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...
Oceanfront Bliss – A Relaxing Retreat with Breathtaking Views
Whether you’re here to soak up the incredible sunsets, spot sea turtles from the lanai, or witness majestic whales (in season),this serene escape is ready to make your island dreams come true. Step inside this fully updated condo and experience modern comfort paired...
KK 307 OceanFront 2BD Retreat with Breathtaking Views
Kulakane 307 Newly Remodeled OceantFront 2Bedroom for Picture Perfect Retreat to Relax Recharge and Rejuvinate. Ocean Views for Beautiful Sunsets and Spectacular Whale Watching FREE daily activities included with your stay value up to $570! Complimentary admission,...
Ke Nani Kai 132 - Spacious 2 BR/2 BA Relaxing Molokai Island Retreat
Located between Oahu and Maui...Molokai is an undiscovered treasure. 'The Friendly Isle' is a family-oriented island with deep connections to its Hawaiian traditions. Unlike the tourism driven other islands, here you can relax, slow down and have your own space. Nowhere...
Serene Eco Retreat: Ocean Views, Waterfalls, and Scenic Trails!
**Reconnect with Nature: The Lotus Room at Maui Eco Retreat**Feel your feet on sacred ground as Nature welcomes you home. Step into the Lotus Room and immerse yourself in the serenity of private trails leading to hidden waterfalls, surrounded by pristine landscapes. Let...
Oceanfront Oasis: Ground Floor Retreat - Sugar Beach #130
SUGAR BEACH RESORT, #130Welcome to Sugar Beach Resort #130, a beautifully updated ground-floor condo that combines modern upgrades with the ultimate beachfront convenience. Located in North Kihei, this oceanfront oasis allows you to step directly onto miles of golden...
Serene Aloha Retreat: Beachfront Bliss in Napili's Charming Studio/Suite
After opening our doors to wildfire survivors during Lahaina’s time of need, we are honored to once again welcome travelers to our cherished slice of paradise. Our updated studio condo at Napili Shores offers everything you need for a restful, memory-making stay on...
Hale Makai Cottage #5: Kauai North Shore Retreat
Hale Makai Cottage #5 offers an idyllic Hawaiian escape for families or groups of friends seeking the beauty of Kauai's North Shore.The cottage features two bedrooms and two bathrooms. The primary bedroom includes a luxurious king-size bed and an ensuite bathroom. The...
Ideal resort retreat with central AC and access to pools, hot tub, golf, & more
Shores at Waikoloa 338Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'As you step off the elevator you will feel the enchanting ocean breezes and an endless array of resort amenities...
Fabulous island retreat near the beach with pools, hot tub & patio
Waikoloa Colony Villas 2105Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Clean, bright, and filled with modern comforts, Waikoloa Colony Villas #2105 is more than ready to assist...
Luxurious Kapalua Golf Villa: Stunning 2BR/2BA Retreat with Ocean & Golf Views
Escape to Paradise at our Luxurious Kapalua Golf Villa!Welcome to your dream Hawaiian vacation at this exquisite 2-bedroom, 2-bathroom retreat, nestled in the highly sought-after Kapalua Golf Villas. From the moment you step foot into this tranquil haven, you'll be...
Stunning Oceanfront Retreat, Kahana Reef 218
Direct oceanfront unit in a highly desirable location right in between the popular areas of Kaanapali and Kapalua. When you sit on the balcony, you have panoramic views looking out to the islands of Lanai and Molokai. You will also see whales and sea turtles and have...
Romantic Tropical Retreat, 150 yds from the Ocean!
Please note, effective Jan 1st. 2026, Hawaii`s Transient Accommodations Tax will increase from 10.25% to 11% for all stays with an arrival in 2026 forward. We may need to collect the tax difference to secure and finalize your booking. We will contact you to confirm the...
Private Cliffside Ohana Retreat at Kalapaki Beach!
Experience the very best of Kauai from the comfort & convenience of this luxury oceanfront retreat! Step outside to enjoy incredible ocean views overlooking Nawiliwili Harbor from your private cliffside balcony, or spend the day kayaking, surfing and relaxing on...
Spacious & Modern Pāhoa Retreat Near Kehena Beach!
Discover the very best of the Big Island from the comfort & convenience of this modern private retreat! Ideally situated in the charming town of Pahoa, enjoy the world-famous black sands of Kehena Beach, the warm waters of Ahalanui Park or explore the inspiring...
