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.
Kaanapali Alii | 381
The color blue is known to evoke a sense of calmness, serenity, and comfort. What more could you ask for on a vacation! When staying in condo 381 at the Kaanapali Alii, you will be subtly surrounded by the color blue. From your living room, kitchen, dining room, and...
Wailea Grand Champions | 43
Wailea Grand Champions 43 is a stunning vacation rental nestled in the heart of Wailea, offering a luxurious escape with breathtaking views and unparalleled comfort. This elegantly designed property is ideal for those seeking both relaxation and adventure on the...
Hale Kamaole 176 Ground floor condo, easy access to best beach on Maui!
This Modern, Maui Vacation Rental unit #176, has it all. The owner of this condo also owns unit 174, both of which have been completely remodeled from top to bottom recently. Occupancy of these units is limited to only 2 adults. Ocean & garden views from the well...
Wailea Ekahi Village | 38F
Nestled in the heart of Wailea, Wailea Ekahi 38F is an exquisite vacation rental that offers a luxurious and serene Maui escape. This stunning two-bedroom, two-bathroom condo takes full advantage of its second floor positioning and boasts panoramic ocean views. Take...
Maui Tropical Paradise - Vacation Home In Haiku - Pool/Spa
This lovely 3 bedroom, 2 bath plantation style home is located in the heart of Haiku. It has an open floor plan, vaulted ceilings and windows all around. You will enjoy lots of light and views of the lush garden, pool and spa. With high quality beds, a fully equipped...
Wailea Ekahi 1B Recently Remodeled Ocean View 1st Floor Luxury 1BD 2BA Condo
Unit 1B is located on beautiful Keawakapu Beach in gorgeous Wailea. This totally remodeled lower village, ground floor unit has one large lanai with a beautiful ocean view and Ekahi’s 34 acre tropical landscaped gardens. It has a lanai table that seats 6. It is...
Keauhou Kona Surf & Racquet 188: Renovated Oceanfront Retreat
Welcome to Keauhou Kona Surf & Racquet 188 by Gather, a fully renovated two-bedroom, two-bathroom, Air conditioned oceanfront townhome in Kailua-Kona, Hawai'i. This two-story duplex accommodates up to six guests and offers panoramic 180° ocean views from nearly every...
Poipu Oasis - Poipu Vacation Home with Pool
Poipu Oasis is a beautiful custom home with ocean views, just up from Poipu Beach park. This lovely two-story home's indoor outdoor living floor plan is designed to take full advantage of Poipu's views. The private pool is surrounded by a lush yard, the perfect place to...
Palm Villas at Mauna Lani B1, Spacious 3BR condo with Private Beach Club Access
PLEASE NOTE: POOL WILL BE CLOSED FOR REPAIRS FROM SEPTEMBER 8 - OCTOBER 4, 2025.Ready to escape to paradise with comfort, style & the Aloha Spirit? Just a 15 minute walk to the beach, The Palm Villas is located within the beautifully kept grounds of the Mauna Lani...
Maui Breeze Retreat at Ho'olei openings Jul 19-29, Aug 22-Sep 14 & Sep 25-Oct 11
Surround yourself with the lush scenery of Maui Breeze Retreat at Ho'ol!ei, a tastefully decorated two-story villa with spectacular views of the Pacific Ocean. Your exquisite island retreat in Wailea offers spacious, well-appointed living quarters embraced by manicured...
Updated Kauhale Makai unit 610 1 bedroom top floor, king bed, AC
• Oceanfront• Central A/C unit• King bed• Remolded May2023• Beach access from condo complexWelcome to our home at Kauhale Makai 610. Our home was updated in May of 2023. Our beautiful and pristine one-bedroom condo sits on the top (sixth floor) of the complex....
Hapuna Beach Residence B25 at Mauna Kea Resort
Enjoy unobstructed beachfront views in this modern, luxurious two-bedroom unit decorated with Restoration Hardware furniture throughout. Overlooking the white sandy beach, the living and master bedrooms feature floor-to-ceiling sliding glass walls that open to create an...
