Holiday rentals with a pool in Westchester

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Westchester

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

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Guest favourite

Apartment in El Portal

4.95 out of 5 average rating, 331 reviews

Resort Like Exquisite 1 Bedroom Apartment & Pool

Beautiful property close to Downtown Miami and Miami Beach. This apartment has its own private courtyard to enjoy outside dining & bar kitchen, which includes: refrigerator, microwave oven, ice maker, dishwasher, a Keurig Coffee Maker and a single cooktop. Central Air Conditioning. Washer/Dryer and two TVs. Free WiFi/Internet access, one parking space and use of the shared swimming pool. The apartment and pool are both professionally cleaned 🧼 Awesome place to stay in Miami, close to everything!

Guest favourite

Home in Hollywood

4.79 out of 5 average rating, 121 reviews

Amazin spacious 4/2 Pool Home in Hollywood FLL-MIA

Modern living at its finest while vacationing in this Home-away-from-Home: -4 large bedrooms -2 full size bathrooms -fully furnished with modern contemporary Decor. -R1 queen -R2 queen -R3 king -R4 queen -Sofa bed in TV room Large pool w/ screened patio to enjoy outside , you will still be able to sun bathe but NO bugs. Home has a big kitchen, which is fully equipped ,and it also has an eat in kitchen area +a formal dinning area. Some furniture was update. - Free BBQ grill, you will need gas

Guest favourite

Condo in Lake Ridge

4.99 out of 5 average rating, 139 reviews

#1 Luxury Resort Style Fort Lauderdale EPIC POOL

ADULTS ONLY PROPERTY 21+, Welcome to PoolHouse FTL. Enter the gates and feast your eyes on this chic, modern, and luxurious resort style oasis. Each of the one bedroom bungalow style apartments open directly onto the enormous travertine pool and sun deck, and EPIC pool that is heated year round. Private, gated, surrounded by lush tropical landscaping. You may cancel all your plans, and lay poolside for your entire stay. Located minutes from the beaches, downtown and the famous Wilton Manors.

Guest favourite

Villa in Pembroke Pines

4.88 out of 5 average rating, 213 reviews

Stunning Lake-Front Villa with Pool & Spa

This beautifully renovated and spacious villa is the perfect spot for your South Florida getaway! Located in the family-friendly neighborhood of Pembroke Pines, this home boasts a large heated swimming pool and spa, furnished deck and stunning lake-front views. The interior features 2 large living rooms, 2 dining areas, a state-of-the-art kitchen, 5 comfortable bedrooms and 2 modern bathrooms. Also included are free parking, laundry room, gaming tables, 6 TVs, BBQ grill and high-speed wifi.

Guest favourite

Home in Davie

5 out of 5 average rating, 102 reviews

Modern pool home on lake near Hardrock FLL airport

Luxurious lakefront pool home, newly remodeled modern design, conveniently located within minutes of Hardrock Hotel & Casino and Ftl airport. Spacious enough for the whole family. Private and quiet. Sit by the pool and watch the beautiful Florida sunsets or head east 15 minutes to the famous Ft. Lauderdale beach. Enjoy the firepit, light up the BBQ, and enjoy the day poolside. Publix is located less than 1 minute away. Looking for a rental car for your trip? Message me today for more info!

Superhost

Home in Miami

4.91 out of 5 average rating, 195 reviews

#Miami Amazing Pool, Mini Golf, Basketball

Experience pure charm in this completely renovated treasure, perfectly situated for an unforgettable Florida getaway. The secluded backyard offers a sanctuary of happiness and tranquility, boasting a heated pool, captivating gazebo, barbecue haven, playground, luxurious recliners, chic sofas, and an entertainment hub complete with mini-golf and basketball court. A fenced oasis awaits – providing the ideal setting for memorable moments and shared laughter. Your ultimate escape begins here!

Superhost

Home in Rio Vista

4.84 out of 5 average rating, 151 reviews

Large Waterfront House with Pool 4bd/2ba

This Waterfront paradise, located downtown Lauderdale! This beautifully redesigned home has 4 BR, 2 full BA with tubs, and comfortably sleeps 8. Downtown Las Olas Boulevard is a 5 minute walk, and the beach is a 7 minute drive. No Parties, locals and spring breakers Enjoy the backyard pool , BBQ grill, patio furniture, and dock on the Tarpon River. We also offer plenty of local recommendations in the house guide! This rental is for renters responsive renters, not for young groups.

Guest favourite

Apartment in Victoria Park

4.99 out of 5 average rating, 106 reviews

Cozy Oasis for 2 w/ Insta-worthy Tropical Pool*

👙 New resort-style tropical pool & hottub 🏠 Super stylish & comfortable 🌆 2 mi to beach & downtown. 🛌🏽 Westin Heavenly Bed; ultimate comfort and sleep ✅ Kitchen is fully stocked; ready for gourmet cooking 🏖️ Beach chairs, towels, & sport-brellas available for you. 🐶 Low pet fee; bring your furry friends! 💻 WFH ready - Super high speed internet. 📺 Large Smart TVs in both bedrooms & living rooms 😊 Hosts with a service heart (we’re here to make your trip perfect!)

Superhost

Home in Miami

4.84 out of 5 average rating, 232 reviews

Top rated pool home in the Heart of Miami!

Remodeled luxury home In heart of Miami boasts lots of natural lighting & great amenities.This Pool home is great for lounging. Swim & relax outdoors. Be entertained indoors w/game room filled w/fun family games and large screen TVs. Modern kitchen, stainless steel appliances,washer,and dryer. Large Master bedroom, spa-like en-suite,all pillow top mattresses. Centrally located, close to grocery stores, restaurants, shops,beaches,& clubs. Over 100 positive reviews :)

Guest favourite

Home in Fort Lauderdale

4.9 out of 5 average rating, 256 reviews

Heated Private Pool | King Bed & Hammock

Beautiful home in Fort Lauderdale with the city and beach within 10min Uber/Lyft. You may not even need to leave as you will find your own piece of paradise in the backyard right in the middle of a wonderful city. Completely Private pool, grill, beach supplies including towels, shampoo/conditioner, stocked kitchen, and kids toys with pack 'n play. Full-size washer and dryer on site for guests. Approved City of Fort Lauderdale Vacation Rental, Certificate #170 1190

Superhost

Apartment in Miami

4.9 out of 5 average rating, 168 reviews

Happy Vibes, 1 bed apt.,Free Park, POOL access,

Comfy 1 bedroom apartment for up to 4 guests. Designated parking space is very close to front door. Close to restaurants, supermarket, banks, liquor stores and more, all just a short walk. Apartment is fully equipped and there is a laundry on site, WiFi is included and there is a 65" TV. This is suitable for up to 4 people, there is 1 King size bed and a sofa bed for 2 persons. We are 420 friendly and cater to adults Pool access from 8:00am-dark

Guest favourite

Guesthouse in Coral Way

4.94 out of 5 average rating, 139 reviews

Chic Guest house with pool, hot tub and bbq area

Enjoy a stylish experience at this centrally-located place. Close to everything miami has to offer Some answers to common questions below —— About 7 minutes from the cruise ship terminals (virgin, carnival, Royal Caribbean, Norwegian cruise lines etc About 10-15 minutes from Miami International Airport Yes the pool and backyard is private and you won’t be sharing with any other guests. You are the only guests when staying on my property.