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Vacation rentals with a pool in Sierra Oeste

Find and book unique homes with a pool on Airbnb

Quick stats about vacation rentals with a pool in Sierra Oeste

  • Total vacation rentals

    Explore 310 vacation rentals in Sierra Oeste

  • Nightly prices starting at

    Sierra Oeste vacation rentals start at $28 CAD per night before taxes and fees

  • Verified guest reviews

    Over 8,980 verified reviews to help you choose

  • Family-friendly vacation rentals

    240 properties offer extra space and kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 180 rentals that welcome pets

  • Rentals with dedicated workspaces

    170 properties have a dedicated workspace

  • Wifi availability

    270 of Sierra Oeste vacation rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Sierra Oeste rentals

  • 4.8 Average rating

    Sierra Oeste stays are highly rated by guests—averaging 4.8 out of 5!

Top-rated rentals with a pool in Sierra Oeste

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

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Guest favourite
An indoor pool area is highlighted by sleek glass walls and a wooden ceiling with exposed beams. Sunlight filters through the skylights, reflecting off the calm water. Comfortable loungers are positioned alongside the pool, creating a relaxing atmosphere.
Cottage in Toledo

Casa de Campo El Encinar-Pool, Paddle Tennis, Barbecue

PADEL TENNIS / HEATED POOL / PICKLEBALL To preserve the tranquility of the surroundings and the rest of the neighbours, in this house *parties, celebrations, stag/hen parties, loud music, shouting or any behaviour that generates annoying noise are not allowed, both during the day and especially at night.* It has a heated pool, a paddle tennis court, pickleball, a barbecue, table tennis, and a pool table. All for the exclusive use of the tenants. It is accessed from a 5.5 km dirt track, and it takes 10 to 20 minutes.

4.9 out of 5 average rating, 135 reviews
Guest favourite
The house features a modern A-frame design with large windows, situated amidst lush greenery. Pine trees surround the property, adding to the natural setting. A pathway leads to the entrance, blending harmoniously with the landscaped garden.
Home in San Martín de Valdeiglesias

Casa Salamandra. With pool, by the swamp

Privileged environment, surrounded by pine forests next to the swamp, located between three of the most representative cities of Spain: Toledo, Ávila and Madrid. Very interesting design house in the shape of an A, with a lot of light, in the middle of nature, with views of the lake and mountains. Private garden of 1500 m2 with private pool. Furnished terrace with BBQ. 7 km from San Martín de Valdeiglesias (where all kinds of services are available). Possibility of carrying out a variety of aquatic activities.

4.92 out of 5 average rating, 122 reviews
Guest favourite
The wooden house is surrounded by lush greenery and stone landscaping. Sunlight filters through the trees, illuminating the natural elements. A stone seating area is visible in the foreground, with the house featuring large windows and a welcoming porch.
Cottage in Los Ángeles de San Rafael

The corner of your dreams.

Isolation, peace, and enjoyment in its purest state. A unique experience, a magical feeling of having your own wooden house in the middle of the mountain. A 3000m2 private oak wood house (for you) within a community with 24-hour security, swimming pools, hiking trails, golf courses, horseback riding, restaurants, a supermarket, a lake with water activities, and a spa. Each season offers its possibilities, from its cozy fireplace to its barbecues, through a spring full of flowers.

4.95 out of 5 average rating, 173 reviews
Top guest favourite
A dining table is elegantly set with blue plates and glassware, complemented by a vibrant floral centerpiece. The natural light enhances the glossy finish of the table, while large windows reveal expansive views of the city outside.
Loft in San Sebastián de los Reyes

Iconic and exclusive duplex up to 6 people

LUXURY DUPLEX in MADRID SWIMMING POOL/PADEL/ 2 GARAGE spaces 10 minutes from MADRID AIRPORT Designed for 1/2/3/4/5/6 people. Discover a duplex that redefines luxury in MADRID! This amazing space combines cutting-edge design with dazzling lighting. From the first moment, the infinity effect of the views will take your breath away, creating a magical connection with the horizon. Every corner radiates elegance and sophistication. A visual experience that will captivate you!

4.98 out of 5 average rating, 269 reviews
Guest favourite
A spacious dining area is highlighted by a large glass table surrounded by decorative chairs. Large windows provide panoramic views of the mountainous landscape. The ceiling features wooden beams, and a chandelier adds a touch of elegance to the inviting atmosphere.
Villa in Robledo de Chavela

Saint Bernard. Charming house in Robledo de Chavela

Spectacular villa with a unique charm and in a setting of great beauty in Robledo de Chavela. The country house, over 300 m2. 6 independent rooms: 5 bedrooms and the large living room with a sofa bed (and extra beds). Fully-equipped kitchen The 2,000 m2 plot is flat and comfortable, with wide and spectacular views of the mountains. You can visit San Lorenzo de El Escorial, Madrid, Segovia, Ávila and Toledo, Sierra de Guadarrama National Park, Sierra de Gredos, Pantano San Juan

4.97 out of 5 average rating, 60 reviews
Superhost
A spacious garden area is depicted, featuring a well-maintained lawn and a stone patio. Potted plants are arranged around the space, while trees and hedges provide a natural border. The house looms above, offering a glimpse of a balcony that overlooks the greenery.
Villa in La Estación

Very charming villa with a nice and spacious garden

It is a beautiful, charming and cozy stone and wood house, ideal to forget about the daily tensions of the city. It is very well equipped and well maintained. It has a stately garden in the front, very nice and independent. The house has 4 rooms facing the outside, with lots of light, and two separate bathrooms. A living room with a stone fireplace and a large window with beautiful mountain views. In the back, there is a large wooden porch for spending time together.

