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.
Westin Kaʻanapali North 1BR Premium – Island Retreat
Discover your perfect Maui escape in this 1-Bedroom Premium Island View Villa at The Westin KÄÊ»anapali Ocean Resort Villas North. Offering approximately 750–900 square feet of space, this villa is ideal for couples or small families, with thoughtful details that make...
Island View - Marriott's Waiohai Beach Club: 2 Bedroom - Gorgeous Beach access!
The Waiohai Beach Club is beautifully landscaped with waterfalls and lagoons, lush tropical plants, and the sandy shores of Poipu Beach steps away. Spend a lazy day in the sun snorkeling or swimming in the ocean or the two outdoor pools. While the beach is perfect for...
Marriott Waiohai Beach Club: 2 bedroom Villa oceanfront resort on Poipu Beach
Marriott's Waiohai Beach Club - 2 Bedroom, 2 Bath, Full Kitchen, sleeps 8. Full Resort Access.Units assigned upon check-in. Full access to the resort’s services and amenities are included with every reservation. Located on the beautiful Poipu beach on the island of...
Newly Renovated Studio w/ Rooftop Pool & Near Waikiki Beach!
Aloha from Midway Vacations! Our team of local hospitality experts is dedicated to turning your Hawaiian getaway into a reality. When you stay at one of our properties, you can count on a professionally cleaned and meticulously maintained experience. We're even...
Kaanapali Alii | 475
Kaanapali Alii 4752 Bedrooms | 2 Bathrooms | Sleeps 8 | Mountain View________________________________________Kaanapali Alii 475 is a luxurious two-bedroom mountain view vacation rental nestled in the heart of Maui's renowned Kaanapali beach community. This spacious...
Newly Remodeled Penthouse w/ Stunning Ocean Views
Why Guests Love This Condo:- Ocean views from living area and massive private lanai- 5-minute walk to Kamaole Beach Park 1- Two King ensuite bedrooms — ideal for couples traveling together- 1,200 SF interior + 1,000 SF private lanai (exceptionally rare in Kihei)-...
Kaanapali Alii Unit 133
Kaanapali Alii 1333 Bedrooms | 2 Bathrooms | Sleeps 8 | Partial Ocean View_____________________________________________Welcome to Kaanapali Alii 133! A bright and inviting two-bedroom, partial ocean-view residence with a fully enclosed den that comfortably serves as a...
Maui Lahaina 2 Bedroom Villa Sleeps 6
Please Send An Inquiry Before Requesting To Book By Clicking The Contact Host Tab.This resort is located between North Ka’anapali Beach and the mountains of West Maui and features a heated lagoon pool, separate plunge pools, and a children’s sand bottom beach pool with...
Maui Vista 2216 Charming 1-bedroom condo in South Maui, perfect for a relaxing getaway!
Maui Vista 2216 Cozy Freshly Updated Condo Across the Street from the Beach in Sunny Kihei MauiWelcome to your Maui Retreat: This bright and comfortable 1-bedroom, 1-bathroom garden-view condo at Maui Vista offers a welcoming retreat in the heart of Kihei, South Maui...
Experience Maui's Magic at Westin Nanea: Luxury, Culture, and Oceanfront Bliss
Cozy yet spacious. Intimate yet extensive. This one-bedroom features luxurious comfort for memories together and space to escape.The Westin Nanea Ocean Villas is more than a resort; it’s an invitation to immerse yourself in the spirit of Maui. Nestled on the pristine...
ðº 7th-Floor Palms WaikÄ«kÄ« Studio | Street View | Prime Location
🌺 7th-Floor Palms WaikÄ«kÄ« Studio | Street View | Prime Locationâš ï¸ Building Notice: Spalling repair work will begin January 13 and is expected to continue for approximately 8 months. Work hours are Monday–Friday, 8:00 AM–4:30 PM (excluding weekends and holidays). Noise...
Fully renovated unit on the 14th Floor overlooking the surrounding Waikiki area!
1 Bedroom City View on the 14th Floor! Look no further, you've found PARADISE! This condo offers the comforts and conveniences of home. It is well maintained, reasonably priced and conveniently located in Waikiki. This updated condo has over 500 sq ft of living space...
