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.
Exceptional Ground Level Retreat: Kihei Surfside #102 – Stunning Pacific Views!
Kihei Surfside #102 – Stylish Ground-Floor Ocean View Condo with Recent UpgradesDiscover the best of coastal living at Kihei Surfside #102, a beautifully updated ground-floor condo offering ocean views and easy beach access. This 1-bedroom, 1.5-bathroom unit sleeps up...
Private Island Retreat At The Cliffs Princeville!
Experience panoramic views of the Pacific Ocean and iconic Mt. Makana ("Bali Hai") from this private and spacious condo at The Cliffs in Princeville. Perched on a scenic bluff with distant ocean vistas and lush tropical surroundings, this beautifully appointed retreat...
Oceanfront Bliss – A Relaxing Retreat with Breathtaking Views
Whether you’re here to soak up the incredible sunsets, spot sea turtles from the lanai, or witness majestic whales (in season),this serene escape is ready to make your island dreams come true. Step inside this fully updated condo and experience modern comfort paired...
Tranquil Hawaiian ocean view retreat
Kaanapali Shores 616 is a 2-bedroom, 2-bathroom condo with central air conditioning that can accommodate up to 6 guests. Located on the sixth floor, inside you will find an open-concept layout and Hawaiian-inspired decor with a sense of island serenity. When it's time...
Kona Pacific C416 by Gather: 1BR Condo Retreat w/ Pool & Ocean Views
Welcome to Kona Pacific C416Escape to tranquility at Kona Pacific C416, a beautifully appointed 1-bedroom, 2-bathroom condominium in the heart of Kailua-Kona. This ocean-view retreat comfortably accommodates up to four guests, making it perfect for couples, families, or...
North Shore Oceanfront Private Retreat with Pool!
Absolutely the best location on the north shore of Kauai! This beautifully furnished, spacious, and private home is situated in the heart of Princeville minutes away from all of the world-class beaches, mountain forest trails, outdoor activities, golf courses, and...
Townhouse Retreat with Ocean Views From Upper & Lower Lanai - Wailea Ekahi #30Bn
Wailea Ekahi Village #30B Discover the perfect blend of luxury, comfort, and location at Wailea Ekahi Village #30B. This spacious two-story townhouse offers stunning ocean views from both floors, a fully remodeled kitchen and bathrooms (March 2025), and unbeatable...
Volcano Rainforest Retreat with a Hot Tub
As you pull up to this grand cedar style home you are immediately greeted by a beautiful rainforest that feels calming and relaxing. The first room is located to the far right corner of the building. There are a few stairs leading to a small covered patio for you and...
Bright, island retreat with ocean views, pool, & patio
Mahina Surf 104Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Oceanfront and filled with island vibes, this efficient condo has everything needed to make unforgettable memories and...
Stunning Waikiki Beach Retreat - 2 mins from Ocean
Legally permitted rental - TRADEWINDS PLAZA2572 Lemon Rd #305** For your health and safety, we utilize additional Sterilization procedures between reservations.Gorgeous Queen 1 bedroom spacious apartmentAll the appliances / furniture are brand new in this gorgeous...
Kuilima Golf Retreat
Welcome to your perfect getaway at the Kuilima Golf Retreat! This beautiful rental offers exceptional amenities and is just a short walk from the beach.This inviting unit accommodates up to four guests, featuring one bedroom, a comfortable sofa bed, and one bathroom....
Royal Kahili retreat with pool, hot tub, lanai, & elevator - near beach
Royal Kahili B202Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Set in the Royal Kahili complex, this condo is just half a mile from a beautiful beach. Across the street, you’ll...
Spacious retreat home with private pool & screened lanais - conveniently located
He'eia Haven Retreat - Units A & BOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Experience the best of Kailua-Kona with a stay at this spacious Hawaiian-style beach retreat home!...
Premium Beach Retreat Waiohai Club Resort + Resort Amenities Included.
Nestled on the golden crescent of Poipu Beach, hailed as one of America's finest shores, our resort offers you a front-row seat to paradise. Imagine waking up to the gentle symphony of waves crashing and feeling the warm sand between your toes as you step onto the...
Designer Oceanview Retreat: Steps to Kamaole Beach
Summary:Discover your perfect tropical escape at the Designer Oceanview Retreat, where style meets serenity. Just steps from Kamaole Beach I, this stunning condo offers a modern haven with breathtaking ocean views. Feel the soothing island breeze on your face as you...
North Shore Oceanfront Retreat by Gather: 5BR Spacious Home Paradise
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 North Shore Beachfront Retreat by...
Spacious 4BR/2BA Retreat in Beautiful Wahiawa
ESCAPE TO PARADISE - SPACIOUS OAHU RETREATPERFECT FOR:Families | Remote workers | Beach lovers | GroupsCentral Location:- 5 mins to Wahiawa Botanical Garden- 10 mins to Dole Plantation- 30 mins to North Shore beachesSleeps 8 Guests:- 4 queen beds + AC all rooms,...
Luxurious five-bedroom modern retreat
This five-bedroom home inHonolulu offers a blend of modern design and tranquil vibes. The spacious interior features an open-concept living area .The kitchen is modern and functional, with sleek finishes and ample storage. The master suite provides a serene retreat....
Kalaekilohana Inn & Retreat - #1 Rated Hawaii Island Hotel - Dinner Nightly
Hawaii's #1 Small Hotel featuring complimentary locally sourced breakfasts daily and Chef Kenny's dinner nightly. Prices are per room per night. Looking for the perfect compliment to the luxury resorts in the north? You've found it. Enjoy luxurious rooms in an iconic...
