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.
Welcome to your Waimanalo retreat!
Steps from one of Oahu's most stunning, uncrowded beaches. This charming 2-bedroom home blends classic island character with thoughtful modern updates. Fully furnished and move-in ready, it includes high-speed WiFi, a Bluetooth speaker, coffee maker, new cookware, and...
Family Retreat Near Akaka Falls – Sleeps 7 & BBQ
Escape to a lush tropical haven on Hawaii’s Big Island, where your coastal retreat is surrounded by nature’s best. Nestled just minutes from the stunning Hakalau Coast and the Botanical World Adventures. Surrounded by vibrant gardens, cascading waterfalls, and scenic...
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...
2 Homes in the Majestic Ilikai Hotel, Sleeps 10!
This listing is a combination of 2 separate units close to one another.Welcome to your ideal Hawaiian escape! Whether you're traveling solo, as a couple, or with family and friends, this special listing features two distinct condo units at the iconic Ilikai Hotel in...
Breathtaking Ocean Views + Luxury Amenities + Gorgeous Beachfront Retreat
The Space:Surf Shack Properties welcomes you to your Luxe Oceanfront Retreat! 1 Bedroom/ 1 Bath Condo at the Valley Isle Resort 2nd Floor with AC, Luxurious Amenities, and Ocean Views in Kahana, West Maui!✔ Oceanfront✔ Air Conditioning (A/C)✔ Luxurious Amenities:...
Tantalus Glass House by Gather Modern Honolulu Retreat
Welcome to Tantalus Glass House by Gather, an architectural masterpiece perched high above Honolulu. This five-bedroom, five-and-a-half-bathroom estate combines modern design with lush tropical surroundings, offering a rare blend of privacy, sophistication, and...
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.✦ Cleaning services...
Hilton Garden Retreat: 5-minute Walk to the Beach, Stunning City Views!
Prime Waikīkī Beach location with easy access to shopping, dining and attractions. Relax in contemporary rooms featuring island charm, plus enjoy a rooftop pool and 24-hour fitness center.This listing is for a room within a hotel.✦ Your room is 280 sq. ft, equipped with...
Charming Sea Village 3304: 1-bedroom ocean-view retreat in Kailua-Kona.
Welcome to Sea Village 3304 – Your Oceanfront Oasis on the Kona Coast!Experience the ultimate Hawaiian escape at Sea Village 3304, a beautifully appointed oceanfront property offering stunning views and unparalleled relaxation. This 1-bedroom, 1-bathroom condo is...
Welcoming bungalow with WiFi in Hawaiian Paradise Park
Hale Holo Homestead – Tropical 4BR/3BA Retreat in Hawaiian Paradise ParkSleeps 8 | 4 Bedrooms | 3 Bathrooms | High-Speed Wi-Fi | Private Entrances | Surrounded by Nature. There is also a pull out couch that sleeps 2 adults in the living room.Escape to Hale Holo...
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...
Whale Watching from Artist Inspired Retreat 2 Oceanfront Lanais AC
The Space:Surf Shack Properties welcomes you to your Oceanfront Vacation! Kahana Sunset A9 is Directly Oceanfront. 2-Level Condo with 2 Bedroom/ 2.5 Bath (Sleeps 6) at the Kahana Sunset Resort with two oceanfront lanai in Kahana, West Maui!✔ Oceanfront Views of Lānaʻi,...
Honolulu Beachfront Retreat: Lux Beachfront with Ocean Views
Welcome to Honolulu Beachfront Retreat, a stunning 4-bedroom, 3.5-bath coastal sanctuary set along a “secret” sandy stretch of East Honolulu. Spanning approximately 1,840 sq ft of refined living space and fronting 65 linear feet of pristine shoreline, this newly...
Couple Retreat | Room w/ Relaxing Waikiki View & Free Daily Hot Breakfast
Discover the heart of Waikiki – pristine beaches and electric nights await, all within a short walk to the ocean’s embrace and premier venues.This listing is for a room within a hotel.✦ Your room is 220 sq. ft, equipped with complimentary toiletries, high definition...
Tranquil Retreat in South Kihei: Maui Kamaole A-106 – Your Dream Island Escape!
Maui Kamaole, #A-106 – Ground-Floor Comfort Near the BeachMaui Kamaole #A-106 is a beautifully remodeled 1-bedroom, 2-bathroom ground-floor condo offering easy access, peaceful garden surroundings, and modern comfort just a short stroll from Kamaole Beach Park III....
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...
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...
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...
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...
Kahala Oasis: 6BR Retreat with Pool, Spa & Near Beach
Set along prestigious Kahala Avenue on O‘ahu’s sunny south shore, Kahala Oasis by Gather is a grand 6-bedroom, 6.5-bath luxury estate offering timeless elegance and island tranquility. Spanning 5,500 square feet of living space, this expansive retreat accommodates up to...
Pool House Studio with King Bed – Poolside Retreat
Stay poolside in this spacious 484 sq. ft. studio featuring a king bed, a sofa bed, and a convenient wet bar. With modern amenities like air conditioning, free Wi-Fi, and a flat-screen TV, this studio is perfect for a laid-back and refreshing escape.Key Features: •...