Ocean Oasis steps away w/ private lagoon.
Welcome to your ocean front oasis. This cozy 1-bedroom condo offers stunning panoramic view of the Pacific Ocean right from your private lanai. Inside you will find a tastefully decorated living space with comfortable furnishing. the 1 bedroom features a plush queen...
Floor-to-Ceiling Oceanview Home with Full Sunset
*** Aloha! Welcome to our happy place! ***** Newly Remodeled Coastal Retreat, with Floor-to-Ceiling Ocean View **Welcome to our beach house, where every detail has been thoughtfully designed by a professional interior designer to create a serene, luxurious...
@ Marbella Lane – Ocean Breeze Lagoon front Stay
Summary:Discover a stunning lagoon-front retreat in the heart of Honolulu, Hawaii. This stylish studio APRT sits on the 19th floor and offers beautiful beach and ocean views. Inside, enjoy modern comforts including air conditioning, a fully equipped kitchen, and...
Luxe Maui Beach Retreat Walk to Kamaole Beach
Summary:Prime Location Steps to Kamaole Beach dining shops Luxury Comfort King bed memory foam sofa bed Resort Perks Pool hot tub outdoor grills Entertainment 65 Smart TV free Netflix fast WiFi Seamless Stay Self-check-in Smart Lock Exclusive Perks 1000 in local...
Kaanapali Alii 114
Kaanapali Alii 1141 Bedroom | 2 Bathrooms | Sleeps 4 | Garden View_________________________________________________________Welcome to Kaanapali Alii 114, a serene one-bedroom garden view condo nestled among the lush tropical landscape of Maui’s premier beachfront...
Waialua Beachside Cottage: Lovely! Direct Beach Access
Welcome to Kala‘iku Beach Cottage by Gather, your private seaside escape on Oahu’s North Shore. Offered as a monthly rental, this charming one-bedroom retreat blends beachside tranquility with island practicality—perfect for couples, small families, or remote-working...
Modern Elegant Studio w oceanviews..Royal Gardens
Elegant Studio at Royal Gardens Hotel Waikiki.....unit on the 20th floor offering panoramic views of Waikiki from mountain to ocean!Kitchenette is a plus for light preparation of meals promoting you to eat in.....Efficient and comfortable accommodations.Wyndham owners...
Westin Ka'anapali Ocean Resort Villas - OCEAN VIEW 1 Bedroom Villa
Luxury 1-Bedroom Ocean View Villa at Westin Ka’anapali Ocean ResortAvailability:7 nights from August 31 to September 7, 20257 nights from April 5 to April 12, 2026Enjoy a relaxing getaway at this stunning oceanfront resort on Maui’s west side, located on North...
Makaha Beauty - Condo in Hawaii with Ocean Views
A beautiful apartment with mountain and ocean views that is perfect for those that want to get away from the hustle and the bustle of Waikiki. The area is full of greenery and even has friendly residential peacocks that you might see near the parking area.Makaha is...
OAHU HAWAII OCEANFRONT HOME with POOL and BEAUTIFUL SUNSETS, WEST SIDE of ISLAND
NOTE: FOR SHORTER STAY PLEASE BOOK FOR 30 NIGHTS SO WE CAN DISCUSS RATE ADJUSTMENTS. (ADJUSTMENT WILL BE DRASTICALLY MADE)NOTE: OWNER/HOST CAN NOT SEE GUESTS CONTACT INFO UNTIL BOOKING IS MADE.NOTE: REMEMBER ANY BOOKING IS 100% REFUNDABLE IN FULL 14 DAYS PRIOR TO YOUR...
HawaiianBliss Spacious 2BR Marriott Ko Olina Villa for the Perfect Family Escape
**Available exclusively from August 7–14, 2026. A minimum 7-night stay is required.** Picture mornings with ocean breezes, afternoons by turquoise lagoons, and golden sunsets on the sand. Marriott Ko Olina Beach Club is a slice of paradise on Oahu’s sunny west coast....
