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Match: Private outdoor pool (unheated) Staffed property City breaks

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Price per night from

$263

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2 of 3 match: Private outdoor pool (unheated), City breaks, Staffed property

2 of 3 filters match

Price per night from

$194

Hale Kawehi B&B Guesthouse in downtown Hilo.

Hilo house

  • 1 bedroom
  • 2 bathrooms
  • sleeps 2

“Authentic, laid-back, non-touristy Hawaiian experience.” My husband and I just spent a week at Hale Kawehi. We loved every minute of it. Full disclosure: we both love cats and this charming Hawaiian home came with an especially loving tabby cat who greeted us every time we returned from an outing as soon as he discovered he was welcome. The house is much larger than the average guest house. It is charming and homey. It has a fully equipped kitchen and two covered patios where breakfast is a treat. Its location is central and easy to find as well as having easy access to local shops and restaurants. We were looking for a relaxed, non-touristy visit to get a sense of every day Hawaiian life and we achieved that goal well beyond what we might have hoped. Kawehi is a kind, generous and knowledgeable hostess. Lucky are those who choose Hale Kawehi. Anne Kass

2 of 3 match: Private outdoor pool (unheated), City breaks, Staffed property

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Price per night from

$189

Mika Kai - Blue Hawaii Oceanfront

Keaau house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

2 of 3 match: Staffed property, City breaks, Private outdoor pool (unheated)

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Price per night from

$981

Island Paradise Walk to Kealakekua Bay to see dolphins

Captain Cook house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

2 of 3 match: Private outdoor pool (unheated), City breaks, Staffed property

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Price per night from

$228

Pure blue water front condo- the west of world oahu-the old Hawaii life

Waianae apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

2 of 3 match: Private outdoor pool (unheated), City breaks, Staffed property

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Price per night from

$96

Living Aloha! Walk to Beach, Free Parking

Honolulu condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

2 of 3 match: Private outdoor pool (unheated), City breaks, Staffed property

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Price per night from

$155

Robertson's Beach House - Kailua Kona

Kailua-Kona house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

“Kinda Beach House” The house was well supplied for our group of eight. Everyone enjoyed the yard and access to the ocean. The turtles were a special hit. We appreciated the spacious lanai. Great sunset views. Neighborhood and road were busy, but not intrusively so. The downstairs bathroom off the kitchen could use a better privacy curtain.

2 of 3 match: Private outdoor pool (unheated), City breaks, Staffed property

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Price per night from

$1,311

Seaside Zen Cottage on the Beach in Kailua Kona

Kailua-Kona house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

“Great for family vacation. Awesome setting.” I was worried about this Beach House before renting but we would up loving it. The reviews seemed to range. There are some comments that the beach in front of house is small, yes the beach is small but it is also quite perfect for snorkeling, looking at or a quick dip. It was great sleeping to the sound of the ocean, the view is so nice you don't want to stop looking at it. One important note which it is hard to discover unless you stay here. The beach in front of the house is NOT your personal private beach, Visitors mostly locals and other renters visit the beach pretty much every day via a public walkway. There is a short wall separating you from the beach which is nice. It was never crowded it just has probably at most I have seen 10 people. The only issue with this is that it feels like your beach, but people keep coming to it. I got over this after the first day. The mornings and evenings the beach was usually empty and all to ourselves. The turtles come near you non stop at this beach which is really cool. The House upstairs is basically one giant room with 2 bathrooms, the rooms separate via closable walls which was convenient for us and well designed. The downstairs has a living area, kitchen and another bathroom. For our family this house was perfect. Something to note: There were lizards and occasional insects which appeared to be some kind of roach, however this did not bother us as a tropical hawaiian roach is not nearly as bad as a NYC roach. The furnishings of the house are in good shape, there are no frills in this house it is basically an older beach cottage. The house had beach gear and snorkeling gear available which was great. If you rent it, we left one of our little girls life jackets so you may see that there LOL. The place was clean with clean linens and towels. There is a property manager who lives on the grounds. She was very helpful. I would stay here again and would also recommend this house. I attached 3 pics. One is of the beach, There is sand you just can't see from the shot, two is from one of the rocks outside - house is on right, and 3 is of the sunset. Side note if you don't know anything about big island: Kona is where you want to be on the Big Island if you like nice weather. I did not realize there are basically two sides to stay. Kona side and Hilo Side. Luckily this is on Kona side. Hilo has a bunch of stuff to do and hikes, waterfalls, museums etc, also closer to volcanos but its the "rainy" side. I would rather be on the sunny side and travel to the other side.

