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.
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...
Oceanfront Gated Estate Retreat - Banyan Tree B&B Suite w/ Horses-Beach 10m Walk
Aloha and welcome to our Hawaiian Celebration, our Ho'olaule'a. Hale Laule'a at Opihi Point is a +l$10+M, one-of-a-kind, World Class, 5-acre private, Estate Retreat sitting on the cliff edge of the Pacific Ocean with an unmatched view of the Hamakua Coast. Hale Laule'a...
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...
Tranquil tropical retreat with pool, hot tub, and golf nearby
Maui Eldorado Resort E205Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Feel your worries melt away with the ocean breeze as you relax in style at this Lahaina home. Featuring...
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...
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,...
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...
Discover Coastal Comfort: Oceanview Retreat at Kamaole Nalu #304
A Note from the Owner:Our unit is on the 3rd floor of a six story oceanfront condominium building named Kamaole Nalu which is located in South Kihei. It offers beautiful views of the Pacific Ocean and a friendly casual atmosphere. Adjacent to this unit is Kamaole Beach...
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!
A Note from the Owners: As true Maui lovers, we've created a space in Unit #303 that feels like home. The newly remodeled kitchen is fully equipped for our personal use, and we've updated the living room and bathroom for added comfort. You'll find a beautiful underwater...
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...
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...
KK 307 OceanFront 2BD Retreat with Breathtaking Views
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 Tour, Pineapple Farm Tour, and All Day Electric Bike Rental. (W1)*One ticket per...
Ke Nani Kai 132 - Spacious 2 BR/2 BA Relaxing Molokai Island Retreat
Located between Oahu and Maui...Molokai is an undiscovered treasure. 'The Friendly Isle' is a family-oriented island with deep connections to its Hawaiian traditions. Unlike the tourism driven other islands, here you can relax, slow down and have your own space. Nowhere...
Serene Eco Retreat: Ocean Views, Waterfalls, and Scenic Trails!
**Reconnect with Nature: The Lotus Room at Maui Eco Retreat**Feel your feet on sacred ground as Nature welcomes you home. Step into the Lotus Room and immerse yourself in the serenity of private trails leading to hidden waterfalls, surrounded by pristine landscapes. Let...
Oceanfront Oasis: Ground Floor Retreat - Sugar Beach #130
Welcome to Sugar Beach Resort #130 – Your Oceanfront Oasis!Experience the serene beauty of North Kihei at Sugar Beach Resort, a picturesque beachfront condominium resort offering breathtaking Pacific Ocean views. Two six-story buildings, equipped with elevators,...
Serene Aloha Retreat: Beachfront Bliss in Napili's Charming Studio/Suite
After opening our doors to wildfire survivors during Lahaina’s time of need, we are honored to once again welcome travelers to our cherished slice of paradise. Our updated studio condo at Napili Shores offers everything you need for a restful, memory-making stay on...
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...
Oceanfront retreat with breathtaking ocean views
Discover the beauty of Maui from Hale Mahina A205, a second-floor, 1-bedroom, 1-bathroom condo that offers a comfortable and memorable island retreat. Designed to sleep up to 4 guests, this spacious, open-concept unit invites you to unwind and enjoy the best of...
Luxurious Kapalua Golf Villa: Stunning 2BR/2BA Retreat with Ocean & Golf Views
Escape to Paradise at our Luxurious Kapalua Golf Villa!Welcome to your dream Hawaiian vacation at this exquisite 2-bedroom, 2-bathroom retreat, nestled in the highly sought-after Kapalua Golf Villas. From the moment you step foot into this tranquil haven, you'll be...
Stunning Oceanfront Retreat, Kahana Reef 218
Direct oceanfront unit in a highly desirable location right in between the popular areas of Kaanapali and Kapalua. When you sit on the balcony, you have panoramic views looking out to the islands of Lanai and Molokai. You will also see whales and sea turtles and have...
Romantic Tropical Retreat, 150 yds from the Ocean!
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...
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...
Private Cliffside Ohana Retreat at Kalapaki Beach!
Experience the very best of Kauai from the comfort & convenience of this luxury oceanfront retreat! Step outside to enjoy incredible ocean views overlooking Nawiliwili Harbor from your private cliffside balcony, or spend the day kayaking, surfing and relaxing on...
Spacious & Modern Pāhoa Retreat Near Kehena Beach!
Discover the very best of the Big Island from the comfort & convenience of this modern private retreat! Ideally situated in the charming town of Pahoa, enjoy the world-famous black sands of Kehena Beach, the warm waters of Ahalanui Park or explore the inspiring...
Oceanfront Sea Village #3212 retreat with stunning views and open living spaces
Turn moments into memories in this incredible oceanfront Sea Village #3212 property. This two-bedroom, two-bathroom has all one is looking for. Enjoy the open layout of the living area and stunning ocean views from the kitchen to the lanai.Upon entry, you can't help but...
New Listing: Tropical 1BR Retreat in Waikomo Stream Villas, Poipu
Welcome to Waikomo Stream Villas unit 100, your tropical gem in the heart of Poipu! Nestled in lush greenery and surrounded by vibrant flora, our one-bedroom condo is the perfect escape for those seeking tranquility and natural Hawaiian beauty.Why you will love this...
