
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$6,246 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 at 24th floor - SJO view
Exclusivo apartamento en el Condominio iFreses piso 24, cerca del centro de San José, rodeado de tiendas, restaurantes, bares, barrios gastronómicos y más. Estacionamiento disponible por una tarifa adicional, no se permiten carros tipo pickup por tamaño/ Exclusive apartment at Condominio iFreses on the 24th floor, in the center of the city, surrounded by shops, restaurants, bars, gastronomic neighborhoods and much more. Parking available with an additional fee, no pickups are allow due to size.

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.

Rooftop Pool - AC - Gym - In Unit W/D - iFreses 7b
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 ammenity 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

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

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

Urban Calm Retreat 9th
Located in San Jose’s trendiest neighborhood, with all the amenities you need for a nourishing stay in the city. This 24th-floor apartment has a balcony overlooking the city with incredible sunset views. Designed with the perfect balance of comfortable elements, local art, and vibrant plants, it has everything you need to rest and relax. This is the ideal base for exploring the neighborhood of Barrio Escalante, with dozens of independent restaurants, cafes, and shops just steps away.

★Luxurious Apt★ | Panoramic View, Pool, Gym + Pkg
Relax at our luxury apt at a prime location from which you can easily experience all of San Jose. Marvel at the mesmerizing views from the 23rd floor of a modern, industrially designed building, in the heart of Barrio Escalante. Perfect blend of luxury comfort & convenience with a rich amenity list is there to satisfy your every need. • Fully Equipped Kitchen • Queen Bed • Flat-Screen TVs • Open Concept Design Living Area • Pool • Gym • Free Private Parking Learn more below!

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.

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.

Vivi's Hideaway
Enjoy this peaceful and centrally-located apartment, with sweeping 21st floor views of San Jose and the surrounding mountains. Fast internet, cool a/c, and a luxurious king sized, memory foam mattress await you after a day of exploring the Central Valley. Located in an exclusive high rise apartment, you will have access to one of the only rooftop pools in the central valley, a full gym, and inspiring coworking areas.
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

Casa Delios, Luxury Near the Airport, Private Pool

8p Luxury Townhouse-Concierge & Cleaning

Beautiful house with pool in Heredia Centro

Playa Bejuco Condominium 243

Casa Escobar
Condo rentals with a pool

Loft 25th Floor | Panoramic San José View A/C

Studio with view, balcony and free parking · URBN

Perfect City Sunset Retreat 18th floor

Urban Jewel on the 30th floor; SECRT

Industrial 2BR perfect location w/AC + sunset view

Skyline Loft 22nd Fl • Views + Pool + Gym + AC

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

The Gourmet Terrace & Coffee View w/AC
Other vacation rentals with a pool

Loft with a balcony, panoramic view, and private parking

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

Urban Vista iFreses, 2nd floor! AC, TV and Pool

Modern studio with spectacular view and amenities

Breathtaking Mountain View Apt.

Ifreses Apartment: clean/balcony/WiFi/desk

Exclusive Apartment in Downtown Costa Rica

Apartment with excellent location. AC/wifi
When is the best time to visit Guadalupe?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$11,867 GYD | G$11,867 GYD | G$12,075 GYD | G$10,826 GYD | G$9,993 GYD | G$10,618 GYD | G$10,201 GYD | G$10,410 GYD | G$10,201 GYD | G$11,034 GYD | G$11,659 GYD | G$12,908 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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- Jaco Beach
- Dominical Beach
- Playa Blanca
- Parque Nacional Manuel Antonio
- La Sabana Park
- Parque Diversiones
- Marina Pez Vela
- Poás Volcano National Park
- Chirripo National Park
- Parque Nacional Braulio Carrillo
- Parque Nacional Los Quetzales
- University of Costa Rica
- Carara National Park
- Turrialba Volcano National Park
- Multiplaza Escazú
- El Miro
- Children’s Museum
- Hacienda Alsacia Starbucks Coffee Farm
- La Cruz del Monte de la Cruz
- Britt Coffee Tour
- Parque Central
- Plaza de la Cultura
- San Jose Central Market
- Río Agrio Waterfall





