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.
Oahu North Shore 2 BR Oceanfront Retreat at Sunset Beach
Escape to the stunning shores of Haleiwa and experience the ultimate beachfront getaway at our charming vacation rental. Nestled along the pristine sands and turquoise waters, this slice of paradise offers an idyllic setting for relaxation, adventure, and unforgettable...
Kalo Homes ~ Sunset Retreat
Where adventure meets relaxation: a gated valley retreat with room for the whole family, Makaha Beach just minutes away, and mountain views.Escape to our tropical getaway in the exclusive Mauna Olu Estates, just two miles from world-famous Makaha Beach. Perfect for...
Laule'a 11: Mauna Lani Luxury Retreat with Private Pool & Spa
Experience luxury island living at Laule‘a at the Mauna Lani Resort #11, an elegant 4-bedroom, 4.5-bath retreat nestled within the prestigious Mauna Lani community on the Kohala Coast. This stunning home combines contemporary Hawaiian design with world-class amenities,...
Kona Makai 6303: Tropical Retreat 1BR w/ Ocean Views, Pool & Gym
Perched on the top floor of the beloved Kona Makai community, Kona Makai 6303 is a remodeled 1-bedroom, 1-bathroom oceanfront condo with a bonus loft. Featuring sweeping ocean views, breezy lanai dining, and resort-style amenities, this retreat is perfect for couples or...
❤️PiH❤️ Sun Ray Retreat ★Ocean & Sunsets Views★Optional Mauna Kea Hotel Privileges
Brought to you by Paradise in Hawaii Luxury Homes.Welcome to Sun Ray Retreat, a part of our Hawaiian Luxury Collection. Sun Ray Retreat at the Mauna Kea Resort Kumulani complex has stunning views of golf, ocean and sunsets. This three bedroom upper-level unit is...
5 Minutes to the Beach! Oahu Ocean View + Family retreat
☆☆☆ Why guests LOVE our home? Why guests find it such a great VALUE?- Free parking for 5 cars (save $40–$100/car nightly)- Private SPA & BBQ in backyard, full kitchen to cut dining costs, - Spacious single-story for large family with senior and kids, 3 bedroom, 9 beds...
Steps to Beach at Maui Banyan-resort style amenities-AC, WIFI, Full Kitchen
Cozy 1BR Condo in the Heart of Kihei – Walk to Beach!Escape to sunny Kihei, where this charming one-bedroom condo puts you just a short walk from Kamaole Beach Parks 2 & 3—perfect for sunbathing, swimming, and catching breathtaking sunsets. With beach gear provided...
Oceanview Luxury Estate - Multi-Suite Retreat in the Kona Uplands in Holualoa
Luxury Oceanview Estate – 2 Suites + Cottage + Additional Bedroom | Infinity Pool | Gym | High-Speed Wi-FiWe are a 3 Acre Luxury Vacation Rental Property with an Award Winning Coffee Farm comfortably nestled on the slopes of Hualalai overlooking Kailua-Kona.We offer...
Central tropical streamside retreat $0 CLEANING FEE. Ask about shorter stays.
Our clean, tropical streamside home is perfectly situated to explore the entire island. Wake up listening to birds chirp and the stream flow. Explore for the day on the North Shore, West Side, Waikiki, East Side or just relax and use it as your paradise home. Our 3 bed...
Tropical Wailea Retreat
We invite you to come and stay at our spacious suite where you can enjoy the exclusive Wailea lifestyle. Relax & restore in this serene space surrounded by tropical palms!This bright and airy 1 bed/2 bath, corner end unit is a modern Hawaiian retreat. The suite features...
Beachfront Molokai Sanctuary Romantic Getaway Writers retreat Solo Rejuvenations
3 Minute walk to the Beach! Hawaii as you imagined it 50 years ago! Breathtaking beaches only steps away in a serene, uncomplicated paradise of days gone by. Sparkling ocean views from the airy screened in lanai with only the sounds of waves at night and tropical birds...
Rainbow Retreat - Ocean Front - Molokai - Peaceful
*MOLOKAI - NOT MAUI*Here at Rainbow Retreat, we take your comfort extremely seriously. From the Cozy Earth bamboo bedding (Oprah's favorite, 5 years running) to the quality furniture and design you will sink into and enjoy the quiet.Comfortable, minimalistic...
Kehena Moana Kai - Amazing OCEANFRONT Private Retreat
Perched in the sunbelt at the edge of a dramatic oceanfront sea cliff, this honeymooner’s paradise sits in the heart of the lush Puna District rainforest on the Big Island of Hawaii. With two air-conditioned bedrooms, this private cliff house retreat accommodates up to...
Stunning Ocean View Penthouse Unit! Quam Properties Hawaii
Kaanapali Shores 905 one-bedroom penthouse featuring amenities such as a magnificent ocean view, comfortable seating area, and a private lanai. The condo can accommodate up to 4 guests with a king-size bed in the bedroom a queen sleeper sofa and a twin sleeper sofa in...
