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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 $39 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.

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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 Strip
4.96 out of 5 average rating, 222 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 Soaking 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 nighttime view showcases the vibrantly lit Las Vegas Strip, featuring the iconic Bellagio Fountain in the foreground. Various hotel and casino facades are illuminated in a spectrum of colors, with the High Roller Ferris wheel visible in the distance against a dark sky.
Flat in Las Vegas Strip
4.96 out of 5 average rating, 268 reviews

Loftiest VDARA Penthouse StripSphereBellagio views

Stylish City Centre Vegas Strip-Bellagio Fountain-located 941 SQFT 1BDR Vdara Hotel & Spa Suite. One of Vdara's TOP suites All from the 55th floor, open the black-out curtains to reveal unparalleled Vegas strip & Bellagio Fountain Views Large living area, 1 pull-out Queen Sofa Bed, dedicated workspace, separate bedroom with PillowTop King size bed & more views. Double vanity bathroom, spa-like bathtub, large sit-in shower Kitchenette, an additional 1/2 bath. NON-SMOKING penalties maybe charged

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
A serene outdoor space is featured with a lagoon-style pool and a relaxing jacuzzi, complemented by a waterfall. Sun loungers are positioned nearby for comfort, while tall green trees and potted plants provide natural privacy around the area.
Home in Las Vegas
4.99 out of 5 average rating, 135 reviews

Brand New Listing Modern Hacienda Home Heated Pool

Mi Casa es su casa =) Charming Brand new freshly renovated modern luxury hacienda home for you to have fun with the whole family. Best neighborhood in Vegas doesn't get any better than this. This stylish single family home is close to golf, tennis, shopping, hiking, and of course the famous Las Vegas strip. Enjoy some relaxed resort style vacation vibes with thoughtful touches to ensure a comfortable and memorable stay with family and friends. As always a VIP guest service experience with us.

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, 258 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 private backyard features a clear blue pool accompanied by a spa, bordered by a spacious patio. Tall palm trees and a brick wall provide a sense of privacy. A covered area with curtains offers shade, and a dining table is positioned nearby.
Home in Las Vegas
4.89 out of 5 average rating, 571 reviews

3BR Vegas Oasis- Private Pool - BBQ -Mins to Strip

CLOSE TO EVERYTHING in Vegas! 5 minute drive to Fremont St., Las Vegas Blvd, Arts District, World Market Center, Smith Center, Children's Museum & the Premium Outlets. 10 minutes to the Convention Center & the Strip. 20 minutes to Red Rock Canyon, and the airport. You’ll LOVE the private cozy back yard with pool, grill and covered patio. *Pool and spa are not heated* Perfect for couples, solo adventurers, business travelers, families with kids, and groups. Business License #G64-O888O.

Top guest favourite
Two inflatable dolphin pool floats in soft pink and blue are positioned in a glowing pool at night. The surrounding area is enhanced by lush plants and a stone waterfall, creating a serene ambiance illuminated by subtle lights.
Home in Paradise
4.98 out of 5 average rating, 103 reviews

Vegas Tranquil Oasis Sparkling Pool/Spa+Slots+420

Contemporary Mid Century Modern. Huge Master suite with neon lights, chandeliers, a tub you'll Love. Immerse in the outside entertaining area with a hanging chair, lights, outside heaters, wind chimes, gas fire feature and waterfall alongside misters! Fun Faux Slots, heated spa, cool pool with a light show. Enjoy the TV and music in the pool. Lounge poolside in a backyard oasis. Inside there's a marble open shower. Gorgeous kitchen and dining space with TV in master bedroom and living room.

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 Paradise
4.85 out of 5 average rating, 209 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
A modern living area features a spacious gray sectional sofa and a glass coffee table. Natural light floods through large floor-to-ceiling windows, offering views of the city skyline. Decorative elements include a wall art piece and soft lighting, creating an inviting atmosphere.
Flat in Paradise
4.97 out of 5 average rating, 104 reviews

Ultimate Strip View Experience

Experience a unique Las Vegas retreat at Palms Place. Perched on the 19th floor, this luxurious high-rise condo blends modern sophistication with artistic elegance. Thoughtfully designed with upscale decor and exquisite art, it exudes a refined vibe. Step onto the private balcony for breathtaking, unobstructed views of the iconic Strip. Perfect for special occasions or a tranquil escape, this immaculate studio offers comfort, style, and an unforgettable Las Vegas experience.

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 Strip
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 Sunrise Manor
4.96 out of 5 average rating, 243 reviews

Suite de lujo Las Vegas

Esta adorable propiedad ofrece una estancia genial y fabulosa para los huéspedes. La habitación cuenta con una cama Queen muy cómoda y elegante .Tiene una cocina equipada y un baño privado para una ducha refrescante. Manténgase conectado con WiFi y TV con Netflix ,You Tube ,disfrute de estas comodidades (solicite una lista). Ya sea que esté explorando la vibrante ciudad o probando suerte en los casinos, nuestro estudio es la base perfecta para su aventura en Las Vegas.

Popular amenities for Winchester family-friendly rentals

When is the best time to visit Winchester?

MonthJanFebMarAprMayJunJulAugSeptOctNovDec
Avg. price$269 SGD$254 SGD$277 SGD$261 SGD$309 SGD$254 SGD$247 SGD$247 SGD$255 SGD$270 SGD$267 SGD$270 SGD
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