Oceanview 5th Floor Retreat Steps from the Beach,
If you're looking for a condo on Maui, look no further. Quiet 5th floor unit in the C Building with views of the ocean, Mt. Haleakala, and the garden from the lanai. Walk across the street to Kamaole Beach Park II for excellent swimming, snorkeling with occasional sea...
Ocean Views, Beach Access, and a Cozy Hawaiian Retreat: Ma'alaea Banyan 416
Maalaea Banyans 416 offers stunning ocean views and is a real charmer, making for the perfect Hawaiian retreat. You can enjoy your morning coffee while watching a whale breach, especially during the season, or turtles almost nightly right from your private...
Oceanfront Retreat w/ Incredible Views Just 90 Seconds from the Beach
Hanalei Colony Resort K4 is a cute and intimate retreat in an off-the-beaten-path location on Kauai's far North Shore, perfect for romantic getaways and escaping the crowds! The sunny and cheerful condo has two bedrooms, with the option to use the second bedroom as a...
Relaxing ocean-view tropical retreat - close to beaches & fun-filled attractions
Kaanapali Plantation Condominiums 20Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Dig your toes into the sand and let your stress melt away when you book your next trip to this...
Seaside retreat - Twelve steps to the sand! Private and romantic.
2024 Traveler Award winning rental, Hanalei Colony Resort I2 is unique among north shore Kauai condo resorts. These Hanalei vacation rentals are directly on the path to follow, just take a few steps and you're on the sand. And I2 is literally just a few steps to the...
Tranquil Groundfloor Retreat - Wailea Ekolu Village 401 - Close to Pool & BBQ!
Wailea Ekolu #401 – Your Ocean View Wailea RetreatSurround yourself with sunshine, palm trees, and endless ocean views at Wailea Ekolu #401. This spacious two-bedroom, two-bathroom ground-level condo offers a serene island escape in one of Maui’s most desirable...
Hoyochi Nikko A Quaint Oceanfront Retreat in Maui
Hoyochi Nikko 202This two-bedroom unit features a master bedroom on the main level with a king-size bed and a spiral staircase leading to a large lofted second bedroom with a queen-size bed. The unit is tastefully decorated with many custom features, and high vaulted...
Kamaka Cabin -A rainforest retreat near Natl. Park
Tucked away on 3 quiet acres of native rainforest, this peaceful Big Island vacation rental is just 2 miles from Volcanoes National Park—the perfect cabin retreat to unwind with family and friends.Purposefully built from cedar boards and beams, this home is uniquely...
Breathtaking Condo #3411: Your Ideal Maui Retreat Awaits!
Welcome to this breathtaking top-floor, Ocean View condo. Immerse yourself in the beauty of your surroundings while enjoying the utmost relaxation.Charley Young Beach, situated mere steps from the condo, showcases immaculate white sands and a family-friendly ocean,...
Kauna‘oa 7B at Mauna Kea – Private Retreat with Pool, Spa & Beach Access
This luxury two-story townhome features four bedrooms (including two primary suites) and 4.5 baths, with its own private pool and spa, in an exclusive gated community. Only about 500 yards from two exceptional resorts and two of the most renowned white-sand beaches on...
Gingerhill Farm Retreat. Commune with Nature In South Kona.
Gingerhill Farm is located on five acres of organic orchards and gardens nestled just above famous Kealakekua Bay. We offer serenity and escape mere minutes away from local restaurants and shops.The Sunset Suite is a large room in the main house with private bathroom...
Maile Retreat ~ Peaceful Home - Kuilima Estates West
This spacious two-bedroom, two bathroom ground floor unit home is your home away from home. Large open living room/dining room is ready to come home to after a long day exploring the beaches or restaurants of the North Shore. Watch the sunrise from your screened in...
Recently renovated 1bd oceanfront retreat
You'll enjoy Papakea Resort A305's amazing oceanfront location! This lovely 1-bedroom, 1-bathroom condo offers some of the best views from Papakea Resort that is suitable to accommodate up to 4 guests. This west-facing condo will provide unobstructed oceanfront seats to...
Honua Kai Hokulani 824: Beautiful Luxury 1BR/1BA, Mountain View Retreat!
This property is hotel zoned, and not being affected by the recent proposed legislation.Honua Kai Hokulani 824! Great location with Mountain views! This one bedroom/one bath located at the highly desired Honua Kai Resort offers the perfect Hawaiian getaway.This inviting...
Charming Retreat with Majestic Ocean Views!
Welcome to one of the best locations in Princeville—beautifully updated with modern flooring, stylish furniture, and fresh island-inspired décor! Perched on a bluff above the sparkling Pacific, this beautifully updated condo at Pali Ke Kua offers sweeping views of...
Unit 107 Tranquil Oceanfront Retreat
A LITTLE ABOUT THIS CONDO.....Welcome to Polynesian Shores 107, your perfect Maui escape where island charm meets modern comfort. This beautifully maintained ground-floor condo invites you to relax and unwind the moment you step inside.Featuring a cozy queen bed in the...