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.
Oceanfront Kahana Retreat: 1BR End Unit with Stunning Views & Whale Watching
Welcome to your tropical paradise retreat in Kahana! Experience the epitome of oceanfront living with breathtaking full ocean views from this exclusive end unit. Nestled in a serene and private setting, this 1-bedroom, 1-bath vacation rental offers a unique blend of...
Waterfront retreat with gourmet kitchen, spacious lanai & W/D
Wena ʻula EscapeOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'When you picture paradise, it looks exactly like this. Sitting directly by the water, this palm-lined home is the...
Maui Vista 3201: Your ideal retreat! Steps from beaches, dining, and The Cove!
Remodeled in 2024! Maui Vista 3201 is one of the best locations in Kihei! This 1 bedroom, 1 bath condo is the perfect retreat for your Maui getaway with beaches, dining, shopping, and golf all within minutes. It's just a block away from a favorite local surf spot, The...
Holua Kai #20: Tropical Ocean View Retreat at Holua Kai w/ Private Pool/Spa & AC
Holua Kai #20 welcomes you to a refined coastal retreat along the Kona Country Club’s Makai Golf Course, where sweeping ocean vistas meet the comfort of a gated, pedestrian-friendly community. Designed for both relaxation and connection, this two-story home blends...
Refreshed Tropical Private Ocean View Retreat On South Shore
Experience the best of Poipu from this stunning oceanview condo on Kauai’s sunny south shore! Located in the heart of Poipu, this spacious, resort-style home offers everything you need for the ultimate Garden Isle vacation. Just a short walk to world-class beaches,...
The Hula's Retreat - Well Equipped at Waikiki Grand
☀ Legally permitted vacation rental ☀ — Waikiki Grand Hotel® —134 Kapahulu Ave, Suite 217Workstation & fully equipped kitchenette.Fully equipped comfort greets you when you open our door to Waikiki Grand Hotel® suite 217.Whether visiting for 2 days or 2 weeks,...
Coconut Plantation 1080-1: Spacious 3BR Ko Olina Retreat w/ Wrap-Around Lanais
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 Coconut Plantation 1080-1 by...
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...
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...
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...
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...
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....
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...
Cute and Cozy Couples Retreat w/ Private Lanai, Mountain and Ocean Views, A/C
Sealodge B4 is an unpretentious, laidback getaway in the heart of Princeville, perfect for couples looking to enjoy a tropical vacation without breaking the bank. Enjoy the king bed, open concept living, dining, and kitchen areas, and take in amazing views from either...
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!...
Enjoy Luxe Hawaiian Retreat: Majestic Ocean, Elite Golf & Vibrant Vibes!
Escape to a sanctuary of peace and natural splendor, distinctively different from Waikiki's hustle, in this Ko Olina retreat. Just minutes from the enchanting beaches and elite golf courses of Ko Olina Resort, this inviting 3-bedroom, 2.5-bath vacation home is a beacon...
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...
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...
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...
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....
KPL 20 Experience ocean views, Cozy 2-bedroom retreat in West Maui.
Kaanapali Plantation 20 NEW LISTING! Sweeping Ocean Views and Sunsets from the North Kaanapali Hillside West Maui, 1 Minute from the Beach!Welcome to your Maui Retreat: Perched above the Kaanapali coastline on West Maui, this vacation home offers sweeping ocean views...
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...
Laule'a Ohana Retreat by Gather – 2 Mauna Lani Villas w/ Golf Views, Dual Pools/
Welcome to Laule'a Ohana Retreat, two side-by-side luxury villas on Hawaii’s Kohala Coast that together create the ultimate gathering place. With 8 bedrooms, 8 full baths, and 2 half baths across nearly 6,000 square feet, these residences are ideal for multi-family...
Poipu Retreat: 3BR with Ocean & Golf Views, Lanai Sunsets, Pool & Central A/C
Welcome to Pili Mai 8C – Your Private Poipu Retreat.Perched on the edge of the scenic Kiahuna Golf Course, Pili Mai 8C is a three-bedroom, three-bath condo that captures the very best of Kaua‘i living. With sweeping views of the ocean, golf greens, and surrounding...
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,...
Oceanfront Retreat at the Ilikai! Your island escape await!
*Brand New to our Inventory* Welcome to your beautifully renovated island escape at the iconic Ilikai Hotel, where sweeping views of the lagoon and Pacific Ocean greet you from your private lanai. Enjoy front-row seats to the Friday night fireworks show and take in the...
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....
Manoa Royal Retreat by Gather | Luxury 9-Acre Estate w/ Pool, Views & Trails
Manoa Royal Retreat is a rare 9-acre Honolulu estate where contemporary design meets lush Hawaiian mountain serenity. This three-story sanctuary sits high above the city with unobstructed views of the ocean, coastline, mountains, and sunsets. Designed by award-winning...
Oceanfront 2BR/2BA | Pacific Breeze Retreat at Kaha Lani 212
🌺 Pacific Breeze Retreat at Kaha Lani 212 - NEW TO OUR MANAGEMENTWake up to breathtaking sunrises and the sound of waves at Pacific Breeze Retreat, a two-story oceanfront condo on Kaua'i's Royal Coconut Coast. With no neighbors above, vaulted ceilings, and updated...
Golf Course View Retreat | Wailea Condo GC100 | Walk to Shops & Beaches
New Listing! *Intro Specials: Reduced rates and discounts for stays 7 nights or more. Excludes Dec 20-Jan 5*Welcome to Grand Champions #100, a meticulously updated 2-bedroom, 2-bathroom villa located in the heart of Wailea. Overlooking the 3rd hole of the Wailea Blue...
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...
Spacious Island Retreat • AC • WD • Parking • WiFi
Welcome to your large island getaway in sunny Kapolei! This 7-bedroom, 5-bathroom home offers two complete living levels, ocean views from the upstairs lanai, and all the amenities you need for a comfortable extended stay. With 2 kitchens, and plenty of indoor and...
Luxury Oceanfront 3-bedroom Retreat with AC in the heart of Kihei
Nestled in Kihei, this delightful condo boasts 3 bedrooms including 2 king beds, 1 queen bed, and 1 bunk bed. With 3 bathrooms featuring a bathtub, shower, and jetted bathtub, guests will feel right at home. The additional living room space with 1 queen bed and 1 full...
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, your serene...
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...
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...
O-523 Sunset Hale Retreat - Ko Olina Beach Villa. Steps to the Pool and Beach!
Welcome to our Sunset Hale Retreat - Ko'olina Beach Villa. Steps to the pool and beach!Amazing beachfront condo in the Ko'Olina resort overlooking swimming pool with beautiful pool and sunset views! Pristine residence features spacious living area and lanai with pocket...
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!
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...
Kaia Villa, at Turtle Bay - Modern North Shore Oahu Retreat w/Lanai & Golf Views
Special Launch offer-First 3 guest receive 20% off their stayDebuting October 2025. Kaia Villa offers a newly renovated stay on Oahu's famous North Shore. Set within Turtle Bay Resort , This property has been thoughtfully transformed into a stylish island retreat...
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...