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.
Pualani Villa by Gather: Luxe Princeville Retreat w/ Pool & Hot Tub
Escape to Pualani Villa by Gather, a stunning three-bedroom + den, 2.5-bathroom townhome in the heart of Princeville’s prestigious resort community. Offering a beautifully designed living space, this two-story retreat combines modern luxury with island charm, creating...
Cozy Tropical Retreat Guest House with AC
Our Tropical Retreat Guest House is a luxurious 1 bedroom, 1 full bath resort-style guest house located in one of Hilo’s premier subdivisions. Our guest house is truly a tropical paradise with a very spacious living area. The guest house opens up to a beautiful...
Kona coffee farm retreat, with full ocean views near Kailua Kona!
Escape to a lush and secluded mountain retreat Kona coffee farm, just minutes away from sun-kissed beaches, Kailua and Captain Cook. Enjoy picturesque sunsets and stargaze at night. Relax in peaceful moments surrounded by full ocean views, exotic flowers, coffee trees...
Luxury Waikoloa Retreat: 3BR, Hilton Pool Pass!
Welcome to this spacious 3-bedroom townhome, perfectly located in the heart of Waikoloa Beach Resort. With lush landscape views, a short walk to the beach, and complimentary Hilton pool passes, this home offers the ideal setting for your island getaway. Accommodating up...
Serene Kauai South Shore Retreat, Full A/C, Walk to Beaches
The moment you step out to the private lanai and take a deep breath, the mind is instantly reset by birds chirping in the trees and the tropical foliage all around. You will appreciate the quiet and secluded vibe, yet with easy access to beaches, shops, restaurants....
Surf Hale, Elegant and Luxurious Surf Retreat
Escape to the breathtaking beauty of Princeville, Kauai, and immerse yourself in the ultimate experience that is Surf Hale. Welcome to our luxurious four-bedroom, 2 1/2 bath vacation rental, where paradise meets comfort and adventure awaits at every turn.Nestled within...
Exclusive, Dream Family Vacation Retreat.
The Royal Palms Estate is perfect for multi-generational families, friends, and groups of fewer than 12 people. Unfortunately, we can not have large weddings or parties. The Royal Palms has 13 Acres Of Exotic Fruit Trees, Tropical Foliage, And Palms. There is 9500...
Gorgeous Gated Retreat Near Ocean w Pool & Deck!
Enjoy a blissful vacation at the Heavenly Hawaiian Paradise Beach House. This 3BR/2BA retreat is perfect for groups up to 10, offering welcoming spaces both indoor and outdoor to dine and relax in the beautiful Hawaiian weather. Spacious outdoor deck with swimming pool,...
Ho'olei Villa 17-1: Luxury Retreat with Breathtaking Ocean Views
This property is hotel zoned, and not being affected by the recent proposed legislation.Luxury at its finest! Ho'olei Villa 17-1! Mesmerizing ocean views and bright open floor plan welcome you. Enjoy the beautiful Maui sunsets on your expansive private lanai.One of the...
Poipu Tropical Retreat with A/C & Pool/Gym Access
Discover beautiful Kauai from this spacious 1 bedroom vacation home (built in 2018) in the heart of sunny Poipu. Located in Poipu Beach Estates, the newest upscale neighborhood bordering the Kiahuna Golf Course, that is just minutes from the best beaches on Kauai,...
Romantic, Luxury, Sensual Retreat - Couples Only
Welcome to The Palms at Wailea – Your Island Paradise Awaits! Located in the prestigious Wailea resort community, The Palms at Wailea condo complex stands out as one of Maui's most elegant destinations. Our 1-bedroom, 2-bathroom condo (Unit #1603) has been custom...
Pristine Hawaii Retreat with Ocean, Golf & Palm Tree Views. Top corner unit!
Feel at home in this gorgeous corner, top floor villa in the Hali'i Kai oceanfront development in upscale Waikoloa Beach Resort. This fabulous 2 bedroom villa is perfect for 4 adults (plus one child with owner approval).Enjoy your morning coffee on the lanai, taking in...
Lani Paradise - Oceanfront Retreat with Private Pool
Discover paradise with a private pool, surrounded by natural oceanfront scenery. Revel in the charm of this tastefully decorated 4-bedroom, two-story Villa and romantic 2-bedroom Cottage overlooking Maui's North Shore.This exclusive property offers private waterfront...
