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.
Comfortable Retreat w/ Balcony + Breakfast Near Waikiki’s Dining & Shopping Site
Unwind in a spacious suite with private lanai, deep soaking tub, free WiFi, and plush bedding. Enjoy continental breakfast with Kona coffee, then stroll to Waikiki Beach or nearby shops. After exploring, relax by koi ponds or dip in the pool. Perfect for couples,...
Tranquil Retreat | Onsite Pool | Free Breakfast | Couples' Retreat!
Unwind in a spacious suite with private lanai, deep soaking tub, free WiFi, and plush bedding. Enjoy continental breakfast with Kona coffee, then stroll to Waikiki Beach or nearby shops. After exploring, relax by koi ponds or dip in the pool. Perfect for couples,...
Peaceful Retreat | Onsite Pool | Free Breakfast | Couples' Retreat!
Unwind in a spacious suite with private lanai, deep soaking tub, free WiFi, and plush bedding. Enjoy continental breakfast with Kona coffee, then stroll to Waikiki Beach or nearby shops. After exploring, relax by koi ponds or dip in the pool. Perfect for couples,...
Relaxing Couple Retreat | Spacious Suite w/ Living Area | Free Breakfast
Unwind in a spacious suite with private lanai, deep soaking tub, free WiFi, and plush bedding. Enjoy continental breakfast with Kona coffee, then stroll to Waikiki Beach or nearby shops. After exploring, relax by koi ponds or dip in the pool. Perfect for couples,...
Family and Friends Retreat! City View, Outdoor Pool, Kitchenette!
Family-friendly property with a pool, only 2 blocks from the beachThis listing is for a room within a hotel.✦ Your room is 1440 sq. ft, equipped with complimentary toiletries, TV.✦ Cleaning services included in the nightly price.There are a few additional details to...
Waikiki 1BR Retreat at Kalia Suites – Full Kitchen, Walk to Beach & Ala Moana
Enjoy a modern Waikiki stay in this one-bedroom suite at Kalia Suites, a Hilton Grand Vacations Club property ideally located near Ala Moana Beach Park and the gateway to Waikiki. Designed for comfort and flexibility, the suite features a private bedroom with a king...
Your Kona Getaway Awaits: 2‑Bedroom Island‑Style Retreat at Wyndham Hawaiian
Nestled in Kailua-Kona, this peaceful resort offers guests a perfect retreat. The two bedrooms each feature a king bed, providing plenty of space for restful nights. With two bathrooms, including one with a jetted bathtub, guests can unwind in comfort. A nice living...
This one-of-a-kind 3BR + den ground-floor offering at the acclaimed Kaanapali Alii, set in the heart of Kaanapali Beach, pairs two luxurious neighboring suites into one spacious island retreat. Together, they create an exceptional Maui getaway designed for relaxing,...
Premium Bright City-View Retreat - Any Premium Rm
Step into this bright and inviting bedroom featuring a comfortable bed with tropical linens, warm lighting, and a private balcony overlooking the city. Enjoy peaceful mornings with fresh air and skyline views right from your room. Much larger than a standard hotel room...
Kaimana Villa: Princeville Retreat w/ Lanais & Pool
Set within the lush, gated grounds of Nihilani at Princeville, Kaimana Villa at Princeville offers generous space, multiple lanais, and a calm residential feel on Kaua'i's North Shore. With 1,874 square feet of interior living and garden-facing views, this two-story...
Bright Island-View Retreat 8 guests - COMBO 15th
2 bright and breezy, tropical-inspired studio units with warm island décors. Floor-to-ceiling windows open to a private balcony with city views, filling the space with natural light.PLEASE NOTE: This listing is for TWO SEPARATE STUDIO APARTMENTS in the same building and...
Island-Inspired Cozy Retreat - Free WIFI
Bright and inviting, this tropical-inspired studio features a cozy bed, vibrant island décor, soft lighting, and a peaceful ambiance. Floor-to-ceiling curtains open to city views and a private balcony, perfect for taking in the fresh air and sunshine. A relaxing,...