The "Promise Tree" - Great Family Gathering Place in Kailua Kona!
Please only book through VRBO or a reputable site!Experience the exquisite natural beauty of the Big Island. This beautiful custom home built in 2014 is located in an extremely quiet community 5 minutes from downtown Kailua-Kona. There are spectacular views of both the...
Maui Banyan G202 - King Bed, Ocean View, Across from Kamaole Beach
This unit is located in South Kihei, which is on the southwest side of Maui, an easy drive to nearly all of Maui’s landmarks and outdoor activities. Kamaole II Beach is right across the street from the Resort and offers excellent swimming, snorkeling, white sand and...
Poolside Tropical Paradise Oasis
Escape to paradise and indulge in the serene ambiance of Maui Kamaole M-101, a sparkling clean condo conveniently located right next to the pool and just steps away from the stunning Kamaole III Beach. Featuring two tranquil garden patio lanais, including a completely...
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...
Kona Garden Studio Ohana, private sunset lanai & seasonal fruit from the garden!
Take a break and unwind at this peaceful oasis. Enjoy beautiful views of the Kona coast from your private lanai, with plenty of fruits and herbs in the garden for your enjoyment. Depending on the season enjoy fresh papaya, mango, citrus, pineapples, figs, ulu, and...
MINUTES TO HAMOA BEACH, BEST LOCATION IN HANA
Maui County Permit # STHA 2016/0006Tax ID TA and GE 170-361-2416-01SUPER CHARMING - Hawaiian Vintage styled Cottage..Close to beaches and natural pool. Fully upgraded with lots of amenities. All new comfy furniture to kick back and watch a movie.Free high speed wireless...
Oceanfront Condo- Gorgeous Ocean Views! Sleeps 4
Aloha and welcome to Hale Ono Loa 303! Hale ono loa means "house of good living" in the Hawaiian language, and that's exactly what you'll find in our condo! Between breathtaking views, a comfortable king sized bed, and a communal pool amongst countless other amenities,...
Crown Jewel of the Coconut Coast - Waipouli B401
Experience ultimate relaxation in this tranquil, top-floor penthouse suite at Kauai's Waipouli Beach Resort & Spa. This luxurious ocean-view haven boasts two King Size Master bedrooms, each with its own lavish 3/4 Master bath adorned with elegant Indonesian woods and...
Kamoale Sands 9-410! Favorite locale near everything and ocean views!!
Kamaole Sands 9-410 is centrally located, offering a 2 bed / 2 bathroom unit, perfect for your Maui Vacation! It's just across from a large beach park and Kam III beach, providing stunning views of the ocean and West Maui Mountains.This spacious unit features vaulted...
ATOMIC TIKI – live like a local at Magic Sands Beach!
Vintage Hawaiian Oceanfront ParadisePop back in time and relax in 60's mod style in this quaint vintage apartment hotel, capturing a front row center view of Magic Sands Beach since 1963.Roll out of the soft and cozy queen size bed and step right across the street to...
This building has BEST PANORAMIC OCEAN VIEWS in Complex ~ VERY NICE Renovation Inside
Aloha future guests! All properties in our ohana or family have Hawaiian names. We call this Kapalua Golf Villa, Hale O Alihilani', which means 'home where the ocean meets the sky'.JUST LIKE IN THE PICTURES, QUALITY RENOVATION, FABULOUS OCEAN VIEWS!Centrally located on...
Maui Resort Rentals: Hokulani 605 – Premier 6th-Floor Oceanview Penthouse | Closest 2BR Column to the Ocean!
Maui Resort Rentals is proud to bring you this 2BR Premier Oceanview Suite at the Honua Kai Resort, newly launched and available for bookings starting August 29th, 2025!Boasting a premier top-floor location in the closest two-bedroom column to the ocean at the resort,...
April 26-May 3rd! Sleep 10 Poipu House at Makalea A/C, Private Pool & Hot Tub!
Discover your own slice of paradise at the Poipu House at Makalea, a beautifully crafted estate home offering luxury, space, and serenity on Kauaʻi’s sunny South Shore. With 2,700 square feet of thoughtfully designed living space, this elegant four-bedroom,...
