Hawaii Retreat Vacation Rentals
Hawaii retreat rentals offer tranquil hideaways for wellness travel, spiritual renewal, and quiet vacations away from the crowds. From off-grid cabins to elegant estates with private lanais and ocean breezes, these properties invite you to slow down and reconnect with nature.
Whether you're planning a yoga retreat, creative sabbatical, or couples' sanctuary, Hawaii's diverse landscapes provide the perfect backdrop. Choose from rainforest cottages in Volcano, coastal escapes near Hanalei, or spa-inspired villas along the Kohala Coast.
Most retreat-style rentals include spacious outdoor areas, privacy fencing, soaking tubs, gourmet kitchens, and calming interiors that emphasize natural light and open-air living. Some properties may also offer wellness-friendly features such as outdoor yoga decks, meditation spaces, or proximity to holistic centers.
Key Features of Hawaii Retreat Rentals
- Private and secluded locations for maximum tranquility
- Surrounded by nature: ocean cliffs, forests, or gardens
- Open-air lanais, soaking tubs, and serene design
- Ideal for yoga, meditation, creative work, or romantic escapes
- Proximity to sacred sites, hiking trails, and beaches
- Multi-day or long-term stay options available
Ready to relax and recharge? Explore options in Upcountry Maui, Anini Beach, or Waimea for a peaceful island experience rooted in Aloha.
Majestic Mountain Studio Retreat
Imagine vacationing in a brand new studio set in a peaceful valley. You're surrounded by Ka’ala & Waianae mountains, towering palms, mango trees, wild peacocks, & famous beaches.You take a sunrise/sunset stroll around the gated neighborhood (w/24hr security) and return...
@ Marbella Lane -Coastal retreat near Diamond Head
Summary:Enjoy this tastefully decorated studio with lots of natural light and cool ocean breezes. This unit has a private lanai, great for enjoying your morning coffee or afternoon tea, and has a great view of Diamond Head, Kapiolani Park and across-the-street water...
Beachy Boho Retreat in the Heart of Kihei – Steps to Beach!
Ready to get away from it all? Say aloha to this beautiful beach side retreat in easygoing Kihei, ready for you and your guests to enjoy the fun, sun and experience why ‘Maui no ka ?oi’! Just across the street from the beach, this 2 bedroom, 2 bath condo sleeps up to 6...
Private Princeville Retreat w/ Hanalei Bay View!
Discover the very best of Princeville from the comfort & convenience of this peaceful private retreat! Step outside onto your balcony for spectacular views of the majestic Hanalei Bay, enjoy a round of golf at the Makai Golf Club, or stroll down to relax on Hideaway...
Island Life Retreat-Ocean Front-Beach Access
BEACHFRONT • GROUND FLOOR • WALK-OUT Step straight from your lanai onto a quiet stretch of white sand—your own authentic Hawaiian paradise. The reef-protected turquoise waters are calm and perfect for swimming, paddleboarding, kayaking, or simply floating in the warm...
Sun-Soaked Waikoloa Retreat w/ Private Lanai!
Sandy beaches, amazing waves, and ocean views all await you when you book this amazing condo in Waikoloa! Head to the community's oceanfront club, complete with a private pool, restaurant, and bar, then go to one of the nearby beaches. Venture out and swim with dolphins...
Temple Tree Retreat - An Adventurer's Oceanfront Paradise!
Overlooking ancient lava ocean cliffs, Temple Tree Retreat is designed to see and feel nature all around you. Our home has three main living spaces - you get the entire property to yourselves. The main area hosts the kitchen, two bedrooms, bathroom and laundry room....
Oceanfront Kealakekua Bay Retreat w/ Breathtaking Views from Every Room
Manini Beach Breath TakerOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Located in Kealakekua Bay, a protected marine sanctuary and an ideal spot for snorkeling, diving, and...
Ocean-view Waikoloa Village retreat with air conditioning - discounted golf
683712KA Waikoloa Village DreamsOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'This open and airy two-bed/two-bath home sits 1,000 feet above sea level, offering cool breezes and...
Waiohai Beach House – Elegant Oceanview Retreat in Poipu
This oceanfront home embodies the essence of ‘Island Casual’ living, with a focus on relaxation and the breathtaking beauty of its direct ocean views; a perfect spot for those seeking an authentic and unpretentious island experience. The spacious, beautifully furnished...
