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.
Sunset Beach House – Polynesian-Style Beachfront Retreat
A Note About The $1,530/nt Rate: It is calculated from my standard rate of $1,700/nt with a 10% discount that brings it to exactly $1,530/nt. Please note, It is only for dates that are very close to the current date that I have not been able to book so I lower the price...
Gorgeous Oceanfront Retreat! Marvel at the Stunning Views from Sugar Beach #326n
SUGAR BEACH RESORT, #326One Bedroom / One Bath Oceanfront CondominiumWelcome to Sugar Beach Resort #326, a beautiful one-bedroom condo with direct oceanfront views and updated interiors. Perfectly situated in North Kihei, this retreat combines comfort, modern upgrades,...
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...
Luxurious 3BR/3BA Retreat with Private Beach Club Access in Mauna Lani
Summary:Escape to paradise at this luxurious townhouse in Mauna Lani Resort, perfect for families! This spacious 3-bedroom, 3-bathroom home with a loft comfortably sleeps 8 and offers resort-style amenities. Enjoy the exclusive gated community of Mauna Lani Palm Villas,...
Hale Kolea - Luxury Lanikai Hillside Retreat
Hale Kolea is perfect for families and larger groups... A 3 story home at the end of Lanikai with access to an exclusive secluded beach within a gated drive. This beautiful home is on a hillside overlooking the crystal clear, gorgeous blue and green hued water. Wake up...
Sweet retreat close to the ocean. Where natures sights and sounds delight soul.
GE-186-363-6992-01 TAT186-363-6992-01This colorful 2 bedroom 2 bath home is Hosted from the front cottage. Close to all the fun Puna has to offer. The quiet setting has privacy with room for family & friends. Let the sound of the waves rock you to sleep. Maybe even hear...
M. KoOlina Beach Club Oceanfront Resort, Beautiful, Tropical Oceanfront Retreat!
Please choose a Friday through Sunday check-in for a seven night stay. Rates are based on a garden view and will fluctuate for holiday weeks. Thank you for your interest in booking with Dash Realty Group, Windermere Florida. Dash Realty Group is registered in Florida as...
Eastside Zen Retreat, Pono Kain4/25-5/3 - Discounted 15%
Without a doubt, the Pono Kai Zen Retreat is the finest unit on this 15 acre property. This 2 bedroom 2 bath condo is literally only steps to the warm Pacific Ocean! Golden sunrises, warm trade winds, and shimmering waters next to a mile-long sandy beach. Those are just...
Island retreat with a pool, BBQ access, private lanai, washer/dryer, central AC
Kauai Kailani 109Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Aloha paradise! This beautiful Kauai Kailani property features all of the amenities you love to have while on...
Natural Light End Unit Kuilima East Steps to Pool-BBQ-Parking Golf Retreat
Book with confidence! This property is professionally managed by Ali'i Beach Rentals, an award-winning property management company.Welcome to this stunning vacation rental, ideally located on the world-renowned North Shore of O'ahu, within the exclusive Turtle Bay...
O-523 Sunset Hale Retreat - Ko Olina Beach Villa. Steps to the Pool and Beach!
Welcome to our Sunset Hale Retreat - Ko'olina Beach Villa. Steps to the pool and beach!Amazing beachfront condo in the Ko'Olina resort overlooking swimming pool with beautiful pool and sunset views! Pristine residence features spacious living area and lanai with pocket...
Escape to paradise at Mauna Lani B208, an exceptional oceanfront retreat
Mauna Lani B208 Oceanfront Vacation Rental – 2 Bed, 2.5 BathEscape to paradise at Mauna Lani B208, an exceptional oceanfront retreat offering unparalleled luxury and breathtaking views. This stunning 2-bedroom, 2.5-bath condo is situated in one of Hawaii's most...
Pua Oriana: A Polynesian Tropical Retreat
E komo mai — welcome to our hale. Welcome to the Pua Oriana – a mix of Hawaiian and Samoan language, ‘pua’ meaning flower, and ‘oriana’ means the flower that adorns a woman’s head. Enjoy the space and the grounds with 880 acres of pristine gardens, walking...
Chic Kihei Beach Retreat with Ocean Views across from Charley Young Beach
Our 2 bed, 2 bath unit has been remodeled, including a three zone mini-split A/C system, quartz counter tops, tile floors, open concept kitchen, and custom tiled showers. New stainless steel appliances, including full-size fridge, dishwasher & microwave, large capacity...
Hale Malie - a peaceful rainforest retreat minutes from Volcano National Park!
Hale Malie is a charming 1-bed/1-bath cottage retreat on a private half acre of lush Hawaiian rain forest just minutes from Volcano National Park. Featuring vaulted ceilings, a full kitchen, a sunny dining area, and expansive covered lanai, this cottage is ideal for two...
