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.
Bright and airy garden condo in spectacular Princeville with air conditioning
New in 2025: We installed high-speed fiberoptic wifi (the fastest internet option on the island)High ceilings, wide green belts, and privacy in a quiet complex. Located in spectacular Princeville and just a short walk to lovely Anini Beach and the Westin Princeville....
Modern & Polished Oceanfront Vistas
Summary:Bright, modern, and spacious. Complete remodel in December 2021! 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...
Polo Beach Club #602: 2 BR Condo with Stunning Views
Polo Beach #602Welcome to Polo Beach #602, a beautifully remodeled oceanfront condo located at the prestigious Polo Beach Club in Wailea. Perched on the sixth floor, this spacious two-bedroom, two-bathroom retreat offers stunning panoramic views of the Pacific Ocean and...
Hawaiian Chic Crater Retreat- a tropical jungle escape in a secluded crater
***FYI- swimming pool will be closed April 15th-May 15, 2024 for repairs***Being on the ocean is amazing, but is it as amazing as having a one of a kind condo in a secluded crater? It has many of the same amenities as a $1000/night nearby resort does, for a much better...
Chic & Elegant Oceanfront Vistas
Summary:Welcome to Paradise! Our completely remodeled studio condo at Kauhale Makai Village by the Sea awaits. Completely renovated and outfitted in December 2021. Experience our waterfront condo with fabulous ocean views located in sunny Kihei. Beach chairs, umbrellas,...
Hilton Pool Pass thru June 2025 and Golf Discounts. Waikoloa Colony Villas 1002
This vacation rental is professionally managed by ResorticaHawaiiWaikoloa Colony Villas 1002Please scroll down for detailed information.Bedding Configuration:Master Bedroom: King BedGuest Bedroom: King BedGuest Bedroom:Queen BedAdditional Bedding: Sleeper Sofa in Living...
Maui Resort Rentals: Honua Kai – 6 Total Bedrooms, Ocean Views, 3300 Combined Sq Ft, Sleeps up to 18!
This one-of-a-kind 6 bedroom offering combines one 2br ocean view suite with two 2br partial ocean view suites located directly across the hall to create a tandem package with 3300 sq ft of interior living space and the capacity to accommodate up to 18 guests. Enjoy the...
Maui Banyan king, 2 bathroom, steps to Kamaole beach, sleeps 4 - No parking fee
In Maui its all about LOCATION and this unit is in the perfect spot. Maui Banyan is located in prime South Kihei where the weather is sunny and beautiful year round. It’s across the street from Kamaole Beach II which is one of the few beaches in Maui with a lifeguard...
Molokai Oceanfront large beautiful home - Gorgeous secluded beaches out front!
This chic two story 3bdrm/2bth townhouse is located on the west side of Molokai in a quiet residential complex, located right on the beach! Your Molokai island getaway starts here! Offering one of the best locations on Molokai since it's located along one of Molokai's...
Maui Resort Rentals: Honua Kai – Incredible 5 Bedroom Oceanview Gem, Interior Courtyard, Sleep up to 16!
This 5 bedroom gem combines one of our very finest 3 bedroom ocean view residences with a partial ocean view 2 bedroom suite located directly next door. It is perfectly suited to larger groups or families of up to 16 guests.The generous combined 3000+ sq ft square foot...
OCEAN FRONT 2bd/rm Townhome New Remodel Ocean and Sunset Views AC Pickleball!
Aloha, we would love to have you as our guests! It is a pleasure to know you are interested in our Ocean front 2 bedroom/ 2 bath townhouse. We have had a tremendous amount of positive reviews, but decided to update the property to provide an even better guest...
Kilohana At Poipu By Parrish Kauai - Private Pool with AC - Great for the Family
Kilohana at Poipu is a private tranquil vacation home nestled in the center of Kiahuna Golf Village and the Robert Trent Jones, Jr. golf course. This single-level home has a spacious indoor/outdoor living layout centered around a heated swimming pool and courtyard,...
Kaanapali Royal B-102 - Remodeled - Golf Course Living - Free Fun
Completely remodeled December 2021 - With more than 1,500 sq ft of air-conditioned living space, this gorgeous condominium is ideally located directly on the Kaanapali Golf Course. "Sale" into Whale Season: PROMO CODE: SALE26. (Can not be used in combination with any...