Ground-Floor Beachside 1BR Retreat with Private Patio, Lawn, Pool & Health Club
Escape to our newly remodeled 1-bedroom, 1-bath condo, perfect for couples or small families seeking a beachside getaway. Located on the ground floor with no stairs, this condo offers a private patio opening onto an expansive grass lawn, ideal for kids to play or for...
❤️PiH❤️ Champion View Retreat ★ Private Infinity Pool PLUS Free Hilton Resort Passes ★
Brought to you by Paradise in Hawaii Luxury HomesWelcome to Champion View Retreat, part of our Hawaiian Luxury Collection. Champion View Retreat has private pool and spa with stunning golf, ocean and sunset views.Located in the prestigious Champion Ridge, this is one of...
Poipu Kai 1BR Retreat w/ Ocean View & Pools, Walk to the Beach
E Komo Mai — Welcome to Kahala 621 at Poipu Kai ResortExperience island living at its finest in this spacious 1-bedroom, 1-bath condo at the premier Poipu Kai Resort on Kaua'i's sunny South Shore. Relax on your private lanai with ocean views and enjoy lush tropical...
Serene Aliomanu Bay Vacation Rental on Kauai's East Shore
This exquisite, fully remodeled four-bedroom home is regally perched as close to the edge of the ocean as a house in Hawaii can be. Featuring a private staircase with 11 steps leading directly to the water’s edge, this is beachfront living at its finest. With sweeping...
Stylish, oceanfront retreat with scenic balcony, pool & fast WiFi
Mahina Surf 201Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Boasting some of the best views in the area, this stunning oceanfront getaway is ready to welcome you with plenty of...
Beachside Retreat with High-Speed Wi-Fi and Pool
Summary:🏖️ Walk to the beach, shops & top restaurants 🌅 Stunning garden lanai – perfect for coffee & wine 🛏️ Ultra-comfy queen beds for a restful sleep 💦 Resort-style pool, hot tub & BBQ area 📺 Smart TV & high-speed WiFi for entertainment 🚗 Free parking for hassle-free...
Marvel at picturesque views from this premier Hawaiian retreat!
Marvel at the picturesque views from this premier Hawaiian retreat of Grand Champions 35. Located in the heart of Wailea with a country club feel and centered on 11 acres, amid the 18-hole Wailea Blue Golf Course. You'll also find the world-class Wailea Tennis Center...
Ho'o Maluhia: Breezy Oceanview Retreat w/Private Pool and Stunning Views
Hoʻo Maluhia – Ocean View Luxury Retreat with Pool, A/C & Sunset Lanais Above Kailua-KonaExperience Big Island paradise at Hoʻo Maluhia, a luxurious hillside retreat perched 700 feet above Kailua-Kona. This spacious two-level home offers breathtaking 180° ocean views, a...
"Your Sweet Maui Retreat" Remodeled 1 Bedroom steps from Kihei's best beaches.
This perfectly located condo is in the heart of Kihei, just 5 walking minutes to the best beach in Kihei. Many of the favorite shops and restaurants are located within 5 minutes of our new remodeled condo. From the spacious living room to the large lanai, our bright...
Kiahuna 323 - Ohana Garden Retreat - Garden Deluxe View overlooking Moir Cactus Garden
Summary:Beautiful first-floor garden retreat overlooking the Moir Cactus Garden. Upgraded with granite countertops, modern kitchen appliances, a luxurious bath, and a spacious lanai with lush garden views. Easy access with just five steps or lanai entry. Includes beach...
Pali Ke Kua 216 Amazing Panoramic View, idyllic retreat
Perched on the spectacular Princeville ocean bluff, Pali Ke Kua 216 offers one of the best 180-degree panoramic view of the breathtaking Bali Hai and the picturesque Hanalei Bay and pristine beaches below. This fantastic condo is an idyllic retreat from modern day...
A Premier Tropical Retreat at Kamaole Sands
Our condo is a distinctive one-bedroom, two-bath end unit vacation condominium rental (5-301) at beautiful Kamaole Sands, across from popular Kamaole III Beach Park in South Maui.........Smoke free condo and lanai. Top 'Superior' rating from our property management...
New open concept Garden Delux Kiahuna, Partial Ocean View Retreat!
Celebrate Aloha and the tradition of Hawaii with a stay at our slice of paradise. You'll take a step back in time to a simple more relaxing period when you arrive at Kiahuna Plantation on the sunny south shore of the beautiful island of Kauai, 'The Garden Island'....
