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 1051A: Relaxing 2BR Retreat, Ideal for Family, Close to Amenities
Tucked inside the gated community of Ko Olina Kai, Ko Olina Kai 1051A by Gather is a welcoming two-bedroom, two-bath condo perfectly suited for extended stays. With 1,144 square feet of living space, tropical landscaping views, and resort amenities just steps away, this...
Discover the ultimate Hawaiian retreat at Kanaloa Condominium
Welcome to this spacious and beautifully appointed 3-bedroom condominium at Kanaloa Condominium at Outrigger, nestled in the stunning surroundings of Hawaii. This luxurious unit offers a blend of contemporary design and island-inspired decor. Enjoy breathtaking views of...
Kihei Luxury Suite, Pool, Walk to Beach
Summary:🏝 Prime Location – Steps to Kamaole Beach, dining & shops🛏 Luxury Comfort – King bed & memory foam sofa bed🏊 Resort Perks – Pool, hot tub, outdoor grills📺 Entertainment – 65" Smart TV, free Netflix & fast WiFi🛎 Seamless Stay – Self-check-in & Smart Lock🎟...
The Cottage: Oceanfront Honeymoon Retreat w/Gorgeous Views, By Kahalu'u Beaches
Perched directly above the lava-rock shoreline along Ali‘i Drive, The Cottage is a classic oceanfront retreat where coastal breezes, island color, and unobstructed sunsets shape each day. This one-bedroom home blends nostalgic Kona charm with thoughtful modern updates,...
Kona Lunapule 205B: Tranquil 2BR Retreat with Ocean Views
Kona Lunapule is centrally located in Kailua Kona, in the Island of Hawaii. It's just a short drive to local restaurants and shops along the coast of Ali’i Drive. This quaint complex features a communal pool and onsite parking. Upstairs you will find 205B; a quiet and...
Beachfront retreat with lanai, WiFi, pool, & hot tub - prime turtle spot
Maalaea Banyans 105Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Enjoy lying on lounge chairs in front of a beach, watching sunsets from your lanai, or just seeing if the sandy...
1 Bedroom Diamond Head retreat with stunning ocean views & full kitchen.
LEGALLY PERMITTED STR- 🌬2947 Kalakaua Ave #1202🌬⚕⚕For your health and safety⚕⚕We utilize additional Sterilization procedures between reservations.🌬Let the ocean breezes surround you in our beautiful 12th floor ✔1 BEDROOM condo here on Honolulu's Gold Coast at the...
Kahana Reef 101: Completely Remodeled 1 Br condo with Ocean Front Views
Direct oceanfront views of the Pacific Ocean and the neighboring island of Molokai from this ground-floor one-bedroom vacation rental located in Kahana area of W. Maui. This vacation condominium features a remodeled kitchen and bathroom with tiled flooring throughout....
Kuilima Golf Retreat
Welcome to your perfect getaway at the Kuilima Golf Retreat! This beautiful rental offers exceptional amenities and is just a short walk from the beach.This inviting unit accommodates up to four guests, featuring one bedroom, a comfortable sofa bed, and one bathroom....
Central 2-Bedroom Retreat: Steps from Kalapaki Beach with Air Conditioning
Comfort and Convenience in the Heart of Kaua‘i – 2-Bedroom Vacation RentalEnjoy the best of Kaua‘i from this centrally located, split-level 2-bedroom condo in Līhu‘e, just minutes from the airport and ideally situated near Kalapaki Bay. Whether you’re here to explore...
Oceanfront Kahana Retreat: 1BR End Unit with Stunning Views & Whale Watching
Welcome to your tropical paradise retreat in Kahana! Experience the epitome of oceanfront living with breathtaking full ocean views from this exclusive end unit. Nestled in a serene and private setting, this 1-bedroom, 1-bath vacation rental offers a unique blend of...
Ground Floor Treasure: Beautiful Oceanfront Retreat - Kihei Surfside #107
Kihei Surfside #107 – Ground-Floor Ocean View Retreat Just Steps from the BeachEnjoy the relaxed charm of South Kihei at Kihei Surfside #107, a ground-floor ocean view condo with direct access to the resort’s iconic oceanfront lawn. This 1-bedroom, 1-bathroom unit...
Sunset Haven: Elegant Beachfront Maui Retreat
Summary:🔹 Walk to Charley Young Beach – Just 3 blocks away 🌅 Ocean Views – Enjoy coffee on the private lanai 💤 King-Size Bed – Luxury linens for restful sleep 📶 Fast WiFi & Smart TV – Work& stream seamlessly 🏖️ Beach Gear Included – Chairs, towels umbrellas 🏊♂️ Pool &...
Ocean View Oasis Escape, Sunset View & Fast Wi-Fi
Summary:🌴 Steps to the Beach – Charley Young & Kamaole 1 nearby📍 Prime Location – Walk to top restaurants & shops💻 Fast WiFi + Smart TV 🏠 Spacious & Stylish – Modern decor & cozy ambiance💎 Luxury King Bed – Guests rave about comfort!🏊 Resort Perks – Pool, hot tub, BBQ,...
