Hawaii Vacation Rentals – Explore Island Homes, Beach Condos & Luxury Villas

Planning a getaway to the Hawaiian Islands? Whether you're dreaming of waking up to ocean views in a beachfront condo or relaxing in a private villa surrounded by lush tropical gardens, Hawaii offers vacation rentals to match every traveler’s style. From the golden sands of Maui to the serene shores of Kauai, and the adventure-filled landscapes of the Big Island to the vibrant energy of Oahu, each island invites you to discover its unique charm.

Choose from a variety of accommodations including luxury villas, cozy bungalows, oceanfront homes, and resort-style condos with full amenities. Ideal for couples, families, and groups, these rentals provide the perfect base for exploring nearby beaches, cultural landmarks, hiking trails, and snorkeling spots. Enjoy the freedom of a private stay with space to unwind and all the comforts of home.

Each listing is curated with detailed descriptions and high-quality photos, helping you find a place that fits your needs and budget. Whether you're booking your first trip or returning for another island adventure, your perfect Hawaiian escape begins with the right accommodations. Start browsing on To-Hawaii.com and turn your vacation plans into unforgettable memories.

Elegant Punahele Penthouse Condo in Kailua-Kona

Punahele Penthouse Condo will fast become your favorite place to stay in Kailua-Kona! Punahele Penthouse is on the 7th (top) floor of the Kona Ali'i Condo Complex which is located in the heart of Kailua-Kona. You're within walking distance to ...

  • 2 bedroom
  • 2 bathroom
  • Sleeps 6
Hawaii> Kailua-Kona
from $504 
View Property    

Lae Nani Condo Kauai Beachfront Retreat

Paradise awaits you in this beautiful ground floor, one-bedroom, two-full-bath Lae Nani Condo, Unit #317 on the beautiful Garden Isle of Kauai!

Located on Kauai’s beautiful Coconut Coast (East side), this Condo has all the amenities you...

  • 1 bedroom
  • 4 bathroom
  • Sleeps 4
Hawaii> Kapaa
from $306 
View Property    

Luxury Hawaii Private Estate with Ocean Views

Guests walk in and we see wow on their faces...gourmet kitchen, ocean views, huge bedrooms.

"perfect for a family reunion"
"cool at night was just right"
"close to the best beach in Hawaii"
"your own private estate"
"amazing...

  • 6 bedroom
  • 6 bathroom
  • Sleeps 18
Hawaii> Kailua-Kona
from $1,020 
View Property    

Charming North Shore Maui Home near Haleakala


We invite you to stay in our peaceful home on the North Shore of Maui, within walking distance to a local coffee shop, small grocery and near the Road to Hana and Haleakala. Only available to book with the owner Amy - Beware of scammers ...

  • 2 bedroom
  • 1 bathroom
  • Sleeps 5
Hawaii> Haiku
from $395 
View Property    

Oceanfront Maui Condo with Beach Access and Views

Dream your most desired vacation. Then come to magical Maui, one of the world’s most elite vacation destinations. How better to experience our island than by renting from an owner who has combined her own personal getaway with the conveniences...

  • 1 bedroom
  • 1 bathroom
  • Sleeps 2
Hawaii> Maalaea
from $343 
View Property    

Beautiful Ground Floor Corner Unit Near Private Beach in Maui


This most sought after location in the complex is a ground floor corner unit offering privacy and just 10 paces away from one of the two almost private beaches, where you may find yourself alone.(Be aware that the beaches are subject to ...

  • 1 bedroom
  • 1 bathroom
  • Sleeps 2
Hawaii> Lahaina
from $401 
View Property    

Spacious Family Vacation Home in Princeville Kauai

Discover your family’s ideal getaway in the heart of Princeville at Hanalei, Kauai! Our spacious vacation rental offers a tranquil oasis surrounded by lush landscapes and tranquil gardens. Designed for relaxation and connection, this private ...

  • 4 bedroom
  • 3 bathroom
  • Sleeps 6
Hawaii> Princeville
from $620 
View Property    

Stunning Oceanfront 2BR Condo with Unbeatable Views

Gorgeous, completely upgraded oceanfront/oceanview 2 bedroom, 2 bath. This condo is exquisite and has been meticulously renovated for the discriminating traveler. Huge, unobstructed ocean and island views from the living room, lanai and master ...

