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.
Quaint Studio in Heart of Waikiki
With its outstanding location in the heart of Waikiki, this studio apartment offers a comfortable and convenient stay. Be steps away from the ocean, yet central to restaurants, shops, and amenities. The high floor offers partial ocean views, along with mountain view....
Charming Waikiki studio close to beach and centrally located to restaurants, shops and attractions.
Want to be close to the beach and centrally located to restaurants, shops and attractions? Then this is studio for you! The beach is less than 10-minute walk. Shops and restaurants are at your doorstep. After a busy day, relax in this charming studio with queen sized...
Comfortable loft condo with private lanai, resort pool, hot tub, tennis courts!
Maui Kamaole K205Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Experience the beauty of Maui from this immaculate 2-bedroom, 2-bathroom condo at Maui Kamaole in Kihei, Hawaii....
WE 907 Breathtaking Ocean Views from the Top of Wailea 2BD Amazing Location
Wailea Ekolu 907 NEW LISTING! FREE daily activities included with your stay value up to $956! Complimentary admission, every day of your stay*: Lu'au, Golf, Whale Watching (seasonal), Sunset Dinner Cruise, Molokini Snorkel Trip, Alpaca Farm Tour, Pineapple Farm Tour,...
Hale I'a U'i: Heavenly Hawaiian Hideaway...Oceanfront
WELCOME TO HALE I'A U'i: YOUR HAWAIIAN PASSPORT TO PARADISEExperience the ultimate seaside escape where luxury meets the natural beauty of the Big Island.Located in Puako, a charming community with an "Old Hawaii" feel, you will find yourself transported back in time...
❤️PiH❤️ Mauna Kea Horizon ★ Newly Updated ★ Ocean Views ★ Sleeps 8 ★
Brought to you by Paradise in Hawaii Luxury Homes.Welcome to Mauna Kea Horizon, part of our exclusive Hawaiian Luxury Collection.Perched within the Kumulani complex at Mauna Kea Resort, Mauna Kea Horizon offers sweeping views of the golf course, mountains, and the...
Pacific Shores 2-Bdrm across from Charley Young Beach!
This enjoyable condo in Kihei offers a relaxing escape for guests. The kitchen was recently remodeled and the unit has tile throughout, washer/dryer in unit, air conditioning in the living room and ceiling fans in each room. With 2 bedrooms featuring a king and queen...
Oceanfront Bliss Pool & Stunning Views Hono Kai C3
Relax and rejuvenate with stunning Ocean and Haleakala views from your living room and lanai. Perfect for whale watching, this beachfront escape features a fully stocked kitchen and all the comforts you need. Lounge by the oceanfront pool, savor BBQs, bask in the Maui...
Maui Resort Rentals: Polo Beach Club 608 – Luxurious 6th-Floor Oceanfront 2BR w/ Stunning Ocean Views!
Boasting a stunning Wailea oceanfront location and a lavish interior, this 2BR/2BA residence delivers stunning Pacific Ocean views from nearly every room.During the winter months, watch the whales breach right from your living room. During the summer months, enjoy...
Coastal Chic Condo with Ocean View & Full Kitchen
Step into a bright and airy beautiful condo, where modern elegance meets coastal charm. Expansive windows invite natural light to flood the open living space, offering breathtaking views of the marina and the sparkling Pacific Ocean. From your private balcony, enjoy the...
Part Ocean View, Beach Theme 23rd Fl, Free Parking with WiFi, AC
*We prioritize cleanliness! We inspect and re-clean the unit, and personally launder linens without harsh chemicals.*Welcome to our 1BR condo in the heart of Waikiki, just steps away from famous Waikiki Beach!Features fully equipped kitchen, pull-out sofa bed, private...
Kona Oasis: Ocean Views, Chill Pool, AC, Beautiful 4 bedroom home in Kona
Welcome to your tranquil getaway, Kona Oasis Hale! This home is Big Island Paradise Living: your dream getaway nestled on the stunning coastline of Hawaii. A truly spacious 4 bedroom home that offers not only breathtaking ocean views but also a perfect blend of luxury...