Hale Kamaole 112 Romantic Beach Retreat/ King Bed/ A+ Internet
Hale Kamaole: Romantic Bright & Airy Beach Condo ACROSS THE STREET from Kamaole III Beach in South Kihei! Tasteful heritage decor, fast internet, King bed, walk-in shower, 1st floor unit. Perfect for couple's getaway, anniversaries, brides & honeymooners. Spacious lawns...
A Blissful Retreat in the Heart of Seaview - 5 minutes from the beach!
Kitsune Cottage: Your Oceanfront Oasis in the Heart of Seaview.Welcome to Kitsune Cottage, where the beauty of the Hawaiian islands meets the comfort of home. Nestled on the Hilo side of the Big Island, our cottage offers an unforgettable retreat, with cozy charm,...
Mountain View Retreat Unit 1 - highly rated on leading rental sites!
Peaceful rain forest guest house a few miles from Volcano National Park. Mountain View Retreat is located in a lush and relaxing paradise. Enjoy your coffee or tea in the morning on your own private lanai. For larger parties there is another guest house on the same...
5 Minutes to the Beach! Oahu Ocean View + Family retreat
☆ A luxury-style escape without the resort price ☆ Private 9-seat hot tub for relaxing soaks under the stars☆ Pool & Spa: Brand new Ocean-view community pool in a quiet, gated neighborhood☆ Outdoor Bar and grill in private backyard and 10-seat dining table for...
Poipu Luxury Farmhouse: NEW Estate with Access to Pool & Pickleball
Welcome to our Luxury Farmhouse, perfect for large groups or families. Just a half mile from the beach, this property features 5 bedrooms, 4 baths, 2 family rooms, and 1.5 kitchens. Enjoy open shared spaces, private lanais, well-equipped kitchens, spacious baths, A/C...
Heavenly Hawaii Retreat Home near Hilo, Ocean & Waterfalls
Welcome to the perfect Hawaii Homebase for you & your family-friends! Enjoy tons of space and privacy in this gorgeous, pet friendly, 4BR/2BA fully appointed home on a five acre fruit farm, designed for up to 13 guests. This retreat offers ocean views, various indoor &...
Luxurious 3BR Retreat in Poipu Kai Resort with Pool, Elevator, & Beach Access
Kauai’s Luxury Tropical Retreat in the heart of Poipu Kai Resort!Located on the beautiful island of Kauai, this 3-bedroom, 3-bath unit offers the highest level of luxury in the Poipu Kai Resort area. These amazing accommodations feature 2 King primary suites and an...
*NEW Poipu 2BR Retreat|Pool|AC & Athletic Club
Discover luxury in the serene Poipu Beach Estates with our charming 2br/1ba cottage. Enjoy farmhouse-inspired design, full kitchen with KitchenAid appliances, and quartz countertops. Relax in A/C-cooled bedrooms or on the lanai. Exclusive access to Poipu Beach Athletic...
Island Oasis: Stunning Ocean View Retreat! Heated Pool, Spa, AC & Putting Green
Island Oasis by Gather is located in one of Kailua-Kona's most coveted gated subdivisions, Keauhou Estates. This ocean-view Kona vacation rental home offers unparalleled views of Keauhou Bay, Kona, and grandiose sunsets year-round. Take a pause and ponder the...
@ Marbella Lane -Coastal retreat near Diamond Head
Summary:Enjoy this tastefully decorated studio with lots of natural light and cool ocean breezes. This unit has a private lanai, great for enjoying your morning coffee or afternoon tea, and has a great view of Diamond Head, Kapiolani Park and across-the-street water...
Unforgettable Luxury Awaits: Hokulani 310 - Modern Retreat with Ocean Views!
Special Offer for Extended Stays!Escape to the islands this fall and enjoy exclusive perks designed to make your stay even more relaxing:-No Resort Fees-No Parking Fees-Complimentary Mid-Stay Clean for stays of 14 nights or moreWhether you're planning a quick getaway or...
