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.
Na Hale 4 at Pauoa Beach - Private Oasis - Exclusive Access to Pauoa Beach Club and Amenities
Welcome to Na Hale 4 at Pauoa Beach Club, your luxurious retreat in the heart of Hawaii's premiere Mauna Lani Resort. Nestled within the prestigious gated community of Pauoa Beach Club, this stunning estate promises a perfect blend of tropical serenity and modern...
Executive Center Studio with Kitchenette, secure building pool, FREE PARKING
Updated downtown studio with (Free Parking a $50.00 Value per night can go in and out no charge/ dedicated parking stall few feet away from elevator ) located in the Aston Executive Centre. Enjoy hotel amenities including 24 hour security, pool, hot tub, on site laundry...
New Listing! Northshore Gem - 2 bd/2ba Plantations @ Princeville!
New! North Shore Gem: Organic Bedding, Luxe Island Amenities, AC, Pool, Hot Tub, Gym, Smart Home LUNALANIA unique boutique stay experience for those who tend to gravitate toward spaces that offer a bit more than the ordinary, this 2-bedroom, 2-bathroom Garden Island gem...
Hale Malu - a peaceful refuge above Hilo,
Welina mai to Hale Malu, a light-filled home of peaceful refuge, with three bedrooms and two baths, wood-burning fireplace (wood provided), spacious fully-stocked kitchen with modern amenities, free WiFi, and free off-street parking. Enjoy the views of Mauna Kea and the...
KAS 7307 Remodeled Condo Across Beach w Pool AC
Kamaole Sands 7307 Remodeled 1Bedroom Condo Across the Street from Kamaole III Beach Park at One of the Best Resorts in Maui with Pool, Hot Tubs, Tennis, and More FREE daily activities included with your stay value up to $554! Complimentary admission, every day of your...
Luxury 4BR Penthouse at the Villas at Poipu Kai
Welcome to The Villas at Poipu Kai, one of the nicest luxury condominium resorts on the South side of Kauai in Poipu. These spacious and upscale villas are part of the Poipu Kai Resort that offers access to additional recreational amenities to all in the Poipu Kai...
Kihei Surfside #304 - Spectacular Oceanfront, A/C, 2 Sofa Beds; 1/1.5 baths
Experience the perfect Maui escape at Kihei Surfside #304—an oceanfront retreat offering unforgettable views and coastal comfort. Just steps from Keawakapu Beach, this updated one-bedroom, one-and-a-half-bathroom condo captures the essence of island living with...
Wai'ula'ula Villa 415 Four Bedroom
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 refrigerator,...
!New Remodel Oceanview Waikiki AlaWai AlaMoana
New remodeled private, high rise studio in a secured apartment on Niu Street (Waikiki) with ocean view, Diamond head, city light, Ala Wai Canal view. Walking distance to Convention Center, Ala Moana, beaches, shops and eateries.Please inquire about other listings in...
Fully Remodeled Ocean Front Comfort HKOK316
Hawaii Tax ID: TA-101-435-1360-01TMK: 390080030055Oceanfront Bliss in North Kihei CondoWelcome to your private slice of paradise in North Kihei, where breathtaking ocean views await you from the moment you step into Unit 316. Experience the magic of Maui's coastline...
Papakea D206 - Ocean and pool views
Book with us and come to Maui to explore everything we have to offer!This well maintained 2nd floor private location has ocean, pool, and koi pond views from the lanai. Relax on the lanai listening to soothing Koi pond fountains while watching the whales breach in the...
Oceanfront Condo W Free Valet Parking & Balcony
This luxury apartment lies in the heart of Waikiki and is the perfect place to relax with friends and family. Sit on the balcony and sip a drink while watching the sun set over the horizon and the surfers ride the endless waves.The apartment comes with FREE valet...
A Modern Mix Waikiki Edition: 1 Br w/ Free Parking
***Amenities recreational deck renovations has begun. The renovation timeline is currently set from April 2025 - for the next 12-14 months (April - June 2026). Pool, hot tubs, grills, etc. will not be available during this time. Price has been adjusted due to...
