Hawaii Retreat Vacation Rentals

Hualalai Hillside Penthouse Oceanview Retreat

One of only seven Hualalai Penthouse Villas. Upper-level Villa featuring single level interior with over 4,200 sq feet of living and lanai space. Hear the sounds of the Pacific Ocean while enjoying the beautiful close unobstructed ocean and beach views from the generous...

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...

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...

Romantic Ambiance of 'OLD Hawaii'. Ground Floor, Clean, Beach Gear Included

*About the Property*Welcome to your Maui home away from home! Our family-owned and operated condos have been lovingly cared for by our ohana for over 50 years. We personally live on island and treat each unit with the same attention, care, and aloha we give our own...

6 mins from Nat'l Park! Enjoy the sound of rain & birds in a peaceful retreat.

Hawaii State Tax ID: 148-388-6592-01. Hawai'i County IDs: STVR 19-345557, NUC 19-293Aloha! E komo mai. Welcome to Fern Cottage. Located across from Volcano Village, and just minutes from Hawaii Volcanoes National Park, we invite you to make our fully permitted house...

Seabreeze Retreat-Recently REMODELED-5 Star Reviews

This beautifully decorated deluxe three bedroom condo is situated in the heart of Waikoloa Beach Resort. With no units above or below, the condo offers the most in privacy. It is newly professionally decorated in Ocean colors with granite and stainless steel appliances....

Ocean view home on beautiful Sugar/Kihei Beach - PERMIT #STKM 2015/0003

Over 150 glowing reviews and counting. This beachfront gem is the perfect retreat for families, couples, or groups seeking space, comfort, local feel (not touristy) and unbeatable central location.Property Highlights:Spacious 3-bedroom, 2.5-bath home with optional...

AS SEEN on TV- Rated #1 Northshore Rental/Retreat with the "Wow" Factor

IF YOU'RE PINING FOR A LUSH, LAZY, LANGUID ESCAPE...A BAREFOOT TRANQUILITY...A BALMY, PALMY, SEA-SCENTED ADVENTURE...LOOK NO FURTHER!!Rated #1 Because...1. AS SEEN ON TV - The Discovery Channel recently filmed our home, Hale Mana, for the premier episode of a new TV...

Forest Retreat Eco-Lodge - 24 acres of private land.

Picture Shangri La with rolling mists and sunshine over the canopy of Ohia Lehua with the tip of Mauna Kea poking through the valleys off in the near distance...Ahu Lani Retreat Center is an educational and retreat facility located at 3,000 feet elevation on the Hamakua...

Cozy Tropical Retreat Guest House with AC

Our Tropical Retreat Guest House is a luxurious 1 bedroom, 1 full bath resort-style guest house located in one of Hilo’s premier subdivisions. Our guest house is truly a tropical paradise with a very spacious living area. The guest house opens up to a beautiful...

Poipu Tropical Retreat with A/C & Pool/Gym Access

Discover beautiful Kauai from this spacious 1 bedroom vacation home (built in 2018) in the heart of sunny Poipu. Located in Poipu Beach Estates, the newest upscale neighborhood bordering the Kiahuna Golf Course, that is just minutes from the best beaches on Kauai,...

Panoramic Ocean Views • Private Pool + Spa • 4BR Kona Retreat Sleeps 10

Welcome to your private Kona retreat — where panoramic 180° ocean views, unforgettable sunsets, and relaxed indoor-outdoor living define your stay.This spacious 4-bedroom, 4.5-bath home comfortably sleeps up to 10 guests and is ideal for families or groups traveling...

Stunning distinguished villa with tranquil views

Kapalua Golf Villa 18V4 is a 1-bedroom, 2-bathroom villa that accommodates 2 guests and just completed a full remodel in December 2022. Feel at ease when arriving through your private entrance, welcoming you into a beautiful and bright living room boasting brand new...

