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Family-friendly vacation rentals in Winchester

Find and book unique family-friendly homes on Airbnb

Quick stats about vacation rentals that are family-friendly in Winchester

  • Total vacation rentals

    Explore 720 vacation rentals in Winchester

  • Nightly prices starting at

    Winchester vacation rentals start at G$6,270 GYD per night before taxes and fees

  • Verified guest reviews

    Over 26,180 verified reviews to help you choose

  • Pet-friendly vacation rentals

    Find 270 rentals that welcome pets

  • Vacation rentals with a pool

    530 properties feature pools

  • Rentals with dedicated workspaces

    460 properties have a dedicated workspace

  • Wi-Fi availability

    720 of Winchester vacation rentals include wi-fi 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 favorite
Guesthouse in Paradise
4.97 out of 5 average rating, 123 reviews

Private Casita Oasis near Strip!

Modern Casita with private pool & B-ball Court Near the Las Vegas Strip. Experience the perfect blend of comfort and convenience in this brand-new, private casita. Located just 12 mins from the airport and 10 mins from the vibrant Las Vegas Strip, this retreat offers everything you need for a memorable stay. Making it perfect for both short and extended stays. Whether you're in town for business or leisure, this casita offers a peaceful escape with easy access to all the excitement of Las Vegas.

Guest favorite
Home in Las Vegas
4.97 out of 5 average rating, 149 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 favorite
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, 142 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.

Guest favorite
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, 186 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 favorite
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 favorite
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, 105 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.

Top guest favorite
A spacious bedroom features a king-size bed with a soft, white comforter and two matching pillows. Accent lighting from the wall sconces adds a soft glow. Modern furnishings include bedside tables with small plants. A sleek air conditioning unit is mounted above, maintaining comfort.
Apartment in Winchester
4.98 out of 5 average rating, 106 reviews

Beautiful luxury apartment near downtown.

Discover your oasis in Las Vegas: an exquisite 1-bedroom, 1-bathroom apartment with a luxury kitchen, all with modern, high-end finishes. Strategically located: ✈️ 10 minutes from the airport 🎰 14 min from the Strip 🌟 12 min from Fremont Street Experience Relax in a quiet and safe environment, ideal for escaping the hustle and bustle without losing comfort. Gourmet cuisine, premium rest, and quick connections to the action. Your perfect base to explore Las Vegas in style and peace!

Guest favorite
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.
Apartment 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.

Top guest favorite
A private outdoor space showcases a tranquil pool surrounded by lush palm trees and tasteful landscaping. Two lounge chairs are positioned beside the pool, with a small table that adds a functional touch. The area is well-lit by natural sunlight, creating a relaxing atmosphere.
Home in Paradise
4.96 out of 5 average rating, 123 reviews

Relaxing Pool & Spa! Single Story Close to Strip!

Located Just 1.5 miles from the south end of the Vegas Strip! Private pool & spa, Pool Table, BBQ, Ping Pong. *Strict anti gathering/party policy: Groups who exceed the amount of people/cars listed on reservation will be evicted without refund. 24/7 outdoor surveillance. *Maximum of 2 cars and 6 people. * Indoor Fireplace currently under repair. * Pool heating fee is $80/day. No fee to heat the spa. * Only accepting guests with previous stays & reviews.

Top guest favorite
Home in Las Vegas
4.93 out of 5 average rating, 108 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 favorite
Casa particular in Paradise
4.95 out of 5 average rating, 175 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 favorite
Home in Las Vegas
4.93 out of 5 average rating, 326 reviews

Close to Strip | Heated Pool, Game Room, sleeps 8

👉 Private Vegas home close to the Strip. ✔ Private pool, Resort-style backyard ✔ 4 bedrooms, Sleeps 8 ✔ Backyard games, Life-size games ✔ Game room, Poker table, Pool table ✔ Quiet area, Fast Strip access ✔ Fast Wi-Fi, Self check-in

Popular amenities for Winchester family-friendly rentals

When is the best time to visit Winchester?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$43,681 GYDG$41,173 GYDG$44,935 GYDG$42,427 GYDG$50,160 GYDG$41,173 GYDG$40,128 GYDG$40,128 GYDG$41,382 GYDG$43,890 GYDG$43,263 GYDG$43,890 GYD
Avg. temp10°C12°C16°C20°C25°C31°C34°C33°C29°C21°C14°C9°C

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