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.
Rare 2 bed 2 bath with 10 minute walk to the pier, dining and Ocean!
Location location location! Perfect for couples or families. Located within walking distance of shops, activities, beaches, and amazing restaurants. This 2 bedroom, 2 bath condo is a perfect pick! Whether you’re strolling to fantastic restaurants for dinner or drinks...
Ocean Views, Updated Condo, Great Location MPS315
Beautiful remodel and ideal Kihei location create beachy perfection for your island getaway.Relax on your own huge lanai. Feel the wonderful trade winds and take in the island scents from the beautiful Plumeria trees and Hawaiian foliage. The lanai furnishings coupled...
NICELY REMODELED-2 BEDROOM WITH LOFT-OCEAN VIEWS-AC THROUGHOUT
Book With Confidence, This Nicely Updated 2 Bedroom Condo That Features A loft With An Additional Queen Sized Bed. This Condo Is Managed By PMI Maui, A Local Real Estate Brokerage That Specializes In Vacation Rentals. We Are Located Within A Mile Of The Resort And...
Wraparound Lanai - Direct Oceanfront View, sleeps 6, new A/C, free WIFI
Our fully central air conditioned condo unit 711 is beautifully appointed with island decor throughout. The master suite boasts a tropical trip-tic by a local artist. In addition, the dining and living areas also include original art. From the moment you step in the...
Maui Resort Rentals: Honua Kai Konea 214 - Upgraded 1BR w/ Extra-Large Balcony and Gorgeous Mountain Views!
One of the finest 1br mountain view suites available to rent at Honua Kai, Konea 214 is a luxurious upgraded 1br mountain view suite featuring a spacious floor plan, an extra-large balcony, and numerous upgrades throughout. From suite 214 your group will be treated to...
TOP FLOOR, OCEAN VIEW 2/2 WITH COOL SPLIT A/C
You're on the top floor of desirable "A" building with OCEAN & mountain views..SO CLOSE TO THE OCEAN YOU CAN HEAR THE WAVES! Decorated island style with traditional Hawaiian tapas and Tropical furniture...you will truly feel you are in Hawaii. We want you to fall in...
Ocean and Sunset Marina Views at the Ilikai Hotel w/Great Building Amenities
Book with confidence! This property is professionally managed by Ali'i Beach Rentals, an award-winning property management company.ILIKAI NOTICE — July 16, 2025Starting the week of July 2025, spalling repairs and full exterior painting of the building. Please be...
The Beach House - Closest House to Magic Sands Beach, Pool, Pickleball Court
Location, location, location. The Beach House is the closest rental house to Magics Beach and Magics Grill. Magic Sands Beach is the the most popular beach in town and gets its name from the fact that the sand comes and goes based on the waves. (Really big waves will...
Beautiful top floor condo w/ amazing view of Papohaku Beach
Hale Kamaluhia, Hawaiian for House of Serenity is our tropical retreat on the West coast of Molokai. Our desirable second floor condo has vaulted ceilings and is in one of the few buildings in the resort that has an unobstructed view of Papohaku Beach, one of the...
NUC 90/BB-0069, GE-014-134-8864-01, TA-014-134-8864-01
Start your day with a stroll on one of the most beautiful beaches in the world. Enjoy the sunrise in Kailua where your Hawaiian holiday truly begins. Kailua Beach is a perfect place to go to 'get-away-from-it-all.' Swim, boogie board, surf, kayak, sail, or windsurf in...
Gilligan's-secluded air-conditioned Cottage Near Gorgeous Beach--TVNC-4189
And not only secluded, but only a four and a half minute walk to a gorgeous and private beach! (I know VRBO wrote “six minute walk” in the title, but I measured it once!). Gilligan's Beach Cottage is not like one of the houses packed into town--it is about 15...
Kamaole Sands BUILDING ONE Ocean View- 2BR/2BA- Large Lanai & A/C THRU-OUT
GE/TA# 146897766401Maui temperatures seem to keep going up so please note Kama'ole Sands 1-405 has a "three zone split air conditioning system". When the trade winds aren't blowing, you'll be glad 1-405 will be a cool place for you to recharge for the next day!So,...
