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.
Peaceful retreat with pool, gym & BBQ
Summary:Family Friendly, Near Pool, Updated BathroomsThe Space:Welcome to your serene Waikoloa escape - ideal for families, couples & relaxation seekers! Enjoy peaceful mornings, nearby beaches, & shared resort-style comforts:- Sleeps 6 | 2 bedrooms | 3 beds | 2 baths-...
Spacious retreat with pool & private lanai
Summary:Private, Access to Mauna Lani Beach Club, Spacious, Great Backyard!The Space:Welcome to your peaceful Hawaiian retreat in the Islands at Mauna Lani, where tropical gardens, nearby beaches & resort amenities invite pure relaxation:- Sleeps 5 | 2 bedrooms | 4 beds...
Oceanfront Bliss – A Relaxing Retreat with Breathtaking Views
Whether you’re here to soak up the incredible sunsets, spot sea turtles from the lanai, or witness majestic whales (in season),this serene escape is ready to make your island dreams come true. Step inside this fully updated condo and experience modern comfort paired...
Kona Pacific C416 by Gather: 1BR Condo Retreat w/ Pool & Ocean Views
Welcome to Kona Pacific C416, a beautifully appointed 1-bedroom, 2-bath ocean-view condominium in the heart of Kailua-Kona, Hawai‘i. This 830-square-foot retreat offers modern comfort and tropical tranquility, accommodating up to four guests—ideal for couples, families,...
New! Palms 702 - Romantic Retreat - Split AC in Bedroom - Open-Air Living Area
* * * * The Palms at Wailea Pool Area will be Closed for Annual Maintenance Tuesday, Sept,. 15th through Friday, Sept,.18th 2026. The Pool Area Will Reopen Saturday September 19th with Regular Hours. * * * * Discover the perfect Maui escape at Palms at Wailea 702, a...
Tropical Serenity - Lovely Maui Retreat 1Bed Suite
Discover Maui at Maui Banyan Q110 apartment, a lovely 1-bed 1-bath apartment steps from Kamaole Beach Park II, perfect for up to 4 guests. Conveniently located right next to the upper pool area which also includes six Weber BBQs. Relax on the lanai amidst lush greenery,...
Cozy ground floor retreat on Kaanapali Beach
Welcome to your tropical getaway at Kaanapali Shores 144, a 1-bedroom, 1-bathroom condominium that offers convenient ground-floor access, Unit 144 can accommodate up to 4 guests. When it's time to retire for the night, you'll find a king-size bed adorned with...
Holomakani Retreat: Your Ohana's Hale (Home) by Kaanapali Beach
This is a legally permitted vacation rental according to the County of Maui ordinances.Ocean Views, Private Pool & Spa, Steps to Kaanapali Beach – Your Maui Paradise Awaits E komo mai (welcome) to your island sanctuary, where the beauty of Maui and the spirit of aloha...
Romantic Tropical Retreat, 150 yds from the Ocean!
Kona Dreams sleeps 4 adults. Walk 150 yards to the ocean. 2 bed/2 bath tropical home in a quiet neighborhood. Chef’s kitchen, laundry, beach gear, use of kayak. Free phone, wireless, off-street parking. Hiking and beach on-site. Maid service with an extra fee.Kona...
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...
Panoramic ocean views and neighboring islands
Step inside Mahana 517, a 1-bedroom, 1-bath, 5th-floor condo that offers direct ocean views, an in-unit washer and dryer, and a central air conditioning system. This property has elevators. Unit 517 can accommodate up to 4 guests. The master bedroom features a king-size...
Coastal Condo Retreat - Exquisite Views. Short Walk to Beaches. Tennis Courts!
This perfectly positioned condominium with private lanai will inspire your sense of adventure as well as be your space for relaxation! Support Maui's economic recovery by building your book of vacation memories in central Kihei close to everything you want to do! The...
Halekii Sunset: Beautiful 4 Bedroom Home in Lush Kealakekua
*Please note that a neighboring home near the property is currently undergoing intermittent construction. While work is not constant, there may occasionally be construction noise during normal daytime working hours. To account for this potential disturbance, the rates...
Exceptional Ground Level Retreat: Kihei Surfside #102 – Stunning Pacific Views!
Kihei Surfside #102 – Stylish Ground-Floor Ocean View Condo with Recent UpgradesDiscover the best of coastal living at Kihei Surfside #102, a beautifully updated ground-floor condo offering ocean views and easy beach access. This 1-bedroom, 1.5-bathroom unit sleeps up...
Relax in Keauhou with Stunning Kona Coast and Golf Course Views
Escape to a peaceful retreat on the Kona Coast, where breathtaking ocean and golf course views await. This beautifully remodeled 1-bedroom, 2-bath condo at Keauhou Akahi overlooks the stunning Kona Country Club and the vast Pacific Ocean. The open-concept living area...