2 Bed Maui Retreat with 5 miles of beach!
Kanai A Nalu, what a gorgeous beach front condo! It's a great remodel with tile flooring throughout, island-style furniture, and a stunning kitchen with a full-size front load W/D! All the comforts and conveniences of home, but it's in paradise! With 2 bedrooms, one...
Hanalei Plantation Road Home - Dream Retreat with Pool & Ocean Views
Escape to this beautiful Hanalei Plantation Road home, nestled in a prized neighborhood. Enjoy sweeping mountain and ocean views over Hanalei Bay. With 4 bedrooms, a gym, pool, and ample indoor/outdoor space, it's a dream retreat. Upstairs, find a bright living/dining...
Stunning tropical retreat near the beach with pool, views & spacious lanai
Ho'oka'ana HaleOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Live the luxe life at the top of Alii Heights! Surrounded by colorful blooms and palm trees, find yourself waking up...
Cool retreat at the entrance to Lanikai-Very Close to Beach-3 Primary Bedrooms
Live your best life! An opportunity for beach living in this renovated and updated luxury rental with views of Kailua Beach and Kailua Beach Park - it's brilliant turquoise blue ocean, sandy beach, large grassy areas and tall ironwood trees. Fine craftsmanship abounds...
Paia Bay House: 4BR Oceanfront Retreat on Maui's North Shore
Attention, the State of Hawaii Transient Accommodation Taxes has been recently increased to 11% for all 2026 reservations. Confirmed reservations will see an invoice adjustment when the new tax law is signed by the Governor.Oceanfront property in the heart of Paia town,...
Spacious Lanai Retreat: Kapalua Maui's Golf Villa with Breathtaking Views 14T 1-2
This is a legally permitted vacation rental according to the County of Maui ordinances.Spacious Lanai Retreat: Kapalua Maui's Golf Villa with Breathtaking ViewsImmerse yourself in the epitome of luxury with our recently refurbished 1-bedroom, 2-bathroom condo, nestled...
Relaxing Gardens - Peaceful Retreat w/Panoramic Ocean Views
Welcome to our private, peaceful retreat on Hawaii Island's Hamakua Coast - Relaxing Gardens. Unwind and enjoy the panoramic ocean views from our home atop a hill in Laupahoehoe, Hawaii. Our lush gardens will delight your senses with color, fragrance and even a few...
New to VRBO. Air Conditioned Luxury Island Retreat - Newly Remodeled
Newly remodeled ground-floor condo at Alii Kai with all new fixtures and furnishings.Located on the cliffs above Turtle Cave, you are just steps away from a private path leading to snorkeling with Kauai's magnificent Sea Turtles. Enjoy ocean views from the front porch...
Rainforest Retreat w/Outdoor Fireplace & Hot Tub
Located 10 minutes from Volcanoes National Park, come spend your days exploring, hiking, golfing or simply relaxing in our unique, tranquil setting. This beautifully crafted home has all of the amenities and comforts you need. From soaking in the large hot tub to making...
Beautiful 3 Bedroom Rainforest Retreat, minutes from HVNP
Come and enjoy our beautiful retreat, just minutes from Volcano Village and the world renowned Hawaii Volcanoes National Park. Designed by renowned local architect, Boone Morrison, this unique property features lots of natural wood and light, providing a wonderful...
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...
Breathtaking Oceanfront 5 bedroom - Puamana 150-1
Aloha and welcome to your Maui oceanfront dream home—Puamana 150-1.This spectacular front-row oceanfront townhome sits just 30 feet from the water’s edge in the exclusive, gated Puamana community. Recently remodeled and tastefully furnished with a relaxed beach-surf...
Sunset Suzy's tropical retreat! One free night! After 7 nights.
Sunset Suzys Tropical Retreat is located perfectly 15 minutes outside of Hilo town in a beautiful neighborhood called Hawaiian Paradise park.. It is located on a beautiful one acre lot, filled with fruit trees, green grass, green geckos, and tropical birds. There are no...
Kailua Beachfront Vacation Home with Pool
This property is professionally managed by Private Homes Hawaii, LLC and is licensed as a short term vacation rental, Non-Conforming Use Permit Number 1990/NUC-1783. It is compliant with Hawaii State Legislation (HB2078) for vacation rental accommodations,...
Comfortable, single-level retreat with fast WiFi & washer/dryer - dog-friendly
Puni Mauka A | 31-Day MinimumOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Located less than five miles from Pāhoa for convenient shopping and dining and just two-and-a-half miles...
Tropical designer retreat right on the water with ocean view, pool & AC
Puu Poa 101Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Spend your vacation enjoying the salty sea air and ocean views from the spacious lanai and nearly every room inside this...
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...
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....
🏖️Sophisticated Oceanfront Retreat | Air-Conditioned | Walk to Beach | vrKCV
vrKCV - The Kona Hideaway at Kona Onenalo No. 11, Professionally Managed by Kona Coast VacationsThe Kona HideawayDiscover the essence of Hawaiian living at The Kona Hideaway, a private oceanfront villa nestled in the exclusive gated community of Kona Onenalo. Adjacent...
