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.
Maui Parkshore 209: Spacious 2bd / 2ba condo short walk to the beach
Experience Maui from this 2-bedroom, 2-bath vacation rental that overlooks the pool area and neighboring beach park, named Kamaole Beach 3 . The first thing you notice about this condo is the spectacular woodwork that decorates the walls in the living area and the...
Kamaole Sands 10-405: 2 Br Ocean View across Kamaole Beach Park III
Large Two-bedroom Oceanview Loft. This two-bedroom, two baths condo has a Queen Bed in Master bedroom (main level), two twins in the second bedroom (upstairs in the loft), and a pull-out sofa bed in the living room, allowing this unit to sleep up to six people. The...
Kamaole Sands Unit 1-302: Partial Ocean Views from this 3rd Floor Condo
Enjoy your Maui getaway at the Kamaole Sands. Located in building one, this one-bedroom, two-bath condo has room allowing this unit to sleep up to four (4) people. The large lanai offers partial ocean views and a great place to relax and enjoy the company of others....
Volcano Rainforest Retreat with a Hot Tub
As you pull up to this grand cedar style home you are immediately greeted by a beautiful rainforest that feels calming and relaxing. The first room is located to the far right corner of the building. There are a few stairs leading to a small covered patio for you and...
Royal Kahili retreat with pool, hot tub, lanai, & elevator - near beach
Royal Kahili B202Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Set in the Royal Kahili complex, this condo is just half a mile from a beautiful beach. Across the street, you’ll...
Cute and Cozy Couples Retreat w/ Private Lanai, Mountain and Ocean Views, A/C
Sealodge B4: Value and Views in PrincevilleOcean View Value at Sealodge B4! Enjoy Pacific Ocean and lush mountain views from your private lanai or cozy daybed in this budget-friendly Princeville condo. Features a King bed and Living Room AC. Nestled on the bluffs,...
Spacious retreat home with private pool & screened lanais - conveniently located
He'eia Haven Retreat - Units A & BOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Experience the best of Kailua-Kona with a stay at this spacious Hawaiian-style beach retreat home!...
Ground Floor Tropical Retreat - Professionally Managed
E Komo Mai. Welcome to Wailea Ekahi Village 18C, a delightful one-bedroom vacation rental located in the stunning Wailea area of Maui! This cozy retreat offers a serene garden view, making it an ideal choice for those seeking a peaceful and relaxing getaway. Upon...
Designer Oceanview Retreat: Steps to Kamaole Beach
Summary:Discover your perfect tropical escape at the Designer Oceanview Retreat, where style meets serenity. Just steps from Kamaole Beach I, this stunning condo offers a modern haven with breathtaking ocean views. Feel the soothing island breeze on your face as you...
Ocean View Retreat | Aston Waikiki Banyan 1BPO1 – Pool & Hot Tub
Resort Project: The Rec Deck Swimming Pool and Two Jacuzzi’s located on the 6th floor are closed for construction/renovation until the end of June 2026. Important: Construction may cause intermittent noise during your stayAston at the Waikiki Banyan: 1-bedroom Partial...
Blue Mango ~ Secluded orchard + beach retreat ~ no chores!
Aloha! Nestled among mango and avocado trees on a large 2-acre gated estate, this newly renovated container guesthouse offers the perfect space for 2. Everything you need, nothing you don’t. Equipped with 2 split A/C units, stay cool indoors and then enjoy the Oahu...
Holo Hou Hale - Lahaina Shores Retreat on Front St
Come Stay at Holo Hou Hale! This newly renovated Lahaina Shores studio puts you steps from the golden sand, iconic surf breaks, sunset strolls, and stunning mountain views. Enjoy a king bed, full kitchen, pool, hot tub, and direct beach access. Relax, recharge, and...
Modern Island Retreat | Central Location + Parking
Location, location, location! Our elegantly renovated studio is just one block from Waikiki Beach and at the heart of shopping, dining, and nightlife. Enjoy the convenience of FREE parking and FREE Wi-Fi. The well-equipped kitchen includes all the cooking essentials you...
