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.
Kauna‘oa 7B at Mauna Kea – Private Retreat with Pool, Spa & Beach Access
This two-story luxury townhome at Mauna Kea Resort offers four bedrooms, 4.5 baths, and 3,577 square feet of elegant island living. Set within a private gated enclave, the home features its own pool and spa surrounded by tropical gardens, plus seamless indoor-outdoor...
Maile Retreat ~ Peaceful Home - Kuilima Estates West
This spacious two-bedroom, two bathroom ground floor unit home is your home away from home. Large open living room/dining room is ready to come home to after a long day exploring the beaches or restaurants of the North Shore. Watch the sunrise from your screened in...
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...
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....
Maui Parkshore 302: Large and open 2 bdrm Ocean View condo, sleeps 6.
Enjoy ocean views from this third-floor condo. This unit sleeps up to six (6) people with a queen bed in the master bedroom, two twins in the second bedroom and a pull out sofa bed in the living room. The living area is open to the kitchen and the balcony, creating a...
Tranquil Groundfloor Retreat - Wailea Ekolu Village 401 - Close to Pool & BBQ!
Wailea Ekolu #401 – Your Ocean View Wailea RetreatSurround yourself with sunshine, palm trees, and endless ocean views at Wailea Ekolu #401. This spacious two-bedroom, two-bathroom ground-level condo offers a serene island escape in one of Maui’s most desirable resort...
Charming Retreat with Majestic Ocean Views!
Welcome to one of the best locations in Princeville—beautifully updated with modern flooring, stylish furniture, and fresh island-inspired décor! Perched on a bluff above the sparkling Pacific, this beautifully updated condo at Pali Ke Kua offers sweeping views of lush...
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 court,...
Gingerhill Farm Retreat. Commune with Nature In South Kona.
Gingerhill Farm is located on five acres of organic orchards and gardens nestled just above famous Kealakekua Bay. We offer serenity and escape mere minutes away from local restaurants and shops.The Sunset Suite is a large room in the main house with private bathroom...
Waikoloa retreat with pool & tennis courts
Summary:Near Golf Course and Ocean, Large Lanai, Top FloorThe Space:Welcome to your Waikoloa retreat – a relaxing island escape surrounded by golf views, palm trees, & resort comforts! Enjoy peaceful mornings on the lanai & unwind after beach days with top amenities:-...
New! Bright, Coastal Retreat Plus Athletic Club
Bright Coastal Retreat with Poipu Athletic Club MembershipWelcome to your sunny Kauai escape! This beautifully updated 1-bedroom condo at Kiahuna Plantation (Unit #402) offers the perfect blend of island charm and modern comfort. Take in the gentle sway of palms and...
Spacious Entire Home w/ Heated Pool, 180-Degree Ocean View & 7 mins to Beaches!
Welcome to Kona Phil's home! Escape to your Big Island ocean-view retreat, where comfort, style, and tropical serenity come together. This spacious single-level home features a rare central atrium, filling the interior with natural light and lush greenery, creating 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...
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...
Spacious Maui Paradise Retreat-Across from 2 Fave Beaches MK-B202
Experience paradise in this fantastic 2-bedroom, 2-bath Maui Kamaole condo. Located in the coveted B building, closest to the main pool pavilion and pristine Kamaole beaches, this newly renovated vacation rental sleeps up to 6 guests comfortably.Highlights:• Prime...
Waikomo Stream Villas 103 - 1st Floor, Garden View
Summary:Ground-floor garden-view condo in a lush tropical setting across from Kukuiʻula Village. This one-bedroom retreat offers a private lanai, king bedroom, sleeper sofa, full kitchen, and in-unit laundry—perfectly located near Poipu’s beaches, dining, and...
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,...
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...
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...
Maui Parkshore 409: Have fun in this two bedroom, two bath Ocean View condo.
Have fun in this two-bedroom, two-bath Ocean View condo. Conveniently located in South Kihei, there are shops and restaurants just a block away. There is a popular beach park across the street and other beautiful beaches are just a short walk or drive away. There is a...
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...
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...
Keauhou Punahele A104 - Cozy Island Themed 2 Bed 2 Bath
Say aloha to your own slice of paradise in this beautiful island-inspired 2-bedroom, 2-bath condo at the Keauhou Punahele complex. Overlooking the lush greens of Kona Country Club and the sparkling Pacific beyond, this peaceful retreat combines comfort, privacy, and the...
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...
Kamaole Beach Royale Unit 305:1 Br/2 Ba Across from Kamaole Beach Park I
Enjoy 180 views from the 3rd-floor living room and a private lanai with table and chairs where you can relax and listen to the waves crash on the shore. In the winter months, you can see the whales playing in the ocean and throughout the year you can watch the boats...
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...
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...
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...
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...
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...
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...
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...
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...
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....
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....
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...
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...
Chic Condo steps from White Sandy Beach Fast Wi-Fi
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...
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...
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...
Ground floor beachfront escape at Maalaea
Hono Kai A3 is a charming ground-floor, 1-bedroom, 1-bathroom condo that features a window A/C in the bedroom and ceiling fans throughout for added comfort. Unit A3 can accommodate up to 4 guests. The bedroom boasts a queen-size bed and a queen-size sofa sleeper in the...
Kihei Akahi D414 1br/1ba garden view condo at Short walk to beaches, shops
**PLEASE NOTE: NEIGBORING UNIT D616 WILL BE UNDERGOING RENOVATION FROM 01/05/26 - 03/20/26. EXPECT NOISE**Enjoy Ocean Views from this one-bedroom Ocean View Condo. This unit sleeps four (4) people with a king bed in the bedroom and a sofa bed in the living room. The...
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-...
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 of...
Kona Paradise - Stunning Ocean Views from Lanai - Captain Cook, Hawaii
Escape the lights and traffic of downtown Kona and unwind in this peaceful oceanside retreat. This 2-bedroom, 2-bath home offers breathtaking ocean views, nightly sunsets, and the serene beauty of Hawaii’s natural landscape, all from your private lanai.Perched above...
Waikoloa retreat with BBQ & pool access
Summary:Renovated Kitchen, Ground Floor CondoThe Space:Welcome to your peaceful Waikoloa Village escape - a relaxing island stay surrounded by tropical gardens & resort comforts:- Sleeps 4 | 2 bedrooms | 2 beds | 2 baths- Access to pool, hot tub & gym- Private lanai w/...
Peaceful golf retreat with shared pools
Summary:Discount Golf, Ocean views, On Golf CourseThe Space:Welcome to your peaceful Waikoloa escape, perfectly set along the fairway with breezy ocean views and easy access to beaches, golf, and local dining:- Sleeps 6 | 2 bedrooms | 3 beds | 2 baths- Private lanai w/...
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...
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....