Luxe retreat with hot tub and pool access, private W/D, grill, AC, & gas range
Hale HaupuOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Welcome home to your tranquil Hawaiian getaway! This newly-constructed upscale home is nestled in a quiet neighborhood away...
Lodge at Kaloko - Kona Cloud Forest Estate with Pool & Hot Tub
The Lodge at Kaloko – Luxury Estate in KonaPrivate 5BR villa | Pool | Hot tub | Ocean views | Near Kua BayWelcome to The Lodge at Kaloko, a luxury gated estate in the lush Kona Cloud Forest — just 15 minutes from Manini‘owali Beach (Kua Bay), downtown Kona, and the...
Molokai Island Retreat Wavecrest- Ocean Views
Aloha and welcome to Molokai Island Retreat! Molokai Island Retreat is located on the highly desirable lush east end of Molokai (we are not on Maui) in the Wavecrest Resort. Our condo offers a breathtaking bird’s-eye view of the ocean, with stunning vistas extending all...
Hawaiian Chic Crater Retreat- a tropical jungle escape in a secluded crater
***FYI- swimming pool will be closed April 15th-May 15, 2024 for repairs***Being on the ocean is amazing, but is it as amazing as having a one of a kind condo in a secluded crater? It has many of the same amenities as a $1000/night nearby resort does, for a much better...
Maluhia Makai - Luxe Kukui'ula island retreat in Poʻipu; AC, private heated pool
This luxury home is 2200 ft.² of air-conditioned space that opens up to 1000 ft.² of an outdoor living lanai. The design of this home seamlessly marries the indoors & outdoors together to make a grand tropical outdoor experience. Pass through its custom entry wood gate,...
Spacious 2BR Poipu Retreat w/ AC, Lanais & Resort Amenities
E Komo Mai — Welcome to Mala Pua Regency 610!Discover your perfect island retreat in this beautifully appointed 2-bedroom, 2-bath ground-floor condo located in the heart of sunny Poipu. Designed for comfort and relaxation, the open-concept living space features two...
'The Aloha Green House' Retreat w/ Ocean Views!
The ultimate Hawaii getaway awaits at this 2-bedroom, 1-bathroom vacation rental apartment with sweeping views of the Pacific. Ideally located between Kona and Hilo, this home-away-from-home provides easy access to popular areas such as Hawai'i Volcanoes National Park...
Trivett Oceanfront Estate: 5BR Luxury Retreat in Kailua-Kona
STVR- 19-365146NUCR 20-1787TMK - (3) 7-5-005-096GE/TAT - 051-694-0288-01Transcend paradise with our absolute oceanfront 3 story 5 bedroom home located only blocks to Kailua-Kona town and within a guarded gate community of luxury estates. Your private oceanfront setting...
Kilauea Lakeside Estate - Secluded Luxury Retreat on Private 4-Acre Peninsula
This totally private resort has been described as the best private Kauai retreat in the Hawaiian islands. Located in a wildlife refuge on its own private lake on the island of Kauai, Kilauea Lakeside Estate is a beautifully secluded Hawaiian retreat, simply perfect for...
Lani Oasis - Princeville Vacation Home with Saltwater Pool
Lani Oasis welcomes you with its serene ambiance and tropical charm, perfectly situated in beautiful Princeville, Hawaii. This luxurious villa is designed for both relaxation and recreation, featuring a private saltwater pool surrounded by lush gardens and inviting...
Sugar Beach Resort 333: Ocean Front retreat with relaxing coastal décor.
Ocean Front retreat with a cool ocean breeze and coastal decor. You will feel relaxed from the moment you enter this one-bedroom ocean-front condo. The bedroom has a king bed, allowing this condo to accommodate up to two guests. The kitchen is fully equipped with...
Spacious 3 Bed 2.5 Bath House in Kahakai Estates
Experience island living at its finest in this beautiful and modern 3-bedroom, 2.5-bath home located in a quiet, gated community just minutes from downtown Kailua-Kona. Enjoy easy access to beaches, shopping, and restaurants—then return to your private oasis complete...
Endless Ocean Views from your Sugar Beach Retreat -Central AC #208
Come enjoy the amazing ocean views and breathtaking sunsets in our updated deluxe one bedroom, one bath, air-conditioned condo. Sugar Beach Resort, is just steps away from the 5-mile white sandy beach. Our beach access is excellent for swimming, snorkeling, windsurfing,...
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...
Vehicle to Rent, Hilton Pass, BBQ on lanai, Sleeps 6, L23
Bookings through 2025 will receive a special welcome bottle of bubbly & Mac Nut Chocolates to enjoy Hawaii from your first moments. We stock our condo with everything — not just a”starter kit”. This gorgeous 2 bedroom, 2 bathroom home has 1,209 square feet with...
Magic Sands Retreat: Remodeled Cottage,Walk to Beach, Incredible Location,AC!
The Magic Sands Retreat is a quaint 3 bedroom/2 bath cottage just around the corner from the famed Magic Sands Beach and the Ali'i Drive beach corridor. Just a 10 minute walk to the most popular beach in Kona! This upgraded home shows attention to detail with an artists...
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...