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.
Sunset views await in this 2-bed, 2-bath condo! Golf course vistas + room for 6!
Make memories at Keauhou Punahele Unit C104: two-bedroom, two-bathroom home, and a newly remodeled kitchen. A smart television in both bedrooms, and a fully stocked kitchen. Relax on your lanai and enjoy the BBQ.This two-bedroom, two-bathroom home has all one needs on a...
Amazing ocean and sunset views
This beautiful guest house is located on Maili Point, one of Oahu's most scenic sites. Maili Point is located on the dry and sunny west side of Oahu giving days of perfect weather, full of sunshine and trade winds. The property's secluded location provides a relaxing...
Lovely Condo w/ Garden Views, AC & Shared Oceanfront Pool: Casa De Emdeko 222
Casa De Emdeko 222 is a charming oceanfront retreat on the Big Island, offering a blend of comfort, convenience, and authentic island ambiance. Located just two miles from historic Kailua-Kona Village and set within a lushly landscaped complex, this second-floor condo...
Hale Kamaole 313 Third floor condo, partial view of the ocean!
This two bedroom condo has a good Ocean and Garden View. Master bedroom has a King bed. Down stairs bedroom has two twin extra long beds. Pull out sofa bed in living room. Spacious kitchen cabinets. Carpet in bedrooms and tile floor. New A/Cs and ceiling fans. This...
New Listing! Breathtaking views,Unforgettable Stay
Welcome to Nohonani 401 – Your Oceanfront Escape in Paradise! Step into serenity at Nohonani 401, a beautifully appointed 2-bedroom, 2-bath condo on the 4th floor, showcasing stunning oceanfront views that stretch endlessly across the Pacific. This peaceful retreat...
Ocean Front Newly Renovated Unit 415 with stunning views! - 1 Bedroom/1Bath
** Newly Renovated! Discounted 2025 Rates! - Book your stay at Kuleana Unit 415 TODAY!! Unit 415 at Kuleana has recently undergone a comprehensive renovation, resulting in an ideal option for your upcoming vacation. This modern one-bedroom, one-bathroom oceanfront condo...
*Ocean and Mountain Views!* | Lush Hawaiian Oasis
Summary:🌴 Wake up in paradise at Hanalei Bay Resort! Nestled on 20 lush acres in Princeville, this luxury condo offers ocean & mountain views, private beach access, pools, tennis courts, yoga, spa, BBQs & more. Golf lovers enjoy exclusive discounts too! Your dream...
The HALE, perfect Family Base Camp, centrally located, short walk to the beach
This property is located on a quiet street across from the Morman Temple. The property consists of a Front Cottage, The Hale (where this unit is located) and a parking lot for the Hale Renter and the Owners (who live 0n site). We are close to town (5-7min walk) the...
KPL 8 Remodeled 2BD Home Ocean Views Near Beach
Kaanapali Plantation 8 Beautifully Remodeled 2Bedroom with Ocean & Sunset Views Just Minutes to the Beach! FREE daily activities included with your stay value up to $570! Complimentary admission, every day of your stay*: Whale Watch (seasonal), Dinner Sunset Sail,...
OCEANFRONTopFloor@5k mo w APRIL start&6monthSave 1k more!HEATED POOL, hottub&gym
OCEANFRONT COMPLEX Maui Sunset TOP FLOOR 5 OCEANVIEW &2 Bathrooms Start4/19@this top floor condoOPEN April for full month booking preferred, buy 3 months &next months half off! Vrbo won’t allow same-day bookings but I have a keyless entry pad SAME DAY BOOKING OK!- so...
Gorgeous Waikiki Ocean View! Full Kitchen, Free Parking, Close to Beach!
Waikiki Sunset #3704 – 229 Paoakalani Ave.Fabulous views of the Pacific Ocean, Diamond Head and Kapiolani Park from this 37th floor, one-bedroom condo (564 sqft plus 67-sqft lanai with table and chairs) with central AC. 4-person max.Just a 10-minute walk to the best...
Beautiful Fairways Condo near Disney’s Aulani, Four Seasons, Lagoons and Golf
Newly renovated and ready for you to enjoy your fabulous vacation in Hawaii. Stay far away from the crowds of Waikiki. Easy drive from the airport and less traffic than the drive to Honolulu. Enjoy the same beach lagoons as the guests at the resorts at Ko Olina but in a...
