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Vacation rentals with a pool in San Bernardo

Find and book unique homes with a pool on Airbnb

Quick stats about vacation rentals with a pool in San Bernardo

  • Total vacation rentals

    Explore 60 vacation rentals in San Bernardo

  • Nightly prices starting at

    San Bernardo vacation rentals start at $14 CAD per night before taxes and fees

  • Verified guest reviews

    Over 830 verified reviews to help you choose

  • Family-friendly vacation rentals

    20 properties offer extra space and kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wifi availability

    50 of San Bernardo vacation rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across San Bernardo rentals

  • 4.8 Average rating

    San Bernardo stays are highly rated by guests—averaging 4.8 out of 5!

Top-rated rentals with a pool in San Bernardo

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

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Top guest favourite
Home in La Florida
4.94 out of 5 average rating, 168 reviews

House for 5 people • 2 bathrooms • Large garden • A/C • 2 parking spaces

House for 5 people with 2 bedrooms + living room: 1 double bed, 3 single beds. Comfortable and functional 2-storey house, fully equipped for large groups. The main feature is the 90 m² private garden: safe for children, perfect for barbecues and with a view of the Cordillera. It includes hot/cold AC and 2 parking spaces inside. Smoking is prohibited inside the accommodation, with a $100 fine for using the air conditioning. Located in La Florida with a bus 30 m away. Near Estadio Bicentenario and the Florida outlet.

Guest favourite
A traditional Chilean architecture is featured, with a two-story facade adorned in green. Natural wood elements are visible, complemented by lush greenery and flowering plants. Multiple windows allow for plenty of sunlight, while the inviting entry is framed by stone pathways leading to a manicured lawn.
Villa in Penaflor
4.93 out of 5 average rating, 114 reviews

Villa Miraflores

Discover the charm of Villa Miraflores! With the calm of its garden and large common spaces, it is the ideal place to escape from the city in comfort throughout the year. The home consists of multiple spaces ideal for sharing: a fully equipped kitchen, living rooms, a quincho with a grill and cruceta, and a pool in summer. With its traditional Chilean architecture, exposed beams, double height in the living room and master bedroom, it is a unique place on the outskirts of Santiago.

Top guest favourite
A spacious bedroom features a comfortable bed adorned with a light green throw and neatly arranged towels. Natural light enters through large windows, illuminating a cozy seating area with a chair and small table. Two bedside lamps add subtle lighting to the room.
Apartment in Santiago
4.99 out of 5 average rating, 101 reviews

Prime apt w/fast wifi-AC-Long stay clean-Lastarria

Relax in this modern, renovated apartment, fully equipped for a perfect stay. Enjoy: - Split-system inverter air conditioning - High-speed Wi-Fi - Washer/dryer - Hair dryer and straightener - Bed with soft cotton sheets - Nespresso coffee maker - Secure building with 24/7 concierge - Located in the heart of the Lastarria neighborhood, just steps away from Santiago's best restaurants, cafes, museums, and attractions. Feel free to message me with any questions—I’d be happy to help.

Guest favourite
Cabin in Pirque
4.94 out of 5 average rating, 261 reviews

Private mountain cabin + Hot tub + incredible view

Escape to the mountains just 45 minutes from Santiago. Enjoy a private mountain retreat at 1,200 meters above sea level, surrounded by nature, fresh air, and incredible views of the Cajón del Maipo. Your stay includes exclusive 4x4 transportation from the private parking area to the cabin (10-minute uphill drive), making the arrival part of the adventure. Private XL hot tub Natural stream Covered terrace with gas grill Panoramic mountain views Satellite Wi-Fi Pet-friendly

Guest favourite
The exterior of a charming cabin is shown, featuring a sloped roof and wooden accents. Lush greenery surrounds the property, with flowering shrubs in the foreground. A small patio with seating is visible, complementing the peaceful setting.
Cabin in Alto Jahuel
4.93 out of 5 average rating, 123 reviews

Beautiful cabin, Maipo Valley Chile, wineyard zone

If you want accommodation on the wine route of Maipo Valley, Chile, this location is ideal, private cabin in a family house located on a farm of 5,000 square meters, access to the services you require, laundry, pool and gardens. Preparation of roasts and typical meals, upon request. Located in the village of Alto Jahuel, 38 kms. south of downtown Santiago, mobilization at the door of the condominium. Easy access to vineyards in the sector, even some can be reached by foot.

Superhost
Apartment in La Florida
4.89 out of 5 average rating, 123 reviews

Studio for 2 people next to the Metro

Stay in a modern and cozy studio, fully equipped for two people, steps from the Bellavista de La Florida Metro. Perfect for couples, business travelers, or weekend getaways. Close to shopping malls, clinics, universities and stadiums. It is the perfect retreat for those seeking comfort, connection and good taste. This apartment is ideally located for quick and easy access to the mountain 🏔️, vineyards 🍇 and countryside 🌿, without losing the comforts of the city.