Wai'nani Waterfall House HEATED Salt Water Pool /Hot Tub BEACH GEAR Games VIEWS!
Welcome to the Wai'nani Waterfall house located in sunny Poipu on the south shore of Kauai. This home has all you and your Ohana are needing for the perfect island getaway. Set in the heart of Kiahuna Plantation Golf course, this new home was designed with families in...
Beachfront Spectacular Ocean views, steps to white sand Beach & walk bike Path
Listen to the sound of the waves from this beautifully furnished corner unit and admire the views up and down the coast from the spacious lanai. Upgraded with granite countertops and travertine floors in kitchen and bathrooms. Unit 219 is very private with unobstructed...
Stunning Oceanview 1 level 2B w Split AC at Kamaole Sands!
Welcome to our newly renovated beautiful seaside single-story 2 bd 2 ba condo at the highly rated Kamaole Sands, located yards away from the stunning Kamaole III beach, Maui's famed "postcard beach" that is fantastic for snorkeling, swimming and boogie boarding and more...
Ocean View - 2 Bedroom - Marriott's Waiohai Beach Club - Full Resort Access
Enjoy a luxurious stay for a fraction of the cost. Typical savings range from 30-70% when comparing our rates to direct resort bookings. All of our units are managed and maintained by the resort. Upon arrival, guests will check-in at the resort’s front desk using their...
Ocean View - 1 Bedroom - Hyatt Ka'anapali Beach - Full Resort Access
Enjoy a luxurious stay for a fraction of the cost. Typical savings range from 30-70% when comparing our rates to direct resort bookings. All of our units are managed and maintained by the resort. Upon arrival, guests will check-in at the resort’s front desk using their...
30-Day Stay at Kailua-Kona House w/ Hot Tub!
Breathtaking views, vibrant marine life, and screensaver-worthy beaches await when you visit this 2-bedroom, 2-bath home in Kailua-Kona. Once you've settled in, choose to relieve your post-travel stresses with a soak in the private hot tub or cocktails on the spacious...
2 Bed 2 BA with Full Direct Views of Bali Hai and Hanalei Bay! This is Paradise!
Hanalei Bay Resort 4221/4222 – Bali Hai & Hanalei Bay at Your DoorstepWelcome to Hanalei Bay Resort 4221/4222 – a truly one-of-a-kind getaway offering iconic panoramic views of Bali Hai and Hanalei Bay. From the moment you walk in, you’ll know you’ve arrived in...
Waipouli Beach Resort Exquisite Beautifully Decorated Extra Large Luxury
Newest Listing! Waipouli Beach Resort Exquisite Beautifully Decorated Extra Large Unit D310! Best of the Best! Ocean & Pool View! Central AC! Beach Chairs (up to 4) and Cooler!**Exquisite Luxury Condo of Distinction located at the World Renown Waipouli Beach Resort on...
Hilton Waikoloa Pool Pass Included 2025 and Waikoloa Kings Club Golf Discounts.
This vacation rental is professionally managed by ResorticaHawaiiWaikoloa Fairway Villas H4PLEASE NOTE: Waikoloa Fairway Villas H4 is listed for sale. Guests may be asked to accommodate showings/inspections with 48 hours notice. Please reach out with any questions....
Stunning 2-bedroom Wailea Elua, walk to beach, ocean view!
Welcome to Wailea Elua #101!A spacious 2-bedroom, 2-bath condo in the heart of Wailea’s resort area. Just a 5-minute walk to Ulua Beach, one of Maui’s best for snorkeling and swimming, this home offers a relaxing tropical retreat with ocean and garden views. Walk to all...
Breathtaking Ocean Front Views. Incredible Reviews.
Unit 516 is a stunning fifth-floor penthouse with unobstructed ocean views of Molokini, KahoÊ»olawe, LÄnaÊ»i, and the West Maui Mountains. Perched above the palms with a spacious ocean-facing lanai, this is your ideal base for sunsets, turtle-watching, whale season, or...
Maluhia Makai - Luxe Kukui'ula island retreat in Poʻipu; AC, private heated pool
This luxury home is 2200 ft.² of air-conditioned space that opens up to 1000 ft.² of an outdoor living lanai. The design of this home seamlessly marries the indoors & outdoors together to make a grand tropical outdoor experience. Pass through its custom entry wood gate,...
