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Vacation rentals with a pool in Guadalupe

Find and book unique homes with a pool on Airbnb

Quick stats about vacation rentals with a pool in Guadalupe

  • Total vacation rentals

    Explore 80 vacation rentals in Guadalupe

  • Nightly prices starting at

    Guadalupe vacation rentals start at G$6,246 GYD per night before taxes and fees

  • Verified guest reviews

    Over 2,670 verified reviews to help you choose

  • Family-friendly vacation rentals

    10 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    60 properties have a dedicated workspace

  • Wi-Fi availability

    80 of Guadalupe vacation 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 favorite
Apartment in Curridabat
4.89 out of 5 average rating, 243 reviews

Studio at 24th floor - SJO view

Exclusivo apartamento en el Condominio iFreses piso 24, cerca del centro de San José, rodeado de tiendas, restaurantes, bares, barrios gastronómicos y más. Estacionamiento disponible por una tarifa adicional, no se permiten carros tipo pickup por tamaño/ Exclusive apartment at Condominio iFreses on the 24th floor, in the center of the city, surrounded by shops, restaurants, bars, gastronomic neighborhoods and much more. Parking available with an additional fee, no pickups are allow due to size.

Guest favorite
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, 414 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 favorite
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, 624 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 favorite
A rooftop pool area is depicted, featuring lounge chairs positioned beside the pool. The expansive surrounding area offers scenic views of the city and mountains, under a clear blue sky. Decorative planters enhance the contemporary design of the space.
Apartment in Curridabat
4.91 out of 5 average rating, 126 reviews

Rooftop Pool - AC - Gym - In Unit W/D - iFreses 7b

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 ammenity 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 favorite
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, 143 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

Guest favorite
Apartment in Escalante
4.94 out of 5 average rating, 108 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

Superhost
Apartment in Escalante
4.83 out of 5 average rating, 265 reviews

Urban Calm Retreat 9th

Located in San Jose’s trendiest neighborhood, with all the amenities you need for a nourishing stay in the city. This 24th-floor apartment has a balcony overlooking the city with incredible sunset views. Designed with the perfect balance of comfortable elements, local art, and vibrant plants, it has everything you need to rest and relax. This is the ideal base for exploring the neighborhood of Barrio Escalante, with dozens of independent restaurants, cafes, and shops just steps away.

Superhost
The open concept living area features a sleek black dining table with a decorative bowl at the center. A fully equipped kitchen is visible, showcasing modern appliances including a refrigerator and microwave. Natural light illuminates the space, enhancing the contemporary design.
Apartment in Escalante
4.86 out of 5 average rating, 262 reviews

★Luxurious Apt★ | Panoramic View, Pool, Gym + Pkg

Relax at our luxury apt at a prime location from which you can easily experience all of San Jose. Marvel at the mesmerizing views from the 23rd floor of a modern, industrially designed building, in the heart of Barrio Escalante. Perfect blend of luxury comfort & convenience with a rich amenity list is there to satisfy your every need. • Fully Equipped Kitchen • Queen Bed • Flat-Screen TVs • Open Concept Design Living Area • Pool • Gym • Free Private Parking Learn more below!

Guest favorite
Apartment in Escalante
4.95 out of 5 average rating, 147 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.

Guest favorite
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, 167 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.

Top guest favorite
Apartment in San José
4.88 out of 5 average rating, 395 reviews

10th floor Apartment w/ Sky-Level Pool in San José

Private, comfortable, and strategically located in the heart of Curridabat. This studio on the 10th floor of the iFreses building is perfect for couples, students, or travelers seeking a quiet and functional space. It offers all the essentials for a pleasant stay and is surrounded by universities, shopping centers, and restaurants. Its location makes it a strategic base to explore San José and plan your journey through Costa Rica.

Guest favorite
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.
Apartment in Curridabat
4.95 out of 5 average rating, 140 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.

Popular amenities for Guadalupe rentals with a pool

When is the best time to visit Guadalupe?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$11,867 GYDG$11,867 GYDG$12,075 GYDG$10,826 GYDG$9,993 GYDG$10,618 GYDG$10,201 GYDG$10,410 GYDG$10,201 GYDG$11,034 GYDG$11,659 GYDG$12,908 GYD
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