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Holiday Rentals with Pools in Kailua-Kona

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895 rentals in Kailua-Kona.
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Alii Magic Sands Vacation Rental 3 min walk to Beach
62 reviews
1 bedroom
1 bathroom
Sleeps 2
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2 bdrm 2 ba condo across from White Sands Beach
40 reviews
2 bedrooms
2 bathrooms
Sleeps 4
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A Perfect 10 *** Ocean View Pool Waterfall Hot Tub
6 reviews
5 bedrooms
5 bathrooms
Sleeps 13
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Beachfront Oceanview, 2 bedroom 2 bath, Sleeps 6
18 reviews
2 bedrooms
2 bathrooms
Sleeps 6
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Kailua Kona Oceanview - Keauhou Akahi
7 reviews
1 bedroom
2 bathrooms
Sleeps 6
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KKSR3202 DIRECT OCEANFRONT, Spacious, 2nd Flr
12 reviews
2 bedrooms
2 bathrooms
Sleeps 6
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Oceanfront Kona Condo w/Lanai, Walk to Beach!
2 bedrooms
2 bathrooms
Sleeps 4
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Holualoa Bay Villas: 106 Beautiful Oceanview, AC, Elevators, Wifi!
3 reviews
2 bedrooms
2 bathrooms
Sleeps 6
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The Magic Sands olukai Cabana Kailua Kona, Hawaii - 1500 sq ft
3 bedrooms
2 bathrooms
Sleeps 6
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Kahaluu Bay Across from Snorkel Beach - Ocean View
4 reviews
2 bedrooms
2 bathrooms
Sleeps 6
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Amazing Ohana Retreat on the Big Island 8 bedrooms
27 reviews
8 bedrooms
9 bathrooms
Sleeps 18
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‘Living Aloha’ Condo w/ 2 Master Suites & A/C!
2 bedrooms
2 bathrooms
Sleeps 5
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Aloha Romantic Hawaiian Beach Condo Downtown Kona
7 reviews
1 bedroom
1 bathroom
Sleeps 2
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Dual-Suite Escape | AC, Ocean & Sunset Views | Oceanfront Pools, Spa & Tennis
2 bedrooms
2 bathrooms
Sleeps 6
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Hawaiian Paradise, Kona Isle, Ocean Front Complex. Rates starting at $90 a night
1 bedroom
1 bathroom
Sleeps 2
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Kailua-Kona Apartment w/ Pool, Deck & Ocean Views!
1 review
2 bedrooms
1 bathroom
Sleeps 5
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Kona Isle C28. Corner Unit, 2nd Floor, Ocean Views, & Air Conditioning!
1 bedroom
1 bathroom
Sleeps 4
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Palm Hale - King Palm
2 reviews
1 bedroom
1 bathroom
Sleeps 2
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Kahaluu Beach, OCEAN VIEWS, The Best Snorkeling & Surfing, SUPER CLEAN
14 reviews
2 bedrooms
2 bathrooms
Sleeps 6
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KONA REEF D-32: Absolute Oceanfront, Top Floor, Private
1 bedroom
1 bathroom
Sleeps 4
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Surf and Racquet 1201 2/2 Oceanfront
8 reviews
2 bedrooms
2 bathrooms
Sleeps 4
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Surf and Racquet 5102 2/2 oceanfront
2 reviews
2 bedrooms
2 bathrooms
Sleeps 4
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Kanaloa 1703 3BR Oceanfront
3 bedrooms
2 bathrooms
Sleeps 6
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Country Club Villas 110 2/2 Oceanview
1 review
2 bedrooms
2 bathrooms
Sleeps 4
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306-AirCon. Upgraded Corner Unit w/Expansive Ocean Views and Extra Large Lanai.
