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.
Charming 2BD + Den Retreat in Princeville – Near Hanalei Beach
Stay near the beaches and beauty of Kaua‘i’s North Shore at Casa La Ola, a modern 2-bedroom + den condo in the heart of Princeville. Enjoy ocean views, walk to Queen’s Bath, and unwind in the pool and spa just steps from your door.Located in one of Princeville’s newest...
Stunning Views & Swaying Palms from your 5th-Floor Oceanfront Retreat
Welcome to your peaceful Maui getaway—a beautiful 5th-floor oceanfront condo with sweeping views of KahoÊ»olawe and LÄnaÊ»i islands. From your private lanai, watch palm trees sway over sparkling blue waters and feel the gentle quiet that defines this part of West Maui.Our...
Mystic Mermaid Island Retreat! Entire Home
This home is not your typical VRBO, this home is designed for guests who appreciates CLEANLINESS, COMFORT, CARE, SAFETY AND QUALITY! Escape to Your Mystic Mermaid Island Retreat, your private, spacious oasis near Oʻahu’s majestic mountains! NO neighbors behind the home...
Poipu Retreat: 3BR with Ocean & Golf Views, Lanai Sunsets, Pool & Central A/C
Welcome to Pili Mai 8C – Your Private Poipu Retreat.Perched on the edge of the scenic Kiahuna Golf Course, Pili Mai 8C is a three-bedroom, three-bath condo that captures the very best of Kaua‘i living. With sweeping views of the ocean, golf greens, and surrounding...
Kaia Villa, at Turtle Bay - Modern North Shore Oahu Retreat w/Lanai & Golf Views
Debuting October 2025. Kaia Villa offers a newly renovated stay on Oahu's famous North Shore. Set within Turtle Bay Resort , This property has been thoughtfully transformed into a stylish island retreat designed for comfort and relaxation.Every detail has been curated...
Breathtaking 1 Bed True Oceanfront Retreat Maui
Aloha, E komo mai—welcome to paradise at Napili Point Resort in Maui, Hawaii. You'll fall head over heels for this 5-Star (1 of a kind A Unit), BRAND NEW oceanfront 1-Bedroom Condo, boasting a gorgeous Island Kitchen, luxurious dream shower & comfy Stearns & Foster...
Golf Course View Retreat | Wailea Condo GC100 | Walk to Shops & Beaches
Welcome to Grand Champions #100, a meticulously updated 2-bedroom, 2-bathroom villa located in the heart of Wailea. Overlooking the 3rd hole of the Wailea Blue Golf Course, this spacious retreat features vaulted ceilings, modern upgrades, and spectacular views of...
STVR Home - Kona’s Cozy Retreat - 4Bd/3Bath/Sleep 12/Pool with AC
Welcome to your perfect Hawaiian getaway! Nestled in a serene neighborhood in Kailua-Kona, our charming home offers everything you need for a memorable stay on the Big Island. Whether you’re here to explore the island's natural beauty, relax by the pool, or simply...
Elevated Island Elegance in Kukui'ula - A Refined Retreat in Poipu
Graciously set within the exclusive enclave of Kukui'ula, this thoughtfully designed 3-bedroom, 3.5-bath residence offers an elevated South Shore experience—both in setting and sensibility. Wrapped in the soft embrace of trade winds and tropical foliage, the home...
Hilo Lagoon Retreat – 2BR w/View, A/C, Pool
Relax and Unwind at Hilo Lagoon CenterWelcome to your home away from home in the heart of Hilo! This spacious 2-bedroom, 2-bathroom condo offers comfort, convenience, and beautiful views of the peaceful waters at Wailoa River State Park.The spaceInside, you’ll find:Two...
Boldly Oceanfront. Stylishly Maui. Royal Mauian 2-Bedroom Retreat
*This is a NEW listing and it's gorgeous! This is not your average beach condo! This stunning 2-bedroom, 2-bath unit at the Royal Mauian is oceanfront living with purpose; fully renovated, thoughtfully designed, and infused with island energy throughout.The decor is...
Wailea Ekahi 24B - Modern Garden Retreat w/ Lanai, Split AC & Stylish Renovation
Nestled on the ground floor, Wailea Ekahi 24B is a beautifully remodeled one-bedroom, two-bath condo featuring a sleek, modern design and effortless indoor-outdoor living. With elegant finishes throughout, including quartz countertops and stainless-steel appliances,...
