Hawaii Holiday Rentals
1176 Hawaii Holiday Rentals were found matching your criteria. These vacation rentals are presented by their owners or managers. Please click on the photos or links below, then contact them directly with your inquiries. Use the search criteria box on the left of the page to refine your search within Hawaii, United States.
Get all the information you need about your Hawaii vacation rental. (We also have vacation rentals in other parts of the United States and around the world.)
Get all the information you need about your Hawaii vacation rental. (We also have vacation rentals in other parts of the United States and around the world.)
Select a location to narrow your vacation rental search or browse listings below:
Hawaii Top Cities
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Condo:
2 Bedroom, 2 Bathroom, Sleeps 6
Location: Kailua-Kona, Hawaii, United States
Description: Come and enjoy this community at the Kona Makai, vacationers number one choice for return guests. The Kona Makai offers guests lovely lush grounds,... Learn More
Location: Kailua-Kona, Hawaii, United States
Description: Come and enjoy this community at the Kona Makai, vacationers number one choice for return guests. The Kona Makai offers guests lovely lush grounds,... Learn More
Rates
$150 - $195 night
$1050 - $1365 week
$150 - $195 night
$1050 - $1365 week
Featured
Condo:
2 Bedroom, 1 Bathroom, Sleeps 6
Location: Honolulu, Hawaii, United States
Description: Enjoy a beautiful fully furnished Condo in the heart of Waikiki only two blocks from the world famous Waikiki Beach. The condo has a full kitchen i... Learn More
Location: Honolulu, Hawaii, United States
Description: Enjoy a beautiful fully furnished Condo in the heart of Waikiki only two blocks from the world famous Waikiki Beach. The condo has a full kitchen i... Learn More
Rates
$175 - $275 night
$1200 - $1800 week
$175 - $275 night
$1200 - $1800 week
Featured
Condo:
1 Bedroom, 1 Bathroom, Sleeps 6
Location: Ohua, Hawaii, United States
Description: Amazing location! Right in the heart of Waikiki , you are walking distance to all the classy boutiques, trendy shops, outstanding restaurants, & po... Learn More
Location: Ohua, Hawaii, United States
Description: Amazing location! Right in the heart of Waikiki , you are walking distance to all the classy boutiques, trendy shops, outstanding restaurants, & po... Learn More
Rates
$150 - $300 night
$1050 - $1800 week
$150 - $300 night
$1050 - $1800 week
Condo:
2 Bedroom, 2 Bathroom, Sleeps 5
Location: Wailea, Hawaii, United States
Description: People who know Hawaii know that Wailea, Maui is a very special place. People who know Wailea know that Wailea Elua is one of Wailea’s premier beac... Learn More
Location: Wailea, Hawaii, United States
Description: People who know Hawaii know that Wailea, Maui is a very special place. People who know Wailea know that Wailea Elua is one of Wailea’s premier beac... Learn More
Rates
$425 - $595 night
$2975 - $4165 week
$425 - $595 night
$2975 - $4165 week
Condo:
2 Bedroom, 2 Bathroom, Sleeps 6
Location: Wailea, Hawaii, United States
Description: Makena Surf Resort is a luxurious secluded beachfront condominium located in exclusive Makena Resort. This gated community was developed with six 2... Learn More
Location: Wailea, Hawaii, United States
Description: Makena Surf Resort is a luxurious secluded beachfront condominium located in exclusive Makena Resort. This gated community was developed with six 2... Learn More
Rates
$396 - $640 night
$2772 - $4480 week
$396 - $640 night
$2772 - $4480 week
Villa:
3 Bedroom, 2 Bathroom, Sleeps 8
