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.
Relax by the sea! Two bedroom retreat near Kailua Pier - 11 min
Discover your tropical retreat at our enchanting two-bedroom holiday house in Kailua-Kona. Paradise is ready for you. Nestled just a short 11-minute drive from the vibrant Kailua Pier, you'll be perfectly positioned to explore the island's top attractions, including the...
Hawaiian Elegance – 5BR Retreat Steps from Mauna Kea & Hapuna Beaches
Welcome to Hawaiian Elegance! From sunrise to sunset, beautiful views surround this exquisite five en-suite bedroom estate in the prestigious Kauna'oa gated community in the heart of the Mauna Kea resort. Hawaiian Elegance is a brand new home just completed in March...
Beachfront Molokai Sanctuary Romantic Getaway Writers retreat Solo Rejuvenations
3 Minute walk to the Beach! Hawaii as you imagined it 50 years ago! Breathtaking beaches only steps away in a serene, uncomplicated paradise of days gone by. Sparkling ocean views from the airy screened in lanai with only the sounds of waves at night and tropical birds...
Endless Ocean Views from your Sugar Beach Retreat -Central AC #208
Come enjoy the amazing ocean views and breathtaking sunsets in our updated deluxe one bedroom, one bath, air-conditioned condo. Sugar Beach Resort, is just steps away from the 5-mile white sandy beach. Our beach access is excellent for swimming, snorkeling, windsurfing,...
Ohana Retreat: 10 BR Poipu Estate with Private Pool, Sleeps 28
OHANA RETREAT AT KOLOA KAI VACATION RENTALSYour Ultimate Group Getaway in PoipuWelcome to Ohana Retreat, a one-of-a-kind vacation rental in Poipu that can accommodate up to 28 guests, making it the perfect haven for large family reunions, retreats, or multi-family...
Spacious Maui Paradise Retreat-Across from 2 Fave Beaches MK-B202
Experience paradise in this fantastic 2-bedroom, 2-bath Maui Kamaole condo. Located in the coveted B building, closest to the main pool pavilion and pristine Kamaole beaches, this newly renovated vacation rental sleeps up to 6 guests comfortably.Highlights:• Prime...
Hualalai Hillside Penthouse Oceanview Retreat
One of only seven Hualalai Penthouse Villas. Upper-level Villa featuring single level interior with over 4,200 sq feet of living and lanai space. Hear the sounds of the Pacific Ocean while enjoying the beautiful close unobstructed ocean and beach views from the generous...
Laule'a 11: Mauna Lani Luxury Retreat with Private Pool & Spa
Welcome to Laule'a at the Mauna Lani Resort #11, your luxury island retreat. This vacation home affords you an immersive Hawaiian getaway experience. As you step inside, your breath will be stolen by the stunning golf course vistas and the majestic Mauna Kea mountain...
Haleiwa Oceanfront Cottage - Charming 1BR Retreat
Discover the delightful onebedroom getaway nestled right within Haleiwa. Nestled just a 22-minute drive from the renowned Banzai Pipeline and 24 minutes from the stunning Turtle Bay Beach, this cozy retreat offers the perfect base for your Hawaiian adventure. ocean...
Kilauea Lakeside Estate - Secluded Luxury Retreat on Private 4-Acre Peninsula
This totally private resort has been described as the best private Kauai retreat in the Hawaiian islands. Located in a wildlife refuge on its own private lake on the island of Kauai, Kilauea Lakeside Estate is a beautifully secluded Hawaiian retreat, simply perfect for...
Maluhia Makai - Luxe Kukui'ula island retreat in Poʻipu; AC, private heated pool
This luxury home is 2200 ft.² of air-conditioned space that opens up to 1000 ft.² of an outdoor living lanai. The design of this home seamlessly marries the indoors & outdoors together to make a grand tropical outdoor experience. Pass through its custom entry wood...
SEABREEZE RETREAT-RECENTLY REMODELED-5 STAR REVIEWS
This beautifully decorated deluxe three bedroom condo is situated in the heart of Waikoloa Beach Resort. With no units above or below, the condo offers the most in privacy. It is newly professionally decorated in Ocean colors with granite and stainless steel appliances....
Sugar Beach Resort 333: Ocean Front retreat with relaxing coastal décor.
Ocean Front retreat with a cool ocean breeze and coastal decor. You will feel relaxed from the moment you enter this one-bedroom ocean-front condo. The bedroom has a king bed, allowing this condo to accommodate up to two guests. The kitchen is fully equipped with...
Kehena Moana Kai - Amazing OCEANFRONT Private Retreat
Perched in the sunbelt at the edge of a dramatic oceanfront sea cliff, this honeymooner’s paradise sits in the heart of the lush Puna District rainforest on the Big Island of Hawaii. With two air-conditioned bedrooms, this private cliff house retreat accommodates up...
Na Hale 3: Exclusive Family Retreat with Private Pool and Resort Privileges
Welcome to Na Hale 3 at Pauoa Beach Club, an embodiment of exquisite indoor/outdoor living nestled in the Mauna Lani Resort, Hawaii's premier destination. This single-family haven is a symphony of luxury and natural beauty designed to offer an unparalleled vacation...