Loke Lani: Poipu Kai Luxury Home with Private Pool
🌴 E Komo Mai — Loke Lani | Private Poipu Retreat with Lagoon PoolExperience tropical island living at Loke Lani, a bright and airy 3-bedroom, 2-bath main house in Poipu Kai. Stylishly decorated for comfort and relaxation, this home features a gourmet kitchen and a...
Gorgeous! The Waterfall Retreat At Reed's Island
ALOHA!The breathtaking Waterfall Retreat at Reed’s Island is a spectacular 4 bedroom, 3 bath home in the exclusive area of Reed’s Island in Hilo. The home is only a few minutes from downtown Hilo but it feels like a private paradise retreat with a stunning river and...
Loke Lani+Guest House by Destination Kauai - Luxury Home, Private Pool, A/C, Poipu Kai
🌺 E Komo Mai! Loke Lani + Guest House 'Ohana | Tropical Poipu RetreatDiscover your perfect island getaway at Loke Lani + Guest House 'Ohana, a bright, tropical retreat designed for comfort and privacy.The main house offers 3 bedrooms and 2 bathrooms, including a primary...
Relax...Recharge...Retreat!
The perfect place to relax and recharge with the expanse of the ocean and sound of the waves right in front of you....plus every once in a while a rainbow will mesmerize you with its beauty....right from your lanai. A central air system in every room to cool you off!...
Modern Ground Floor Retreat - Kihei Surfside #110 - Perfect Oceanfront Grounds!
Kihei Surfside #110 – Ground-Floor Oceanfront Condo with Stunning ViewsLocated just steps from Keawakapu Beach, Kihei Surfside #110 offers the perfect blend of comfort, convenience, and breathtaking oceanfront views. This ground-floor one-bedroom,...
Poipu Oceanfront Penthouse AC, high WIFI, Well Stocked Kitchen, Beach Chairs
Welcome to your private sanctuary on the top floor of a premier oceanfront location in Poipu, Kauai. Just forty feet from the shoreline, this two‑bedroom, two‑bath condo offers 180° unobstructed views of three renowned surf breaks—“PKs,” “Centers,” and “Acid Drops.”...
Oceanfront - Dolphin Retreat - KAYAKS INCLUDED
On the shores of Kealakekua Bay, a Protected Marine Conservation area, is an enchanting, 4 bedroom/3 bath, water front house called the Dolphin Retreat. This open and airy private home has all the amenities one would desire for a tropical vacation. The property is...
OCEANFRONT Condo. Steps from the water! KULEANA 622
Perfectly located between Kaanapali and Kapalua, this beautiful 1-bedroom, 1-bath oceanfront condo at the highly sought-after Kuleana Resort offers guests the ultimate Maui getaway. Situated on the 3rd floor, this unit delivers breathtaking panoramic ocean views,...
Oceanfront 2BR Retreat with Stunning Views and Luxury Amenities Makena Surf B305
Welcome to Makena Surf B305! This unit is all about LOCATION and VIEWS! Makena is located a short five minute drive from all of the restaurants and shops in Wailea but offers the seclusion and privacy from all of the resort traffic! Makena Surf is one of the best kept...
Waterfront retreat w/ a furnished balcony, incredible view, & a shared pool
Kona Bali Kai #205Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Paradise awaits at this two-bedroom, oceanfront, Kailua-Kona condo. Offering a variety of desirable amenities,...
Private Top Floor Retreat w/ Incredible Ocean Views from Every Room
Sealodge G8 is beautiful and welcoming home-away-from-home that has some of the best views on the entire island! Situated in the heart of Princeville, your cozy escape has two bedrooms that look right out over the water, a comfortable and well-appointed living and...
Ideal resort retreat with central AC and access to pools, hot tub, golf, & more
Shores at Waikoloa 338Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'As you step off the elevator you will feel the enchanting ocean breezes and an endless array of resort amenities...
Stunning Private North Shore Oceanfront Retreat!
Prime oceanfront location in the illustrious Pali Ke Kua condominiums. This modern condo features cascading views of Hanalei Bay and beyond! Situated in the Princeville community, this retreat is located near all the north shore has to offer. Enjoy the pool, take a...
Sprawling Pacific Views Ultimate Coastal Retreat!
**Nohonani 300 – Your Renovated Oceanfront Haven**Welcome to Nohonani 300, a beautifully renovated 2-bedroom, 2-bath end unit on the third floor. Recent improvements include new carpeting and elegant furnishings, providing a fresh and inviting atmosphere. This unit...