Magic Skies Main Level Living
Enjoy the entire 2,300 sq ft level to yourselves, with panoramic views, wrap around lanai, full chefs kitchen, laundry, open concept living, dining, 3 bedrooms, 4 beds, 3 full bathrooms, with access to hot tub, game room. With specialty wood work throughout hand crafted...
Ground Level Condo Near the Pool!
Experience Princeville like a local in this 2-bedroom condo. Step into this fabulous property and be greeted by the amazing king beds in the bedrooms. The condo also offers enjoyable amenities such as a washing machine, AC, WiFi, a hair dryer, and an iron. With 2...
3 Beachfront Spas|90"THTR|Only home in Hawaii with Private Beach|Jurassic Park Filmsite|Beachfront Gym & Gazebo
You'll find a kayak, bicycles, and more on site at this family-friendly villa. Ahupua'a O Kahana State Park is an easy 13-minute walk away, so you can leave your car at the property, which offers onsite parking, or jump in your vehicle to make short work of the 2-minute...
LAST MINUTE SPECIAL1/15- 1/19 ~ FRESH Reno ~ QUALITY Villa (17T-3&4) ~ Easy Parking Level Access
Welcome to one of a few exclusive members of the Platinum Maui Vacations ohana, (familiy). We call this Kapalua Golf Villa, (unit 17 T-3&4), Hale O Ho'aloha. A Hawaiian phrase which roughly translates to English as 'Home of Friends'.We call this unit a 1.5 bedroom...
Mauka Sunrise, Walk to Hau‘ula Beach & Trails, A/C
Welcome to our tranquil three-bedroom vacation retreat nestled in the heart of nature's paradise. Each bedroom boasts a comfortable queen bed, ensuring a restful night's sleep for everyone. The master bedroom features a convenient in-suite full bathroom with a...
Ka'anapali Livin' the Dream Home - Private, luxury, resort-style property!
Come stay at our newly renovated, beautifully appointed, 3000+ sq ft., 3 bedroom, 2.5 bath beach home located on the Kaanapali Kai Golf Course. A short 3-minute drive or 10-minute walk to world famous Kaanapali beach, award-winning restaurants and Whaler's Village...
❤️PiH❤️ AQUA MARINE DREAM ★Big Golf Discounts★Free 2026 Hilton Passes★Tennis/Pickleball
Brought to you by Paradise in Hawaii Luxury Homes.Welcome to Aqua Marine Dream, a part of our Hawaiian Luxury Collection. It's is a wonderful 4 bedroom home and 4.5 Bath (Mahina Model) equipped for up to 10 people.The home has had recently been updated with lovely new...
Dreamy Puako Beach House on White Sand Beach with AC!
Absolutely stunning 3 bedroom/2 bath beach house. Hale Laʻi Laʻi ~ Home of tranquility and contentment. Recently remodeled to create a feeling of contemporary elegance and relaxation with total beach vibes. Everything has been upgraded with soft modern finishes...
❤️Best Views on Maui! Perfect for Honeymooners!!❤️
** NO RESORT OR PARKING FEES! **Welcome to your 10th-floor oceanfront escape at The Mahana! This freshly renovated studio offers floor-to-ceiling views of the Pacific, where you can spot whales, turtles, and snorkelers right from your private balcony.Inside, enjoy a...
Holiday Special! Whale Watching, Ocean Views & Chic Kapalua Condo—No Resort Fees
Newly remodeled, fully air-conditioned, ocean view condo. Ocean, Island, Sunset, and Whale Watching Views! Our unit is on the third floor of Building G at Papakea Resort with pool view and unobstructed ocean view with year-round sunsets.We want to provide our guests...
Maui Resort Rentals: Hilton Maui Bay Villas - Brand New 2BR Penthouse Oceanview Suite!