Relaxed Kaneohe Retreat | Carport, AC, W/D
This spacious 3 bed, 2 bath Kaneohe townhome has everything you need — full kitchen, in-unit W/D, AC, a 2-car carport, and a dedicated workspace ideal for remote workers. Hit the water with complimentary kayaks and a surfboard available for guest use, or explore the...
🌊🏄🏻🏝️ Summer in Maui - Kapalua Sunset, Golf and Beach Retreat
Escape to paradise at this beautiful 2-bedroom, 2-bath condo in the highly desirable Kapalua Golf Villas. Overlooking the Bay Course near the 10th hole, this spacious retreat offers sweeping golf course views, glimpses of the ocean beyond the pine trees, and...
Mā’ili Blue by Gather: Oceanfront Retreat w/ Beach Access & Sunset Views
Ma'ili Blue is a private oceanfront retreat on Maili Point, where wide coastal views, steady trade winds, and golden sunsets define each day. Set directly along the shoreline on Oahu’s sunny west side, this spacious holiday home offers a relaxed sense of island living...
Mā’ili Blue Estate by Gather: Oceanfront Retreat w/ Beach Access & Sunset Views
Ma'ili Blue Estate is a private oceanfront retreat on Maili Point, where wide coastal views, steady trade winds, and golden sunsets define each day. Set directly along the shoreline on Oahu’s sunny west side, this spacious home blends relaxed island living with...
NEW! Waikoloa Village Retreat - Charming 1BR Condo
Welcome to your island retreat in Waikoloa Village—where comfort, style, and relaxation come together. This bright and tropically designed condo offers an open-concept layout with modern touches and a warm, inviting feel the moment you walk in.Peaceful Ground-Level...
Westin Nanea 2-Bedroom Resort View: Maui's Ultimate Family Retreat Awaits You!ja
Spread out with the whole family in this spacious two-bedroom suite.The Westin Nanea Ocean Villas is more than a resort; it’s an invitation to immerse yourself in the spirit of Maui. Nestled on the pristine sands of Ka’anapali Beach, this luxurious resort blends modern...
Escape to Paradise at Lagoon Tower by Hilton Grand Vacations – Studio Retreat!
Experience the vibrant energy of Waikiki from the heart of the Hilton Hawaiian Village® Waikiki Beach Resort, where the Lagoon Tower Studio combines modern comfort with a prime tropical location. Perfect for couples or small families, this cozy retreat offers an ideal...
High-Rise Retreat | Panoramic Ocean & City Views
Soar above Honolulu in this stunning 3-bedroom, 2-bath retreat on the 36th floor of the well-appointed Rycroft Tower. Wake up to sweeping panoramic ocean and city views from every angle. Sleek, modern finishes and high-end appliances make this the ultimate home away...
Beachfront Executive Retreat - The Waimanalo Villa
Wake up to the sound of waves at this luxurious 3BR, 2.5BA beachfront villa on pristine Waimanalo Beach. Enjoy direct access to sweeping ocean views and seamless indoor-outdoor living. The home features an upstairs private suite with a full kitchen, ideal for guests or...
Iconic Pink Waikiki Retreat | 2 Blocks to Sandy Shores | Private Lanai, Pool
Experience vintage Hawaii without breaking the bank. Simple, budget-friendly property located in the heart of downtown Waikiki and just a 5-minute walk from Waikiki Beach. Guests can enjoy live Hawaiian music and a mini hula show every Monday night while staying in the...
Kauai Garden Retreat | Pono Kai Resort | PK-H205
Summary:Escape to your own slice of paradise in this charming 1-bedroom, 1-bath second-floor garden view condo in the heart of Kapaa. Surrounded by lush tropical landscaping, this peaceful retreat offers the perfect blend of comfort, convenience, and island charm. Ideal...
PEACEFUL BEACH RETREAT, 2-Br. Newly Furn. Hm., 2 Min. Walk to Beach, 30 Day Min.