Luxury 2 bedrooms on Molokai
2 Bedroom 1.5 Bath & very rare 2 lanais with oceanviews - Sleeps 6 Gorgeous rare condo at Wavecrest with the luxury of 2 bedrooms, 1.5 baths and 2 separate lanais that both have views of ocean and beautiful tropical courtyard.Also, private FREE High Speed wifi for...
Sleeping Giant Cottage with Plunge Pool TNVC #1244
We're thrilled to share our house in Kauai with you! There's a swimming pool, botanical garden-like setting, and location that's extremely convenient for exploring the island. Our plunge pool is perfect for cooling off after a day at the beach or just lounging in all...
NEW! Top Floor Views with A/C in Poipu Beach, Resort Amenities
Top Floor Unit | A/C | 3 Minute Walk to BeachKiahuna 42 is a top floor unit (2nd floor) that is centrally located in the heart of the Kiahuna Plantation in Building 8. It has built in A/C and new furnishings and is only steps away from Poipu Beach!Enjoy free access to...
Pali Ke Kua 101 .. Stunning Ocean & Bali Hai Views
Near the edge of a bluff overlooking the ocean, this ground-floor condominium offers fabulous ocean and coastline views. Bali Hai, the landmark mountain made famous in "South Pacific," is just one of the awesome sights that guests enjoy here. Relax indoors or on your...
Oceanfront Sugar Beach Resort Penthouse 34. Amazing Ocean Views! Remodeled!
Welcome to Sugar Beach Resort Penthouse 34, one of the best ocean view condos in Maui. The top floor lanai is very private and looks out on endless ocean and 5 miles of white sandy beach - perfect for peaceful morning or evening walks. Watch the whales during whale...
BEACHFRONT HOUSE KIHEI, MAUI..TRUE HAWAIIAN HOME 1960's
This is a Private, BEACHFRONT Residence. PROPERTY IS FRONTED BY A HAND BUILT LAVA ROCK WALL. We offer you and your family a True Hawaiian Home, built in 1960. All of the charm still remains, although we have updated the interior, but preserved the integrity and special...
Top floor stunner! Gorgeous Views! Book Now for Summer!
West Maui Welcomes You Back. Our communities of Kaanapali, Honokowai, Kahana, Napili, and Kapalua; we all welcome you. Please have compassion and malama (care for) the island during your visit!For only the most discerning guest. This top floor stunner offers magnificent...
❤️PiH❤️Aloha Paradise ★ Large Private Heated Pool & Spa ★ PLUS Hilton Resort Pass
BROUGHT TO YOU BY PARADISE IN HAWAII LUXURY HOMESWelcome to Aloha Paradise, nestled in the stunning Ainamalu community of Waikoloa Beach resort – your perfect retreat on the big island.Aloha Paradise is an elegant single level home thoughtfully designed for comfort...
Maui Resort Rentals: The Whaler 720 - Luxurious 7th Floor 1BR w/ Gorgeous Ocean and West Maui Mountain Views!
Enjoy beautiful views of the Pacific Ocean and Maui's neighboring island Molokai, as well as views of the West Maui Mountains from this luxurious 1 bedroom suite at the iconic Whaler in the heart of Kaanapali Beach.Tastefully remodeled and featuring numerous upgrades,...
Hale Ma'ana Hou - Poipu Beachfront Home with A/C and Pool!
The Garden Island offers you this beautifully appointed, Mediterranean style home that is located on a protected white sand beach in sunny Poipu. The large, stylish, and open living room offers magnificent, ever-changing views of the Pacific Ocean with spectacular...
Newly Renovated Kahana Sunset ocean view
Summary:Kahana Sunsets is your place for an ocean front resort. This is a ground level condo with ocean views from the patio, bedroom and living room. This condo is fully renovated and all new items with many upgrades. Enjoy the secluded beach, BBQ's (either poolside or...
Maui Resort Rentals: Honua Kai Konea 408 - Spacious 2BR/1BA, Gorgeous Partial Ocean and Lush West Maui Mountain Views!
Unquestionably one of Honua Kai's best values, Konea 408 is a rare two bedroom, one bath suite that offers the space and privacy of an additional bedroom without the price tag of a standard two bedroom, two bathroom. Enjoy beautiful partial ocean views from its spacious...
Aloha Villas Resort | 12 Bed, 12.5 Bath
Aloha Villas Resort: Your Maui Oceanfront OasisDiscover ParadiseNestled on the picturesque South Maui coastline, Aloha Villas Resort offers a luxurious beachfront retreat for your next family gathering. This stunning 4-villa complex provides an unparalleled oceanfront...
