
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$4,183 GYD per night before taxes and fees

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

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

Pet-friendly vacation rentals
Find 20 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.

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

Beautiful loft pool, gym and excellent location
Disfrute de una experiencia elegante en este lugar céntrico de San José, a poca distancia de los lugares más modernos, históricos y turísticos. Disfruta tranquilamente de un apartamento a estrenar con todo lo necesario para tu estancia. Tendrás un supermercado frente al edificio, pero también bares y restaurantes en Barrio Escalante. Acceso a excelentes amenidades: Gimnasio, 2 albercas, área de BBQ, firepit al aire libre, roof garden para disfrutar de vistas únicas de San José.

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.

Studio with view, balcony and free parking · URBN
Stay on the 12th floor of URBN Escalante, San José’s iconic tower, with city views from your private balcony. Enjoy a queen bed, a fully equipped kitchen, fast Wi-Fi, workspace, and FREE indoor parking. Located in the heart of Barrio Escalante, with 70+ restaurants, cafés, and bars within a 5-minute walk. Building amenities include a gym, heated pool, laundry room, coworking space, library, yoga room, cinema, and rooftop views. Check-in at the lobby is available 24/7

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.

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.

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.

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

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

Green Escape with Style

Casa Gaudi🦚Near SJO🦚Private Pool & King BD

Villa Bugambilia: Large colonial villa with pool.

Casa Delios, Luxury Near the Airport, Private Pool

8p Luxury Townhouse-Concierge & Cleaning

Playa Bejuco Condominium 243

Tropical Nest | Modern Gated Home w/ Pool Near SJO
Condo rentals with a pool

Luxury Apartment, San José, La Sabana, Del Lago

9.9 mill SJO | Pool View | Cozy Loft | Parking

Urban Jewel on the 30th floor; SECRT

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

The Gourmet Terrace & Coffee View w/AC

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

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

Casa Verde · 7 min from SJO · Pool+Gym · Fast WiFi
Other vacation rentals with a pool

Sunsets & Style — Modern Stay in Trendy Escalante

Breathtaking Mountain View Apt.

Urban Modern Apartment - Roof Top Pool

SECRT Escalante · 19th Floor · View + Parking

Couples Focused Magnificent Studio Apartment

Exclusive Apartment in Downtown Costa Rica

Brand new cosy loft. 3 min from SJO airport

Hideout in downtown San Jose-Sergio
When is the best time to visit Guadalupe?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$11,922 GYD | G$11,922 GYD | G$12,131 GYD | G$10,876 GYD | G$10,040 GYD | G$10,667 GYD | G$10,249 GYD | G$10,458 GYD | G$10,249 GYD | G$11,085 GYD | G$11,713 GYD | G$12,968 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
- Rentals with pools Costa Rica
- 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
- Chirripo National Park
- Poás Volcano National Park
- Parque Nacional Braulio Carrillo
- Parque Nacional Los Quetzales
- Playa Jacó
- Carara National Park
- Turrialba Volcano National Park
- University of Costa Rica
- Multiplaza Escazú
- El Miro
- Parque Central
- Hacienda Alsacia Starbucks Coffee Farm
- Children’s Museum
- La Cruz del Monte de la Cruz
- Britt Coffee Tour