Garden Island Retreat - Islander on the Beach #116 - Studio Condo
Beautiful ground level studio #116 w/kitchenette at Islander on the Beach. Just steps away from the beach! Great, quiet location in the resort complex and has an ocean view from the lanai. Islander on the Beach, Hawaiian Style Resort, is set on six acres of oceanfront...
Gorgeous, remodeled 3 bed/2.5 bath Ka'anapali Plantation
Welcome to your private island sanctuary—a stunningly remodeled 3-bedroom, 2.5-bathroom villa set within the lush, gated grounds of Ka’anapali Plantation, one of West Maui’s most exclusive low-rise communities. Perfectly positioned between world-class golf courses,...
Modern condo in Kona- Close to the ocean & dining
Aloha, welcome to Kona Ohana Hale. Escape to a modern 1BR Kailua Kona retreat filled with paintings and photos from local artists, giving the space a unique, authentic island vibe. Centrally located, you’re less than a mile from the ocean, dining, and shops—perfect for...
Private Cliffside Ohana Retreat at Kalapaki Beach!
Experience the very best of Kauai from the comfort & convenience of this luxury oceanfront retreat! Step outside to enjoy incredible ocean views overlooking Nawiliwili Harbor from your private cliffside balcony, or spend the day kayaking, surfing and relaxing on...
Oceanfront Sea Village #3212 retreat with stunning views and open living spaces
Turn moments into memories in this incredible oceanfront Sea Village #3212 property. This two-bedroom, two-bathroom has all one is looking for. Enjoy the open layout of the living area and stunning ocean views from the kitchen to the lanai.Upon entry, you can't help but...
Ocean Views, Beach Access, and a Cozy Hawaiian Retreat: Ma'alaea Banyan 416
Maalaea Banyans 416 offers stunning ocean views and is a real charmer, making for the perfect Hawaiian retreat. You can enjoy your morning coffee while watching a whale breach, especially during the season, or turtles almost nightly right from your private...
Hawaii Beach Retreat- Sand, Surf, Pineapples and Paradise
Welcome / E komo mai,This is your getaway for family or a group of friends looking for a beautiful oceanfront home with amazing surf and sunsets year round. Minimum 30-day rentals. This property may not be rented for less than 30 consecutive days. Rental prices will not...
The Sandy Feet Retreat - Oceanfront top-floor corner unit on Kauai Coconut Coast
This gorgeous oceanfront, two bedroom, two bath condo at Lae Nani in Kapaa is the perfect place to relax and enjoy yourself with friends and family. Private, top floor corner unit (no one above you), featuring high ceilings, a fully equipped kitchen remodeled with...
Newer-built studio with WiFi, TV, & walk-in shower - close to the beach
Star of Waikoloa Beach Resort - Ainamalu Ohana Guest HouseOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'This newer-built studio will be a great getaway while you're in Waikoloa....
Oceanview 2BR Condo at Makahuena | Multi-Level Poipu Retreat, AC+Resort Amenities
E Komo Mai, Welcome to The Makahuena 4305!“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 is a multi-level condo on the second story of the building,...
Spacious Island Retreat With Ocean Views In Poipu!
Experience the very best of Kaua‘i’s South Shore at Sunset Kahili—Poipu’s premier oceanview escape.This spacious 1-bedroom condo offers endless views of the Pacific and unforgettable sunsets, making it the perfect retreat for couples or solo travelers. Located just a...
Tropical Forest Retreat Near Ocean - Ho'ohauoli
This private Pāhoa getaway offers the perfect location for your next Big Island adventure! Surrounded by lush, tropical foliage, this home features a large covered lanai, a fenced yard, a newly renovated kitchen, and even an avocado tree that you can enjoy in season....
Hale Makai Cottage #5: Kauai North Shore Retreat
Cottage #5 offers an idyllic Hawaiian escape for families or groups of friends seeking the beauty of Kauai's North Shore. The cottage features two bedrooms and two bathrooms. The primary bedroom includes a luxurious king-size bed and an ensuite bathroom. The second...
🏖️Concierge Included | Walk to Beach | Central AC | vrKCV
vrKCV - White Sands Village 223, Professionally Managed by Kona Coast VacationsAcross from Magic Sands Beach | 2BR Kona Condo w/ AC, Lanai & Pool | White Sands Village #223Stay steps from one of Kona's most famous beaches at White Sands Village #223, a comfortable...
Big Island "Whole House 5BR/2BA" Retreat For Work & Play! Sleeps 16
The Mele Vacations property is a lovely property nestled in the heart of Hawaiian Paradise Park neighborhood. There are large fruit trees that bear a harvest for your picking pleasure along with comfortable furniture, large lanai, free open wireless Internet and long...
Ke Nani Kai 132 - Spacious 2 BR/2 BA Relaxing Molokai Island Retreat
Located between Oahu and Maui...Molokai is an undiscovered treasure. 'The Friendly Isle' is a family-oriented island with deep connections to its Hawaiian traditions. Unlike the tourism driven other islands, here you can relax, slow down and have your own space. Nowhere...