Top guest favourite
A comfortable sleeping area is showcased, featuring a spacious bed adorned with neutral-colored bedding. Two bedside lamps provide soft lighting, while potted plants enhance the natural feel of the room. A stylish area rug lies beneath the bed, complementing the warm wood tones of the floor.
Apartment in Santiago
4.99 out of 5 average rating, 157 reviews

Welcome to Santiago/metro Toesca

Disfruta de la comodidad que ¡Welcome to Santiago! tiene preparado para ti, conoce los lugares icónicos de la ciudad, estamos a 5 minutos del metro estación TOESCA, a 15 del Movistar Arena, a 10 del parque de diversiones Fantasilandia y a pasos del parque O'Higgins. Contamos con todo lo necesario para que tu estadía sea lo más cómoda posible, cocina, baño y living-comedor totalmente equipadas. Atención!! La temporada de piscina inicia el 24 de noviembre del 2025

Top guest favourite
A spacious outdoor area is visible, featuring a well-maintained lawn and a swimming pool. The house is set against a backdrop of mountains, with large trees providing shade. The scene captures a peaceful natural environment, ideal for relaxation.
Cottage in Pirque
4.9 out of 5 average rating, 151 reviews

Mountain plot in Pirque near Santiago

This nice country house allows you to exclusively share a plot for family use only that consists of a 210 sq. meter construction on a 5,800 sq. meter plot. The place is in an absolutely natural setting, close to important vineyards and the Maipo River, with a gazebo and children's games. The house is also delivered ozonated to provide security and tranquility to visitors. The characteristics of the environment do not allow parties, visits or bothersome noise.

Top guest favourite
The living area features a comfortable sofa with accent pillows, paired with a modern coffee table on a textured rug. A window allows for natural light and offers a view of the surrounding area. An air conditioning unit and a washing machine are visible in the space.
Condo in La Cisterna
4.94 out of 5 average rating, 104 reviews

Depto. familiar para 5 · Metro · Parking

Enjoy Santiago in this comfortable apartment for 5 guests, just 200 m from La Cisterna Metro and with parking. Ideal for families or groups. It features 1 bedroom with a double bed, another with bunk beds, and a sofa bed. Fully equipped kitchen, fast WiFi, Roku TV, air conditioning, and washing machine. Strategically located near a mall, supermarkets, and restaurants. Secure building with 24/7 concierge. Highly rated for location, comfort, and cleanliness

Guest favourite
A modern living area features a sleek black sofa adorned with bright yellow cushions. The open kitchen boasts contemporary appliances and a stylish bar area, offering a functional space for cooking and dining. Natural light fills the room, enhancing the soothing color palette.
Apartment in La Cisterna
4.96 out of 5 average rating, 56 reviews

New Modern and Cozy Apartment WIFI + Parking

Welcome to your new space in La Cisterna! This new apartment, with modern and cozy furnishings, is perfect for your stay. Just steps from Lo Ovalle metro station, with supermarkets and shops nearby. Enjoy a full kitchen, comfortable bed, and a terrace with lovely views and parking. Ideal for travelers seeking comfort and style. Live a one-of-a-kind experience in a vibrant and well-connected environment. Book now and enjoy your stay!

Top guest favourite
A natural stone pool is situated in a green, grassy area surrounded by lush trees and foliage. A covered seating area is visible nearby, providing shade and comfort. The scene is illuminated by daylight, enhancing the tranquil outdoor environment.
Vacation home in San José de Maipo
4.98 out of 5 average rating, 186 reviews

Faldas del Punta Dama mountain lodge.

Treat yourself to a pleasant mountain experience at Lodge “Faldas del Punta Dama”. If you want to relax, be calm and comfortable amidst native flora and fauna, this is an excellent option. This cabin has a lovely view. You can be very comfortable in the hot water tub, go trekking in the area, enjoy a delicious meal, enjoy the large garden with a stone pool and natural spring water. Reconnect with nature at this unforgettable escape.

Top guest favourite
The exterior of the house features rustic elements with wooden beams and large windows. Soft lighting from hanging lanterns creates a cozy ambiance. A seating area with colorful cushions is positioned along the stone pathway, enhancing the inviting atmosphere of the outdoor space.
Home in Pirque
5 out of 5 average rating, 20 reviews

Peace and nature

Enjoy this cozy and spacious house located in the hills of Pirque, surrounded by a unique natural environment and panoramic views. We have all the comforts to be a couple, ideal for lovers of cooking, relaxation, tranquility and connection with nature. The house has a large living space, equipped dining room and kitchen. Relax in a stone pool, and enjoy a hot tub (May to October) with a view of the valley.

Popular amenities for San Bernardo rentals with a pool

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