  • 3 bedroom
  • 2 bathroom
  • Sleeps 6
Hawaii> Kihei
from $366 
View Property    

Hawaii Kona Beachfront Penthouse with Snorkeling Access

Love to snorkel and want to see over 100 species of tropical fish & turtles? Then why not stay right across the street from Hawaii's best snorkeling beach?! Our modern beachfront unit offers gorgeous ocean/sunset views and the easiest access ...

  • 2 bedroom
  • 2 bathroom
  • Sleeps 4
Hawaii> Kailua-Kona
from $404 
View Property    

Beautiful Ocean View 2-Bedroom Condo in Maui

Kauhale Makai (Village by the Sea) truly embodies paradise. This newly remodeled 2-bedroom, 2-bathroom condo has been beautifully updated, boasting a brand-new kitchen complete with granite countertops and high-end appliances.

The ...

  • 2 bedroom
  • 2 bathroom
  • Sleeps 6
Hawaii> Kihei
from $388 
View Property    

Beautiful Maui Beachfront 2BR/2BA Vacation Home

ALOHA. Come vacation in our beautiful, newly remodeled 2BR/2BA beachfront home. Enjoy the breathtaking views of Kaho’olawe Island, Molokini Crater, the West Maui Mountains and of course the pristine Pacific Ocean and its shoreline. Sugar ...

  • 2 bedroom
  • 2 bathroom
  • Sleeps 4
Hawaii> Kihei
from $526 
View Property    

Modern Kailua Beachside Suite with Mountain Views

"In order to comply with Oahu's 30 day minimum short term rental laws, we may not advertise to rent for a period shorter than 30 days."

Come enjoy island life while staying in our newly built, 600 sq. ft. upstairs suite. Beautifully ...
Registration Number: 420200410000, TA-071-652-3520-01, GE-071-652-3520-01

  • 1 bedroom
  • 1 bathroom
  • Sleeps 2
Hawaii> Kailua
from $212 
View Property    

Luxury Oceanfront Condo at Luana Kai Maui



Make your trip to Maui more memorable with a stay at our 5 star condo at Luana Kai. Luana Kai is a beautiful resort with immaculate grounds in a park like setting, ocean front in sunny Kihei with no busy roads to cross to get to the ...

  • 2 bedroom
  • 2 bathroom
  • Sleeps 6
Hawaii> Kihei
from $384 
View Property    

Beautiful End Unit Condo with Garden Lanai and Pool Access

This is an end unit on the first floor at the back of the resort complex. You can enjoy the lush gardens and tropical breezes from the spacious lanai. The newly renovated condo has a master bedroom that includes a king size bed. The main living ...

  • 2 bedroom
  • 1 bathroom
  • Sleeps 4
Hawaii> Kihei
from $265 
View Property    

Charming Lana'i Artist's House with Ocean Views

The Artists House, Permit # STLA 2017/0002 is a home away from home with the comfortable furnishings and great amenities. The fabulous Lana'i sunsets can be enjoyed outside on the deck where there is glass dining room table with 6 chairs and bbq...

  • 3 bedroom
  • 3 bathroom
  • Sleeps 4
Hawaii> Lanai
from $781 
View Property    

Luxury Beach Tower Villa in Ko Olina

This large corner villa is located inside the Beach Tower, the closest building to the beach (20ft walk from your condo to the beach lagoon).
Promo: Book 7 Nights and you will receive the 8th Night Complimentary (dates may vary based on the ...
Registration Number: TA-134-204-4160-01, GE-134-204-4160-01, 1910570090191

  • 2 bedroom
  • 2 bathroom
  • Sleeps 6
Hawaii> Kapolei
from $932 
View Property    

Emmalani Court Princeville Vacation Rental with Heated Pool

Emmalani court is a small, quiet complex in Princeville, near the Princeville Resort. After visiting the 4 main islands in Hawaii, we decided on the North shore for it's lush setting and laid back vibe. There is truly no other place like it in ...

  • 2 bedroom
  • 2 bathroom
  • Sleeps 6
Hawaii> Princeville
from $419 
View Property    

Sunset in Paradise - Oceanfront Kailua-Kona Condo

Enjoy breathtaking sunset views every night from this beautifully updated condo steps from Downtown Kailua-Kona village with AC in both the living room and bedroom.

Sunset in Paradise is your private paradise with gorgeous ocean views ...

  • 1 bedroom
  • 1 bathroom
  • Sleeps 4
Hawaii> Kailua-Kona
from $326 
View Property    

Luxury 2-Bedroom Mauna Lani Vacation Home

Welcome to Unit 1604 at the Fairways at Mauna Lani! This is the largest 1646 SF 2 bedroom floor plan where both bedrooms are located upstairs providing a peaceful sleeping area separate from the living area downstairs. They each have their own...