This exceptional paired offering combines two neighboring suites to create an elevated 4BR retreat designed for effortless island living. Suite 113, widely regarded as Honua Kai’s premier two-bedroom floor plan, offers 1325 sq ft of beautifully appointed interior space,...
IA21 Ocean Breeze Retreat: Luxe High-Rise 21F
Experience the Ultimate Waikiki Friday Night Delight!Welcome to your front-row seat to one of Honolulu’s most beloved traditions—the dazzling weekly fireworks lighting up the tropical sky. From your private lanai, sip a handcrafted cocktail, feel the gentle trade winds,...
Mountain Retreat - Waikiki 27F Suite Free Parking
This high floor one bedroom is comes with a private lanai and a complementary parking. The 27th floor unit comes with great mountain views and is one block away from the world-famous Waikiki Beach! Included: Fast free wifi, TV, central AC, full kitchen with appliances,...
Waikiki Mountain Breeze Retreat 2601B
At the beginning of Waikiki, the tourist center of Honolulu. Our charming studio in Waikiki is a breezy unit in Hawaiian Monarch buildingEnjoy breathtaking Mountain View. Hotel quality sheets, pillows, and air conditioning await you.Excellent location right across from...
At the beginning of Waikiki, the tourist center of Honolulu. Our charming studio in Waikiki is a breezy unit in Hawaiian Monarch buildingEnjoy breathtaking Mountain View. Hotel quality sheets, pillows, and air conditioning await you.Excellent location right across from...
Waikiki Horizon Retreat – Corner Ocean Views 19F
At the beginning of Waikiki, the tourist center of Honolulu. Our charming studio in Waikiki is a breezy unit in Hawaiian Monarch building.Enjoy breathtaking Ocean views. Hotel quality sheets, pillows, and air conditioning await you.Excellent location right across the...
Waikiki Ocean Oasis Retreat 37F
At the beginning of Waikiki, the tourist center of Honolulu. Our charming studio in Waikiki is a breezy unit in Hawaiian Monarch building, with City/Ocean view, small refrigerator, microwave, AC and Wifi; ideal for 1 or 2 guests. About 10 min walking distance from the...
Chic Downtown Honolulu Retreat – Free Parking
Experience Honolulu in style from our 15th-floor one-bedroom suite! Sleep soundly on a King bed or cozy up on the sofa bed, perfect for 4. Free WiFi and cable for endless entertainment. Walk to Walmart, Ross, and 7-Eleven. Dine at top spots nearby. Unwind in the large...
Couples Retreat - Getaway to Turtle Bay
This condo is a legal vacation rental located in a resort-zoned master community plan & also serves as our family's vacation home. We'd love to share it with you! Just a few minutes walk to the resort, beaches, golf, restaurants, horses & turtles.PER HAWAII STATE LAW,...
Malapua Hanalei - A Sweet Retreat TVNC#4268
New! *New photos soon!Welcome to Malapua Hanalei, a charming island retreat just steps from the best of North Shore living.Recently upgraded with new furnishings, beds, bonus room with ping pong table (new photos are forthcoming). Hale Malapua also known as “The Little...
Maui Resort Rentals: 6BR Retreat at Luana Garden Villas, Private Villas Only Steps from the Beach!
Nestled within the highly desirable Enclave Three of the Luana Garden Villas, this upscale 6BR haven combines two 3BR villas from two neighboring buildings to create over 4000 sq ft of interior living space, perfectly suited for larger groups or families. Located on 38...
This upscale 6BR retreat combines two 3BR villas from two neighboring buildings to create over 4000 sq ft of interior living space, perfectly suited for larger groups or families. Located on 38 beachfront acres within the popular Honua Kai Resort, your party will enjoy...
4BR I Kii Hale at Kukui ula Signature Retreat
Summary:Kii Hale at Kukuiula is a contemporary 4BR, 3BA residence offering a peaceful escape in one of Kauai’s most prestigious neighborhoods. With golf course vistas, a private heated pool, and open-air living spaces, this home invites relaxation in every corner. All...
Tropical Luxury Retreat W/ Infinity Pool, Spa & Outdoor Living!
Experience elevated Big Island living in this spectacular and serene island estate, ideally located within a premier resort setting. Picturesque bedroom suites feature private outdoor garden showers, creating a spa-like retreat surrounded by lush tropical beauty. The...
