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.
Hale Ho'okipa, Hale Ho'okipa a Quiet Rain Forest Retreat
This quiet mountain hide-a-way offers peace and serenity in a rural location close to Hawai'i Volcanoes National Park. The private home has covered private lanais with eating areas, lounging areas and a fire pit. Interior spaces have a unique Hawai'ian vibe with...
Honeymoon Bliss: Bamboo Temple with Ocean Views at Maui Eco Retreat
**Bamboo Temple – Secluded Honeymoon Cottage with Stunning Ocean Views**Discover the perfect romantic escape at Bamboo Temple, an idyllic private cottage for honeymooners and couples seeking serenity. Wake up to breathtaking sunrises over the Pacific Ocean and fall...
Oceanview Paradise: Tropical Retreat in Wailea
Welcome to our beautiful, elegantly remodeled 2-bedroom, 2-bathroom condo in the prestigious Wailea Grand Champions Villas. Perched on the 2nd floor, this luxurious condo offers breathtaking ocean views and a spacious, open floor plan with tasteful modern finishes.Upon...
Ohana Retreat - Private Pool, Sleeps 29
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...
Honolulu Beachfront Retreat by Gather: Lux Beachfront w/ Ocean Views & Comfort
This property is offered as a monthly rental. Although full-month occupancy is not required, the monthly rate remains fixed and applies in full, regardless of the number of nights stayed, as prorated rates are not available.Welcome to Honolulu Beachfront Retreat by...
Lagoon View Resort Retreat
Keep it simple at this peaceful at this Resort Hotel Room. A lovely view from private lanai overlooking lagoon and mountains beyond at this popular kauai's East side Oceanfront Resort location. An easy 5 minute drive from the LIhue airport, an ideal resting spot to end...
Escape to Paradise at Lagoon Tower by Hilton Grand Vacations – Studio Retreat!
Experience the vibrant energy of Waikiki from the heart of the Hilton Hawaiian Village® Waikiki Beach Resort, where the Lagoon Tower Studio combines modern comfort with a prime tropical location. Perfect for couples or small families, this cozy retreat offers an ideal...
Beachfront Retreat: Elegant Views w/ Full Kitchen. Onsite Parking and Pool!
Step into your spacious and beautifully designed suite, where modern comfort meets tropical charm. Each unit features a fully equipped gourmet kitchen, furnished lanai, in-room washer and dryer, and luxurious bedrooms and living areas.Why Stay Here?Whether you’re...
Sunset Shores - Waialua Oceanfront Retreat - 30 Day Rental
**This property may not be rented for less than 30 consecutive days. Rental prices will not be reduced or adjusted based on the number of days the rental is actually used or occupied**Welcome to Sunset Shores! Located in Waialua on the North Shore of Oahu, this...
Experience the perfect blend of comfort and stunning ocean views—your ideal island retreat awaits!
Enjoy breathtaking views of the Ala Wai Yacht Harbor and the Pacific Ocean from this modern and stylish 22nd-floor studio! Thoughtfully designed for comfort and convenience, this spacious condo features a comfortable Queen bed, dining table, and cozy lounge chair.The...
KaMilo #503 by Gather: Luxury Mauna Lani Retreat Near Golf & Beach
Nestled in KaMilo at Mauna Lani Resort, this three-bedroom, three-bathroom villa offers elegant island living with resort-style amenities. The open-concept design features vaulted ceilings, Cumaru wood flooring, and a gourmet kitchen with high-end appliances and a...
Beachfront Retreat | Room w/ Lanai | Pool Access
Discover Waikiki’s charms from our doorstep—steps to Kuhio Beach and Diamond Head. Explore local cuisine, shopping, and vibrant nightlife all within reach.Wake up to mesmerizing ocean views and let the day unfold with vibrant Hawaiian adventures at our beachfront...
Family-Sized 5BR Retreat with Easy Beach Access
PERFECT FOR:Families | Large Groups | Remote workers | Pet owners | Beach lovers | Golf enthusiastsGreat Location:- Minutes to pristine Ewa Beach for surfing & swimming- Close to championship golf courses- Easy access to local dining & shopping- Peaceful residential...
Tropical Retreat: Cozy Getaway Steps from Waikiki’s Best! Kitchenette, Pool
Make this comfortable and convenient property your next Waikiki adventure! Relax by the pool, enjoy dinner with family at one of three on-site restaurants, or grab a pastry and morning coffee at the coffeehouse. And best yet, the sun, sand, and surf of Waikiki Beach are...
