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.
(P9B) 2Br Princeville Retreat, Pool, AC, Wifi
Two-Story Princeville Condo – Lanai, Pool & Near BeachesFeel the trade winds and unwind in this spacious two-story retreat in Princeville, where tropical breezes, lush surroundings, and island living come together in perfect harmony. This beautiful condo offers a...
Royal Kahana 1010 2BD Coastal-Luxe Oceanfront Retreat w/ Lanai, AC & Stunning Maui Views
Royal Kahana 1010 Enjoy Epic Sunsets from this Stunning 2 Bedroom West Maui Oceanfront Retreat Welcome to your Maui Retreat: Royal Kahana 1010 is a stunning tenth-floor corner residence where uninterrupted ocean views stretch from the golden coast of Ka'anapali to the...
Kahana Sunset B4B Oceanfront Retreat w/ Sunset Views, AC & Private Lanai
Kahana Sunset B4B Spectacular West Maui Sunset Views, Steps from the Pool and the BeachWelcome to your Maui Retreat: Welcome to Kahana Sunset B4B, a beautifully remodeled 1-bedroom, 1-bath hideaway nestled in the boutique beachfront enclave of Kahana Sunset along the...
Westin Kaʻanapali North 1BR Premium – Island Retreat
Discover your perfect Maui escape in this 1-Bedroom Premium Island View Villa at The Westin Kāʻanapali Ocean Resort Villas North. Offering approximately 750–900 square feet of space, this villa is ideal for couples or small families, with thoughtful details that make...
Spacious Ground Floor Maui Retreat, Grand Champion
Summary:🌴 Prime Location – 5-min stroll to Charley Young Beach🏊 Resort-Style Living – Pool, hot tub, BBQ & tennis courts🛏️ Ultimate Comfort – King bed + memory foam sofa bed🍹 Private Lanai – Sip cocktails with lush garden views🍽️ Chef’s Kitchen – Fully equipped for...
Oceanview Retreat – 2 Side-by-Side Condos!
Summary:🌴 Prime Location – 5-min stroll to Charley Young Beach🏊 Resort-Style Living – Pool, hot tub, BBQ & tennis courts🛏️ Ultimate Comfort – King bed + memory foam sofa bed🍹 Private Lanai – Sip cocktails with lush garden views🍽️ Chef’s Kitchen – Fully equipped for...
Perfect for Romantic Retreat! Spacious Oceanfront Suite w/ Pool Access
Step into paradise: Explore Kanaha Beach Park & indulge at Queen Kaahumanu Center, right from our welcoming Kahului Bay doorstep.This listing is for a room within a hotel.✦ Your room is 588 sq. ft, equipped with complimentary toiletries, high definition 32-inch TV,...
Luxe Maui Beach Retreat Walk to Kamaole Beach
Summary:Prime Location Steps to Kamaole Beach dining shops Luxury Comfort King bed memory foam sofa bed Resort Perks Pool hot tub outdoor grills Entertainment 65 Smart TV free Netflix fast WiFi Seamless Stay Self-check-in Smart Lock Exclusive Perks 1000 in local...
Beach Bliss Retreat | Walk to Surf & Dining
Summary:Steps to the Beach Charley Young Kamaole 1 nearby Prime Location Walk to top restaurants shops Fast WiFi Smart TV Spacious Stylish Modern decor cozy ambiance Luxury King Bed Guests rave about comfort Resort Perks Pool hot tub BBQ tennis courts Free Parking Fully...
Beachside Retreat | Walk to Shops & Dining
Summary:Walk to the beach shops top restaurants Stunning garden lanai perfect for coffee wine Ultra-comfy queen beds for a restful sleep Resort-style pool hot tub BBQ area Smart TV high-speed WiFi for entertainment Free parking for hassle-free stays Beach gear included...
Beach Retreat | Walk to Maui’s Best Shores
Summary:Prime Location 5-min stroll to Charley Young Beach Resort-Style Living Pool hot tub BBQ tennis courts Ultimate Comfort King bed memory foam sofa bed Private Lanai Sip cocktails with lush garden views Chefs Kitchen Fully equipped for home-cooked meals Stay Cool...
Oceanview Retreat Walk to Beach & Restaurants
Summary:Prime Location Walk to beach dining shopping Breathtaking Ocean Views Enjoy from private lanai Luxury Memory Foam Bed Sleep like royalty Fully Equipped Kitchen Cook with ease Resort Perks Pool hot tub BBQ grills Exclusive Coupons Save 1000 on Maui activities...