  • 3 bedroom
  • 3 bathroom
  • Sleeps 6
Hawaii> Waimea
from $407 
View Property    

Holualoa Ocean View Cottage on Big Island

We are located on the west side of the Big Island of Hawaii, directly above Kailua-Kona, on the side of Mt Hualalai, in Holualoa, with an awesome ocean and coastline view! Please read our reviews because the view from the cottage lanai is better...

  • 1 bedroom
  • 1 bathroom
  • Sleeps 2
Hawaii> Holualoa
from $224 
View Property    

Hale Lanui Ocean View Vacation Home with Pool

Hale Lanui is located across the street from the ocean and has sweeping unobstructed views of the ocean and sunsets. This two story 2700 SF home is located on a residential street and has a swimming pool (lots of beach towels) and Jacuzzi for ...

  • 4 bedroom
  • 3 bathroom
  • Sleeps 10
Hawaii> Kihei
from $1,480 
View Property    

Oceanfront Hawaii Condo with Lanai and Stunning Views

Our comfortable, fourth-floor, south shore condo is right ON the ocean so you will SEE --and HEAR-- the sound of the surf as soon as you open your front door. The condo, with stylish, contemporary furniture, boasts a comfortable king-size bed. ...

  • 1 bedroom
  • 1 bathroom
  • Sleeps 2
Hawaii> poipu
from $511 
View Property    

Luxury 3BR Kona Beach Home with Pool & Ocean Views

This breathtaking 3 Bedroom plus bunkroom, 2 bath single level home is located just minutes from Kailua, Kona and some of the most beautiful beaches in Hawaii. Everything in this house is new! Fresh full remodel just completed. This includes a ...

  • 4 bedroom
  • 2 bathroom
  • Sleeps 8
Hawaii> Kailua-Kona
from $892 
View Property    

Luxury Mauna Lani Fairways Unit 1602 with Beach Access

Welcome to Unit 1602 at the Fairways at Mauna Lani! This luxurious gated community is located between the Fairmont Orchid and Mauna Lani Bay Hotel. This is a bright and open unit in a park-like setting. Feels like your own backyard. Easy ...

  • 4 bedroom
  • 3 bathroom
  • Sleeps 8
Hawaii> Waimea
from $518 
View Property    

Honu Villa at Mauna Lani - Private Hawaiian Retreat

Our Honu Villa in the Villages at Mauna Lani is a private one-level Hawaiian Kahili home filled with everything you need for a Hawaiian vacation including your own pool and spa, and nearby beach! We are members of the Mauna Lani Resort Golf ...

  • 3 bedroom
  • 4 bathroom
  • Sleeps 8
Hawaii> Kamuela
from $1,325 
View Property    

Milowai Maalaea Oceanfront Condo with Modern Upgrades

Hosted by VacaMaui

We chose Milowai in Maalaea due to it's fantastic convenient and direct oceanfront location. It is only 20 minutes to almost anywhere on the Island and we love to see and do it all.

The unit is on the ground ...

  • 2 bedroom
  • 1 bathroom
  • Sleeps 4
Hawaii> Wailuke
from $414 
View Property    

Elegant Ocean View Golf Course Condo in Hawaii

Our unit is spacious with high ceilings, ceiling fans, fabulous sunlight, and gorgeous ocean views. This elevated third story unit affords a wonderful lanai with a view overlooking manicured golf courses, tropical flowers, natural lava ...

  • 3 bedroom
  • 3 bathroom
  • Sleeps 6
Hawaii> Kailua-Kona
from $312 
View Property    

Hale Mala Pua Garden Home Near Botanical Gardens

Hale Mala Pua (Garden Home) is the perfect place for family and friends to gather or for a romantic getaway on the stunning Hamakua Coast. This spacious plantation house (2,200 square feet) is located just north of Hilo in the lush and tropical ...

  • 2 bedroom
  • 3 bathroom
  • Sleeps 6
Hawaii> Hakalau
from $403 
View Property    

Hale Mahina A-302 Oceanfront Condo in Maui

Welcome to Hale Mahina A-302! With a direct oceanfront view and located on a secluded and gated white-sand beach, our condo is perfect for those looking for a quiet and relaxing West Maui getaway.

Our favorite thing about this condo is ...