Location: Kahuku, Hawaii, United States
Description: Photographs are of one of my actual 3-bedroom vacation villas. I have three identical ocean front, direct ocean view 3-bedroom villas that you can... Learn More
Location: Kahuku, Hawaii, United States
Description: Photographs are of one of my actual 3-bedroom vacation villas. I have three identical ocean front, direct ocean view 3-bedroom villas that you can... Learn More
Rates
$399 - $699 night
$2793 - $4613 week
$399 - $699 night
$2793 - $4613 week
Condo:
2 Bedroom, 2 Bathroom, Sleeps 4
Location: Wailea, Hawaii, United States
Description: Makena Surf Resort #B-205 is a luxurious secluded beachfront condo located in exclusive Makena Resort. This gated community was developed with six ... Learn More
Location: Wailea, Hawaii, United States
Description: Makena Surf Resort #B-205 is a luxurious secluded beachfront condo located in exclusive Makena Resort. This gated community was developed with six ... Learn More
Rates
$511 - $745 night
$3577 - $5215 week
$511 - $745 night
$3577 - $5215 week
Condo:
2 Bedroom, 2 Bathroom, Sleeps 4
Location: Wailea, Hawaii, United States
Description: Makena Surf Resort is a luxurious secluded beachfront condominium located in exclusive Makena Resort. This gated community was developed with six 2... Learn More
Location: Wailea, Hawaii, United States
Description: Makena Surf Resort is a luxurious secluded beachfront condominium located in exclusive Makena Resort. This gated community was developed with six 2... Learn More
Rates
$396 - $640 night
$2772 - $4480 week
$396 - $640 night
$2772 - $4480 week
Home:
3 Bedroom, 2 Bathroom, Sleeps 6
Location: Kihei, Hawaii, United States
Description: Keawakapu Retreat- " Alani...Sweet orange breeze" This recently remodeled home is nestled in an acre +, four home private estate from Old Hawaii-D... Learn More
Location: Kihei, Hawaii, United States
Description: Keawakapu Retreat- " Alani...Sweet orange breeze" This recently remodeled home is nestled in an acre +, four home private estate from Old Hawaii-D... Learn More
Rates
$325 - $525 night
$2275 - $3675 week
$325 - $525 night
$2275 - $3675 week
Condo:
1 Bedroom, 2 Bathroom, Sleeps 4
Location: Kihei, Hawaii, United States
Description: 601 is a 1 bedroom, 2 bath top floor condo with central A / C, light and bright tropical décor and a picture window facing the ocean. Electronics g... Learn More
Location: Kihei, Hawaii, United States
Description: 601 is a 1 bedroom, 2 bath top floor condo with central A / C, light and bright tropical décor and a picture window facing the ocean. Electronics g... Learn More
Rates
$125 - $175 night
$875 - $1225 week
$125 - $175 night
$875 - $1225 week
Condo:
3 Bedroom, 3 Bathroom, Sleeps 6
Location: Wailea, Hawaii, United States
Description: Wailea Elua Village #1305 boasts 3 bedrooms (king bed in the master and 2 twins in each of the guest bedrooms) and a prime oceanfront ground floor ... Learn More
Location: Wailea, Hawaii, United States
Description: Wailea Elua Village #1305 boasts 3 bedrooms (king bed in the master and 2 twins in each of the guest bedrooms) and a prime oceanfront ground floor ... Learn More
Rates
$995 - $1200 night
$6965 - $8400 week
$995 - $1200 night
$6965 - $8400 week
Condo:
1 Bedroom, 1 Bathroom, Sleeps 4
Location: Kihei, Hawaii, United States
Description: To see calendar click on "Availability" above main photo. If you're looking for the lowest price per sq. ft., this is not for you. If you're looki... Learn More
Location: Kihei, Hawaii, United States
Description: To see calendar click on "Availability" above main photo. If you're looking for the lowest price per sq. ft., this is not for you. If you're looki... Learn More
