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.
Seaside Retreat Condo
Welcome to your retreat by the sea. A great ocean view Overlooking Kahaluu Reef Bay. AC & centrally located in the heart of Kailua-Kona right on Ali'i Drive. Free Digital guide with booking with lots of local recommendations. Designed for comfort and thoughtful details....
Puamana Retreat by Gather: Oceanfront 3BR w/ Lanai & Resort Amenities in Lahaina
Welcome to Puamana Retreat by Gather, a breathtaking oceanfront escape where Maui’s coastal beauty unfolds right outside your door. Set within the beloved Puamana community in Lahaina, this two-story townhouse pairs seamless indoor-outdoor living with front-row Pacific...
Private, Peaceful Modern Retreat, Golf Views, 3/3, Lanai, AC, Outdoor Hot Shower
Open space & mountain views Covered lanai Easy access to walking paths Gas BBQ Outdoor hot shower Fully equipped kitchen Air-conditioned bedrooms Ceiling fans in every room Rich wood flooring Media room 65” Smart TV with YouTubeTV & streaming access 12” Queen-size...
North Shore Villa - Relaxed Luxury Retreat
Welcome to your peaceful retreat on Oahu's stunning North Shore, located in the desirable Kuilima East community. Nestled next to the luxurious Ritz-Carlton Oahu, Turtle Bay, and overlooking its world-renowned golf course, this charming vacation rental offers the...
Kaanapali Royal B201: Your Dream Hawaiian Retreat
🌴 Escape to Paradise: Your Dream Vacation Awaits at Kaanapali Royal B201 🌺Imagine waking up in the heart of Kaanapali (Kāʻanapali), where the gentle sounds of swaying palm trees (nā niu) and the scent of tropical flowers (nā pua) welcome you to another day in...
Napili 1st-level serene and peaceful retreat
Welcome to Napili Shores E135, a stunning ground-level 1 bedroom 1 bathroom condo nestled in the heart of Napili featuring a garden view and split AC system. This condo sleeps up to 4 guests. This resort does not have elevators. The living room is enhanced by an...
4 Mi to Beach: Keaau Retreat w/ Relaxing Porch!
'Ke'ena Ma Puna' | Private Outdoor ShowerA tranquil paradise awaits you and your loved one at this cozy 1-bathroom studio in Keaau, Hawaii! After exploring the nearby Paradise Cliffs or Shipman Beach, rinse off in the outdoor shower and unwind on the front porch while...
Hale Moana – Oceanfront Luxury Retreat
Summary:Oceanfront elegance awaits at Hale Moana, a beautifully remodeled, air-conditioned three-story retreat perched above Kukuiula Bay. Enjoy panoramic ocean views from nearly every room, sophisticated interiors with original art and designer furnishings, and...
Lanai + Ocean Views: Secluded Holualoa Retreat!
Outdoor Dining | Fruit Picking On-Site | Short Drive to Snorkeling & BeachesSeeking a serene Hawaii escape? Look no further than ‘Lilikoi Inn!’ With stunning ocean views and a prime location just minutes from the shores of Magic Sands Beach, this 2-bedroom, 2-bath...
Hale Kahakai - Oceanfront Retreat - Direct Beach Access - 30 Day Rental
Important Notice: This property is available for rental with a minimum stay of 90 consecutive days. Rental prices remain fixed and are not subject to reduction based on the length of stay.Welcome to Hale Kahakai! This exquisite single-family oceanfront retreat is...
**Fairways Mauna Lani #1606 - Luxurious 2-Bedroom Retreat: 2 King beds, Remodele
**Fairways Mauna Lani #1606 - Luxurious 2-Bedroom Retreat: 2 King beds, Remodeled with Spa-Like Bathrooms, Steps from the Pool!**Please scroll down for detailed informationWelcome to your dream getaway! This beautifully remodeled 2-bedroom, 2-bathroom townhome is...
Lei Aloha - A Private Retreat, Pool + Fairway Views
Welcome to Lei Aloha, Princeville!This luxurious island home is a 4 bedroom, 4 bathroom home combination of elegance filled with an abundance of amenities. This hidden retreat located in the prestigious resort community of Princeville is one of its kind , and provides...
