Hawaii Retreat Vacation Rentals

Hawaii retreat vacation rentals offer peaceful escapes across the islands - perfect for wellness getaways, solo journeys, and romantic escapes. From secluded cottages to luxurious estates with ocean views, these properties provide a tranquil setting to relax, recharge, and embrace the Aloha spirit.

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Ko Olina Kai #17: Spacious, Stylish Retreat with Golf Course Views

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 prestigious 18th Fairway of the Ko Olina Golf Course, is a sanctuary of luxury and tranquility.

4 bedroom
3 bathroom
Sleeps 8

from $653

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$'The Aloha Green House' Retreat w\/ Ocean Views!$

'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 and Punalu'u Black Sand Beach.

2 bedroom
1 bathroom
Sleeps 6

from $222

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New Listing! Peaceful Poipu Retreat Waikomo 200

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 premier attractions.

1 bedroom
1 bathroom
Sleeps 4

from $397

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Heavenly Hawaii Retreat Home near Hilo, Ocean & Waterfalls

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 & outdoor areas to dine and relax, and all the essentials for a memorable stay.

4 bedroom
2 bathroom
Sleeps 13

from $743

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Ekahi Ocean Studio: Couples Retreat, Just 300 Feet To Keawakapu Beach

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.

1 bedroom
1 bathroom
Sleeps 2

from $702

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Peaceful Big Island Hawaii Retreat with Private Beach Club Access

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 use.

3 bedroom
3 bathroom
Sleeps 6

from $679

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$South Kauai Tranquil Retreat w\/ AC in Poipu$

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 variety of plants, and a koi pond.

1 bedroom
1 bathroom
Sleeps 4

from $455

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Beachfront Retreat with Stunning Ocean Views at Hale Pau Hana on Kam II Beach.

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 the ocean and air conditioning in every room makes this one of the most unique and sought after properties on Maui.

2 bedroom
2 bathroom
Sleeps 4

from $1,201

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$Hale Ohana: Kailua Retreat w\/hot tub, Tropical Pool, Walk to Beach$

Hale Ohana: Kailua Retreat w/hot tub, Tropical Pool, Walk to Beach

4 bedroom
3 bathroom
Sleeps 10

from $1,057

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Relaxing 4-Bedroom Farmhouse Retreat on Working Farm

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 from our sweet hens.

4 bedroom
2 bathroom
Sleeps 10

from $784

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Beach Front, Pool, Amazing Sunrise! Welcome to Oceanside Retreat At Kapaa, Kauai

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 20-steps away!

2 bedroom
1 bathroom
Sleeps 4

from $438

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Kihei Beach Retreat: Ocean Views and Sandy Feet!

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 gym.

2 bedroom
2 bathroom
Sleeps 6

from $453

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Walker's Lanikai Beach House – Historic Oceanfront Retreat

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).

5 bedroom
4 bathroom
Sleeps 14

from $2,976

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Lokelani B102 – Premium Oceanfront Retreat Steps from the Sand

Lokelani B102 – Premium Oceanfront Retreat Steps from the Sand

Experience the Elegance of Oceanfront Living at Lokelani B102 – Your Private Maui Escape

Step into your dream Maui getaway at Lokelani B102, a fully renovated beachfront sanctuary offering uninterrupted panoramic ocean views just steps from your private lanai.

2 bedroom
1 bathroom
Sleeps 3

from $305

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Stunning tropical retreat near the beach with pool, views & spacious lanai

Stunning tropical retreat near the beach with pool, views & spacious lanai

Ho'oka'ana Hale

Our calendar is updated in real-time & our nightly rates are accurately displayed. '

Live the luxe life at the top of Alii Heights! Surrounded by colorful blooms and palm trees, find yourself waking up every day in paradise.

3 bedroom
2 bathroom
Sleeps 6

from $462

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$Tropical Retreat in Paradise-steps from the Ocean! Newly remodeled with A\/C.$

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.

1 bedroom
1 bathroom
Sleeps 4

from $640

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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 spirit welcomes you to big blue skies punctuated by white clouds and palm trees kissed by the sun.

3 bedroom
2 bathroom
Sleeps 6

from $310

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Escape to Paradise: Family Retreat in Princeville at Hanalei, Kauai.

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 Accommodations: Spacious bedrooms with cozy bedding, perfect for restful nights after a day of adventure.

3 bedroom
2 bathroom
Sleeps 6

from $580

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$UALANI RETREAT. Spacious Ocean\/Mountain View Cottage.Private Tropical Sanctuary.$

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 2012/0001

Terrific Discounts Thru October.

2 bedroom
1 bathroom
Sleeps 4

from $276

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North Shore Villa - Relaxed Luxury Retreat

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 perfect blend of relaxed luxury and convenience, making it an ideal choice for a serene island escape.

