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.
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...
Oceanview 2BR Condo at Makahuena | Multi-Level Poipu Retreat, Resort Amenities
E Komo Mai, Welcome to The Makahuena 4304!“The Makahuena” is located on the southernmost point of Kauai. This unique oceanside resort is situated on the edge of a bluff providing spectacular coastal views. This 2-bd/2.5-ba is a multi-level condo on the second story of...
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,...
🌺 Wailea Beachfront Escape — A One-of-a-Kind Hawaiian Retreat
This isn't your typical vacation rental. Unit 43C at Ekahi Village is a thoughtfully renovated, ground-floor condo decorated in rich Hawaiiana style — Persian rugs, original Hawaiian artwork, leather sleeper sofa, antique furnishings, and a king-size bed dressed in...
WEK 37C Getaway at Wailea Retreat w AC Pool Near Beach and Golf Course
Escape to the natural beauty and serenity of Hawaii at Wailea Ekahi 37C. Located in the exclusive resort town of Wailea on the sunny South Maui coast, this roomy ground floor condo is the perfect getaway. Take a short stroll to the renowned Keawakapu Beach, lounge next...
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...
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...
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 a...
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....
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...
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...
Grand Champion Villa: Luxury Stay, Pool, Fast WiFi
Summary:🏖 Prime Location – Walk to beaches & top dining 🛏️ King Suite + Sofa Bed – Comfort & space for all 🌅 Private Lanai – Relax with poolside views 🍳 Fully-Equipped Kitchen – Cook with ease 📺 82” & 65” Smart TVs + High-Speed Wi-Fi 🌬 A/C + Ceiling Fans – Stay cool...
Beautifully remodeled condo with Maui breezes
Kahana Manor 501 is a beautifully remodeled 2-bedroom, 2-bathroom condo on the 5th-floor condo that can accommodate up to 6 guests and is accessible by an elevator. Dine inside or outside on your lanai, a great place to enjoy a meal! The condo offers ceiling fans in...
Spacious 4-Bdrm - AC & Big ocean views!
Bring the whole family—or even two! This expansive two-level, 4-bedroom, 4-bath home in the heart of Kailua-Kona offers incredible space, comfort, and island charm. Designed for large groups and gatherings, you’ll have plenty of room to relax, connect, and make memories...
Quaint Island Charm - As Close to the Beach As You Can Get!
Hanalei Colony Resort J3 is a tranquil, off-the-beaten-path retreat on Kaua'i's far North Shore, perfect for those seeking a peaceful escape surrounded by natural beauty! This charming, vintage-style condo features two bedrooms, with the option to use the second bedroom...
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...
Oceanfront paradise dreamhomeOn the Ocean, Ocean Front Property"Tired of Waikiki???"NOTE: 179 day minimum stayFish & sea come to greet you "Aloha" in the morning as you wake up to a glassy blue green pristine bay.Located on the best part of Kaneohe Bay you will hear the...
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.
**Property Project Notice: Please note that the Maui Parkshore complex will undergo exterior spall repair and painting March 30 – June 2026. Construction activity, noise, and temporary restrictions on lanai or stairwell access may occur during work hours. Dates and...
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...
B2 Poipu Makai Oceanview Retreat | AC & Whales
Oceanfront condo at Poipu Makai with breathtaking, up-close ocean views. This second-floor 2-bedroom, 2-bath unit features rare covered parking, an updated blue sofa, and stunning sunset, whale, turtle, and seal sightings from the lanai, living room, or kitchen. Walk to...
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 Story home, 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...
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
FLASH SUMMER SALE!!! We're offering exclusive discounts on all summer stays booked this week—don't miss out on these updated lower rates.Kamaole Sands 4413 Remodeled Coastal Style 2 Bedroom, 2 Bathroom Beach Retreat Across the Street from Kamaole III Beach Park in...
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.
**Property Project Notice: Please note that the Maui Parkshore complex will undergo exterior spall repair and painting March 30 – June 2026. Construction activity, noise, and temporary restrictions on lanai or stairwell access may occur during work hours. Dates 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...
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...
Aston Ka'anapali Shores 550 | Garden View Retreat – Pool, Hot Tub & Spa
This unit is filled with sunlight and creates a welcoming environment for anyone looking to spend time in and out of their unit while on Maui. The condo is simple but thoughtfully furnished and provides you with everything necessary for a successful Maui vacation from...
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...
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...