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Vacation rentals with a pool in Winchester

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Quick stats about vacation rentals with a pool in Winchester

  • Total vacation rentals

    Explore 1,750 vacation rentals in Winchester

  • Nightly prices starting at

    Winchester vacation rentals start at G$2,092 GYD per night before taxes and fees

  • Verified guest reviews

    Over 23,030 verified reviews to help you choose

  • Family-friendly vacation rentals

    560 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 280 rentals that welcome pets

  • Rentals with dedicated workspaces

    970 properties have a dedicated workspace

  • Wi-Fi availability

    1,680 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 rentals with a pool in Winchester

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Top guest favorite
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

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!

4.98 out of 5 average rating, 128 reviews
Top guest favorite
Guesthouse in Paradise

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.

4.97 out of 5 average rating, 138 reviews
Top guest favorite
A modern living area is presented, featuring a pool table and a large sectional couch. Floor-to-ceiling windows offer a view of the Las Vegas skyline, while LED perimeter lighting enhances the contemporary decor. A mounted television occupies one wall, contributing to the entertainment ambiance.
Condo in Paradise

2 Bedrooms-Strip View-PoolTable-3 King Beds-Arcade

Breathtaking view of the Las Vegas strip located in the Palms Place (A Palms Casino Property). This property features a spacious split suite configuration (1 bedroom suite + studio suite 1,865sqft. total). This ultra-modern decor suite offers a black stainless steel pool table, a full-size retro 80's arcade, and an in-bedroom Jacuzzi tub overlooking the strip. Floor to ceiling windows, motorized blinds and an expansive warp-around outdoor balcony with stunning views of the entire Las Vegas Strip

4.99 out of 5 average rating, 124 reviews
Top guest favorite
Home in Paradise

Ultra-Modern Vegas Suite | Strip Views + Balcony

Welcome to Palms 37! Experience Vegas in style at this ultra-modern, one-of-a-kind 1BR suite with a massive wrap-around balcony and breathtaking views of the Las Vegas Strip. This upgraded suite features sleek, custom interiors, a fully equipped kitchen, a convenient coffee bar, and floor-to-ceiling windows that bring the energy of Vegas right to your doorstep. Enjoy FREE high-speed Wi-Fi, FREE parking, and direct access to the Palms Casino. Just a short walk to the Strip, nightlife and dining!

4.98 out of 5 average rating, 125 reviews
Top guest favorite
A private backyard features a clear blue pool accompanied by a spa, bordered by a spacious patio. Tall palm trees and a brick wall provide a sense of privacy. A covered area with curtains offers shade, and a dining table is positioned nearby.
Home in Las Vegas

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.

4.9 out of 5 average rating, 591 reviews
Guest favorite
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.
Apartment in Las Vegas Strip

Highest 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

4.96 out of 5 average rating, 276 reviews
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

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.

4.98 out of 5 average rating, 117 reviews
Guest favorite
A serene pool area features a clear, unheated pool complemented by several lounge chairs and umbrellas, providing shaded seating. The modern home is visible in the background, surrounded by palm trees, blending outdoor relaxation with comfort.
Guesthouse in Paradise

Quiet Family Oasis / GolfView / NoChores / 3Bed1Ba

Take it easy at this unique and tranquil getaway. Mid-century home built right at the 9th hole at the Las Vegas National Golf Course. 10 min from the strip, 10 min from the airport Pet friendly :) Fully stocked kitchen. Newly rennovated pool (unheated sorry) with wet deck and underwater bench. Patio furniture, daybed, and lounge chairs Fiber internet, Washer/Dryer, Rock Band, and board games NOTE: Only 1 Bathroom **For the sake of future guests, NO parties, NO smoking inside**

4.94 out of 5 average rating, 187 reviews
Guest favorite
A luxurious outdoor space features a sparkling pool surrounded by palm trees and lush landscaping. Sunlight reflects off the water's surface, while a stone wall provides privacy. A set of steps leads into the pool, enhancing accessibility to the inviting area.
Home in Las Vegas

Escape to Modern Luxury-1.5 Miles to the Strip!

Located within 1.5 miles to the famous Las Vega Boulevard. See the "Resorts World" and "Sphere" as you pull up to the house and The Strat Hotel from the backyard! This ultra luxurious 4 bedroom 6,000 sq. ft. home sits on a half acre of lush landscape with an oversized new pool/spa (fee to heat), BBQ area, soft green grass, pool table, oversized bedrooms, gourmet kitchen, wine fridge, tv's in all bedrooms, modern soaking tub, walk in showers, 2 giant "En suite" bedrooms and much more.

