
Holiday rentals with a pool in Guadalupe
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Guadalupe
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

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, sala de cine, roof garden para disfrutar de vistas únicas de San José.

Luxury 14th-Floor Apartment with Views in San José
Discover tranquility in this centrally-located haven near Barrio Escalante. Enjoy a cozy retreat just steps from the city’s top restaurants, offering local and international cuisine. You will find a grocery store just in front of the main gate. Next to the building, there is a bowling and a Mall 5 minutes waking. Immerse yourself in culture with nearby museums, cinemas, and art scenes. You’re less than an hour from stunning natural attractions-volcanoes, mountains, and beaches await!

Studio with a beautiful view
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.

21st Floor Cozy Apartment w A/C
Your home away from home awaits you. An industrial design unit with both antique and contemporary accents are throughout this cozy space to help make your experience unforgettable. Welcome to this tastefully decorated sanctuary located in San José’s Barrio Escalante district, known for its eclectic cuisine and selection as one of the world’s “Coolest Neighborhoods” by Time Out magazine. This unit is perfect for singles and couples. Enjoy the breathtaking sunsets from the private balcony.

Cityscape iFreses, 20th floor! AC, TV and Pool
Discover this elegant, fully furnished apartment in one of the safest residential-commercial areas of San José, featuring 24/7 security. Situated in the exclusive iFreses Condominium, this apartment offers stunning city views and amazing amenities! Its strategic location places you within walking distance of shopping centers, supermarkets, coffee shops, restaurants, banks, and universities. Bus and taxi stops are just 50 meters away, and the train station is 200 meters away.

Penthouse in San Pedro, view of the gods. Luxury, A/C.
This special place is close to everything, making it easy to plan your visit. Luxury two-story penthouse 16 and 17!A/C. View of the gods! With a unique and privileged view, in the exclusive area of Los Yoses. Close to all the Escalante cuisine. Just 3 minutes from the city of San José. With a spectacular view of the mountains to the south of the city and the beautiful sunsets to the west. Just meters from supermarkets and restaurants, parking included for our customers.

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.

Gorgeous sunsets at charming apartment in downtown
We welcome you to your new and luxurious apartment in the center of the city, located in one of the most iconic residential buildings in the country, with a variety of amenities and just a 5-minute walk away from the most famous gastronomic area of San José. The neighborhood is safe, and has different areas according to your preference (whether it's a night out, or a quiet afternoon in the park). A/C, WiFi 500 mbps, and parking included.

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 .

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.

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 ***

URBN Cornerview city and mountain view-26th floor
Located in San Jose’s trendiest neighborhood, with all the amenities you need for a nourishing stay in the city. This is the ideal base for exploring the neighborhood of Barrio Escalante, with dozens of independent restaurants, cafes, and shops just steps away. The building amenities include: heated pool, gym, yoga room, coworking spaces, cinema, library, pet shower, laundry room and more.
Popular amenities for Guadalupe rentals with a pool
House rentals with a pool

Relaxing House in Condo Costa Rica

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

Casa Maria

Casa Gaudi🦚Near SJO🦚Private Pool & King BD

Casa Delios, Luxury Near the Airport, Private Pool

3BR Home w/ AC & high speed internet near airport

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

City Scapes Home2BR 2131ft2 Amenities Security24X7
Apartment rentals with a pool

URBN-Escalante apartment with parking

Fully equipped apartment in Nunciatura

AC and King Bed - Full Equipped Apartment

Modern/comfort great views 2Bdr 2Bath Escalante

Alicia's Garden Apartment and Secrt

Featured Apartment | 5 Stars Verified Reviews, AC

Super view and WiFi, 2 bedrooms, 2 bathrooms and 2 parking spaces

Modern apartment at gastronomic epicenter
Other holiday rentals with a pool

Relaxing Apt 20th Floor! Pool Wifi AC.

Apartment in EscalanteOlive Loft 14th

Apt. in safe area w/balcony, A/C, pool, gym

Panoramic Penthouse 21 Escalante

Modern studio with spectacular view and amenities

15th Floor Apt / Amazing Views • 20 min to Airport

Escalante Relax 12th

INSTAWORTHY CORNER VIEW * Downtown SJ * 200Mbps
Quick stats about holiday rentals with a pool in Guadalupe

Total holiday rentals
Explore 70 holiday rentals in Guadalupe

Nightly prices starting at
Guadalupe holiday rentals start at $26 SGD per night before taxes and fees

Verified guest reviews
Over 1,590 verified reviews to help you choose

Family-friendly holiday rentals
10 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
60 properties have a dedicated workspace

Wifi availability
70 of Guadalupe holiday rentals include wifi 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!
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- Rentals with a washing machine and dryer Guadalupe
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- Rentals with pools San Jose Province
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- Jaco Beach
- Dominical Beach
- La Sabana Park
- National Stadium of Costa Rica
- Parque Nacional Manuel Antonio
- Poás Volcano National Park
- Parque Diversiones
- Chirripo National Park
- Marina Pez Vela
- Parque Nacional Braulio Carrillo
- Parque Nacional Los Quetzales
- Irazú Volcano National Park
- Carara National Park
- La Cruz del Monte de la Cruz
- Turrialba Volcano National Park
- Children’s Museum
- Britt Coffee Tour
- Parque Viva
- Parque Central
- Hotel Pumilio
- Basilica De Nuestra Señora De Los Ángeles
- Costa Rica Institute of Technology
- Playa Jacó
- Multiplaza Curridabat




