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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 790 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 27,090 verified reviews to help you choose

  • Pet-friendly holiday rentals

    Find 270 rentals that welcome pets

  • Holiday rentals with a pool

    560 properties feature pools

  • Rentals with dedicated workspaces

    500 properties have a dedicated workspace

  • Wifi availability

    790 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 private pool is surrounded by comfortable lounge chairs. Colorful inflatable floaties in the shape of a flamingo and a unicorn rest in the water. String lights overhead add a festive touch to the backyard, with trees providing shade in the distance.
Home in Winchester
4.98 out of 5 average rating, 120 reviews

Amazing 4 Beds Pool Home 5 Mins to Las Vegas Strip

Welcome to Your Perfect Las Vegas Getaway! This beautiful 3-bedroom, 2-bathroom home is the ideal retreat for your next vacation. With 4 comfortable beds, this space can easily accommodate families, friends, or business travelers. Amenities: - 🏊 **Private Pool for refreshing dips - 🎮 **Games for all ages - 🌞 **Outdoor Seating** for relaxation - 🍳 **Fully Equipped Kitchen*with essentials - 📶 **High-Speed Wi-Fi & Smart TV** for connectivity and entertainment Your ideal Las Vegas retreat awaits!

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, 152 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 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, 261 reviews

Luxury Bungalow Arts District Fremont!

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
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, 111 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 favourite
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.
Flat in Winchester
4.98 out of 5 average rating, 114 reviews

Hermoso apartamento de lujo cerca del centro.

Descubre tu oasis en Las Vegas: un exquisito apartamento de 1 habitación y 1 baño con cocina de lujo, todo con acabados modernos y de alta gama. Ubicado estratégicamente: ✈️ A 10 min del Aeropuerto 🎰 A 14 min de la Strip 🌟 A 12 min de Fremont Street Experience Relájate en un entorno tranquilo y seguro, ideal para escapar del bullicio sin perder comodidad. Cocina gourmet, descanso premium y conexiones rápidas a la acción. ¡Tu base perfecta para explorar Las Vegas con estilo y paz!

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, 222 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
Place to stay in Las Vegas
4.95 out of 5 average rating, 411 reviews

Casa Azul | Boutique Villa Retreat with Pool + Spa

Nestled in the heart of Las Vegas, is an enchanting, coastal-themed gem. This private sanctuary, situated just minutes from the Strip, hints at a sense of signature curated hominess that is ubiquitous. Relax and unwind in a lush backyard, reminiscent of a secret garden. It is the perfect hideaway for couples, small families, or anyone who wishes to delight in the eclectic balance between a desire to escape yet still feel right at home. Business Lic. # G65-05603 - Owner Occupied

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, 106 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 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, 256 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.

Guest favourite
The pool area features a spacious swimming pool surrounded by comfortable lounge chairs and shaded cabanas. Bright teal umbrellas provide shade, while palm trees line the background, creating a relaxing atmosphere. Sunlight reflects off the water, enhancing the inviting setting.
Holiday home in Las Vegas Strip
4.93 out of 5 average rating, 150 reviews

Trump International the gateway to viva Las Vegas

Important: Reservation requires 48 hour in advance notice,  so please book as early as you can Did someone ask, "location, location, location?" This property is here to answer that question. Welcome to the glitz and glamour of the Las Vegas Strip. This resort is a launch pad to accomodate all of your potential needs i.e. vacation, business trip or just a stopover. This spotless 5-Star Resort will exceed your Vegas Dreams while keeping you comfortable and relaxed.

Top guest favourite
Guest suite in Las Vegas
4.96 out of 5 average rating, 612 reviews

Mid Century Dream Suite Close to Strip!

- Private suite with a spacious backyard hangout space - patio surrounded by carefully maintained flowers and trees. - Very Pet friendly! - Mid Century original vintage decor and furniture. - 77 walk score, 64 transit score, 55 bike score - close to every amenity! - 10 min drive to the Las Vegas Strip, 5 min drive to Fremont street/Arts District/Main Street, 15 min from the airport. - Keyless deadbolt entry. - Extremely safe neighborhood.

Guest favourite
Tiny home in Winchester
4.94 out of 5 average rating, 195 reviews

Casita de Yailin

This is an extension of the house. Private Room with independent entrance. It’s designed to provide an exceptional experience, all private nothing shared. located in good area with a quiet environment. Free Wifi, TV , kitchen, laundry and other amenities.. Pets are welcome ( Pets Fee applies) And It’s located 15 minutes from the international airport and 15 minutes from Las Vegas Strip.

Popular amenities for Winchester family-friendly rentals

When is the best time to visit Winchester?

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Avg. price$268 SGD$252 SGD$275 SGD$265 SGD$313 SGD$263 SGD$246 SGD$246 SGD$254 SGD$269 SGD$265 SGD$269 SGD
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