Masterfully Renovated Ocean View Unit in Waikiki
One of our best listings! Bright and Light One Bedroom, One Bathroom and One Parking (Max 6ft) at the Waikiki Banyan. Full of natural light during day! This partial Ocean View unit in the heart of Waikiki will make your stay in paradise a memorable one.Total of 3...
Oceanfront Bliss at Hale Kamaole 215 - Your Perfect Maui Retreat Awaits!
HALE KAMAOLE, #215Escape to paradise at Hale Kamaole #215, a well-appointed 1-bedroom, 1-bathroom condo located directly across from Kamaole Beach Park III in sunny South Kihei. This second-floor unit offers garden and partial ocean views, updated interiors, and a...
Kauai Loft Retreat PF-H307
Pono Kai's pool and spa will be closed January 6-31, 2026 for the installation of the new pool deck fencing.The Kapaa Public Pool, located less than one mile from the resort, is open to the public.Welcome to Kauai Loft Retreat – Your Perfect Island Escape!Nestled in...
Gorgeous Gated Retreat Near Ocean w/ Pool, Deck, Firepit on 1+ acre!
Enjoy a blissful vacation at the Heavenly Hawaiian Paradise Beach House. This 3BR/2BA retreat is perfect for groups up to 10, offering welcoming spaces both indoor and outdoor to dine and relax in the beautiful Hawaiian weather. Spacious outdoor deck with swimming pool,...
Kauai Dream Retreat: Your Gateway to Coastal Living in Poipu Kai
Book 5 nights get the 6th night free for stays in January 2026!LOCATION LOCATION LOCATIONKauai Dream Retreat: Your Gateway to Coastal Living in Poipu KaiAloha and welcome to Kauai Dream Retreat—a haven of coastal elegance and prime location in the heart of Poipu Kai....
Family Suite #1 - Two rooms w/ shared hot tub, Family suite # 1 - Ulu Retreat + A'ali'i Sunset Suite
Immerse in tranquility at our Ohia retreat with two serene rooms, each with its own private lanai for enjoying nature's symphony. Indulge in the comfort of 14-inch memory foam mattresses and flat-screen TVs. The courtyard, a blend of open skies and cozy corners,...
Luxe Private Princeville Retreat Near Hanalei Bay!
Delight in the very best of Kauai from the comfort & convenience of this spacious private retreat! Perfectly situated in the heart of Princeville just minutes to Hanalei Bay, enjoy relaxing on Anini Beach, a round of golf at Makai Golf Club & luxury resorts simply a...
Ocean Pearl at Turtle Bay Resort - Kuilima Estates West
Ocean Pearl is a luxurious retreat nestled in the heart of scenic Turtle Bay Resort, offering a perfect blend of comfort, convenience, and breathtaking views. With three full bedrooms and two full Jack & Jill bathrooms, this spacious abode provides ample accommodation...
Relaxing Beachfront Retreat - Sugar Beach #235 - Your Perfect Getaway!
SUGAR BEACH RESORT, #235Welcome to Sugar Beach Resort #235, a beautiful second-floor condo with stunning beachfront views. Perfectly located in North Kihei, this oceanfront retreat offers modern comforts, central AC, and the serene atmosphere of Maui’s longest stretch...
Ideal Family Retreat! - Beach Pass Included - Great Location - Beautiful Sunsets
Fairways at Mauna Lani 1001 -- One of the best locations within the complex -- INCLUDES COMPLIMENTARY ACCESS to the parking at the Beach Club (calm water beach with a great snorkeling and restaurant: 5 minutes driving from us) -- Renovated with attention to details in...
Kihei Beach Retreat: Ocean Views and Sandy Feet!
Experience Maui's charm in our 2-bed, 2-bath condo, directly managed by us for a personal touch. Just steps from top beaches and snorkeling, with stunning ocean and West Maui Mountain views. Enjoy our resort-style amenities including a pool, hot tubs, game room, and...
Puna Rainforest Hot Spring Retreat - Green Bamboo Cottage
Studio with oceanview, full kitchen and bathroom, queen size bed, plus small couch for one child or small adult. Perfect for couples. The property offers 1 mile private rainforest trail, pool, steam vents, two steam vent hot springs and private retreat setting...
