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Holiday rentals with a pool in Guadalupe

Find and book unique homes with a pool on Airbnb

Quick stats about holiday rentals with a pool in Guadalupe

  • Total holiday rentals

    Explore 80 holiday rentals in Guadalupe

  • Nightly prices starting at

    Guadalupe holiday rentals start at $50 NZD per night before taxes and fees

  • Verified guest reviews

    Over 2,670 verified reviews to help you choose

  • Family-friendly holiday rentals

    10 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    60 properties have a dedicated workspace

  • Wi-Fi availability

    80 of Guadalupe holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Guadalupe rentals

  • 4.9 Average rating

    Guadalupe stays are highly rated by guests—averaging 4.9 out of 5!

Top-rated rentals with a pool in Guadalupe

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

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Guest favourite
A spacious bed with neutral-toned bedding is positioned near large glass windows, offering a nighttime city view filled with twinkling lights. Soft curtains frame the windows, complementing the warm color palette of decorative pillows arranged on the bed.
Home in Curridabat
4.94 out of 5 average rating, 168 reviews

Smart loft en el corazón de la Ciudad A/C y wifi

Disfruta de la tranquilidad de este smart loft, elegante y céntrico con vista a la ciudad! Ideal para relajarse. Cuenta con todos los servicios necesarios para hacer de tu estadía la más agradable con la más alta calidad. Su ubicación es favorable ya que se encuentra cerca de restaurantes, centros comerciales y supermercados. Está a solo 15 min del casco central de San José. Cuenta con una gran cantidad de amenidades como piscina temperada, cine, sala de estudio, gimnasio y área de coworking.

Top Guest favourite
Loft in Curridabat
4.94 out of 5 average rating, 151 reviews

Loft con balcón vista panorámica y parqueo privado

Te ofrecemos un aparta en un piso 18, con vista panorámica y brisa fresca. Este loft moderno combina estilo y comodidad con un balcón integrado, cortinas blackout para mayor confort, wifi y parqueo privado. En el piso 25 contamos con una piscina infinita, área de iworking y más. Estamos ubicados en una zona segura y céntrica de Curridabat, donde tendrás todo a tu alcance. Como Súper Anfitrión Top 10% en Costa Rica, garantizo atención rápida y dedicada para que tu estadía sea inolvidable.

Guest favourite
A rooftop pool is seen overlooking expansive views of the city and distant mountains. The pool's water appears inviting under a clear blue sky. Lounge chairs are positioned nearby on a tiled deck, providing space for relaxation.
Apartment in Curridabat
4.86 out of 5 average rating, 104 reviews

Rooftop Pool - AC - Gym - In Unit W/D - iFreses 6c

New Studio Apartment in a Brand New High Rise Building. Great location, Walk Score of 90 ("Walker's Paradise Daily errands do not require a car.") Queen size bed, couch, 50 inch smart TV. The building has every amenity you could wish Rooftop pool, Movie Room, iWork area, coWork Area, Game Room, Gym, Landry Room, Art Room and many many more. Very close to Super Market (Automercado), Coffee Shops. Just 11 minute bus ride to Downtown San José Or Just $3 Uber ride to Downtown San José

Guest favourite
Apartment in Escalante
4.95 out of 5 average rating, 152 reviews

Cálido estudio en Barrio Escalante

Vive la experiencia de Barrio Escalante, la zona más vibrante y gastronómica de la ciudad. Este apartamento combina elegancia y confort, ofreciéndote un espacio ideal para descansar después de explorar restaurantes, cafeterías y bares únicos, todos a pocos pasos de tu puerta. Todo en un piso 13 con una hermosa vista con los mejores atardeceres y sin dejar de lado la posibilidad de tener acceso autopistas que conectan con otros destinos turísticos cercanos, como volcanes, montañas y playas.

Guest favourite
A spacious living area showcases a comfortable bed with blue accent pillows, facing a kitchenette with modern appliances. A dining table is positioned nearby alongside blue chairs. White shelving units provide storage, while a patterned chair adds a touch of style to the room.
Apartment in Curridabat
4.93 out of 5 average rating, 194 reviews

Apartamento Ifreses: limpio/balcón/WiFi/escritorio

El espacio es muy cómodo ya que está equipado con utensilios de cocina, mesa de trabajo, wifi, tv, aire acondicionado, sillón individual, sillón para dos personas, estantes, closets, etc que lo hacen muy acogedor. Además cuenta con un balcón con puertas corredizas que permite disfrutar de hermosas vistas hacia San José y montañas, atardeceres increíbles y aire fresco. La mayor parte de las calificaciones destacan la limpieza del espacio, algo que particularmente nos preocupamos en ofrecer.

