Holiday rentals near Dovetail

We found 2,687 holiday rentals — enter your dates for availability

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November 2025

December 2025

Find the perfect holiday rental that's near Dovetail. Holiday homes provide the amenities that you need and want for you and your friends, family or even pets, such as parking and a pool. At the end of the day, you'll be able to choose a property to rent for everyone's needs, including a place that's non-smoking or offers accessibility.

Holiday rentals with weekly discounts - Dovetail

Showing deals for:6 Feb - 13 Feb

Exceptional

(128 reviews)

Maka Nui Estate Luxury OceanView Retreat Above Kealakekua Bay, Family friendly

Captain Cook, HI

7% off

for 7 nights, 1 home

AU$2,653 per night

includes taxes & fees

Just a short walk down to Kailua Pier, and steps away from Alii Drive.

Exceptional

(9 reviews)

Kona Rose's Hideaway in Kona Plaza #318 at the center of Kailua-Kona Town

Kailua-Kona, HI

9% off

for 7 nights, 1 room

AU$556 per night

includes taxes & fees

Drive up your private driveway and park right next to the home.

Exceptional

(47 reviews)

Gorgeous Ocean View, Comfortable Cool Elevation, Close to Everything!

Kailua-Kona, HI

7% off

for 7 nights, 1 home

AU$1,118 per night

includes taxes & fees

Exceptional

(12 reviews)

Beautiful Kona Hawaiian Resort - 2BR/2BA Deluxe Unit

Kailua-Kona, HI

8% off

for 7 nights, 1 room

AU$923 per night

includes taxes & fees

HISTORICAL DISTRICT OF KAHALU'U. PLACE. SURF, CANOEING, AGRICULTURAL OF CHIEFS.!

Exceptional

(97 reviews)

FABULOUS BEACH HOUSE, OCEAN FRONT VIEW, BEST LOCATION, WALK TO BEACH, RELAXING!.

Kailua-Kona, HI

6% off

for 7 nights, 1 home

AU$897 per night

includes taxes & fees

Exceptional

(6 reviews)

4 bedroom/ 3 bath luxury home with A/C, steps to community pool, oceanview

Kailua-Kona, HI

7% off

for 7 nights, 1 home

AU$2,115 per night

includes taxes & fees

Exceptional

(5 reviews)

NEW LISTING Kailua-Kona 3-bedroom, 2-bath single-family home Ocean & Sunset View

Kailua-Kona, HI

7% off

for 7 nights, 1 home

AU$1,207 per night

includes taxes & fees

Exceptional

(44 reviews)

Ocean Views/Mountain Views!!! - Best Price - 2 Bedroom/Bath - Beach across road!

Kailua-Kona, HI

8% off

for 7 nights, 1 apartment

AU$711 per night

includes taxes & fees

Kailua-Kona Vacation Rental | 1BR | 1BA | 500 Sq Ft | Stairs Required

Exceptional

(70 reviews)

1 Mile to Magic Sands Beach: Kailua-Kona Cottage

Kailua-Kona, HI

6% off

for 7 nights, 1 cottage

AU$326 per night

includes taxes & fees

Exceptional

(106 reviews)

Immaculate; Air Cond; Ocean/Garden views; WiFi N

Kailua-Kona, HI

7% off

for 7 nights, 1 apartment

AU$401 per night

includes taxes & fees

Exceptional

(30 reviews)

Charming Mountain Hideaway — Cozy Escape Near the Coast

Kailua-Kona, HI

7% off

for 7 nights, 1 home

AU$542 per night

includes taxes & fees

Exceptional

(19 reviews)

Manta Ray Manor - Oceanfront Gated Community, short walk to beach and town.

Kailua-Kona, HI

8% off

for 7 nights, 1 home

AU$2,800 per night

includes taxes & fees

Wonderful

(77 reviews)

Located minutes away from Historic Holualoa village and Kailua-Kona and beaches.

Honalo, HI

7% off

for 7 nights, 1 home

AU$238 per night

includes taxes & fees

Exceptional

(90 reviews)

Gated Keauhou Residences w/Ocean Views & Pool!

Kailua-Kona, HI

10% off

for 7 nights, 1 home

AU$2,374 per night

includes taxes & fees

Primary Suite with Ocean Views off your private lanai

Exceptional

(38 reviews)

New! 🌺 Kahaluu Bay Village 201 🐠 Close to Snorkeling, Swimming & Surfing Plus Pool 🐬

Kailua-Kona, HI

5% off

for 7 nights, 1 apartment

AU$772 per night

includes taxes & fees

Oceanfront views from your beautiful oceanfront lanai!