Kailua Beach Oceanfront Estate – Grand 6-Bedroom Retreat on Oahu’s Shores
This property is professionally managed by Private Homes Hawaii, LLC, a licensed brokerage in the State of Hawaii (RB-21170). It is licensed as a short term vacation rental, Non-Conforming Use Permit Numbers 1990/NUC-1777/1778 and is compliant with Hawaii State...
Deluxe Ka'anapali Condo with AC Luxurious Retreat
**Kaanapali Plantation #16 – Your Peaceful Island Getaway**Welcome to Kaanapali Plantation #16, your serene island retreat with expansive views of lush landscapes, the Royal Kaanapali Golf Course, and the islands of Lanai and Molokai, all framed by the stunning blue...
Private Hidden Retreat On North Shore Near Beach!
Discover Ha‘ena Place | North Shore Kaua‘iNestled on a quiet cul-de-sac, Ha‘ena Place is a true hidden gem—just a short stroll to some of Kaua‘i’s most iconic North Shore beaches, including Tunnels (Makua), Ke‘e, Lumaha‘i, and Hanalei Bay. Whether...
Mountain-view retreat with 2 suites, pool & hot tub - near restaurants & beaches
Villas of Kamali'i Apt 20Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'At the Villas of Kamali’i 20, you get it all - a convenient, split-level floor plan, gorgeous finishes, and...
Private Island Retreat. Tropical Sanctuary.
UALANI RETREAT Fully Licensed & Permitted. Locally Owned & Operated B&B BBPH 2012/0002 SUP2 2012/0001Terrific Discounts Thru October. Private detached 1 bedroom cottage on 3 acre tropical retreat. Lush haven surrounded by fruit trees and bamboo groves. Nicely equipped....
Maile Hale: Private Oceanview Retreat w/ AC, Near Beaches & More
This single-level ocean-view home in the prestigious, gated Keauhou Estates community blends comfort with effortless island living. Just minutes from beaches, dining, and shopping, it offers spacious interiors, lush gardens, and sweeping coastal and mountain...
Hale Maluhia: 2 BR Hanalei Bay Beachfront Retreat
Experience paradise at Hale Maluhia, an exclusive beachfront home on the idyllic Hanalei Bay. Perfect for honeymooners or small groups seeking a luxurious escape, this stunning property offers unparalleled privacy within a gated enclave.Indulge in the epitome of comfort...
Kehena Beach Oceanfront Retreat - Incredible Views of Ocean from Every Room
Discover the ultimate oceanfront retreat on the Big Island at Kehena Cliffside Estate — a private, gated luxury rental designed to showcase breathtaking views of the Pacific Ocean from nearly every room. Nestled along the dramatic cliffs of Kehena, this spacious...
Haena Beach House – Luxury Oceanfront Kauai Retreat
TVNC 1258Haena Beach House offers a once-in-a-lifetime vacation experience, providing contemporary luxury in a private beachfront setting. Ideal for large groups, the home showcases breathtaking panoramic views of the Pacific from its living spaces and each of its...
Paradise Retreat, POOL, Hot Tub and AC with ECO energy!
Paradise Retreat is your own private resort on Hawai'i’s Big Island. Relax and enjoy the swimming pool and hot tub in our private, fully enclosed back yard. Lounge poolside in the sun-soaked chaise chairs or stay cool on the covered lanai. In the evenings, enjoy...
Deluxe Island Retreat-Newly Remodeled - SUMMER SPECIAL
Paradise awaits you at this lovely seaside condo...….Relax amidst the lush tropical landscape that welcomes you to Ali'i Kai Condominiums. This ground-level unit opens up to an expansive tropical jungle on the “Mauka” (mountain) side, and to partial ocean views on...
Upscale Executive Retreat--Newly Renovated and Air Conditioning!
This newly renovated upscale condo is stunning! All new bathrooms, kitchen, flooring, and furnishings. Condo is very clean and comfortable and gets a great breeze, and we also have AC. We are located on the ocean facing section of the complex. Your comfort and...
Newly updated ocean view retreat on Poipu Beach; A/C, pool, gym restaurants.
A Perfect Day in Paradise...Greet the morning with freshly brewed coffee on your spacious lanai with expansive garden and ocean views from this top floor unit. Making breakfast is easy in your bright, beautiful open kitchen with stainless steel appliances. Then pack up...
Waikoloa Colony Villas 204-Golfers Retreat with Gold Golf Membership Discount
Newly remodeled 2 bedroom, 2 1/2 bath Waikoloa Colony Villas townhouse located off the 9th hole of the Waikoloa Beach Nine. Discounted GOLD GOLF KINGS' CLUB MEMBERSHIP. Book this villa and you will be able to set up your tee time and golf at discounted rates. This unit...
Stunning retreat w/ a full kitchen, gas fireplace, furnished lanais, & free WiFi
Pele Noe - 3 Miles From Volcanoes National ParkOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Nestled into a native Ohia Lehua forest, this Big Island vacation rental is...