Rates
$95 - $155 night
$95 - $155 night
Bed and Breakfast:
4 Bedroom, 5 Bathroom, Sleeps 12
Location: Volcano, Hawaii, United States
Description: Please book on our website: VolcanoForestInn.Com or call our toll free number: 800-481-0450 VOLCANO FOREST INN - BIG ISLAND OF HAWAII - VISIT T... Learn More
Location: Volcano, Hawaii, United States
Description: Please book on our website: VolcanoForestInn.Com or call our toll free number: 800-481-0450 VOLCANO FOREST INN - BIG ISLAND OF HAWAII - VISIT T... Learn More
Rates
$149 - $169 night
$149 - $169 night
Condo:
1 Bedroom, 2 Bathroom, Sleeps 4
Location: Kihei, Hawaii, United States
Description: 405 is a 1 bedroom, 2 bath elegant yet casual condo that’s awaiting you. Enjoy your stay in this remodeled condo. Custom tile throughout, fully-sto... Learn More
Location: Kihei, Hawaii, United States
Description: 405 is a 1 bedroom, 2 bath elegant yet casual condo that’s awaiting you. Enjoy your stay in this remodeled condo. Custom tile throughout, fully-sto... Learn More
Rates
$125 - $175 night
$875 - $1225 week
$125 - $175 night
$875 - $1225 week
Special Offer May 1 - Dec 14 BOOK 14 NIGHTS BY DEC 31, 2012, GET A $75 RESTAURA ...
Condo:
1 Bedroom, 1 Bathroom, Sleeps 3
Location: Kihei, Hawaii, United States
Description: CHILLEDCOCONUT AT KIHEI BAY SURF is a 500 square feet top floor studio unit overlooking a tropical garden and mountain. We are inside the resort co... Learn More
Location: Kihei, Hawaii, United States
Description: CHILLEDCOCONUT AT KIHEI BAY SURF is a 500 square feet top floor studio unit overlooking a tropical garden and mountain. We are inside the resort co... Learn More
Rates
$45 - $159 night
$315 - $979 week
$45 - $159 night
$315 - $979 week
Condo:
3 Bedroom, 2 Bathroom, Sleeps 8
Location: Kihei, Hawaii, United States
Description: Royal Mauian is a unique six story oceanfront property located in South Kihei offering unobstructed views of the clear blue Pacific. The property a... Learn More
Location: Kihei, Hawaii, United States
Description: Royal Mauian is a unique six story oceanfront property located in South Kihei offering unobstructed views of the clear blue Pacific. The property a... Learn More
Rates
$375 - $437 night
$2468 - $3126 week
$375 - $437 night
$2468 - $3126 week
Condo:
2 Bedroom, 2 Bathroom, Sleeps
Location: Kailua-Kona, Hawaii, United States
Description: Beautiful oceanfront with 200 sq. ft. lanai, 180 degree views! The best view on the island. Master bedroom and living room both have floor to cei... Learn More
Location: Kailua-Kona, Hawaii, United States
Description: Beautiful oceanfront with 200 sq. ft. lanai, 180 degree views! The best view on the island. Master bedroom and living room both have floor to cei... Learn More
Rates
$165 - $250 night
$165 - $250 night
Condo:
2 Bedroom, 2 Bathroom, Sleeps 6
Location: Kihei, Hawaii, United States
Description: 302 is a spacious 2 bedroom, 2 bath renovated condo, perfect for a family getaway. Central A / C and double-pane glass keeps the condo cool and qui... Learn More
Location: Kihei, Hawaii, United States
Description: 302 is a spacious 2 bedroom, 2 bath renovated condo, perfect for a family getaway. Central A / C and double-pane glass keeps the condo cool and qui... Learn More
Rates
$160 - $215 night
$1120 - $1505 week
$160 - $215 night
$1120 - $1505 week
Home:
2 Bedroom, 3.5 Bathroom, Sleeps 6
Location: Kilauea, Hawaii, United States
Description: Estate property, 2 bedroom main home plus poolhouse, 3 Baths (Sleeps 6) Located on private 2.5 acre estate property, you’ll enjoy the peace and so... Learn More
