
Holiday 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.

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👍

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

Joya Urbana en el piso 30; SECRT
Sumérgete en la magia de este apartamento en el piso 30 de SECRT Sabana, inspirado en *Alicia en el País de las Maravillas*. Diseñado con decoración cálida de plantas y luces, cuenta con un dormitorio privado, clóset, y espacio de trabajo. Cocina totalmente equipada con básicos incluidos, y baño con amenidades. Disfruta vistas espectaculares y compra snacks, bebidas y artículos personales disponibles en el apartamento. Todo lo que necesitas para una estancia única y cómoda. Parqueo $15 adicional

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.

Urban Modern Apartment - Roof Top Pool
Centrally located near La Sabana Metropolitan Park, my apartment offers a perfect blend of relaxation and functionality. The space is designed for comfort and it’s ideal for virtual work, with a fully equipped kitchen for energizing breakfasts or intimate dinners. Enjoy restful sleep, complete privacy, and the convenience of a full and half bathroom. The unique contemporary ambiance enhances your stay. Additionally, the apartment offers free parking within the building for added convenience.

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.

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!

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.

Acogedor loft con vista panorámica de San José
The loft is equipped so you can rest all day or work from here. You have a beautiful view of San José. It has a kitchen, comfortable bed, a comfortable bathroom, and all the amenities. But if you decide to go out for a walk, you will have the most relevant gastronomic area of San José, graffiti, restaurants, parks so you can have a coffee in a safe area full of the Costa Rican capital spirit. Work or rest, in a central and accessible area.

Gorgeous sunsets at charming apartment in downtown
We welcome you to your new and luxurious apartment in the center of the city, located in one of the most iconic residential buildings in the country, with a variety of amenities and just a 5-minute walk away from the most famous gastronomic area of San José. The neighborhood is safe, and has different areas according to your preference (whether it's a night out, or a quiet afternoon in the park). A/C, WiFi 500 mbps, and parking included.

Couples Focused Magnificent Studio Apartment
FREE early check-in upon request!! Escape stress in our stunning 23rd-floor adult-only apartment, offering an erotic touch . Enjoy 24/7 self-check-in, secure parking, and a rooftop with a heated pool for sunset relaxation. Fully equipped kitchen and numerous restaurants, coffee shops and markets nearby. Perfect for couples local looking for a quick get away or the best option for foreigners to start or end their Costa Rica trip .

Upscale apartment at URBN Escalante
Luxurious 26th-floor condo in the heart of Barrio Escalante, San José, Costa Rica! Fully furnished with 2 bedrooms, 2 bathrooms, a modern kitchen, washer/dryer, and HD Smart TVs. Enjoy URBN Escalante’s 24/7 lobby, heated pool, gym, and proximity to top restaurants, cafes, and nightlife. Perfect for travelers or remote workers seeking comfort and convenience in this vibrant urban hub. Stays of 6+ days allow guest visitors.
Popular amenities for Guadalupe rentals with a pool
House rentals with a pool

Casa Relax en Condo Costa Rica

4BR Casa Peces Santa Ana, Indoor Pool & Sauna!

Beautiful house with private pool

Casa Gaudi🦚Near SJO🦚Private Pool & King BD

Hidden Paradise Resort, 10 min from SJO Airport

Luxury Townhouse (8p max)-Pool & Fitness-Escazu

City Scapes Home2BR 2131ft2 Amenities Security24X7

Casa Escobar
Condo rentals with a pool

Concrete Jungle Experience 25th Floor Secrt Sabana

Fully equipped apartment in Nunciatura

AC and King Bed - Full Equipped Apartment

Apartamento Flofy - Piscina - Parqueo - Seguridad

Urbn Escalante Downtown View

Industrial 2BR perfect location w/AC + sunset view

The Gourmet Terrace & Coffee View w/AC

5 min from Airport | Transfer ($) | Pool | Gym
Other holiday rentals with a pool

Sunsets & Style — Modern Stay in Trendy Escalante

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Amazing Penthouse in San José

Aura-Cozy Apt Near Airport&Sabana-AC-Free Parking
Quick stats about holiday rentals with a pool in Guadalupe

Total holiday rentals
Explore 70 holiday rentals in Guadalupe

Nightly prices starting at
Guadalupe holiday rentals start at $30 AUD per night before taxes and fees

Verified guest reviews
Over 830 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
50 properties have a dedicated workspace

Wi-Fi availability
60 of Guadalupe holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi and Pool across Guadalupe rentals

4.8 Average rating
Guadalupe stays are highly rated by guests—averaging 4.8 out of 5!
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- La Sabana Park
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- Manuel Antonio National Park
- Poás Volcano National Park
- Parque Diversiones
- Chirripó National Park
- Marina Pez Vela
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- Playa Boca Barranca
- Juan Castro Blanco National Park
- Irazú Volcano National Park
- Carara National Park
- La Iguana Golf Course
- La Cruz del Monte de la Cruz
- La Cangreja National Park
- Turrialba Volcano National Park
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- Playa Gemelas
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