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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$6,275 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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Guest favorite
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, 148 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 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, 185 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
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, 104 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 favorite
A spacious pool area is featured with a separate spa and a swim-up bar. Palm trees surround the pool, showcasing a sunny patio area. The water appears inviting, enhanced by the clear blue sky above.
Guesthouse in Paradise
4.96 out of 5 average rating, 259 reviews

Sun's Vegas ABC Retreat

A guesthouse (casita) within a 1-acre compound that’s 8 minutes from the airport, 10 minutes to the Strip and less than 15 minutes from the new Allegiant Stadium. The casita consists of 3 mini-suites (a bedroom with private full bathroom), a living/dining room, full kitchen, laundry and powder room. Common area outside of the guesthouse includes the pool, spa, exercise room, pickle-ball court, bocce court and patio with a gas and an electric BBQs. FOR NO SHARING OF COMMON AREAS—See Below.

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, 102 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!

Top guest favorite
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.
Condo in Paradise
4.97 out of 5 average rating, 161 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.

Guest favorite
An outdoor space featuring a sparkling pool surrounded by a spacious patio. Lounge chairs are positioned near the pool, and a pink inflatable flamingo floats in the water. A dining area with a table and chairs is visible, covered by a large umbrella. Large glass doors connect the indoor and outdoor spaces.
Home in Las Vegas
4.9 out of 5 average rating, 219 reviews

MID CENTURY OASIS – 3BR&2BA – POOL

Newly renovated and thoughtfully designed. This single story Mid Century home is Luxurious and beautifully appointed, with high-end furnishings and linens. Conveniently located near Summerlin, 11 minutes from the Vegas Strip and 21 minutes from wonderful hiking or climbing at Red Rock. The home sleeps comfortably 6 w/ 2 Queen and 1 King bed . We offer Air Mattress! Great kitchen, living, laundry, pool, & outdoor space! *PLEASE NOTE; POOL IS NOT HEATED!!

Guest favorite
The open living space features a cozy seating area with light-toned furniture and a plush throw blanket, complemented by warm wood accents. A modern kitchen with sleek cabinetry and stainless steel appliances is visible in the background, while large windows invite natural light.
Home in Spring Valley
4.95 out of 5 average rating, 103 reviews

Resort Style Designer Home w/ Heated Pool

Welcome to The Oasis, a stunning designer home where every piece of furniture and decor was curated to leave a lasting impression. This single story resorts style home features high ceilings, big windows, modern pool & jacuzzi, brand new furniture and a completely private Entertainers backyard. The property is conveniently located 5-10 minutes from the Las Vegas Strip, 15 minutes to Harry Reid Airport, and 20 minutes from Red Rock Canyon!

Top guest favorite
Guest suite in Paradise
4.95 out of 5 average rating, 104 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 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, 172 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.

Superhost
Apartment in Paradise
4.86 out of 5 average rating, 237 reviews

Penthouse Suite @PalmsPlace Balcony-Jacuzzi

Perched on the top floor @ Palms Place Hotel, this stylish Penthouse Suite is 1300 sqft, w/ one bedroom, spacious kitchen & dining area. Large private balcony with jacuzzi and uninterrupted 180-degree views for that exclusive Vegas experience. Featuring a large, spa-like bathroom with dual sinks & Roman jacuzzi bathtub. Access to Palms Place amenities + Palms casino pools.

Popular amenities for Winchester family-friendly rentals

When is the best time to visit Winchester?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$43,714 GYDG$41,204 GYDG$44,969 GYDG$42,459 GYDG$50,198 GYDG$41,204 GYDG$40,158 GYDG$40,158 GYDG$41,413 GYDG$43,923 GYDG$43,296 GYDG$43,923 GYD
Avg. temp10°C12°C16°C20°C25°C31°C34°C33°C29°C21°C14°C9°C

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