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...
Hale Maia at Kukui ula - Elegant Pool Retreat with Golf Views in Poipu
Summary:TA-101-738-2400-01Discover Hale Maia at Kukuiʻula, a stylish and spacious 5BR, 5.5BA home in Kauai’s most exclusive community. This modern retreat features panoramic fairway views, a private heated pool, and seamless indoor-outdoor living. With each bedroom...
Tropical Retreat w/ Outdoor Pool, Free Parking, Steps from Papaloa Beach!
Step into a world of relaxation, surrounded by swaying palm trees and vibrant hibiscus blooms. Your spacious suite features a full kitchen, separate living room, and private lanai. Refresh yourself in our sparkling outdoor pools, perfect for relaxation or family fun....
Maui Kamaole #C-203 - Remodeled Upstairs Retreat with AC and Resort Pools!
Maui Kamaole #C-203Maui Kamaole #C-203 is a beautifully remodeled two-bedroom, two-bathroom upstairs unit offering a peaceful setting, modern comfort, and a fantastic location near some of South Kihei’s best beaches. This updated condo features island-inspired décor,...
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....
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...
The Palm Treehouse: Serene retreat with simultaneous mountain and ocean views
Experience the unparalleled majesty and tranquility of Kauai's North Shore! The Palm Treehouse (#30) at Hanalei Bay Villas is uniquely situated between the mountains and ocean, allowing you to admire both at the same time. Come get lost admiring the stunning landscape...
Leaf House: Lux Retreat w/ Pool, Ocean Views & Outdoor Living Near Lanikai
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 Leaf House by Gather, a luxurious...
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...
Puna Rainforest Retreat Hotspring - Blue Ginger Cottage
Puna Rainforest Retreat Blue Ginger Cottage has a complete kitchen with all the amenities, a full bathroom and cozy queen size bed. Perfect for couples. This colorful cottage is clean, comfortable and affordable! Enjoy the rainforest trail, steam vents, plunge pool,...
Tantalus Glass House by Gather Modern Honolulu Retreat
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.Perched high above Honolulu, Tantalus Glass...
Oceanfront Bliss at Hale Kona Kai 310 - A Cozy 1-Bedroom Retreat in Kailua Kona
Kona Town's historic “OCEAN VIEW MILE WALK”, with 24 Pacific Ocean view restaurants, multiple live entertainment venues, ocean front swimming beaches and charming shops, BEGINS AT YOUR FRONT DOOR.Enjoy ocean views, sounds and sweet fresh air breeze from your...
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: •...
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!
Serene Waikiki Studio Getaway - Peaceful Retreat Close to Beach and Hospitals
Welcome to the Serene Waikiki Studio Getaway, a thoughtfully designed, fully furnished studio in a quiet part of Waikiki near the Ala Wai Canal. This beautiful, newly renovated space is perfect for those seeking both tranquility and convenience, whether you’re here...
Moani Heights 9013 - Luxurious Island Retreat
Rest and recharge in this luxurious four-bedroom, four-bath island retreat, where indoor comfort meets stunning outdoor living. The open-concept kitchen and living area flow seamlessly onto a spacious, furnished lanai, perfect for enjoying the coastal breeze. Step...
Relaxing upcountry retreat on the slopes of Haleakalā. Ideal for families.
After a hot day at the beach, relax at Ke Kīhāpai Bed & Breakfast at the 2400 foot elevation with unobstructed views of our dormant volcano, Haleakalā. Breathe the fresh air with an upcountry view of town, the north shore of Maui and Kahālāwai (West Maui...
Puna Rainforest Retreat Hotspring - Purple Passion Cottage
The Purple Passion Cottage is located on a serene 20 acre estate with beautiful ocean and meadow views. The cottage is cozy and equipped kitchenette (range, oven, mini-fridge/freezer, microwave), full bathroom and two bedrooms. The main bedroom has a king bed with an...
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...
Hanalei Happiness - Brand NEW Modern Family Retreat w/Kids Loft, AC, Pool & More
NEW Modern Family Retreat | Limited Introductory RateThoughtfully created with traveling families in mind—packed with amenities and curated for comfort, all while capturing the vibrant spirit of Hanalei. - 8 Min to Hanalei- Super Convenient Location- Air Conditioning...
Whale Watching from Artist Inspired Retreat 2 Oceanfront Lanais AC
Just a short distance from the sea, this smoke-free apartment lets you experience it all. Keonenui Beach is just steps away and Ka'opala Beach is within an easy 6-minute walk, so leave your car at the property, which offers onsite parking. A BBQ grill and air...
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...
2BD/2BA! Charming Retreat: Ground Floor w/King, AC, Garden/Lanai
Aloha! Boutique, six-unit complex in quiet cul-de-sac less than 300 ft (100 yards) from the ocean! Three very comfortable real beds: king & two queens. Large, private patio/lanai/garden area & BBQ. Shared saltwater pool (often empty). Newer AC, ceiling fans and box fans...
Tranquil 2BR/1BA Retreat in a Serene Neighborhood
PERFECT FOR:Professionals | Remote workers | Small teams | Pet owners | Garden loversCentral Wahiawa Location:- Walk to Wahiawa Botanical Garden- 10 mins to local dining & unique shops- Easy access to island attractions & beaches- Peaceful residential neighborhood...
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 150 5 star reviews on another popular listing site under the same name,...
Lanikai Ola Nani: Majestic Retreat, Close to Bch, Designer Details, 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.Discover Lanikai Ola Nani, an exquisitely...
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...