Nestled among 27 acres of lush tropical gardens, the Hilton Maui Bay Villas is a luxurious, secluded resort located on South Maui's sun-drenched coast. Situated minutes from several upscale resorts, pristine beaches, and championship golf courses, guests will enjoy...
Maui Eldorado L202 Updated Condo with Beachfront Cabana
Eldorado L202 Charming Maui Getaway at Updated 1Bedroom Condo at Maui Eldorado Resort in Kaanapali! Facilities include Pool, Hot Tub, Fitness Room and Beachfront Cabana Indulge in the ultimate Hawaiian escape at this updated 1-bedroom, 2-bathroom condo nestled within...
PACSA304 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),...
Sunny Poipu Condo w/ A/C close to Beach. Moir Garden and Partial Ocean View #301
Quiet & Relaxing garden view Condo with A/C at Kiahuna Plantation Resort. Inside the condo is newly renovated with island modern furniture, decor and photography by local artist, Steve Munich so you can enjoy the sights of Kauai indoors. There is a private, one bedroom...
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...
3 Bed Villa Views, Beach, Hot Tub, Pools, Golf
Summary:Corner unit with sweeping golf views, just steps away from the beach. Fully stocked with everything you might desire, steps restaurants or grocery stores. End unit feels like a house, provides privacy from neighbors, while being only steps away from the gorgeous...
Papakea H201 - Vacation West Maui
Escape to Paradise in Maui's Premiere Oceanfront ResortNestled in the heart of Papakea Resort, unit H201 beckons you with breathtaking ocean and garden vistas. This corner unit on the second floor offers more than just a place to stay – it's your portal to the magic of...
2Bd/2Ba Condo at Lagoon Tower Hilton Hawaiian Village Sleeps 6
Nestled within the renowned Hilton Hawaiian Village, this spacious 1,025 square foot, two-bedroom, two bath condo offers the ideal retreat for families seeking relaxation and adventure.Step into the expansive living room, where ample seating invites you to unwind after...
Maui Resort Rentals: Kaanapali Alii 3114 – Luxuriously Upgraded 3BR Oceanview Penthouse!
This upgraded residence boasts gorgeous Pacific Ocean and lush West Maui Mountain views from its prime top-floor vantage point right at Kaanapali Point. Guests will enjoy views of the gorgeous turquoise-hued ocean from nearly every area of the home, including right from...
Maui Resort Rentals: Honua Kai – Incredible 5 Bedroom Oceanfront Offering, Over 3300 combined Sq. Ft. w/ Built-in Viking BBQ!
This phenomenal five-bedroom oceanfront offering at the popular Honua Kai Resort on Kaanapali North Beach combines a stunning 3BR oceanfront residence with a neighboring 2BR partial oceanview suite to create the perfect gathering space for large groups and families to...
Coconut Villa Entire home in KoolinanWalking distance to the shops and beaches
Enjoy your morning coffee or evening cocktails out on our lush tropical lanai with the tranquil backdrop of the Ko Olina golf course. Take in the stunning sunsets from this perfect vantage point.Our villa is located in an ideal location; everything is within walking...
1 Acre PRIVATE RESORT,4 bed, 3 bath, cinema, spa
Summary:Rated in top 10 Airbnb's on the coast. Treat yourself to a vacation surrounded by unmatched landscaping, ocean view, 2000 sq/ft single level, fully stocked home with 4 bedroom, 3 bathrooms, Movie Theater; a/c in each room, waterfall, grotto, tiki torches, fruit...
Upgraded 3 bed w Ocean View, Pool, Hot tub, 2 King
Summary:Enjoy daily sunsets over the ocean right from living room. This Corner unit is a privately owned part of Wyndham hotel, provides you best of both worlds - pool, tennis, spa, gym, billiards, ping pong etc. while being completely remodeled with brand new...
bright 3 bed,3 bath, pool, hot tub, tennis, breeze
Summary:Relax with the whole family in this lovely 3 bedroom 3 bathroom condo that overlooks the Waikoloa Village Golf Course and Kohala Mtn. Complex has a large swimming pool, hot tub, exercise room. tennis court and pickleball court. Barbecues within steps of the...
