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.
Tranquil Retreat Sunbelt of Hawaiian Paradise Pk
Summary:Discover the charm of island living in this spacious home nestled within the serene enclave of Hawaiian Paradise Park. Enjoy the essence of the sun-soaked Sunbelt region, where each day invites you to embrace the beauty of Hawaii's natural landscape. With ample...
Kihei Retreat w/ Kamaole Sands Resort Amenities!
Stay at this 2-bedroom, 2-bathroom vacation rental, and get ready to experience R&R like never before. The condo boasts at-home essentials and ample resort amenities to ensure an unforgettable stay. Along with swimming and surfing, you can also experience great...
KAS 4413 Remodeled 2BD Beach Retreat Across Beach w Pool AC
Kamaole Sands 4413 Remodeled Coastal Style 2 Bedroom, 2 Bathroom Beach Retreat Across the Street from Kamaole III Beach Park in Kihei! FREE daily activities included with your stay value up to $554! Complimentary admission, every day of your stay*: Whale Watching...
Vacation Retreat at Kamaole Sands, Steps from Kamaole Beach III!
Experience a rejuvenated retreat at Kamaole Sands, ideally located just steps from the stunning Kamaole Beach III in South Kihei, Maui. Our recently refreshed rental condo is designed to provide a clean, light, and bright atmosphere, featuring a new king-size mattress,...
Cheerful, Classic Hawaiian Retreat w/ Incredible Views & Updated Kitchen/Bath
Located on the seaside cliffs of Kauai’s beautiful North Shore, Ali'i Kai 4303 is a comfortable, top-floor retreat with the most incredible ocean views in every room! It's truly a whale watcher's dream come true. Inside you'll find two attractive bedrooms, each with...
Charming Oceanfront Condo with AC – Kihei Surfside #311: Your Perfect Retreatnnn
Kihei Surfside #311 – Ocean Views, Modern Comfort, and Split-Duct ACWelcome to Kihei Surfside #311, a stylish and comfortable 1-bedroom, 1.5-bathroom oceanfront condo located on the third floor of one of South Kihei’s most iconic coastal resorts. With sweeping views...
Island retreat at Kiahuna Golf Club - Poipu Athletic Club pool & hot tub access
Hale Moana KaiOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Experience the tropical vacation of your dreams at this stylish and spacious home overlooking the Kiahuna Golf Club....
Top Floor South Kihei Retreat with Panoramic Ocean Views!
RARE FIND! Oceanfront Kihei Penthouse with a 32 ft. private lanai Experience the epitome of Beach Town living while relaxing in the welcoming comfort of our top floor, South Kihei vacation home. Indulge in breathtaking ocean and sunset vistas from your private double...
Sunny Pahoa Retreat: Snorkel, Hike & Shop!
Discover miles of lush rainforest and winding roads that hug the beautiful coastline when you stay at this 3-bedroom, 2-bath Pahoa oasis. The vacation rental provides a peaceful base with amenities and comforts that are essential for a seamless vacation experience....
Summer Special Retreat
One bedroom unit. Includes king size bed, ceiling fans, flat screen TV, full kitchen set up with microwave; A beautiful, large pool area with plenty of lounge chairs. Barbecue area; large laundry facility located on property. Located in the heart of Kihei Town. Located...
New Listing! Recently updated oceanview retreat
Welcome to Maui Parkshore 306 — Your Maui Beach Retreat Awaits! Say aloha to your island getaway at Maui Parkshore 306, a beautifully updated 2-bedroom, 2-bathroom condo that sleeps up to 6 guests. Perfect for families, couples, and beach-loving friends, this coastal...
Steps from the Beach Family Retreat w/Free Parking in Boutique Style Building
Book with confidence! This property is professionally managed by Ali'i Beach Rentals, an award-winning property management company.Cabana at Waikiki - 2551 Cartwright Road on the 2nd Floor (NO pool and NO elevators)Living Room:- Sofa Sleeper- Flat screen TV- Free WIFI-...
Top Floor Ocean View Unit: 2 Bed, 2 Bath, AC, Maui Retreat! Island Sands 600
This top floor corner unit offers amazing ocean views!! Enjoy radiant sunsets from your private lanai overlooking Ma'alaea Bay. Light and bright as you enter, this beautifully designed 2 bedroom, 2 bathroom unit features fresh paint and new wood flooring throughout. The...
Special Rate! Maui Kamaole D103! Ground floor condo! Garden Retreat!
Maui Kamaole D103 provides an exceptional Hawaiian retreat! This ground floor, 1bedroom condo comfortably accommodates four. Enjoy the large private lanai and garden area!Take in the charm of this condo. Open and inviting living area offers the perfect setting to relax...
