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Family-friendly holiday rentals in Winchester

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Winchester

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

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Top guest favourite
A dining area features a large wooden table surrounded by six velvet green chairs with gold accents. Tropical plants are placed on either side, and the table is set with white plates and glasses. Vibrant artwork hangs on the light-colored walls.
Home in Las Vegas
4.97 out of 5 average rating, 145 reviews

SPACIOUs 5*Villa/Strip/POOL/CHEF Kitchen/Office.

RARE on the market! This absolutely Stunning, fully remodeled licensed Artsy home with a POOL, BUSINESS CENTER, CHEF KITCHEN is in the heart of historic DOWNTOWN-just 5 min drive to Las Vegas Strip, 10 min to Convention Center and 3 min to Fremont Experience. Nestled in a peaceful neighborhood this exquisite retreat is ideal for guests seeking luxury, comfort, and fun all in one place. Thoughtfully designed and beautifully equipped, this home meets all your family, business, and leisure needs.

Top guest favourite
Home in Las Vegas
4.97 out of 5 average rating, 228 reviews

Splash & Giggle in LV, Pool, WiFi, 2 KG Bds, BBQ

The moment you open the door, you’ll feel right at home. Cozy and comfortable. You’ll notice all the extra touches provided for your enjoyment. It's 15 minutes to the Strip and Chinatown. Red Rock is 5.9 miles—fast WiFi. The pool is not heated but is warm, has a safety fence to protect the kids, and helps you relax while on vacation. The beds in my home are amazing! Large comfy leather couch. We are near a large park and Close to the Casino, restaurants & stores, & freeways. There isn’t an HOA.

Top guest favourite
A spacious living area is presented, featuring a large sectional sofa adorned with decorative pillows. A round coffee table sits at the center, complemented by a light rug. In the background, a modern kitchen with an island and stylish dining area is visible, illuminated by natural light.
Home in Las Vegas
4.93 out of 5 average rating, 180 reviews

Family Retreat Private Pool Close to Strip/Airport

Beautiful and spacious 4 bedroom/3 bath with 5 beds/bean bag turns into a double mattress . Home located less than 3 mil from the Strip/Airport. Master Suite with private bathroom. 86in TV in family room . Fully Stock kitchen for any occasions. Dedicated workplace in all rooms. Up to 1 GB of fast internet for all your streaming, working, video call for your group. 2 arcade games and a poker table. Private in ground pool. Outdoor BBQ also Located on Private cul-de-sac. Family and pet friendly.

Top guest favourite
A warm living area features a spacious seating arrangement with two distinct seating options. Natural light filters through large windows, while a prominent artwork adds character to the wall. Wood flooring complements the overall cozy atmosphere, inviting relaxation.
Home in Las Vegas
4.95 out of 5 average rating, 257 reviews

Historic Bungalow Arts District Summer Fireworks!

This is the coziest bungalow in the heart of the Historic John S Park neighborhood. Backyard has amazing views of the hotel’s summer fireworks displays (June/July)! - Very Pet friendly! - 77 walk score, 64 transit score, 55 bike score. - 5 min drive or short walk to the Las Vegas Strip, 4 min drive to Fremont Street/Arts District/Main Street, 15 min from the airport. - Mission/Arts and Craft furniture true to period. - Fabulous original art from local artists. - Extremely safe neighborhood.

Top guest favourite
A spacious room is presented with light wood flooring and neutral colored walls. A queen mattress is dressed in a light coverlet, while a television is mounted on the wall across from a desk and chair. A dresser with multiple drawers offers additional storage.
Guest house in Las Vegas
4.92 out of 5 average rating, 193 reviews

Luxury Guest Suite

Luxury Guest House with full kitchen and home amenities, comes with a queen luxury mattress bed with a Futon Sofa bed that can accommodate one more adult or 2 children. The place is a guest house with it’s own private entrance on the side of the house can’t missed the pavers way leading you to the entrance gate. 5 mins from the airport and 5-10 mins to the strip it is a great location. We’ve got cameras, for your protection and ours we have cameras filming only the front of the property.

Guest favourite
The living area features a blue sectional sofa adjacent to a small white coffee table. A large television is placed on a grey media console. Two framed botanical prints adorn the pink walls, and light enters through a partially closed door with a curtain. Potted plants add greenery.
Guest house in Las Vegas
4.85 out of 5 average rating, 208 reviews

My pretty little house

Enjoy the simplicity of this quiet, centrally located accommodation, 10 minutes from the Strip and casinos, 10 minutes from the airport and best of all in a family-friendly, clean and quiet neighborhood. In just the blink of an eye, you'll be at the city's most exciting attractions! It's an attached home to the main residence, offering privacy and complete independence. It features a master bedroom with a double bed, a sofa bed in the living room, a separate bathroom, and a kitchen.

