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Family-friendly holiday rentals in Hawaii

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Top-rated family-friendly rentals in Hawaii

Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.

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Apartment

4.83 out of 5 average rating, 143 reviews

Palms At Wailea #608-2 BR/2 BA.- Dec. Special

Beautiful Palms At Wailea Condo, located in the heart of Wailea, surrounded by $mil.homes. 5* location. Vinyl wood flooring & Split Air-Cond. system in hallway & in master-B/R. Fans through-out. Immaculately clean & comfortable. Walking distance to shops, hotels, restaurants, beaches.1200 sq. ft., 2BR/2Ba, wide open floor plan ,2nd. fl.unit. Low rise complex. Very private. Large lanai . Barbecue grills located near entryway of complex. Views from the Club House & Pool.The best place to stay!

Guest favourite

Home

4.94 out of 5 average rating, 104 reviews

Tropical Private Oasis, Heated Pool & OceanView!

3 bedroom/2.5 bath, Sleeps 8 with Private Solar Heated Pool with Waterfall, Lanai, Gazebo with Ocean View, Tropical Yard. 5 min to downtown Kona along the water. This "model home" sits in a gated community of Kahakai with breathtaking views. It has all upgrades throughout the house for ultimate luxury. A pathway on this 1/2 acre plus property leads to an elevated private gazebo for that amazing romantic evening dinner or relaxing with your special one while looking at an amazing ocean view.

Apartment

4.83 out of 5 average rating, 157 reviews

Awesome Maui home away from home. Covid Cleaned.

A/C throughout. Work desk with dependable wi-fi. 2 Cable TVs . Grass area off lanai. Walk to the beach, stores, restaurants, the park or bus stop. Full kitchen, W/D, 2 queen beds and 1 queen sofabed, 4 beach chairs, 4 beach towels, a beach umbrella and travel cooler, Pak-n-Play, Booster Seat, 2 pking spaces. This condo is comfortable and well-eqipped for a wonderful stay and vacation on Maui. The pool, jacuzzi and BBQ area will be closed for renovation from July8- early October.

Guest favourite

Cottage

4.92 out of 5 average rating, 212 reviews

Ualani Retreat. Private Ocean View Cottage.

GREAT SPECIALS THRU October Private Detached stand alone cottage home on 3 acre retreat. Beautiful ocean and mountain views. Lush Haven surrounded by fruit trees and bamboo groves. Nicely equipped kitchen. Laundry room. Cable TV. Wi-Fi. Delightful Island Home. Very Comfortable. Hot Tub. Close to enjoy some of Maui's best attractions - Haleakala Volcano, Road to Hana, Waterfalls & Baldwin Beach. Locally Owned & Occupied B&B PERMIT : BBPH 2012/0002 SUP2 2012/0001

Apartment

4.85 out of 5 average rating, 102 reviews

Spacious Condo sleeps 4-6, near golf course, ocean

Well-appointed beautiful, clean, updated 800 SF condo located in Kona, HI on The Big Island. A fully equipped unit is nestled in a peaceful, tropical landscape, with back lanai facing the golf course. 1 bedroom with a king-size bed, den with queen size bed and converts to 2nd bedroom, a sleeper sofa for two and two baths. Airbed also available in the unit. Near all amenities, beaches, approximately 30 minutes from Kona airport. IRONMAN-approx. 12 minutes from town center. Sleeps 5-6

Guest favourite

Home

4.88 out of 5 average rating, 133 reviews

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

Beautiful view home 4 bedrooms, Heated Pool! Big private yard, gourmet kitchen, 2 car garage, BBQ. Each bedroom leads out to the lanai(s) through French doors. Comfortably sleeps 10! Less than 10 minutes to awesome beaches, shopping, and restaurants. We now offer air-conditioning for a nominal fee. Please let us know if you would like to add this option to your reservation, the cost is $20/night.

Guest favourite

Apartment

4.86 out of 5 average rating, 154 reviews

Turtle Bay Condo, 2 Bedroom, sleeps 6

This sweet retreat is located on the beautifully manicured grounds of the Turtle Bay Resort in a gated condo community nestled on two world class championship golf courses. The beach is a just short walk from your front door. This upstairs, two level condo features vaulted ceilings, open living area, fairway golf course views, and all the rest and relaxation you could ask for!

Guest favourite

Apartment

4.82 out of 5 average rating, 148 reviews

2 Bdrm/2 Bath Condo Steps to Kamaole III Beach

Close to parks, beach, restaurants, great views, art and culture. We have a fully stocked kitchen, entertainment center and lanai. We host couples, solo adventurers, business travelers, and families. Our high ceilings are open air, the rooms and bedrooms are not completely private (walls do not meet the ceiling). Condo is clean, we have beach towels, beach chairs, & WiFi!