Captivating Ocean View Retreat: Spacious Beauty at Wailea Elua #902
Wailea Elua #902 – Newly Remodeled Ocean View Escape with Upscale Island StyleWelcome to Wailea Elua #902, a beautifully updated second-floor, 2-bedroom, 2-bathroom condo that offers comfort, luxury, and peaceful ocean views in one of Wailea’s most sought-after...
Gorgeous, Newly Remodelled Ocean Front Retreat-Sea Lodge II G6
Come experience the most Amazing views in this Second floor unit in Sealodge. Handcrafted Hawaiian hardwood accents as well as bright & beachy décor to invite you to this beautiful North Shore, piece of paradise here in Princeville, Kauai. The condo rests atop a cliff...
Hawaiian Family Paradise Retreat – Near Beach & Golf!
Escape to your paradise in this luxurious Hawaiian retreat! This exquisite home offers the perfect blend of relaxation and convenience. Just minutes from the Kohala Gold Coast’s finest beaches and resorts, a short walk to local shops, restaurants, a community pool,...
Superior Retreat W/Lanai and Kitchen–Poipu Shores
Castle Po'ipū Shores 301A: Live like you own Kauai’s sunny Poipu Coast! Pure nirvana at the ocean’s edge, this 913 sq ft Superior Ocean Front suite wows with waves crashing against lava rocks just feet beyond your private lanai. Why leave your “home away from...
Kona Pacific Top Floor Retreat: Ocean View & Pool!
Say aloha to this exquisite 1-bedroom, 2-bathroom Kailua-Kona vacation rental condo nestled in the scenic Kona Pacific complex! Featuring A/C, updated amenities, and a fully-equipped kitchen with a Burr grinder for your Kona coffee, this inviting Hawaii residence has...
Puamana 177-3 – Elegant Garden Retreat in South Puamana
Escape to the tranquil beauty of Puamana in this tastefully remodeled 2-bedroom, 2.5-bathroom townhome, ideally located in the lush, tropical oasis of South Puamana—untouched by the 2023 Lahaina fire. This peaceful location offers quick access to the nearby beach,...
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...
Oceanfront Family Retreat: 2BR Condo Unmatched Views, Easy Beach Access, 100% AC
Enjoy spectacular, sweeping, front-on views of the Pacific from the living room, bedroom and lanai of this spacious 1483 sq. ft. 8th floor two-bedroom, two-bath corner unit at the Mahana on Ka'anapali Beach - rated as one of the best beaches in the world. With private...
Modern Luxury 2nd-Floor 2Bd/2Ba Retreat with Ultra-Quiet A/C, & 6'x5' Shower
About Grand Champions Villas 128 (Hawaii Tax ID: 104-909-0048-01):This roomy 2-bedroom 2-bath second floor unit is situated in the serene Wailea Grand Champions Villas. It offers luxury amenities, such as super quiet central air conditioning, a private lanai, in-unit...
Kiahuna 323 - Ohana Garden Retreat - Garden Deluxe View overlooking Moir Cactus Garden
KIAHUNA PLANTATION 323 - OHANA GARDEN RETREAT AT KOLOA KAI VACATION RENTALSSerene Garden Retreat in the Heart of Poipu BeachWelcome to Kiahuna Plantation 323, lovingly known as the Ohana Garden Retreat, where tropical beauty and modern comfort blend seamlessly. This...
Stunning 2 bedroom retreat. Perfect location for exploring beautiful Maui!
2 bedroom, 2 bath, sleeps 7 ~ non smokingYour vacation dreams will be realized with this beautiful two bedroom, two bath tropical retreat.Imagine waking up to the sound of the ocean, tropical birds, and a babbling Koi pond fountain. This condo is well appointed with...
Puna ZEN Botanical Garden Retreat near Volcano Nat. Park, Hilo, Kehena Beach
Escape to a charming traditional Hawaiian home, elevated on post and pier for enhanced airflow and privacy. This unique blend of classic architecture and mid-century design features an open-concept great room, complete with a sunken living area, dining space, and...
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...
Makaha Sunset Retreat
This 5th floor beachside corner apartment offers 180 degree view of the ocean and the fantastic waves of world renown Makaha beach rich with ocean life. Enjoy the view from a wrap around lanai or from the queen sized bed. A full sized pull out bed in the living room...
Island Chic - Zen Retreat - A/C in 2 Bedrooms
Welcome to your modern haven of island living, where sleek design and thoughtful amenities converge to create a stylish retreat. This residence boasts not one but two master suites, a well-appointed guest room, a private office with a sleeper sofa and a range of...
Luxurious 2BR Mana Kai Retreat: Panoramic Ocean Views, Modern Amenities
Absolutely stunning, fully remodeled vacation rental with panoramic ocean and island views! Get ready to experience a truly luxurious tropical getaway in a location that will leave you breathless. Here are the incredible features of our rental:Panoramic Ocean and Island...
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...
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,...
"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...