2 of 3 match: Private outdoor pool (unheated), City breaks, Staffed property

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Price per night from

$918

2 of 3 match: Private outdoor pool (unheated), City breaks, Staffed property

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Price per night from

$281

Aloha Hawaiian Beach Condo In The Heart of Kona, Island of Hawaii

Kailua-Kona condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

“Good rental in the hart of Kona” Well equiped kondo, very clean and perfect located in the hart of Kona. Biggest disadvantage is the small kitchen. The pool is nice and the whirlpool great! Parking can be a problem when you arrive back from a trip after 5pm.

2 of 3 match: Private outdoor pool (unheated), City breaks, Staffed property

2 of 3 filters match

Price per night from

$194

Responds fast! avg. 1 hour 2 minutes

2 of 3 match: Private outdoor pool (unheated), City breaks, Staffed property

2 of 3 filters match

Price per night from

$366

KONA HAWAII GEM

Kailua-Kona condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

2 of 3 match: Private outdoor pool (unheated), City breaks, Staffed property

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Price per night from

$251

Beachfront Suite ~ Breathtaking ocean view Beach Villas at Ko Olina B802

Ko Olina condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 47 minutes

2 of 3 match: Private outdoor pool (unheated), City breaks, Staffed property

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Price per night from

$745

Spectacular Oceanfront Condo ~ Beach Villas at Ko Olina ~ End Unit O824

Ko Olina condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 1 hour 47 minutes

2 of 3 match: Private outdoor pool (unheated), City breaks, Staffed property

2 of 3 filters match

Price per night from

$716

“Wonderful time!” My husband and I had the opportunity to spend 10 days at Tracy's place and loved everyday! She has stocked everything needed to make it a worry free vacation. It was wonderful to watch the sunset each night from our place. Also, there are a bunch of delicious places to eat at nearby. It was nice to be able to bring home leftovers, to enjoy the next day. Highly recommend Tracy's place.

Responds fast! avg. 1 hour 2 minutes

2 of 3 match: Private outdoor pool (unheated), City breaks, Staffed property

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Price per night from

$332

“Incredibly relaxing!” It's a home away from home with everything you might need - with quality stuff too. Bright, beachy, quite and so relaxing.

Responds fast! avg. 1 hour 2 minutes

2 of 3 match: Private outdoor pool (unheated), City breaks, Staffed property

2 of 3 filters match

Price per night from

$355

Location, Location, Location! Elegant Waikiki Studio at Marine Surf

Honolulu apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

2 of 3 match: Private outdoor pool (unheated), City breaks, Staffed property

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Price per night from

$171

NEW Luxury Rental! Kahala Oceanside-6bed/6bath - Sleeps 14

Honolulu house

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 14

2 of 3 match: Staffed property, City breaks, Private outdoor pool (unheated)

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Price per night from

$4,013

Hilton Lagoon Tower

Honolulu condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 3 match: Private outdoor pool (unheated), City breaks, Staffed property

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Price per night from

$903

Hilton Lagoon Tower

Honolulu condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 3 match: Private outdoor pool (unheated), City breaks, Staffed property

2 of 3 filters match

Price per night from

$916

Hilton Lagoon Tower

Honolulu condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 3 match: Private outdoor pool (unheated), City breaks, Staffed property

2 of 3 filters match

Price per night from

$667

“Perfect Stay in Paradise!” Tracy's condo was perfect for our 30th wedding anniversary stay! We would not stay anywhere else on Maui except in one of Tracy's amazing rentals! The condo has a great location (across from the beach) and close to restaurants and shops. It is brightly decorated with happy cheerful colors and special touches! It was like a ray of sunshine! Both my husband and I loved the fact that the condo was well supplied --- everything from shampoo to an ice cooler and more. Tracy has thought of everything you need for a terrific stay --- even electric candles! The bed was so comfortable and relaxing! Tracy's binder on the coffee table was full of tips for a great vacation as well as menus from area restaurants. We loved seeing the large sea turtles swimming in the lagoon section at the beach across the street. The property is extremely clean and well maintained and we enjoyed the pool and jacuzzi at the condo as well. We were sorry to leave and return home. We can't wait to return to stay again at one of Tracy's Tropical Treasures condos! We enjoyed it so much that I have recommended it to a recently engaged friend for her honeymoon. Thank you Tracy for providing such wonderful accommodations and making our 30th wedding anniversary so memorable! We will definitely be back!