Exceptional

(86 reviews)

Amazing 🏄‍♀️ Oceanfront Penthouse 🐬 Newly Renovated! - Banyan Tree 403C 🌅

Kailua-Kona, HI

5% off

for 7 nights, 1 apartment

AU$1,089 per night

includes taxes & fees

Wonderful view from your top floor lanai

Exceptional

(30 reviews)

Remodeled 🏝 Amazing Ocean Views over Lush Golf Course! 🐠 Country Club Villas 320 🩴

Kailua-Kona, HI

5% off

for 7 nights, 1 apartment

AU$799 per night

includes taxes & fees

The lanai overlooks the pool area. There is also a hot tub, chairs and BBQ.

Exceptional

(6 reviews)

Kona Islander Inn - #316 - Located in beachfront town of Kailua Kona Hawaii.

Kailua-Kona, HI

7% off

for 7 nights, 1 apartment

AU$441 per night

includes taxes & fees

Exceptional

(9 reviews)

Charming Condo Hotel in lovely Beach front Kailua-Kona with AC, WiFi

Kailua-Kona, HI

7% off

for 7 nights, 1 apartment

AU$441 per night

includes taxes & fees

Wonderful

(6 reviews)

Luxury Beachfront Gated retreat in-town SPA/AC/BBQ accessible to the public pool

Kailua-Kona, HI

7% off

for 7 nights, 1 home

AU$2,495 per night

includes taxes & fees

Find spaces that suit your style

House

Condo/Apartment

Find the best place to stay - Dovetail

Showing deals for: 2 Feb - 5 Feb

Aston Kona by the Sea

Sleeps 4 · 1 bedroom

for 3 nights, 1 room

AU$677 per night

includes taxes & fees

★★ Beautiful 5-star ★ Ocean View near beaches, quiet, private pool/spa/AC ★★

Sleeps 18 · 5 bedrooms · 4+ bathrooms

for 3 nights, 1 home

AU$2,163 per night

includes taxes & fees

Premier Host

Apartment in town-walking distance to everything

Sleeps 4 · 1 bedroom · 1 bathroom

for 3 nights, 1 apartment

AU$405 per night

includes taxes & fees

Top rated rentals - Dovetail

Premier Host

Great stay

Great location and property, we will be back! Thanks for having us :)

Marion M.

Stayed Oct 2024

Premier Host

Waaaaaay Above and Beyond!

Gale and her property a absolutely beautiful. Home made banana bread and anything else you could want in a rental are all provided with Gale’s special touch. Simply cannot rate this beautiful boutique property highly enough. 100% recommend to anyway wanting a fantastic hideaway home!

Tanya J.

Stayed Dec 2022

modern oceanfront house with open-air living and sunset 360 per year.

Premier Host

Amazing

What can I say, what a beautiful house and beautiful location. We thoroughly enjoyed our stay but unfortunately we only stayed for 5 days. We will defiantly be returning to Hawaii. We shared this house with my wife's brother and his family which made 8 of us. Even though there is only 3 bedrooms there is plenty of room for 8. We were amazed to find the amount of extras left in the house which made our stay even more comfortable. On another note, i would personally like to thank Cliff for helping my wife out after we had left the property. Once we had arrived in Honolulu we realized that my wife's medication was left behind in the fridge. I contact Cliff and he arrange for the postage of the meds to our hotel in Honolulu. THANK YOU!!!! Once again thank you and we can't wait to return. Happy Travelers Coupe's & Allen's

Robert C.

Stayed June 2016

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More quality time
From booking to staying, the whole process is simple and enjoyable
All the privacy of home
Enjoy full kitchens, laundry, pools, gardens and more
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Holiday rentals near Dovetail

Holiday rentals with weekly discounts - Dovetail

Image gallery for Maka Nui Estate Luxury OceanView Retreat Above Kealakekua Bay, Family friendly

Maka Nui Estate Luxury OceanView Retreat Above Kealakekua Bay, Family friendly

Find spaces that suit your style

Find the best place to stay - Dovetail

Aston Kona by the Sea

Top rated rentals - Dovetail

Great stay

Peace of mind

More quality time

All the privacy of home

More for less

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