Secluded Oceanfront Cottage- in Princeville – Private large Spa & Stunning Views
For less than half the price of a standard hotel room, this private ocean bluff Cottage-Studio offers a luxurious and romantic experience—giving you more space, more privacy, and more of Kauai’s magic. Instead of a crowded resort, you’ll wake up to the sound of...
Kailua-Kona Luxury Vacation Home – Ultra Private Oceanfront Gated Estate
This oceanfront residence is a gated estate situated in a private neighborhood off of Kailua-Kona’s scenic Ali’i Drive, just 5 minutes from town. Recently remodeled, this home reflects a true sense of place with Hawaii-style architecture, expansive indoor-outdoor...
Maui Paradise: Steps to Sand & Sun. Blg#1-Ocean View, AC's, Fast Wifi, 1st Floor
Come enjoy ocean views, sunsets, and sounds of waterfalls in our newly updated one-bedroom (King Size Bed), two-bath, air-conditioned condo. Kamaole Sands is just across the street from one of Maui’s best beaches. – Kamaole Sands Resort is a heavily sought-after...
Modern, Designer Owned 2BD+2BA w/ Loft @ Kuilima Estates West
Experience this spacious, clean & comfortable, newly remodeled unique 2-story townhouse with the conveniences of a home which is fully air-conditioned w/ new quiet Mitsubishi split system a/c. This is especially important for the hot and humid days. There is no unit...
Lanikea at Waikiki - Luxury 2BR Suite Ocean & Park View
This 2 bedroom unit comes with 1 California king-sized bed, 1 queen-sized bed, and 1 sofa bed, and can accommodate maximum of 6 people. The unit is equipped with a full kitchen with cookwares and utensils. A brilliant view of the ocean and park from the living room and...
North shore Maui ocean view B and B room 3
North shore Maui ocean view B and B is a vacation rental with three bedrooms for rent individually on Maui's north shore. Each room has a private bathroom, ac, tv, and Wifi. Room 3 is the only room on the top floor of the house. The rest of the house, the entrance,...
Wai'ula'ula 415 - Lavish Oceanview Residence
This magnificent, ‘upcountry’, oceanview residence offers a great room with sliding glass pocket doors for indoor/outdoor island living, a chef’s kitchen with natural stone countertops and top-tier stainless steel appliances, including a gas range and wine...
Your Island paradise!! Home Away From Home 3 Bedroom 2 1/2 Bath Luxury Villa
Your Island Paradise Awaits You! Feel right at home in our spacious 1700 square foot, 3 bedroom, 2 1/2 bath Villa with an attached garage. This beautifully decorated Villa is just steps away from the resort style pool featuring a lava rock waterfall, Jacuzzi spa, and 4...
Mauna Lani Point | E203
Mauna Lani Point E203 is a luxurious vacation rental located in one of the most prestigious clusters of the Mauna Lani Resort, with direct views of the golf course's signature hole. This oceanfront condo offers a stunning blend of comfort and elegance, making it an...
Beautiful Townhome with Exquisite Furnishings. Garage available for guest use.
Enjoy your vacation at this Ali'i Cove townhome. Decorated in an elegant island style, this 3 bed, 3 bath end unit is designed for comfort and ease. Located on Ali'i Drive, Ali'i Cove is conveniently near shops, restaurants, and activities in downtown Kailua Kona. This...
BRAND NEW LISTING DISCOUNT-Amazing Ocean Views-heated pool-location-AC
Spacious & Updated 3rd Floor Condo with Ocean Views and Vibes Welcome to your home away from home at Royal Kahana, Unit 312, located in Kahana, MauiA beautifully refreshed condo designed for comfort, convenience, and relaxation.Inside the Condo:Private balcony on the...
Tropical Bamboo Retreat in Upcountry Maui!nBamboo Heaven Maui LLCnBBPH 2012/0003
Consider this bed & breakfast your home away from home while you visit Haiku Maui! This tropical property offers a peaceful retreat in the country with fruit trees, rainbows, and night skies filled with stars and galaxies! My unique bamboo home welcomes you to unwind...