Charming Modern Home Stunning Scenery and Nature BBPH2021/0002 SUP2 2020/0008
Located in the heart of the north shore of Maui, this charming 3-bedroom residence is a refuge for those who want to experience the beauty of Maui in comfort and tranquility. The house is 2254 square feet and has a beautiful view of a Hawaiian native forest. It has...
Primo View Beach Condo w/Washer/Dryer, Free WiFi, Kitchen – Waikīkī Shore #716
This deluxe one-bedroom one-bathroom suite offers wonderful views of Waikiki beach and Pacific Ocean from the furnished lanai. This unit has a full-size kitchen with all the appliances to make wonderful meals in your home away from home. The suite is also furnished with...
Kihei, Maui - Fully Renovated, A/C, Pool, Tennis, Beach
This condo has been completely remodeled floor to ceiling! - New tile, bathroom, kitchen, appliances, and new furniture & bedding throughout.Condo Includes:- Stackable washer and dryer with complimentary start-up detergent supply- A/C in the living room and bedroom-...
Walk to Hanalei Bay&Town. Views of Waterfalls&Mountains. A/C. FREE Surf,Sup,Bike
Aloha, You will love our 3 bedroom, 3 bath HANALEI GETAWAY Vacation Rental home that is perfectly situated in the heart of Hanalei Bay, Kaua'i. At your vacation home you will experience the views of numerous breathtaking waterfalls and the majestic Hanalei mountain...
Makana Nui - Beachfront Home on Hanalei Bay
Welcome to the Makana Nui, located on the famous Weke Road in Hanalei. This home sits directly on the beach and is just a short walk through your private lawn to the sand. The picturesque Hanalei coastline remains relatively undeveloped and provides breathtaking views...
New Listing, Wailea Ekahi 4A, Close to Best Beaches, Shops of Wailea & World Class Golf
Summary:Lovely, Spacious Maui Townhouse: Steps from Keawakapu Beach!The Space:Escape to paradise at Wailea Ekahi Village 4A, Maui's dream vacation rental. This spacious 2-bedroom, 2.5-bathroom townhouse offers the perfect blend of indoor comfort and outdoor...
Papakea L301 - Direct Oceanfront Luxurious Corner 1B/1B, Newly Renovated, AC!
Oceanfront corner condo with panoramic views from Lanai to Molokai - unobstructed sunset views any time of the year. At dusk, tiki torches light the path to the water where the sun sets between the neighbor isles of Lanai and Molokai. Located on the third floor, this...
KBM Resorts| MON-1205 At Montage Kapalua Bay
** Limited Time Special Offer: Reserve any KBM Resorts property in Hawaii with an arrival date between now and December 31, 2026 for 6 nights or more and receive a FREE 4-door rental car from top providers--Hertz, Alamo, Avis, or Budget. Convenient airport pick-up and...
Hualalai Waiulu Villa 133B ~ Updated, Spacious with Great Views!
This spacious 2 bedroom, 2 bath single-level villa is centrally located on the Resort’s popular Waiulu Street overlooking beautiful Punawai Pond, the 5th Hole of the Member’s Ke`olu Golf Course and the ocean beyond. With 1854 square feet of living space, additional...
Waiohai Beach Club - Island View
Experience the unparalleled magic of Hawaii at Marriott's Waiohai Beach Club, a premium vacation ownership resort on Kauai. Located by the ocean on Poipu Beach, we offer spacious villa rentals and an array of resort amenities for your visit to the Garden Isle. Find your...
Direct Oceanfront Maui Studio,Romantic,Breathtaking View from Huge Private Lanai
Welcome to my Oceanfront studio, which is literally 50 ft to the water. Wake up to a breathtaking oceanview, take it all in from the spacious lanai, fall asleep to the sound of the ocean every nightRecently upgrade the TV to a 55inch Smart TV, which works w/ Apple...
Spacious 1 Bedroom Ground Floor Condominium in Kailua-Kona
#135 Casa De Emdeko is amazing. The condo is 920 square feet, on the ground floor 30 feet from the sand and less than 30 yards from the ocean. .
Golf Course Views | AC & Shared Pool |vrKCV
vrKCV - Holua Kai 6, Professionally Managed by Kona Coast VacationsHolua Kai 6: Luxury Home with Stunning Golf Course Views and Modern Comforts in a Gated CommunityWelcome to Holua Kai 6, your home away from home! Nestled within the private, gated community of Holua Kai...