63 reviews
2 bedrooms
2 bathrooms
Sleeps 6
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OceanView Plumeria Suite, kitchenette,Sprechen Deutsch. Bears' Place Guest House
50 reviews
1 bedroom
1 bathroom
Sleeps 4
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KONA ISLE - Truly Unique Oceanfront/Garden Condo
49 reviews
1 bedroom
1 bathroom
Sleeps 4
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Great Ocean Views! 2007 Built Penthouse at Kahaluu
38 reviews
2 bedrooms
2 bathrooms
Sleeps 6
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Fabulous Ocean Views! 2005 Built 3-Bed at Kahaluu
32 reviews
3 bedrooms
2 bathrooms
Sleeps 6
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Amazing Kona Oceanfront Private Home, 2 Bedroom + bonus room, 3 bath, sleeps 8
28 reviews
4 bedrooms
3 bathrooms
Sleeps 8
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Carson's Mountain Cabin with hot tub and fireplace! Special winter deal....
22 reviews
1 bedroom
1 bathroom
Sleeps 4
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Seaside Zen Cottage on the Beach in Kailua Kona
22 reviews
3 bedrooms
3 bathrooms
Sleeps 6
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Plantation Manager's Beach House - Kailua Kona
30 reviews
4 bedrooms
4 bathrooms
Sleeps 8
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Sunsets & Surfers - Kona Reef Ocean Front Unit
39 reviews
1 bedroom
1 bathroom
Sleeps 4
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Spacious Retreat in Kona
28 reviews
1 bedroom
1 bathroom
Sleeps 2
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12/20-12/26 Available!!! Ahhh.... PARADISE ~Fab OCEAN VIEW, Snorkel, Surf,Bike
114 reviews
2 bedrooms
2 bathrooms
Sleeps 6
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BEAUTIFUL Beachfront / Top Floor / Air Con / Walk to Town
84 reviews
1 bedroom
1 bathroom
Sleeps 2
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Elegant Private Kona Oceanfront Hawaiian Beach House directly on Kahaluu Bay
83 reviews
3 bedrooms
3 bathrooms
Sleeps 6
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Wow! Awesome Kailua Ocean View and Convenient Too!
76 reviews
2 bedrooms
2 bathrooms
Sleeps 6
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Best of Kona: pool, hot tub, walk to ocean, free wifi, newly remodeled
66 reviews
3 bedrooms
2 bathrooms
Sleeps 8
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Paradise isn't lost, it is here in KAILUA-KONA
76 reviews
2 bedrooms
3 bathrooms
Sleeps 6
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Hawaii County Certified! Hale Hina - Perfection in Paradise!
98 reviews
3 bedrooms
3 bathrooms
Sleeps 8
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Oceanfront - Kanaloa at Kona - Newly Remodeled
85 reviews
2 bedrooms
2 bathrooms
Sleeps 4
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Gorgeous remodeled condo Oceanfront! SUNSET!
54 reviews
1 bedroom
1 bathroom
Sleeps 2
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SPECIAL FOR 2021! BREATHTAKING OCEAN VIEWS DELUXE 1/1 CASA DE EMDEKO B#135
171 reviews
1 bedroom
1 bathroom
Sleeps 4
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Kona Oceanfront Top Floor Condo 30ft from Shore - Amazing View, Wifi, A/C
114 reviews
2 bedrooms
2 bathrooms
Sleeps 4
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Direct Ocean View : Top Floor : End Unit : Wrap-Around Lanai : 5* Reviews
73 reviews
2 bedrooms
2 bathrooms
Sleeps 4
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Breathtaking Kona Home - Heated Pool / Air conditioning and Beautiful Sunsets
73 reviews
4 bedrooms
2 bathrooms
Sleeps 8
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Direct Oceanfront, Big Wave Penthouse-1,200 sq ft, Stunning View. Free,fast WiFi
128 reviews
2 bedrooms
2 bathrooms
Sleeps 6
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WINTER SALE! PEGGYS PENTHOUSE, OCEAN/SUNSET/SURFER VIEW ,BEACH GEAR bucket list
149 reviews
1 bedroom
1 bathroom
Sleeps 4
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