Pakala Beach Estate: Island-Style Retreat on Kauai's West Shore

Rates shown are for 8 guests; additional guests up to maximum of 11 are $20/night each. This magnificent, island-style estate truly exceeds all expectations. Located on secluded Pakala's Beach on Kauai's west side, this totally serene property borders an orchard and is...

Walker's Lanikai Beach House – Historic Oceanfront Retreat

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-1757. It is compliant with Hawaii State Legislation (HB2078) for vacation rental accommodations,...

Private, Pet-friendly, Newly Renovated Rainforest retreat close to Waikiki.

Welcome to our fully renovated (2024) 2B/1B free-standing guest house! Walk to Manoa Falls, community pool, courts (tennis, pickleball), and wellness classes. Full shopping center (groceries, dining, banks) is in the valley. We allow pets & long-term stays. Quick access...

May Cancellation Discounts available. Island Retreat Spacious 3B 3B home.

Aloha and e komo mai (welcome) to Hale Alana, your oasis in Wailea, Maui. Please contact us for seasonal discounts and special rates!Step into Hale Alana, a Polynesian-inspired home situated on a 1/2 acre tropical paradise. With three inviting bedrooms, two being...

Ocean Front Beachside Beauty. Two Free Rounds of Golf*

*SPECIAL - 2 Free Rounds of Golf at the King Kamehameha Golf Club, Maui's Premiere Private Club. On Stays of 5 nights or more. Looking for a great Honeymoon, Anniversary or Vacation of a Lifetime. Our 1 bedroom condo is just the right place for you! King Bed with luxury...

Romantic, Luxury, Sensual Retreat - Couples Only

Welcome to The Palms at Wailea – Your Island Paradise Awaits! Located in the prestigious Wailea resort community, The Palms at Wailea condo complex stands out as one of Maui's most elegant destinations. Our 1-bedroom, 2-bathroom condo (Unit #1603) has been custom...

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...

Volcano Off the Grid Eco Cabin Retreat in the heart of the tropical raiforest.

The Volcano Eco Cabin is situated on six acres of a private young Ohi'a forest, adjacent to the Volcano National Park. Only 5 miles from the main entrance, at the Elevation of 2400 feet the cool mountain breeze provides natural air-conditioning and escape from the...

Wonderful retreat, Fantastic View, Immaculate, Beautiful, Private and Peaceful!

Enjoy gorgeous unobstructed ocean, marina & mountain views from our beautiful guest house. Located on the ridge, in a safe, quiet and upscale neighborhood in Hawaii Kai, East Honolulu, just around the corner from famous Hanauma Bay, Halona Blow Hole, spectacular Sandy...

Puako Pau Hana, A Restful, Private Retreat located steps from the water!!

Puako Pau Hana is a great place to escape from all your cares! Located in the heart of Puako, you are literally just a few steps to the most beautiful little beach in Puako! Puako is known for it's magical old fashioned neighborhood feel and remarkable clear water,...

Charming Ocean View Home with Central A/C - walk to Downtown Paia and Beaches

Experience the beauty of Maui’s North Shore from this private, ocean-view home just minutes from downtown Paia and some of Maui’s best beaches. This spacious 3-bedroom, 2-bath vacation rental offers the perfect balance of tranquility and convenience, featuring central...

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:• Comfortable...

Family Retreat in Mākaha Valley | Sleeps 14 + Beach Gear

Come experience authentic Hawaiian hospitality at Makaha Valley Hale Kai, a property proudly owned and managed by a local resident. By staying with us, you are directly supporting the local community. This 4-bedroom, 3.5-bath retreat sleeps up to 14 and blends the ease...

O-523 Sunset Hale Retreat - Ko Olina Beach Villa. Steps to the Pool and Beach!

Welcome to our Sunset Hale Retreat - Ko'olina Beach Villa. Steps to the pool and beach!Amazing beachfront condo in the Ko'Olina resort overlooking swimming pool with beautiful pool and sunset views! Pristine residence features spacious living area and lanai with pocket...