Ohana Retreat: 10 BR Poipu Estate with Private Pool, Sleeps 28
Summary:Ohana Retreat brings together Lei Ohana, Makanui Estate, with their two guest houses to create a private Poipu haven with a pool, four kitchens, and sleeping for up to 28 guests. Perfect for reunions and large groups, this expansive retreat offers flexible...
Hawaiian Elegance – 5BR Retreat Steps from Mauna Kea & Hapuna Beaches
Welcome to Hawaiian Elegance! From sunrise to sunset, beautiful views surround this exquisite five en-suite bedroom estate in the prestigious Kauna'oa gated community in the heart of the Mauna Kea resort. Hawaiian Elegance is a brand new home just completed in March...
Na Hale 3: Exclusive Family Retreat with Private Pool and Resort Privileges
3BD Na Hale 3 at Pauoa Beach Club at Mauna Lani Resort by Gather is a single-level retreat designed for effortless indoor-outdoor living within the gated Pauoa Beach community. Surrounded by lush landscaping and steps from the immaculate Fairmont Orchid shoreline, this...
Ke Aloha Estate - North Shore Kauai Retreat with Pool, Spa, Gym, Pool Table & Pickleball
TVNC - 4267 - TA-105-498-4192-0124/7 On Island Contact - Kimmy, House of Dreams KauaiRates are based on 10 guests. There is an additional fee of $75 per night per person up to 14 guests. All reservations will require main guest to review and sign a rental agreement for...
Kihei Surfside #304: Spectacular Oceanfront Retreat with Unforgettable Views
Experience the perfect Maui escape at Kihei Surfside #304—an oceanfront retreat offering unforgettable views and coastal comfort. Just steps from Keawakapu Beach, this updated one-bedroom, one-and-a-half-bathroom condo captures the essence of island living with...
Poolside Waikiki Retreat w/ AC, surfboard storage, walking distance to beach!
Located in the center of Waikiki with amenities like A/C, on premises laundry, and bike & surfboard storage, this spot is a no brainer. Directly across from the *eight foot deep* outdoor pool and patio, and just blocks from the beach, this apartment is truly a piece of...
Exceptionally Pristine Haleiwa North Shore Beachside Retreat
FIND PEACE & ESCAPE FROM STRESS HERE. -This is considered one of the best North Shore neighborhoods for location, privacy & safety. The large North Shore Winter surf is here! Check it out just minutes away down a private beach access. Shell collecting, monk seal & green...
Ko Olina Kai Estate #20: Elegant Fairway Retreat with Luxe Amenities
Bordering the signature 18th fairway of the Ko Olina Golf Course, Ko Olina Kai Estate #20 by Gather offers peaceful resort living framed by sweeping green views, gentle trade winds, and warm island light. This spacious two-story home features over 2,200 square feet of...
Ko Olina Kai #17: Spacious, Stylish Retreat with Golf Course Views
Tucked along the prestigious 18th Fairway of the Ko Olina Golf Course, Ko Olina Kai Estate #17 is a private retreat where resort living meets the comforts of home. This executive four-bedroom estate within the gated Ko Olina Kai Resort Community offers expansive fairway...
Fairways Ko Olina 27H: Your Ultimate 3BR Retreat in Hawaii with Resort Access
Welcome to Fairways at Ko Olina 27H, a spacious three-bedroom, two-and-a-half-bath townhouse offered exclusively as a monthly vacation rental within the gated Fairways community on Oahu’s sunny west coast. This comfortable home blends open living spaces with serene...
The Palm Treehouse: 3BR Serene Kauai North Shore Retreat
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...
Discover Paradise at our Waikoloa Village Retreat: Grand Floor upgraded unit.
Contemporary upgraded ground level cozy 1 bedroom with covered lanai with a wet bar looking over the golf course, ready for your relaxing stay. The unit is conveniently located directly across from the communal pool / hot tub.For extra sleeping area, pull out queen in...
Mountain View Retreat Unit 1 - highly rated on leading rental sites!
Peaceful rain forest guest house a few miles from Volcano National Park. Mountain View Retreat is located in a lush and relaxing paradise. Enjoy your coffee or tea in the morning on your own private lanai. For larger parties there is another guest house on the same...
Mountain View Retreat Unit 2 - highly rated on leading vacation rental sites!
Peaceful rain forest guest house a few miles from Volcano National Park. Mountain View Retreat is located in a lush and relaxing paradise. Enjoy your coffee or tea in the morning on your own private lanai. For larger parties there is another guest house on the same...