Puna Rainforest Retreat Hotspring - Purple Passion Cottage
The Purple Passion Cottage is located on a serene 20 acre estate with beautiful ocean and meadow views. The cottage is cozy and equipped kitchenette (range, oven, mini-fridge/freezer, microwave), full bathroom and two bedrooms. The main bedroom has a king bed with an...
Puna Rainforest Retreat Hotspring - Blue Ginger Cottage
Puna Rainforest Retreat Blue Ginger Cottage has a complete kitchen with all the amenities, a full bathroom and cozy queen size bed. Perfect for couples. This colorful cottage is clean, comfortable and affordable! Enjoy the rainforest trail, steam vents, plunge pool,...
Hale Maia at Kukui ula - Elegant Pool Retreat with Golf Views in Poipu
Summary:TA-101-738-2400-01Discover Hale Maia at Kukuiula, a stylish and spacious 5BR, 5.5BA home in Kauai’s most exclusive community. This modern retreat features panoramic fairway views, a private heated pool, and seamless indoor-outdoor living. With each bedroom...
Jungle Retreat in Kona Cloud Forest Sanctuary, An unforgettable Cloud Forest Sanctuary retreat exper...
Wake up in your cozy private jungle retreat nestled in the lush serenity of the Kona Cloud Forest Sanctuary. All stays include a private guided Sanctuary tour. Enjoy yoga, sound baths, and other experiences on site, take a morning walk for fresh brew and coffee tours at...
Tropical Bamboo Retreat in Upcountry Maui! Bamboo Heaven Maui LLC BBPH 2012/0003
Consider this bed & breakfast your home away from home while you visit Haiku Maui! This tropical property offers a peaceful retreat in the country with fruit trees, rainbows, and night skies filled with stars and galaxies! My unique bamboo home welcomes you to unwind...
Private KÅloa Retreat | Pool + Golf Course Views | Near PoÊ»ipÅ« Beach
Discover this lovely 3-bedroom gem in Kōloa. This awesome house features two king beds and two queen beds perfect for families or friends looking for a relaxing island retreat. With three full bathrooms including walk-in showers, a soaking tub in the master suite, and a...
Maui Kamaole #C-203 - Remodeled Upstairs Retreat with AC and Resort Pools!
Maui Kamaole #C-203Maui Kamaole #C-203 is a beautifully remodeled two-bedroom, two-bathroom upstairs unit offering a peaceful setting, modern comfort, and a fantastic location near some of South Kihei’s best beaches. This updated condo features island-inspired décor,...
Emmalani Hale, High-end, Luxurious, Tranquil retreat, AC in Princeville
Welcome to Emmalani Hale, your perfect retreat in Kauai!More than just a vacation rental, Emmalani Hale offers a luxurious and welcoming island escape designed for relaxation and comfort. This beautiful 3-bedroom, 3-bathroom home with large spacious living space,...
KaMilo #503 by Gather: Luxury Mauna Lani Retreat Near Golf & Beach
Welcome to Mauna Lani KaMilo #503, a serene three-bedroom, three-bath villa tucked within the private gates of Mauna Lani Resort on Hawai‘i’s Big Island. Thoughtfully designed for seamless indoor-outdoor living, this residence combines island-inspired luxury with all...
Luxurious 2-Bedroom Retreat in the Heart of Waikiki.
Waikiki Landmark Unit 2901. Escape to paradise in this spacious and luxurious 2-bedroom, 2.5-bathroom condo at Waikiki Landmark, Unit 2901. Located in the heart of Waikiki, this expansive unit offers everything you need for an unforgettable Hawaiian vacation. Fully...
NEW Modern Family Retreat - Hanalei Happiness - Near Best Beaches, Trails & Eats
Step into an elevated retreat, thoughtfully designed for traveling families. This modern hideaway is rich in amenities and curated for comfort, all while embracing the vibrant spirit of Hanalei.- Just 8 Minutes to Hanalei- Close to Best Beaches, Trails & Eats- Ultimate...
Luxury Oceanview Wailea Retreat with Sunset Views
Escape to HÅkÅ« Hale, a serene oceanview retreat in the heart of Wailea. This designer oasis offers modern comforts, a private lanai with stunning ocean views, on the fairway of a private golf course. Walk to world-class beaches, dining, golf or relax in a peaceful,...
EXTRAORDINARY Hale Kuikahi Oceanfront Retreat - fully airconditioned!