Location: Kilauea, Hawaii, United States
Description: Estate property, 2 bedroom main home plus poolhouse, 3 Baths (Sleeps 6) Located on private 2.5 acre estate property, you’ll enjoy the peace and so... Learn More
Rates
$900 - $1200 night
$900 - $1200 night
Villa:
4 Bedroom, 3 Bathroom, Sleeps 10
Location: Wailea, Hawaii, United States
Description: Most popular Maui Condo Wailea Beach Villa L409 Rated Perfect on Trip Advisor. 4BR (3 Kings/1 Queen, or 2 Kings/ 2 Twins/1 Queen) 3 BA villa . Spec... Learn More
Location: Wailea, Hawaii, United States
Description: Most popular Maui Condo Wailea Beach Villa L409 Rated Perfect on Trip Advisor. 4BR (3 Kings/1 Queen, or 2 Kings/ 2 Twins/1 Queen) 3 BA villa . Spec... Learn More
Rates
$995 - $2350 night
$995 - $2350 night
Condo:
2 Bedroom, 2 Bathroom, Sleeps 6
Location: Kihei, Hawaii, United States
Description: The second floor location of this two bedroom two bath apartment cannot be beat! A spacious living area with kitchen and dining area that opens ... Learn More
Location: Kihei, Hawaii, United States
Description: The second floor location of this two bedroom two bath apartment cannot be beat! A spacious living area with kitchen and dining area that opens ... Learn More
Rates
$130 - $150 night
$910 - $1050 week
$130 - $150 night
$910 - $1050 week
Home:
4 Bedroom, 3 Bathroom, Sleeps 11
Location: Kailua, Hawaii, United States
Description: Kailuana is a unique private estate located on the windward side of Oahu, set in the residential community of Kailua. Kailuana Beachfront is one of... Learn More
Location: Kailua, Hawaii, United States
Description: Kailuana is a unique private estate located on the windward side of Oahu, set in the residential community of Kailua. Kailuana Beachfront is one of... Learn More
Rates
$550 - $1500 night
$3850 - $10500 week
$550 - $1500 night
$3850 - $10500 week
Condo:
3 Bedroom, 3 Bathroom, Sleeps 6
Location: Wailea, Hawaii, United States
Description: The “crown jewel” of Wailea- A gated beachfront location, an oceanfront adult pool with a Jacuzzi, a children’s pool with a Jacuzzi in a garden s... Learn More
Location: Wailea, Hawaii, United States
Description: The “crown jewel” of Wailea- A gated beachfront location, an oceanfront adult pool with a Jacuzzi, a children’s pool with a Jacuzzi in a garden s... Learn More
Rates
$795 - $1500 night
$5565 - $10500 week
$795 - $1500 night
$5565 - $10500 week
Condo:
2 Bedroom, 2 Bathroom, Sleeps 5
Location: Wailea, Hawaii, United States
Description: Wailea Elua Village #1204 is a beautiful two bedroom, two bath oceanfront condo that has been fully remodeled with top of the line appliances and t... Learn More
Location: Wailea, Hawaii, United States
Description: Wailea Elua Village #1204 is a beautiful two bedroom, two bath oceanfront condo that has been fully remodeled with top of the line appliances and t... Learn More
Rates
$594 - $795 night
$4158 - $5565 week
$594 - $795 night
$4158 - $5565 week
Home:
3 Bedroom, 3.5 Bathroom, Sleeps 7
Location: Poipu Beach, Hawaii, United States
Description: Secluded Tropical Oceanfront Hideaway - Very Private and Very Beautiful newly Decorated. AIR CONDITIONED with your own private pool. This beautifu... Learn More
Location: Poipu Beach, Hawaii, United States
Description: Secluded Tropical Oceanfront Hideaway - Very Private and Very Beautiful newly Decorated. AIR CONDITIONED with your own private pool. This beautifu... Learn More
Rates
$1000 - $1000 night
$4000 - $4000 week
$1000 - $1000 night
$4000 - $4000 week
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