
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.

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!

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.

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.

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.

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 .

URBN-Escalante apartment with parking
Brand new studio with the best location in town. Comfortable and cozy studio apartment with fully furnished kitchen, dining table, works pace, queen bed, one full bathroom, living area, indoor parking and balcony. The apartment is in a brand new 29 story building, with many social areas and amenities: gym, pool, yoga studio, laundry area, library and the lounges and work spaces with literally the best views of the city.

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.

URBN Barrio Escalante Fully Equipped 20th Floor
Exotic, Unique, Hip, Cool, and Relaxing High Rise 5 stars Resort Style Condo centrally located in the Gastronomic district of San Jose Costa Rica. the Resort Style Condo has it all! Heater Pool, full Size Gym, Co-working, 29th Story skyline viewing deck, Private Meeting Rooms, Theater Room, and more.
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

Casa Gaudi🦚Near SJO🦚Private Pool & King BD

Casa Delios, Luxury Near the Airport, Private Pool

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

3BR Home w/ AC & high speed internet near airport

Playa Bejuco Condominium 243
Apartment rentals with a pool

Concrete Jungle Experience 25th Floor Secrt Sabana

Luxury Apartment, San José, La Sabana, Del Lago

30 mins SJO | Pool View | Premium Appt | Parking

Cosmopolitan SkyView Apartment 2BR

Industrial 2BR perfect location w/AC + sunset view

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

Urbn City View Barrio Escalante 17th Floor with A/C

Top Pick in La Sabana: Spotless & Comfy with A/C
Other holiday rentals with a pool

Bo Escalante apt/rooftop pool/gym/Views/parking

Airport Apt/floor16 AC+Paking+Rooftop views +Tours

Stylish Studio with Sky Bar & City Views

SECRT Escalante · 19th Floor · View + Parking

Cityscape iFreses, 20th floor! AC, TV and Pool

URBN Industrial Style Apart. A/C Full+Parking FREE

NucleoSab IvoryApt-NearSJairport-FreeIndoorParking

Apartment with excellent location. AC/wifi
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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- Apartment rentals Guadalupe
- Rentals with pools San Jose Province
- Rentals with pools Costa Rica
- Jaco Beach
- Dominical Beach
- La Sabana Park
- National Stadium of Costa Rica
- Parque Nacional Manuel Antonio
- Poás Volcano National Park
- Parque Diversiones
- Chirripo National Park
- Parque Nacional Braulio Carrillo
- Marina Pez Vela
- Carara National Park
- Parque Nacional Los Quetzales
- Irazú Volcano National Park
- La Cruz del Monte de la Cruz
- Parque Viva
- Turrialba Volcano National Park
- University of Costa Rica
- Nauyaca Waterfalls
- Children’s Museum
- Catarata del Toro
- Pre-Columbian Gold Museum
- San Jose Central Market
- Playa Jacó
- Britt Coffee Tour




