Lodge at Kaloko – Luxury Estate in KonaPrivate 5BR villa | Pool | Hot tub | Ocean views | Near Kua BayWelcome to The Lodge at Kaloko, a luxury gated estate in the lush Kona Cloud Forest — just 15 minutes from Manini‘owali Beach (Kua Bay), downtown Kona,...
Coconut Coast Oceanview
Enjoy convenience and simplicity from this peaceful and centrally-located retreat. Watch the sunrise over the Pacific from your private lanai , walk to lots of restaurants and shopping at the nearby Coconut Marketplace as well as Longs Drugs, Safeway, Starbucks and...
Hale Lo'i Cottage: Luxury + Convenience in Poipu
This bright, spacious, brand-new 1-bedroom, 1-bath cottage has everything you could possibly need for a flawless vacation—and luxurious perks galore, including an outdoor lava-rock shower. Located in a quiet, upscale neighborhood, this charming tropical hideaway is...
Hale Makau – Luxury Poipu Vacation Home
Welcome to Hale Makau by Gather, a luxury retreat set within an exclusive 10-lot gated community in Poipu. This magnificent five-bedroom, five-and-a-half-bathroom estate offers the perfect blend of modern sophistication and relaxed island living. With sweeping Pacific...
Paradise found-Ocean Front 2 Bdr/Bth/Lanais-Primary bedroom faces ocean FULL A/C
Newly refurnished 2-Bedroom 2-Bath. Can sleep 6 with queen size Aerobed (included). Full size washer and dryer in unit. **Air Conditioning installed in all rooms**.Lae Nani is by far the nicest condominium community on Papaloa Road, which runs from the north side of the...
Enjoy Stunning Views And Outdoor Living At This Elegant Villa
Welcome to Fairways 605 at the Mauna Lani resort. Fairways is a gated community, with lush grounds, a tropical style pool and hot tub. This luxurious townhouse is located in a prime location within the Fairways property and is positioned for ultimate privacy and a 180...
Comfortable and cozy condo
Welcome to our slice of Hawaii paradise! This fully updated and remodeled unit offers a taste of luxury in every corner. From the tiled entrance, kitchen, and bathrooms to the hardwood floors that grace the remaining spaces, you'll find comfort and style throughout.Sink...
New! Top Floor! Spacious Oceanfront Condo with Amazing Lanai and A/C!
Elegantly updated and spacious 2-bedroom 2-bathroom condo that's a wonderful choice for your Kona trip with friends or family!The clean interior design, the open layout, and the cozy high end furnishings are sure to make for a luxurious stay.Enjoy the large covered...
Affordable GEM 1br/1ba w/Tropical Lanai, Steps to Ocean, LOCATION Unit 2
Aloha, and welcome to our newest Paki Maui condo. We are delighted to share our little “peace” of paradise and hope that you will choose to stay in what we like to call, Nasher Hale. Paki Maui is a great oceanfront condominium complex in Honokowai, just northwest of...
Kihei Paradise! 1bed/2baths, 5 mins to beach
*** Note: this property is currently a very successful STR. Starting from April, the management will be changed. This is the reason you don't see any review yet. It's Guest's favorite choice.***Charming 1BR home in South Kihei, across Kamaole Beach Park II. King bed,...
Luxurious 4BR/4BA Presidential Suite AC Near Beach
Welcome to BlueTideVillas! Welcome to Poipu's newest luxury resort-style villas! This is a VERY spacious (2750+ total square feet), top floor villa featuring 4 bedrooms and 3 1/2 bathrooms, with three private lanai's to sit on and enjoy your favorite tropical drink....
Beachfront 1BR 1BA condo on beautiful Poipu Beach Kiahuna #2
New to VRBO!! Relax in your Kiahuna Plantation condo beachfront on the white sand at beautiful Poipu Beach. Building 1 consists of 3 units and is the only ground level building with no second floor, so no one above you. This fabulous property features vaulted ceilings...
Maui's BEST- DIRECT Oceanfront!! Longest Sandy Beach on Maui!!