Studio Premium Villa - Ocean View at Westin Ka'anapali Ocean Resort Villas
Settle into the lap of luxury, where plush bedding assures pampered restfulness for the weary traveler.If the majesty of Maui’s beaches and mountains weren’t enough to sell you on a trip to Hawaii, perhaps the allure of this world-class wellness resort will tip the...
*Newly Renovated Oceanfront Waikiki- Ilikai Marina
*Exciting Updates in Progress!We’re currently renovating to make your stay even better. In the meantime, please take a look at our beautifully updated Ilikai Marina listing to see the stunning upgrades you can expect soon!We’re excited to share our top picks for local...
Walk to the beach! North Shore Surf House
Step into your newly remodeled condo (one of the largest on property). Walk to the beach, restaurants and more. Indulge in luxury with 2 private pools, tennis and pickleball courts, and 5+ miles of pristine beaches just moments away. Dive into adventure with surfing,...
Welcome to Mavi Bay, luxury ocean view condo,by Kamaole II beach newly renovated
Welcome to Mavi Bay, our beautiful condo, completely renovated and professionally decorated in summer/fall 2024. You are sure to have a marvelous stay at this 1 bedroom condo in Kihei across one of the best beaches with sweeping ocean views from the sixth floor.From the...
SPECTACULAR OCEANFRONT A/C Near everything! at the Kahana Beach. Studio, Lanai
Welcome to our relaxing Kahana Beach Condo, 20 ft from ocean, fantastic location, cozy comfort meets paradise! Our air-conditioned haven provides a refreshing retreat from the tropical heat, ensuring you stay cool and relaxed throughout your stay.Step into our spacious...
New! Kailani #213, Oceanfront, Sunrise and Moon Rise Views!
Welcome to Kauai Kailani #213, Kapaa, Kauai Vacation Rental.Escape to paradise in this charming oceanfront condo located on Kauai’s stunning Royal Coconut Coast. Perfectly positioned within walking distance to delightful shops, restaurants, and coffee houses, this cozy...
***SPRING SPECIAL*** Kulalani Complex: Experience Hawaiian Luxury, Stunning 2-Bedroom Townhouse
Escape to this luxury two-bedroom townhome in Kulalani at Mauna Lani Resort on the Kohala Coast of the Big Island, Hawaiʻi. This spacious and stylish retreat combines resort-style amenities with the privacy of a gated community.Highlights-Mauna Lani Beach Club Pass –...
***SPRING SPECIAL*** Charming Home, Just Minutes from Town and the Beach with Ocean View.
Kona Ocean View Vacation RentalWelcome to your Big Island retreat—a spacious two-story vacation home in a peaceful neighborhood just minutes from downtown Kona and some of the island’s best beaches.The open kitchen flows into inviting living spaces, while an outdoor...
Lei Aloha - A Private Retreat, Pool + Fairway Views
Welcome to Lei Aloha, Princeville!This luxurious island home is a 4 bedroom, 4 bathroom home combination of elegance filled with an abundance of amenities. This hidden retreat located in the prestigious resort community of Princeville is one of its kind , and provides...
Luana Waikiki Premium Studio- Gym & Pool
Enjoy staying at our beautiful studio at Luana Waikiki! From the private lanai you can enjoy the ever-changing City views of Waikiki, Fort DeRussy Park, and through the palms trees even catch a glimpse of the ocean. Room features premium upgrades including upscale wood...
5 Beds Downstairs Corner Unit with AC, 3 Pools, 6 minutes to Beaches, Beach Cart
Ideal downstairs corner location on greenbelt in preferred Regency Building 5 and adjacent to beach trail. Enjoy pleasant trade winds in this light & bright condo with portable A/C units in both bedrooms and living area (No central air or split system). This brilliant...
KKN 13231 New Listing Kihei Condo w Pool Conveniently Located Across from Beach
Kihei Kai Nani 13231 NEW LISTING Experience Kihei and Wailea from this Conveniently Located Condo Across the Street from the Beach at Kamaole 2! FREE daily activities included with your stay value up to $554! Complimentary admission, every day of your stay*: Whale...
Updated End-Unit Oasis, 3 Bd + Loft & 2 Ba, Pool, Walk to Beach, AC Coming Soon
Welcome to our private tropical oasis! This newly updated 1,478 sq. ft. end-unit offers the perfect retreat. Surrounded by lush tropical plants, you’ll enjoy privacy and tranquility, with no neighbors above or below you. The home features massive wood beams and large...