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...
Luxe retreat with hot tub and pool access, private W/D, grill, AC, & gas range
Hale HaupuOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Welcome home to your tranquil Hawaiian getaway! This newly-constructed upscale home is nestled in a quiet neighborhood away...
Premier Oceanfront Retreat in Lahaina
Experience the epitome of luxury at Kaanapali Shores 502. This beachfront residence, renovated in November 2024, offers an unmatched blend of elegance, comfort, and stunning natural beauty. Spanning over 1,500 square feet, this two-bedroom, two-bathroom sanctuary...
Beautiful Kapalua Oceanfront Retreat (989 sq.ft)
Wake up to the sound of waves and sweeping views of Molokai across the channel from this beautifully designed 1000 square foot one-bedroom villa in the Kapalua Bay Villas. Perfectly perched along the dramatic oceanfront cliffs, this ground-floor condo offers...
Puako Pau Hana, A Restful, Private Retreat located steps from the water!!
Puako Pau Hana is a great place to escape from all your cares! Located in the heart of Puako, you are literally just a few steps to the most beautiful little beach in Puako! Puako is known for it's magical old fashioned neighborhood feel and remarkable clear water,...
Hanalei Plantation Road Home - Dream Retreat with Pool & Ocean Views
Escape to this beautiful Hanalei Plantation Road home, nestled in a prized neighborhood. Enjoy sweeping mountain and ocean views over Hanalei Bay. With 4 bedrooms, a gym, pool, and ample indoor/outdoor space, it's a dream retreat. Upstairs, find a bright living/dining...
Family Suite #1 - Two rooms w/ shared hot tub, Family suite # 1 - Ulu Retreat + A'ali'i Sunset Suite
Immerse in tranquility at our Ohia retreat with two serene rooms, each with its own private lanai for enjoying nature's symphony. Indulge in the comfort of 14-inch memory foam mattresses and flat-screen TVs. The courtyard, a blend of open skies and cozy corners,...
Ainamalu 11 – My Favorite Island in the Sun: Waikoloa 3BR Retreat with Lap Pool
vrKCV - Ainamalu 11 - My Favorite Island in the Sun, Professionally Managed by Kona Coast VacationsWelcome to My Favorite Island in the Sun!Escape to this expansive, single-level 3-bedroom oasis, ideal for families, friends, and athletes alike. “My Favorite Island in...
🏖️Sophisticated Oceanfront Retreat | Air-Conditioned | Walk to Beach | vrKCV
vrKCV - The Kona Hideaway at Kona Onenalo No. 11, Professionally Managed by Kona Coast VacationsThe Kona HideawayDiscover the essence of Hawaiian living at The Kona Hideaway, a private oceanfront villa nestled in the exclusive gated community of Kona Onenalo. Adjacent...
OHANA means FAMILY! Stay at the beautiful Ohana Beach Retreat in Keauhou!
Please read listing description for full details on this lovely property! We also have another listing at the Keauhou Surf and Racquet Club if this property isn't available: Vrbo 1620967. We are an approved Short Term Vacation Rental through the state of Hawaii. Ohana...
Magic Sands Retreat: Remodeled Cottage,Walk to Beach, Incredible Location,AC!
The Magic Sands Retreat is a quaint 3 bedroom/2 bath cottage just around the corner from the famed Magic Sands Beach and the Ali'i Drive beach corridor. Just a 10 minute walk to the most popular beach in Kona! This upgraded home shows attention to detail with an artists...
Napili 1st-level serene and peaceful retreat
Welcome to Napili Shores E135, a stunning ground-level 1 bedroom 1 bathroom condo nestled in the heart of Napili featuring a garden view and split AC system. This condo sleeps up to 4 guests. This resort does not have elevators. The living room is enhanced by an...
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...
Relaxing Beachfront Retreat - Sugar Beach #235 - Your Perfect Getaway!
SUGAR BEACH RESORT, #235Welcome to Sugar Beach Resort #235, a beautiful second-floor condo with stunning beachfront views. Perfectly located in North Kihei, this oceanfront retreat offers modern comforts, central AC, and the serene atmosphere of Maui’s longest stretch...
May Cancellation Discounts available. Island Retreat Spacious 3B 3B home.
Aloha and e komo mai (welcome) to Hale Alana, your oasis in Wailea, Maui. Please contact us for seasonal discounts and special rates!Step into Hale Alana, a Polynesian-inspired home situated on a 1/2 acre tropical paradise. With three inviting bedrooms, two being...
Molokai Island Retreat
Aloha and welcome to Molokai Island Retreat! Molokai Island Retreat is located on the highly desirable lush east end of Molokai (we are not on Maui) in the Wavecrest Resort. Our condo offers a breathtaking bird’s-eye view of the ocean, with stunning vistas extending...
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...
New! Luxury Split-Level Retreat at Pili Mai
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...