Guest favourite

Home

4.9 out of 5 average rating, 143 reviews

Big Island Home Away From Home

Home is in the Heart of Hilo, very conveniently located. 10 Minutes from the Airport, less than 5 miles from shopping mall, groceries, Hilo Farmers Market and beautiful beaches. Our home provides a clean and comfortable living space. Downstairs has laundry facilities and second bathroom. Two car covered carport for your jeep and the convertible.

Guest favourite

Apartment

4.87 out of 5 average rating, 261 reviews

Newly remodeled and close to beaches, shopping!

Newly remodeled condominium with all new furniture and appliances. Our condo is located within walking distance to restaurants and shopping. We are located directly across the street from Charlie Young Beach. Swimming pool and tennis courts, quiet location, nice views and plenty of parking. TA-143-927-7055-01

Bungalow

4.77 out of 5 average rating, 522 reviews

Hawkins Vacation Rental--time to get away

My vacation rental is a spacious, beautifully-furnished cottage, next to my home, on 1/2 acre in a small, upscale community just two miles north of the historic whaling town of Hilo. Honolii Beach, the popular eastside surf spot, is a five-minute walk down a one-lane road. Taxes are paid upon arrival.

Apartment

4.79 out of 5 average rating, 127 reviews

Ocean View 1 BR sleeps 4, Steps to the Beach!

My place is close to The BEACH, great views, restaurants and dining, art and culture. You’ll love my place because of the ambiance, the outdoors space, the neighborhood, and the comfy bed. My place is good for couples, solo adventurers, business travelers, and families (with kids).

Holiday rentals for every style

Get the amount of space that is right for you

Bungalows

Intimate homes, inviting architecture

Villas

Luxurious estates for the ultimate escape

Flats

Convenient locations with everyday essentials

Popular amenities for Hawaii family-friendly rentals

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

Guest favourite

Home

4.93 out of 5 average rating, 520 reviews

Secluded Rainforest Getaway! Hot Tub! Volcano!

Guest favourite

Home

4.87 out of 5 average rating, 110 reviews

Beautiful Island Style Home with *A/C* and Hot Tub

Townhouse

4.82 out of 5 average rating, 130 reviews

Kona Hawaiian Shangri-La in a 3bd / 3 ba

Guest favourite

Home

4.88 out of 5 average rating, 427 reviews

Hale Ma'ukele in beautiful Volcano

Guest favourite

Home

4.92 out of 5 average rating, 102 reviews

Sunset Waterfall House In Kauai

Guest favourite

Flat

4.91 out of 5 average rating, 178 reviews

Relaxing Tropical Retreat close to Kailua Kona

Guest favourite

Home

4.92 out of 5 average rating, 126 reviews

Spectacular view and natural beauty

Guest favourite

Flat

4.91 out of 5 average rating, 1,020 reviews

Kula Treat - Upcountry Maui with Hot Tub!

Family- and pet-friendly home rentals

Guest favourite

Flat

4.91 out of 5 average rating, 166 reviews

The Big house -1500 sq/ft - 30+ days!

Guest favourite

Guest suite

4.92 out of 5 average rating, 283 reviews

2 Room Private Treetop Suite

Guest suite

4.91 out of 5 average rating, 454 reviews

☀ Private Garden w/ Ocean Views → Green Sands ☀

Guest favourite

Home

4.88 out of 5 average rating, 189 reviews

Tropical Tree Guest House near Pahoa, Hawaii

Guest favourite

Apartment

4.94 out of 5 average rating, 139 reviews

Oceanfront, Modern, Accessible Kona: Close to Town

Home

4.75 out of 5 average rating, 102 reviews

Enchanted Volcano Forest Escape 3BDRM Rental House

Guest favourite

Home

4.96 out of 5 average rating, 157 reviews

Milolii Whale House With Ocean Views and Pool!

Guest favourite

Home

4.91 out of 5 average rating, 170 reviews

Mini Plantation with a View

Family-friendly home rentals with a pool

Guest favourite

Home

4.95 out of 5 average rating, 152 reviews

Private Pool - 180° Ocean View - Minutes to Beach

Guest favourite

Guest suite

4.96 out of 5 average rating, 240 reviews

Family-Friendly Retreat Guest Suite-Pool!

Guest favourite

Home

4.96 out of 5 average rating, 411 reviews

Stunning ocean view, heated pool at home by Wailea

Guest favourite

Apartment

4.96 out of 5 average rating, 111 reviews

Luxurious Condo - Beautiful Pool View

Flat

4.75 out of 5 average rating, 59 reviews

Koa Resort 1F 4 Bedrm,3ba 1800sf townhome

Guest favourite

Cabin

4.96 out of 5 average rating, 352 reviews

Country Cottage

Guest favourite

Flat

4.95 out of 5 average rating, 355 reviews

Tropical Condomium with Pool and Verdant Garden

Townhouse

4.83 out of 5 average rating, 115 reviews

Beautiful Tropical Getaway - Pool - Grill & More

Destinations to explore