Responds fast! avg. 1 hour 2 minutes

2 of 3 match: Private outdoor pool (unheated), City breaks, Staffed property

2 of 3 filters match

Price per night from

$331

2 of 3 match: Private outdoor pool (unheated), City breaks, Staffed property

2 of 3 filters match

Price per night from

$523

Responds fast! avg. 1 hour 47 minutes

2 of 3 match: Private outdoor pool (unheated), City breaks, Staffed property

2 of 3 filters match

Price per night from

$945

1 of 3 match: Staffed property, Private outdoor pool (unheated), City breaks

1 of 3 filters match

Price per night from

$458

1 bdr, 1 bth 1296 sq ft house with whirlpool tub

Mountain View house

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

“Comfortable and Relaxing” This quaint home is located in a quiet and peaceful area of the Big Island. I found the house to be very clean and comfortable, with a special touch of lighting decor. A great whirlpool tub provided the ultimate relaxation that enhanced my stay! Everything I needed was there!

1 of 3 match: Staffed property, Private outdoor pool (unheated), City breaks

1 of 3 filters match

Price per night from

$103

A View to Die for! 3 bedroom 3 bath right on Waikiki Beach

Honolulu condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

2 of 3 match: Private outdoor pool (unheated), City breaks, Staffed property

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Price per night from

$2,058

Stunning Corner Unit 3BD OCEAN VILLA w/Ocean Views From All Rooms!

Kawela Bay villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 12

Responds fast! avg. 1 hour 38 minutes

2 of 3 match: Private outdoor pool (unheated), City breaks, Staffed property

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Price per night from

$1,274

Waikiki Beach Resort

Honolulu house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

Responds fast! avg. 1 hour 7 minutes

2 of 3 match: City breaks, Private outdoor pool (unheated), Staffed property

2 of 3 filters match

Price per night from

$3,439

Responds fast! avg. 3 hours 10 minutes

2 of 3 match: City breaks, Private outdoor pool (unheated), Staffed property

2 of 3 filters match

Price per night from

$287

1 of 3 match: Staffed property, Private outdoor pool (unheated), City breaks

1 of 3 filters match

Price per night from

$184

“"Lovely"” We stayed at Suite Aloha in September for 11 days. The room was spacious, airy and very comfortable. There was a huge ceiling fan to cool the entire room throughout the day and night. We were awakened by the sweet fragrance of plumeria as it floated through the windows every morning. Lovely! Sabine thought of everything to make our stay comfortable. We were welcomed with fresh fruit and a Beautiful arrangement of fresh Hawaiian flowers. There were beach items available for us to use including a beach umbrella, chairs, mats and beach bag. The location was ideal. We could easily walk to Kailua Beach or to Kailua town. Kailua town has plenty of upscale shops and restaurants. There was even a brand new Target there. We would definitely stay there again. It was lovely!

1 of 3 match: Staffed property, Private outdoor pool (unheated), City breaks

1 of 3 filters match

Price per night from

$108

2BR Private Home; Walk into the Heart of Lahaina Town!

Lahaina house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 3 match: Staffed property, Private outdoor pool (unheated), City breaks

1 of 3 filters match

Price per night from

$209

Rustic Cabin - Writer's Retreat in Volcano Hawaii

Volcano cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 3 match: Staffed property, Private outdoor pool (unheated), City breaks

1 of 3 filters match

Price per night from

$516

LUXURY BEACH HOME POOL EXCELLENT LOCATION

Kihei house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

“Wonderful stay in the perfect home. Great golf and beach locatio” My friends and I stayed in this high-end well-appointed home while we were on Maui. Our main purpose was to fit in as many games of golf as possible as our wives shopped and relaxed by the pools and enjoyed the beaches. This plan worked out perfectly since we were located right on golf course and a short walk from the beach. Everyone was more than happy with our accommodations and being able to rent a spacious home in the center of a luxury resort was ideal. This home was an exceptional value when you consider that most of the hotel rooms in the Wailea/Kihei area go for the same price for just one room. Everyone in our group felt as though this was our own home in Maui and we expect we will return again as soon as we can. We highly recommend this place and would like to thank the owners for extending us their every kindness. Sincerely, Don M

1 of 3 match: Staffed property, Private outdoor pool (unheated), City breaks

1 of 3 filters match

Price per night from

$5,555

1 of 3 match: Staffed property, Private outdoor pool (unheated), City breaks

1 of 3 filters match

Price per night from

$114

Waikiki Beach, Hawaii: One Bedroom, Two Bath Condo

Honolulu apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 5

Responds fast! avg. 1 hour 28 minutes

1 of 3 match: Staffed property, Private outdoor pool (unheated), City breaks

1 of 3 filters match

Price per night from

$258

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