The ‘IMI OLA at Kiahuna Beach - Great Location on Kauai's South Shore -A/C
Aloha! E komo mai to our little slice of paradise. Located in the community of Kiahuna Plantation Resort in Poipu, Kauai in Unit 127. Our first-story walk out unit sits on a 35-acre beachfront resort with large rolling lawns, well maintained gardens, and a path that...
Spectacular View Home for 20! Ocean, Mountain, golf views! 5min from Poipu beach
Brand new listing on VRBO; I'm a Super host for the past 3 years on Air B&BThis newly constructed luxury home sleeps 20+; it's perfection for multigenerational gatherings, vacationing with a few families or large groups. Partial ocean views sits backing the Kukui’ula...
North Shore Beachfront Bliss! Perfect family-sized home on a sandy beach
Come and enjoy the best the North Shore has to offer in this right-sized sandy beachfront home, perfect for families and small groups. This property is located on a gorgeous bay in Haleiwa so you not only have a beautiful long sandy beach to enjoy, but you are a stones...
Hale Keani O-1203 stunning Views to relax
Welcome to Penthouse Hale Keani O-1203 at the Beach Villas at Ko Olina – Your Luxury Hawaiian EscapeIndulge in the splendor of our breathtaking two-bedroom, two-bath penthouse, located on the twelfth floor of the Ocean Tower at the prestigious Beach Villas at Ko Olina....
Maui Resort Rentals: Honua Kai Konea 243 - Large 2BR w/ Great Interior Courtyard Location
Konea 243 is a luxurious two-bedroom suite offering lush interior courtyard views as well as partial views of the ocean through the palm canopy. Its excellent interior Konea Tower location is one of the most sought after areas of the entire Honua Kai property.Gather,...
Tropical Harmony Oasis with Breathtaking Ocean Views in Hawaii
Summary:Our Harmony House is a one-of-a-kind retreat that offers guests a peaceful and rejuvenating experience. It's perfect for families or couples traveling together, with two bedrooms and two bathrooms. As you enter the space, you'll be struck by the unique decor,...
Private1BR @Waikiki Max 6! near Ala Moana Center!
【Basic Info】This is a 1BR room in Waikiki!!You can stay with you friends, partner, family. You can spend your time with a reasonable price.This condominium is located west area in Waikiki.You can walk to Hilton village lagoon and beach and Kahanamoku beach in 5-10min...
Poolside Waikiki Retreat w/ AC, surfboard storage, walking distance to beach!
Located in the center of Waikiki with amenities like A/C, on premises laundry, and bike & surfboard storage, this spot is a no brainer. Directly across from the *eight foot deep* outdoor pool and patio, and just blocks from the beach, this apartment is truly a piece of...
WALK to the Kapalua Beach, New Bespoke Luxury Golf Villa, Ocean & Golf Views
Welcome to White Lotus at Kapalua Golf Villa 18T5, 2-story 3 bedroom & 3 bathroom plus a powder room luxury retreat offering over 2,000 sq. ft. of interior living space plus 500 sq. ft. of covered lanais. Situated directly on the 4th tee of the Kapalua Bay Golf Course,...
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,...
Luxury 4-Bedroom Condo with Panoramic Ocean Views!
Welcome to our Kona Beach Home at Hale Kai O’Kona! A Spectacular Ocean front Condo located on the incredible Western Shores of the beautiful Big Island. Our Vacation home has been completely remodeled from top to bottom. It is close to everything (Town, shops, beach,...
Kumulani A2 Two Bedroom with Den
This ground-level, oceanview residence, finished in classic Hawaiian decor, offers a great room with sliding glass doors for indoor/outdoor island living, a full kitchen with premium stainless steel appliances (including a wine refrigerator) and granite countertops,...