Peaceful Beach Retreat in Kailua/Lanikai – Steps from the OceanWelcome to your private island escape in the highly sought-after Kailua/Lanikai area of Honolulu. This beautifully upgraded, newly furnished beach home offers a peaceful, light-filled retreat just steps from...
Modern Island Retreat | Central Location + Parking
Location, location, location! Our elegantly renovated studio is just one block from Waikiki Beach and at the heart of shopping, dining, and nightlife. Enjoy the convenience of FREE parking and FREE Wi-Fi. The well-equipped kitchen includes all the cooking essentials you...
Waikiki Ocean Luxe Retreat | Panoramic Views
Enjoy comfort and convenience in this newly renovated APril 2026 ocean-view suite located in the heart of Waikiki. Just minutes from Waikiki Beach and Waikiki Marketplace, you’ll be close to shopping, dining, and beach activities. Grab a quick bite or coffee at Musubi...
Scenic Beach Retreat | 3 Spacious Rooms near Kanaha Beach Park - 5 Min Drive
This listing is for 3 separate rooms within a hotel. The price shown in the listing covers all 3 rooms.✦ Each room is 540 sq. ft, equipped with complimentary toiletries, high definition 32-inch TV, available with Standard cable.✦ Rooms are not adjoining and possibly not...
Breathtaking Beach Retreat Perfect for Romantic Couple Stay | Outdoor Pool
This listing is for a room within a hotel.✦ Your room is 540 sq. ft, equipped with complimentary toiletries, high definition 32-inch TV, available with Standard cable.✦ Cleaning services availability and frequency vary by stayThere are a few additional details to know...
Breathtaking Maui Beach Retreat | Spacious Ocean View Retreat Perfect for Couple
This listing is for a room within a hotel.✦ Your room is 270 sq. ft, equipped with complimentary toiletries, high definition 32-inch TV, available with Standard cable.✦ Cleaning services availability and frequency vary by stayThere are a few additional details to know...
Lovely Hawaii Retreat | 3 Gorgeous Ocean View Rooms w/ Pool and Beach Access
This listing is for 3 separate rooms within a hotel. The price shown in the listing covers all 3 rooms.✦ Each room is 270 sq. ft, equipped with complimentary toiletries, high definition 32-inch TV, available with Standard cable.✦ Rooms are not adjoining and possibly not...
Ocean View Family Retreat - New · Modern · Spacious · King · AC
-This newly remodeled 3BR/2.5BA features soaring ceilings, 2 split AC, spacious covered patio with fresh island breezes, Garage parking.-Escape to panoramic ocean view paradise, Sip sunset cocktails at your private outdoor bar as the sun melts into the Pacific.-Fully...
Akaka Falls 6BR Ocean‑View Retreat with Hot Tub
Spacious 6BR ocean‑view retreat in historic Honomu, 20 minutes from Hilo and just minutes from Akaka Falls State Park and Kolekole Beach Park. Perfect for large groups and families, our bright Hawaiʻi‑style home has a wraparound deck, huge backyard, private hot tub and...
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,...
Lush Garden Retreat l Pool, Urban Bikes & Curated Island Experiences
Endless adventure awaits in Kailua-Kona! Whether you're staying for a day or a week, our hotel puts you close to top attractions, local dining, and must-see spots like the Amy B.H. Greenwell Ethnobotanical Garden and Pu'uhonua o Hōnaunau National Historical Park....
Princeville Ohana Retreat Minutes to Hanalei Bay!
Escape to the heart of Princeville on Kauai’s North Shore and enjoy the perfect blend of island comfort and tropical charm at this beautifully renovated retreat. Just minutes from Hanalei Bay, Anini Beach, Tunnels Beach, and scenic hiking trails, this spacious home...
Diamond Head Villa by Gather: Luxury Gold Coast Retreat w/ Pool, Jacuzzi & Beach
Set along the prestigious Gold Coast of Honolulu, Diamond Head Villa captures the essence of island sophistication with its private beach access, contemporary architecture, and effortless indoor-outdoor flow. This two-story ocean-view retreat offers an exclusive haven...
Embrace a Pet-Welcome Retreat! Near the Shores of Ho’aloha Beach!
