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.
Ko Olina Kai #17: Spacious, Stylish Retreat with Golf Course Views
This property is offered as a monthly rental. Although full-month occupancy is not required, the monthly rate remains fixed and applies in full, regardless of the number of nights stayed, as prorated rates are not available.Ko Olina Kai Estate #17 by Gather, nestled on...
'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...
New Listing! Peaceful Poipu Retreat Waikomo 200
Experience the perfect blend of serenity and convenience in this beautifully updated one-bedroom corner unit at Waikomo Stream Villas. Nestled among lush Hawaiian foliage, this modern retreat offers a peaceful jungle atmosphere while being just steps away from Poipu's...
Ekahi Ocean Studio: Couples Retreat, Just 300 Feet To Keawakapu Beach
Ekahi Ocean Studio is a studio perfectly located in the lower village of Wailea Ekahi (#8C), a lush-landscaped paradise, just steps from the oceanfront pool and to world-renowned Keawakapu beach. This studio is perfect for couples seeking a peaceful, romantic retreat....
Ko Olina Kai Estate #20: Elegant Fairway Retreat with Luxe Amenities
This property is offered as a monthly rental. Although full-month occupancy is not required, the monthly rate remains fixed and applies in full, regardless of the number of nights stayed, as prorated rates are not available.Imagine yourself living the life of luxury in...
Peaceful Big Island Hawaii Retreat with Private Beach Club Access
Our home is a classic Hawaiian style bungalow (no shared walls) 3 BR / 3 Bath (2 master ensuite) with attached garage parking. It's a space to relax, recharge and enjoy "island time". We have beach cruiser bikes, beach towels, snorkel gear, and paddle boards for your...
South Kauai Tranquil Retreat w/ AC in Poipu
Waikomo Streams is a peaceful, tranquil, and beautiful property with immaculate gardens. Immerse yourself in a paradise garden view on the Garden Island! We have an updated, air conditioned unit that is quiet and comfortable. The property boasts tropical gardens, a...
Beachfront Retreat with Stunning Ocean Views at Hale Pau Hana on Kam II Beach.
Anchor Cove D2 is a single story property perched at the beachfront on the beautifully landscaped grounds of Hale Pau Hana Resort. Originally the resort restaurant, the building was reconstructed as a side by side duplex. Its prime location, large size, and proximity to...
Hale Ohana: Kailua Retreat w/hot tub, Tropical Pool, Walk to Beach
This property is offered as a monthly rental. Although full-month occupancy is not required, the monthly rate remains fixed and applies in full, regardless of the number of nights stayed, as prorated rates are not available.Hale Ohana meaning Family House is just that!...
Pu'u O Hoku Ranch Retreat
Pu'u O Hoku Ranch offers a unique getaway for travelers seeking a rustic retreat. You can hike, swim, stargaze, surf, 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...
Breathtaking 1 Bed True Oceanfront Retreat at Napili Point Resort in West Maui
Aloha, E komo mai (welcome) to Napili Point Resort Unit A13 in West Maui, Hawaii"You will absolutely LOVE this privately owned, Spectacular, 1 Bedroom Oceanfront Condo (A Unit) at the exclusive Napili Point Resort in Maui". - Actual quote from a guest. Bring your...
Relaxing 4-Bedroom Farmhouse Retreat on Working Farm
Situated on a 20-acre farm, Hale Makana Kamalei is an expansive 4-bedroom house with an open floor plan. Explore the island as locals know it.Discover the back orchard and enjoy fruits from more than 50 fruit trees, vegetables from our organic garden, and fresh eggs...
Beach Front, Pool, Amazing Sunrise! Welcome to Oceanside Retreat At Kapaa, Kauai
ALOHA! This 1st floor, updated unit has a private lanai to enjoy spectacular ocean views, stunning sunrises or perhaps an evening moonrise, if the time is right! This place has it all! The pool is just 20-feet from the lanai, and world-famous Waipouli Beach is only...
Kihei Beach Retreat: Ocean Views and Sandy Feet!
Experience Maui's charm in our 2-bed, 2-bath condo, directly managed by us for a personal touch. Just steps from top beaches and snorkeling, with stunning ocean and West Maui Mountain views. Enjoy our resort-style amenities including a pool, hot tubs, game room, and...
Walker's Lanikai Beach House – Historic Oceanfront Retreat
Welcome to Walker's Lanikai Beach House. John Walker, was a Scotsman who made his way to Hawaii as a young man in the 1870's to become a contractor of choice to Queen Liliuokalani, and erect such notable buildings as the Bishop Museum and Honolulu Hale (City Hall). Mr....