Welcome to Sugar Beach #228. I invite you to enjoy one of the world's finest beaches - Sugar Beach, with its 5 miles of golden soft sand, warm water and beautiful sunsets. This direct oceanfront condominium has been completely updated with all of the high end finishes...
Loko Kai Nani - Stunning Lagoon Views, Pool, A/C
Welcome to Loko Kai Nani, the Beautiful Lagoon! Look no further. For the Ultimate Big Island Experience. Beats any Hilo Hotel by a mile (IMHO) Fully Air Conditioned, 24 hour security, Everything is Brand New.First time offered, fully renovated with brand new...
4 BR Hawaiian Plantation-Style Home with Pickleball Court
Old Hawaii at its best! Enjoy the updated traditional home nestled within a fully enclosed and private one-acre tropical estate! Chase the keiki (kids) or grandkids on the spacious lawns, or just enjoy the many tropical trees and plants—coconut, banana, mango, ulu...
New Listing- Hale Aka'ula, house of the red sunset
Three bedroom two bath home in the lush sanctuary know as Kohanaiki, this comfortable home is your perfect Hawaiian retreat. Large living room and chef's kitchen are perfect for family gatherings with plenty of windows to enjoy the ocean and sunset views.Tropical...
Amazing views from this ground floor, corner unit steps from the beach!
Enjoy a piece of heaven from this ground floor corner unit with granite counter tops, tile flooring, washer and dryer, and a fully furnished kitchen with everything you need to cook gourmet meals. The condo sleeps 4 comfortably. The master bedroom has a king size bed...
Spacious 2 Bedroom 2 Bathroom City View Condo at the Ilikai Hotel
Experience the beauty of Waikiki with Happy Vacations, a short-term vacation rental company! Our team is excited to offer you a modern condo at the renowned Ilikai. You'll love the open floor plan with lots of natural lighting, a spacious balcony, AC, and thoughtfully...
The Grand Islander, a Hilton Grand Vacations Club - 2 Bedroom Premier - Ocean View
*** Sanitation/Cleaning Update ***We understand that our guests’ expectations for hotel cleaning and disinfecting have changed. That’s why we’ve taken additional measures beyond our industry-leading cleaning standards by partnering with RB, maker of Lysol &...
Luxury Newly Remodeled 3 Bedroom Condo 20 ft from Beach
Come enjoy a stunning and spacious 3-bedroom condo villa at Kahana Village in West Maui, newly renovated and literally 20 feet from the beach, with two walls of glass and an amazing corner ocean view as well as a huge ocean front lanai.This beautiful private beach house...
𝐅𝐢𝐧𝐝𝐢𝐧𝐠𝐌𝐞𝐢𝐥𝐢 GorgeousBeachfront KoOlina Resort+Amenities.STUDIOsuite
𝐕𝐢𝐬𝐢𝐭 𝐅𝐢𝐧𝐝𝐢𝐧𝐠 𝐌𝐞𝐢𝐥𝐢 to enjoy 𝐄𝐱𝐜𝐥𝐮𝐬𝐢𝐯𝐞 𝐒𝐚𝐯𝐢𝐧𝐠𝐬 on this stylish 𝐒𝐭𝐮𝐝𝐢𝐨 𝐒𝐮𝐢𝐭𝐞 at the stunning 𝐌𝐚𝐫𝐫𝐢𝐨𝐭𝐭’𝐬...
Just Across The Street From The Ocean And Beach. 2 Bed 2 Bath Great Location
This condo has 2 bedrooms 2 Full Bath with a open floor plan in the Living room, Dinning room and Kitchen. You are looking at a lovely and functionally designed 2bd/2ba condominium situated on the third floor of a building. An elevator is provided.The SpaceAre you sick...
Serenity in South Kihei – Maui Kamaole I215, Your Ideal Island Escape!
Maui Kamaole #I-215Welcome to Maui Kamaole #I-215, a fully remodeled 2-bedroom, 2-bathroom condo nestled in the quiet, tropical hillside of South Kihei. This stylish and spacious upper-level retreat is perfect for couples, families, or friends seeking comfort, privacy,...
Maui Resort Rentals: Honua Kai Konea 404 – Upgraded 2BR w/ Partial Ocean & Mountain Views!