Gorgeous Remodeled hotel suite in Princeville w/ pools & beach access, sleeps 4
Unwind in Princeville at this lovely hotel suite! Enjoy the modern comforts of this remodeled unit with A/C, a comfortable king-sized bed, 50" TV, sofa with a queen-sized pull-out bed, and a private lanai with a beautiful view of the north Kauai Mountains made famous by...
Exquisite Oceanview Villa with Resort Amenities in Gated Community
This property is hotel zoned, and not being affected by the recent proposed legislation.Located in highly desirable secluded area of neighborhood your villa welcomes you with spacious floor plan and sweeping ocean views. Marvel at the beautiful Maui sunsets from your...
Studio Condo with breathtaking ocean view
Located on the western coast of Maui, the condominium is in a town called Lahaina.Lahaina offers a world-class shopping complex with a vast range of shops and restaurants, as well as a renowned whaling museum, whale watching, scuba diving, surfing lessons to amazing...
Poipu Crater 24 - Stay in the Crater, A/C in the Bedrooms
POIPU CRATER 24 AT KOLOA KAI VACATION RENTALSYour Tropical Oasis in the Heart of PoipuImmerse yourself in the beauty of authentic island-style living at Poipu Crater 24, a tranquil retreat located in a unique enclave of 15 duplex bungalows nestled in the crater of an...
Gorgeous 2/2 Remodeled & upgrades galore!
Beautiful 2 bedroom 2 bath main floor condo boasts comfort and elegance with NEW floors, NEW blinds, NEW AC's! GORGEOUS! Located in highly sought after complex on the south shore of Maui. Fully loaded and wonderfully decorated. One bedroom is a suite with a king bed....
Kapalua Artistic Remodel - First Row 1BR/2BA
Relaxing pleasure in this spacious and unique cabana. Whale watcher's paradise with a backdrop of crashing waves serenade. Upon entry the panoramic view of the Pacific will have you reaching for a Mai Tai. Crashing waves below convince you you've found the right place....
Views, Views, Views Chef's Kitchen, Ample Supplies, Home Office, Weekly Discount
TESTIMONIALSWhat an incredible vacation spot! We love this place! The pictures on the website don't even capture how beautiful this place is This was probably the most well stocked and well equipped vacation rental we have ever stayed at - laundry detergent in the...
Corner Unit! Steps to the beach! Kihei Akahi with A/C
Escape to affordable luxury in the ideal setting! This charming corner unit features two bedrooms, two bathrooms, and delightful peek-a-boo ocean views. Each bedroom boasts a comfortable queen bed for your relaxation.Upon arrival at Kihei Akahi, you'll find everything...
🏖️Ocean & Golf Course Views | 2 Bdrm with Loft | AC | vrKCV
vrKCV - Country Club Villas 334, Professionally Managed by Kona Coast VacationsWelcome to Country Club Villas #334 – Oceanview Golf Course Condo with Spectacular Sunsets! Experience the magic of island living at Country Club Villas #334, a beautifully remodeled...
Hululani Luxury Estate, A/C, Pool and Spectacular Ocean Views
This serene estate is named Hululani, or "Heavenly," for its pristine beauty. This truly fabulous home has awesome, panoramic views of the mountains, Bali Hai and Hanalei Bay from virtually every room as well as from the private, saline swimming pool. Located on a quiet...
Beachfront Haena home with A/C - Near Tunnels Beach
This modern beachfront home was recently fully renovated. Hale Ekahi (One) is one of two properties on this beachfront lot. Ekahi offers modern beach furnishings to fill this luxurious beachfront home. The home has 3 bedrooms, 2.5 bathrooms, a fully equipped gourmet...
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...
🌺Last min Super Duper deal April 19- May 2 please inquire !
TVNCU number # 5150 Wailele Ikena (The Simpson House)... Hanalei Bay, Kauai, Hawaii. Hanalei has it all! Breathtaking views of dozens of cascading waterfalls, sheer cliff, ancient volcanic mountains covered with vegetation, and one of the most wonderful protected,...