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.
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 Welcome to our beautiful 2-bedroom, 2-bathroom condo at Pacific Shores in Kihei, Maui. Pacific Shores A304 has been thoughtfully updated in...
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...
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 Koolina Walking 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,...
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...
WHITE LOTUS🏝️ Brand New Bespoke Euro Luxury 3BR 3BTH Golf Villa, Steps to Beach
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,...
Four Bedroom Oceanfront Condo with Amazing Sunsets!
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 Residence A2
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,...
Ocean View. Hilton Waikoloa Pass for 2025. B305 Vista Waikoloa
Vista Waikoloa B305. Ocean Views!This vacation rental is professionally managed by ResorticaHawaiiPlease scroll down for detailed informationHilton Pool Pass: Valid for stays now through December 31, 2026. Maximum 6 persons per pass (children under the age of 5 are not...
Exceptionally Pristine Haleiwa North Shore Beachside Retreat
FIND PEACE & ESCAPE FROM STRESS HERE. -This is considered one of the best North Shore neighborhoods for location, privacy & safety. The large North Shore Winter surf is here! Check it out just minutes away down a private beach access. Shell collecting, monk seal & green...
Luana Garden Villa 6D @ Honua Kai Resort Kaanapali
Luana Garden Villa 6D is a unique family friendly, ocean front luxury villa on Maui. Special Spring Break Rates are being offered on this Villa that is located in the center of the Honua Kai Resort & Spa between the two resort towers. It is just 330 steps from...
Coconut Plantation 1086-4: Elegant 3BR Ko Olina Townhouse w/ Fairway Views
Set along the 11th fairway in Ko Olina Resort, Coconut Plantation 1086-4 by Gather is an upstairs townhouse villa where island ease meets resort convenience. Contemporary Asian-inspired decor, a breezy covered lanai, and views of swaying palms create a tranquil home...
Ocean-Waikiki Skyline Panoramic PH in Luxury Condo w/Parking & Near the Beach
This property requires a minimum 30-day rental. Book with confidence—professionally managed by Ali'i Beach Rentals, an award-winning property management company.*This penthouse is new to our inventory. Reviews are coming soon. Please rest assured this house is...
Makaha-465 Farrington: Spacious 4BR Oceanfront Haven with Modern Amenities
Set your sights on paradise at Makaha – 465 Farrington Hwy by Gather, a timeless beachfront retreat on Oahu’s serene west shore. Once a cherished family getaway and now lovingly reimagined for modern comfort, this four-bedroom, three-and-a-half-bath home offers a...
Ko Olina Kai 1105F: Family-Friendly w/ Pool, Spa, Near Disney Resort
Ko Olina Kai 1105F offers a serene island escape in Kapolei, HI, where tropical greenery frames each morning and soft trade winds breeze through the airy lanai. Spanning 1,144 square feet, this thoughtfully designed condo blends comfort and elegance—an ideal retreat for...
Ko Olina Kai Estate #20: Elegant Fairway Retreat with Luxe Amenities
Bordering the signature 18th fairway of the Ko Olina Golf Course, Ko Olina Kai Estate #20 by Gather offers peaceful resort living framed by sweeping green views, gentle trade winds, and warm island light. This spacious two-story home features over 2,200 square feet of...
Ko Olina Kai #17: Spacious, Stylish Retreat with Golf Course Views
Tucked along the prestigious 18th Fairway of the Ko Olina Golf Course, Ko Olina Kai Estate #17 is a private retreat where resort living meets the comforts of home. This executive four-bedroom estate within the gated Ko Olina Kai Resort Community offers expansive fairway...
Ko Olina Kai 1097C: 3BR Hawaii Haven with Golf, Lagoons, and Spa Access
Welcome to Ko Olina Kai 1097C by Gather, a beautifully furnished three-bedroom, three-bathroom Golf Estate located in the prestigious Ko Olina Resort. This two-story villa combines upscale comfort with the laid-back luxury of Hawaii living, making it the perfect retreat...
Ko Olina Kai 1083C: Contemporary 3BR, Private Lanai, Walk to Beach & Dining
Welcome to Ko Olina Kai 1083C by Gather, a beautifully furnished two story townhome in the gated community of Ko Olina Kai Golf Estates. This island contemporary retreat blends modern comfort with effortless indoor outdoor living, creating the perfect environment for an...
Fairways at Ko Olina 4A: Luxury Condo w/ Balcony Views & Resort Amenities
Fairways at Ko Olina 4A is your serene island retreat, nestled in a quiet corner of the Resort at Ko Olina. This upgraded two-bedroom, two-bath condo offers garden views, modern comforts, and resort-style amenities, all just steps from sandy lagoons and world-class...
Fairways Ko Olina 27H: Your Ultimate 3BR Retreat in Hawaii with Resort Access
Welcome to Fairways at Ko Olina 27H, a spacious three-bedroom, two-and-a-half-bath townhouse offered exclusively as a monthly vacation rental within the gated Fairways community on Oahu’s sunny west coast. This comfortable home blends open living spaces with serene...
Luxurious 3BR Fairways at Ko Olina 20G with Golf Views
Fairways at Ko Olina 20G offers a luxurious retreat in Kapolei, HI, where vibrant island life meets modern comfort. This beautifully maintained three-bedroom, two-bath townhome spans 1,289 square feet and provides an inviting haven for families or groups seeking a...
