
Holiday rentals with a pool in Guadalupe
Find and book unique homes with a pool on Airbnb
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 $50 NZD per night before taxes and fees

Verified guest reviews
Over 2,670 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
60 properties have a dedicated workspace

Wi-Fi availability
80 of Guadalupe holiday 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!
Top-rated rentals with a pool in Guadalupe
Guests agree: These homes with a pool are highly rated for location, cleanliness and more.

Loft with a balcony, panoramic view, and private parking
We offer you an apartment on the 18th floor, with a panoramic view and cool breeze. This modern loft combines style and comfort with an integrated balcony, blackout curtains for added comfort, wifi, and private parking. On the 25th floor we have an infinity pool, iworking area and more. We are located in a safe and central area of Curridabat, where you will have everything at your fingertips. As a Top 10% Superhost in Costa Rica, I guarantee fast and dedicated attention to make your stay memorable.

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.

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.

Tastefully Furnished Penthouse + Rooftop Pool
Lets chat for a FREE early check in 24/7 security extremely safe building and neighborhood Get up in the morning in this magnificent penthouse with the most magnificent view of Irazú and Barva Volcano, enjoying a cup of the most amazing costarican gourmet coffee. Get on to the amenities to enjoy a relaxing morning/sunset dip at the pool and workout in our fully equipped gym or grab a meal in one of the more than 80 restaurants in a 5 block radius following a nice pool table session

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

*NEW* Luxury Condo | Stunning Views
Luxury condo with stunning views of the mountains & city. Just footsteps away from trendy coffee shops, bustling bars & over 50 restaurants. Located just 25 minutes from the airport. The building has 24/7 security, swimming pool & gym. This modern & professionally decorated condo offers a fully equipped kitchen, Full Size bed + a Queen pullout sofa bed. High Speed Wifi, AC & Smart TV’s in the bedroom & living room. This comfortable & cozy space truly feels like a home away from home.

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.

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.

Ifreses Apartment: clean/balcony/WiFi/desk
The space is very comfortable as it is equipped with kitchen utensils, a work table, Wi-Fi, TV, air conditioning, an individual armchair, a two-person armchair, shelves, closets, etc. that make it very cozy. It also has a balcony with sliding doors that allows you to enjoy beautiful views of San José and the mountains, incredible sunsets and fresh air. Most of the ratings highlight the cleanliness of the space, something we particularly care about offering.

Apartment in Escalante Olive Loft 14th
A modern and elegant studio on the 14th floor, with an amazing sunset view. Located in the heart of Barrio Escalante, close to bars and excellent restaurants with a wide variety of cuisine, opposite one of the 100 best cafés in the world. Perfect for couples, solo travelers or digital nomads looking for comfort in a safe and walkable location. Escalante is the cultural and gastronomic epicenter of San José, with active local life at any time of the day.

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.
Popular amenities for Guadalupe rentals with a pool
House rentals with a pool

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

Casa Delios, Luxury Near the Airport, Private Pool

Luxury in your Home, private Pool and Jacuzzi.

Casa Gaudi🦚Near SJO🦚Private Pool & King BD

Heated Infinity Pool Villa, 6BR, 25 Min SJO

Vacation-Resort House 15 min from Arpt

Buena Vista Home

Casa Escobar
Condo rentals with a pool

Studio with a view, balcony and free parking · URBN

Modern apartment at gastronomic epicenter

Modern Loft in San José with Rooftop Pool

Industrial 2BR perfect location w/AC + sunset view

City view, A/C near the airport, 1903

The Madriguera Serena/ SECRT Sabana.

Beautiful top floor apt. panoramic view Sabana a/c

Scenic, 3BR Condo | Pool, Gym & 24/7 Security
Other holiday rentals with a pool

Hideout in downtown San Jose-Sergio

Apt BoEscalante/Free Parking compact car/City view

Best location, cozy Apartment!

SECRT Sabana 31st | A/C, Parking & View

Escazú Treetop Casita w/ Panoramic Luxury Views

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

Urban Modern Apartment - Roof Top Pool

Apartment with excellent location. AC/wifi
When is the best time to visit Guadalupe?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $95 NZD | $95 NZD | $97 NZD | $97 NZD | $94 NZD | $90 NZD | $82 NZD | $84 NZD | $82 NZD | $89 NZD | $94 NZD | $104 NZD |
| 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 |
Destinations to explore
- Jaco Beach
- Dominical Beach
- Playa Blanca
- Parque Nacional Manuel Antonio
- La Sabana Park
- National Stadium of Costa Rica
- Parque Viva
- Parque Diversiones
- Marina Pez Vela
- Poás Volcano National Park
- Chirripo National Park
- University of Costa Rica
- Parque Nacional Braulio Carrillo
- Parque Nacional Los Quetzales
- Multiplaza Escazú
- Playa Jacó
- Turrialba Volcano National Park
- Carara National Park
- El Miro
- Children’s Museum
- Hacienda Alsacia Starbucks Coffee Farm
- City Mall Alajuela
- Basilica De Nuestra Señora De Los Ángeles
- Britt Coffee Tour





