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.
Kalani, Charming Hawaiian Retreat in the heart of Princeville
New! Welcome to Kalani Kauai, your beautifully remodeled island retreat in the heart of Princeville, Kaua‘i — where modern luxury meets timeless aloha charm.Nestled on Kaua‘i’s breathtaking North Shore, this stunning 3-bedroom + loft (loft sleeping area for teens and...
Lux Makakilo Hale by Gather: 5BR Retreat w/ Private Pool & Ocean Views
Perched high above Kapolei on O‘ahu’s sunny west side, Makakilo Hale by Gather offers a private hillside escape blending modern design, panoramic views, and relaxed island luxury. With 5 bedrooms, 2.5 baths, and a resort-style pool, this expansive retreat is perfect for...
Kukuiula Makai Cottage #12: Plantation-Style 2BR Retreat in Poipu
Kukuiula Makai Cottage #12 is a charming cottage nestled in the heart of Poipu’s highly sought-after Kukuiula neighborhood. This single-story plantation-style retreat blends vintage Hawaiian charm with upscale modern comforts. Featuring two bedroom suites, this cottage...
Winter Holiday Sale! 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...
Charming 2-bedroom cottage in enjoyable Ewa Beach with WiFi, AC
Wake up to the sound of waves at your own private oceanfront retreat in Ewa Beach. Tucked away on a quiet residential street, this air-conditioned home is ideal for couples, families, remote workers, and fishing lovers who want a peaceful stay right on the water—with...
Peaceful 2BR retreat with pools & hot tubs
Summary:Golf Discount in Village, Gorgeous Views, 2 PoolsThe Space:Welcome to your peaceful island escape overlooking the Waikoloa golf course, perfect for families or friends seeking comfort & scenic views:- Sleeps 4 | 2 bedrooms | 2 beds | 2 baths- Access to 2 pools,...
Modern Princeville Retreat – Hanalei Bay Rental with Private Pool
This beautiful brand new home is overlooking Hanalei Bay & the beautiful tree canopy of Princeville. With a 10 min walk to the 1 Hotel beach, a short walk to Princeville Center and a quick drive to Hanalei Town, it is the ideal central north shore location. Featuring...
Tropical Retreat w/ Outdoor Pool, Free Parking, Steps from Papaloa Beach!
Welcome to your ultimate tropical retreat! Walk to Waipouli Beach & Coconut Marketplace, with Opaekaa Falls just a drive away. Perfect for island exploration!This listing is for a room within a hotel.✦ Your room is 725 sq. ft, equipped with complimentary toiletries,...
Welcome to your Waimanalo retreat! Steps from one of Oahu's most stunning, uncrowded beaches
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...
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:Welcome to our 1 BR Oceanfront home in Kahana, conveniently located at the prime location in the heart of West Maui within walking distance to some of the island’s most popular spots, including local favorites. ✔ Oceanfront Home✔ Air Conditioning (A/C)✔...
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.PLEASE NOTE:This listing is specifically for a hotel room located within a hotel,...
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: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 pool✔ BBQ...
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...
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 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...
Cozy quiet retreat
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...
Serene Makaha Retreat
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!
Family Retreat In Beautiful and Lush North Shore
Welcome to Mauna Kai 2B, your home away from home, situated between mountains and ocean. The whole group will enjoy easy access to all North Shore attractions from this centrally located condo. Surrounded by lush tropical gardens and a residential feel, this is the...
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...