🏝️ Maui Oceanfront Wellness Affordable Penthouse Retreat! Oh the views! 🐋
Oceanfront Bliss at Hololani – Top-Floor Corner Unit Penthouse in Kahana, Maui | 2BR | Breathtaking Views | Walk to Beaches & DiningWelcome to your Oceanfront Maui Penthouse — a serene top-floor corner unit with breathtaking panoramic views of Lanai and Molokai....
Puako Tropical Garden Retreat · Puako Tropical Garden Retreat - Across from Beach!
Your Ideal Puako Beach Retreat – New Air Conditioning Installed This perfect Puako beach home features 3 bedrooms and 2 ½ bathrooms, ideal for families, couples, or friends traveling together. Located just steps from a secluded beach entrance, you'll enjoy peaceful...
Mauna Kai Retreat: Shops, Restaurants, and Beach!
Looking for a relaxing escape that offers it all? Look no further. This stunning property is within easy walking distance of the Princeville Shopping Center, offering everything from hiking trails and beautiful beaches to delicious dining adventures.Property...
Sunset Beach House – Polynesian-Style Beachfront Retreat
A Note About The $1,150/nt Rate: It is calculated as $1,350/nt with a 15% discount that brings it to exactly $1,147.50/nt. Please note, It is only for dates that are very close to the current date that I have not been able to book so I lower the price to encourage...
4-Bedroom Retreat Near Magic Sands Beach with Outdoor Living & Beach Gear
Escape to this stunning 4-bedroom, 2-bath home where contemporary design blends seamlessly with island-inspired decor. Nestled in the desirable Magic Sands subdivision, just beyond Alii Drive, this home offers an inviting open living space and lush landscaping, making...
Gorgeous Oceanfront Retreat! Marvel at the Stunning Views from Sugar Beach #326n
Welcome to Sugar Beach Resort #326 – Gorgeous Oceanfront Retreat!Experience the serene beauty of North Kihei at Sugar Beach Resort, a picturesque beachfront condominium resort offering breathtaking Pacific Ocean views. Two six-story buildings, equipped with elevators,...
Beachy Boho Retreat in the Heart of Kihei – Steps to Beach!
Ready to get away from it all? Say aloha to this beautiful beach side retreat in easygoing Kihei, ready for you and your guests to enjoy the fun, sun and experience why ‘Maui no ka ?oi’! Just across the street from the beach, this 2 bedroom, 2 bath condo sleeps up...
Molokai Island Retreat w/ Ocean View & Pool!
Venture to the picturesque island of Molokai for a solo trip or romantic getaway. Discover the tallest sea cliffs in the world, lush hikes to Kalaupapa and Halawa Valley Falls, sport fishing, and colorful reefs perfect for snorkeling when you stay at 'Blue Marlin', a...
Luxurious 3BR/3BA Retreat with Private Beach Club Access in Mauna Lani
Summary:Escape to paradise at this luxurious townhouse in Mauna Lani Resort, perfect for families! This spacious 3-bedroom, 3-bathroom home with a loft comfortably sleeps 8 and offers resort-style amenities. Enjoy the exclusive gated community of Mauna Lani Palm Villas,...
M. KoOlina Beach Club Oceanfront Resort, Beautiful, Tropical Oceanfront Retreat!
Please choose a Friday through Sunday check-in for a seven night stay. Rates are based on a garden view and will fluctuate for holiday weeks. Thank you for your interest in booking with Dash Realty Group, Windermere Florida. Dash Realty Group is registered in Florida as...
Eastside Zen Retreat, Pono Kain4/25-5/3 - Discounted 15%
Without a doubt, the Pono Kai Zen Retreat is the finest unit on this 15 acre property. This 2 bedroom 2 bath condo is literally only steps to the warm Pacific Ocean! Golden sunrises, warm trade winds, and shimmering waters next to a mile-long sandy beach. Those are just...
Island retreat with a pool, BBQ access, private lanai, washer/dryer, central AC
Kauai Kailani 109Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Aloha paradise! This beautiful Kauai Kailani property features all of the amenities you love to have while on...
Natural Light End Unit Kuilima East Steps to Pool-BBQ-Parking Golf Retreat
Book with confidence! This property is professionally managed by Ali'i Beach Rentals, an award-winning property management company.This property is a new addition to our inventory. Rest assured, we can confidently say that this property is truly amazing.Welcome to this...
