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Vacation rentals with a pool in Waikoloa Village

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Waikoloa Village

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Condo in Waikoloa Village

4.78 out of 5 average rating, 116 reviews

Beautiful 1 BR, min from the beach in Waikoloa

Unit 137 at the Shores at Waikoloa is beautiful! It is also walking minutes from Anaeho’omalu Bay which boasts a stunningly scenic sand beach, especially at sunset. 'A' bay is also steps from the Marriott and the Lava Lava beach club. Our condo is equally close to the shops and restaurants at the Kings and Queen malls. Golf at the King's course is just across the way in Waikoloa or you can head up to the Village a few miles and play up there. This is a very walkable area and worth exploring.

Sep. 22 – 29

$422 CAD per night

Guest favourite

Guesthouse in Waikoloa Village

5.0 out of 5 average rating, 16 reviews

Ohana With Private Pool & Jacuzzi

Unwind & enjoy your private, luxurious & spacious ohana. Step outside to your own swimming pool & jacuzzi. Enjoy the view of Mauna Kea. Grill a farm-to-table style meal & enjoy dinner alfresco. The ohana is equipped as a suite with a sitting area, king size bed, 55” TV, kitchenette (microwave/freezer & fridge drawer/sink/ outdoor grill w/side burner), walk-in closet, washer & dryer, & bathroom. The pool lanai is enclosed within a rock wall, featuring loungers, sitting area, table, & grill.

Apr. 11 – 18

$640 CAD per night

Guest favourite

Condo in Waikoloa Village

4.95 out of 5 average rating, 108 reviews

Casa Chilin 2bd/2bth@Waikoloa Resort Walk To Beach

Aloha and thank you for considering our home for your visit to the Big Island of Hawaii. Our recently remodeled 2bd/2bath home is walking distance from Shopping (Kings/ Queens Shops), Dining, Entertainment, A’ Bay Beach, Historic Sites. The home is stocked with all your basic necessities. 1 covered parking spot included, steps from home. Great location for couples, groups, families with kids, everyone is welcome! Enjoy the sunset and trade wind breeze from the lanai. Washer and dryer in unit.

Oct. 11 – 18

$555 CAD per night

Guest favourite

Home in Waikoloa Village

4.93 out of 5 average rating, 188 reviews

1+ Acre private resort, 4 bed, 3 bath, cinema, spa

Rated in top 10 Airbnb's on the coast. Treat yourself to a vacation surrounded by unmatched landscaping, ocean view, 2000 sq/ft single level, fully stocked home with 3 bedroom, 3 bathrooms, Movie Theater; Office (or 4th bedroom), a/c in each room, waterfall, grotto, tiki torches, fruit trees, playground and so much more. Privacy of 1.2 acre flag lot, convenience of being close to groceries and best activities the island has to offer. 2 main bedrooms with king size, stern & foster mattresses.

Oct. 8 – 15

$1,049 CAD per night

Guest favourite

Home in Waikoloa Village

4.98 out of 5 average rating, 153 reviews

Ocean, Sunset, Mountain & Celestial Views

Enjoy ocean, mountain, sunset and star scape views from nearly every room in this family friendly, three bedroom and two bathroom house in Waikoloa Village, Hawaii. The house includes everything you'll need on your paradise escape including a fully equipped kitchen, beach gear (e.g. boogie boards, snorkel gear, coolers, beach towels and beach chairs) and Wi-Fi. We also provide bath towels, bed linens, soaps/shampoos, coffee, children's toys (age 3-7), a barbecue grill and outdoor seating.

Aug. 30 – Sep. 6

$572 CAD per night

Guest favourite

Villa in Waikoloa Beach

4.92 out of 5 average rating, 187 reviews

Luxury Beach Front Villa! Unbeatable value!