KBM Resorts | FREE CAR | Kapalua Golf Villa | Ocean view | 1-Bedroom Condo with Gourmet Kitchen! KGV-24T1
** 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...
Kaanapali Alii | 481
Kaanapali Alii 4812 Bedrooms | 2 Bathrooms | Sleeps 4 | Partial Ocean View________________________________________Welcome to Kaanapali Alii 481, a beautifully remodeled one-bedroom residence with a fully enclosed den that comfortably serves as a second bedroom. Located...
Ocean View Beach Front Condo in Downtown Lahaina
Welcome to our home away from home in Downtown Lahaina! Wake up to the sounds of the ocean as you step out onto your lanai to take in the oceanfront views of West Maui. Enjoy all that Lahaina Shores Beach Resort offers- completely renovated since the fire 2 years ago...
Discovery Bay deluxe city view, near Ala Moana Shopping Center & the beach!
Welcome to your island escape in the sky! Located on the 24th floor of Discovery Bay, this beautifully renovated 1-bedroom, 1-bathroom condo offers 852 sq ft of comfortable living space and stunning views of Diamond Head, the city, and the lush mountains.Unit features:•...
Magic Skies Koi Pond View Handicap Accessible Room
With double doors leading to a koi pond on the main level this koi pond themed room is quaint and comforting. The room is fully handicap accessible with 36" doors, has a king size bed, a sitting chair, bench, no steps, private bathroom with tiled walk-in shower with...
Kapalua Bay Villas | 3 FREE Rental Cars | KBM Resorts | Panoramic Ocean Views | 3 Units, 4 Bedrooms | KBV ML-2077
** 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...
Waipouli Beach Resort E304 Ocean View 1 BD 2 BA
Wake up to sweeping ocean views from this beautiful one-bedroom condo, perfect for a relaxing getaway. Designed for two, it features a private lanai where you can soak in Kauai’s breathtaking coastline.Unit E304 Ocean View 1 Bedroom 2 Bathroom• Kitchen features granite...
Ground Floor Maui Sunset B105 on the oceanfront in Kihei
Watch the life of Maui unfold from the morning till evening from your private 114 sq foot patio. Ground floor means easy access to tropical gardens and the ocean beyond. Quiet location features large private view deck and renovated interior. Doesn't get any better....
Royal Kahana Maui 504 Ocean View Studio
Your peaceful ocean-view studio near Kaanapali Beach awaits—offering comfort, convenience, and stunning scenery for small families or couples. Unit 504 Ocean View Studio• 5th floor studio with balcony overlooking the ocean and view of the island of Molokai • Studio...
Ocean Front Pipeline Estate! Front row seat to the Pipeline Masters surf event!
Pipeline living at its best. A definite bucket list dream vacation destination. Facing directly at the famous Banzai Pipeline and Pipeline Backdoor, this home offers a unique spot to watch the most spectacular surfing waves in the world. This home offers all the...
Lahaina Shores 413 Breathtaking Beachfront Remodeled Studio
Lahaina Shores 413 NEW LISTING Experience Your Next Maui Oceanfront Escape in this Studio with Sweeping Views of the Pacific! FREE daily activities included with your stay value up to $570! Complimentary admission, every day of your stay*: Whale Watch (seasonal), Dinner...
Kapalua Bay Villas | 2 Free Rental Cars | KBM Resorts | Whale Watching | 2 Units, 3 Bedrooms | KBV ML-1598
** 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...
2 Oceanview Luxury Suites+ pool and Jacuzzi
Stay with us at this 3 Acre Luxury Vacation Rental Property with an Award Winning Coffee Farm comfortably nestled on the slopes of Hualalai overlooking Kailua-Kona.We offer Tesla Model Y rental. Enjoy exploring the island the eco-friendly way with autopilot,...
Waipouli Beach Resort A106 Oceanfront 2BD 3BA
Experience unmatched oceanfront living in this spacious two-bedroom condo. With sweeping views and direct beach access, it’s the perfect retreat for families or groups seeking a true Kauai paradise.Unit A106 Oceanfront 2 Bedroom 3 Bathroom• Extra-large floor plan...