Hale ONA LOA: Direct Oceanfront, Gated, 4 Bedroom, 3 Bathroom Home!
Hale Ona Loa – Iconic Oceanfront Luxury on Alii DriveNEWLY REMODELED | OCEANFRONT | PRIVATE POOL | DESIGNER FINISHESStep into coastal elegance at Hale Ona Loa, one of the most spectacularly reimagined oceanfront vacation homes along famed Alii Drive. This fully...
Maui Townhome across the Street from Pohaku Beach w/ Incredible Ocean Views
We are conveniently located between Kaanapali and Kapalua on Maui’s world famous west coast. Kahana Villa is across the street from Pohaku Beach (S-Turns Park) with white sand and where turtles frequent. You can watch whales from the lanai and master bedroom! All rooms...
Kaneohe Bay View 2br/1.5ba
***HAWAII STATE LAWS governing short-term rental properties: In order to comply with the Honolulu vacation rental rules (Honolulu and County Ordinance 25-2, Bill 62), our property is available for month to month occupancy with a minimum 90 day stay. This means that our...
Deluxe 2 Bedroom 2BA on Ocean Front Property with Private Beach Unit B131
This recently renovated and conveniently located, 1288 sq. ft ground-level unit is steps away from the pool, the private sand beach, and an ocean-front salt-water pool. It boasts a spacious living room and dining area with high speed internet. The fully equipped kitchen...
Professionally designed and remodeled in 2021! 2 master bedrooms, spacious plan
2025: New appliances (French door refrigerator with filtered cold water and ice dispensers, ultra quiet dishwasher) and outdoor sofas.2024: (2) New sofabeds!2021: Professionally designed and newly remodeled! No expense has been spared to make this a comfort. All brand...
Hale Hui Kai 211 Large Lanai overlooking the beach
South Maui oceanviews from both bedrooms and the living room/kitchen. This private oceanfront condo is on the second floor of the south side of the building ...about 30 steps along the pathway leads to the gem of south Maui, Keawakapu Beach!Keawakapu Beach, located on...
Stunning Views! Luxury Penthouse Kahana Villa E705
Summary:Enjoy your stay in Maui worry-free! Our short-term rental property is unaffected by any proposed legislation that may impact other accommodations. Book with confidence and experience the beauty of our island without any risk of cancellation.Stunning views that...
Luxury North Shore Beachfront - contact for details HI requires 1 renter/30 days
Nalu Hale is a luxurious 5 bedroom+, 6 bathroom, 5 star quality home located on the famous North Shore, Oahu. See IG name below, so you can see our profile. PLEASE CONTACT FOR CLARITY ON HAWAII REQUIREMENTS FOR ONLY 1 RENTER PER 30-DAY PERIOD TO ENSURE CLARITY ON WHAT...
🏖️Corner Unit | AC & WIFI | Concierge Included | vrKCV
vrKCV - Vista Waikoloa D201, Professionally Managed by Kona Coast VacationsWelcome to Vista Waikoloa D201Relax and unwind in this beautifully appointed two-bedroom, two-bath unit that offers the perfect retreat for couples or small families. With a spacious lanai, this...
Spacious Waterfront with Gorgeous View & Pool
Waterfront home with a million dollar view of Kaneohe Bay! Enjoy fresh tradewinds on your covered decks, and the comfort of a/c inside. This custom home has spacious living areas on two levels with fast WIFI indoors AND out! 5 bedrooms, 2 living rooms, flat screen in...
New Waikiki Boutique Condo 1.5 blocks to the sands of Waikiki Beach!
This boutique condo is just 1½ blocks to the pristine sands of Waikiki Beach! Newly renovated studio with a fully equipped kitchenette, and beautiful mountain/city views from the private lanai. The ideal location and beach themed decor make this vacation retreat one you...
SPECIAL DEALS! One of a Kind! THE Best Ocean Views with Bali Hai & Hanalei Bay
Welcome to Hanalei Bay Resort 4222 – a truly one-of-a-kind getaway with iconic panoramic views of Bali Hai and Hanalei Bay. From the moment you step inside, you’ll know you’ve arrived in paradise.This spacious one-bedroom retreat features a remodeled kitchen with exotic...