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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 $42 AUD 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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Top Guest favourite
Loft in Curridabat
4.94 out of 5 average rating, 150 reviews

Loft with a balcony, panoramic view, and private parking

We offer you an apartment on the 18th floor, with a panoramic view and cool breeze. This modern loft combines style and comfort with an integrated balcony, blackout curtains for added comfort, wifi, and private parking. On the 25th floor we have an infinity pool, iworking area and more. We are located in a safe and central area of Curridabat, where you will have everything at your fingertips. As a Top 10% Superhost in Costa Rica, I guarantee fast and dedicated attention to make your stay memorable.

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
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 with a beautiful view/ Amazing View Studio

Located on the 23rd floor of Torre iFreses in Curridabat, it overlooks the South area of 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, 113 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
A modern kitchen with sleek dark cabinetry and stainless steel appliances is complemented by barstools with yellow upholstery. The cozy living area includes a light-colored sofa and a decorative table, with a vase of flowers adding a touch of color. Natural light fills the space.
Apartment in Escalante
4.97 out of 5 average rating, 145 reviews

Chic Escape in Trendy Barrio Escalante

Live Like a Local in the Heart of San José Welcome to our apartment in the vibrant and walkable neighborhood of Barrio Escalante. San José’s trendiest cultural and gastronomic district. Whether you’re here to explore the city, enjoy delicious food or simply relax, this thoughtfully designed apartment offers the perfect balance of comfort, style, and local experience. You will find yourself at walking distance from San Jose’s major attractions and some of the citie’s best restaurants

Top Guest favourite
Apartment in Mata Redonda
4.98 out of 5 average rating, 113 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
An outdoor infinity pool offers scenic views of the surrounding mountains and cityscape. Several lounge chairs are positioned along the poolside, while a smooth, tiled deck extends for relaxation. The tranquil water reflects the overcast sky, providing a serene atmosphere.
Loft in Curridabat
4.86 out of 5 average rating, 470 reviews

Modern studio with spectacular view and amenities

Good and easy access location near supermarkets, malls, night life centers, near a Main Street on Curridabat and near a train station. Spectacular amenities such as coworking space, gym, tempered pool and other common areas, as well as friendly staff in the building. The apartment is equipped with crockery and basic kitchen utensils and the bathroom is provided with soap, shampoo and conditioner. There is a private WiFi, a smart tv and A/C. There is one bed an one sofa bed.

Top Guest favourite
A large outdoor swimming pool is surrounded by a sunlit deck, featuring lounge chairs positioned along one side. The modern high-rise building stands in the background, with expansive glass windows reflecting the blue sky and sunlight.
Apartment in San José
4.89 out of 5 average rating, 506 reviews

Best location, cozy Apartment!

Beautiful condo in perfectly located apartment building. The whole place has a modern feel to it without losing a touch of home. The unit is composed of one bedroom with an ensuite bathroom, living room and deck to relax and enjoy the views, as well as a modern kitchen and laundry machine. This cozy and modern apartment is close to all the best restaurants and night life in San Jose, as well as museums and downtown. Major public transportation is right outside the door.

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

Warm studio in Barrio Escalante

Experience Barrio Escalante, the city's most vibrant and gastronomic area. This apartment combines elegance and comfort, offering you an ideal space to rest after exploring unique restaurants, cafes and bars, all just steps from your door. All on the 13th floor with a beautiful view of the best sunsets and without neglecting the possibility of having access to highways that connect with other nearby tourist destinations, such as volcanoes, mountains and beaches.

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, 105 reviews

Apartment in Escalante Olive Loft 14th

A modern and elegant studio on the 14th floor, with an amazing sunset view. Located in the heart of Barrio Escalante, close to bars and excellent restaurants with a wide variety of cuisine, opposite one of the 100 best cafés in the world. Perfect for couples, solo travelers or digital nomads looking for comfort in a safe and walkable location. Escalante is the cultural and gastronomic epicenter of San José, with active local life at any time of the day.

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 in the heart of the city, A/C and Wi-Fi

Enjoy the tranquility of this smart, elegant and centrally located loft with city views! Ideal for relaxing. It has all the amenities you need to make your stay the most pleasant with the highest quality. Its location is favorable as it is close to restaurants, shopping centers, and supermarkets. It's just 15 minutes from downtown San José. It has a large number of amenities such as a heated pool, cinema, study room, gym and coworking area.

Popular amenities for Guadalupe rentals with a pool

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