You will love this beach front property in the heart of Waikoloa. It is only a 2 minute walk to the pool and beach area from your lanai and 5 minutes to walk to the Kings Shoppes and the Queen's Market where you can find great shopping and fine dining. The beach in front of our property is very calm and sandy and the perfect place for a lazy day basking in the wonderful Hawaiian Sunshine while you take in all the beauty around you. Love the Sea Turtles but be careful to give them space!

Mar. 11 – 18

$1,195 CAD per night

Guest favourite

Condo in Waikoloa Village

4.94 out of 5 average rating, 139 reviews

Hale Le'ale'a has Hilton Pool Pass for 2024 stays

E Komo Mai-Welcome to Hawaii in the beautifully furnished Fairway Villas 2nd floor condo accessed by stairs or elevator. Hilton Pool Pass is now available for bookings after April 5th. Enjoy the air conditioning or leave windows open for Hawaiian breezes. Picture-perfect lanai facing north is always shaded. This 2 bdrm/2 bath condo sleeps 4 privately. There is a large living room, dining area, and eat in kitchen with all needed amenities. The unit is 1,172 sq ft. Designated parking place.

Oct. 13 – 20

$476 CAD per night

Guest favourite

Condo in Waikoloa Beach Resort

4.96 out of 5 average rating, 105 reviews

Enjoy lush tropical lifestyle in Waikoloa Resort

Enjoy your stay at this serene ground floor, remodeled in 2023, 1 bedroom 1 bath corner unit condominium in one of the best location of Waikoloa Beach Resort. * Lush tropical landscaping with ponds and waterfalls * Next to pool, tennis court, BBQ and fitness center * Walk to beach, shops, restaurants, entertainments and Grand Hilton * Free fast WiFi. Central A/C. Washer and dryer. * Spectrum Cable and Roku streaming TVs * Private Parking spot 50 yards from the front door

Apr. 3 – 10

$409 CAD per night

Guest favourite

Townhouse in Waimea

4.98 out of 5 average rating, 128 reviews

Luxurious 3 bedroom at The Fairways at Mauna Lani

Located amongst the best of the Kohala Coast's resorts, championship golf, and world class beaches. Booking our townhome will provide you with access to the exclusive private beach club located a few minutes drive away. The townhome and community feature all of the amenities you will need for your stay in Hawaii. There is wifi, cable tv, an outdoor propane grill, and incredibly comfortable living spaces. The Fairways is the perfect gateway to all The Big Island has to offer.

Jan. 25 – Feb. 1

$642 CAD per night

Guest favourite

Condo in Waikoloa Village

4.93 out of 5 average rating, 74 reviews

Renovated Condo with A/C, Pool & Spa

Kick back and relax in this stylish, clean space with everything you need to make your stay comfortable (including a community pool, spa and gym). The Fairway Terrace complex is located 20 minutes from the best beaches on the island! Close to shopping, restaurants, activities. This renovated corner unit condo has plenty of light and new furnishings. Enjoy the quiet lanai and golf course views after exploring what the island has to offer.

Nov. 11 – 18

$364 CAD per night

Guest favourite

Apartment in Kailua-Kona

4.96 out of 5 average rating, 227 reviews

KJ's Place, in the heart of the city.

We would like to welcome you to your "home away from home" on the beautiful Big Island! Relax in this stunning, remodeled Kona Ali'i condominium and experience clean, luxurious accomodations in the heart of the city. From here you are within walking distance of all Kona has to offer; from restaurants and shops, to swimming, the Ironman Village (in Oct) & the Christmas Parade (in Dec). We hope you enjoy your stay!

Jun. 27 – Jul. 4

$243 CAD per night

Guest favourite

Townhouse in Kamuela

4.95 out of 5 average rating, 304 reviews

Mauna Lani Fairways Resort Townhouse w/ BeachClub

Escape to our beautiful and tranquil paradise. The Fairways at Mauna Lani villa #206 is a luxury condominium in a gated community with resort style amenities, at the prestigious Mauna Lani Resort located along the sunny Kohala Coast of Hawaii's Big Island. Private Mauna Lani Beach Club Access - with Key Card and Parking !!! RATES ARE FULLY INCLUSIVE OF 18% HAWAII RENTAL TAXES!!!