Waterfront retreat with gourmet kitchen, spacious lanai & W/D
Wena ʻula EscapeOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'When you picture paradise, it looks exactly like this. Sitting directly by the water, this palm-lined home is the...
New listing! Poipu 3br Retreat with Pool and Gym
Poipu Retreat with Mountain Views and Resort-Style AmenitiesDiscover this breathtaking second-story sanctuary in the prestigious Pili Mai resort, where panoramic views of Kauai's stunning South Shore create the perfect backdrop for your tropical getaway.Nestled within...
Peaceful 2BR retreat with pool & golf views
Summary:Quiet Villa, Large Lanai, On the Golf CourseThe Space:Welcome to your serene island escape in Waikoloa Village - where ocean views, gentle breezes & resort comforts await:- Sleeps 4 | 2 bedrooms | 3 beds | 2.5 baths- Shared pool, hot tub & fitness center-...
Lagoon View Resort Retreat
Keep it simple at this peaceful at this Resort Hotel Room. A lovely view from private lanai overlooking lagoon and mountains beyond at this popular kauai`s East side Oceanfront Resort location. An easy 5 minute drive from the LIhue airport, an ideal resting spot to end...
Coconut Plantation 1080-1: Spacious 3BR Ko Olina Retreat w/ Wrap-Around Lanais
Experience island living at its finest at Coconut Plantation 1080-1 by Gather, a luxurious two-story townhome located in the heart of Ko Olina Resort. Spanning 1,715 square feet, this elegant retreat accommodates up to six guests and offers an ideal blend of comfort,...
Grand Champion Villa Getaway - Wailea Beaches
Summary:🌴 Prime Location – Walk to beach, dining & shops🌅 Tranquil Balcony – Enjoy morning coffee w/ lush views 💤 Luxury Beds & Linens – Ultimate comfort for deep rest 🏊 Resort-Style Amenities – Pool, hot tub & tennis courts 🚗 Free Parking (1 spot) – Secure &...
Ocean View Penthouse: Steps to Beach, Fast Wi-Fi
Summary:🔹 Prime Location! Walk to beach, dining & shopping 🌅 Breathtaking Ocean Views – Enjoy from private lanai 💤 Luxury Memory Foam Bed – Sleep like royalty 🍽️ Fully Equipped Kitchen – Cook with ease 🏊 Resort Perks – Pool, hot tub & BBQ grills 🎟️ Exclusive Coupons –...
Holua Kai #20: Tropical Ocean View Retreat at Holua Kai w/ Private Pool/Spa & AC
Holua Kai #20 welcomes you to a refined coastal retreat along the Kona Country Club’s Makai Golf Course, where sweeping ocean vistas meet the comfort of a gated, pedestrian-friendly community. Designed for both relaxation and connection, this two-story home blends...
Townhouse Retreat with Ocean Views From Upper & Lower Lanai - Wailea Ekahi #30B
Wailea Ekahi Village #30B Discover the perfect blend of luxury, comfort, and location at Wailea Ekahi Village #30B. This spacious two-story townhouse offers stunning ocean views from both floors, a fully remodeled kitchen and bathrooms (March 2025), and unbeatable...
Royal Mauian 205 - Splendid Oceanview Retreat, Stroll to Dining and Shopping!
Royal Mauian #205 – Upgraded Oceanfront Two-Bedroom CondoRoyal Mauian #205 is a two-bedroom, two-bathroom condo with an upgraded interior and breathtaking oceanfront setting. Perfect for families or small groups, this stylish retreat offers split-duct air conditioning,...
Secluded Paradise: Ocean view oasis with private lanai and island enchantment
Sealodge B6 is a charming little hideaway that blends Hawaiiana vintage charm with modern updates! This quiet and cozy condo has a comfortable master suite with a queen bed, as well as a punee (Hawaiian day-bed) in the living room that's great for laying and watching...
The Hula's Retreat - Well Equipped at Waikiki Grand
☀ Legally permitted vacation rental ☀ — Waikiki Grand Hotel® —134 Kapahulu Ave, Suite 217Workstation & fully equipped kitchenette.Fully equipped comfort greets you when you open our door to Waikiki Grand Hotel® suite 217.Whether visiting for 2 days or 2 weeks, we've...
Shores at Waikoloa Unit 111: 1 Br condo in the Tamarind Tower, sleeps 2
A Repair and re-tile project on the 2nd-floor walkway (catwalk) in the Tamarind Tower will start the week of April 21st, 2025, with plans to be completed late-June. While the walkway will remain accessible when under construction, there will be considerations for all...
Refreshed Tropical Private Ocean View Retreat On South Shore
Experience the best of Poipu from this stunning oceanview condo on Kauai’s sunny south shore! Located in the heart of Poipu, this spacious, resort-style home offers everything you need for the ultimate Garden Isle vacation. Just a short walk to world-class beaches,...
Private Island Retreat At The Cliffs Princeville!
