
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.

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

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.

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!

Cálido estudio en Barrio Escalante
Vive la experiencia de Barrio Escalante, la zona más vibrante y gastronómica de la ciudad. Este apartamento combina elegancia y confort, ofreciéndote un espacio ideal para descansar después de explorar restaurantes, cafeterías y bares únicos, todos a pocos pasos de tu puerta. Todo en un piso 13 con una hermosa vista con los mejores atardeceres y sin dejar de lado la posibilidad de tener acceso autopistas que conectan con otros destinos turísticos cercanos, como volcanes, montañas y playas.

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.

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

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.

Best location, cozy Apartment!
Beautiful condo in perfectly located apartment building. The whole place has a modern feel to it without losing a touch of home. The unit is composed of one bedroom with an ensuite bathroom, living room and deck to relax and enjoy the views, as well as a modern kitchen and laundry machine. This cozy and modern apartment is close to all the best restaurants and night life in San Jose, as well as museums and downtown. Major public transportation is right outside the door.

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.

Elegante loft en el corazón de la ciudad c/piscina
¡Bienvenido a tu oasis de tranquilidad! Disfruta de este elegante y céntrico alojamiento con impresionantes vistas a las montañas, perfecto para relajarte y desconectar. Este espacio está diseñado para brindarte la máxima comodidad, con todos los servicios necesarios para que tu estadía sea inolvidable. Su ubicación es ideal, ya que te sitúa cerca de restaurantes, tiendas y atracciones locales. ¡Ven y vive una experiencia única en este encantador refugio!

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 .

Chic Bohemian Loft
Discover our Bohemian Sky Retreat on the 18th floor, a blend of bohemian elegance and comfort with stunning city views. Enjoy vibrant decor, a plush living area with a smart TV, and a fully equipped kitchen. The serene bedroom promises a restful night beside mesmerizing skyline views. Steps from cafes, dining, and attractions, this urban oasis offers an unforgettable city experience.
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!

Villa Jardín Escondido

Large home, pool, and great view

Casa Gaudi🦚Near SJO🦚Private Pool & King BD

Apartamento El Dorado Cerca del Aeropuerto SJO

Condominio Playa Bejuco 243

Authentic Costa Rican Luxurious Tropical Home
Apartment rentals with a pool

Concrete Jungle Experience 25th Floor Secrt Sabana

Enjoy Barrio Escalante-Sjo

9.9 mill SJO | Pool View | Cozy Loft | Parking

Urbn Escalante Downtown View

Industrial 2BR perfect location w/AC + sunset view

Skyline Loft 22nd Fl • Views + Pool + Gym + AC

Charming Apartment w A/C Near to the Int. Airport

Modern apartment at gastronomic epicenter
Other holiday rentals with a pool

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

Apartamento en Escalante Olive Loft 14th

Nebulae - Water Cube Suite & YogaDeck

Modern Luxury Condo in La Sabana Pool, Gym & View

SECRT Escalante · 19th Floor · View + Parking

Modern 12th Floor | Views + Pool & Gym

URBN 2601, Amazing View Loft, 26 floor

Bohemian Bliss in exclusive area w rooftop+Pool
When is the best time to visit Guadalupe?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £42 | £42 | £43 | £39 | £36 | £38 | £36 | £37 | £36 | £39 | £42 | £46 |
| Avg. temp | 22°C | 23°C | 24°C | 24°C | 24°C | 24°C | 24°C | 23°C | 23°C | 23°C | 23°C | 23°C |
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 £15 per night before taxes and fees

Verified guest reviews
Over 2,240 verified reviews to help you choose

Family-friendly holiday rentals
10 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 20 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!
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- Rentals with pools San Jose Province
- Rentals with pools Costa Rica
- Jaco Beach
- Dominical Beach
- La Sabana Park
- Playa Blanca
- National Stadium of Costa Rica
- Parque Nacional Manuel Antonio
- Parque Viva
- Parque Diversiones
- Poás Volcano National Park
- Marina Pez Vela
- Chirripo National Park
- Parque Nacional Braulio Carrillo
- Parque Nacional Los Quetzales
- Carara National Park
- Turrialba Volcano National Park
- University of Costa Rica
- Playa Jacó
- La Cruz del Monte de la Cruz
- El Miro
- Multiplaza Escazú
- Children’s Museum
- City Mall Alajuela
- Nauyaca Waterfalls
- Parque Central