1 bedroom
2 bathroom
Sleeps 4

from $638

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$NEW Listing - 1BD\/1BA Retreat Ideal for Couples, Golfers & Business Travelers$

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 resort community offers breathtaking views of Mauna Kea and the mesmerizing lava fields that surround the resort.

1 bedroom
1 bathroom
Sleeps 2

from $393

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Spectacular Executive Beachfront Retreat

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 Oahu's beautiful North Shore as you spot whales and turtles right in your backyard!

3 bedroom
3 bathroom
Sleeps 7

from $574

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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 location just a short walk to sandy beaches and a quick drive or bike ride to downtown Kona’s shops, dining, and attractions.

1 bedroom
1 bathroom
Sleeps 4

from $183

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Peaceful retreat with sunset & ocean views on the Waikoloa Village Golf Course!

Peaceful retreat with sunset & ocean views on the Waikoloa Village Golf Course!

Modern luxury right on the Waikoloa Village Golf Course! Our Hawaiian home was completely renovated in 2017, with a brand new kitchen featuring custom maple cabinets, quartz countertops, and stainless steel Bosch and LG appliances. All baths are completely new, with a huge custom shower in the primary bathroom, marble topped vanities, and high-end fixtures.

2 bedroom
2 bathroom
Sleeps 4

from $295

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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!

1 bedroom
1 bathroom
Sleeps 6

from $387

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Cool retreat at the entrance to Lanikai. Very Close to Beach. 3 Primary Bedrooms

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 with attention to detail throughout the rental.

3 bedroom
3 bathroom
Sleeps 8

from $583

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Hawaiian Treehouse, Peaceful Glamping Retreat

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. Conveniently located right between Hilo and VOLCANO NATIONAL PARK.

1 bedroom
1 bathroom
Sleeps 2

from $318

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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 families.

4 bedroom
2 bathroom
Sleeps 10

from $842

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New to VRBO. Air Conditioned Luxury Island Retreat - Newly Remodeled

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 and dining room.

2 bedroom
2 bathroom
Sleeps 4

from $784

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❤️PiH❤️ Sun Ray Retreat ★Ocean & Sunsets Views★Optional Mauna Kea Hotel Privileges

❤️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 surrounded by amazing sunset views of the Hawaiian coast.

3 bedroom
2 bathroom
Sleeps 6

from $676

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Beautiful 3 Bedroom Rainforest Retreat, minutes from HVNP

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 closeness to nature in a tasteful, understated setting.

3 bedroom
2 bathroom
Sleeps 6

from $282

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Puna Rainforest Hot Spring Retreat - Green Bamboo Cottage

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 surrounded by forest.

1 bedroom
1 bathroom
Sleeps 3

from $251

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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.

1 bedroom
2 bathroom
Sleeps 2

from $290

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$Charming Oceanfront retreat- Steps from the Beach, 2BR\/2BA Polo Beach Club 308$

Charming Oceanfront retreat- Steps from the Beach, 2BR/2BA Polo Beach Club 308

Immerse yourself in the tranquil sounds of the waves, our oceanfront condo offers the ultimate beach experience! Just steps away, you can enjoy wonderful swimming and snorkeling, and even spot turtles on the beach. Take in the beautiful ocean views, watch for whales (in season), and sip a fresh cup of Kona coffee on the lanai.

2 bedroom
2 bathroom
Sleeps 4

from $975

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Tropical designer retreat right on the water with ocean view, pool & AC

Tropical designer retreat right on the water with ocean view, pool & AC

Puu Poa 101

Our calendar is updated in real-time & our nightly rates are accurately displayed. '

Spend your vacation enjoying the salty sea air and ocean views from the spacious lanai and nearly every room inside this completely renovated two-bedroom suite.

2 bedroom
2 bathroom
Sleeps 4

from $888

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Emmalani Hale, a luxurious and tranquil retreat, AC, nestled in Princeville

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, this beautiful home creates a serene and sophisticated atmosphere the moment you arrive.

3 bedroom
3 bathroom
Sleeps 8

from $578

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Ohia Cottage: Your Coastal Retreat near Napoopoo Beach

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.
Our cottage is a perfect setting to host honeymooners celebrating their love or simply hosting a family of 3 that would love a secluded getaway in the tropics!

2 bedroom
1 bathroom
Sleeps 3

from $321

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$Large Family Retreat on Calm Swimming Beach, A\/C$

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. ft. home is comfortable and luxurious, with three of the four large bedrooms boasting en-suite baths. Featuring a large wrap around second-story lanai, and another large outdoor oceanfront lanai with loungers, BBQ, hot/cold outside shower, and dining table, the glorious ocean and mountain views won't disappoint as you use the ample space to enjoy your surroundings!

