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.
Keauhou Kona Surf & Racquet 188: Renovated Oceanfront Retreat
Welcome to Keauhou Kona Surf & Racquet 188 by Gather, a fully renovated oceanfront townhome nestled along the stunning Kona Coast of Hawai‘i. This two-bedroom, two-bathroom retreat spans 921 square feet across two levels and accommodates up to six guests. Offering...
Maui Breeze Retreat at Ho'olei openings Jul 19-29, Aug 22-Sep 14 & Sep 25-Oct 11
Surround yourself with the lush scenery of Maui Breeze Retreat at Ho'ol!ei, a tastefully decorated two-story villa with spectacular views of the Pacific Ocean. Your exquisite island retreat in Wailea offers spacious, well-appointed living quarters embraced by manicured...
HALE KE`PUA! Princeville Tranquil Jungle Retreat!
Welcome to Hale Ke' Pua, (House of Flowers) our spacious, serene space on the beautiful North Shore of Kauai. Your private area on the bottom floor within the home has its own private entrance, bedroom, full bath, living room, kitchenette, BBQ and gorgeous lanai with...
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,...
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...
Kehena Black Sand Beach House: 2 BR Eco-Retreat with Ocean View & Swim Spa
The ultimate Hawaii eco-retreat. Timeless design for indoor-outdoor relaxation, dining and sleeping. Experience ocean views and crashing waves from wide-open bifold doors. Walk nextdoor to Kehena black sand beach, or drive the Red Road to the state's only hot springs at...
Ohana Retreat - The Real Hawaiian Experience
Experience the Beauty of Hawaii at Ohana RetreatOhana Retreat is the ultimate getaway for large families looking to embrace the breathtaking beauty of Hawaii. Our spacious island-style home features eight luxurious bedroom suites, each complete with a private bath, wet...
**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...
Ground-Floor Retreat W/Ocean Views-Kiahuna 2166
Kiahuna Plantation unit 2166: This modern tropical one-bedroom ocean view unit on the ground floor is a rare find and provides the utmost comfort with cool flooring and decorative carpeting, two cooling ceiling fans, and floor-to-ceiling windows allowing for plenty of...
Comfortable, single-level retreat with fast WiFi & washer/dryer - dog-friendly
Puni Mauka A | 31-Day MinimumOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Located less than five miles from Pāhoa for convenient shopping and dining and just two-and-a-half miles...
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...
'The Aloha Spirit ' Relaxing Retreat
We have remodeled our spacious one bedroom condo with amenities to be our home away from home. We invite you to make it yours while you enjoy the finest beaches and sunny weather of Kihei. Keep in touch with free wireless internet.Perfect for two people featuring a...
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...
A Tropical Retreat with Garden & Water Views + Resort Amenity Access
Welcome to Maui Kamaole C-109, a serene ground-floor condo located in the heart of Kihei, Hawaii. Perfect for a small family or a couple’s getaway, this inviting vacation rental comfortably accommodates up to 4 guests with its spacious primary bedroom and a queen...
Sweet Lava Retreat with Epic Ocean and Volcano Views
** Please note that the House is not a fit for children under 6 years old or the elderly, as there are lots of stairs and balconies, a steep ladder within the Main House, and there is uneven lava in the yard.Welcome to the Hakuma House, a cozy off-grid retreat with...
Pili Pono: Elegant Honolulu Retreat with Pool & Private Oasis
Welcome to Pili Pono, a show-stopping 5-bedroom, 6.5-bath luxury estate set within Honolulu’s prestigious Black Point enclave. Spanning 7,470 sq ft of indoor–outdoor living space on a fully enclosed, gated 0.33-acre lot, this custom-designed retreat blends...
Garden Retreat w/Ground Floor Ease - Kiahuna #2115
Kiahuna Plantation #2115: Tropical décor delights in this 690sf rare deluxe ground-floor suite. You and your friends or family can easily access the grounds from your ground-floor balcony and walk to world-famous Poipu Beach which according to "Travel Channel" was once...
Wailea Ekahi 24B - Modern Garden Retreat w/ Lanai, Split AC & Stylish Renovation
Nestled on the ground floor, Wailea Ekahi 24B is a beautifully remodeled one-bedroom, two-bath condo featuring a sleek, modern design and effortless indoor-outdoor living. With elegant finishes throughout, including quartz countertops and stainless-steel appliances,...
Cozy 3bd/3b Beach Retreat, Sleeps 10, AC, WiFi, Fam-Friendly in fantastic Koloa
Escape to paradise in this relaxing 3 bed/3 bath retreat at the Pili Mai condos located on the Kiahuna golf course. This unit can sleep up to 10 guests, relax in its plush interiors with a king bed, 1 queen bed and a cozy bunk room (1 queen, 1 full, 2 twin beds),...
Kaia Villa, at Turtle Bay - Modern North Shore Oahu Retreat w/Lanai & Golf Views
Debuting 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 designed for comfort and relaxation.Every detail has been curated...
Kalama Terrace Renovated Retreat, Centrally Located with AC!
Welcome to Kalama Terrace: Your Stylish, Centrally Located Kihei Retreat!Step into island living at Kalama Terrace, Unit P211—an inviting, fully renovated condo in the heart of Kihei. Perfectly situated just a short stroll from the sandy shores of Kamaole Beach and...
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...
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...
Kauai Dream Retreat: Your Gateway to Coastal Living in Poipu Kai
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. Situated along the lush Greenbelt, this 3-bedroom retreat...
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...