Oceanview Oceanfront 2BR/2BA
Fabulous West Maui oceanfront location. Polynesian Shores is a low rise, low density oceanfront community on 2 lush acres with a total of only 52 units. Conveniently located near world class golf courses, beaches, and restaurants, 5 min. to Kanaapali and 10 min. to...
KAMAOLE SANDS BLDG 4 - PARTIAL OCEAN VIEW, OCEAN/POOL CLOSE, LARGE LANAI
Aloha, and a warm welcome to our spacious (818 sq ft) condo located in the Kamaole Sands Resort located in South Kihei directly across the street from the famous Kamaole Beach Park III. The condo is located in building 4 on the third floor, away from the busy part of...
South Maui Partial ocean views Maui Sunset A112 1 BR, 2BA
Immerse yourself in the South Maui Sunset. This beautiful one bedroom, two bath condo is located on the ground floor with partial ocean views. Maui Sunset is 5 acre Ocean front property, with lush green lawns throughout the property. Relax in the well appointed living...
Charming Studio In Waikiki - Minutes to the Beach!
Construction Notice 10/20/25: Exterior spall working is currently scheduled for 9/8 - 11/7/25 and painting work is currently scheduled from 6/15 - 7/10/26. During this time, the lanai will be locked and not accessible to guests. For your safety, please do not attempt to...
2-Bedroom Garden & Ocean Views!
Welcome to your slice of paradise! After your long journey, we know you will be ready to unwind. To make your arrival extra special, we have prepared an Aloha Basket filled with snacks and coffee, so you can relax right away.This spacious single level 2-bedroom,...
Exquisite condo situated on Kaanapali Beach
Welcome to Kaanapali Shores 223, a 2-bedroom, 2-bathroom condo that offers central A/C, a private washer/dryer, and high-speed Wi-Fi. This property has elevators. Unit 223 can accommodate up to 6 guests. The master bedroom is a tranquil retreat, offering a king-sized...
Oceanview, Renovated and Gated, Private Lanai
Beautiful ocean views greet you upon entering this 3rd floor unit at Lae Nani. Recently renovated with a fresh and light decor and new laminate floors in May 2025! This 1 bedroom, 1.5 bath unit with comfy King Sized Bed has a lanai out front to enjoy that oceanview...
Hale Hui Kai 102 on Keawakapu Beach
This private garden condo is on the first floor of the south side of the building ...about 60 steps along the pathway leads to the gem of south Maui, Keawakapu Beach!Keawakapu Beach, located on the south shore of Maui, Hawaii, is known for its stunning natural beauty...
Legal Short Term on North Shore Oahu, Upper Floor - Kuilima Estates
We welcome short term rentals Welcome to this nicely updated two bedroom condo located on the peaceful East side of Kuilima Estates at Turtle Bay. The condo features brand new tile flooring in the living room and kitchen along with new kitchen cabinetry!This unit has a...
Emmalani Court 523 By Parrish Kauai - Great views & Princeville Location
Enjoy this luxurious Kauai condo next to the Makai Golf Course at Princeville Resort. This small resort features only 42 units, pool, spa and outdoor barbecue area. Conveniently located near our North Shore office at the Princeville Resort Center. Stop by and meet our...
Kauai 2 BR/2 BA Condominium Oceanfront - Pono Kai Resort!
Enjoy beautiful sunrises and all the luxuries that accompany beach side living. This two-bedroom ground floor condominium in Pono Kai is steps from a mile-long, sandy beach. This beautiful condominium has been privately owned, cared for, and enjoyed by us for many...
Pili Mai 2-Bedroom, 2 bath, A/C Condo unit 11G, Sleeps 6
Two bedrooms plus loft, 1 king bed, 1 queen, plus 2 twins in the loft, 2 full bathrooms, nice upgrades, washer and dryer in unit, lanai space, incredible views, great complex amenities.This brand new 2 Bedroom plus loft, 2 Baths condo is ready for your next vacation...