Lokelani B102 – Premium Oceanfront Retreat Steps from the Sand
Experience the Elegance of Oceanfront Living at Lokelani B102 – Your Private Maui EscapeStep into your dream Maui getaway at Lokelani B102, a fully renovated beachfront sanctuary offering uninterrupted panoramic ocean views just steps from your private lanai. Nestled...
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...
Tropical Retreat in Paradise-steps from the Ocean! Newly remodeled with A/C.
Beautifully remodeled ground floor corner unit in Building 20, with Pacific Ocean views! From the front Lanai, there is a broad green lawn, lined with palm trees that take you to one of the most beautiful swimming and surfing beaches in the world. Our one bedroom, first...
Our Place of Joy: An Ocean Retreat
Length of stay: MINIMUM 30 NIGHTS. Monthly rental. Property damage insurance required.Kai Lani is a quiet gated community located in Ko Olina, a 640 acre oceanfront resort on West Oahu, the dry leeward side of the island. Ko Olina means 'Place of Joy,’ where the aloha...
Escape to Paradise: Family Retreat in Princeville at Hanalei, Kauai.
Discover your family’s ideal getaway in the heart of Princeville at Hanalei, Kauai! Our spacious vacation rental offers a tranquil oasis surrounded by lush landscapes and tranquil gardens. Designed for relaxation and connection, this private home features:•...
UALANI RETREAT. Spacious Ocean/Mountain View Cottage.Private Tropical Sanctuary.
UALANI RETREAT Fully Licensed & Permitted Locally Owned & Operated B&B Permit # BBPH 2012/0002 SUP2 2012/0001Terrific Discounts Thru October. Enjoy your own PRIVATE DETACHED HOME at this lush tropical Hawaiian paradise. A refreshing place to nurture your spiritNicely...
North Shore Villa - Relaxed Luxury Retreat
Welcome to your peaceful retreat on Oahu's stunning North Shore, located in the desirable Kuilima East community. Nestled next to the luxurious Ritz-Carlton Oahu, Turtle Bay, and overlooking its world-renowned golf course, this charming vacation rental offers the...
NEW Listing - 1BD/1BA Retreat Ideal for Couples, Golfers & Business Travelers
Are you ready to indulge in an unforgettable escape on the stunning west coast of Hawaii Island? The Shores at Waikoloa Beach Resort beckons you to experience the tranquility and beauty of the Big Island. Nestled between two pristine golf courses, our gated condominium...
Spectacular Executive Beachfront Retreat
Waialua Retreat is your home away from home! Located on a quiet residential cul-de-sac, you will truly relax as you dine on the lanai of this spectacular, architecturally designed beachfront home, while taking in amazing sunrises and sunsets. Enjoy panoramic views of...
Oceanview Makaha Valley Retreat | Gated | Near Golf & Sandy Shores
Book with confidence! This property is professionally managed by Ali'i Beach Rentals, an award-winning property management company.May 2025 the Community Pool, Jacuzzi, and Gym are now OPEN!!Discover the peace and beauty of your own secluded retreat nestled in the...
Tiki Ali'i Retreat Su
Summary:Tiki Ali’i Retreat Escape to Tiki Ali’i Retreat, a serene Hawaiian getaway nestled in the oceanfront Ali’i Villas complex on the Big Island’s stunning west coast. This second-floor villa offers peaceful garden views, an inviting lanai, and a prime...
Peaceful retreat with sunset & ocean views on the Waikoloa Village Golf Course!
Modern luxury right on the Waikoloa Village Golf Course! Ocean and sunset views from the lanai and almost every room!! Our Hawaiian home was completely renovated in 2017, with a brand new kitchen featuring custom maple cabinets, quartz countertops, and stainless steel...
Kauai Loft Retreat PF-H307
Pono Kai's pool will be closed for repairs September 2025 through November 2025.The Kapaa Public Pool, located less than one mile from the resort, is open to the public.Welcome to Kauai Loft Retreat – Your Perfect Island Escape!Nestled in beautiful Kapaa, this...
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...
Hawaiian Treehouse, Peaceful Glamping Retreat
BAUMHAUS - a fully off-grid 12 feet high tree house on 2 acres of tropical rainforest on the Big Island of Hawaii. Experience stargazing like no where else in the world, while warming up at the fire pit. Chill out in the large hanging net or spend rainy days in the hot...
Kalo Homes ~ Sunset Retreat
Escape to our enchanting vacation rental nestled in the picturesque Makaha Valley. Ideal for nature lovers and beach enthusiasts, our cozy retreat offers the perfect blend of tranquility and adventure. With more than enough room for a large family or multiple small...
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...
❤️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...
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...
