
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.

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.

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.

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.

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.

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.

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.

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.

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.

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)

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.

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.

The far away home B2
The beautiful 3-story home is 1 bedrooms , 1.5 bathrooms and with a den downstairs . The den room has a pool table . There are ceiling fans throughout the house. The upstairs primary room windows offer a rare wide strip view. There is the queen-size bed and TV in the bedroom . Additionally, there's a separate dining area with a kitchen combo featuring granite countertops.
Popular amenities for Winchester family-friendly rentals
Family-friendly home rentals with a hot tub

Private Pool & Hot Tub 4 BR Home-10min Strip

Sun's Vegas ABC Retreat

Luxury Penthouse Suite | Amazing Strip Views!

Private Oasis with heated pool

1900 SqFt House 25Ft Heatable Pool/Spa- Strip View

Blissful Pool House 7mi to Strip

15 Beds, Heated Pool, Near Strip | Vibes dot Vegas

New Modern 1BR/1BA+KIT*Near Strip~Free Parking&Gym
Family- and pet-friendly home rentals

House with Two Master Bedrooms – Pet Friendly

Family Retreat Private Pool Close to Strip/Airport

Strip View

Gorgeous 4BR house w. pool 12 minutes to the strip

Quiet Family Oasis / GolfView / NoChores / 3Bed1Ba

Cozy Downtown Space

25% Off Special- Retro Rad Single Story 3 bed

Guest house!
Family-friendly home rentals with a pool

Vdara 24th Floor | Fountain & Sphere View

Trump studio w/stripview, sphere

Vegas Homebase, Pool & Central Spot

2 bedroom 1 bath house downtown. W/ big pool

Modern Clean • EV charger• 10 Min to Strip/Airport

2.1 mi to Sphere & Strip, 3.5 mi to UNLV & Airport

Group & Family Private Pool/Near Strip/Airport

Lrg 2 bed/2 bath condo style unit near the strip.
When is the best time to visit Winchester?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| 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. temp | 10°C | 12°C | 16°C | 20°C | 25°C | 31°C | 34°C | 33°C | 29°C | 21°C | 14°C | 9°C |
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
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- Family-friendly rentals Clark County
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- Las Vegas Strip
- Valley of Fire State Park
- Lee Canyon
- Allegiant Stadium
- Lake Mead
- Fremont Street Experience
- Caesars Palace
- New York New York Hotel & Casino
- Fountains of Bellagio
- Las Vegas Motor Speedway
- Southern Highlands Golf Club
- Tuscany Suites and Casino
- Mandalay Bay Convention Center
- Seven Magic Mountains
- AREA15
- Cosmopolitan of Las Vegas
- The STRAT Hotel, Casino & SkyPod
- Venetian Expo
- Aria Resort & Casino
- Orleans Arena
- Canyon Gate Country Club
- Downtown Container Park
- Bellagio Conservatory & Botanical Garden
- Paris
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