Ali'i Point #5: Spacious 3 BR Kona Oceanfont Villa with A/C
Ali'i Point #5 is located at Ali'i Point, a private and gated community of 16 seaside homes with community pool and tennis court.Central A/C throughout. Main floor has living room, dining room, kitchen, half bath, and master king bedroom with en suite bathroom.Large...
Top floor-quiet, 3 min walk to beach, Espresso machine, pool/ fitness, HBO
Feel like living in a treehouse…Quiet, top flor location, lots of special features *** Pls note that from Jan1st, 2024, for stays the end cleaning fee for each unit 1 BR is $ 268.00 plus Tax. For stays of 10 nights or more, an additional mid-stay replenishment fee per...
KONA MAGIC SANDS#309 TOP FLOOR DIRECT BEACHFRONT, AIR CONDITIONING!!
*LOOK NO FURTHER! YOU HAVE FOUND AN INCREDIBLE PROPERTY!**Kona Magic Sands#309 is a DIRECT oceanfront, Top floor condo that is meticulously maintained, beautifully furnished, and has absolutely anything any guest could dream of. Air Conditioning, Wifi, beach gear,...
BEAUTIFUL.... Keauhou Ocean View Condo
Capture the essence of Hawaii with ever present ocean view, trade winds, palm trees , birds, and lovely flowers. All things Hawaii. The condo is filled with natural light and always present ocean breezes eliminate the need for air conditioning! This ”bridge unit” is...
White Sands Village #120
Summary:Say aloha to your Big Island vacation rental! White Sands Village is an oceanfront condo complex in the gorgeous town of Kailua-Kona. Maximum occupancy strictly enforced in accordance with local ordinances.The Space:Guests will find themselves in the perfect...
Honu Cottage: Quiet, Oceanfront Comfort + EPIC VIEWS!
WE ARE LITERALLY ON THE WATER! E Komo Mai (Welcome) to Paradise!one rental per 30 day period as required by city & county law Honu Hale is a charming island-style cottage that sleeps 3 adults or 2 adults and 2 children. A cozy loft bedroom has a comfortable king size...
Second floor, Great Ocean view #260
Great second floor unit , with Ocean views, and views of the garden This is are little peace of paradise, pool and spa tiki bar This studio has newqueen bed , mini fridge, BBQs , full bathroom, microwave , coffee maker, dishes for four complete BBQs set , This condo is...
Oceanfront ground-floor condo with amazing views, pool, & full kitchen -walkable
Kapa'a Sands 12Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'This boutique establishment is right on the ocean, enveloped in lush tropical gardens with everything you need for your...
Poipu Makai Villas C1 - Amazing Views, Ocean Front, AC
POIPU MAKAI C1 AT KOLOA KAI VACATION RENTALSYour Oceanfront Oasis on Kauai’s South ShoreDiscover unparalleled tranquility and breathtaking ocean views at Poipu Makai C1, an exclusive oceanfront condo perched on a bluff overlooking the vibrant blue Pacific. With only...
Kaha Lani Resort #114, Ocean View, Steps to Beach, Sunrise, Pool/Wi-fi
Kaha Lani Resort #114, Beachfront Resort, Wailua, Kauai. Ocean view, ground floor end unit on a beachfront resort. Surrounded by parks, a golf course and the ocean. Beach towels, beach chairs, beach umbrella and a small cooler are provided for your use during your stay....
Updated 1-bed, 1.5-bath with mountain views near beaches and dining
Be our guest at The Shores, on the sunny Waikoloa Resort coast. This one-bedroom one-and-a-half-bath, newly updated condo features a fully stocked kitchen, sweeping mountain views, and close proximity to numerous white sand beaches. Enjoy a multitude of dining options,...
Perch - Kamaole Beach Club: Oceanview upgraded one bedroom, walk to beach
Walk across the street to the best beach in Maui! This ocean view ground floor condo is the best location in the complex. Nicely updated in 2022, this one bedroom unit features travertine floors, crown molding, granite kitchen counters in the kitchen, stainless steel...
EL K102 Spacious Kaanapali Condo Relax Recharge Pool AC
Eldorado K102 1bedroom/2bath Relax, Restore and Unwind. Enjoy Resort Life at its Best! FREE daily activities included with your stay value up to $570! Complimentary admission, every day of your stay*: Whale Watch (seasonal), Dinner Sunset Sail, Snorkel Sail, Alpaca Farm...