Waikiki Retreat ~ Steps to the Beach ~ Sleeps 4 ~ Free Parking ~ Full Amenities
Wake up to the sound of the ocean and step onto the beach in under a minute — this is Waikiki living at its finest. Nestled at 1765 Ala Moana Blvd along the beautiful Ala Wai Boat Harbor, this stylish 1-bedroom apartment comfortably sleeps 4 and puts you right at the...
Enjoy stunning ocean views from Kaanapali Shores 544, a 1-bedroom retreat in Lahaina.
Kaʻanapali Shores 544 Enjoy Ocean Views from this Updated 1 Bedroom North Kaanapali Vacation Resort Condo, Steps to the Pool, Hot Tub and Beach Welcome to Your Maui Retreat: Kaanapali Shores 544 is a newly refreshed 1-bedroom, 1-bath condo perched on the fifth floor of...
Waikiki 2-Bedroom Kaiulani Retreat | By The Ocean
*Important to note: if you're looking to book for longer than 30 days and the dates aren't showing as avaialble, please still reach out as the unit is likely available and we can assist in getting you booked for longer. Mahalo!*Settle into your own slice or paradise in...
Kauai Makanui 712 – Spacious 2BR/2BA Island Retreat for Relaxation Now
Welcome to Kauai Makanui 712, a bright and spacious 2-bedroom, 2-bath retreat. Thoughtfully designed for comfort and island living, this home is the perfect base for your Kauai getaway whether you’re here to explore the South Shore or simply relax in paradise.The...
Ohana Kai – Premier Luxury Retreat in Princeville
Welcom to Ohana Kai, Princeviile.Escape to your own private island retreat in the heart of Princeville, Kauai. This stunning 4-bedroom, 3.5-bath vacation home offers the perfect blend of tropical luxury, comfort, and space—ideal for families, groups, or anyone seeking a...
Paki Maui 222 Updated 2BD Direct Oceanfront Retreat Steps from Pool & Hot Tub
Paki Maui 222 Freshly Updated Oceanfront 2 Bedroom Condo in the Heart of West Maui with Ocean Views Steps to the Pool and JacuzziWelcome to your Maui Retreat: This freshly updated oceanfront condo at Paki Maui offers a relaxed, comfortable place to settle in and enjoy...
Waikiki Beach View Retreat ~ Steps to the Beach ~ Sleeps 5 ~ Free Parking
Wake up to stunning ocean views and step onto the beach in under a minute — this is Waikiki living at its finest. Nestled at 1765 Ala Moana Blvd along the beautiful Ala Wai Boat Harbor, this stylish 1-bedroom apartment comfortably sleeps 5 and puts you right at the...
Nestled on the tranquil hillside of the distinguished Mahinui neighborhood, Hale Kalia is nothing short of a refined sanctuary where modern luxury meets island serenity.Nestled along the tranquil windward coast of O‘ahu, the Mahinui neighborhood in Kāne‘ohe offers a...
Napili Shores D230 Studio Relaxing Garden View Retreat Near Napili Bay & Ocean
Napili Shores D230 Wonderful Studio On the West Maui Coast and Steps from Napili BayWelcome to Your Maui Retreat: A cozy studio condo nestled in the lush gardens of the beloved Napili Shores resort, just a short stroll from the golden sands of Napili Bay. Here, you'll...
Westin Kaʻanapali North 1BR Premium – Island Retreat
Discover your perfect Maui escape in this 1-Bedroom Premium Island View Villa at The Westin Kāʻanapali Ocean Resort Villas North. Offering approximately 750–900 square feet of space, this villa is ideal for couples or small families, with thoughtful details that make...
Kona Retreat • Ocean View, Pool & Walk to Beach
Welcome to your Downtown Kona Retreat! This top-floor 2BR/2BA condo offers ocean-peek views, a spacious lanai, and room for up to 6 guests. Enjoy a fully equipped kitchen, AC, pool, hot tub, and easy walkability to beaches, shops, and restaurants. Relax after a day of...