Oceanfront Sea Village #3212 retreat with stunning views and open living spaces
Turn moments into memories in this incredible oceanfront Sea Village #3212 property. This two-bedroom, two-bathroom has all one is looking for. Enjoy the open layout of the living area and stunning ocean views from the kitchen to the lanai.Upon entry, you can't help but...
Tranquil tropical retreat with pool, hot tub, and golf nearby
Maui Eldorado Resort E205Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Feel your worries melt away with the ocean breeze as you relax in style at this Lahaina home. Featuring...
Oceanview 5th Floor Retreat Steps from the Beach,
If you're looking for a condo on Maui, look no further. Quiet 5th floor unit in the C Building with views of the ocean, Mt. Haleakala, and the garden from the lanai. Walk across the street to Kamaole Beach Park II for excellent swimming, snorkeling with occasional sea...
Ocean Views, Beach Access, and a Cozy Hawaiian Retreat: Ma'alaea Banyan 416
Maalaea Banyans 416 offers stunning ocean views and is a real charmer, making for the perfect Hawaiian retreat. You can enjoy your morning coffee while watching a whale breach, especially during the season, or turtles almost nightly right from your private...
Oceanfront Retreat w/ Incredible Views Just 90 Seconds from the Beach
Hanalei Colony Resort K4 is a cute and intimate retreat in an off-the-beaten-path location on Kauai's far North Shore, perfect for romantic getaways and escaping the crowds! The sunny and cheerful condo has two bedrooms, with the option to use the second bedroom as a...
Discover Coastal Comfort: Oceanview Retreat at Kamaole Nalu #304
Kamaole Nalu #304 – Modern Ocean View Retreat in KiheiKamaole Nalu #304 is a beautifully remodeled two-bedroom, two-bathroom condo offering ocean views and modern island comfort. Located on the third floor of this oceanfront property, the condo provides an inviting...
Seaside retreat - Twelve steps to the sand! Private and romantic.
2024 Traveler Award winning rental, Hanalei Colony Resort I2 is unique among north shore Kauai condo resorts. These Hanalei vacation rentals are directly on the path to follow, just take a few steps and you're on the sand. And I2 is literally just a few steps to the...
WEK 37C Getaway at Wailea Retreat w AC Pool Near Beach and Golf Course
Wailea Ekahi 37C Experience the Luxury of Wailea at Updated 1Bedroom Condo with Split AC Throughout and Comfortably Furnished and a Short Walk to South Maui Beaches FREE daily activities included with your stay value up to $956! Complimentary admission, every day of...
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...
Hoyochi Nikko A Quaint Oceanfront Retreat in Maui
Hoyochi Nikko 202This two-bedroom unit features a master bedroom on the main level with a king-size bed and a spiral staircase leading to a large lofted second bedroom with a queen-size bed. The unit is tastefully decorated with many custom features, and high vaulted...
Breathtaking Condo #3411: Your Ideal Maui Retreat Awaits!
Welcome to this breathtaking top-floor, Ocean View condo. Immerse yourself in the beauty of your surroundings while enjoying the utmost relaxation.Charley Young Beach, situated mere steps from the condo, showcases immaculate white sands and a family-friendly ocean,...
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...
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...
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...
Recently renovated 1bd oceanfront retreat
You'll enjoy Papakea Resort A305's amazing oceanfront location! This lovely 1-bedroom, 1-bathroom condo offers some of the best views from Papakea Resort that is suitable to accommodate up to 4 guests. This west-facing condo will provide unobstructed oceanfront seats to...
Honua Kai Hokulani 824: Beautiful Luxury 1BR/1BA, Mountain View Retreat!
This property is hotel zoned, and not being affected by the recent proposed legislation.Honua Kai Hokulani 824! Great location with Mountain views! This one bedroom/one bath located at the highly desired Honua Kai Resort offers the perfect Hawaiian getaway.This inviting...
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...
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...
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...
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....
New Listing: Tropical 1BR Retreat in Waikomo Stream Villas, Poipu
Welcome to Waikomo Stream Villas unit 100, your tropical gem in the heart of Poipu! Nestled in lush greenery and surrounded by vibrant flora, our one-bedroom condo is the perfect escape for those seeking tranquility and natural Hawaiian beauty.Why you will love this...
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...
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...
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...
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...
Kona Pacific C416 by Gather: 1BR Condo Retreat w/ Pool & Ocean Views
Welcome to Kona Pacific C416, a beautifully appointed 1-bedroom, 2-bath ocean-view condominium in the heart of Kailua-Kona, Hawai‘i. This 830-square-foot retreat offers modern comfort and tropical tranquility, accommodating up to four guests—ideal for couples,...
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...