KK 307 OceanFront 2BD Retreat with Breathtaking Views
Kulakane 307 Newly Remodeled OceantFront 2Bedroom for Picture Perfect Retreat to Relax Recharge and Rejuvinate. Ocean Views for Beautiful Sunsets and Spectacular Whale Watching Kulakane 307 is an oceanfront newly remodeled condo (2025) with breathtaking views...
About Wailua Bay View #309Our unit offers a drop-dead beautiful ocean front view.Wailua is on the island's sunny East side, allowing you to explore both North and South shores easily.Great swimming, hiking and kayaking are moments away.You can explore restaurants and...
Oceanview 5th Floor Retreat Steps from the Beach,
If you're looking for a condo on Maui, look no further. Quiet 5th floor unit in the C Building with views of the ocean, Mt. Haleakala, and the garden from the lanai. Walk across the street to Kamaole Beach Park II for excellent swimming, snorkeling with occasional sea...
Stunning Oceanfront Retreat, Kahana Reef 218
Direct oceanfront unit in a highly desirable location right in between the popular areas of Kaanapali and Kapalua. When you sit on the balcony, you have panoramic views looking out to the islands of Lanai and Molokai. You will also see whales and sea turtles and have...
Serene Aloha Retreat: Beachfront Bliss in Napili's Charming Studio/Suite
Aloha Napili Resort Beach, Snorkel with Turtles & Whale WatchSteps to Napili Bay | Snorkel with turtles, walk to sunset dining, and relax in a remodeled studio with A/C, beach gear & no resort fees.Welcome to our condo at Napili Shores, a beloved oceanfront resort...
Tranquil tropical retreat with pool, hot tub, and golf nearby
Maui Eldorado Resort E205Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Feel your worries melt away with the ocean breeze as you relax in style at this Lahaina home. Featuring...
Beachfront Oasis: Kihei Beach #303, Your Retreat with Breathtaking Ocean Views!
Kihei Beach #303 – Remodeled One-Bedroom Beachfront CondoWelcome to Kihei Beach #303, a beautifully remodeled one-bedroom, one-bathroom beachfront condo offering comfort, charm, and sweeping ocean views. Located in a six-story beachfront property in North Kihei, this...
Oceanfront Oasis: Ground Floor Retreat - Sugar Beach #130
SUGAR BEACH RESORT, #130Welcome to Sugar Beach Resort #130, a beautifully updated ground-floor condo that combines modern upgrades with the ultimate beachfront convenience. Located in North Kihei, this oceanfront oasis allows you to step directly onto miles of golden...
Ocean View Retreat on the Garden Island!
Experience the best of Kauai’s North Shore at this newly updated condo in Princeville, one of the island’s most sought-after communities. Enjoy breathtaking Pacific Ocean views right from your living room or private lanai, with a lush grassy lawn just beyond. Spend your...
Hale Halai beautify large home perfect for families & small company retreats
This 5000 square foot spacious home with an open floor plan is excellent for families, friends, and co-workers to gather and enjoy each others company. It has 7 bedrooms, 5 bathrooms, A/C, and a private pool. Tropically landscaped grounds with a BBQ and a spacious yard....
Hoyochi Nikko A Quaint Oceanfront Retreat in Maui
Hoyochi Nikko 202This two-bedroom unit features a master bedroom on the main level with a king-size bed and a spiral staircase leading to a large lofted second bedroom with a queen-size bed. The unit is tastefully decorated with many custom features, and high vaulted...
Family retreat with beach club access & pool
Summary:Easy walk to Anaeho'omalu Beach, Garden-level lanai, Quiet, Gated, Free ParkingThe Space:Welcome to your peaceful Hawaiian escape at Kolea 16A - where tropical gardens meet island comfort just a short walk from the beach:- Sleeps 6 | 3 bedrooms | 4 beds | 2...
Discover Coastal Comfort: Oceanview Retreat at Kamaole Nalu #304
Kamaole Nalu #304 – Modern Ocean View Retreat in KiheiKamaole Nalu #304 is a beautifully remodeled two-bedroom, two-bathroom condo offering ocean views and modern island comfort. Located on the third floor of this oceanfront property, the condo provides an inviting...
Tranquil Retreat Sunbelt of Hawaiian Paradise Pk
Summary:Discover the charm of island living in this spacious home nestled within the serene enclave of Hawaiian Paradise Park. Enjoy the essence of the sun-soaked Sunbelt region, where each day invites you to embrace the beauty of Hawaii's natural landscape. With ample...
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,...
WEK 37C Getaway at Wailea Retreat w AC Pool Near Beach and Golf Course
Wailea Ekahi 37C Experience the Luxury of Wailea at Updated 1Bedroom Condo with Split AC Throughout and Comfortably Furnished and a Short Walk to South Maui Beaches Escape to the natural beauty and serenity of Hawaii at Wailea Ekahi 37C. Located in the exclusive resort...
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...