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...
NEW Modern Family Retreat - Hanalei Happiness - Near Best Beaches, Trails & Eats
Step into an elevated retreat, thoughtfully designed for traveling families. This modern hideaway is rich in amenities and curated for comfort, all while embracing the vibrant spirit of Hanalei.- Just 8 Minutes to Hanalei- Close to Best Beaches, Trails & Eats- Ultimate...
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...
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...
Top Floor Retreat w/Mtn Views & Beach Access, 1537
Located on the top floor, this stunning, air-conditioned retreat offers the ultimate in luxury. With no stairs to navigate and steps from parking, you'll enjoy effortless access to your private oasis, complete with breathtaking views. No matter your vacation needs, this...
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...
🐬Georgeous 5-STAR Wailea Retreat!🏝Tranquil Corner unit, Top tier Upgrades🌈
Wailea Grand Champions Villas -- Condo #188Aloha!You are coming to Maui for your Dream vacation---Why not stay in a Tranquil, spacious condo full of High-end amenities while enjoying the island? We welcome you to share our well-loved Maui paradise in stunning Wailea!...
4 BR Hawaiian Plantation-Style Home with Pickleball Court
Old Hawaii at its best! Enjoy the updated traditional home nestled within a fully enclosed and private one-acre tropical estate! Chase the keiki (kids) or grandkids on the spacious lawns, or just enjoy the many tropical trees and plants—coconut, banana, mango, ulu...
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...
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...
2 Bed Maui Retreat with 5 miles of beach!
Kanai A Nalu, what a gorgeous beach front condo! It's a great remodel with tile flooring throughout, island-style furniture, and a stunning kitchen with a full-size front load W/D! All the comforts and conveniences of home, but it's in paradise! With 2 bedrooms, one...
Forest Retreat Eco-Lodge - 24 acres of private land.
Picture Shangri La with rolling mists and sunshine over the canopy of Ohia Lehua with the tip of Mauna Kea poking through the valleys off in the near distance...Ahu Lani Retreat Center is an educational and retreat facility located at 3,000 feet elevation on the Hamakua...
AS SEEN ON TV- Rated #1 Northshore Rental/Retreat with the "Wow" Factor
IF YOU'RE PINING FOR A LUSH, LAZY, LANGUID ESCAPE...A BAREFOOT TRANQUILITY...A BALMY, PALMY, SEA-SCENTED ADVENTURE...LOOK NO FURTHER!!Rated #1 Because...1. AS SEEN ON TV - The Discovery Channel recently filmed our home, Hale Mana, for the premier episode of a new TV...
Rainbow Retreat
*MOLOKAI - NOT MAUI*Here at Rainbow Retreat, we take your comfort extremely seriously. From the Cozy Earth bamboo bedding (Oprah's favorite, 5 years running) to the quality furniture and design you will sink into and enjoy the quiet.Comfortable, minimalistic...
Waimanalo Beach Cottages – Tranquil Island Retreat Steps from the Shore
Uncover the allure of Waimanalo and lose yourself in the tropical paradise of Waimanalo Beach, where our exquisite cottages and breathtaking surroundings await. Embark on a journey of discovery by indulging in the myriad of exciting activities we have to offer....
❤️PiH❤️ PACIFIC VISTA RETREAT ★ Luxury Retreat w/ Ocean Views ★ Heated Pool
Brought to you by Paradise in Hawaii Luxury Homes.Welcome to Pacific Vista Retreat, a part of our Hawaiian Luxury Collection.Pacific Vista Retreat in Kahakai Estates is a wonderful 5-bedroom home, minutes away from downtown Kailua-Kona. It has some of the most amazing...
Stunning Beachfront Retreat 45 steps from Sugar Beach
Welcome to your tropical paradise! Step into our inviting ground floor condo, just a stone's throw from the golden sands of Sugar Beach. Featuring modern furnishings and cozy beds, you'll feel perfectly at home here. Unwind on your private lanai, where you can soak up...
Fairways Ko Olina 27H: Your Ultimate 3BR Retreat in Hawaii with Resort Access
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.Step into paradise with a stay at Fairways at...
Sunset Suzy's tropical retreat! One free night! After 7 nights.
Sunset Suzys Tropical Retreat is located perfectly 15 minutes outside of Hilo town in a beautiful neighborhood called Hawaiian Paradise park.. It is located on a beautiful one acre lot, filled with fruit trees, green grass, green geckos, and tropical birds. There are no...
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...
Magical Lava Temple Eco-Retreat w Volcano Views and Black Sand Beaches
Experience an unforgettable stay at the Magical Lava Temple, a 3BR/1BA off-grid sanctuary located 4 miles from the base of the world’s most active volcano. Surrounded by lava fields and breathtaking views, this open-air loft offers a unique connection with nature....
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...
Breathtaking 1 Bed True Oceanfront Retreat Maui
Aloha, E komo mai (welcome) to Napili Point Resort Unit A13 in West Maui, Hawaii"You will absolutely LOVE this privately owned, Spectacular, 1 Bedroom Oceanfront Condo (A Unit) at the exclusive Napili Point Resort in Maui". - Actual quote from a guest. Bring your...
Exceptionally Pristine Haleiwa North Shore Beachside Retreat
FIND PEACE & ESCAPE FROM STRESS HERE. -This is considered one of the best North Shore neighborhoods! Avoid most of the North Shore's traffic mess by not having to drive past popular "Turtle Beach". The large Winter surf is here! Check it out just minutes away down a...
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....