Luxurious Seaside Retreat ~ Heated Pool & Jacuzzi
Wow... this condo is truly AMAZING. This Top-Floor End Unit is Quiet & Private. Geared specifically towards Travelers who enjoy the FINEST ACCOMMODATIONS while Vacationing in PARADISE. Picture Perfect & once inside, it's the Lap of LUXURY. Enjoy the Trade Winds from...
Paradise retreat! Plunge Pool, Hot Tub, AC & Water Gears!
Tropical Paradise in Princeville’s most desirable neighborhood tucked between golf course and the ocean, across the Queens Bath. Two-level house with 3 bedrooms, den and nook can accommodate 11 people. Bali style furniture and all memory form mattresses. equipped...
Peaceful retreat with pool, gym & BBQ
Summary:Family Friendly, Near Pool, Updated BathroomsThe Space:Welcome to your serene Waikoloa escape - ideal for families, couples & relaxation seekers! Enjoy peaceful mornings, nearby beaches, & shared resort-style comforts:- Sleeps 4 | 2 bedrooms | 2 beds | 2 baths-...
Spacious retreat with pool & private lanai
Summary:Private, Access to Mauna Lani Beach Club, Spacious, Great Backyard!The Space:Welcome to your peaceful Hawaiian retreat in the Islands at Mauna Lani, where tropical gardens, nearby beaches & resort amenities invite pure relaxation:- Sleeps 5 | 2 bedrooms | 4 beds...
Oceanfront Bliss – A Relaxing Retreat with Breathtaking Views
Whether you’re here to soak up the incredible sunsets, spot sea turtles from the lanai, or witness majestic whales (in season),this serene escape is ready to make your island dreams come true. Step inside this fully updated condo and experience modern comfort paired...
Kona Pacific C416 by Gather: 1BR Condo Retreat w/ Pool & Ocean Views
Welcome to Kona Pacific C416, a beautifully appointed 1-bedroom, 2-bath ocean-view condominium in the heart of Kailua-Kona, Hawai‘i. This 830-square-foot retreat offers modern comfort and tropical tranquility, accommodating up to four guests—ideal for couples, families,...
New! Palms 702 - Romantic Retreat - Split AC in Bedroom - Open-Air Living Area
Discover the perfect Maui escape at Palms at Wailea 702, a beautifully updated 1-bedroom, 2-bath luxury vacation rental ideally located in the heart of Wailea. This spacious ground-floor condo is designed for couples seeking a romantic retreat, offering comfort, style,...
Tropical Serenity - Lovely Maui Retreat 1Bed Suite
Discover Maui at Maui Banyan Q110 apartment, a lovely 1-bed 1-bath apartment steps from Kamaole Beach Park II, perfect for up to 4 guests. Conveniently located right next to the upper pool area which also includes six Weber BBQs. Relax on the lanai amidst lush greenery,...
Cozy ground floor retreat on Kaanapali Beach
Welcome to your tropical getaway at Kaanapali Shores 144, a 1-bedroom, 1-bathroom condominium that offers convenient ground-floor access, Unit 144 can accommodate up to 4 guests. When it's time to retire for the night, you'll find a king-size bed adorned with...
Holomakani Retreat: Your Ohana's Hale (Home) by Kaanapali Beach
This is a legally permitted vacation rental according to the County of Maui ordinances.Ocean Views, Private Pool & Spa, Steps to Kaanapali Beach – Your Maui Paradise Awaits E komo mai (welcome) to your island sanctuary, where the beauty of Maui and the spirit of aloha...
Romantic Tropical Retreat, 150 yds from the Ocean!
Kona Dreams sleeps 4 adults. Walk 150 yards to the ocean. 2 bed/2 bath tropical home in a quiet neighborhood. Chef’s kitchen, laundry, beach gear, use of kayak. Free phone, wireless, off-street parking. Hiking and beach on-site. Maid service with an extra fee.Kona...
Molokai Island Retreat w/ Ocean View & Pool!
Venture to the picturesque island of Molokai for a solo trip or romantic getaway. Discover the tallest sea cliffs in the world, lush hikes to Kalaupapa and Halawa Valley Falls, sport fishing, and colorful reefs perfect for snorkeling when you stay at 'Blue Marlin', a...
Panoramic ocean views and neighboring islands
Step inside Mahana 517, a 1-bedroom, 1-bath, 5th-floor condo that offers direct ocean views, an in-unit washer and dryer, and a central air conditioning system. This property has elevators. Unit 517 can accommodate up to 4 guests. The master bedroom features a king-size...