Special! Coconut Plantation 1214-2 Ko Olina Beachfront Escape Resort Amenities
This property is offered as a monthly rental. Although full-month occupancy is not required, the monthly rate remains fixed and applies in full, regardless of the number of nights stayed, as prorated rates are not available.Welcome to Coconut Plantation 1214-2 Aloha...
Coconut Plantation 1158-1: Spacious 3BR with Modern Kitchen & Private Lanais
Welcome to Coconut Plantation 1158-1 by Gather, a beautifully updated two-story retreat in the heart of Ko Olina Resort. Blending island charm with contemporary upgrades, this 3-bedroom, 2.5-bath home offers 1,784 square feet of stylish living space and private lanais...
Coconut Plantation 1190-1: Spacious 3BD Resort Villa w/ 3 Lanais—Walk to Lagoon
Welcome to Coconut Plantation 1190-1 by Gather, a luxurious and newly refreshed three-bedroom, three-bath townhome located within the prestigious Ko Olina Resort on Oahu’s sun-drenched west side. As the largest model in Coconut Plantation, this elegant 2,146-square-foot...
Coconut Plantation 1086-1: Upscale 3BR Condo in the Serene Ko Olina Resort
Coconut Plantation 1086-1 by Gather offers a relaxing and beautifully updated retreat within the gated Coconut Plantation neighborhood of Ko Olina Resort. This spacious two-story home features 1,715 square feet of island-inspired living, three comfortable bedrooms, two...
Coconut Plantation 1078-1: Bright 3BR Beach Home Steps from Ko Olina Attractions
Welcome to Coconut Plantation 1078-1, a spacious 3-bedroom, 3-bath townhome in the heart of Ko Olina Resort on Oahu’s sunny leeward coast. Offered exclusively as a monthly rental, this 1,548-square-foot retreat combines comfort, convenience, and the laid-back elegance...
Ko Olina Beach Villas O905: 3BD Luxe Villa w/ Stunning Sunset Views
Welcome to Ko Olina Beach Villas O905, a refined 3-bedroom, 2.5-bath ocean-view retreat set high on the 9th floor of the Ocean Tower in Ko Olina Resort. Spanning 1,507 sq ft of open, airy living space with room for up to 8 guests, this villa blends luxury comfort with...
Ko Olina Beach Villas O805: Chef's Kitchen & Stunning Views
Welcome to Ko Olina Beach Villas O805 by Gather, where panoramic ocean views, luxurious interiors, and a prime location within the exclusive Ko Olina Resort create the ultimate Hawaiian escape. This beautifully appointed 3-bedroom, 2.5-bath villa offers sophisticated...
Ko Olina Beach Villas O425: Oceanfront Getaway
Ko Olina Beach Villas O425 welcomes you to upscale island living on Oahu’s sunny west coast. Perched on the fourth floor of the Ocean Tower in Ko Olina Resort, this two-bedroom retreat blends sweeping Pacific views with breezy, open interiors and resort-style...
Ko Olina Beach Villas 0401: 3BD Corner Luxe Villa w/ Pool & Garden Views
Welcome to Ko Olina Beach Villas O401, a corner retreat on the upper floor of the Ocean Tower at Ko Olina Resort. This elegant three-bedroom, two-and-a-half-bath villa offers a seamless blend of sophistication and island ease, surrounded by panoramic views of the...
Ko Olina Beach Villas O1402: Spectacular 14th Floor Penthouse w/Ocean Views
Welcome to Ko Olina Beach Villas O1402 by Gather, a 14th-floor penthouse where sophistication and comfort meet Hawaii’s natural beauty. Overlooking the Pacific Ocean and Ko Olina’s tranquil lagoons, this luxurious three-bedroom, two-and-a-half-bath villa accommodates up...
Ko Olina Beach Villas O1011 by Gather: Lux Penthouse w/ 2 Lanais & Stunning View
Welcome to Ko Olina Beach Villas O1011, a three-bedroom, three-bathroom penthouse on the 10th floor of Oahu’s renowned Ko Olina Resort. With 1,532 square feet of beautifully appointed living space and two expansive lanais, this villa blends modern luxury with island...
Ko Olina Beach Villas O1006: Luxe Penthouse w/Pool, Golf, & Ocean Views
Welcome to Ko Olina Beach Villas O1006 by Gather, a luxurious two-bedroom, two-bathroom penthouse on the tenth floor of the exclusive Ocean Tower. Designed for up to six guests, this elegant villa offers panoramic ocean views, serene vistas of the resort pools and koi...
Ko Olina Beach Villas B901: Luxe 3BR Penthouse w/ Beachfront Views
Ko Olina Beach Villas B901 by Gather is a luxurious ninth-floor penthouse overlooking the calm blue waters of Ko Olina Lagoon. With 1,491 square feet of indoor living space and a generous lanai framing panoramic ocean and pool views, this three-bedroom, three-bathroom...
Ko Olina Beach Villas 608: Spacious 2BR Luxe Home w/ Ocean Views
Ko Olina Beach Villas B608 by Gather offers an elevated island getaway from the sixth floor of the coveted Beach Tower—Ko Olina’s building closest to the ocean. This beautifully appointed two-bedroom, two-bath villa accommodates up to four guests and showcases stunning...