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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 $38 SGD 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 & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    60 properties have a dedicated workspace

  • Wifi availability

    80 of Guadalupe holiday rentals include wifi 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, 154 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 spacious bed is positioned against a wooden accent wall, creating a warm atmosphere. Two bedside tables hold decorative lanterns, providing soft illumination. Neutral-toned pillows complement the bedspread, while a colorful wall art piece adds a touch of character to the room.
Flat in Escalante
4.9 out of 5 average rating, 608 reviews

Stylish Studio with Sky Bar & City Views

New and exclusive Golden Coffee Studio, inspired by the history of Costa Rican coffee this apartment brings the best views of San Jose city. Walkable of the beaten heart of trendy gastronomic area Barrio Escalante, surrounded by the local vibes this place is on the best spot downtown for you to get ready and discover Costa Rica. One master room and a unique queen wallbed make this place an inviting and fun place for couples, friends and families. Spectacular amenities 100MBps Fiber optic Wifi

Guest favourite
An inviting outdoor area features a private heated pool surrounded by tropical plants and potted flowers. Comfortable seating options, including a hammock and lounge chairs, are positioned around the pool, with a cozy dining area visible in the background under soft lighting.
Villa in Mata Redonda
4.96 out of 5 average rating, 143 reviews

Cheerful private 4-Bedroom Villa. Heated pool A/C

For a group or a cozy couple, this bright and spacious home delivers comfort and style. Located in a quiet, modern, and safe neighborhood, you’re just minutes away from downtown. Great restaurants are close by and a block away from new Microsoft tower. 4 bedrooms (A/C), sleeps up to 9 , 3 full bathrooms & private heated pool. Fully equipped modern kitchen, stocked with staples and more. Starts at $195 per night for up to 4 guests, $35 per extra guest. Cleaning included. Come dive into city life.

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, 423 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 bright bedroom features a spacious bed with a dark blue throw blanket. Floor-to-ceiling windows provide an expansive view of the city and mountains. A bedside table holds a sleek lamp, while a textured area rug adds comfort to the wooden floor.
Flat in San Pedro
4.93 out of 5 average rating, 132 reviews

Exclusive Apartment in Downtown Costa Rica

This penthouse is in one of the most exclusive areas of Costa Rica, excellent restaurants, the nightlife is intense, full of life. The apartment has places to work inside the building, a gym, an pool, 24-hour security and the apartment is spacious, the view it has is impressive! day or night "it takes your breath away" its minimalist decoration gives you peace in a world "full of complications" …you are a winner, and you deserve a night that brings you closer to that top level you deserve!

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, 638 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.

Guest favourite
Flat in Escalante
4.92 out of 5 average rating, 126 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
Flat in Escalante
4.87 out of 5 average rating, 103 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.

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, 480 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.

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, 171 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.

Guest favourite
A modern living space is showcased with a sleek gray sofa facing a wall-mounted television. A minimalist dining area with two chairs is positioned near large windows offering expansive views of the cityscape and mountains. The concrete walls provide a contemporary ambiance.
Flat in Curridabat
4.95 out of 5 average rating, 144 reviews

Vivi's Hideaway

Enjoy this peaceful and centrally-located apartment, with sweeping 21st floor views of San Jose and the surrounding mountains. Fast internet, cool a/c, and a luxurious king sized, memory foam mattress await you after a day of exploring the Central Valley. Located in an exclusive high rise apartment, you will have access to one of the only rooftop pools in the central valley, a full gym, and inspiring coworking areas.

Guest favourite
Loft in Curridabat
4.89 out of 5 average rating, 306 reviews

BeST RANkED SuPERHOST * 18th Floor * KInG sIZE BeD

Studio Apartment on the 18th floor. Peaceful and centrally-located place. KING SIZE BED GREAT VIEW of the mountains. The apartment is close to supermarkets, shopping malls, restaurants, and cafeterias. Located in a beautiful and fancy neighborhood. Close to bus stops and San Jose Metro-Area Fast Uber rides. *** This building is smoke free, therefore is not allowed to smoke in any location nor in the apartment ***

Popular amenities for Guadalupe rentals with a pool

When is the best time to visit Guadalupe?

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Avg. price$73 SGD$73 SGD$74 SGD$74 SGD$71 SGD$69 SGD$63 SGD$64 SGD$63 SGD$68 SGD$71 SGD$79 SGD
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