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.
Garden Island Retreat - Islander on the Beach #116 - Studio Condo
Beautiful ground level studio #116 w/kitchenette at Islander on the Beach. Just steps away from the beach! Great, quiet location in the resort complex and has an ocean view from the lanai. Islander on the Beach, Hawaiian Style Resort, is set on six acres of oceanfront...
Charming & Affordable Couple's Retreat w/ Ocean Views from Every Room
Sealodge E8 offers the perfect blend of classic island charm with modern touches! This intimate and inviting condo features a queen bed, as well as a twin-sized punee (Hawaiian day bed) in the living room that's perfect for sleeping a child if you're a small family. The...
Refreshed North Shore Retreat W/AC, Community Pool & Tennis!
Refreshed in 2024, this beautifully updated home is the ultimate North Shore retreat, located in the prestigious Sunset Drive neighborhood—one of Princeville’s most sought-after communities. Guests enjoy exclusive access to a private clubhouse with a pool, tennis...
Hauula Beach Retreat-OceanViews, AC, work remotely
*30 day rental. Please inquire. You'll love being minutes away from world class entertainment, incredible beaches, delicious food, and so much more! Many of these opportunities for adventure can be found right outside the front door!When you stay in the Hauula Beach...
Tropical oceanfront retreat with WiFi, hot tub, pool, and sweeping ocean views
Paki Maui 122Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Treat yourself to a vacation you'll never forget when you reserve your spot at this oceanfront getaway in Lahaina....
Perfect Spot to Enjoy Maui Ideal Island Retreat!
**Nohonani 201 – Your Oceanfront Paradise**Welcome to Nohonani 201, a stunning 2-bedroom, 2-bath condo on the 2nd floor, offering breathtaking ocean views from the kitchen, dining areas, living room, and master bedroom. The master bedroom, located ocean-side, features...
Idyllic Island Retreat w/ Pools, Hot Tubs, Fitness Center: Near Beach, Dining
Waikoloa Beach Villas P4Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'An idyllic island retreat awaits at this lavish 3BR/3BA condo, located in the gated Waikoloa Beach Villas....
Tranquil Ground-Floor Retreat: Wailea Elua 105, Set in an Enchanting Property
Wailea Elua #105 – Ocean View Luxury and Secluded Serenity in the Heart of WaileaWelcome to Wailea Elua #105, a beautifully remodeled 2-bedroom, 2-bathroom ground-floor ocean view condo perfectly positioned at the peaceful southeast corner of Wailea Elua Village. This...
Oceanfront Retreat Stunning Views - Makena Surf F-107 - Amazing Snorkeling!
Makena Surf #F-107Discover F-107: Makena Surf's most exclusive marine sanctuary experience. With unparalleled proximity to the ocean, this oceanfront residence is uniquely positioned on a dramatic ancient lava lae in the resort's premier F-building - the closest luxury...
Modern Retreat W/Kitchen and Lanai–Poipu Shores<br>
Step onto your private lanai and take in the panoramic ocean views, where each sunset feels more magical than the last. Escape to this charming and rustic 2-bedroom, 2-bath condominium, perfect for couples, families, ands friends. This unit comfortably accommodates up...
A Hidden Jewel, ideal for a family or Corporate Retreat
TAT License: TA-057-028-1984-01. Welcome to your hidden jewel in Aina Haina, Honolulu! This fully furnished midterm rental offers 3 bedrooms, 2 baths, a kitchen, a living room, & a balcony. This is a 3 bedroom 2 bath private condo within a 3 condo complex. This unit has...
Tropical Retreat Near Waikiki Beach with Parking!
Aloha from Midway Vacations! Our team of local hospitality experts is dedicated to turning your Hawaiian getaway into a reality. When you stay at one of our properties, you can count on a professionally cleaned and meticulously maintained experience. We're even...
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...
WEK 37C Getaway at Wailea Retreat w AC Pool Near Beach and Golf Course
FREE daily activities included with your stay value up to $956! Complimentary admission, every day of your stay*: Lu’au, Golf, Whale Watching (seasonal), Sunset Dinner Cruise, Molokini Snorkel Trip, Alpaca Farm Tour, Pineapple Farm Tour, and Tea Farm Tour. (S3)*One...
