
Vacation rentals with a pool in Guadalupe
Find and book unique homes with a pool on Airbnb
Quick stats about vacation rentals with a pool in Guadalupe

Total vacation rentals
Explore 80 vacation rentals in Guadalupe

Nightly prices starting at
Guadalupe vacation rentals start at G$6,249 GYD per night before taxes and fees

Verified guest reviews
Over 2,670 verified reviews to help you choose

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

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
60 properties have a dedicated workspace

Wi-Fi availability
80 of Guadalupe vacation 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.

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.

Industrial 2BR perfect location w/AC + sunset view
Take a morning stroll in the park before heading back to your centrally-located, industrial 2 br apartment that will welcome you with high-speed wifi, top-of-the-line kitchen appliances, amazing decor, comfortable beds, and sunset views from a 12th floor overlooking the city. Not only will you have access to unparalleled amenities like a semi-Olympic pool, saunas, gym, and co-working space, you will be a walking distance from the best restaurants, coffee shops, and grocery stores in town.

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.

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.

City view, A/C near the airport, 1903
It is an apartment with an excellent distribution and a modern and contemporary aspect, located near the La Sabana Metropolitan Park, an area with excellent restaurants, entertainment venues, and very close to shopping centers, Juan Santamaría airport, etc; It is on the 19th floor, with a view to the east, the mountains and the city steal the show at all hours of the day, without a doubt the sunset and night are the favorites for their colors and lights.

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.

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.

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 .

Breathtaking Mountain View Apt.
Vive la experiencia de hospedarte en un apartamento único en el piso 29 de torre Secrt Sabana , con una vista panorámica impresionante de las montañas de San José , a solamente 200 metros del Parque Metropolitano de la Sabana (mejor ubicación en San José) disfrutarás de sus más de 20 amenidades, te vas a cautivar por los detalles decorativos que verás en cada rincón. ***Aeropuerto Juan Santamaria a solamente 10 millas***

BeST RANkED SuPERHOST * 18th Floor * KInG sIZE BeD
Studio Apartment on the 18th floor. Peaceful and centrally-located place. KING SIZE BED GREAT VIEW of the mountains. The apartment is close to supermarkets, shopping malls, restaurants, and cafeterias. Located in a beautiful and fancy neighborhood. Close to bus stops and San Jose Metro-Area Fast Uber rides. *** This building is smoke free, therefore is not allowed to smoke in any location nor in the apartment ***
Popular amenities for Guadalupe rentals with a pool
House rentals with a pool

Centrally located apartment in the east of San José

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

Casa Gaudi🦚Near SJO🦚Private Pool & King BD

Villa Bugambilia: Large colonial villa with pool.

Casa Delios, Luxury Near the Airport, Private Pool

Beautiful house with pool in Heredia Centro

8p Luxury Townhouse-Concierge & Cleaning

Casa Escobar
Condo rentals with a pool

Studio with view, balcony and free parking · URBN

Fully equipped apartment in Nunciatura

La Madriguera Serena/ SECRT Sabana.

Amazing Apart SECRT Sabana/ AC+Gym+Swimming pool

Urbn Escalante Downtown View

Urban Jewel on the 30th floor; SECRT

Alicia's Garden Apartment at Secrt

Charming Apartment w A/C Near to the Int. Airport
Other vacation rentals with a pool

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

Cozy studio, best gastronomic area Escalante

Tropical-inspired urban retreat on the 22nd floor

Stylish Studio with Sky Bar & City Views

SECRT Escalante · 19th Floor · View + Parking

Ifreses Apartment: clean/balcony/WiFi/desk

Exclusive Apartment in Downtown Costa Rica

Amazing Contemporary Penthouse in San José Tower
When is the best time to visit Guadalupe?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$11,872 GYD | G$11,872 GYD | G$12,081 GYD | G$10,831 GYD | G$9,998 GYD | G$10,623 GYD | G$10,206 GYD | G$10,414 GYD | G$10,206 GYD | G$11,039 GYD | G$11,664 GYD | G$12,914 GYD |
| 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 |
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- Rentals with pools San Jose Province
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- 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
- Parque Nacional Los Quetzales
- Parque Nacional Braulio Carrillo
- University of Costa Rica
- Turrialba Volcano National Park
- Playa Jacó
- Carara National Park
- Multiplaza Escazú
- El Miro
- Children’s Museum
- Hacienda Alsacia Starbucks Coffee Farm
- La Cruz del Monte de la Cruz
- Parque Central
- Britt Coffee Tour