Puna Rainforest Hot Spring Retreat - Green Bamboo Cottage
Studio with oceanview, full kitchen and bathroom, queen size bed, plus small couch for one child or small adult. Perfect for couples. The property offers 1 mile private rainforest trail, pool, steam vents, two steam vent hot springs and private retreat setting...
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...
Charming Oceanfront retreat- Steps from the Beach, 2BR/2BA Polo Beach Club 308
For those looking for a peaceful, comfortable home base on Maui with true beachfront access. Just steps away, you can enjoy wonderful swimming and snorkeling- no roads to cross, no long walks. From our lanai, you might spot whales in the winter, turtles passing by, and...
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...
Lanai + Ocean Views: Secluded Holualoa Retreat!
Outdoor Dining | Fruit Picking On-Site | Short Drive to Snorkeling & BeachesSeeking a serene Hawaii escape? Look no further than ‘Lilikoi Inn!’ With stunning ocean views and a prime location just minutes from the shores of Magic Sands Beach, this 2-bedroom, 2-bath...
Emmalani Hale, a luxurious and tranquil retreat, AC, nestled in Princeville
Welcome to Emmalani Hale — Your Perfect Kauai Retreat!More than just a vacation rental, Emmalani Hale offers a luxurious and welcoming island escape designed for relaxation and comfort. Recently refreshed with fresh paint, plush carpeting, and elegant furnishings,...
Ohia Cottage: Your Coastal Retreat near Napoopoo Beach
Ohia Cottage is a well-appointed guest house on a secluded private farm in the heart of Kona s coffee belt.How amazing would it be to wake up and smell the coffee in Hawaii?! Our cottage is a perfect setting to host honeymooners celebrating their love or simply hosting...
Retreat to Paradise - private pool, hot tub, easy beach access
Spectacular private 92 foot long (x 3-1/2 to 5 ft deep) infinity edge pool overlooking the 15th hole of the Mauna Lani North Golf Course, along with a 12 person hot tub that waterfalls into the pool below. This is truly one of the nicest pools on the Big Island,...
Large Family Retreat on Calm Swimming Beach, A/C
Leimoku is a large and accommodating, beautifully updated, and modern Hawaii home on Oahu's famous North Shore. Located on the "quiet side" of the North Shore, away from all the crowds, this 3000 sq.ft. home is comfortable and luxurious, with three of the four large...
2.7 Acres of Exceptional, Secluded Retreat - Close to Beach & Shopping!
Nestled on the slopes of Hualalai, the Keauhou Hideaway is a private retreat on 2.7 acres of lush tropical vegetation. The 800' elevation affords a spectacular view of the Kona coastline and ensures warm, sunny days and cool nights. Completely renovated in 2005 and...
Luxury Upcountry retreat with breathtaking views!
PermitsBBMP2019/0006 & SUP2 2019/0003GE-081-730-0480-01 & TA-081-730-0480-01This is a BnB not a STRHOwners live on property.Aloha, sorry but at this time we are not hosting to families with children younger than 12 Mahalo.This is a NO SMOKING property. Mahalo. Our...
Hilo Studio Retreat with Gorgeous Park View, AC, WiFi, Pool
Welcome to your cozy getaway! This inviting studio is thoughtfully designed for comfort and convenience, making it the perfect home base for your adventures.Step inside to find a bright and airy living space, complete with a comfortable bed and stylish furnishings. The...
Villa Frangipani Tropical Beachside Retreat Kailua
About this spaceOnce inside our fully gated property you will be immersed in a lush tropical garden with palms surrounding a lagoon style pool. We are just a 2 minute barefoot stroll along a private lane to the soft white sands of Kailua Beach. Built in 1938, our home...
EXTRAORDINARY Hale Kuikahi Oceanfront Retreat - fully airconditioned!
Step onto the grounds of our oceanfront botanical garden retreat - Hale Kuikahi! Located in the quiet Paukaa area of Hilo just above famed Honolii surf beach, Hale Kuikahi boasts a private botanical garden walk onsite. Enjoy sweeping oceanfront views from almost every...
Keauhou Kona Surf & Racquet 188: Renovated Oceanfront Retreat
Welcome to Keauhou Kona Surf & Racquet 188 by Gather, a fully renovated two-bedroom, two-bathroom, Air conditioned oceanfront townhome in Kailua-Kona, Hawai'i. This two-story duplex accommodates up to six guests and offers panoramic 180° ocean views from nearly every...
Maui Breeze Retreat at Ho'olei openings Jul 19-29, Aug 22-Sep 14 & Sep 25-Oct 11
Surround yourself with the lush scenery of Maui Breeze Retreat at Ho'ol!ei, a tastefully decorated two-story villa with spectacular views of the Pacific Ocean. Your exquisite island retreat in Wailea offers spacious, well-appointed living quarters embraced by manicured...