Sky Villa Estate: Luxury Gated Kona Retreat with Ocean Views
Welcome to your Hawaiian haven, Sky Villa Estate! Kick off your flip-flops and let alohaspirit guide you up the driveway to this secluded gated 5-acre estate, through lushlandscape that feels like a warm hug from the island itself. Deep lush lawns encouragefamily games...
New Upscale Kona Retreat, Ocean Views, Pool, BBQ
Welcome to paradise in Kailua-Kona, Hawaii! 🌴 Escape to this stunning 3-bedroom, 2-bathroom oasis boasting breathtaking ocean views and a private pool for the ultimate Hawaiian getaway. Wake up to the panoramic views of the Pacific Ocean right from your private lanai,...
As seen on Discovery Channel's "Building off the grid" Volcano Home!
Volcano Rainforest Retreat — As Seen on “Building Off the Grid”!To see our home featured on TV:Search online for Building Off the Grid — Season 7, Episode 5: “Volcano Home”Welcome to Volcano Home, a handcrafted 2-bedroom, 2-bath rainforest retreat on the lush slopes of...
Entire House! Peaceful retreat 4BR Waikoloa beach
About this spaceWelcome to our exquisite residence in Ainamalu, the "Peaceful Land" of Hawaii.1. Surrounded by majestic mountains and the ocean, our home offers a serene and captivating backdrop.2. Accommodates up to eight guests, perfect for families or groups of...
Hawaiian Retreat w/ Ocean Views in Captain Cook!
Indulge in the ultimate Hawaiian getaway at this stunning 3-bed, 3-bath vacation rental house in Captain Cook. Upon arrival, you’ll be greeted by 3 manicured acres of mature fruit trees. Past the front door lies access to the ocean-view lanai, which is the perfect spot...
Waikoloa Beach retreat! Top floor, walk to beach+shopping+golf, saltwater pool
Welcome to our happy place, Vista Waikoloa D301! Centrally located in Waikoloa Beach Resort on the Big Island, your condo features:- Spacious 350 sq ft. wrap-around lanai (with peek-a-boo views of Anaeho'omalu Bay)- Gorgeous views of Mauna Loa and Hualalai- Walk to...
Luxurious 4 Bedroom Retreat, Private Pool, Located in KuKui' Ula Community.
***** Construction Disclaimer ***** A new home is currently being built next door, with construction taking place Monday through Friday, 8:00 a.m. – 4:30 p.m. You may hear some daytime activity during these hours. Evenings and weekends remain peaceful, perfect for...
Peaceful Big Island Hawaii Retreat with Private Beach Club Access
Our home is a classic Hawaiian style bungalow (no shared walls) 3 BR / 3 Bath (2 master ensuite) with attached garage parking. It's a space to relax, recharge and enjoy "island time". We have beach cruiser bikes, beach towels, snorkel gear, and paddle boards for your...
HALE KE`PUA! Princeville Tranquil Jungle Retreat!
Summary:Indulge in an unparalleled retreat at Hale Ke` Pua! Our exquisite property nestled in the heart of Princeville with a breathtaking Jungle backdrop.The Space:Welcome to Hale Ke' Pua, (House of Flowers) our spacious, serene space on the beautiful North Shore of...
Ocean + Skyline Views: Honolulu Retreat
1,400 Sq Ft | Walk to Wa'Ahila Ridge State Park | Connects to State Park Trail SystemEnjoy your island vacation in comfort at this picturesque Honolulu vacation rental. This 3-bedroom, 2-bath home features mid-century modern touches, a breezy lanai, and a living room...
South Kauai Tranquil Retreat w/ AC in Poipu
Waikomo Streams is a peaceful, tranquil, and beautiful property with immaculate gardens. Immerse yourself in a paradise garden view on the Garden Island! We have an updated, air conditioned unit that is quiet and comfortable. The property boasts tropical gardens, a...
Tropical Paradise Retreat in Princeville! Full Kitchen, Swimming Pool!
Set on the picturesque North Shore of Kauai, this resort offers stunning ocean and mountain views with easy access to Hanalei Bay’s beaches and hiking trails. Ideal for nature lovers, it provides a serene getaway close to local shops and dining options.This listing is...