Escape to paradise at Mauna Lani B208, an exceptional oceanfront retreat
Mauna Lani B208 Oceanfront Vacation Rental – 2 Bed, 2.5 BathEscape to paradise at Mauna Lani B208, an exceptional oceanfront retreat offering unparalleled luxury and breathtaking views. This stunning 2-bedroom, 2.5-bath condo is situated in one of Hawaii's most...
Pua Oriana: A Polynesian Tropical Retreat
E komo mai — welcome to our hale. Welcome to the Pua Oriana – a mix of Hawaiian and Samoan language, ‘pua’ meaning flower, and ‘oriana’ means the flower that adorns a woman’s head. Enjoy the space and the grounds with 880 acres of pristine gardens, walking...
Stunning Oceanfront Retreat with Spectacular Views and New Upgrades!
SPECTACULAR!! HIGHLY desirable third-floor condo!! Enjoy beautiful, unobstructed, panoramic ocean views from your own spacious and private lanai. Listen to the gentle sounds of the ocean at this DREAM get-away.Unbeatable location right on the water. View the tropical...
Hale Malie - a peaceful rainforest retreat minutes from Volcano National Park!
Hale Malie is a charming 1-bed/1-bath cottage retreat on a private half acre of lush Hawaiian rain forest just minutes from Volcano National Park. Featuring vaulted ceilings, a full kitchen, a sunny dining area, and expansive covered lanai, this cottage is ideal for two...
Waterfront retreat w/ a furnished balcony, incredible view, & a shared pool
Kona Bali Kai #205Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Paradise awaits at this two-bedroom, oceanfront, Kailua-Kona condo. Offering a variety of desirable amenities,...
Deluxe Ka'anapali Condo with AC Luxurious Retreat
**Kaanapali Plantation #16 – Your Peaceful Island Getaway**Welcome to Kaanapali Plantation #16, your serene island retreat with expansive views of lush landscapes, the Royal Kaanapali Golf Course, and the islands of Lanai and Molokai, all framed by the stunning blue...
Private Hidden Retreat On North Shore Near Beach!
Discover Ha‘ena Place | North Shore Kaua‘iNestled on a quiet cul-de-sac, Ha‘ena Place is a true hidden gem—just a short stroll to some of Kaua‘i’s most iconic North Shore beaches, including Tunnels (Makua), Ke‘e, Lumaha‘i, and Hanalei Bay. Whether...
Mountain-view retreat with 2 suites, pool & hot tub - near restaurants & beaches
Villas of Kamali'i Apt 20Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'At the Villas of Kamali’i 20, you get it all - a convenient, split-level floor plan, gorgeous finishes, and...
Private Island Retreat. Tropical Sanctuary.
UALANI RETREAT Fully Licensed & Permitted. Locally Owned & Operated B&B BBPH 2012/0002 SUP2 2012/0001Terrific Discounts Thru October. Private detached 1 bedroom cottage on 3 acre tropical retreat. Lush haven surrounded by fruit trees and bamboo groves. Nicely equipped....
Maile Hale: Private Oceanview Retreat w/ AC, Near Beaches & More
Experience a Hawaiian getaway like no other in this private, ocean-view retreat located in the prestigious, gated Keauhou Estates community. Just minutes from the beach, restaurants, shopping, and a variety of island activities, this three-bedroom, two-bath home away...
Luxurious Beachfront Retreat
Experience paradise at Hale Maluhia, an exclusive beachfront home on the idyllic Hanalei Bay. Perfect for honeymooners or small groups seeking a luxurious escape, this stunning property offers unparalleled privacy within a gated enclave.Indulge in the epitome of comfort...
Kehena Beach Oceanfront Retreat - Incredible Views of Ocean from Every Room
Discover the ultimate oceanfront retreat on the Big Island at Kehena Cliffside Estate — a private, gated luxury rental designed to showcase breathtaking views of the Pacific Ocean from nearly every room. Nestled along the dramatic cliffs of Kehena, this spacious...
Haena Beach House – Luxury Oceanfront Kauai Retreat
TVNC 1258Haena Beach House offers a once-in-a-lifetime vacation experience, providing contemporary luxury in a private beachfront setting. Ideal for large groups, the home showcases breathtaking panoramic views of the Pacific from its living spaces and each of its...