Kaanapali Alii 2116
Welcome to Kaanapali Alii 2116, a luxury vacation rental nestled in the heart of Lahaina, Maui. This deluxe two-bedroom, two-bathroom condominium offers a serene escape with breathtaking views of the West Maui Mountains and lush greenery. Ideal for a family-friendly...
3BR/2BA New Build | Pool | W/D | Garage | Park
Welcome to this brand-new home: a spacious 3-bed, 2-bath, 1600 sqft retreat perfect for guests seeking ample space and a peaceful, safe neighborhood. Enjoy an open-concept living area with vaulted ceilings, extending to a covered lanai. The modern kitchen boasts sleek...
Find Zen in a Peaceful Garden Stay w/ Pool & Complimentary Yoga
Endless adventure awaits in Kailua-Kona! Whether you're staying for a day or a week, our hotel puts you close to top attractions, local dining, and must-see spots like the Amy B.H. Greenwell Ethnobotanical Garden and Pu'uhonua o Hōnaunau National Historical Park....
Beachfront Condo in Kihei!
Kick back and relax in this calm, stylish space. This condo features an upgraded interior that provides a comfortable and enjoyable stay. It is ideally located for easy access to the airport and nearby attractions, perfect for exploring the area. The condo is...
KBM Resorts | FREE CAR | Papakea | 1-Bedroom Condo with Beach Access! PKD-104
** 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...
Don't LET This ONE of a Kind Home Slip Through Your Fingers!
The custom ocean view home is a 5 bedroom, 4 bath residence with an extra TV room as well. The home has P/V to cut the electric bill. The pool and spa setting is like an oasis with a four step waterfall in the background. There is also an ocean/mountain view on the top...
Waikiki: Walking Distance 30 Night Minimum
Waikiki: Walking Distance 30 Night MinimumPrime Waikīkī Condo – 2BR with Pool, Balcony & Remote-Work ComfortEscape to paradise at this modern 2-bedroom, 1-bath Waikīkī vacation rental which is the perfect getaway for travelers and remote workers alike. Located in the...
Maui Resort Rentals: The Whaler 1257 - 12th Floor 1BR Penthouse w/ Stunning Ocean and Mountain Views!
Maui Resort Rentals is proud to present this stunning 1BR oceanview penthouse at the iconic Whaler resort on Kaanapali Beach. Newly launched on November 3rd, 2025 this penthouse is now open for reservations with availability beginning on February 13th, 2026!Suite 1257...
Ocean Front Condo, Modern & Bright
Location is key for our newly renovated 1 bedroom sunny South Kihei unit. Watch spectacular sunsets and whale watch from the comfort of your second story lanai. Experience island life at its best! Shopping, dining, surf lessons, and great beaches are all within walking...
The Lodge at Kukui‘ula - Bungalow 9
Nestled in the exclusive Kukui'ula resort on Kaua'i's stunning south shore, this luxurious one-bedroom bungalow offers an unparalleled Hawaiian retreat. Bungalow 9 seamlessly blends indoor and outdoor living, capturing the essence of island life in a sophisticated...
WAIMEA - Kamuela - Newly Renovated 2BR/2BA ʻOhana Home
He Hale ia no ke Aloha “A home that offers the chance to share in a reciprocal expression of ALOHA from the time you arrive to long after you leave.â€Whether youÊ»re a visitor or HawaiÊ»i resident planning a trip to HawaiÊ»i Island or looking for a home away from home for...
Waikiki Paradise Awaits! Relax with Pool, Rooftop Views, 2 Blocks to Beach!
Family-friendly property located just steps from the beachThis listing is for 2 separate rooms within a hotel. The price shown in the listing covers all 2 rooms.✦ Each room is 443 sq. ft, equipped with complimentary toiletries, kitchen with basic amenities, high...
Nihi Kai 201 Ocean Comfort
Summary:Enjoy oceanfront comfort just steps from Poipu Beach at Nihi Kai 201. This spacious two-level villa offers 1,507 sq. ft. of living space, beautiful ocean and pool views, multiple lanais, and easy access to Brennecke’s Beach. With resort amenities—including a...