Deluxe Top Floor Unit w/Ocean View-Maui Vista 2408
Premium upgrades, superior furnishings & charming decor make this condo a comfortable place to settle while on Maui. This vacation condo is so much more than just a place to sleep and cook, it will be your home away from home. Have breakfast on the lanai, take in the...
Extra spacious, private, 1BR/2BA, front row, ocean view at Maui Kamaole (A101)
Set on a grassy hilltop with expansive ocean views in beautiful South Kihei is Anthurium House at Maui Kamaole. Surrounded by lush tropical landscaping, this extra spacious (1,061 SF) 1BR/2BA ground floor condominium unit enjoys an unbeatable front row, end-unit...
North shore beachfront villa on Ke-iki beach
ALOHA!Welcome to our beachfront villa!This three bedroom home is located in a gated community fronting Ke-Iki beach, famous for its sand, surf and sunsets. It's also a great place to catch a glimpse of Humpback whales and spinner dolphins passing in the far-off waters....
Oceanview condo with 3 bedrooms, 3 1/2 baths and AC throughout
Enjoy captivating ocean views from this spacious 3 bedroom, 3-1/2 bath condo, where you can relax with spectacular sunsets on the lanai. There is air-conditioning throughout the condo, and you can control the temperature in each room individually. Our condo is on the...
Regency Villas 120 by Destination Kauai - Hale Maluhia Maikai, Central AC, Luxury Designer Condo
E komo mai, welcome to Hale Maluhia Maika'i!Hale Maluhia Maikai is a luxurious greenbelt property in Regency Villas at Poipu Kai with central air conditioning on the sunny south shore of Kauai. Spacious and bright with two stories and an open loft with vaulted ceilings....
SPECIAL DEALS! Hotel Room Studio - Direct Bali Hai & Hanalei Bay Ocean Views
Lovely and romantic, this popular honeymoon destination condo overlooks Bali Hai and Hanalei Bay. The room boasts a comfortable, four poster king size bed with designer bedding, large remodeled bathroom, a small sofa sleeper, and large slate covered private lanai for...
Family Friendly Home Walk to Beach Updated Kitchen! TVNC#1117
This is a legal vacation rental permit #TVNC 1117. Please see house rules or rental agreement for actual CANCELLATION POLICY and REFUNDS. We have a new kitchen refresh!! Pictures will be up in late Jan. 2024. Nestled among Kauai's tropical wild plant life, this...
Private luxury home with high ceilings and room for 6
Welcome to the Fairways, the upscale Townhouse community located in the exclusive Mauna Lani resort community on the Big Island of Hawaii. This private gated community offers beautifully appointed luxury homes with golf course views, vaulted ceilings and open floorplans...
Ocean view from every room in the condo!
Enjoy our condo in lovely Poipu with vast ocean views from the lanai and Master Bedroom. You will hear the ocean, see the ocean (and the whales in season) and be mesmerized by the ocean and the sea life. Sunset Kahili is the highest condo in the area. Our resort is on...
COMPLETELY REMODELED-AC THROUGHOUT-GROUND FLOOR-METICULOUS CLEANING
Book with confidence, this stunning, 2 bedroom, 2 bathroom (1200 sq. ft) condo that has been completely remodeled. This condo is managed by PMI Maui, a local Real Estate Brokerage that specializes in vacation rentals. We are located within a mile of the resort and...
The Best of the Best
Our condominium located at Kamaole Sands in sunny south Kihei has one of the superior garden/ocean views and is just steps from the Kamaole Beach III which is rated the top family beach in Hawaii by Sunset Magazine. This location is very protected from weather and...
Poipu Oceanfront Dream Getaway at Kuhio Shores! 30 feet from the waters edge!!!
Hawaii Tax ID# TA-034-303-5904-01 and GE-034-303-5904-01New! Air Conditioning!Thirty feet from the waters edge, our spectacular oceanfront, ground floor, one bedroom, Poipu condo, has fantastic snorkeling, famous surf spots, and incredible sunsets. Everything you desire...
3 bedroom with central A/C at Fariways at Mauna Lani #1705!