Discover the magic of Maui from this amazing harborfront property!This listing is for a room within a hotel.✦ Your room is 300 sq. ft, equipped with complimentary toiletries, TV.✦ Cleaning services included in the nightly price.There are a few additional details to know...
City & Sea Retreat: Pool, Sauna, Rooftop Views - Your Waikiki Oasis!
Family-friendly property located just steps from the beachThis listing is for a room within a hotel.✦ Your room is 443 sq. ft, equipped with complimentary toiletries, kitchen with basic amenities, high definition 32-inch TV, available with Premium cable, ensuring...
Waikiki Retreat Perfection: 2 Units, Pool, Sauna, Steps from Famous Beach!
Family-friendly property located just steps from the beachThis listing is for 2 separate rooms within a hotel. The price shown in the listing covers all 2 rooms.✦ Each room is 360 sq. ft, equipped with complimentary toiletries, kitchen with basic amenities, high...
🌴Panoramic Ocean Views • Private Pool + Spa • AC • 4BR Kona Retreat Sleeps 10🌴
Welcome to Hale Mahi'ai, your private island escape—where luxury, comfort, and breathtaking natural beauty come together.This stunning 4-bedroom home offers the perfect balance of seclusion and convenience. Hale Mahi'ai is tucked away in a quite Kona neighborhood while...
Post-Adventure Bliss! 4 Units, Sauna, Rooftop Sunset Views in Waikiki Retreat!
Family-friendly property located just steps from the beachThis listing is for 4 separate rooms within a hotel. The price shown in the listing covers all 4 rooms.✦ Each room is 360 sq. ft, equipped with complimentary toiletries, kitchen with basic amenities, high...
Relaxation Retreat: Unwind in Tranquility! 2 Amazing View Suites w/ Balcony |Spa
Welcome to your ultimate tropical retreat! Walk to Waipouli Beach & Coconut Marketplace, with Opaekaa Falls just a drive away. Perfect for island exploration!This listing is for 2 separate rooms within a hotel. The price shown in the listing covers all 2 rooms.✦ Each...
Tropical Retreat w/ Outdoor Pool, Free Parking, Steps from Papaloa Beach!
Welcome to your ultimate tropical retreat! Walk to Waipouli Beach & Coconut Marketplace, with Opaekaa Falls just a drive away. Perfect for island exploration!This listing is for a room within a hotel.✦ Your room is 725 sq. ft, equipped with complimentary toiletries,...
Oceanview FarmLux Estate | Stargate Farm Retreat
Welcome to Stargate Farm — a FarmLux oceanview estate on 18 private acres in North Kohala. This brand-new sanctuary blends luxury living with the living land, offering ocean views, vaulted wood ceilings, Turkish travertine, granite-slab showers, and three serene king...
Beachfront South Shore Retreat with Stunning Ocean View Deck, Surf Near Waikiki
This memorable house is the perfect home base for your trip to Honolulu. With three cozy bedrooms featuring one king bed and two queen beds, guests can relax comfortably after a day of exploring. The two bathrooms include a bathtub and a separate shower, offering a...
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...
This rare multi-residence offering combines three neighboring luxury oceanview suites to create an exclusive six-bedroom retreat, ideal for large families and groups seeking space to gather and reconnect without sacrificing privacy. From your elevated sixth-floor...
Eco Ocean Oasis, Tropical 1-Acre Retreat with Pool, Hot Tub, AC, Lanai
Escape to a lush 1-acre tropical retreat just minutes from the coast. This bright and spacious 1,695 sq ft custom home offers a private, tranquil East Hawaiʻi setting with cathedral ceilings, bamboo flooring, abundant natural light, and an expansive covered lanai for...
NEW! Napili Point Oceanfront Sunset Retreat - Unit A1
Unit A1 is a point oceanfront one-bedroom condo at Napili Point Resortoffering 602 sq ft of living space with a king bed, queen hide-a-bed sofa, airconditioning, ceiling fans, and 2 TVs. It comfortably sleeps up to four guestsand features an 86 sq ft lanai with direct...