Endless Ocean Views at Kahana Reef 315! Your Perfect Maui Retreat.
Kahana Reef 315! The views are never-ending here! Highly desirable third-floor view condo on the Kahana Coast of beautiful west Maui. Appreciate beautiful, unobstructed, panoramic ocean views from your spacious and private lanai. The tropical islands of Molokai and...
Spacious Downtown Executive Retreat | Free Parking
Chic Downtown 1-Bedroom with Free Parking at Aston Executive CentreExperience the best of downtown Honolulu in this updated 1-bedroom unit, located on the 12th floor of the Aston Executive Centre. Enjoy stunning city views through floor-to-ceiling windows while taking...
![[New] Ocean+Sunset View Retreat | Steps to Beach](https://media.vrbo.com/lodging/112000000/111830000/111821800/111821720/7615d25c.jpg?impolicy=ccrop&w=1000&h=666&q=medium)
[New] Ocean+Sunset View Retreat | Steps to Beach
New Listing Special!Welcome to your Big Island oasis at Puako Beach—just steps from world-class snorkeling, surf, and unforgettable sunsets. Enjoy ocean views, the soothing sound of waves, and a spacious lanai perfect for relaxing or dining al fresco. Expertly managed...
Family Retreat W/Kitchen and Lanai–Poipu Shores<br>
As the sun melts into the endless blue, the sky erupts in fiery shades of orange and pink, creating a mesmerizing oceanfront spectacle. Experience breathtaking ocean views from this spacious 2-bedroom, 2-bath condo. Perfect for families and friends, this unit...
Kapalua Golf Villa 21T1: Ocean Views, Spacious Lanai & 1bd/2ba Hawaiian Retreat
Welcome to Kapalua Golf Villa 21T1 offering stunning ocean views! This 1-bedroom/2-bath villa is the perfect Hawaiian retreat! With a spacious lanai, spend your days relaxing and gazing at the beautiful Maui waters.As you enter, you will immediately be drawn to the...
Plantation Hale D2 "The Palm Shade Stay" – A Relaxed Garden-Level Retreat
Welcome to The Palm Shade Stay, your breezy home base on Kauai's lush Coconut Coast. Nestled among swaying palms at Plantation Hale, this freshly updated ground-floor condo features brand-new furnishings, fresh paint throughout, and a newly renovated bathroom—bringing...
Luxurious Waterfront Retreat w/ Views, Soaking Tub, Pools, Hot Tubs at Honua Kai
Honua Kai - Konea 738Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'If you’re considering a luxurious Maui retreat, this beautifully updated one-bedroom condo offers both location...
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...
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...
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
FREE daily activities included with your stay value up to $554! Complimentary admission, every day of your stay*: Whale Watching (seasonal), Sunset Dinner Cruise, Molokini Snorkel Trip, Alpaca Farm Tour, Pineapple Farm Tour, and Tea Farm Tour. (S1)*One ticket per...
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...
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...
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...
Ko Olina Kai 1051A: Relaxing 2BR Retreat, Ideal for Family, Close to Amenities
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.Ko Olina Kai 1051A by Gather, located in the...
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,...
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....
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 – Newly Updated Oceanfront CondoExperience modern comfort and timeless island beauty at our Kamaole Nalu unit, which underwent a full renovation in the summer of 2015. This stunningly remodeled condo features:*Travertine tile floors*Granite...
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...
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...
Sunset Haven: Elegant Beachfront Maui Retreat
Consistently Top-Rated Villa by Maui Visitors!- Pet-Friendly – Bring your furry friend! (make sure you disclose it prior to check-in)- Ocean views from spacious balcony- Comfortable king-size bed with high-end linens- Free high-speed WiFi upgraded with Eero, SmartTV-...
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...
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
Welcome to Holua Kai #20 by Gather, a stunning two-story vacation home located along the Kona Country Club’s Makai Golf Course, providing an idyllic Hawaiian retreat. This home is a fusion of luxury and tropical charm, offering breathtaking coastline views and an open...
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 217Fully equipped comfort greets you when you open our door to Waikiki Grand Hotel® suite 217.Whether visiting for 2 days or 2 weeks, we've tried to ensure everything you need is on...