Pohinahina Hale – 5BR Retreat at Hualalai Resort
Located just 6 minutes to the heart of the resort, Pohinahina Hale offers a spacious and secluded retreat for up to 10 guests. Two primary suites and two bedrooms are located in the main home, plus another bedroom located in a separate ohana (guest house). This home...
Secluded off-grid Retreat in enchanting Kurtistown with WiFi
Escape to a peaceful, off-grid getaway at the end of a scenic two-mile dirt road. This cozy one-bedroom rental is designed for comfort and simplicity, featuring a screened-in living room and fully equipped screened-in kitchen — perfect for enjoying fresh air and...
Kealoha Tropical Beach Villa: North Shore Surf Spot Retreat w/ Hot Tub & Views
This property is offered as a monthly rental. Although full-month occupancy is not required, the monthly rate remains fixed and applies in full, regardless of the number of nights stayed, as prorated rates are not available.Aloha and welcome to Kealoha Tropical Beach...
Luxury Vacation Retreat at Mauna Lani Point
Luxury Vacation Retreat at Mauna Lani Point – Unit J107Escape to paradise in this beautifully appointed 2-bedroom, 2.5-bathroom end-unit condo, nestled in the prestigious Mauna Lani Point community. Offering stunning views of Mauna Kea, lush tropical landscapes, with...
Charming 2BR Retreat in Wahiawa Close to Botanical Gardens and Surf
Your perfect home base for exploring beautiful Oahu!PERFECT FOR:Couples | Families | Surf lovers | Hikers | Pet owners | Digital nomadsAmazing Location:- Close to North Shore – Haleiwa, Pipeline, Sunset Beach- 5 minutes to Dole Plantation- Easy walk to local cafés &...
Stunning Oceanfront 1BR/2BA Retreat with Spectacular Views - Wailea Elua 1802n
Wailea Elua #1802 – Luxurious Oceanfront Retreat with Panoramic ViewsExperience upscale coastal living at Wailea Elua #1802, a beautifully renovated second-floor, 1-bedroom, 2-bathroom oceanfront condo located in one of Wailea’s most desirable beachfront...
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...
Hale Malu - a peaceful refuge above Hilo, A peaceful retreat above Hilo
Welina mai to Hale Malu, a light-filled home of peaceful refuge, with three bedrooms and two baths, wood-burning fireplace (wood provided), spacious fully-stocked kitchen with modern amenities, free WiFi, and free off-street parking. Enjoy the views of Mauna Kea and the...
Kahala Oasis: 6BR Retreat with Pool, Spa & Near Beach
This property is offered as a monthly rental. Although full-month occupancy is not required, the monthly rate remains fixed and applies in full, regardless of the number of nights stayed, as prorated rates are not available.Welcome to Kahala Oasis by Gather, an...
Ko Olina Kai 1027A: 2BR Retreat, Open Plan Living, Easy Access to Golf & Spa
This property is offered as a monthly rental. Although full-month occupancy is not required, the monthly rate remains fixed and applies in full, regardless of the number of nights stayed, as prorated rates are not available.Embark on an exquisite Hawaii getaway at Ko...
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,...
Renovated, peaceful retreat steps to Keaka Beach
Welcome to Koa Resort 1B, a beautifully renovated 1-bedroom, 1-bathroom ground-floor condo located in the heart of sunny Kihei, Hawaii. There is 1 portable A/C in the bedroom for your comfort. This charming unit is perfect for up to 4 guests, offering a delightful blend...
Step Out into Waikiki: Homely Hotel Perfect for Family Retreat | Outdoor Pool
Unwind in a spacious suite with private lanai, deep soaking tub, free WiFi, and plush bedding. Enjoy continental breakfast with Kona coffee, then stroll to Waikiki Beach or nearby shops. After exploring, relax by koi ponds or dip in the pool. Perfect for couples,...
Tropical elegance meets everyday comfort in this peaceful Princeville retreat.
A serene North Shore escape made for connection, calm, and a splash of island magic. Hale Hóomaka is a thoughtfully designed 2BR/2BA ground-floor condo tucked into the lush Princeville community, perfect for couples seeking romance or small families chasing sun-soaked...
Breathtaking Ocean Views! Peaceful Retreat/No Resort Fees. n
Amazing ocean, marina and mountain views.. Enjoy the relaxing and peaceful resort lifestyle, in this one of a kind recently remodeled unit. Designer decorated, new flooring, upgraded appliances, kitchen and bathroom. Resort like amenities include fitness center,...