Konea 404 is an upgraded two-bedroom suite that offers guests the best of both worlds. Enjoy beautiful partial ocean views, as well as stunning views of the West Maui Mountains, right from the comfort of your spacious lanai (balcony).As the very first two-bedroom back...
Luxury Gated private acre , Beach front Rental,with pool,spa,sauna ,and more
TVNC #4224This one of a kind tropical gated oceanfront Luxury Estate offers the ultimate in beachfront island living and privacy on over an acre . With breathtaking ocean views and lush scent filled landscaping. The attention to detail is uncompromising inside and out....
Recent RENO! Fits 6, FREE parking
You & your family or friends will be close to everything at this centrally-located oasis in Waikiki. A couple minutes to the beach, surfing, the lagoon, boating & fishing, hiking, restaurants of every kind, shopping galore, everything Hawaii has to offer for a tropical...
Amazing Ocean Front at Sugar Beach Resort #519, High End Remodel, 1Bed/1Bath
Sugar Beach Resort is located north of downtown Kihei on beautiful Sugar Beach. Sugar Beach stretches for miles on Maui's Maalaea Bay. Stay in our Hawaiian condo and it will be a vacation you will never forget. Sugar Beach Resort is just a 15 minute drive from Maui's...
Renovated 1 Bedroom W/ Stunning Views, Parking, & Central Air
If you've been imagining the perfect place to enjoy your upcoming Waikiki getaway, look no further! Expansive Ocean and Park views, private lanai, central air conditioning, covered parking and rooftop pool and saunas check all the boxes and make this newly renovated,...
Kauai Exclusive - Pane Makai Turtle Suite - Steps to the Beach!
With ample room and durable bamboo decor, this plantation-style beach suite is perfect for large groups, wedding parties and family reunions. Comfortably sleeping 7, look no further for the perfect gathering place for friends and loved ones! This 3000 square foot suite...
Beach Glam @ Turtle Bay - Kuilima Estates West
We are all looking for a quiet, restful, safe place to de-stress and forget the troubles of the world. As a Hawaii born and raised local, there are few places that can rival this task than the North Shore on Oahu. With 24 hr security, free parking, and the Turtle Bay...
Wailea Ekahi Village 35C - 1 Bedroom Garden View Condo
Wailea Ekahi 35C is a stunning vacation rental located in the desirable Wailea community. This beautifully appointed one-bedroom, one-bathroom condo offers an ideal blend of comfort and luxury. Make use of the ground floor location to really live an indoor/outdoor...
PACSA304 Newly Updated 2BD Condo w AC Near Kamaole Beach
Pacific Shores A304 2Bedroom Condo Across the Street From Kamaole Beach. Walking Distance to Restaurants, Shops, Beach Activities FREE daily activities included with your stay value up to $554! Complimentary admission, every day of your stay*: Whale Watching (seasonal),...
Princeville Palms Manor - Hanalei Bay
Locally-crafted Décor, Spacious Chambers, with Natural Wood Trim. Beautiful Two-Story Air-Conditioned Retreat …serenaded in the song of jungle birds!Meticulously thought-out kitchen, accessories, games and endless amenities. For our eco-conscious guests, we've...
Sunset View-Ocean Front - East Honolulu - Cottage Charmer!
Enjoy the perpetually calm span of crystalline ocean and the gentle trade winds as you relax on the oceanfront lanai or sun deck of this beautiful home tucked onto Oahu's south shore. Launch a kayak or stand up paddle board from the private dock or relax on the large...
Hale Hau`oli ~ FAIRWAYS TERRACE H104 ~ 2 BR / 2 BA ~ Pool/Spa/BBQ ~ Gym ~
Summary:Hale Hau'oli - Located on the western slope of Mauna Kea our 2 bedroom 2 bath condo in Waikoloa Village sits on the Robert Trent Jones golf course (The Village Course). Enjoy the benefits of the 900’ elevation with warm days and cool mornings and evenings....
