
Holiday rentals with a pool in Winchester
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Winchester
Guests agree: these homes with a pool 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.

Captivating City Views
Enjoy the comfort of knowing exactly what room you’ll be staying in by booking directly with us! Enjoy this rare corner suite at Palms Place Hotel featuring a wrap around 60 foot balcony offering sweeping views of the Las Vegas strip!Bask in the views of the twinkling lights as the sun slowly sets. There is a convenient indoor walkway that will take you to the action of the Palms casino floor and all the amenities that the resort has to offer!Revel in the suite life with this unforgettable stay!

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.

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.

Desert Oasis near Downtown Las Vegas
This is an awesome Palm Springs styled desert oasis to enjoy your Las Vegas experience! It has a spacious backyard equipped with an amazing pool, grill island, and multiple lounging areas. Enjoy a break from the desert heat with a dip in the pool of your private oasis! There is an office area with internet for remote work. All essentials that you may need for cooking, a Keurig, and a fully equipped laundry area are provided. Kick back and relax in this calm, stylish space. Lic. G71-06392

VEGAS Garden Oasis
Enjoy lounging outdoors in the shaded cabana or on the hammock, gathering around the fire pits or chilling in the newly remodeled home! Enjoy the heated hot tub & heated spacious pool. Drive times are only 2 min to the Airport, 8 min to the Strip, 12 min to Allegiant Stadium, and 14 min to the Convention Center. The home sleeps 8 comfortably w/ 3 Queen & 1 King bed! Great kitchen, living, laundry, pool, & outdoor space! Ultra fast 1000 Mbps internet. Pet friendly. Smoking outdoors ONLY

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.

Luxury Penthouse Suite | Amazing Strip Views!
This ultra modern 1 bedroom 2 bathroom Penthouse suite is all yours. Enjoy a spacious living room with a balcony that features breathtaking strip views! Fully stocked w/ plush towels, cotton sheets, dreamy mattress' & a full kitchen with all kinds of utensils for any level of cooking. Enjoy a resort style stay with pool & gym access, direct access to MGM casino, complimentary valet, high speed WIFI are one of many entertainment options. Walking distance to the world famous Las Vegas strip!

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**

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)

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.
Popular amenities for Winchester rentals with a pool
House rentals with a pool

Private Oasis with heated pool

Blissful Pool House 7mi to Strip

2 bedroom 1 bath house downtown. W/ big pool

Cozy Las Vegas Home, 7 miles from strip!

Mid Century Modern near STRIP w Pool, King Suite

4BR Private Home with Pool

We Love Families

Super Stylish ! Home with Pool Near the Strip !6)
Apartment rentals with a pool

Jockey Club 1 Bedroom Condo on LV Strip for 4

1 mi to Strip • Free Parking • No Resort Fee

Comfy 1BR Condo by Strip Pool/Parking/Gym/Hottub

Flamingo Bay 1 Bedroom

Vegas Condo Near Strip • Pools • Gated * Parking

Charming Resort style condo, Close to The Strip

Vegas Oasis! Spacious condo w/ pool 5 min to strip

Modern 1BR Condo Near Strip! FREE Parking/Pool/Gym
Other holiday rentals with a pool

51 FLR 1BR Suite, Strip View, Pool table, Sleeps 6

Mid-century Home near Strip/Downtown w/Heated Pool

Vegas Homebase, Pool & Central Spot

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

Stylish Strip, POOL, HOT TUB, Game Rm, Sleep 7

Relaxing studio near to the strip

Pet friendly Vegas stay W/ Pool

2100 SqFt Penthouse Suite : Strip Views! POOL GYM
When is the best time to visit Winchester?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $294 SGD | $306 SGD | $335 SGD | $361 SGD | $352 SGD | $318 SGD | $317 SGD | $316 SGD | $318 SGD | $349 SGD | $321 SGD | $325 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 with a pool in Winchester

Total holiday rentals
Explore 1,610 holiday rentals in Winchester

Nightly prices starting at
Winchester holiday rentals start at $13 SGD per night before taxes and fees

Verified guest reviews
Over 21,170 verified reviews to help you choose

Family-friendly holiday rentals
580 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 300 rentals that welcome pets

Rentals with dedicated workspaces
930 properties have a dedicated workspace

Wifi availability
1,560 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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- Tuscany Suites and Casino
- Las Vegas Strip
- Paris
- New York New York Hotel & Casino
- Valley of Fire State Park
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- Orleans Arena
- Downtown Container Park
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