Honu Sunset Steps to the Beach!
When you vacation at Honu Sunset, you’ll embark on the trip of a lifetime! Surrounded by lush tropical greenery and within moments of some of the most beautiful beaches in the world, the opportunities to create lasting memories are endless. Housed in the 23-acre Maui...
3 Bed Oceanfront Penthouse
Welcome to your oceanfront Maui basecamp, Papakea B406! This three bedroom, two bath penthouse unit welcomes you with breathtaking ocean views, the sound of crashing waves, and is conveniently located within walking distance to beaches, markets, the ABC store,...
Best 3 bed villa by the beach
Summary:Treat yourself to vacation of a lifetime in this tastefully remodeled villa that opens to beautiful sunsets every night. Located across the lake (short walk) from golf, shopping, coffee, beach. King bed on 1st floor with no steps. Oversized main with king bed,...
Receive a $100 Gift Card for Snorkel Gear or Wailea Dining Options!
*Absolutely Stunning Panoramic Ocean and Island Views*Yards Away from Local Favorite Shops and Dining*4 beaches within 1-2 miles (Wailea, Ulua, Mokapu, Keawakapu Beaches) Experience paradise at Wailea Ekolu 104, where breathtaking panoramic ocean views and spectacular...
Bright and Airy 2BR with Loft in Princeville
Welcome to your Hawaiian retreat—a newly renovated 1,300-square-foot townhouse offering the perfect blend of comfort and island living. This split level unit, backing onto serene green space, provides an exclusive setting for your island vacation.Property Highlights*...
Ocean Front! Stunning Remodel in 2024! 102 Kona Riviera
Ocean Front Stunning Remodel in 2024Kona Riviera #102Bedroom Configuration:Master Bedroom: King Bed Living Room: Sleeper SofaAmenities:Beach Equipment: All of our vacation rentals include beach towels for the maximum occupancy, four beach chairs, two boogie boards, one...
Romantic waterfall cabin in the rain forest
Your own private log cabin and waterfall! Listen to the rushing stream as it cascades over your own private 50 foot high waterfall in your own private cabin. For the writer. For the dreamer. For the romantic getaway. Be inspired, transported and immersed into our...
Beautiful conveniently located 2-bedroom ocean view home in Kailua-Kona.
Beautiful and peaceful two bedroom home with an ocean view and convenient location. Located 7 minutes from the airport and 5 miles from town. Easy access to beaches, grocery stores, and everything Kona has to offer. This two bedroom space is the second floor of a...
April SALE-9,10,14,15 SALE 159-TreeHouse Vibe AC-WiFi-BBQ-W&D-Cliffs-Sleeps 6
(Please Note we do not rent longer than 7 days)Casa by the Sea Welcomes you.Relax in Paradise with 1 acre of Tropical Jungle to explore and the sounds of the Ocean,Birds & Frogs. 5 Min short walk to Paradise Cliffs & Parks. COME SEE THE ONLY HAWAIIAN ISLAND WITH AN...
Breathtaking Ocean View with Private Pool!
30 Days or more Rental!Discover this 2-bedroom gem in Honolulu. This tranquil house features 1 king bed and 1 queen bed, perfect for a peaceful getaway. Bidet in the bathroom, along with amenities like AC, WiFi, and a washing machine. You're sure to make fantastic...
Spectacular Hanalei Bay Resort Newly Remodeled
About this spaceHanalei Bay Resort # 1525Spectacular resort has lagoon style pools with a waterfall jacuzzi. Walk to beautiful Pua Poa beach where on a calm day you can swim and snorkel, or call for a cart if you have too much to carry. Enjoy the on site bar and...
Aloha Style! End Corner Unit w/ Ocean and Fairway Views! Kanaloa at Kona 1402
FRESHLY RENOVATED IN 2024!! Welcome to your dream Hawaiian getaway! This single-level, spacious 2 bedroom, 2 bathroom island home features sweeping ocean and golf course views. Our recently updated island home offers the perfect blend of comfort, privacy, and luxury,...
Tranquil 2-bedroom condo with AC, in Kihei. Steps from the Beach!