Puamana 177-3 – Elegant Garden Retreat in South Puamana

Escape to the tranquil beauty of Puamana in this tastefully remodeled 2-bedroom, 2.5-bathroom townhome, ideally located in the lush, tropical oasis of South Puamana—untouched by the 2023 Lahaina fire. This peaceful location offers quick access to the nearby beach,...

Oceanfront retreat with breathtaking ocean views

Discover the beauty of Maui from Hale Mahina A205, a second-floor, 1-bedroom, 1-bathroom condo that offers a comfortable and memorable island retreat. Designed to sleep up to 4 guests, this spacious, open-concept unit invites you to unwind and enjoy the best of...

Charming Condo with AC/Saltwater Pool/HotTub, Close to the Best Beaches and Golf

Step inside your tropical home away from home with convenient keyless entry. The bright, open-concept living space is perfect for relaxing after a day of adventure.LIVING AREA: - Comfortable sofa (pulls out to a queen bed with memory-foam mattress) and an oversized...

White Sands Village 315 - Top Floor - Ocean Views

Hello ocean views! You can watch the sun sink into the ocean every night from your private lanai off this inviting top-floor condo. From this vantage point, you’ll get spectacular views of the sunsets and be able to hear the crashing of the waves on the beach below....

Hale Malie - a peaceful rainforest retreat minutes from Volcano National Park!

Hale Malie is a charming 1-bed/1-bath cottage retreat on a private half acre of lush Hawaiian rain forest just minutes from Volcano National Park. Featuring vaulted ceilings, a full kitchen, a sunny dining area, and expansive covered lanai, this cottage is ideal for two...

Hawaiian Family Paradise Retreat – Near Beach & Golf!

Escape to your paradise in this luxurious Hawaiian retreat! This exquisite home offers the perfect blend of relaxation and convenience. Just minutes from the Kohala Gold Coast’s finest beaches and resorts, a short walk to local shops, restaurants, a community pool, and...

Luxurious 2BR/2BA in Poipu, Kauai: Island Paradise Awaits at Nihi Kai 507

Welcome to Your Tropical Retreat at Nihi Kai 507!Step into relaxation and luxury in this beautifully remodeled and professionally decorated 2BR/2BA split-level condo, one of the most sought-after spots in Poipu. With air conditioning throughout and thoughtful upgrades...

Oceanfront Gated Estate Retreat - Banyan Tree B&B Suite w/ Horses-Beach 10m Walk

Aloha and welcome to our Hawaiian Celebration, our Ho'olaule'a. Hale Laule'a at Opihi Point is a +l$10+M, one-of-a-kind, World Class, 5-acre private, Estate Retreat sitting on the cliff edge of the Pacific Ocean with an unmatched view of the Hamakua Coast. Hale Laule'a...

Island Chic - Zen Retreat - A/C in 2 Bedrooms

Welcome to your modern haven of island living, where sleek design and thoughtful amenities converge to create a stylish retreat. This residence boasts not one but two master suites, a well-appointed guest room, a private office with a sleeper sofa and a range of...

Kahala 414 - Private Two-Bedroom Condo in Poipu Kai

Summary:Ground-floor two-bedroom retreat in Poipu Kai Resort, just a short walk to Poipu Beach, Brennecke’s, Shipwreck Beach, and nearby dining and shops. Features two king bedrooms, portable A/C in the primary suite, a private lanai, full kitchen, beach gear, and...

Villa Maluhia with AC, views!, watch baby albatross play in your front yard

Welcome to Villa Maluhia, a fully renovated 1br/1ba nestled in the serene beauty of Hawaii’s Garden Isle. Situated in the prestigious Kamahana Princeville community, this downstairs unit offers panoramic ocean views and golf course views at the end of a quiet road where...