Experience panoramic views of the Pacific Ocean and iconic Mt. Makana ("Bali Hai") from this private and spacious condo at The Cliffs in Princeville. Perched on a scenic bluff with distant ocean vistas and lush tropical surroundings, this beautifully appointed retreat...
North Shore Oceanfront Private Retreat with Pool!
Absolutely the best location on the north shore of Kauai! This beautifully furnished, spacious, and private home is situated in the heart of Princeville minutes away from all of the world-class beaches, mountain forest trails, outdoor activities, golf courses, and...
Bright, island retreat with ocean views, pool, & patio
Mahina Surf 104Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Oceanfront and filled with island vibes, this efficient condo has everything needed to make unforgettable memories and...
Stunning Waikiki Beach Retreat - 2 mins from Ocean
Legally permitted rental - TRADEWINDS PLAZA2572 Lemon Rd #305** For your health and safety, we utilize additional Sterilization procedures between reservations.Gorgeous Queen 1 bedroom spacious apartmentAll the appliances / furniture are brand new in this gorgeous...
Oceanfront Bliss at Hale Kona Kai 310 - A Cozy 1-Bedroom Retreat in Kailua Kona
Kona Town's historic “OCEAN VIEW MILE WALK”, with 24 Pacific Ocean view restaurants, multiple live entertainment venues, ocean front swimming beaches and charming shops, BEGINS AT YOUR FRONT DOOR.Enjoy ocean views, sounds and sweet fresh air breeze from your bedroom,...
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 is an unpretentious, laidback getaway in the heart of Princeville, perfect for couples looking to enjoy a tropical vacation without breaking the bank. Enjoy the king bed, open concept living, dining, and kitchen areas, and take in amazing views from either...
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!...
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...
Maui Resort Rentals: 6BR Retreat at Kaanapali’s Newest Luxury Residences, Steps from Beach & Resort Amenities!
This upscale 6BR retreat combines two 3BR villas from two neighboring buildings to create over 4000 sq ft of interior living space, perfectly suited for larger groups or families. Located on 38 beachfront acres within the popular Honua Kai Resort, your party will enjoy...
Kii Hale at Kukui ula Signature Retreat
Summary:Kii Hale at Kukuiula is a contemporary 4BR, 3BA residence offering a peaceful escape in one of Kauai’s most prestigious neighborhoods. With golf course vistas, a private heated pool, and open-air living spaces, this home invites relaxation in every corner. All...
Tropical Luxury Retreat W/ Infinity Pool, Spa & Outdoor Living!
Experience elevated Big Island living in this spectacular and serene island estate, ideally located within a premier resort setting. Picturesque bedroom suites feature private outdoor garden showers, creating a spa-like retreat surrounded by lush tropical beauty. The...
Enjoy stunning ocean views from Kaanapali Shores 544, a 1-bedroom retreat in Lahaina.
Kaʻanapali Shores 544 Enjoy Ocean Views from this Updated 1 Bedroom North Kaanapali Vacation Resort Condo, Steps to the Pool, Hot Tub and Beach Welcome to Your Maui Retreat: Kaanapali Shores 544 is a newly refreshed 1-bedroom, 1-bath condo perched on the fifth floor of...
Plantation Hale Resort Relaxing Kauai Retreat w Pool & Hot Tub
Summary:Highlights: Balcony- Steps to the Beach • 3 Pools & 2 Hot Tubs • Free Parking • Air-Conditioned Welcome to Sunny Plantation Hale, Your Bright & Breezy Kauai EscapeHale a cheerful, sunlit retreat —perfectly tucked beside the Coconut Marketplace and just a short...
Oceanfront 3BR Retreat with Stunning Views in Kahana
Discover the perfect island getaway at Kahana Outrigger #2B2, a spacious oceanfront 3-bedroom, 2-bath retreat nestled on Maui’s stunning west coast. This 1,448 sq ft condo offers breathtaking panoramic views of the Pacific from a large lanai, where you can whale watch...
Ohana Kai – Premier Luxury Retreat in Princeville
Welcom to Ohana Kai, Princeviile.Escape to your own private island retreat in the heart of Princeville, Kauai. This stunning 4-bedroom, 3.5-bath vacation home offers the perfect blend of tropical luxury, comfort, and space—ideal for families, groups, or anyone seeking a...
Paki Maui 222 Updated 2BD Oceanfront Retreat Steps from Pool & Hot Tub
Paki Maui 222 Freshly Updated Oceanfront 2 Bedroom Condo in the Heart of West Maui with Ocean Views Steps to the Pool and JacuzziWelcome to your Maui Retreat: This freshly updated oceanfront condo at Paki Maui offers a relaxed, comfortable place to settle in and enjoy...
Elegant luxurious hillside retreat with awe inspiring panoramic ocean and mountain views. 90 day minimum rental.
Nestled on the tranquil hillside of the distinguished Mahinui neighborhood, Hale Kalia is nothing short of a refined sanctuary where modern luxury meets island serenity.Nestled along the tranquil windward coast of O‘ahu, the Mahinui neighborhood in Kāne‘ohe offers a...