Guest favourite
A spacious bedroom features a wooden bed against a backdrop of large windows, providing a panoramic view of the urban landscape below. The room is equipped with light-colored bed linens and a nearby white cabinet, enhancing the minimalist design.
Loft in Curridabat
4.91 out of 5 average rating, 418 reviews

Studio con hermosa vista/ Amazing View Studio

Ubicado en el piso 23 de torre iFreses en Curridabat, cuenta con vista a la zona Sur de San José. Dentro del estudio encontrá todo lo necesario para su estadía, podrá hacer uso de las amenidades del condominio como la piscina y iwork. Located on the 23rd floor of iFreses tower in Curridabat, with great view of the south of San José city. Inside, you will have all that you need. You could use some of the amenities of the condo like pool and iwork. Check-in 3:00pm and Check-out 11:00am.

Guest favourite
A stunning view of a sunset over the city skyline is captured, with vibrant orange and yellow hues blending into the sky. The horizon features silhouettes of distant mountains, while glass railings enclose a rooftop pool setting, reflecting the warm colors of dusk.
Loft in Curridabat
4.86 out of 5 average rating, 632 reviews

Amazing View at 20th SJO Floor Loft! Parking&Pool

There is no better way to experience the beauty of San Jose than by sleeping in the heart of the city with a spectacular vista of the north of the capital. The landscape of the Irazú volcano on the horizon will be the perfect complement to enjoying the sunrise in your bed. This apartment is perfect to start your experience in Costa Rica, relax after a business trip, or spend a romantic night with your partner. All from a privileged area within a walking distance of restaurants and shops.

Top Guest favourite
Apartment in Escalante
4.95 out of 5 average rating, 114 reviews

Tastefully Furnished Penthouse + Rooftop Pool

Lets chat for a FREE early check in 24/7 security extremely safe building and neighborhood Get up in the morning in this magnificent penthouse with the most magnificent view of Irazú and Barva Volcano, enjoying a cup of the most amazing costarican gourmet coffee. Get on to the amenities to enjoy a relaxing morning/sunset dip at the pool and workout in our fully equipped gym or grab a meal in one of the more than 80 restaurants in a 5 block radius following a nice pool table session

Guest favourite
Apartment in Escalante
4.87 out of 5 average rating, 100 reviews

*NEW* Luxury Condo | Stunning Views

Luxury condo with stunning views of the mountains & city. Just footsteps away from trendy coffee shops, bustling bars & over 50 restaurants. Located just 25 minutes from the airport. The building has 24/7 security, swimming pool & gym. This modern & professionally decorated condo offers a fully equipped kitchen, Full Size bed + a Queen pullout sofa bed. High Speed Wifi, AC & Smart TV’s in the bedroom & living room. This comfortable & cozy space truly feels like a home away from home.

Guest favourite
A cozy bedroom is highlighted by a tufted headboard and plush bedding. Soft lighting is provided by two bedside lamps. Artwork featuring Alice in Wonderland decorates the wall above. A large window offers expansive views of the city and landscape beyond.
Apartment in Mata Redonda
4.97 out of 5 average rating, 202 reviews

Whimsical 27th Floor Apt, King Bed, AC, Parking

Victorian “Steampunk” Alice in Wonderland inspired apartment! Located on the 27th floor, our comfortable apartment boasts amazing views of the city. Originally a 2-bdrm floorplan, this unit was converted into a 1-bdrm, making it larger than most 1-bdrm units in SECRT Sabana. Safe building, central location, within walking distance to the National Stadium, La Sabana Park, restaurants, and supermarkets. SECRT Sabana is a funky building, famous for its fun Alice-themed common areas.

Guest favourite
Apartment in Mata Redonda
4.98 out of 5 average rating, 115 reviews

SECRT Sabana 31st | A/C, Parking & View

Modern studio on the 31st floor of SECRT Sabana with an incredible view of the city and mountains. Enjoy unique sunrises and sunsets from the top level. The space includes AC, a Queen bed, equipped kitchen, smart TV, free parking in the building, and a peaceful environment to relax or work with total privacy. Located near restaurants, supermarkets, La Sabana, and with great access to transportation. Ideal for business trips or couple getaways. We look forward to hosting you!

Top Guest favourite
A modern studio is displayed with a cozy sleeping area featuring a spacious bed. A dining table is set with elegant glassware and decorative elements. Large windows allow natural light to brighten the room, complemented by soft curtains. A wall-mounted TV completes the inviting atmosphere.
Loft in Escalante
4.98 out of 5 average rating, 106 reviews

Apartamento en Escalante Olive Loft 14th

Un Moderno y elegante estudio en el piso 14, con una vista increíble al atardecer. Ubicado en el corazón de Barrio Escalante, cerca de bares y excelentes restaurantes de gran variedad gastronómica, frente a una de las mejores 100 cafeterías del mundo, Perfecto para parejas, viajeros solos o nómadas digitales que buscan comodidad en una ubicación segura y caminable. Escalante es el epicentro cultural y gastronómico de San José, con vida local activa a cualquier hora del día.

Popular amenities for Guadalupe rentals with a pool

When is the best time to visit Guadalupe?

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Avg. price$96 NZD$96 NZD$97 NZD$97 NZD$94 NZD$91 NZD$82 NZD$84 NZD$82 NZD$89 NZD$94 NZD$104 NZD
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