4.97 out of 5 average rating, 218 reviews
Guest favorite
Home in Winchester

Licensed 2.5 Mi to Strip BBQ Pool Kings

Escape to this stunning, four bedroom two bath mid-century modern home where style meets comfort. Nestled in a quiet historical neighborhood very close to the downtown Fremont area, LVCC and the famous Las Vegas strip. This spacious retreat is perfect for families groups or anyone looking to unwind and enjoy tranquil relaxation away from the hustle and bustle of the strip. ⭐️ Keurig Pods*Tea*Creamer ⭐️Outdoor Propane BBQ ⭐️ Huge Pool *not heated ⭐️Washer~Dryer ⭐️King Beds

4.96 out of 5 average rating, 107 reviews
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

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.

4.97 out of 5 average rating, 183 reviews
Guest favorite
A private in-ground pool is surrounded by lounge chairs on a sunlit patio. A covered dining area with a table and chairs is visible near the pool, complemented by palm trees and lush landscaping in the background under a clear blue sky.
Home in Spring Valley

Group & Family Private Pool/Near Strip/Airport

Beautiful and spacious 4 bedroom 2 full bathroom with 5 beds. Home located a few miles to the strip, airport and china town. Master suite with private bathroom. Fully stock kitchen for any occasions. Dedicated workplace with fiber optic wifi internet. Pool table, corn hole, and a full-size arcade to play. Private in ground pool. Outdoor BBQ grill.

4.91 out of 5 average rating, 127 reviews

Popular amenities for Winchester rentals with a pool

KitchenWifiPoolFree parking on premisesAir conditioning

House rentals with a pool

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

SPACIOUs 5*Villa/Strip/POOL/CHEF Kitchen/Office

4.97 out of 5 average rating, 155 reviews
Top guest favorite
A tranquil outdoor space is highlighted by a heated pool and spa. Five fire pits illuminate the area, surrounded by lush greenery and palm trees. A shaded seating area is positioned nearby, offering an inviting spot for relaxation. The home exterior is visible in the background.
Home in Paradise

SPECTACULAR HOME WITH PRIVATE POOL AND MINI GOLF!

4.96 out of 5 average rating, 140 reviews
Top guest favorite
Home in Las Vegas

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

4.93 out of 5 average rating, 331 reviews
Guest favorite
Home in Paradise

35% OFF - Fabulous Single Story House/Casita

4.9 out of 5 average rating, 199 reviews
Superhost
An inviting backyard area is depicted at night, featuring a lagoon-style pool with a rockscape waterfall. Lounge chairs surround the pool, and palm trees are visible in the backdrop, enhancing the serene atmosphere of the outdoor space.
Home in Las Vegas

Super Private Vegas Oasis! Close to the Strip!0:)

4.84 out of 5 average rating, 435 reviews
Guest favorite
Home in Paradise

Family Retreat Private Pool Close to Strip/Airport

4.9 out of 5 average rating, 201 reviews
Top guest favorite
Home in Las Vegas

Newly Remodeled Pool Villa • Fast WiFi • Summerlin

4.98 out of 5 average rating, 106 reviews
Guest favorite
A private outdoor pool features clear blue water, surrounded by a stone patio. Several lounge chairs are placed nearby for relaxation, framed by lush greenery and light landscaping, creating a serene environment. Sunlight reflects on the water's surface, emphasizing the inviting atmosphere.
Home in Sunrise Manor

Modern 4-Bed Home *Fun, Pool, BBQ Grill ,Central*

4.92 out of 5 average rating, 159 reviews

Condo rentals with a pool

Guest favorite
A modern living space features a sectional sofa and a plush ottoman, positioned beneath large windows that offer expansive views of the city skyline. Soft neutral tones and stylish decor create a welcoming environment, while natural light brightens the room.
Condo in Paradise

Luxurious Condo Stunning Strip View at Palms Place

4.88 out of 5 average rating, 195 reviews
Superhost
A private Jacuzzi is situated on a balcony, revealing stunning panoramic views of the city skyline illuminated by twinkling lights. The evening sky casts soft blue hues, creating a tranquil ambiance. Nearby, champagne flutes and a bottle are placed elegantly on the tiled edge.
Condo in Paradise