4.91 out of 5 average rating, 163 reviews
Top guest favourite
A rustic wooden stairway leads to a cozy area featuring a modern kitchen and a heated pool. A large screen displays a calming fireplace, enhancing the relaxed ambiance. Soft lighting from candles illuminates the space, highlighting the textured stone walls and wooden accents.
Tiny homes in Burgohondo

My Grandmother's Little House

In a picturesque village in the Alberche Valley, at the foot of the Sierra de Gredos, La Casita de Mi Abuela is the ideal getaway for couples. Cozy and unique, it has a heated pool with hydromassage inside, perfect for relaxing and enjoying. Surrounded by hiking trails and near the Alberche River, where you can cool off in summer, this house combines rural charm with modern comfort. A special place to disconnect and experience an unforgettable getaway as a couple.

4.96 out of 5 average rating, 202 reviews
Superhost
The image depicts a rustic orange house surrounded by tall pine trees and a rocky wall. A green gate provides access to the property. Rolling hills are visible in the background under a clear blue sky, showcasing the natural landscape.
Home in Cenicientos

House in the countryside to disconnect in Madrid. Animals

Old rehabilitated guard house, 150 m2, with a hall, living room with fireplace, two bedrooms, two bathrooms and a kitchen. The house is part of a 4-hectare estate, with elements of an old farm: garden, woodshed, henhouse, dovecote, two waterwheels, laundry, old fruit trees, etc. Ideal for relaxing, celebrating or enjoying stays with children, who can learn and participate in the tasks of caring for the animals and the farm. There are several walking routes nearby.

4.85 out of 5 average rating, 167 reviews
Top guest favourite
The exterior of a charming house is covered in vibrant autumn leaves, creating a striking contrast against a soft blanket of snow. Stone steps lead to the entrance, flanked by greenery and lampposts, while the landscape is adorned with seasonal colors.
Cottage in Miraflores de la Sierra

Amazing garden and charming villa in the mountains

A beautiful renovated house from the 60s on a large 1500m plot with a private pool and large trees. Tranquility and privacy in the heart of the forest in one of the most beautiful villages in the Sierra de Madrid. You can walk for days through the forests and mountains of Guadarrama National Park from your doorstep. Great for two families to share. Totally charmingly equipped. Fireplace, gas BBQ, ping-pong, trampoline, slide, basketball basket, Wi-Fi, and more

4.91 out of 5 average rating, 326 reviews
Guest favourite
The exterior showcases a two-story white building, featuring a welcoming entrance with a wooden door. Stone steps lead up to the entry, surrounded by lush greenery and colorful flowers. Bright sunlight illuminates the pathway, highlighting the natural beauty of the surroundings.
Townhouse in San Martín de Valdeiglesias

Fireplace + Barbecue + Comfort + Nature + WiFi

House in Urbanization with gardens and pool. On weekends, check in on Friday at 4:00 p.m. and check out on Sunday at 8:00 p.m. Two plants joined by the outside. In groups of 4, only the main floor will be opened. Terrace with barbecue. Air conditioning, heating and WiFi. 10 min walk to San Juan Pantano Living room with fireplace, full kitchen, 2 bathrooms, 2 bedrooms, and 1 separate dining/bedroom. An additional surcharge will be added to one-night bookings.

4.83 out of 5 average rating, 282 reviews
Guest favourite
A modern living area features a wooden TV stand with a minimalist design. A television sits on top, flanked by decorative plants. Above, shelves display small plants and an art piece. Natural light enhances the bright, open feel of the space.
Loft in San Sebastián de los Reyes

Amazing Views, Parking and Close to the Airport

ELEGANT LOFT WITH SPECTACULAR VIEWS. 10 minutes from MADRID AIRPORT. The luck of seeing everything from a unique perspective. Enjoying the light and views of this loft is a pleasure within your reach. Relaxing in it is finding the balance between details and simplicity in a unique atmosphere. Free Parking Rooftop pool in the summer months. 📌License number: VT-4679 📌Single Rental Registration: ESFCTU000028054000654561000000000000000000000VT-46793

4.92 out of 5 average rating, 640 reviews
Top guest favourite
An overview of a stone house surrounded by lush greenery is captured from above. The building features a traditional tiled roof, arched columns on the patio, and a circular stone seating area in the landscaped garden.
Cottage in La Estación

Villa with pool and mountain views

Enjoy the Sierra de Madrid in our beautiful stone house surrounded by greenery. You'll wake up every morning to an incredible garden with fruit trees and flowers, and you can have breakfast on a large terrace overlooking the mountain. Details such as the spiral staircase or the stone arches make our house a special and different place. The pool is super refreshing during these months and has night lighting so you can enjoy a swim under the stars.

4.97 out of 5 average rating, 130 reviews

Popular amenities for Sierra Oeste rentals with a pool

When is the best time to visit Sierra Oeste?

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