Steps to Beach Hot Tub Luxe Maui Retreat
Summary:2-Min Walk to Pristine Kamaole Beach Ultimate island escape Private Hot Tub Resort Pool Relax after sun-filled adventures Luxury Beds Linens Guests rave about restful sleep Fully-Equipped Kitchen Cook gourmet meals with ease Fast WiFi Dedicated Workspace Ideal...
Serene Maui Retreat Walk to Beach & Shops
Summary:Prime Location Walk to beach dining shops Tranquil Balcony Enjoy morning coffee w lush views Luxury Beds Linens Ultimate comfort for deep rest Resort-Style Amenities Pool hot tub tennis courts Free Parking 1 spot Secure hassle-free Fast Wi-Fi Smart TV Stay...
Family Retreat: 2BR Villa at Sheraton Kaua‘i Resort
Located on Kaua‘i’s sunny South Shore, the 2-Bedroom Villa at Sheraton Kaua‘i Resort is the perfect choice for families or groups seeking space, comfort, and direct access to Po‘ipū Beach. With approximately 1,100 square feet of living space, this villa comfortably...
Makaha Vista Retreat by Gather: Mountain View Home w/ Pool, Hot Tub & Views
Nestled in the serene, gated hills of Makaha Valley, this airy three-bedroom retreat blends minimalist island design with modern comfort. Just minutes from world-famous Makaha Beach, it’s a peaceful base for families, couples, or extended groups seeking space, light,...
Modern Coastal Retreat with Ocean Views and Beach Access – Puako Beach Drive #310
Welcome to your island getaway! This newly remodeled 3-bedroom, 2-bath Puako condo #310 blends modern comfort with timeless Hawaiian charm. Just steps from the ocean, this bright and airy retreat offers stunning views of swaying palms and the sparkling Pacific.The...
Luxurious retreat at KaMilo in the Mauna Lani Resort
Welcome to Moana Ohana, your luxurious retreat at KaMilo in the Mauna Lani Resort. This exquisite four-bedroom home is nestled within a premier gated community and offers over 2,400 square feet of living space, perfect for families or groups seeking a memorable Hawaiian...
Lahaina Shores 612 – Relaxing Oceanfront Retreat
Lahaina Shores 612 – Amazing West Maui Mountain Welcome to Lahaina Shores 612, a beautifully remodeled 6th-floor studio that captures the essence of island elegance. This stunning retreat accommodates two guests in comfort and style, featuring a plush platform...
Elegant Waikiki Retreat - Ocean View & Luxe Decor
Experience refined island living in this modern Waikiki condo with an ocean view. Designed for the discerning traveler, the space features SoHa Living décor, Nordstrom and Neiman Marcus-inspired furnishings, and Cozy Earth luxury linens. Enjoy a private lanai, stylish...
Tropical Haven Retreat in Ko Olina | TCP-1196-3
Welcome to your dream vacation home at Coconut Plantation - the most amazing destination in Ko Olina! Whether you're looking for a breathtaking sunset, a romantic getaway, a fun beach stroll, an exciting round of golf or a relaxing spa retreat, this resort has got you...
Ultimate Beach Retreat! 2BD Suite w/ Pool, Hot Tub
Come unwind at our spotless condo at the Maui Banyan Resort, just a few short steps from the soft, sandy beach. Enjoy peekaboo ocean views while you soak up the aloha spirit.✓ Right across the street from Kamaole Beach II✓ King bed + Queen bed + 1 pullout Queens✓ 2...
Private Home: Organic Farm Ocean & Sunset Views
Kona Farm Stay is perched above a working Kona coffee farm, this light-filled classic Hawaiian Hick's farm home invites you into the living, breathing rhythm of island life. From the moment you arrive, your senses are met with expansive ocean views, lush tropical flora,...
Quiet Retreat Between Fairways - Grand Champions 140
Wailea Grand Champions 140 is a remarkable vacation rental nestled in the upscale Wailea community of Maui. This charming property combines elegance with comfort, offering a luxurious retreat that is perfect for both relaxation and adventure. Upon entering Wailea Grand...
Family Retreat: 2BR Villa at Sheraton Kaua‘i Resort
Located on Kaua‘i’s sunny South Shore, the 2-Bedroom Villa at Sheraton Kaua‘i Resort is the perfect choice for families or groups seeking space, comfort, and direct access to Po‘ipū Beach. With approximately 1,100 square feet of living space, this villa comfortably...
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...
Island Charm Retreat at Inn on The Park | Walk to the Beach
*Important to note: if you're looking to book for longer than 30 days and the dates aren't showing as avaialble, please still reach out as the unit is likely available and we can assist in getting you booked for longer. Mahalo!*Incredibly located and uniquely designed,...
