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.
Relaxing tropical retreat near Diamond Head. Unwind and rejuvenate your senses.
Experience a calming Oasis at the Kahala Beach Apartments. This peaceful retreat is a fully furnished 2 bedroom, 2 bath dwelling located on the 1st floor and has 1 parking stall included. Cool off comfortably with fully integrated air conditioning throughout the space...
Whale Watching from Artist Inspired Retreat 2 Oceanfront Lanais AC
The Space:Welcome to our spacious oceanfront home "Kahana Sunset A9" conveniently located at the prime location in the heart of West Maui!✔ Oceanfront Home with breathtaking oceanfront views of Lanai and Moloka’i✔ Air Conditioning (A/C)✔ A heated swimming...
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...
Tropical Retreat with Heated Pool in Ilikai Hotel
Our spacious apartment is designed to provide you with all the comforts of home, plus the added benefits of a resort-style setting. The unit features two beautifully appointed bedrooms. The master bedroom serves as a serene retreat with a plush king bed, offering a...
Luxury Oceanview Wailea Retreat with Sunset Views
Escape to Hōkū 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,...
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...
Kilipue Retreat by Gather | Luxe 3BR Home w/ Fenced Yard Near Ko Olina
Kilipue Retreat places you at the quiet end of a Kapolei cul-de-sac, minutes from beaches and big-city conveniences yet wrapped in the calm of a residential neighborhood. Newly refreshed and fully furnished, this 3-bedroom holiday home welcomes corporate guests,...
Romantic Retreat – Lahaina Shores 504, Sunrise Balcony
* NEW PROMO: Stay 5 or more nights from September 1st - October 31, get 1 FREE!Lahaina Shores 504 – West Maui Mountain ViewsLahaina Shores is a charming boutique resort located directly on the oceanfront in the heart of historic Lahaina Town. Unit 504 is a 5th-floor...
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...
Gated Tropical Hawaiian retreat, 5 minutes to Kailua Kona town and the Ocean.
The Kona Palm Retreat is a private gated estate located 8 minutes from kailua Kona town and the Pacific Ocean. This property is newly listed on VRBO, this property is a guest favorite and has over 200 5 star reviews on another popular listing site., The Kona Palm...
Lanikai Ola Nani: Majestic Retreat, Close to Beach, Designer Details, Views!
Lanikai Ola Nani by Gather is a refined island sanctuary just steps from the sands of world-famous Lanikai Beach. This four-bedroom, four-bathroom retreat combines designer renovations with indoor-outdoor flow, creating a private haven for monthly stays in Kailua’s...
Stunning Ground-Floor Retreat with Breathtaking Views! -Makena Surf #G-103:
Makena Surf G-103Welcome to Makena Surf G-103, a beautifully updated ground-floor oceanfront condo located in the prestigious Makena Surf Resort. With modern finishes, direct beach access, and elegant resort amenities, this two-bedroom, two-bathroom unit offers a...
Hale Kai'opua - Modern Kauai Retreat with Private Pool & Lanai
Welcome to Hale Kai‘opua at Kukui'ulaNestled in the picturesque town of Poipu in the exclusive Kukui'ula community, Hale Kai‘opua is a luxurious 3-bedroom, 3.5-bathroom retreat offering breathtaking ocean and golf course views. Built in 2024, this modern home blends...
Couples Retreat! Pacific Vista w/WiFi and A/C– Waikīkī Shore 504
Welcome to your beach retreat in Waikīkī! Relax in this Studio Ocean View condo, which offers fantastic lanai views of the Pacific Ocean, Waikīkī Beach, and the palm treetops of Fort DeRussy Park. The private lanai has seating for two people and has a small table so...
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...
Serenity Retreat- 3 bed / 2 ba
Welcome to our Serenity Retreat in the heart of Mililani, Hi. Our retreat is nestled in a peaceful neighborhood and offers a perfect blend of comfort and serenity, making it an ideal getaway for those seeking a rejuvenating escape.This particular unit is located on the...
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...
Honolulu Beachfront Retreat: Lux Beachfront with Ocean 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.Welcome to Honolulu Beachfront Retreat by...
Kailua Sands | Oceanfront Pool Retreat with Gym | Sleeps 7
Kailua Sands sits directly on the golden curve of Kailua Beach, where turquoise waters meet soft sand just steps from your lanai. This single-level, 3,360-square-foot home embraces a seamless indoor-outdoor flow, centered around a private pool courtyard framed 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...
Oasis Retreat: Beautiful 4BR 2BA
Welcome to our Serenity Retreat in the heart of Mililani, Hi. Our retreat is nestled in a peaceful neighborhood and offers a perfect blend of comfort and serenity, making it an ideal getaway for those seeking a rejuvenating escape.This particular unit is located at the...
Sunset Shores - Waialua Oceanfront Retreat - 30 Day Rental
**This property may not be rented for less than 90 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...
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
Aloha, and welcome to your tropical playground on Waikiki Beach!This listing is for a room within a hotel.✦ Your room is 1419 sq. ft, equipped with complimentary toiletries, high definition 55-inch TV, available with Standard cable, and Premium cable.✦ Daily...
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
PERFECT FOR:Surfers| Hikers | Couples | Families | Pet ownersSPACE HIGHLIGHTS:- 2BR with queen beds- Sleeps 4 - Full kitchen- Living area w/ fast WiFi- A/C throughout- In-unit washer & dryerUNBEATABLE LOCATION:- 25-30 mins drive to North Shore (Haleiwa, Pipeline, Sunset...
Hawaiian Retreat Near Waikiki Beach – Cozy & Peaceful Stay! | Onsite 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,...
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...
Kapalua Bay Villas – Spacious Double Retreat in Maui’s Premier Resort
This listing is a combination of 2 separate units close to one another.The ResidencesExperience the best of Maui with this unique two-villa combination in the prestigious Kapalua Resort. Perfect for families or couples traveling together, these villas offer 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
Embark on a serene island escape at Ko Olina Kai 1027A, a ground-floor, single-level condo in the tranquil Ko Olina Kai community within the renowned Ko Olina Resort. With its inviting garden views, spacious layout, and effortless access to resort amenities, this...
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,...
Private Oceanfront Ohana Retreat Near Hanalei!
Enjoy the very best of Kauai’s north shore from this beautifully remodeled cliffside getaway in the heart of Princeville! Perfectly situated just minutes from Hanalei Bay & some of the world's most iconic surf spots. Step outside to enjoy warm trade wind breezes,...
VI 507 Maui Studio Retreat – Enjoy Panoramic Lanai Views Near Beaches, Shopping & Restaurants
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...
Kaanapali Perfect Retreat - Lovely 2BR Golf Course Condo, Easy Walk to Beach
Enjoy your dream getaway in the best of paradise in Maui, Hawaii, with this exquisite 1534 sqft ground-floor condo offering the ultimate in comfort and luxury. Designed to accommodate up to 6 guests comfortably, this home boasts two well-appointed bedrooms, each with...
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 Retreat in Kona with Saltwater Pool
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...
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...
Panoramic Oceanfront Retreat in Lahaina Shores 509
* NEW PROMO: Stay 5 or more nights from September 1st - October 31, get 1 FREE!Lahaina Shores 509 – Pacific Ocean ViewsLahaina Shores is a charming boutique resort located directly on the oceanfront in the heart of historic Lahaina Town. Unit 509 is a 5th-floor...
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...
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...