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Vacation rentals with a pool in Guadalupe

Find and book unique homes with a pool on Airbnb

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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Superhost
A modern bedroom features a spacious bed with fresh linens, positioned against a blue wall. A small nightstand is located on one side. A piece of wall art adds a decorative touch, while large windows provide views of the city and mountains.
Apartment in California
4.87 out of 5 average rating, 353 reviews

Balcony Sunset View 21st Floor Apartment

Located 21st floor of the stylish URBN Escalante building in the heart of San José, this modern one bedroom apartment has all the amenities for a pleasurable stay. Feel free to make use of the lobby with 24/7 concierge, heated pool, lounge area, co-working spaces, gym, yoga room, cinema, library, BBQ area and playground. Internet is available at all common areas as well as high-speed internet connection -100Mbps- in the apartment. 5-10 minute walk to Pubs, Restaurants and Supermarkets. Netflix👍

Top guest favorite
An outdoor seating area is framed by a modern structure, overlooking a pool surrounded by lounge chairs. Umbrellas provide shade, and greenery is visible in the background, enhancing the relaxing environment.
Apartment in Mantica
4.85 out of 5 average rating, 295 reviews

15th Floor Apt / Amazing Views • 20 min to Airport

Experience San José from a modern apartment with panoramic city views in the exclusive Núcleo Sabana complex. Fully equipped with Wi-Fi 5G, Smart TV, full kitchen, and private parking. Enjoy premium amenities including a pool, gym, sauna, lap lanes, multi-sport court, karaoke room, and beautiful green areas. Located steps from La Sabana Park, and the National Stadium and any restaurants. Perfect for business travelers, couples, or anyone seeking comfort and style in Costa Rica’s lively capital.

Top guest favorite
Apartment in Curridabat
4.91 out of 5 average rating, 213 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.

Top guest favorite
A modern kitchen area features sleek cabinetry and stainless steel appliances, complemented by a dining space with stylish chairs. Large windows allow natural light to fill the room, providing a view of the greenery outside, creating a bright and open atmosphere.
Condo in Mantica
4.95 out of 5 average rating, 154 reviews

Top Pick in La Sabana: Spotless & Comfy with A/C

Luxury apartment with A/C, cozy, and perfectly located in the heart of the city. This fully equipped space, with modern and elegant decoration, offers you the freedom to live safely and comfortably while exploring everything the city has to offer. Close to tourist attractions, banks, supermarkets, and restaurants. (The condominium has 8 restaurants within the facilities) The International Airport (SJO) is 20 minutes away, La Sabana Park and the new National Stadium are 3 min away in San Jose.

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
4.9 out of 5 average rating, 376 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.

Superhost
Apartment in Mata Redonda
4.86 out of 5 average rating, 609 reviews

Family|Business Flat w/ 270° Mountain+City Skyline

Great Pent House in one of the most Upscale location and Luxury 180° Mountain + City View places in San Jose, La Sabana. Lots of amenities, including Gym, Yoga, pool deck, Sauna & Steam Room, etc. Private 2x parking lots with private entrance. Security Surveillance. Walking distance to La Sabana Park and lots of access to anywhere in the Country. 18 mins to Juan Santamaria Int. Airport. 10 minutes to Multiplaza Mall in Escazu minutes to Barrio Escalante, San Pedro. 1.5 hrs to Jaco Beach.

Top 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
4.96 out of 5 average rating, 112 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

Superhost
Apartment in Escalante
4.83 out of 5 average rating, 174 reviews

Stylish unit and great location in downtown.

Apt ubicado en los alrededores de Barrio Escalante, un hermoso lugar compuesto de casas antiguas, tiendas de diseño y restaurantes con diversas propuestas culinarias. Esto lo hizo digno de obtener el premio a "destino líder de México y Centroamérica a visitar 2019" en World Travel Awards. Es uno de los epicentros gastronómicos y culturales más importantes en San José, donde podrás escoger desde un hermoso lugar para tomar café hasta un distinguido bar para estar con tu pareja.

Guest favorite
A bright living area features a comfortable sofa, a small dining table, and large glass doors that open to a lush garden. Natural light filters in through sheer curtains, accentuating the greenery outside. Houseplants are arranged decoratively within the space.
Condo in Alajuela
4.93 out of 5 average rating, 206 reviews

5 min from Airport | Transfer ($) | Pool | Gym

The condo has 2 bedrooms, a living room, dining room, kitchen, 2 bathrooms, and is located 2 miles from SJO Airport. Additionally, you’ll be just 2 minutes away from City Mall and Walmart. • Airport Transfer Available (at an additional cost) • 24/7 security • Pool • Gym • Coworking space • High-speed internet • Clubhouse • Parking You'll find in the apartment coffee, a fully equipped kitchen, AC units (in the bedrooms and living room), TV, king-size bed, and full-size bed.

Guest favorite
A modern living area features a comfortable gray sofa positioned opposite a large television. A small coffee table sits in front, accompanied by a decorative plant. Panoramic windows offer a view of the city lights in the distance, enhancing the room's spacious layout.
Loft in Curridabat
4.98 out of 5 average rating, 102 reviews

Apartment with excellent location. AC/wifi

Your 23rd-floor retreat with spectacular views! Wake up every morning in a cozy apartment located on the 23rd floor, where the sweeping views of the city from the balcony provide the perfect backdrop for your morning coffee or a sunset drink. Its location is perfect: just steps away are restaurants serving a variety of cuisines, a shopping center with a supermarket, pharmacy, and hospital, all within walking distance, making your stay convenient and worry-free.

Guest favorite
A modern bedroom features a plush bed with decorative pillows, complemented by stylish bedside lamps. A wall-mounted television is positioned opposite the bed, and large windows provide expansive views of the cityscape. Warm wood paneling adds a touch of elegance to the space.
Apartment in Curridabat
4.87 out of 5 average rating, 126 reviews

Insta-worthy Apartment in a Beautiful Neighborhood

Welcome to your stylish and centrally located home away from home in San José, Costa Rica! Your custom apartment boasts a fully equipped kitchen. Relax in the comfort of the queen bed and enjoy the smart TV and FAST (200 mbps) internet. Amenities include a rooftop pool, gym, coworking area and 24/7 security for your peace of mind. Experience the best of the city with easy access to all the sights and sounds that San Jose has to offer.

Guest favorite
A dining setup is visible in the foreground with two white plates, utensils, and wine glasses placed on a textured gray surface. The background features a large window showcasing an expansive view of the city with greenery and mountainous scenery. A cozy seating area with a gray couch and a wooden table is also present.
Loft in Curridabat
4.91 out of 5 average rating, 286 reviews

Elegant loft in the heart of the city with pool

Welcome to your oasis of tranquility! Enjoy this elegant and centrally located accommodation with stunning mountain views, perfect for relaxing and unwinding. This space is designed to give you maximum comfort, with all the necessary amenities to make your stay unforgettable. Its location is ideal, as it places you close to restaurants, shops, and local attractions. Come and enjoy a unique experience in this charming retreat!

Popular amenities for Guadalupe rentals with a pool

Quick stats about vacation rentals with a pool in Guadalupe

  • Total vacation rentals

    Explore 70 vacation rentals in Guadalupe

  • Nightly prices starting at

    Guadalupe vacation rentals start at ﺩ.ﺇ73 per night before taxes and fees

  • Verified guest reviews

    Over 1,590 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

    70 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!