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.
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...
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...
@ 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...
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....
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...
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...
Ko Olina Beach Villas O822: Elegant Retreat, Lagoon Views, Spacious Lanai
Welcome to Ko Olina Beach Villas O822 by Gather where luxury meets the serene beauty of Hawaii. Situated in the Ocean Tower at Ko Olina Resort, this villa is a stone's throw away from a well-groomed lagoon, offering guests an intimate connection with nature's wonders,...
nNew 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'....
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...
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...
❤️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...
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...
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...
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...
Spacious 3BD/2BA Beachfront Condo - Perfect Family Retreat– Menehune Shores #510
Menehune Shores #510 – Spacious Three-Bedroom Oceanfront LuxuryWelcome to Menehune Shores #510, a beautifully remodeled three-bedroom, two-bathroom condo designed with luxury and comfort in mind. Featuring high-end finishes, modern conveniences, and sweeping ocean...
Stunning Oceanfront Retreat with Spectacular Views and New Upgrades!
SPECTACULAR!! HIGHLY desirable third-floor condo!! Enjoy beautiful, unobstructed, panoramic ocean views from your own spacious and private lanai. Listen to the gentle sounds of the ocean at this DREAM get-away.Unbeatable location right on the water. View the tropical...
OWL NEST: serene stream side retreat for 2 or 3
The Owl Nest: Family friendly. Be immersed in nature at our peaceful, cozy stream side retreat. Located next to the Waipio Lookout, our Hamakua Coast rain forest property is the perfect place for two adults with one child stays. Hear the rush of our waterfall and...
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,...
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...
Newly Renovated Ocean View Retreat! Polo Beach 309
First time offered for rent, Polo Beach Club #309 has been a lovingly cared for home up until now. Be the first to stay in this beautifully updated home with ocean views and palms to shade for privacy. #309 is a spacious and bright condo with soft whites and tans...
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...
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...
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...
❤️PiH❤️ Home of the Milky Way ★ Ocean Views ★ Pool and Spa ★ Astronomy Retreat ★
Brought to you by Paradise in Hawaii Luxury HomesWelcome to Home of the Milky Way, Hale Lalani Hoku, a part of our Hawaiian Luxury Collection. Home of the Milky Way is a wonderful 3 bedroom home on Kohala Ranch. It has some of the most amazing views of the Pacific Ocean...
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...
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,...
NEW! Ocean View Hawaii Vacation And Event Retreat
Welcome to our breathtaking vacation rental on the Big Island of Hawaii! Nestled amidst stunning natural beauty, this magnificent property boasts not one, but two panoramic homes, providing the perfect getaway for larger groups, family vacations, retreats, and special...
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...
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...
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...
Maui Kaanapali Villas 292 60%Off April & May Deals at Remodel OceanFront Retreat
The Stice Team — Powered by Gather Vacations. Maui Born and Raised Professionals. Your Local Experts in Crafting Unforgettable Stays.Welcome to Maui Kaanapali Villas 292, a beautifully remodeled top-floor condo where up to six guests can enjoy the perfect balance of...
Private Princeville Retreat w/ Hanalei Bay View!n
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...
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...
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...
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...
Ground-Floor 2BR Retreat with Ocean Views & Easy Beach Access – Wailea Elua #307
Wailea Elua #307 – Ground Floor Ocean View Comfort with Tropical EleganceWelcome to Wailea Elua #307, a newly remodeled ground-floor condo located in the oceanfront section of one of Wailea’s most exclusive communities. With expansive ocean and garden views, upscale...
The Sandy Feet Retreat - Oceanfront top-floor corner unit on Kauai Coconut Coast
This gorgeous oceanfront, two bedroom, two bath condo at Lae Nani in Kapaa is the perfect place to relax and enjoy yourself with friends and family. Private, top floor corner unit (no one above you), featuring high ceilings, a fully equipped kitchen remodeled with...
Coastal Condo Retreat - Exquisite Views. Short Walk to Beaches. Tennis Courts!
This perfectly positioned condominium with private lanai will inspire your sense of adventure as well as be your space for relaxation! Support Maui's economic recovery by building your book of vacation memories in central Kihei close to everything you want to do! The...
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...
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...
Beachfront Oasis: Kihei Beach #303, Your Retreat with Breathtaking Ocean Views!
Kihei Beach #303 – Remodeled One-Bedroom Beachfront CondoWelcome to Kihei Beach #303, a beautifully remodeled one-bedroom, one-bathroom beachfront condo offering comfort, charm, and sweeping ocean views. Located in a six-story beachfront property in North Kihei, this...
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,...
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...
Tropical Oceanfront Retreat
About Wailua Bay View #309Our unit offers a drop-dead beautiful ocean front view.Wailua is on the island's sunny East side, allowing you to explore both North and South shores easily.Great swimming, hiking and kayaking are moments away.You can explore restaurants and...
Ocean View Retreat on the Garden Island!
Experience the best of Kauai’s North Shore at this newly updated condo in Princeville, one of the island’s most sought-after communities. Enjoy breathtaking Pacific Ocean views right from your living room or private lanai, with a lush grassy lawn just beyond. Spend...
Exceptional Ground Level Retreat: Kihei Surfside #102 – Stunning Pacific Views!
Kihei Surfside #102 – Stylish Ground-Floor Ocean View Condo with Recent UpgradesDiscover the best of coastal living at Kihei Surfside #102, a beautifully updated ground-floor condo offering ocean views and easy beach access. This 1-bedroom, 1.5-bathroom unit sleeps up...
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...
Hale Halai beautify large home perfect for families & small company retreats
This 5000 square foot spacious home with an open floor plan is excellent for families, friends, and co-workers to gather and enjoy each others company. It has 7 bedrooms, 5 bathrooms, A/C, and a private pool. Tropically landscaped grounds with a BBQ and a spacious yard....
Spacious Island Retreat With Ocean Views In Poipu!
Experience the very best of Kaua‘i’s South Shore at Sunset Kahili—Poipu’s premier oceanview escape.This spacious 1-bedroom condo offers endless views of the Pacific and unforgettable sunsets, making it the perfect retreat for couples or solo travelers. Located...
Tropical Forest Retreat Near Ocean - Ho'ohauoli
This private Pāhoa getaway offers the perfect location for your next Big Island adventure! Surrounded by lush, tropical foliage, this home features a large covered lanai, a fenced yard, a newly renovated kitchen, and even an avocado tree that you can enjoy in season....