Maui Westside Presents - Eldorado H208
🌺 Aloha from Maui Eldorado H208! 🌺Winter Special - Book 7 nights and receive a 10% length of stay discount. Rates are updated automatically and applied when selecting 7 nights or more. Escape to your dream Maui getaway in this fully renovated, 1,440 sq ft,...
BABY BEACH BUNGALOW 2-STEPS TO BEACH - OCEAN VIEW - AMAZING LOCATION, NEAR SHOPS
POIPU-- Kauai-- Vacation Home Rental-- Ho'ona Road-- Baby Beach Bungalow 2 is steps away from a crescent-shaped white sand beach called Baby Beach and is located in a family-friendly neighborhood on Ho'ona Road. We Do Not have A/c, all rooms have powerful ceiling fans...
#17 Large 1/1 Condo | 1 Bed, 1 Bath
Aloha! This is truly a special and unique part of the world. Condo #17, Hale Maluhia (House of Peace), sits OCEANFRONT on the Sea Mountain Resort at Punalu'u Black Sand Beach. It is a spacious separate one-bedroom unit, built in the 'Kama'aina' (Hawaiian bungalow)...
Serene Luxury Golf & Tennis Villa - outdoor pools, hot tub, bbq
Wailea Grand Champions Villas are the perfect place for vacation. Set amid Wailea’s Blue Golf Course and adjoining Wailea Tennis Club, this property is ideal to rest from everything Maui has to offer for your discovery. Within minutes of both driving and walking,...
Waikoloa Beach retreat! Top floor, walk to beach+shopping+golf, saltwater pool
Welcome to our happy place, Vista Waikoloa D301! Centrally located in Waikoloa Beach Resort on the Big Island, your condo features:- Spacious 350 sq ft. wrap-around lanai (with peek-a-boo views of Anaeho'omalu Bay)- Gorgeous views of Mauna Loa and Hualalai- Walk to...
The Most Gorgeous OV Villa in Kapalua Sleeps 6
THE BEST LOCATION ON MAUI, ALSO, THE BEST LOCATION IN THE COMPLEX!!! THIS IS PARADISE!!! Enjoy beautiful ocean and sunset views. I was just there and from my lanai, we watched whales breaching. You will love our great views of the ocean, golf course and the island of...
Updated oceanfront gem @ Sugar Beach Resort, Central AC, NO Booking fees!n
Welcome to Sugar Beach 518. This updated oceanfront 1 bedroom, 1 bathroom condo can accommodate 4 people. Enjoy ocean views throughout this unit and from your private lanai. Feel right at home with everything from central AC to in unit washer/dryer, and essentials....
Aloha Hale - 3-bedroom house in tropical Pāhoa near Hilo
Your group will be close to everything when you stay at this centrally-located home near Pahoa Town where you'll find local shops, a variety of restaurants, and the gateway to exploring the Puna District. The 3 bedroom 2 bath home is located in a quiet Hawaiian...
Great Rates! Intimate Ocean/Beach Condo, Couple's Paradise!
new flooring, walk in shower, new vanity, new kitchen cabinets countertops, appliances,fresh paint quiet concrete building with high ceilingslarge 1 bedroom unit 799 sq ftmeticulous grounds with lots of Hawaiian plantsbbq pool hot tuba true sliver of paradise!
Modern Spacious Beachfront Luxury in Wailea. Family Friendly!
A modern 2 bedroom, 2 bath condo with extra bunk beds and an amazing ocean view!South Maui is one of the most beautiful destinations in all of Maui and Wailea Ekahi Village is a perfectly situated, beachside resort we call home. Guests return to Ekahi year after year to...
Convenience & Comfort, A minute walk to Hanalei bay and short stroll to town!
Note: Our transient vacation home is located in a Tsunami Evacuation Zone. In an event of a Tidal Wave, evacuate to higher grounds. We also incur occasional bridge closer due to flooding of Hanalei roads. Access to our vacation home may be limited to all local traffic....
#605 Top Floor Unobstructed Ocean View/Sunsets, New quiet A.C.
Island Surf #605 Condo Description:JUNE UPDATE: New central AC was just installed ! Incredibly quiet !! Individual room climate control. Aloha! We are excited to share our condo with you for your beautiful trip to Maui and we would like to make your vacation as...