You, along with your family and friends, will make wonderful memories at this spacious, well-appointed townhome located in the quiet gated community of The Fairways at Mauna Lani. North of the Kona International Airport, on the sunny Kohala Coast, this townhome is...
Top Floor corner unit in main building !
Treat yourself to the ultimate in tropical island luxury with a stay at this beachside condominium. This luxury condominium offers access to two close elevators and is an end unit.Situated inside the brand new Waipouli Beach Resort and Spa, this condominium is fully...
Ocean View South Maui Condo with Lanai plus FREE parking, Wifi and Smart TVs
Condo with Ocean views from lanai, living room and kitchen. One bedroom (KING bed) , one bathroom (walk in shower), Lanai with seating to enjoy the gorgeous ocean views in South Kihei, Maui. Walk across the street to Kamaole II beach. Proximity to restaurants, shops,...
*Makani A Kai B9* Maui Condo Steps To The Sand!
This 2nd story beach front condo offers direct beach access from complex grounds with views of the breathtaking Maalaea Bay, the grand volcano Haleakala and the sparkling Kihei lights at night. Enjoy your private lanai. The loft style primary bedroom features a king...
Brand New Pool For Your Best Family Vacation!
Aloha and E Komo Mai! Welcome to the Hale Ohana Kauai (Family House) in beautiful North Shore of Kauai, nestled in the premier resort area of Princeville.New luxurious pool and spa for the whole family. This tropical retreat is a bright and spacious home and is...
Newly Renovated Closest to Ho'olei Pool, Wailea Beach, the Grand, Fitness Center
One of a kind four bedroom Ho'olei home in Wailea!Breathtaking is the best word to describe this luxury townhouse-style villa at Ho’olei, situated in beautiful Wailea on the sunny, southwestern shore of Maui. Ho’olei is the ultimate dream home in paradise!This...
Minutes from Downtown Hilo, Sleeps 6
Welcome to Hilo Hale Kaumana! Minutes from Downtown Hilo, this home has everything you need for that getaway to the Big Island. Sleeps 6This fully renovated and beautifully decorated 3 bedroom, 2 bath home is the relaxing retreat you’ve been seeking. The quiet...
Ma'alaea Surf, Unit G10, 2BR Beachfront Condo, AC, Wifi, Pool, TV, Kitchen
Ma'alaea Surf, Unit G10 is a two story townhouse unit with vaulted ceilings. This unit has a large lanai, stunning ocean views and overlooks the large pool and shuffleboard court. This elegant unit features a gorgeous fully furnished kitchen and is equipped with central...
Garden Villa l Two Lanais, A/C, Pool
Summary:H223 | TA-142-481-4080-01Immerse yourself in paradise at Villa H223, a stunning 4-bedroom Garden Villa at Poipu Kai. With central A/C, stainless steel appliances, and designer furnishings, this villa offers unmatched comfort and style. Relax on two private...
Maui Resort Rentals: Honua Kai Hokulani 606 - Large 6th Floor 2BR, Corner Floor Plan w/ Direct Ocean & Mountain Views
Located in one of the closest 2 bedroom columns to the ocean at the entire resort, Hokulani 606 boasts direct 6th-floor ocean views AND lush West Maui Mountain views from its prime corner location.Suite 606 affords a perfect opportunity to gather, reconnect, and...
Luxury Upgraded Condo #98, AC, Poipu Beach, Partial Ocean View
Air Conditioned? Yes!!!Only few condos at Kiahuna are Air Conditioned. We are excited to announce that as of Sep. 2, 2021, our condo is fully air conditioned.Kiahuna Resort is 35 acres of landscaped, manicured lawns and gardens. This oceanfront resort is just steps away...
Mika Kai 4 bd w/Pool and Hot Tub - Epic Spot for Whale Watching!!!
Fully Licensed Short Term RentalSTVR-19-344467/NUC-19-255GE-131-303-1680-01TA-131-303-1680-01Each guest will be asked to sign a rental agreement after booking is accepted. Fabulous furnishings and upgrades to this already beautiful house.Here is the base of operation...
11th Floor Oceanview Sunny Studio 1115! 5 Star Reviews!
Aloha from the gorgeous sunny studio Whaler #1115 at The Whaler on Ka'anapali Beach. Whaler 1115 is located on the 11th floor on the sunny courtyard side of Tower I, the north tower. This fully remodeled interior features an open kitchen with an oversized granite...