Serene Ocean View Retreat in Keauhou Palena
Welcome to your ideal getaway at our cozy ocean view condo in Keauhou Palena! Nestled on the serene 16th fairway of the prestigious Kona Country Club, this ground floor unit is perfect for those looking to relax and unwind.This charming 2-bedroom, 2-bath condo offers a...
Sea Breeze Retreat at Turtle Bay - Kuilima Estates West
Aloha and welcome to our Sea Breeze retreat, a 2-bedroom, 2.5-bath condo at Turtle Bay! Step outside the living room onto a beautifully manicured lawn overlooking the Fazio Golf Course. This gated condo offers the perfect blend of relaxation and convenience, just a...
Kona Lunapule 205B: Tranquil 2BR Retreat with Ocean Views
Kona Lunapule is centrally located in Kailua Kona, in the Island of Hawaii. It's just a short drive to local restaurants and shops along the coast of Ali’i Drive. This quaint complex features a communal pool and onsite parking. Upstairs you will find 205B; a quiet and...
Stunning retreat with oceanfront views
Welcome to Mana Kai 501, where luxury meets paradise in this exquisite 2-bedroom, 2-bathroom upscale condo, accommodating up to 4 guests. As you step into this stunning retreat, be greeted by direct oceanfront views and tastefully appointed Hawaiian-inspired decor....
Discover the ultimate Hawaiian retreat at Kanaloa Condominium
Welcome to this spacious and beautifully appointed 3-bedroom condominium at Kanaloa Condominium at Outrigger, nestled in the stunning surroundings of Hawaii. This luxurious unit offers a blend of contemporary design and island-inspired decor. Enjoy breathtaking views of...
The Cottage: Oceanfront Honeymoon Retreat w/Gorgeous Views, By Kahalu'u Beaches
This stunning property is now accepting longer-term stays at reduced rates. Please inquire for details.Experience the exhilarating sounds of the ocean just outside your door at The Cottage, a charming one-bedroom cottage where you'll spend each night taking in the...
Your Perfect Ocean View Retreat in a Desirable Location! -Kamaole Nalu #405:
Kamaole Nalu #405 – Ocean View Comfort with Modern UpgradesKamaole Nalu #405 offers the perfect blend of modern comfort and timeless island beauty. This two-bedroom, two-bathroom condo underwent a complete renovation in the summer of 2015 and continues to shine with...
Beachfront retreat with lanai, WiFi, pool, & hot tub - prime turtle spot
Maalaea Banyans 105Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Enjoy lying on lounge chairs in front of a beach, watching sunsets from your lanai, or just seeing if the sandy...
Ko Olina Kai 1051A: Relaxing 2BR Retreat, Ideal for Family, Close to Amenities
Tucked inside the gated community of Ko Olina Kai, Ko Olina Kai 1051A by Gather is a welcoming two-bedroom, two-bath condo perfectly suited for extended stays. With 1,144 square feet of living space, tropical landscaping views, and resort amenities just steps away, this...
Sunset Haven: Elegant Beachfront Maui Retreat
Summary:🔹 Walk to Charley Young Beach – Just 3 blocks away 🌅 Ocean Views – Enjoy coffee on the private lanai 💤 King-Size Bed – Luxury linens for restful sleep 📶 Fast WiFi & Smart TV – Work& stream seamlessly 🏖️ Beach Gear Included – Chairs,...
Central 2-Bedroom Retreat: Steps from Kalapaki Beach with Air Conditioning
Comfort and Convenience in the Heart of Kaua‘i – 2-Bedroom Vacation RentalEnjoy the best of Kaua‘i from this centrally located, split-level 2-bedroom condo in Līhu‘e, just minutes from the airport and ideally situated near Kalapaki Bay. Whether you’re here to...
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....
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...
Ground Floor Treasure: Beautiful Oceanfront Retreat - Kihei Surfside #107
Kihei Surfside #107 – Ground-Floor Ocean View Retreat Just Steps from the BeachEnjoy the relaxed charm of South Kihei at Kihei Surfside #107, a ground-floor ocean view condo with direct access to the resort’s iconic oceanfront lawn. This 1-bedroom, 1-bathroom unit...
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...
New listing! Poipu 3br Retreat with Pool and Gym
Poipu Retreat with Mountain Views and Resort-Style AmenitiesDiscover this breathtaking second-story sanctuary in the prestigious Pili Mai resort, where panoramic views of Kauai's stunning South Shore create the perfect backdrop for your tropical getaway.Nestled within...
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...
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...
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...
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...
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...
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.
I also list my available units with 𝐅𝐢𝐧𝐝𝐢𝐧𝐠 𝐌𝐞𝐢𝐥𝐢 where guests can save up to $1000 on certain weeks or custom stay requests available. Nestled on the golden crescent of Poipu Beach, hailed as one of America's finest shores, our...
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...