4 Mi to Beach: Keaau Retreat w/ Relaxing Porch!
'Ke'ena Ma Puna' | Private Outdoor ShowerA tranquil paradise awaits you and your loved one at this cozy 1-bathroom studio in Keaau, Hawaii! After exploring the nearby Paradise Cliffs or Shipman Beach, rinse off in the outdoor shower and unwind on the front porch while...
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...
Luxurious 4 Bedroom Retreat, Private Pool, Located in KuKui' Ula Community.
Situated on the upper tier of the Kainani neighborhood in the beautiful Kukui'ula Community, this exquisitely designed, newly constructed custom home, features custom imported teak flooring, cabinetry, vanities, trims, natural wood, stone, lava rock, and hand selected...
Pinnacle: Upcountry Maui Retreat with Pool & Ocean View
Permit: STPH 2013/0024TA-091-083-1616-01 / GE-091-083-1616-01TMK-270031060000Fabulous views, privacy and quiet were foremost for us in choosing where to build our dream home in Hawaii. We looked for several years before finding this special Maui hilltop location on the...
Hawaiian Retreat w/ Ocean Views in Captain Cook!
Indulge in the ultimate Hawaiian getaway at this stunning 3-bed, 3-bath vacation rental house in Captain Cook. Upon arrival, you’ll be greeted by 3 manicured acres of mature fruit trees. Past the front door lies access to the ocean-view lanai, which is the perfect...
Hawaiian Chic Crater Retreat- a tropical jungle escape in a secluded crater
***FYI- swimming pool will be closed April 15th-May 15, 2024 for repairs***Being on the ocean is amazing, but is it as amazing as having a one of a kind condo in a secluded crater? It has many of the same amenities as a $1000/night nearby resort does, for a much better...
Spacious Lanai Retreat: Kapalua Maui's Golf Villa with Breathtaking Views 14T 1-2
This is a legally permitted vacation rental according to the County of Maui ordinances.Spacious Lanai Retreat: Kapalua Maui's Golf Villa with Breathtaking ViewsImmerse yourself in the epitome of luxury with our recently refurbished 1-bedroom, 2-bathroom condo, nestled...
Kaanapali Royal B201: Your Dream Hawaiian Retreat
🌴 Escape to Paradise: Your Dream Vacation Awaits at Kaanapali Royal B201 🌺Imagine waking up in the heart of Kaanapali (Kāʻanapali), where the gentle sounds of swaying palm trees (nā niu) and the scent of tropical flowers (nā pua) welcome...
Luxe Tropical Retreat w/ Private Pool, Spa, AC, Golf Cart Included
This newly constructed split-level home features an open floor plan, only the finest finishes, and its own pool and jacuzzi, along with access to the KaMilo pools, fitness center, and other recreational facilities. Luxuriously appointed, it creates a peaceful atmosphere...
Private Kōloa Retreat | Pool + Golf Course Views | Near Poʻipū 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...
Menehune Shores #119 – Stylish Oceanfront Retreat with Luxe Modern Finishes
Menehune Shores #119Experience effortless oceanfront living at Menehune Shores #119, a welcoming ground-floor condo with beautiful views and direct access to the grassy lawn and beach. This two-bedroom, two-bathroom retreat is thoughtfully designed to offer comfort,...
Oahu North Shore 2 BR Oceanfront Retreat at Sunset Beach
Escape to the stunning shores of Haleiwa and experience the ultimate beachfront getaway at our charming vacation rental. Nestled along the pristine sands and turquoise waters, this slice of paradise offers an idyllic setting for relaxation, adventure, and unforgettable...
Expansive One-of-a-Kind Retreat - 3 Oceanview Lanais - Makena Surf G 301-302
Makena Surf #G-301-302Welcome to Makena Surf #G-301-302, an expansive and newly remodeled four-bedroom, five-bathroom oceanview penthouse with a private den, located in the exclusive Makena Surf Resort. With elegant design, premium finishes, and three private lanais,...
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....
6 mins from Nat'l Park! Enjoy the sound of rain & birds in a peaceful retreat.
Hawaii State Tax ID: 148-388-6592-01. Hawai'i County IDs: STVR 19-345557, NUC 19-293Aloha! E komo mai. Welcome to Fern Cottage. Located across from Volcano Village, and just minutes from Hawaii Volcanoes National Park, we invite you to make our fully permitted house...
Tropical Paradise Retreat in Princeville! Full Kitchen, Swimming Pool!
Set on the picturesque North Shore of Kauai, this resort offers stunning ocean and mountain views with easy access to Hanalei Bay’s beaches and hiking trails. Ideal for nature lovers, it provides a serene getaway close to local shops and dining options.This listing is...
🌴 Gorgeous Oceanfront Luxury Retreat 🌊 Pool, black sand beach, AC and billiards
We are THE perfect luxury listing on the east side of the Big Island! A quick distance to black sand beaches, waterfalls, the volcano and charming Hilo town. ALOHA! Welcome to Hale Kakahi or Hawaiian for “unique, outstanding, one-of-a-kind house” -a perfect name for...