Step onto the grounds of our oceanfront botanical garden retreat - Hale Kuikahi! Located in the quiet Paukaa area of Hilo just above famed Honolii surf beach, Hale Kuikahi boasts a private botanical garden walk onsite. Enjoy sweeping oceanfront views from almost every...
New! Luxury Split-Level Retreat at Pili Mai 15E
Luxury Split-Level Retreat at Pili Mai #15E | Poipu ParadiseProperty OverviewWelcome to this stunning split-level home at the prestigious Pili Mai Resort in sun-soaked Poipu, Kauai. This immaculately maintained 3-bedroom residence offers the perfect blend of Hawaiian...
Stunning Ocean-View Retreat Overlooking Laupahoehoe Point
Welcome to your tropical escape! This stunning three-level home boasts panoramic ocean views and a tranquil setting, making it ideal for a peaceful and rejuvenating vacation.With 1,500 square feet of space, the main living areas are located on the upper level, while the...
Hanalei Bay View Retreat - An Artistic home overlooking Hanalei Bay
Welcome to Hanalei Bay View Retreat, overlooking Hanalei. Nestled at the edge ofPrinceville/Hanalei and centrally located to stores and restaurants as well as all the NorthShore’s best adventures. Adjacent to a forested greenbelt just beyond your windows, you’ll...
Beachy Kona Getaway. Located within walking distance to the heart of Kona Town.
Welcome to our dreamy Kona getaway! This newly refurbished, luxury beachy retreat is designed for relaxation and convenience in the heart of Kailua Kona. Walking distance from Kona`s best restaurants and bars, it provides easy access to Ali`i Drive and all it offers,...
Oceanview Retreat in Puamana – Steps from the Beach & Surf
Nestled just a 30-second walk from the beach and three popular surf breaks, this beautifully remodeled 3-bedroom, 3-bathroom townhome in Puamana offers the perfect blend of modern comfort and laid-back island living. Located on the safe side of Puamana, untouched by the...
Hale Konane – Oceanview Luxury at Mauna Lani Resort
Hale Konane blends Big Island elegance with relaxed island living in the heart of Mauna Lani Resort. Set along the 17th green of the South Course, this 5-bedroom, 5-bathroom single-level estate offers sweeping golf and ocean vistas, refined interiors, an outdoor retreat...
Your Tropical Kona Retreat - Breezy Condo Steps from Beach
The perfect blend of comfort and convenience. Shaded by palm trees and on the second floor, the light breeze keeps the temperature perfect. The one bedroom/one bathroom unit features a fully stocked kitchen, private lanai with garden view, and a dedicated parking spot....
Hilo Studio Retreat with Gorgeous Park View, AC, WiFi, Pool
Welcome to your cozy getaway! This inviting studio is thoughtfully designed for comfort and convenience, making it the perfect home base for your adventures.Step inside to find a bright and airy living space, complete with a comfortable bed and stylish furnishings. The...
Wailea Oceanfront Center Front Row Luxury Retreat
Immerse yourself in the beauty of Maui at this stunning oceanfront property. This 2-bedroom, 2-bathroom condo offers center unit front row access of the Pacific Ocean.The primary bedroom features a king-sized bed with direct access to the lanai. The second bedroom...
Peaceful 1-Bedroom in a Quiet Community
Experience the beauty of the Big Island from this beautifully remodeled 2-bedroom condo at Keauhou Punahele, perfectly situated next to the scenic Kona Country Club. This inviting retreat blends modern comfort with authentic island charm, offering the perfect space to...
Top Floor Retreat w/Mtn Views & Beach Access, 1537
Located on the top floor, this stunning, air-conditioned retreat offers the ultimate in luxury. With no stairs to navigate and steps from parking, you'll enjoy effortless access to your private oasis, complete with breathtaking views. No matter your vacation needs, this...
Top Floor, Retreat w/Mtn Views & Beach Access, 1538
Unit 1538 is a cozy and inviting retreat perfectly suited for a relaxing getaway. This spacious studio features a comfortable king-sized bed, a full kitchen, a washer/dryer, and a large bathroom with a walk-in shower. The room is also equipped with a large flat-screen...
🏝️SUMMER Deals - Walk to the beach, great and convenient location LSV15🏝️
South Maui Condo Steps from the BeachWelcome to our bright and airy second-floor end unit in the heart of Kihei. Located in Building 4, Unit #223, this condo offers windows on three sides, allowing natural light and refreshing trade winds to flow through.What Makes This...
