
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 $42 AUD 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.

Rooftop Pool - AC - Gym - In Unit W/D - iFreses 6c
New Studio Apartment in a Brand New High Rise Building. Great location, Walk Score of 90 ("Walker's Paradise Daily errands do not require a car.") Queen size bed, couch, 50 inch smart TV. The building has every amenity you could wish Rooftop pool, Movie Room, iWork area, coWork Area, Game Room, Gym, Landry Room, Art Room and many many more. Very close to Super Market (Automercado), Coffee Shops. Just 11 minute bus ride to Downtown San José Or Just $3 Uber ride to Downtown San José

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

SECRT Sabana 31st | A/C, Parking & View
Modern studio on the 31st floor of SECRT Sabana with an incredible view of the city and mountains. Enjoy unique sunrises and sunsets from the top level. The space includes AC, a Queen bed, equipped kitchen, smart TV, free parking in the building, and a peaceful environment to relax or work with total privacy. Located near restaurants, supermarkets, La Sabana, and with great access to transportation. Ideal for business trips or couple getaways. We look forward to hosting you!

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.

Beautiful loft pool, gym, equipped in Escalante
Enjoy a stylish experience at this centrally-located, fully-equipped place in the best area, Barrio Escalante 24/7 security, 2 swimming pools, gym, BBQ area, cinema room, rooftop with beautiful views of San José. Brand new building with modern architecture, close to supermarkets, shopping mall, bus and train stops. You can walk to the best historical and tourist spots as well as trendy restaurants and bars in Escalante and La California

10th floor Apartment w/ Sky-Level Pool in San José
Private, comfortable, and strategically located in the heart of Curridabat. This studio on the 10th floor of the iFreses building is perfect for couples, students, or travelers seeking a quiet and functional space. It offers all the essentials for a pleasant stay and is surrounded by universities, shopping centers, and restaurants. Its location makes it a strategic base to explore San José and plan your journey through Costa Rica.
Popular amenities for Guadalupe rentals with a pool
House rentals with a pool

Smart loft in the heart of the city, A/C and Wi-Fi

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
Condo rentals with a pool

Studio with a view, balcony and free parking · URBN

Modern apartment at gastronomic epicenter

The Studio Torre Los Yoses!

City view, A/C near the airport, 1903

Industrial 2BR perfect location w/AC + sunset view

The Madriguera Serena/ SECRT Sabana.

Oasis Escalante Queen Bed & Sofa Bed w/ A/C

Beautiful top floor apt. panoramic view Sabana a/c
Other holiday rentals with a pool

Hideout in downtown San Jose-Sergio

Apartment in Escalante Olive Loft 14th

Whimsical 27th Floor Apt, King Bed, AC, Parking

Apt BoEscalante/Free Parking compact car/City view

Best location, cozy Apartment!

Escazú Treetop Casita w/ Panoramic Luxury Views

BeST RANkED SuPERHOST * 18th Floor * KInG sIZE BeD

Cheerful private 4-Bedroom Villa. Heated pool A/C
When is the best time to visit Guadalupe?
| Month | Jan | Feb | Mar | Apr | May | June | July | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $80 AUD | $80 AUD | $81 AUD | $81 AUD | $78 AUD | $75 AUD | $68 AUD | $70 AUD | $68 AUD | $74 AUD | $78 AUD | $86 AUD |
| 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
- Multiplaza Curridabat





