
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.

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

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.

Beautiful loft pool, gym and excellent location
Disfrute de una experiencia elegante en este lugar céntrico de San José, a poca distancia de los lugares más modernos, históricos y turísticos. Disfruta tranquilamente de un apartamento a estrenar con todo lo necesario para tu estancia. Tendrás un supermercado frente al edificio, pero también bares y restaurantes en Barrio Escalante. Acceso a excelentes amenidades: Gimnasio, 2 albercas, área de BBQ, firepit al aire libre, sala de cine, roof garden para disfrutar de vistas únicas de San José.

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.

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.

★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!

Stylish 1 BR w A/C, Private Terrace
Enjoy a stylish experience at this centrally-located condominium, less than half a mile from downtown and in the heart of the trendy gastronomic Barrio Escalante with countless options of restaurants and bars. Whether working remotely, visiting friends, health tourism or on holiday, with speedy internet, fully equipped kitchen and bathroom, a very calm and serene terrace, gym and pool, coworking, lounge and bar, you will feel right at home with the touch of the latin culture.

Urban Jewel on the 30th Floor; SECRT
Immerse yourself in the magic of this apartment on the 30th floor of SECRT Sabana, inspired by *Alice in the Wonderland*. Designed with warm floor and light decor, it has a private bedroom, closet, and working space. Fully equipped kitchen with essentials included, and bathroom with amenities. Enjoy spectacular views and buy snacks, drinks, and personal items available in the apartment. All you need for a unique and comfortable stay. Parking $15 additional

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 .

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!

New Bohemian Studio Best Views
SECRT Tower in Sabana is the absolute best tower in San Jose very close to Parque La Sabana (400 mtrs / 0.3miles). 20 min from Airport. Great, safe location. Very accesible, walking distance to restaurants, stores, pubs, supermarket, gas stations, etc. Apt is fully equipped. Free parking. Hot water. Coffee is on the house! Both living room and bedroom have TVs, with Netflix and Disney+ included and wifi speeds of 200MB
Popular amenities for Guadalupe rentals with a pool
House rentals with a pool

New 3BR Condo | by SJO Airport & Convention Center

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

Large home, pool, and great view

Beautiful house with private pool

Casa Gaudi🦚Near SJO🦚Private Pool & King BD

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

Luxury Apartment, San José, La Sabana, Del Lago

Modern/comfort great views 2Bdr 2Bath Escalante

30 mins SJO | Pool View | Premium Appt | Parking

Flofy Apartment - Pool - Parking - Security

Luxury SkyView Apartment 2BR

Comfortable apartment in upscale neighborhood

Industrial 2BR perfect location w/AC + sunset view
Other vacation rentals with a pool

Apartment in EscalanteOlive Loft 14th

Urban Vista iFreses, 2nd floor! AC, TV and Pool

URBAN LUX APT w/Prime Location•Fast WIFI•Pool•GYM

Modern Nook Bo Escalante

Retro Arcade Escalante

Amazing Penthouse in San José

Apartment with excellent location. AC/wifi

Luxury High-Rise | 16th Floor | La Sabana-San José
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 $28 CAD per night before taxes and fees

Verified guest reviews
Over 830 verified reviews to help you choose

Family-friendly vacation rentals
10 properties offer extra space and kid-friendly amenities

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
50 properties have a dedicated workspace

Wifi availability
60 of Guadalupe vacation rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi, 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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