Pualani Villa by Gather: Luxe Princeville Retreat w/ Pool & Hot Tub
Escape to Pualani Villa by Gather, a stunning three-bedroom + den, 2.5-bathroom townhome in the heart of Princeville’s prestigious resort community. Offering a beautifully designed living space, this two-story retreat combines modern luxury with island charm, creating...
Cozy 3bd/3b Beach Retreat, Sleeps 10, AC, WiFi, Fam-Friendly in fantastic Koloa
Escape to paradise in this relaxing 3 bed/3 bath retreat at the Pili Mai condos located on the Kiahuna golf course. This unit can sleep up to 10 guests, relax in its plush interiors with a king bed, 1 queen bed and a cozy bunk room (1 queen, 1 full, 2 twin beds),...
Pili Pono: Elegant Honolulu Retreat with Pool & Private Oasis
Welcome to Pili Pono, a show-stopping 5-bedroom, 6.5-bath luxury estate set within Honolulu’s prestigious Black Point enclave. Spanning 7,470 sq ft of indoor–outdoor living space on a fully enclosed, gated 0.33-acre lot, this custom-designed retreat blends architectural...
Spacious retreat with hot tub & BBQ grill
Summary:Ocean Front Pool/Hot Tub, Near Golf /Beach, TennisThe Space:Welcome to your Hawaiian retreat at Waikoloa Beach Resort - perfect for families & groups seeking relaxation by the coast! Enjoy peaceful garden views, resort amenities & easy island living:- Sleeps 6 |...
Ko'Olina Retreat - Short Walk to Resorts, Golf, Restaurants & Lagoons!
Welcome to your dream retreat in the heart of Ko'Olina! This beautifully remodeled 3-bedroom, 3-bathroom townhome is nestled in the exclusive, gated community of Ko'Olina Kai, offering the perfect blend of luxury, comfort, and island charm.Step inside and be captivated...
Hale Kai'opua - Modern Kauai Retreat with Private Pool & Lanai
Welcome to Hale Kai‘opua at Kukui‘ula, a stunning 3-bedroom, 3.5-bath luxury retreat set above the postcard-perfect South Shore of Kauaʻi. Spanning 2,961 sq ft of contemporary indoor–outdoor living, this newly built 2024 residence blends modern architecture with wide...
Luxury Waikoloa Retreat: 3BR, Hilton Pool Pass!
Welcome to this spacious 3-bedroom townhome, perfectly located in the heart of Waikoloa Beach Resort. With lush landscape views, a short walk to the beach, and complimentary Hilton pool passes, this home offers the ideal setting for your island getaway. Accommodating up...
Hawaiian Treehouse, Peaceful Glamping Retreat
BAUMHAUS - a fully off-grid 12 feet high tree house on 2 acres of tropical rainforest on the Big Island of Hawaii. Experience stargazing like no where else in the world, while warming up at the fire pit. Chill out in the large hanging net or spend rainy days in the hot...
Tranquil 1-Bedroom Haven in Kapaa, Kauai - Your Perfect Island Retreat
Welcome to our charming 1-bedroom, 1-bathroom condo in the heart of Kapaa, Kauai! Perfectly located for exploring the island, this cozy retreat offers a fully equipped kitchen, comfortable living space, and a private lanai to enjoy the tropical breeze. Just minutes from...
Hale Ka Pua Ola – Private Luxury Retreat in Kukui'ula
Welcome to Hale Ka Pua Ola at Kukui‘ula, an elegant 4-bedroom, 4.5-bath luxury retreat set within Kaua‘i’s prestigious Kukui‘ula community. Offering over 3,048 sq ft of refined indoor–outdoor living, this single-level sanctuary blends contemporary design with the...
New Listing! Peaceful Poipu Retreat Waikomo 200
Experience the perfect blend of serenity and convenience in this beautifully updated one-bedroom corner unit at Waikomo Stream Villas. Nestled among lush Hawaiian foliage, this modern retreat offers a peaceful jungle atmosphere while being just steps away from Poipu's...
Kalama Terrace Renovated Retreat, Centrally Located with AC!
Welcome to Kalama Terrace: Your Stylish, Centrally Located Kihei Retreat!Step into island living at Kalama Terrace, Unit P211—an inviting, fully renovated condo in the heart of Kihei. Perfectly situated just a short stroll from the sandy shores of Kamaole Beach and...