Luxurious 2BR Mana Kai Retreat: Panoramic Ocean Views, Modern Amenities

Absolutely stunning, fully remodeled vacation rental with panoramic ocean and island views! Get ready to experience a truly luxurious tropical getaway in a location that will leave you breathless. Here are the incredible features of our rental:Panoramic Ocean and Island...

Family-friendly condo near Kihei and Wailea

Maui Vista 2413 is a two-story, 2-bedroom, 2-bathroom condo offering amenities like air-conditioning, a washer/dryer, and a private lanai. Located on the fourth floor, this spacious unit accommodates up to 7 guests, featuring a California King bed in the master bedroom,...

Island retreat with a pool, BBQ access, private lanai, washer/dryer, central AC

Kauai Kailani 109Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Aloha paradise! This beautiful Kauai Kailani property features all of the amenities you love to have while on...

Updated ocean view retreat near Poipu Beach; A/C, pool, gym and restaurants.

A Perfect Day in Paradise...Greet the morning with freshly brewed coffee on your spacious lanai with expansive garden and ocean views from this top floor unit. Making breakfast is easy in your bright, beautiful open kitchen with stainless steel appliances. Then pack up...

Kailua Beach Oceanfront Estate – Grand 6-Bedroom Retreat on Oahu’s Shores

This property is professionally managed by Private Homes Hawaii, LLC, a licensed brokerage in the State of Hawaii (RB-21170). It is licensed as a short term vacation rental, Non-Conforming Use Permit Numbers 1990/NUC-1777/1778 and is compliant with Hawaii State...

Kehena Beach Oceanfront Retreat - Incredible Views of Ocean w/Heated Swimspa

Discover the ultimate oceanfront retreat on the Big Island at Kehena Cliffside Estate — a private, gated luxury rental designed to showcase breathtaking views of the Pacific Ocean from nearly every room. Nestled along the dramatic cliffs of Kehena, this spacious...

Heavenly Hawaii Retreat Home near Hilo, Ocean & Waterfalls

Welcome to the perfect Hawaii Homebase for you & your family-friends! Enjoy tons of space and privacy in this gorgeous, pet friendly, 4BR/2BA fully appointed home on a five acre fruit farm, designed for up to 13 guests. This retreat offers ocean views, various indoor &...

NEW! Ocean View Hawaii Vacation And Event Retreat

Welcome to our breathtaking vacation rental on the Big Island of Hawaii! Nestled amidst stunning natural beauty, this magnificent property boasts not one, but two panoramic homes, providing the perfect getaway for larger groups, family vacations, retreats, and special...

Puna ZEN Botanical Garden Retreat near Volcano Nat. Park, Hilo, Kehena Beach

Escape to a charming traditional Hawaiian home, elevated on post and pier for enhanced airflow and privacy. This unique blend of classic architecture and mid-century design features an open-concept great room, complete with a sunken living area, dining space, and...

Private Ocean View Retreat 5 Min to Kona & Beach with refreshing AC

A refined blend of luxury and island living near Kailua-Kona. Welcome to Hale Ulu (House of Growth). Perfectly located just 5 minutes from town and the ocean, this private retreat offers breathtaking ocean views and is wrapped in lush tropical Hawaiian greenery....

Deluxe Ka'anapali Condo with AC Luxurious Retreat

**Kaanapali Plantation #16 – Your Peaceful Island Getaway**Welcome to Kaanapali Plantation #16, your serene island retreat with expansive views of lush landscapes, the Royal Kaanapali Golf Course, and the islands of Lanai and Molokai, all framed by the stunning blue...

Direct Ocean Front, Incredible Views, Perfect Couples Getaway, Split AC

Perched just 50 feet from the tranquil shoreline of scenic Maalaea Bay, Maalaea Kai 311 offers one of the most sought-after oceanfront escapes in Maui. Floor-to-ceiling views from the private lanai showcase uninterrupted swaths of blue Pacific water, where sea turtles...