Top guest favourite
A spacious living area is depicted featuring a sectional sofa, a circular coffee table, and a dining set with four chairs. Natural light fills the room through large windows, and a staircase leads to the upper level. A neutral color palette enhances the calming ambiance.
Home in Las Vegas
4.93 out of 5 average rating, 151 reviews

Stoney Getaway

Welcome to our inviting Airbnb escape, a true retreat nestled just 16 minutes away from the dazzling Las Vegas Strip. With 2 specious bedrooms, a refreshing pool and modern amenities, our home offers the perfect blend of comfort, style and convenience. Our Airbnb is strategically located, providing easy access to a variety of nearby facilities and services. In close proximity you can find a well equipped gym, Whole Foods Market and for a quick and tasty bite, the famous In-N-Out.

Guest favourite
An aerial view captures the Trump hotel illuminated against the Las Vegas skyline at dusk. The vibrant city lights twinkle below, showcasing iconic landmarks along the Strip. Mountains can be seen in the distance, enhancing the panoramic cityscape.
Flat in Las Vegas
4.86 out of 5 average rating, 686 reviews

Trump Tower High Floor with Strip & Sphere View

This Deluxe Suite offers the best view at Trump Las Vegas. The unit is 600 sqft on 47th floor with south strip view ! The final price includes: tax & all the fees & Free Valet Parking , EXCLUDING the Transient Occupancy Fee (Note 1. section of :"other things to note" below). We信:Davidqinghe All reservation requires 48 hour in advance. The guests are responsible for any cancellation penalty (up to 50 % per airbnb policy) Min. age 21+ (for check in person only_hotel policy)

Guest favourite
An entrance area is depicted, featuring two black folding chairs with botanical-themed cushions placed around a small table. A decorative potted plant rests on the table, and a welcome mat is positioned in front of the door. Nearby, a wall-mounted air conditioning unit is visible.
Flat in Las Vegas
4.96 out of 5 average rating, 241 reviews

Las Vegas Luxury Suite

This lovely property offers a great and fabulous stay for guests. The room features a very comfortable and elegant queen-size bed. It has a fully-equipped kitchen and a private bathroom for a refreshing shower. Stay connected with WiFi and TV with Netflix, YouTube, enjoy these amenities (request a list). Whether you're exploring the vibrant city or trying your luck at the casinos, our studio is the perfect base for your Las Vegas adventure.

Top guest favourite
Home in Las Vegas
4.92 out of 5 average rating, 104 reviews

Cozy 2-bedroom single story home

Relax in a beautifully decorated home with lots of amenities. Spacious kitchen with wine bar. Cozy backyard patio with ambience and mountain view (great for relaxing and barbequing). Conveniently located 15 minutes from the Las Vegas strip, 15 minutes from downtown Summerlin and Red Rock Canyon. Just minutes away from Lone Mountain for hiking and impeccable views of the city. Owner Operated and fully licensed.

Top guest favourite
Casa particular in Las Vegas
4.95 out of 5 average rating, 163 reviews

Delightful living area by Strip

This special place is close to everything, making it easy to plan your visit. Very close to Las Vegas attractions like the Strip, Downtown, Shopping Centers, etc.. Very comfortable living space making your stay here a delight and very stress free. Also offering enclosed gate parking for guests, offering safe vehicle parking! I am open to any questions/concerns you may have! Just let me know, very easygoing.

Guest favourite
The backyard features a curvilinear pool, illuminated in soothing blue light. Tall palm trees create a tropical ambience, while the surrounding area is lined with soft garden lighting. A covered seating area is visible in the background, providing an inviting space for relaxation.
Home in Las Vegas
4.9 out of 5 average rating, 102 reviews

Beautiful Modern Home with Pool & Spa !:24)

BUSINESS LICENSE NUMBER: G64-03484 Our spacious 4BR home is only minutes from the world famous Las Vegas Strip; perfect for an amazing getaway with friends and family! Spa heating is included at no extra cost! Pool heating is ONLY $75 per day (must be paid for the entirety of your stay). Enjoy and relax in the private backyard that comes with a pool and spa, surrounded by tall beautiful palm trees!

Popular amenities for Winchester family-friendly rentals

When is the best time to visit Winchester?

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Avg. price$267 SGD$252 SGD$275 SGD$259 SGD$306 SGD$252 SGD$245 SGD$245 SGD$253 SGD$268 SGD$264 SGD$268 SGD
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Quick stats about holiday rentals that are family-friendly in Winchester

  • Total holiday rentals

    Explore 720 holiday rentals in Winchester

  • Nightly prices starting at

    Winchester holiday rentals start at $38 SGD per night before taxes and fees

  • Verified guest reviews

    Over 26,180 verified reviews to help you choose

  • Pet-friendly holiday rentals

    Find 270 rentals that welcome pets

  • Holiday rentals with a pool

    530 properties feature pools

  • Rentals with dedicated workspaces

    460 properties have a dedicated workspace

  • Wifi availability

    720 of Winchester holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Winchester rentals

  • 4.8 Average rating

    Winchester stays are highly rated by guests – averaging 4.8 out of 5!

  • Nearby attractions

    Winchester’s top spots include AREA15, The STRAT Hotel and Casino & SkyPod

Destinations to explore