Some info has been automatically translated. Show original language

Family-friendly holiday rentals in Winchester

Find and book unique family-friendly homes on Airbnb

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

Top-rated family-friendly rentals in Winchester

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

%{current} / %{total}1 / 1
Top guest favourite
A stunning night view highlights the vibrant Las Vegas Strip, showcasing illuminated hotels and attractions. The image captures the glow of city lights through a large window, providing a glimpse of the bustling atmosphere below, with iconic landmarks prominently displayed.
Apartment in Las Vegas
4.96 out of 5 average rating, 219 reviews

TRUMP TOWER (51st Floor) - View of Las Vegas Strip

Luxury at an affordable price! Amazing views of the Las Vegas Strip, The Sphere, city and mountains. The studio unit comes with a King-sized bed and a sofa that folds out to a queen. The kitchenette has appliances by Wolf, Bosch and Sub-Zero. Glassware, silverware and plates are not included. The bathroom is done with twin sinks, Italian marble. Large shower and jacuzzi tub. Enjoy WiFi and access to the pool and fitness center. Walking distance to the Strip and adjacent to the Fashion Show Mall.

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
4.96 out of 5 average rating, 141 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
4.98 out of 5 average rating, 125 reviews

Casa Stella | Chic Villa 5 Min Airport • Sleeps 10

Welcome to a design-forward private villa minutes from the Strip and five minutes from the airport—ideal for effortless arrivals and short luxury stays. Set on a rare quarter-acre lot, this 2,400-sq-ft contemporary retreat offers curated interiors, open living spaces, and a resort-style backyard rarely found this close to the action. Enjoy privacy, space, and easy access to dining, nightlife, and major venues. Effortless, private, and impeccably located — this offers the best of both worlds.

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
4.94 out of 5 average rating, 254 reviews

Unique Historic Bungalow Downtown Arts District

This is the coziest, unaltered bungalow in the center of the Historic John S Park neighborhood. - Very Pet friendly! - 77 walk score, 64 transit score, 55 bike score - close to every amenity! - 5 min drive to the Las Vegas Strip, 4 min drive to Fremont Street/Arts District/Main Street, 15 min from the airport. - Easy Walk to Fremont Street, Main Street/Arts District - 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, 189 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.

Top guest favourite
Home in Las Vegas
4.97 out of 5 average rating, 225 reviews

Splash and Giggle in LV, POOL, WiFi, 2KG BDs, Dogs

The moment you open the door and walk in, 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. Play area for the Kiddos. The pool has a safety fence to protect the kids and help you relax while on vacation. The beds in my home are amazing! Also have a crib and a high chair. Large leather couch. Close to the Casino, restaurants & stores, & freeways.

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
4.92 out of 5 average rating, 145 reviews

Stoney

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, 681 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)

Top guest favourite
A panoramic view of Las Vegas at night showcases a vibrant cityscape illuminated by colorful lights. The sparkling skyline highlights iconic landmarks, while a spacious balcony railing is visible in the foreground, adding a sense of openness to the scene.
Apartment in Las Vegas
4.97 out of 5 average rating, 152 reviews

Sky-High Condo With Strip View

Experience the epitome of elegance in this 39th-floor condo, featuring a balcony with breathtaking views of the Las Vegas Strip. This sophisticated retreat offers a pristine, comfortable living space with modern furnishings. The spacious balcony invites you to unwind and soak in the vibrant city lights. Perfect for those seeking a luxurious lifestyle, this condo combines comfort and style, creating an unparalleled living experience in the heart of Las Vegas.

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, 234 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
Casa particular in Las Vegas
4.95 out of 5 average rating, 149 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
Flat in Las Vegas
4.86 out of 5 average rating, 236 reviews

Penthouse Suite @PalmsPlace Balcony-Jacuzzi

Perched on the top floor @ Palms Place Hotel, this stylish Penthouse Suite is 1300 sqft, w/ one bedroom, spacious kitchen & dining area. Large private balcony with jacuzzi and uninterrupted 180-degree views for that exclusive Vegas experience. Featuring a large, spa-like bathroom with dual sinks & Roman jacuzzi bathtub. Access to Palms Place amenities + Palms casino pools.

Popular amenities for Winchester family-friendly rentals

When is the best time to visit Winchester?

MonthJanFebMarAprMayJunJulAugSeptOctNovDec
Avg. price$266 SGD$251 SGD$274 SGD$258 SGD$306 SGD$251 SGD$244 SGD$244 SGD$252 SGD$267 SGD$264 SGD$267 SGD
Avg. temp10°C12°C16°C20°C25°C31°C34°C33°C29°C21°C14°C9°C

Destinations to explore