Nov. 3 – 10

$699 CAD per night

Vacation rentals for every style

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Popular amenities for Waikoloa Village rentals with a pool

Free parking on premises

Air conditioning

House rentals with a pool

Guest favourite

Home in Waikoloa Village

4.87 out of 5 average rating, 125 reviews

Big Family Home, Pool, Views, Yard, Lanai, Clean!

Oct. 1 – 8

$1,026 CAD per night

Guest favourite

Home in Kailua-Kona

4.96 out of 5 average rating, 167 reviews

Halia Hale

Sep. 6 – 13

$765 CAD per night

Guest favourite

Home in Kailua-Kona

4.95 out of 5 average rating, 141 reviews

Private Pool - 180° Ocean View - Minutes to Beach

Nov. 9 – 16

$870 CAD per night

Guest favourite

Home in Captain Cook

4.98 out of 5 average rating, 164 reviews

Tiny House Hawaii

Jan. 30 – Feb. 6

$315 CAD per night

Home in Waimea

4.87 out of 5 average rating, 104 reviews

Mauna Lani Golfers and Vacationers Paradise

Jul. 23 – 30

$724 CAD per night

Guest favourite

Home in Kailua-Kona

4.9 out of 5 average rating, 117 reviews

Tropical Oasis Home with Pool and Steps to Beach

Sep. 30 – Oct. 7

$935 CAD per night

Guest favourite

Home in Kailua-Kona

4.94 out of 5 average rating, 196 reviews

Classic Kona 🤙🏻 \\ Epic Ocean View 🌊 \\ Pool 🏊

Sep. 10 – 17

$622 CAD per night

Guest favourite

Home in Waikoloa Village

4.98 out of 5 average rating, 60 reviews

Perfect Waikoloa Beach Resort home w/ Pool & Spa

Apr. 14 – 21

$1,502 CAD per night

Condo rentals with a pool

Guest favourite

Condo in Waikoloa Village

4.84 out of 5 average rating, 135 reviews

Waikoloa Condo on The Big Island HI

Mar. 29 – Apr. 5

$357 CAD per night

Condo in Waikoloa Village

4.93 out of 5 average rating, 14 reviews

Updated 1 bedroom in paradise!

Aug. 22 – 29

$302 CAD per night

Condo in Waikoloa Village

4.83 out of 5 average rating, 60 reviews

❤️Hale HallEAva❤️

Oct. 5 – 12

$278 CAD per night

Guest favourite

Condo in Waikoloa Village

4.93 out of 5 average rating, 15 reviews

Smart Adventure HQ Near Beaches

Oct. 25 – Nov. 1

$333 CAD per night

Guest favourite

Condo in Waikoloa Village

4.97 out of 5 average rating, 61 reviews

Waikoloa Fairway Villas C-2. 1st Floor "Quiet"!

Sep. 14 – 21

$480 CAD per night

Guest favourite

Condo in Waikoloa Village

4.98 out of 5 average rating, 50 reviews

Hale Honu -Turtle House Oceanview Luxury Penthouse

Jan. 23 – 30

$796 CAD per night

Guest favourite

Condo in Waikoloa Village

4.94 out of 5 average rating, 72 reviews

Seahorse Cottage, Waikoloa on Big Island of Hawaii

Dec. 20 – 27

$373 CAD per night

Guest favourite

Condo in Waikoloa Village

4.96 out of 5 average rating, 46 reviews

Honua Studio

Jun. 4 – 11

$290 CAD per night

Quick stats about vacation rentals with a pool in Waikoloa Village

Total rentals
1.3K properties
Rentals with dedicated workspaces
720 properties have a dedicated workspace
Pet-friendly rentals
10 properties allow pets
Family-friendly rentals
1.2K properties are a good fit for families
Total number of reviews
23K reviews
Nightly prices starting at
$137 CAD before taxes and fees

Destinations to explore