PALMS PENTHOUSE / ROMANCE PENTHOUSE

4.89 out of 5 average rating, 372 reviews
Guest favorite
The exterior of the Jockey Club showcases a multi-story building with a neutral facade, prominently displaying the name 'Jockey Club' above the entrance. Surrounding high-rise structures and greenery are visible, contributing to the urban setting.
Condo in Las Vegas Strip

Jockey Club 1 Bedroom Condo on LV Strip for 4

4.84 out of 5 average rating, 625 reviews
Superhost
A modern living area is furnished with a spacious grey sofa and a glass coffee table. A large window offers views of the cityscape, while decor includes vibrant orange accent pillows. A stylish chair is positioned nearby, creating a comfortable atmosphere.
Condo in Paradise

Palms Place 19th Floor Corner Suite Strip Views!

4.79 out of 5 average rating, 335 reviews
Superhost
A well-appointed studio condo features a spacious bed, a cozy sofa, and a round glass dining table. A private balcony offers stunning nighttime views of the Las Vegas Strip, illuminating the skyline with vibrant city lights.
Condo in Las Vegas Strip

Gorgeous Strip View of Las Vegas/No Resort Fees

4.85 out of 5 average rating, 150 reviews
Guest favorite
A bright living space features a cozy gray sofa with yellow and white decorative pillows. Light flows through sheer curtains, enhancing the inviting atmosphere. A modern entertainment unit displays a large TV, while potted plants add a touch of greenery to the room.
Condo in Paradise

Modern 1BR Condo Near Strip! FREE Parking/Pool/Gym

4.94 out of 5 average rating, 132 reviews
Guest favorite
A wrap-around balcony features seating along with a small table, offering expansive views of the vibrant Las Vegas Strip illuminated at night. The surrounding structure is visible, framing the outdoor space.
Condo in Las Vegas Strip

2100 SqFt Penthouse Suite - Strip Views! POOL GYM

4.9 out of 5 average rating, 142 reviews
Top guest favorite
Condo in Paradise

Vegas Condo Near Strip • 2 Pools & Spas • Parking

4.87 out of 5 average rating, 254 reviews

Other vacation rentals with a pool

Top guest favorite
A modern living area features a large sectional sofa in front of a vibrant, abstract mural. Floor-to-ceiling windows provide natural light and a view of the balcony, while elegant curtains gently frame the space. The polished marble flooring reflects the room's colors.
Condo in Paradise

*NEW*2 Pools &Hot Tub+Adjustable Bed&massage chair

4.99 out of 5 average rating, 327 reviews
Superhost
Home in Las Vegas

2 bedroom 1 bath house downtown. W/ big pool

4.63 out of 5 average rating, 54 reviews
Guest favorite
Home in Paradise

New7 BDR Iconic Designer Home 5 min from Strip

4.95 out of 5 average rating, 84 reviews
Guest favorite
Condo in Paradise

Beautiful Palms Place Suite w/ Stunning Views

5.0 out of 5 average rating, 38 reviews
Superhost
Home in Las Vegas

Beverly After Dark | Luxe Pool 0.2 Mi to Strip

5.0 out of 5 average rating, 3 reviews
Guest favorite
Apartment in Paradise

High-Floor/1BR Apt/Strip View5Min to Strip

4.9 out of 5 average rating, 20 reviews
Guest favorite
An outdoor dining area features a wooden pergola providing shade over a table and chairs. Nearby, a sparkling swimming pool glistens under the sun, while lounge chairs are arranged on the surrounding patio. Lush greenery enhances the serene environment.
Home in Las Vegas

Vegas Trip! Pool-Hot Tub & Golf Strip!

4.83 out of 5 average rating, 95 reviews
Superhost
Apartment in Paradise

Beautiful Mountain High-Rise Views

5.0 out of 5 average rating, 4 reviews

When is the best time to visit Winchester?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$50,213 GYDG$51,886 GYDG$54,188 GYDG$55,443 GYDG$58,581 GYDG$56,908 GYDG$52,096 GYDG$51,886 GYDG$52,305 GYDG$57,326 GYDG$52,723 GYDG$53,351 GYD
Avg. temp10°C12°C16°C20°C25°C31°C34°C33°C29°C21°C14°C9°C

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