Honua Kai 825 3BD Oceanfront Retreat w/ Lanai, Floor-to-Ceiling Views & Modern Kitchen
Honua Kai Hokulani 825 Spacious 3 Bedroom Condo at Honua Kai Luxury Resort with Amazing Ocean and Sunset Views Professionally managed by Maui Paradise Properties. Welcome to your Maui Retreat: A beautifully appointed 3-bedroom, 3-bath condo located right on the ocean's...
Rustic retreat with panoramic views at Pu'u O Hoku Ranch
Pu'u O Hoku Ranch offers a unique getaway for travelers seeking a rustic retreat. You can hike, swim, stargaze, and see a working ranch in action. Pu'u O Hoku is one of the few places in the islands where you can feel Hawaii as it once was. The Sunrise cottage is just a...
Maui Resort Rentals: Kaanapali Alii - 4BR Retreat with Ocean and Mountain Views!
Suite 241 is ideally situated within one of the resort’s most desirable interior columns, showcasing sweeping views of the Pacific Ocean, the island of Lanai, and the impeccably landscaped Kaanapali Alii grounds below. These captivating vistas extend effortlessly...
(P9B) 2Br Princeville Retreat, Pool, AC, Wifi
Two-Story Princeville Condo – Lanai, Pool & Near BeachesFeel the trade winds and unwind in this spacious two-story retreat in Princeville, where tropical breezes, lush surroundings, and island living come together in perfect harmony. This beautiful condo offers a...
Royal Kahana 1010 2BD Coastal-Luxe Oceanfront Retreat w/ Lanai, AC & Stunning Maui Views
Royal Kahana 1010 Enjoy Epic Sunsets from this Stunning 2 Bedroom West Maui Oceanfront Retreat Welcome to your Maui Retreat: Royal Kahana 1010 is a stunning tenth-floor corner residence where uninterrupted ocean views stretch from the golden coast of Ka'anapali to the...
Kahana Sunset B4B Oceanfront Retreat w/ Sunset Views, AC & Private Lanai
Kahana Sunset B4B Spectacular West Maui Sunset Views, Steps from the Pool and the BeachWelcome to your Maui Retreat: Welcome to Kahana Sunset B4B, a beautifully remodeled 1-bedroom, 1-bath hideaway nestled in the boutique beachfront enclave of Kahana Sunset along the...
Westin Kaʻanapali North 1BR Premium – Island Retreat
Discover your perfect Maui escape in this 1-Bedroom Premium Island View Villa at The Westin Kāʻanapali Ocean Resort Villas North. Offering approximately 750–900 square feet of space, this villa is ideal for couples or small families, with thoughtful details that make...
Spacious Ground Floor Maui Retreat, Grand Champion
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...
Oceanview Retreat – 2 Side-by-Side Condos!
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...
Perfect for Romantic Retreat! Spacious Oceanfront Suite w/ Pool Access
Step into paradise: Explore Kanaha Beach Park & indulge at Queen Kaahumanu Center, right from our welcoming Kahului Bay doorstep.This listing is for a room within a hotel.✦ Your room is 588 sq. ft, equipped with complimentary toiletries, high definition 32-inch TV,...
Luxe Maui Beach Retreat Walk to Kamaole Beach
Summary:Prime Location Steps to Kamaole Beach dining shops Luxury Comfort King bed memory foam sofa bed Resort Perks Pool hot tub outdoor grills Entertainment 65 Smart TV free Netflix fast WiFi Seamless Stay Self-check-in Smart Lock Exclusive Perks 1000 in local...
Beach Bliss Retreat | Walk to Surf & Dining
Summary:Steps to the Beach Charley Young Kamaole 1 nearby Prime Location Walk to top restaurants shops Fast WiFi Smart TV Spacious Stylish Modern decor cozy ambiance Luxury King Bed Guests rave about comfort Resort Perks Pool hot tub BBQ tennis courts Free Parking Fully...
Beachside Retreat | Walk to Shops & Dining
Summary:Walk to the beach shops top restaurants Stunning garden lanai perfect for coffee wine Ultra-comfy queen beds for a restful sleep Resort-style pool hot tub BBQ area Smart TV high-speed WiFi for entertainment Free parking for hassle-free stays Beach gear included...