  • 2 bedroom
  • 1 bathroom
  • Sleeps 3
Hawaii> Lahaina
from $412 
View Property    

Hawaii 2-Bedroom Retreat Near Maalaea Harbor

In Hawaii's lush tropics, discover your dream home at this stunning 2-bedroom retreat. Nestled just an 11-minute walk from the picturesque Maalaea Harbor, you'll be perfectly positioned to explore the stunning West Maui Mountains and the ...

  • 2 bedroom
  • 2 bathroom
  • Sleeps 4
Hawaii> Wailuku
from $532 
View Property    

Poipu Beach House Historic Kauai Vacation Home

Welcome to the Poipu Beach House. IG @poipubeachhouse. A beautiful 1920s-era plantation home steps from Poipu Beach. This home is a historical gem that takes you back to old Hawaii with original wood floors, lava rock footings, and 100+ year ...

  • 3 bedroom
  • 3 bathroom
  • Sleeps 8
Hawaii> Koloa
from $1,281 
View Property    

Beautiful 1BR Ground Floor Condo Near Beach & Golf

This is a an amazing 1 bedroom 1 Bath ground floor unit with plenty of space.It has been fully renovated with beautiful furnishings inside and out. It has lots of windows that lead out to a spacious patio. It has central air if the cool Hawaiian...

  • 1 bedroom
  • 1 bathroom
  • Sleeps 5
Hawaii> waikoloa village
from $315 
View Property    

Elegant Kauai Haven with Stunning Ocean Views

Kauai Haven is nestled within a classic Hawaiian style backdrop, resting on the edge of a bluff overlooking the spectacular Pacific Ocean. An award-winning designer, who is part of the Coastal Living Network of designers, has designed this ...

  • 2 bedroom
  • 2 bathroom
  • Sleeps 4
Hawaii> Princeville
from $566 
View Property    

Spacious Waikoloa Villa Near Beaches and Golf

Your Island Paradise Awaits You! Feel right at home in our spacious 1700 square foot, 3 bedroom, 2 1/2 bath Villa with an attached garage. This beautifully decorated Villa is just steps away from the resort style pool featuring a lava rock ...

  • 3 bedroom
  • 3 bathroom
  • Sleeps 6
Hawaii> Waikoloa Village
from $567 
View Property    

Oceanfront Hawaii Home with Stunning Views and Whale Watching

Simply put, this property sits on one of the most gorgeous ocean-front locations in East Hawaii. Unlike other ocean-front homes, you will not need to walk to the end of a yard to appreciate the Pacific waves. Here, you will feel as if you are on...

  • 2 bedroom
  • 3 bathroom
  • Sleeps 5
Hawaii> Hilo
from $657 
View Property    

Luxury Ocean View 2BR Condo at Alii Kai

Travelers looking for the FINEST and most LUXURIOUS accommodations, look no further... This top floor, 2 bedroom and 2 bath condo is nestled on the Ocean Bluff with both Tropical Garden and Ocean Views. This Condo is a SECRET GEM offering High ...

  • 2 bedroom
  • 2 bathroom
  • Sleeps 4
Hawaii> Princeville
from $396 
View Property    

Paia Ko Maui Retreat with Ocean Views

Permit STPH 2015/0002 GET: 146669772802 TAT: 14666977280

Welcome to Paia Ko: Your Tranquil Maui Retreat

Paia Ko is a serene and charming 3-bedroom, 2.5-bath home featuring beautiful ocean views and central air conditioning. ...

  • 3 bedroom
  • 3 bathroom
  • Sleeps 6
Hawaii> Paia
from $977 
View Property    

Puako Pau Hana: Charming Beachside Vacation Home

Puako Pau Hana is a great place to escape from all your cares! Located in the heart of Puako, you are literally just a few steps to the most beautiful little beach in Puako!
Puako is known for it's magical old fashioned neighborhood feel and...

  • 2 bedroom
  • 2 bathroom
  • Sleeps 4
Hawaii> Waimea
from $412 
View Property    

Elegant Maui Sunset Condo with Ocean Views

Paradise inside and out! The elegant B314 is an elevator ride up to the third floor of the Maui Sunset, where you'll enjoy breathtaking ocean views right outside your window. The warm Hawaiian shore nestles directly against the Maui Sunset ...

  • 1 bedroom
  • 2 bathroom
  • Sleeps 4
Hawaii> Kihei
from $349 
View Property    

Elegant 1BR Ocean View at Maui Kaanapali Villas

Welcome to Maui Ka’anapali Villas!
Our beautiful One Bedroom, 2 Bathroom Corner Unit is extremely rare! Located on the 5th floor of the Aloha Tower featuring breathtaking panoramic ocean views from the Living Room, Open Kitchen and the ...