Kealoha Tropical Beach Villa: North Shore Surf Spot Retreat w/ Hot Tub & Views
Welcome to Kealoha Tropical Beach Villa by Gather, a luxury retreat along Oahu’s legendary North Shore. This stunning two-level teak home offers island elegance across from Alligator Rock and Leftovers Beach—two of the area’s most iconic surf breaks. With 3 bedrooms, a...
Partial Ocean-City Luxury Retreat at Sky Ala Moana w/Great Amenities
This property requires a minimum 30-day rental. Book with confidence—professionally managed by Ali'i Beach Rentals, an award-winning property management company.The Sky Ala Moana is Honolulu's newest symbol of luxury, featuring two distinct towers: The Residence and The...
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...
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...
Tucked in one of the most prestigious valleys, this 2/1 fully furnished could be a nice weekend getaway. Enjoy the nice cool breeze in a quiet setting. The unit includes coffee maker, microwave, toaster.
Stunning Oceanfront 1BR/2BA Retreat with Spectacular Views - Wailea Elua 1802
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 communities....
Turtle House by AvantStay | Oceanfront Group Retreat w/ Patio + Views
Please note this property is only available for stays of 30 nights or longer.Welcome to Turtle House, your luxurious oceanfront escape on the stunning island of Oahu! Step into your outdoor paradise with sprawling lawns, a spacious patio, and a deck offering mesmerizing...
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...
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...
Cozy Yurt retreat on a Coffee Farm in Holualoa. 8 mn from the Beach & shopping
Located at 1200 ft elevation. Does not require AC nor heat as it always has the perfect temperature. Experience living in yurt nestled among the coffee trees. You can enjoy your coffee out on the deck while listening to the birds or watching the magnificent...
Quiet & Private Retreat w/Outdoor Soaking Tub
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...
Ko Olina Kai 1081C: 3BR Tropical Retreat, Steps from Golf and Dining
Tucked within the Ko Olina Resort, Ko Olina Kai 1081C by Gather is a cheerful two-story villa where bamboo floors, high ceilings, and breezy indoor-outdoor flow set the tone for easy island days. With three bedrooms, three full bathrooms, and 1,625 sq. ft. of interior...
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...
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...
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...
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 most...
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...
Discover serenity at our home. 3 beds, 2 baths, steps from world class Makaha beaches. Enjoy a spacious retreat with a fully equipped kitchen, outdoor BBQ, and scenic views. Nearby hiking, golf, and local attractions. Safe and convenient. Your Hawaiian escape awaits!
Kihei Bay Vista C-202: 1 Br located across from Kalepoleopo Beach Park
One-bedroom Garden view condo. This unit sleeps up to four people with a queen bed in the living room and a comfortable pull out sofa sleeper equipped with a new sleeping unit. The living room boasts new upgrades including a built-in shelving unit with a new 42in LCD...
Lanikai Hideaway: 4 BR Luxury Retreat near Lanikai Beach
Tucked into the sought-after Lanikai neighborhood of Kailua, Lanikai Hideaway is a 4-bedroom, 3-bath luxury retreat designed for those who want space, privacy, and a true island connection. Just a 10-minute walk from the world-famous sands of Lanikai Beach, this...
Ground Floor Retreat W/Kitchen - Kaha Lani 115
Castle Kaha Lani Resort #115 on the ground floor: Enjoy Ocean views on this ground-level one-bedroom/one-bathroom condo with a breezy interior, sliding-glass doors, and an open concept floor plan. Tropical patterns and calm earth tones create a soothing island...
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...
*NEW* Kea’au Big Island Studio Retreat
Located on the eastern side of the Big Island, this modern 1-bathroom Keaau vacation rental puts right in the heart of the area's top outdoor destinations. Explore scenic hikes in Hawai’i Volcanoes National Park, enjoy the tropical landscape in the mists of Akaka Falls,...
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...
Sea Cliff Chic – Ultra-Luxury Oceanfront Retreat in Portlock
Sea Cliff Chic is the newest residence in the collection of ultra-luxury homes designed by renowned Hawaii Architect Jim McPeak and built by San Diego-based developer Mark Gosselin. This Oahu vacation home is a modern take on Oahu’s well-known Honeyed Jade. This...
Peaceful Mountain Retreat- Jungle Mountain Vibes
This cute studio cottage is nestled on the mountainside just above Kona, in a cute little art town called Holualoa. Escape the hustle of Kona and retreat in nature with mature fruit trees, fresh eggs from our hens, and lush foliage. This is a true local experience for...
Aloha casa kona heavenly retreat
Best house for a lovely vacation in kona.Situated above the highway on a cool elevation with a cool breeze coming in from the ocean.This peppery is perfect for a family or travel companions. It features 3 bedrooms and 3 bathrooms.
Quiet 1-bd cottage retreat with sleeping loft & work space
Quiet, secluded cottage with 2 private decks. Equipped with everything you need for a weekend escape or longer retreat. The cottage has outdoor & indoor dining areas, a king bedroom, sleeping loft, and a separate work / yoga area. Washer & dryer on-site.
Fun Family Private Retreat with lighted Sports Court and Pool
More than just a stay, it's an experience for the whole family, both young and old. Our family retreat has over 3000sq' under roof, overlooking incredible ocean and coastline views. Sitting on 6 private acres of old lava fields with a beautiful pool, lighted...