Kihei, Maui Ground Floor Tropical Getaway - Across street from beach
Ground floor condo in the heart of South Kihei on the beautiful island of Maui. We welcome you to stay at our cute, clean, well-cared for condo during your visit to the Valley Isle. Directly across the street from Kamaole Beach Park II, a beautiful golden sand beach...
Fantastic Beach Front Villa
Following Oahu laws a 30 minimum lease required for any rental. Please inquire about it.Right on renowned Kailua beach, our beachfront villa equipped with a pool and jacuzzi is perfect for all your vacation needs. Wake up and go watch the sunrise or a morning jog. The...
Beachside Kihei Vacation Rental w/ Stunning Views!
Book this airy corner vacation rental condo for an incredible stay in Kihei, Maui!! Nestled in Leina’ala Condominiums, this unit offers access to a shared pool and tennis courts, and is just a short stroll to the beach. Not to mention, the beach is in your front yard...
Help West Maui Business Owners - Reduced Winter/Spring Rates! Papakea C105
With so much to enjoy on the resort grounds or within a short walk, a little planning goes a long way toward affordability on Maui: Dine at one of many local restaurants, catch happy hour and some of the best live music on Maui, all within a few hundred yards of our...
Spacious and Peaceful Corner Unit at Fairway Villas
Please note, effective Jan 1st. 2026, Hawaii`s Transient Accommodations Tax will increase from 10.25% to 11% for all stays with an arrival in 2026 forward. We may need to collect the tax difference to secure and finalize your booking. We will contact you to confirm the...
Maui Banyan P304 - Remodeled, Partial Ocean View, AC, Across from Kamaole Beach!
You will LOVE this 1BR/1BA Luxurious, ceiling to floor totally remodeled single level floor plan. While you dine on your balcony, enjoy the partial ocean and mountain view. This condo is located on the cooler side of the building. The Maui Banyan is a Premier...
Kiahuna 106 - Ocean View, Close to World-Class Beach, Poipu Beach Club Included
KIAHUNA PLANTATION 106 AT KOLOA KAI VACATION RENTALSOcean-View Condo in the Heart of Poipu’s Tropical ParadiseNestled on 35 acres of lush lawns and tropical gardens, Kiahuna Plantation 106 offers the perfect combination of history, charm, and modern comforts. This...
Nihi Kai 510 - Garden w/ Ocean Peek View/AC/Walk to Beaches
NIHI KAI 510 AT KOLOA KAI VACATION RENTALSYour Garden View Escape in the Heart of PoipuWelcome to Nihi Kai 510, a beautifully updated 2-bedroom, 2-bathroom condo in the heart of Poipu. Located within walking distance to Brennecke’s Beach and Poipu Beach, this charming...
Oceanfront 2BD/2BA Sugar Beach Tranquility at Koa Lagoon
For the sun worshiper South Maui is the driest, hottest, and most popular coastline on the island. One glance at the 180 degree view from this beautiful, tranquil spot with its spacious 2 bedroom/2 bath condo at Koa Lagoon and you know you have the perfect spot for your...
2-story, spacious layout steps from pool, near beach.
Welcome to Hale 'Olu'Olu, a stunning 2-level condo nestled in the renowned Waikoloa Beach Resort, offering an idyllic retreat for families and groups. This home has a breathtaking views of the golf course and majestic mountains, with easy access to sandy beaches,...
Ground floor condo w/ lanai, shared pools, & hot tub - near beaches & golf
Honua Kai - Hokulani 110Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Welcome home to this nicely updated, bright, and spacious condo located in the heart of Ka'anapali. Enjoy your...
4 bedroom, 2.5 bath, Sleeps 9 in beds
DUE TO BILL 41 we are only allowed to rent one time in a 30 day period so our minimum bookings will be 30 days or longer. We have been waiting to remodel this home, but first the pandemic made it difficult with not being able to travel, and now the 90 day rule, so not...
Idyllic island gem with pool, beach access, high-speed WiFi & central AC
Ilikai Hotel 838Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Get away from the mundane and let all of life's worries slip away here on the beautiful island of Honolulu. Whether...