Luxury Family Retreat: Spacious Hawaii Vacation Rental with Premium Amenities
Summary:Discover the ultimate family retreat in Kailua-Kona! This exquisite 5-bedroom house boasts a private pool, sauna, and stunning ocean views. Enjoy luxurious amenities, from the chef's kitchen to the kids' play area, and create lasting memories. Ideally located...
Couples Retreat: Romantic Room with Seafront Sunrise
Discover Waikiki’s charms from our doorstep—steps to Kuhio Beach and Diamond Head. Explore local cuisine, shopping, and vibrant nightlife all within reach.Wake up to mesmerizing ocean views and let the day unfold with vibrant Hawaiian adventures at our beachfront...
Oceanfront Kona By the Sea 2-Bedroom Retreat with Central A/C
45-Night Minimum • Central A/C • Heated Salt-Water Pool & SpaSavor jaw-dropping, third-floor ocean vistas and nightly Kona sunsets from the private lanai, living room, and even the kitchen of this spacious 2-bedroom, 2-bath suite at coveted Kona By the Sea.Inside...
Ko Olina Kai 1081C: 3BR Tropical Retreat, Steps from Golf and Dining
This property is offered as a monthly rental. Although full-month occupancy is not required, the monthly rate remains fixed and applies in full, regardless of the number of nights stayed, as prorated rates are not available.Discover the epitome of island elegance at Ko...
Nohie Lanikai by Gather: 4BR Beachside Retreat w/ Lanai & Private Yard
This property is offered as a monthly rental. Although full-month occupancy is not required, the monthly rate remains fixed and applies in full, regardless of the number of nights stayed, as prorated rates are not available.Welcome to Nohie Lanikai by Gather – A...
Oceanfront Retreat! Near Waihee Coastal Dunes and Wetlands Preserve, Pool
Our spacious suites with private lanais offer breathtaking views of the pristine shoreline, courtyard, or garden, providing the perfect backdrop for relaxation and adventure. Stay connected with high-speed internet, unwind in our unique whale-shaped outdoor swimming...
Tranquil Panoramic Retreat: Embrace Romance in Peaceful Serenity
This cottage is solely for couples who are in need of relaxation and peace. It is a cozy two-bedroom one-bath cottage, conveniently located on the ground floor for easy accessibility to our BBQ area along with a lanai capturing breathtaking sunsets of our West-Central...
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...
Mountain View Retreat Unit 2 - highly rated on leading vacation rental sites!
Peaceful rain forest guest house a few miles from Volcano National Park. Mountain View Retreat is located in a lush and relaxing paradise. Enjoy your coffee or tea in the morning on your own private lanai. For larger parties there is another guest house on the same...
Quiet & Private Retreat w/Outdoor Soaking Tubnn
The Wooden Gem is a magical tiny hut custom-built by fine furniture makers (that's us) using local woods. A true work of art, it's nestled in the native forest of Kaloko Mauka. At a cool 2200 ft elevation, we're just 10 minutes from town, airport, and beaches, but it...
Comfortable 3BR Retreat Near Ewa Beach with Modern Features
PERFECT FOR:Families | Beach lovers | Golfers | Remote workers | Groups | Relaxation seekersPrime Location:- 2 min walk to Ewa Beach Park- 5 mins to West Loch Golf Course- Close to Ka Makana Ali'i shopping- 20 mins to Ko Olina LagoonsEASY ACCESS:- 30 mins to Honolulu...
Westin Nanea 2-Bedroom Resort View: Maui's Ultimate Family Retreat Awaits You!
Spread out with the whole family in this spacious two-bedroom suite.The Westin Nanea Ocean Villas is more than a resort; it’s an invitation to immerse yourself in the spirit of Maui. Nestled on the pristine sands of Ka’anapali Beach, this luxurious resort blends...
Royal Mauian 205 - Splendid Oceanview Retreat, Stroll to Dining and Shopping!
Highly cleaned and sanitized for your vacation. Ask about our AlohaSafeStay program. If you have a stay that qualifies for housekeeping services, traditional housekeeping service will be performed every 7th day. This includes refreshing the condo and exchanging bed...
Breathtaking Ocean Views + Luxury Amenities + Gorgeous Beachfront Retreat
The Space:Notice - This home is in the HOTEL ZONE, so it will NOT be banned by the new law that will restrict short term rentals in the Apartment Zone.Welcome to our oceanfront home in Kahana!Our home is conveniently located at the prime location in the heart of West...