5 bedroom
4 bathroom
Sleeps 10

from $1,199

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2.7 Acres of Exceptional, Secluded Retreat - Close to Beach & Shopping!

2.7 Acres of Exceptional, Secluded Retreat - Close to Beach & Shopping!

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 2012, the Hideaway is composed of 4 separate buildings linked to create a delightful courtyard perfect for breakfast smoothies.

3 bedroom
3 bathroom
Sleeps 6

from $560

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Luxury Upcountry retreat with breathtaking views!

Luxury Upcountry retreat with breathtaking views!

Permits
BBMP2019/0006 & SUP2 2019/0003
GE-081-730-0480-01 & TA-081-730-0480-01
This is a BnB not a STRH
Owners live on property.

Aloha, sorry but at this time we are not hosting to families with children younger than 16. Mahalo.

1 bedroom
1 bathroom
Sleeps 2

from $601

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Hilo Studio Retreat with Gorgeous Park View, AC, WiFi, Pool

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.

1 bedroom
1 bathroom
Sleeps 2

from $165

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Villa Frangipani Tropical Beachside Retreat Kailua

Villa Frangipani Tropical Beachside Retreat Kailua

About this space
Once 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.

4 bedroom
4 bathroom
Sleeps 8

from $609

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EXTRAORDINARY Hale Kuikahi Oceanfront Retreat - fully airconditioned!

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 room in the house.

4 bedroom
3 bathroom
Sleeps 8

from $775

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Maui Breeze Retreat at Ho'olei openings Jul 19-29, Aug 22-Sep 14 & Sep 25-Oct 11

Maui Breeze Retreat at Ho'olei openings Jul 19-29, Aug 22-Sep 14 & Sep 25-Oct 11

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 landscapes showcasing Maui’s brilliant tropical foliage.

3 bedroom
3 bathroom
Sleeps 8

from $1,373

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HALE KE`PUA! Princeville Tranquil Jungle Retreat!

HALE KE`PUA! Princeville Tranquil Jungle Retreat!

Welcome to Hale Ke' Pua, (House of Flowers) our spacious, serene space on the beautiful North Shore of Kauai. Your private area on the bottom floor within the home has its own private entrance, bedroom, full bath, living room, kitchenette, BBQ and gorgeous lanai with lush garden views.

1 bedroom
1 bathroom
Sleeps 2

from $471

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Ohana Retreat - The Real Hawaiian Experience

Ohana Retreat - The Real Hawaiian Experience

Experience the Beauty of Hawaii at Ohana Retreat

Ohana Retreat is the ultimate getaway for large families looking to embrace the breathtaking beauty of Hawaii. Our spacious island-style home features eight luxurious bedroom suites, each complete with a private bath, wet bar, refrigerator, and private deck.

8 bedroom
8 bathroom
Sleeps 18

from $1,534

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Discover the ultimate Hawaiian retreat at Kanaloa Condominium

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 the lush landscape and the views of The Kona Country Club Golf course from your private lanai.

3 bedroom
3 bathroom
Sleeps 8

from $516

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Natural Light End Unit Kuilima East Steps to Pool-BBQ-Parking Golf Retreat

Natural Light End Unit Kuilima East Steps to Pool-BBQ-Parking Golf Retreat

Book with confidence! This property is professionally managed by Ali'i Beach Rentals, an award-winning property management company.

This property is a new addition to our inventory. Rest assured, we can confidently say that this property is truly amazing.

2 bedroom
2 bathroom
Sleeps 6

from $675

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**Fairways Mauna Lani #1606 - Luxurious 2-Bedroom Retreat: 2 King beds, Remodele

**Fairways Mauna Lani #1606 - Luxurious 2-Bedroom Retreat: 2 King beds, Remodele

**
Please scroll down for detailed information

Welcome to your dream getaway! This beautifully remodeled 2-bedroom, 2-bathroom townhome is designed with relaxation and comfort in mind. Spacious and open layout that feels like home from the moment you enter.

2 bedroom
2 bathroom
Sleeps 4

from $431

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$Ground-Floor Retreat W\/Ocean Views-Kiahuna 2166$

Ground-Floor Retreat W/Ocean Views-Kiahuna 2166

Kiahuna Plantation unit 2166: This modern tropical one-bedroom ocean view unit on the ground floor is a rare find and provides the utmost comfort with cool flooring and decorative carpeting, two cooling ceiling fans, and floor-to-ceiling windows allowing for plenty of natural sunlight and scenic ocean views.

1 bedroom
1 bathroom
Sleeps 4

from $669

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