  • 1 bedroom
  • 2 bathroom
  • Sleeps 4
Hawaii> Lahaina
from $607 
View Property    

Charming Kihei Garden Oasis with Hot Tub & Modern Amenities

Beautifully remodeled house with ultra-quiet split AC systems in every room, fun for everyone with the new Infinity game table, whole house water filtration system, ceiling fans, resort-style landscaping and lighting.

Within a 10 to ...

  • 4 bedroom
  • 2 bathroom
  • Sleeps 8
Hawaii> Kihei
from $806 
View Property    

Kauai Oceanfront Couples Studio Condo with Beach Access

Aloha and welcome to our tropical paradise in beautiful Kauai, Hawaii!

Indulge in an extraordinary couples' getaway at our top floor ocean and beachfront studio condo in Kapa'a. Just 150 steps from our condo's front door, the beach ...

  • 1 bedroom
  • 1 bathroom
  • Sleeps 2
Hawaii> Kapaa
from $381 
View Property    

Ma'alaea Beachfront Condo with Ocean & Mountain Views

If you come to Maui for the warm breezes that seem to kiss your skin, then this unit -#203 - is just waiting for you. The trade winds that love our area keep you cool and comfy. Not that you need it that much but there is AIR CONDITIONING - ...

  • 2 bedroom
  • 2 bathroom
  • Sleeps 5
Hawaii> Kihei
from $388 
View Property    

Oceanfront Condo at Halii Kai Waikoloa Beach


Halii kai is an Ocean front Resort in the beautiful Waikoloa Beach Resort. What sets 16B apart from the rest? Location, amenities and service. I live on Island and can assist with any issues or questions. Halii Kai Unit 16B is right ...

  • 2 bedroom
  • 2 bathroom
  • Sleeps 5
Hawaii> Waikoloa
from $454 
View Property    

Hale Leilani: Tropical Kauai Retreat Near Beaches


Welcome to Hale Leilani (Heavenly Home). Our home is a stunning 3 bedroom Hawaiian style home with soaring ceilings and a lush tropical garden with trees all around for privacy, making it great for couples or families visiting the ...

  • 3 bedroom
  • 3 bathroom
  • Sleeps 6
Hawaii> Princeville
from $790 
View Property    

Serene Princeville Golf Course Vacation Home with Amenities

Peaceful...Serene...Relaxing...

HIGHLIGHTS:
• Over 3100 square feet of space
• Quiet residential neighborhood on the Makai Golf Course at Princeville
• Beach and snorkel gear
• Close to grocery ...

  • 4 bedroom
  • 4 bathroom
  • Sleeps 10
Hawaii> Princeville
from $802 
View Property    

Top-Floor Ocean View Studio Condo in Kauai

Aloha and welcome to our tropical paradise in beautiful Kauai, Hawaii!

Indulge in an extraordinary couples' getaway at our top-floor ocean view studio condo in Kapa'a. Just 160 steps from our condo's front door, the beach awaits! ...

  • 1 bedroom
  • 1 bathroom
  • Sleeps 2
Hawaii> Kapaa
from $359 
View Property    

Renovated Kaanapali Beach Condo with Ocean Views

Unit 162.
Update: Fall of 2022 we installed a Grohe hand-held shower head so that parents could more easily wash their children. In the summer of 2021 we added new artwork. In 2019 we installed a new 55” Samsung LED LCD Smart TV! It’s ...

  • 1 bedroom
  • 1 bathroom
  • Sleeps 4
Hawaii> Lahaina
from $359 
View Property    

Charming 3BR Duplex Near Magic Sands Beach

Welcome to this wonderful 3 bedroom / 2 bathroom duplex home only a 3 min walk from Magic Sands Beach. Just remodeled and professionally decorated, this charming vacation getaway has all of the comforts you desire in your home away from home, ...

  • 4 bedroom
  • 2 bathroom
  • Sleeps 7
Hawaii> Kailua-Kona
from $502 
View Property    

Poipu Sands Garden View Condo Near Beach and Golf

We purchased this lovely ground floor garden view condo in April, 2013. This condominium has a large master bedroom with A/C. The master bedroom has an an en-suite master bath with a walk in shower. Our home also has a half bath for your ...

  • 1 bedroom
  • 2 bathroom
  • Sleeps 2
Hawaii> Koloa
from $369 
View Property