Stay comfortably in Kihei at this 2-bedroom condo. The space features 1 king bed and 2 twin beds, perfect for a small group of guests. With WiFi, AC, and a cozy living room with a sofa bed, this condo offers a superb stay. The bathroom includes a shower and a hairdryer...
Your Perfect Hilo Homebase - Sleeps 9 with AC
ALOHA! Welcome to your Perfect Hilo Home Base! We have two sweet, spacious Plantation Style Homes on the same lot -- this listing is for the Larger House in the Back. This 3 Bedroom 2 Bath House with outdoor deck can sleep 9 guests and is all yours. Comes with A/C, W/D...
Experience Luxury at Kaanapali Royal G303
Kaanapali Royal G303 is a 2-bedroom condo featuring amenities such as a large private lanai, a flat-screen TV, and central air conditioning. This condo can accommodate up to 6 guests with a king bed in the primary suite, a king trundle bed with an XL twin mattress in...
New Listing: Breathtaking Oceanfront Corner Unit w/ Sweeping Views Central Ac
Only four units like this at Papakea Resort— and this one’s a stunner. Spot turtles and monk seals right from the balcony of a 3rd-floor corner unit — wraparound lanai and 180° views of the Pacific included. You're 30 feet from the water and 100 yards to the beach (not...
Hale Hau`oli ~ FAIRWAYS TERRACE H104 ~ 2 BR / 2 BA ~ Pool/Spa/BBQ ~ Gym ~
Summary:Hale Hau'oli - Located on the western slope of Mauna Kea our 2 bedroom 2 bath condo in Waikoloa Village sits on the Robert Trent Jones golf course (The Village Course). Enjoy the benefits of the 900’ elevation with warm days and cool mornings and evenings. This...
Gorgeous Kapalua Home with Views
This gorgeous Maui home is a two story end unit with expansive ocean views from lanais on each level! Located in the renowned Kapalua resort area on the northern coast of Maui, you are not only close to the beach (less than a 5 minute walk, to be exact), but within...
Beachfront on Kaanapali Mahana 1106!
SPECTACULAR 11TH FLOOR OCEAN FRONT MAHANA 1106! KAANAPALI BEACH, A/CWelcome to Mahana 1106! Located on the eleventh-floor, this one bedroom, one bath condo sleeps 2-4 and features stunning panoramic views of the ocean, beach and outer islands from the living room,...
KBM Resorts | FREE CAR | Kapalua Golf Villa | Ocean view | Luxury 2-Bedroom Villa with Panoramic views! KGV-22P2
** 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...
Recent RENO! Fits 6, FREE parking
You & your family or friends will be close to everything at this centrally-located oasis in Waikiki. A couple minutes to the beach, surfing, the lagoon, boating & fishing, hiking, restaurants of every kind, shopping galore, everything Hawaii has to offer for a tropical...
Ocean View Condo with 3 shared pools, beach access, grill areas, & more!
Plantation Hale F5Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'*BOOK MAY 28-JUNE 2, 2025 FOR A DISCOUNTED NIGHTLY RATE*Located in the heart of Wailua, on the Royal Coconut Coast...
Kamaole Sands 7-405 - Stunning Renovation, Large Lanai, Ocean Views, Split AC!
Welcome to Kamaole Sands 7-405, your luxurious tropical escape in the heart of South Kihei, Maui! This stunning top-floor 2-bedroom, 2-bathroom condo is the ultimate destination for an unforgettable island getaway. With breathtaking views of the lush tropical courtyard...
Spacious Oceanfront Hideaway – Ground-Level Boho Zen Paradise with Stunning Lana
The Space:Welcome to your dream getaway at our spacious 1 Bedroom / 2 Bathroom, (sleeps 4) oceanfront ground level condo located at the prime location in the heart of West Maui!Wake up to breathtaking panoramic views of the Pacific where whales (seasonally), sea turtles...
Tranquil 2-Bedroom Getaway at The Cove Waikiki
Stay in seclusion & serenity at one of Waikiki's newest gems, The Cove Waikiki. This private community is nestled 2 short blocks from Duke Kahanamoku Bay and among Discovery Bay's ample shops, cafes and activities, and easy access to Waikiki, Magic Island Beach Park,...