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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, 223 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
Home in Las Vegas
4.97 out of 5 average rating, 146 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.

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 Paradise
4.92 out of 5 average rating, 184 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, 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.

Guest favourite
Home in Paradise
4.98 out of 5 average rating, 130 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 stunning night view of the Las Vegas Strip displays vibrant lights from various landmarks. The iconic Bellagio Fountain is illuminated, with the High Roller Ferris wheel and several hotels creating a lively skyline. The scene captures the bustling atmosphere of the city.
Flat in Las Vegas Strip
4.96 out of 5 average rating, 264 reviews

Loftiest VDARA Penthouse StripSphereBellagio views

Stylish City Centre Vegas Strip-Bellagio Fountain-located 941 SQFT 1BDR Vdara Hotel & Spa Suite Incredible Centre Strip views from the 54th 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, private bedroom with 1 PillowTop King size bed & stunning views. Double vanity bathroom, spa-like bathtub, large sit-in shower Kitchenette, large refrigerator. NON-SMOKING - penalties may occur

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.

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 Paradise
4.97 out of 5 average rating, 159 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.

Top guest favourite
Guest suite in Paradise
4.95 out of 5 average rating, 101 reviews

The Pirate’s Den - Private Pool & Pet Friendly

The Pirate’s Den is a private, pet-friendly Vegas guest suite with a separate entrance and exclusive use of the fully fenced yard and pool area during your stay. The property is owner-occupied, but set up similarly to a duplex: your indoor guest space and fenced Airbnb outdoor area are private to you. Just 5 minutes from the airport and about 10 minutes to the Strip. Best for respectful guests seeking a peaceful stay.

Top guest favourite
Home in Las Vegas
4.92 out of 5 average rating, 106 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 Paradise
4.95 out of 5 average rating, 167 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.

Top guest favourite
The image captures the iconic Stratosphere Tower set against a dramatic sky at sunset. Soft hues of orange and purple blend with wispy clouds, while palm trees frame the foreground, adding a touch of greenery to the urban view.
Guest suite in Las Vegas
4.9 out of 5 average rating, 121 reviews

Cozy Downtown Space

Completely Private, Large Studio Robust and equiped kitchenette, super comfortable bed, fast and reliable wifi, completely new bathroom and shower, private patio and yard. Private gated parking and secluded entrance. No contact with host unless requested *Sorry, no pets. I have a pet who uses adjacent areas *Outside smoking only *Rate is 1 person, extra guest is $20/night

Popular amenities for Winchester family-friendly rentals

When is the best time to visit Winchester?

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Avg. price$268 SGD$253 SGD$276 SGD$261 SGD$308 SGD$253 SGD$247 SGD$247 SGD$254 SGD$270 SGD$266 SGD$270 SGD
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