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...
Oceanfront Moloka‘i Retreat | Wavecrest 2nd Floor
Oceanfront Molokaʻi Stay | Pool, Tennis, ViewsPlease kindly note this property is located on Molokai island. This property is neither located on Maui nor accessible from Maui except by air travel.Discover the tranquility of Molokaʻi Island at this oceanfront getaway,...
Oceanview Penthouse Maui Retreat – Ideal for a Peaceful, Upscale Escape
Step into comfort, style, and panoramic beauty at this beautifully remodeled 1-bedroom penthouse condo at Island Surf that sleeps 4, perfectly suited for mature travelers seeking both relaxation and convenience. Whether you're enjoying morning coffee on the private...
Ocean & Waikiki Skyline Views – Modern 2BR/2BA Retreat, Resort Style Amenities
Wake up every day to sweeping views of the Pacific Ocean and Waikiki skyline from this stunning 2-bedroom, 2-bathroom apartment. Perched high above the city, every room offers incredible vistas.This newly renovated unit features: • Spacious open layout with natural...
Laule'a Ohana Retreat: 2 Mauna Lani Villas with 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...
"Kona Nook", Enjoy a Relaxing Cozy Retreat.
Kailua-Kona is waiting for you at this lovely 1-bedroom apartment. With heating, AC, and a hair dryer provided, guests can relax and unwind in this welcoming space. A great place to call homebase while you're away, we hope you enjoy your stay.The "Kona Nook" is a...
KS 211 1BD Partial Oceanview Retreat Steps from the Pool with AC & Lanai
Kaanapali Shores 211 Escape to this 1 Bedroom North Kaanapali Retreat with Partial Oceanview Just Steps from the Pool Welcome to your Maui Retreat: This one-bedroom, one-bathroom condo offers a perfect retreat for those seeking an authentic Hawaiian vacation in an...
Valley Isle 507 Studio Retreat – Enjoy Panoramic Lanai Views Near Beaches
Looking for a Maui getaway where you can relax, explore, and take in the beauty of the island? This 5th-floor studio condo is the perfect place to call home during your stay. Step out onto your private lanai and enjoy breathtaking views of the Pacific Ocean—whether...
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, relax...
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...
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...
Kapalua Golf Villas - Double Retreat in Maui’s Premier Resort, Sleeps 8 in Total
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...
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...
New Listing | Modern Maui Retreat – Steps to Beach & Pool!
Your Island Escape Awaits!Welcome to your serene Modern Maui Retreat! This beautifully remodeled 1-bedroom, 1-bath condo in sunny Kihei offers the perfect blend of modern comfort and tropical charm — ideal for couples, solo travelers, or remote workers seeking a...
Kilipue Retreat by Gather: 3BR Home w/ Loft Desk, Yard, Lanai & A/C
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,...
Tranquil Oceanfront Retreat | Lahaina Shores 421, Pure Aloha!
Lahaina Shores 421 - Many upgrades!Welcome to Lahaina Shores 421—a beautifully appointed oceanfront studio on the 4th floor, designed for comfort and relaxation. Perfect for two guests, this retreat features central air conditioning, a brand-new platform bed with a firm...
New Listing: Oceanfront Studio - A Perfect Escape
Lahaina Shores 533 – Oceanfront Romance & Unforgettable ViewsPerched on the 5th floor of the beloved Lahaina Shores Beach Resort, this beautifully renovated studio offers an unbeatable combination of modern luxury and timeless island charm. With first-class 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...
Puna Rainforest Retreat Hot Spring-Ocean views on 20 acre Estate
Enjoy the solitude of Hawaii's rainforest on a lovely 20 acre estate. This ocean view home is super clean and spacious, on gated private property and very comfortable for up to 10 guests. Appreciate the rainforest sounds, rainbows, starry skies and sunshine, far from...
Kona By the Sea #302 Oceanfront 2-Bedroom Retreat with Central A/C
35-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 the...
This exceptional 4BR/4BA multi-residence retreat pairs two neighboring 5th-floor suites to create more than 2300 sq ft of elevated interior living, thoughtfully designed for sophisticated group travel. One of Honua Kai Resort & Spa’s most coveted premier oceanview 2BR...
Kaunala Retreat | 4BR Oasis w/ Sauna, Lanai, Steps to Velzyland Beach
Tucked within a private gated community just steps from O‘ahu’s golden North Shore sands, Kaunala Retreat blends modern island design with tropical serenity. This four-bedroom, three-and-a-half-bath home offers 2,024 square feet of indoor-outdoor living across a...
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...